Organic light emitting element and film

Abstract

An organic light emitting element which comprises compounds represented by the general formulae has excellent light emission characteristics. In the general formulae, one of X1 and X2 represents N, and the other represents B; R1 to R26, A1 and A2 represent H, D or a substituent; one of R112 and R113 represents CN or a triazinyl group; and the other, R111, R114 and R115 represent H, D, a donor group containing a substituted amino group, or an aryl group, and at least one of these moieties represents a substituted or fused carbazol-9-yl group.

Description

Organic light-emitting devices and films

[0001] The present invention relates to organic light-emitting devices and films having good light-emitting properties.

[0002] Active research is being conducted into improving the luminous efficiency of organic light-emitting devices such as organic light-emitting diodes (OLEDs). For example, Non-Patent Document 1 describes the use of a compound exhibiting a multiple resonance effect, such as 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (DABNA-1), to exhibit thermally activated delayed fluorescence due to a reverse intersystem crossing process, resulting in emission with a narrow half-width and high color purity. Such emission can achieve high luminous efficiency and is therefore useful for display-oriented applications. Non-Patent Documents 1 and 2 also describe the modification of DABNA-1 to adjust the energy levels of the highest accessible molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), thereby promoting the fluorescence emission process and reverse intersystem crossing process that contribute to light emission, thereby improving electroluminescence quantum efficiency.

[0003] Adv. Mater. 2016, 28, 2777-2781Angew. Chem. Int. Ed. 2018, 57, 11316-11320

[0004] Although various studies have been conducted on compounds that exhibit the multiple resonance effect, much remains unknown regarding the relationship between their structure and luminescence properties. To manufacture practical light-emitting devices, it is necessary to provide materials with even slightly better luminescence properties. It is also desirable not only to provide materials with excellent luminescence properties, but also to provide organic light-emitting devices with even better luminescence properties by selecting materials to be used in combination with the materials. Therefore, the present inventors have developed derivatives of compounds that exhibit the multiple resonance effect and have conducted extensive research with the aim of providing organic light-emitting devices with even better luminescence properties by selecting materials to be used in combination with the materials.

[0005] As a result of intensive research, the present inventors have found that, among compounds that exhibit the multiple resonance effect, those having a specific structure have excellent luminescence properties. Furthermore, they have found that these excellent luminescence properties are further improved by using them in combination with a material having a specific structure. The present invention has been proposed based on this finding and has the following configuration.

[0006] [1] 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): General formula (1): [In the general formula (1), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other as a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ is a nitrogen atom, and R ７ and R ８ and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ or any of the following are bonded to each other to form an aromatic ring or a heteroaromatic ring.] General Formula (2) [In the general formula (2), R １１２ and R １１３ One of R represents a cyano group or a substituted or unsubstituted triazinyl group. １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ each independently represents a hydrogen atom, a deuterium atom, a donor group containing a substituted amino group, or a substituted or unsubstituted aryl group (excluding donor groups containing a substituted amino group). １１２ and R １１３The other one and R １１１ , R １１４ , R １１５ At least one of R in the general formula (1) is independently a carbazol-9-yl group (the carbazol-9-yl group is at least substituted or further fused with a ring). ３ and R ６ [3] The organic light-emitting element according to [1], wherein R in general formula (1) is a substituent. ８ and R １２ and R are both substituents. ８ and R １２ is an alkyl group having 2 or more carbon atoms, preferably an alkyl group having 3 or more carbon atoms, more preferably an alkyl group having 3 to 8 carbon atoms, and even more preferably an alkyl group having 3 or 4 carbon atoms. [4] X in general formula (1) １ is a nitrogen atom, and X ２ [5] The organic light-emitting device according to any one of [1] to [3], wherein R in general formula (1) is a boron atom. ７ and R ８ , R １７ and R １８ are bonded to each other to form -B(R ３２ )-, and R ３２ [6] The organic light-emitting device according to any one of [1] to [4], wherein each independently represents a hydrogen atom, a deuterium atom, or a substituent. ７ and R ８ , R １７ and R １８ [7] The organic light-emitting device according to any one of [1] to [4], wherein R in the general formula (1) is bonded to each other to form —CO—. ７ and R ８ , R １７ and R １８ [8] The organic light-emitting device according to any one of [1] to [4], wherein R in general formula (1) is bonded to each other to form —CS—. ７ and R ８ , R １７ and R １８ are bonded to each other to form -N(R ２７ )-, and R ２７[9] The organic light-emitting device according to any one of [1] to [4], wherein each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６

[10] The organic light-emitting device according to any one of [1] to [9], wherein 1 to 6 pairs of the above are bonded to each other to form a benzofuran ring or a benzothiophene ring.

[11] The organic light-emitting device according to [1], wherein the compound represented by general formula (1) has a rotationally symmetric structure.

[12] The organic light-emitting device according to [1], wherein the compound represented by general formula (1) has any of the following structures. For example, a compound may be selected from the group consisting of nine compounds other than the compound on the top left.

[12] R in general formula (2) １１２is a cyano group or a substituted or unsubstituted triazinyl group.

[13] The organic light-emitting device according to any one of [1] to

[12] , wherein the donor group of general formula (2) contains a carbazol-9-yl structure.

[14] A film containing a compound represented by general formula (1) above and a compound represented by general formula (2).

[15] The film according to

[14] , wherein the content of the compound represented by general formula (1) is less than that of the compound represented by general formula (2).

[16] The film according to

[14] or

[15] , further containing a host material having a minimum excited singlet energy higher than that of the compound represented by general formula (1) and the compound represented by general formula (2).

[0007] The film of the present invention exhibits excellent orientation of the light-emitting material and can be suitably used in organic light-emitting devices. Furthermore, the organic light-emitting devices of the present invention exhibit excellent light-emitting properties. In particular, the organic light-emitting devices of the present invention have high luminous efficiency, long device life, and excellent durability.

[0008] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range including the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( ２ In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the representation of an atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, H is assumed to be bonded to the carbon atom constituting the ring skeleton at the omitted location. In this specification, the term "substituent" refers to an atom or atomic group other than a hydrogen atom or a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0009] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be described.

[0010] In general formula (1), X １ and X ２ In one embodiment of the present invention, X is a nitrogen atom and the other is a boron atom. １ is a nitrogen atom, and X ２ is a boron atom. In this case, R １７ and R １８ are bonded to each other as a single bond to form a pyrrole ring. １ is a boron atom, and X ２ is a nitrogen atom. In this case, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring.

[0011] In general formula (1), R １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８, R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. ７ and R ８ The ring structure formed by the bonding of R contains a boron atom and four carbon atoms as ring skeleton constituent atoms. １７ and R １８ The cyclic structure formed by bonding is X １ When X is a boron atom, the ring skeleton contains the boron atom and four carbon atoms. １ When R is a nitrogen atom, the cyclic structure is limited to a pyrrole ring. ２１ and R ２２ The cyclic structure formed by bonding is X ２ When X is a boron atom, the ring skeleton contains the boron atom and four carbon atoms. ２ When R is a nitrogen atom, the cyclic structure is limited to a pyrrole ring. ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ When R are bonded to each other to form a cyclic structure containing a boron atom, the cyclic structure is preferably a 5- to 7-membered ring, more preferably a 5- or 6-membered ring, and even more preferably a 6-membered ring. ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ When they are bonded to each other, they are bonded to each other to form a single bond, —O—, —S—, —N(R ２７ ) -, -C(R ２８ ) (R ２９ ) -, -Si(R ３０ ) (R ３１) -, -B(R ３２ )-, -CO-, -CS-, and preferably forms -O-, -S- or -N(R ２７ )-, and more preferably -N(R ２７ )-, where R ２７ ~R ３２ Each of R independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be a group selected from any of the substituent groups A to E described below, but is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and particularly preferably R ２７ is preferably a substituted or unsubstituted aryl group. ２７ ~R ３２ is a substituent, R ７ and R ８ R in the ring formed by bonding together ２７ ~R ３２ is R ６ and R ９ may further bond to at least one of the following to form a cyclic structure; １７ and R １８ R in the ring formed by bonding together ２７ ~R ３２ is R １６ and R １９ may further bond to at least one of the following to form a cyclic structure; ２１ and R ２２ R in the ring formed by bonding together ２７ ~R ３２ is R ２０ and R ２３ In one embodiment of the present invention, R ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ In one aspect of the present invention, only one pair of R ７ and R ８ , R １７ and R １８ , R ２１ and R ２２In one aspect of the present invention, only two pairs of R ７ and R ８ , R １７ and R １８ , R ２１ and R ２２ All of these are connected to each other.

[0012] R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６The cyclic structure formed by bonding together may be an aromatic ring or an aliphatic ring, may contain a heteroatom, and may further be fused with one or more other rings. The heteroatom referred to here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the cyclic structure formed include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an imidazoline ring, a furan ring, a thiophene ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentene ring, a cycloheptatriene ring, a cycloheptadiene ring, a cycloheptene ring, and a ring further fused with one or more rings selected from the group consisting of these rings. In a preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted benzene ring (which may be further fused with a ring), for example, a benzene ring optionally substituted with an alkyl group or an aryl group. In a preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted heteroaromatic ring, and is preferably a furan ring of benzofuran or a thiophene ring of benzothiophene. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ The number of combinations of R that are bonded together to form a cyclic structure may be 0, or may be, for example, any of 1 to 6. For example, it may be any of 1 to 4, and it is possible to select 1, 2, 3, or 4. In one embodiment of the present invention, R １ and R ２ , R ２ and R ３ , R ３ and R ４ In one embodiment of the present invention, a pair of R ５ and R ６ are bonded to each other to form a ring structure. ９ and R １０ , R １０ and R １１ , R １１ and R １２ In one embodiment of the present invention, a pair of R １ and R ２ , R １３ and R １４ are bonded to each other to form a cyclic structure. １ and R ２ , R ２ and R ３ , R ３ and R ４ are bonded to each other to form a cyclic structure, and R ５ and R ６ are bonded to each other to form a ring structure. ５ and R ６ , R １９ and R ２０ are all bonded to each other to form a ring structure.

[0013] Adjacent Rｎ (n=1 to 26) and R １ ~R ２６ is a hydrogen atom, a deuterium atom, or a substituent. As the substituent, a group selected from any one of the substituent groups A to E described below can be used. １ ~R ２６ Preferred substituents that R may have are substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups. For example, the substituent may be a substituted or unsubstituted aryl group, or for example, the substituent may be a substituted or unsubstituted alkyl group. The substituents of the alkyl group, aryl group, and heteroaryl group mentioned here can also be groups selected from any of substituent groups A to E, but are preferably one or more groups selected from the group consisting of alkyl groups, aryl groups, and heteroaryl groups, and are more preferably groups of substituent group E, which may be unsubstituted. In one preferred embodiment of the present invention, R １ ~R ６ At least one of R is a substituent, preferably a group of the substituent group E. For example, R ２ ~R ６ At least one of R is a substituent, preferably a group of the substituent group E. For example, R ５ and R ６ In a preferred embodiment of the present invention, at least one of R ３ and R ６ In a preferred embodiment of the present invention, at least one of X is a substituent, more preferably both are substituents, and are preferably groups in the substituent group E. １ is a nitrogen atom, R １５ and R ２０ At least one of R is a substituent, more preferably both are substituents, and are preferably groups in the substituent group E. １７ and R １８ In a preferred embodiment of the present invention, X ２ is a nitrogen atom, R １９ and R ２４At least one of R is a substituent, more preferably both are substituents, and are preferably groups in the substituent group E. ２１ and R ２２ are bonded to each other to form a single bond. ８ and R １２ In one embodiment of the present invention, at least one of R ８ , R １０ and R １２ is a substituent. ８ ~R １２ The substituent of R is preferably an unsubstituted alkyl group. ８ and R １２ is an alkyl group having 2 or more carbon atoms (preferably an alkyl group having 3 or more carbon atoms, more preferably an alkyl group having 3 to 8 carbon atoms, and even more preferably an alkyl group having 3 or 4 carbon atoms), the orientation becomes high when made into a film, which is preferable. ８ and R １２ is a substituent (preferably an alkyl group, more preferably an alkyl group having 2 or more carbon atoms, even more preferably an alkyl group having 3 or more carbon atoms, still more preferably an alkyl group having 3 to 8 carbon atoms, particularly preferably an alkyl group having 3 or 4 carbon atoms), and R １ ~R ６ It is particularly preferred that at least one of X is a substituent (preferably a group of the substituent group E). １ is a boron atom, R １３ and R １７ In one aspect of the present invention, at least one of X is a substituent, and preferably both are substituents. １ is a boron atom, R １３ , R １５ and R １７ is a substituent. １ is a boron atom, R １３ ~R １７ The substituent of X is preferably an unsubstituted alkyl group. ２ is a boron atom, R ２２ and R ２６ In one aspect of the present invention, at least one of X is a substituent, and preferably both are substituents.２ is a boron atom, R ２２ , R ２４ and R ２６ is a substituent. ２ is a boron atom, R ２２ ~R ２６ The substituent of is preferably an unsubstituted alkyl group. １ or X ２ Specific examples of the group bonded to a boron atom represented by are listed below. However, the groups bonded to a boron atom that can be employed in the present invention are not limited to the following specific examples. In this specification, a methyl group is represented by CH ３ * indicates a bond position.

[0014] In the following, R in general formula (1) １ ~R ２６ Here are some specific examples: １ ~R ７ , X １ is a nitrogen atom, R １３ ~R ２１ , X ２ is a nitrogen atom, R １８ ~R ２６ is preferably Z1 to Z9, and R ８ ~R １２ , X １ is a nitrogen atom, R ２２ ~R ２６ , X ２ is a nitrogen atom, R １３ ~R １７ As the groups, Z1 to Z7 are preferred. However, the groups bonded to boron atoms that can be employed in the present invention should not be construed as being limited by the following specific examples. D represents a deuterium atom. * represents the bonding position.

[0015] A １ and A ２ is a hydrogen atom, a deuterium atom or a substituent. As the substituent, a group selected from any one of the substituent groups A to E described below can be used. In a preferred embodiment of the present invention, A １ and A ２are each independently a hydrogen atom or a deuterium atom. １ and A ２ is a hydrogen atom. For example, A １ and A ２ is a deuterium atom. １ and A ２ One of A may be a substituent. １ and A ２ may each independently be a substituent. １ and A ２ A preferred substituent that can be adopted by the para-substituted benzene derivative is an acceptor group. The acceptor group is a group with a positive Hammett σp value. Here, the "Hammett σp value" was proposed by L. P. Hammett and quantifies the influence of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, it is a constant (σp) specific to the substituent in the para-substituted benzene derivative, which holds between the substituent and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant of the benzene derivative without a substituent, k is the rate constant of the benzene derivative substituted with a substituent, K0 is the equilibrium constant of the benzene derivative without a substituent, K is the equilibrium constant of the benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett σp value" in the present invention and the numerical values ​​of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991). １ and A ２The acceptor group that can be adopted is more preferably a group having a Hammett σp value of greater than 0.2. Examples of groups having a Hammett σp value of greater than 0.2 include a cyano group, an aryl group substituted with at least a cyano group, a group containing a fluorine atom, and a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton constituent atom. The aryl group substituted with at least a cyano group may be substituted with a substituent other than a cyano group (e.g., an alkyl group or an aryl group), or may be an aryl group substituted only with a cyano group. The aryl group substituted with at least a cyano group is preferably a phenyl group substituted with at least a cyano group. The number of cyano group substitutions is preferably 1 or 2, for example, it may be 1 or 2. Examples of groups containing fluorine atoms include fluorine atoms, fluorinated alkyl groups, and aryl groups substituted with at least a fluorine atom or a fluorinated alkyl group. The fluorinated alkyl group is preferably a perfluoroalkyl group, preferably having 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. Furthermore, a heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of rings after fusion is preferably 2 to 6, and can be selected from 2 to 4, or can be 2. Specific examples of rings constituting a heteroaryl group include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, and a naphthyridine ring other than a quinazoline ring or a quinoxaline ring. The ring constituting the heteroaryl group may be substituted with a deuterium atom or a substituent, and examples of the substituent include one group selected from the group consisting of an alkyl group, an aryl group, and a heteroaryl group, or a group formed by combining two or more of these groups. A １ and A ２ A particularly preferred acceptor group is a cyano group. １ and A ２ In one embodiment of the present invention, at least one of A is an acceptor group. １ and A２ In one aspect of the present invention, only one of A is an acceptor group. １ and A ２ In one aspect of the present invention, both A and A are the same acceptor group. １ and A ２ are different acceptor groups. １ and A ２ is a cyano group. １ and A ２ is a halogen atom, for example a bromine atom.

[0016] Specific examples of acceptor groups that can be used in the present invention are shown below. However, the acceptor groups that can be used in the present invention should not be construed as being limited by the following specific examples. Methyl groups are omitted in this specification. Therefore, for example, A15 indicates a group containing two 4-methylphenyl groups. Furthermore, "D" represents a deuterium atom. * indicates a bonding position.

[0017] In addition, X １ is a nitrogen atom, and R ７ and R ８ are bonded via a nitrogen atom to form a 6-membered ring, and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６are bonded to each other to form an aromatic ring (a substituted or unsubstituted benzene ring which may be fused) or a heteroaromatic ring (preferably a furan ring of a substituted or unsubstituted benzofuran which may be fused, or a thiophene ring of a substituted or unsubstituted benzothiophene which may be fused). １ is a boron atom, and X ２ is a nitrogen atom, and R ７ and R ８ , R １７ and R １８ are bonded to each other to form a cyclic structure containing a boron atom, the cyclic structure is a 5- to 7-membered ring, and when it is a 6-membered ring, R ７ and R ８ , R １７ and R １８ are bonded to each other to form -B(R ３２ )-, -CO-, -CS- or -N(R ２７ )- is formed. ２７ preferably represents a hydrogen atom, a deuterium atom or a substituent.

[0018] X in general formula (1) １ When X in general formula (1) is a nitrogen atom, the compound of the present invention has the following skeleton (1a): ２ When is a nitrogen atom, the compound of the present invention has the following skeleton (1b):

[0019] Each hydrogen atom in the skeletons (1a) and (1b) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atoms may be substituted with a linking group together with the adjacent hydrogen atoms to form a cyclic structure. For details, see the corresponding R in general formula (1). １ ~R ２６ , A １ , A ２ can be referred to. Examples include compounds in which the phenyl groups bonded to the boron atoms in skeletons (1a) and (1b) are all substituted with mesityl groups, 2,6-diisopropylphenyl groups, or 2,4,6-triisopropylphenyl groups. In one embodiment of the present invention, each hydrogen atom in skeletons (1a) and (1b) is substituted with a linking group together with the adjacent hydrogen atom, so that a cyclic structure is not formed.

[0020] A preferred group of compounds having the skeleton (1a) includes compounds represented by the following general formula (1a):

[0021] In the general formula (1a), Ar １ ~Ar ４ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ４１ and R ４２ each independently represents a substituted or unsubstituted alkyl group. m1 and m2 each independently represents an integer of 0 to 5, n1 and n3 each independently represents an integer of 0 to 4, and n2 and n4 each independently represents an integer of 0 to 3. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. It is preferred that at least one of n1 to n4 is 1 or greater, and that m1 and m2 are each independently an integer from 1 to 5. In one embodiment of the present invention, n1 to n4 each independently represent an integer from 0 to 2. In a preferred embodiment of the present invention, at least one of n1 to n4 is 1 or greater, preferably at least one of n1 and n2 is 1 or greater, and at least one of n3 and n4 is 1 or greater. In one embodiment of the present invention, n1 and n3 are each independently 1 or 2, and n2 and n4 are 0. In one embodiment of the present invention, n2 and n4 are each independently 1 or 2, and n1 and n3 are 0. In one embodiment of the present invention, n1 to n4 are each independently 1 or 2. In one embodiment of the present invention, n1 and n3 are equal, and n2 and n4 are equal. In one embodiment of the present invention, n1 and n3 are 1, and n2 and n4 are 0. In one embodiment of the present invention, n1 and n3 are 0, and n2 and n4 are 1. In one embodiment of the present invention, n1 to n4 are all 1. Ar １ ~Ar ４ The bonding position of Ar may be at least one of the 3- and 6-positions, at least one of the 2- and 7-positions, at least one of the 1- and 8-positions, or at least one of the 4- and 5-positions of the carbazole ring.１ ~Ar ４ The bonding positions of Ar may be both the 3- and 6-positions, both the 2- and 7-positions, both the 1- and 8-positions, or both the 4- and 5-positions of the carbazole ring. For example, at least one of the 3- and 6-positions can be preferably selected, or both the 3- and 6-positions can be more preferably selected. In a preferred embodiment of the present invention, Ar １ ~Ar ４ In a preferred embodiment of the present invention, Ar １ ~Ar ４ are each independently a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl group or naphthyl group, and even more preferably a substituted or unsubstituted phenyl group. Examples of the substituent include a group selected from any of the substituent groups A to E described below, but an unsubstituted phenyl group is also preferred. Ar １ ~Ar ４ Preferred specific examples of R include a phenyl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, and a terphenyl group. In one embodiment of the present invention, m1 and m2 each independently represent 0. In one embodiment of the present invention, m1 and m2 each independently represent an integer of 1 to 5. In one embodiment of the present invention, m1 and m2 are equal. In one embodiment of the present invention, R ４１ and R ４２ is an alkyl group having 1 to 6 carbon atoms, and can be selected from alkyl groups having 1 to 3 carbon atoms, for example, or a methyl group. The substitution positions of the alkyl group can be, with the carbon atom bonded to the boron atom being the 1st position, the 2nd position only, the 3rd position only, the 4th position only, the 3rd and 5th positions, the 2nd and 4th positions, the 2nd and 6th positions, or the 2nd, 4th and 6th positions, and the like, with at least the 2nd position being preferred, and at least the 2nd and 6th positions being more preferred. A １ and A ２ For the explanation and preferred range of , please refer to the corresponding description of general formula (1).

[0022] Specific examples of the compound represented by general formula (1a) are listed below. The compounds of general formula (1a) that can be used in the present invention are not limited to the specific examples listed below. For example, a preferred group can be the group consisting of the remaining compounds excluding the compound in the center of the fourth row below and the compound in the center of the eighth row below.

[0023] Another group of specific examples of the compound represented by general formula (1a) is shown below. The compounds of general formula (1a) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0024] A preferred group of compounds having the skeleton (1b) includes compounds represented by the following general formula (1b):

[0025] In general formula (1b), Ar ５ ~Ar ８ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ４３ and R ４４ each independently represents a substituted or unsubstituted alkyl group. m3 and m4 each independently represent an integer of 0 to 5, n6 and n8 each independently represent an integer of 0 to 3, and n5 and n7 each independently represent an integer of 0 to 4. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５ ~Ar ８ , R ４３ and R ４４ , m3 and m4, n5 to n8, A １ , A２ For details, see Ar in general formula (1a). １ ~Ar ４ , R ４１ and R ４２ , m1 and m2, n1 to n4, A １ , A ２ It is preferable that at least one of n5 to n8 is 1 or more, and m3 and m4 each independently represent an integer of 1 to 5.

[0026] Specific examples of the compound represented by general formula (1b) are listed below. The compounds of general formula (1b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0027] R in general formula (1) ７ and R ８ When these are bonded together to form N-Ph, the compounds of the present invention are １ is a nitrogen atom, the following skeleton (2a) is obtained, ２ When is a nitrogen atom, for example, it has the following skeleton (2b): Ph is a phenyl group. Skeleton (2a)

[0028] Each hydrogen atom in the skeletons (2a) and (2b) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atoms may be substituted with a linking group together with the adjacent hydrogen atoms to form a cyclic structure. For details, see the corresponding R in general formula (1). １ ~R ２６ , A １ , A ２ can be referred to. At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in the skeleton (2a) is substituted with a substituted or unsubstituted aryl group. In one embodiment of the present invention, each hydrogen atom in the skeletons (2a) and (2b) is substituted with a linking group together with the adjacent hydrogen atom, so that a cyclic structure is not formed.

[0029] A preferred group of compounds having the skeleton (2a) includes compounds represented by the following general formula (2a):

[0030] In the general formula (2a), Ar ９ ~Ar １４ Each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n9, n11, n12, and n14 each independently represent an integer of 0 to 4, and n10 and n13 each independently represent an integer of 0 to 2. However, at least one of n9, n10, n12, and n13 is 1 or greater. A １ , A ２ each independently represent a hydrogen atom, a deuterium atom, or a substituent. In one aspect of the present invention, n9 to n14 each independently represent an integer of 0 to 2. In one aspect of the present invention, at least one of n9 to n14 is 1 or greater; for example, n9 and n12 can be 1 or greater, or n10 and n13 can be 1 or greater. In a preferred aspect of the present invention, at least one of n9, n10, n12, and n13 is 1 or greater. In one aspect of the present invention, n9 and n12 are each independently 1 or 2, and n10, n11, n13, and n14 are 0. In one aspect of the present invention, n10 and n13 are each independently 1 or 2, and n9, n11, n12, and n14 are 0. In one aspect of the present invention, n9 and n12 are each independently 1 or 2, n10 and n13 are each independently 1 or 2, and n11 and n14 are 0. In one embodiment of the present invention, n9 to n14 are all 1. ９ ~Ar １４ The bonding positions of Ar may be the 3- and 6-positions of the carbazole ring or other positions. ９ ~Ar １４ are all the same group. ９ ~Ar １４ For preferred groups, Ar １ ~Ar ４ Reference can be made to the corresponding description in １ and A ２ For the explanation and preferred range of , please refer to the corresponding description of general formula (1).

[0031] Specific examples of the compound represented by general formula (2a) are listed below. The compounds of general formula (2a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0032] A preferred group of compounds having the skeleton (2b) includes compounds represented by the following general formula (2b):

[0033] In the general formula (2b), Ar １５ ~Ar ２０ Each of n15, n17, n18, and n20 independently represents an integer of 0 to 4, and each of n16 and n19 independently represents an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １５ ~Ar ２０ , n15-n20, A １ , A ２ For details, see Ar in general formula (2a). ９ ~Ar １４ , n9 to n14, A １ , A ２ The following descriptions can be referred to in order.

[0034] Specific examples of the compound represented by general formula (2b) are listed below. The compounds of general formula (2b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0035] R in general formula (1) ７ and R ８ When these bond to each other to form a single bond, the compound of the present invention is X １ is a nitrogen atom, the following skeleton (3a) is obtained, and X ２ When is a nitrogen atom, for example, it has the following skeleton (3b).

[0036] Each hydrogen atom in the skeletons (3a) and (3b) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atoms may be substituted with a linking group together with the adjacent hydrogen atoms to form a cyclic structure. For details, see the corresponding R in general formula (1). １ ~R ２６ , A １ , A ２ In one embodiment of the present invention, each hydrogen atom in the skeletons (3a) and (3b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0037] A preferred group of compounds having the skeleton (3a) includes compounds represented by the following general formula (3a):

[0038] In the general formula (3a), Ar ２１ ~Ar ２６ Each of n21, n23, n24, and n26 independently represents an integer of 0 to 4, and each of n22 and n25 independently represents an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２１ ~Ar ２５ , n21 to n25 are each independently selected from the group consisting of Ar in general formula (2a) and Ar in general formula (2a). ９ ~Ar １４ , n9 to n14, A １ , A ２ The description can be referred to.

[0039] Specific examples of the compound represented by general formula (3a) are listed below. The compounds of general formula (3a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0040] A preferred group of compounds having the skeleton (3b) includes compounds represented by the following general formula (3b):

[0041] In the general formula (3b), Ar ２７ ~Ar ３２ Each of n27, n29, n30, and n32 independently represents an integer of 0 to 4, and each of n28 and n31 independently represents an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２７ ~Ar ３２ , n27-n32, A １ , A ２ For details, see Ar in general formula (2b). １５ ~Ar ２０ , n15-n20, A １ , A ２ The following descriptions can be referred to in order.

[0042] Specific examples of the compound represented by general formula (3b) are listed below. The compounds of general formula (3b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0043] In a preferred embodiment of the present invention, a compound in which another ring is fused to the two benzene rings constituting the carbazole moiety present in general formula (1) is selected. Among these, a compound in which a benzofuran ring is fused, a compound in which a benzothiophene ring is fused, or a compound in which a benzene ring is fused can be particularly preferably selected. Below, these ring-fused compounds will be described with specific examples.

[0044] Preferred examples of such compounds include compounds in which a benzofuran ring or a benzothiophene ring is condensed with the benzene ring to which the boron atom is not directly bonded, out of the two benzene rings constituting the carbazole partial structure present in general formula (1). Examples of such compounds include compounds having the following skeleton (4a) and compounds having the following skeleton (4b).

[0045] In skeletons (4a) and (4b), Y １ ~Y ４ are each independently two hydrogen atoms, a single bond, or N(R ２７ The two hydrogen atoms here indicate that the two benzene rings bonded to the boron atom are not linked to each other. １ and Y ２ are the same, and Y ３ and Y ４ are preferably the same, but may be different. １ ~Y ４ is a single bond. In one aspect of the present invention, Y １ ~Y ４ is N(R ２７ ) R ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ ~Z ４ each independently represents an oxygen atom or a sulfur atom. １ and Z ２ are the same, and Z ３ and Z ４ are preferably the same, but may be different. １ ~Z ４ is an oxygen atom. In this case, the furan ring of benzofuran is fused to the benzene ring constituting the carbazole partial structure in (4a) and (4b). The orientation of the fused furan ring is not limited. In one embodiment of the present invention, Z １ ~Z ４ is a sulfur atom. In this case, the thiophene ring of benzothiophene is fused to the benzene ring constituting the carbazole partial structure in (4a) and (4b). The orientation of the fused thiophene ring is not limited. Each hydrogen atom in the skeletons (4a) and (4b) may be substituted with a deuterium atom or a substituent. In addition, it may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (1). １ ~R ２６ , A １ , A ２In one embodiment of the present invention, each hydrogen atom in the skeletons (4a) and (4b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0046] As a preferred group of compounds having the skeleton (4a), compounds represented by the following general formula (4a) can be exemplified. X in the specific examples is an oxygen atom or a sulfur atom, and compounds in which X is an oxygen atom and compounds in which X is a sulfur atom are respectively disclosed. X in the specific examples of compounds represented by other general formulas below also has the same meaning. General formula (4a)

[0047] In the general formula (4a), Ar ５１ and Ar ５２ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５１ and R ５２ Each of m51 and m52 independently represents an integer of 0 to 4. Each of n51 and n52 independently represents an integer of 0 to 2. Y １ ~Y ４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ ~Z ４ each independently represents an oxygen atom or a sulfur atom. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n51 and n52 are the same number. For example, n51 and n52 may be 0, or n51 and n52 may be 1. In one embodiment of the present invention, m51 and m52 are the same number. In one embodiment of the present invention, m51 and m52 are integers of 0 to 3. For example, m51 and m52 may be 0, m51 and m52 may be 1, m51 and m52 may be 2, or m51 and m52 may be 3. Ar ５１ , Ar ５２ , R５１ , R ５２ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ ~Ar ４ , R ４１ ~R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0048] Specific examples of compounds represented by general formula (4a) are listed below. The compounds of general formula (4a) that can be used in the present invention are not limited to the following group of specific examples. Regarding specific examples containing X, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the X in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0049] Another group of specific examples of the compound represented by general formula (4a) is shown below. The compounds of general formula (4a) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0050] A preferred group of compounds having the skeleton (4b) includes compounds represented by the following general formula (4b):

[0051] In the general formula (4b), Ar ５３ and Ar ５４ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５３ and R ５４Each of m53 and m54 independently represents an integer of 0 to 4. Each of n53 and n54 independently represents an integer of 0 to 2. Y ３ and Y ４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ３ and Z ４ each independently represents an oxygen atom or a sulfur atom. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５３ , Ar ５４ , R ５３ , R ５４ , m53, m54, n53, n54, A １ , A ２ For details, see Ar in general formula (4a). ５１ , Ar ５２ , R ５１ , R ５２ , m51, m52, n51, n52, A １ , A ２ The description can be referred to.

[0052] Specific examples of compounds represented by general formula (4b) are listed below. The compounds of general formula (4b) that can be used in the present invention are not limited to the specific examples below. Specific examples containing X are considered to disclose compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0053] Preferred examples of such compounds include compounds in which a benzofuran ring or a benzothiophene ring is fused to the benzene ring directly bonded to a boron atom, out of the two benzene rings constituting the carbazole moiety present in general formula (1). Examples of such compounds include compounds having the following skeleton (5a) and compounds having the following skeleton (5b).

[0054] In skeletons (5a) and (5b), Y ５ ~Y ８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Z. ５ ~Z ８ Each independently represents an oxygen atom or a sulfur atom. ５ ~Y ８ , Z ５ ~Z ８ For details of the above, please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (5a) and (5b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0055] A preferred group of compounds having the skeleton (5a) includes compounds represented by the following general formula (5a):

[0056] In the general formula (5a), Ar ５５ and Ar ５６ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５５ and R ５６ Each of m55 and m56 independently represents an integer of 0 to 4. Each of n55 and n56 independently represents an integer of 0 to 4. Y ５ and Y ６ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ５ and Z ６ each independently represents an oxygen atom or a sulfur atom. １ , A ２each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n55 and n56 are integers of 0 to 2. For example, n55 and n56 may be 0, or n55 and n56 may be 1. In one embodiment of the present invention, m51 and m52 are the same number. For details of m55 and m56, please refer to the description of m51 and m52 in general formula (4a). Ar ５５ , Ar ５６ , R ５５ , R ５６ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ , Ar ３ , R ４１ , R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0057] Specific examples of compounds represented by general formula (5a) are listed below. Compounds of general formula (5a) that can be used in the present invention are not limited to the following group of specific examples. Specific examples containing X are considered to disclose compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0058] Another group of specific examples of the compound represented by general formula (5a) is shown below. The compounds of general formula (5a) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0059] A preferred group of compounds having the skeleton (5b) includes compounds represented by the following general formula (5b):

[0060] In the general formula (5b), Ar ５７ and Ar ５８R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ５７ and R ５８ Each of m57 and m58 independently represents an integer of 0 to 4. Each of n57 and n58 independently represents an integer of 0 to 4. Y ７ and Y ８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ７ and Z ８ each independently represents an oxygen atom or a sulfur atom. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５７ , Ar ５８ , R ５７ , R ５８ , m57, m58, n57, n58, A １ , A ２ For details, see Ar in general formula (5a). ５５ , Ar ５６ , R ５５ , R ５６ , m55, m56, n55, n56, A １ , A ２ The description can be referred to.

[0061] Specific examples of compounds represented by general formula (5b) are listed below. The compounds of general formula (5b) that can be used in the present invention are not limited to the following group of specific examples. Regarding specific examples containing X, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the X in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0062] Another group of specific examples of the compound represented by general formula (5b) is shown below. The compounds of general formula (5b) that can be used in the present invention are not to be construed as being limited by the following group of specific examples.

[0063] Preferred examples of such compounds include compounds in which a benzofuran ring or a benzothiophene ring is fused to both of the two benzene rings constituting the carbazole moiety present in general formula (1). Examples of such compounds include a compound having the following skeleton (6a) and a compound having the following skeleton (6b).

[0064] In skeletons (6a) and (6b), Y ９ ~Y １２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Z. ９ ~Z １６ each independently represents an oxygen atom or a sulfur atom. ９ ~Z １６ are preferably the same, but may be different. ９ ~Z １６ is an oxygen atom. In one aspect of the present invention, Z ９ ~Z １６ is a sulfur atom. ９ ~Y １２ For details of the above, please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (6a) and (6b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0065] A preferred group of compounds having the skeleton (6a) includes compounds represented by the following general formula (6a):

[0066] In general formula (6a), R ５９ and R ６０ Each of m59 and m60 independently represents an integer of 0 to 4. Y ９ and Y１０ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. ９ ~Z １２ each independently represents an oxygen atom or a sulfur atom. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ５９ , R ６０ , m59, m60, Z ９ ~Z １２ , A １ , A ２ For details, see R in general formula (5a). ５５ , R ５６ , m55, m56, A １ , A ２ and Z in skeleton (6a) ９ ~Z １２ The description can be referred to.

[0067] Specific examples of compounds represented by general formula (6a) are listed below. The compounds of general formula (6a) that can be used in the present invention are not limited to the specific examples below. Regarding specific examples containing X, compounds in which all X in the molecule are oxygen atoms and compounds in which all X in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the X in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0068] A preferred group of compounds having the skeleton (6b) includes compounds represented by the following general formula (6b):

[0069] In general formula (6b), R ６１ and R ６２ Each of m61 and m60 independently represents an integer of 0 to 4. Y １１ and Y １２are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １３ ~Z １６ each independently represents an oxygen atom or a sulfur atom. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ６１ , R ６２ , m61, m62, Z １３ ~Z １６ , A １ , A ２ For details, see R in general formula (6a). ５９ , R ６０ , m59, m60, A １ , A ２ and Z in skeleton (6b) １３ ~Z １６ The description can be referred to.

[0070] Specific examples of compounds represented by general formula (6b) are listed below. The compounds of general formula (6b) that can be used in the present invention are not limited to the specific examples below. Regarding specific examples containing X, compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are considered to be disclosed. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0071] Preferred examples of such compounds include compounds in which a benzene ring is fused to the benzene ring to which a boron atom is not directly bonded, out of the two benzene rings constituting the carbazole moiety present in general formula (1). Examples of such compounds include compounds having the following skeleton (7a) and compounds having the following skeleton (7b).

[0072] In skeletons (7a) and (7b), Y ２１ ~Y ２４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Y.２１ ~Y ２４ For details, see Y in skeletons (4a) and (4b). １ ~Y ４ In one embodiment of the present invention, each hydrogen atom in the skeletons (7a) and (7b) is substituted with a linking group together with the adjacent hydrogen atom to form a ring structure.

[0073] A preferred group of compounds having the skeleton (7a) includes compounds represented by the following general formula (7a):

[0074] In the general formula (7a), Ar ７１ ~Ar ７４ Each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n71 and n73 each independently represent an integer of 0 to 2. n72 and n74 each independently represent an integer of 0 to 4. Y ２１ and Y ２２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n71 to n74 are integers of 0 to 2. In one embodiment of the present invention, n71 and n73 are the same number, and n72 and n74 are the same number. n71 to n74 may be the same number. For example, n71 to n74 may be 0. All of n71 to n74 may be 1. Also, for example, n71 and n73 may be 0, and n72 and n74 may be 1. Ar ７１ ~Ar ７４ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ ~Ar ４ , A １ , A ２ Reference can be made to the corresponding description in

[0075] Specific examples of the compound represented by general formula (7a) are listed below. The compounds of general formula (7a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0076] A preferred group of compounds having the skeleton (7b) includes compounds represented by the following general formula (7b):

[0077] In the general formula (7b), Ar ７５ ~Ar ７８ Each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n75 and n77 each independently represent an integer of 0 to 2. n76 and n78 each independently represent an integer of 0 to 4. Y ２３ and Y ２４ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom, or a substituent. For a detailed description of n75 to n78, please refer to the descriptions of n71 to n74 in general formula (7a) in order. ７５ ~Ar ７８ As for the preferred group, Ar in general formula (1a) １ ~Ar ４ Reference can be made to the corresponding description in

[0078] Specific examples of the compound represented by general formula (7b) are listed below. The compounds of general formula (7b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0079] Preferred examples of such compounds include compounds in which a benzene ring is fused to the benzene ring directly bonded to a boron atom, out of the two benzene rings constituting the carbazole moiety present in general formula (1). Examples of such compounds include compounds having the following skeleton (8a) and compounds having the following skeleton (8b).

[0080] In skeletons (8a) and (8b), Y ２５ ~Y ２８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Y. ２５ ~Y ２８ For details of the skeletons (4a) and (4b), please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (8a) and (8b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0081] A preferred group of compounds having the skeleton (8a) includes compounds represented by the following general formula (8a):

[0082] In the general formula (8a), Ar ７９ and Ar ８０ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ７１ and R ７２ Each of m71 and m72 independently represents an integer of 0 to 4. Each of n79 and n80 independently represents an integer of 0 to 4. Y ２５ and Y ２６ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n79 and n80 are integers of 0 to 2. In one embodiment of the present invention, n79 and n80 are the same number, and for example, both may be 0 or both may be 1. In one embodiment of the present invention, m71 and m72 are integers of 0 to 2. In one embodiment of the present invention, m71 and m72 are the same number, and for example, both may be 0 or both may be 1. Ar ７９ , Ar ８０ , R７１ , R ７２ , A １ , A ２ As for the preferred group, Ar in general formula (1a) １ , Ar ３ , R ４１ , R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0083] Specific examples of the compound represented by general formula (8a) are listed below. The compounds of general formula (8a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0084] A preferred group of compounds having the skeleton (8b) includes compounds represented by the following general formula (8b):

[0085] In the general formula (8b), Ar ８１ and Ar ８２ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ７３ and R ７４ Each of m73 and m74 independently represents an integer of 0 to 4. Each of n81 and n82 independently represents an integer of 0 to 4. Y ２７ and Y ２８ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ Each of m73, m74, n81, and n82 independently represents a hydrogen atom, a deuterium atom, or a substituent. For a detailed description of m73, m74, n81, and n82, please refer to the descriptions of m71, m72, n79, and n80 in general formula (8a). Ar ８１ , Ar ８２ , R ７３ , R ７４ , A １ , A２ As for the preferred group, Ar in general formula (1a) １ , Ar ３ , R ４１ , R ４２ , A １ , A ２ Reference can be made to the corresponding description in

[0086] Specific examples of the compound represented by general formula (8b) are listed below. The compounds of general formula (8b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0087] Preferred examples of such compounds include compounds having a benzene ring fused to both of the two benzene rings constituting the carbazole moiety present in general formula (1). Examples of such compounds include a compound having the following skeleton (9a) and a compound having the following skeleton (9b).

[0088] In skeletons (9a) and (9b), Y ２９ ~Y ３２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents Y. ２９ ~Y ３２ For details of the above, please refer to the corresponding descriptions of the skeletons (4a) and (4b). In one embodiment of the present invention, each hydrogen atom in the skeletons (9a) and (9b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0089] A preferred group of compounds having the skeleton (9a) includes compounds represented by the following general formula (9a):

[0090] In general formula (9a), R ７５ and R ７６ Each of m75 and m76 independently represents an integer of 0 to 4. Y ２９ and Y ３０ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ７５ , R ７６ , m75, m76, A １ , A ２ For details, see R in general formula (8a). ７１ , R ７２ , m71, m72, A １ , A ２ The description can be referred to.

[0091] Specific examples of the compound represented by general formula (9a) are listed below. The compounds of general formula (9a) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0092] A preferred group of compounds having the skeleton (9b) includes compounds represented by the following general formula (9b):

[0093] In general formula (9b), R ７７ and R ７８ Each of m77 and m78 independently represents an integer of 0 to 4. Y ３１ and Y ３２ are each independently two hydrogen atoms, a single bond, or N(R ２７ ) represents. ２７ represents a hydrogen atom, a deuterium atom or a substituent. １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ７７ , R ７８ , m77, m78, A １ , A ２ For details, see R in general formula (8a). ７１ , R ７２ , m71, m72, A １ , A ２ The description can be referred to.

[0094] Specific examples of the compound represented by general formula (9b) are listed below. The compounds of general formula (9b) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0095] As the compound represented by general formula (1), a compound containing four or more carbazole moieties in the molecule is also preferred. An example of such a compound is a compound having the following skeleton (10): Skeleton (10)

[0096] Each hydrogen atom in the skeleton (10) may be substituted with a deuterium atom or a substituent. In addition, the hydrogen atom may be substituted with a linking group together with the adjacent hydrogen atom to form a cyclic structure. For details, see the corresponding R in general formula (1). １ ~R ２６ , A １ , A ２ can be referred to. At least one hydrogen atom of the benzene ring constituting the carbazole partial structure contained in the skeleton (10) is substituted with a substituted or unsubstituted aryl group. In one embodiment of the present invention, each hydrogen atom in the skeleton (10) is substituted with a linking group together with the adjacent hydrogen atom, so that a cyclic structure is not formed.

[0097] A preferred group of compounds having the skeleton (10) includes compounds represented by the following general formula (10):

[0098] In the general formula (10), Ar ９１ ~Ar ９４each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. n91 and n93 each independently represent an integer of 0 to 4, and n92 and n94 each independently represent an integer of 0 to 3. The α ring, β ring, γ ring, and δ ring may be substituted, and at least one ring is substituted with a substituted or unsubstituted aryl group, or is fused with an optionally substituted benzene ring, or is fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. In one embodiment of the present invention, n91 to n94 are integers of 0 to 2. In one embodiment of the present invention, n91 and n93 are the same number, and n92 and n94 are the same number. n91 to n94 may all be the same number, for example, all may be 0 or all may be 1. Ar ９１ ~Ar ９４ As for the preferred group, Ar in general formula (1a) １ ~Ar ４Reference can be made to the corresponding description in the above. In one embodiment of the present invention, the α-ring and the γ-ring have the same substituent or the same fused structure, and the β-ring and the δ-ring have the same substituent or the same fused structure. In one embodiment of the present invention, the β-ring and the δ-ring are both substituted with a substituted or unsubstituted aryl group, are fused with an optionally substituted benzene ring, or are fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. In one embodiment of the present invention, the α-ring and the γ-ring are both substituted with a substituted or unsubstituted aryl group, are fused with an optionally substituted benzene ring, or are fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. In one embodiment of the present invention, all of the α-ring, the β-ring, the γ-ring, and the δ-ring are substituted with a substituted or unsubstituted aryl group, are fused with an optionally substituted benzene ring, or are fused with a furan ring of a substituted or unsubstituted benzofuran or a thiophene ring of a substituted or unsubstituted thiophene. A １ and A ２ For the explanation and preferred range of , please refer to the corresponding description of general formula (1).

[0099] Specific examples of the compound represented by general formula (10) are given below. The compounds of general formula (10) that can be used in the present invention are not to be construed as being limited by the following specific examples.

[0100] The compound represented by general formula (1) may have an asymmetric skeleton, for example, a compound having an asymmetric skeleton such as the following skeleton (11a) or skeleton (11b).

[0101] In skeletons (11a) and (11b), Z １７ and Z １８ each independently represents an oxygen atom or a sulfur atom. In one embodiment of the present invention, each hydrogen atom in the skeletons (11a) and (11b) is substituted with a linking group together with the adjacent hydrogen atom to form no cyclic structure.

[0102] A preferred group of compounds having the skeleton (11a) includes compounds represented by the following general formula (11a):

[0103] In the general formula (11a), Ar ８３ ~Ar ８５ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ８３ and R ８４ Each of Z independently represents a substituted or unsubstituted alkyl group. １７ represents an oxygen atom or a sulfur atom. m83 and m84 each independently represent an integer of 0 to 5. n83 represents an integer of 0 to 4, and n84 and n85 each independently represent an integer of 0 to 3. Ar ８３ ~Ar ８５ , R ８３ , R ８４ For detailed explanations and preferred ranges of m83, m84, and n83 to n85, see Ar １ , Ar ２ , Ar ４ , R ４１ , R ４２ , m1, m2, n1, n2, and n4.

[0104] Specific examples of the compound represented by general formula (11a) are given below. The compounds of general formula (11a) that can be used in the present invention are not limited to the following specific examples. In the following specific examples, a compound in which all X's in the molecule are oxygen atoms and a compound in which all X's in the molecule are sulfur atoms are respectively disclosed. A compound in which some of the X's in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0105] A preferred group of compounds having the skeleton (11b) includes compounds represented by the following general formula (11b):

[0106] In the general formula (11b), Ar ８６ ~Ar ８８ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted aryl group can be preferably selected. ８６ and R ８７ Each of Z independently represents a substituted or unsubstituted alkyl group. １８ represents an oxygen atom or a sulfur atom. m86 and m87 each independently represent an integer of 0 to 5. n86 represents an integer of 0 to 4, and n87 and n88 each independently represent an integer of 0 to 3. Ar ８６ ~Ar ８８ , R ８６ , R ８７ For detailed explanations and preferred ranges of m86, m87, and n86 to n88, see Ar １ , Ar ２ , Ar ４ , R ４１ , R ４２ , m1, m2, n1, n2, and n4.

[0107] Specific examples of the compound represented by general formula (11b) are listed below. The compounds of general formula (11b) that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, a compound in which all Xs in the molecule are oxygen atoms and a compound in which all Xs in the molecule are sulfur atoms are respectively disclosed. A compound in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0108] As the compound represented by general formula (1), R ５ A compound in which R is a donor group can be preferably used. ５ A compound in which R is a donor group tends to have a high molar absorption coefficient and high luminous efficiency. ３ In a preferred embodiment of the present invention, R ３ is not a donor group. In a preferred embodiment of the present invention, R １ ~R７ Among them, R ５ Only R is a donor group, or none of R is a donor group (particularly a donor group with a σp value of −0.2 or less). A donor group is a group with a negative Hammett σp value. ５ The donor group preferably has a σp value of −0.2 or less, for example, −0.4 or less, or for example, −0.6 or less. A preferred donor group is a substituted amino group, preferably a substituted or unsubstituted diarylamino group. The aryl group may be a monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of rings after condensation is preferably 2 to 6, for example, selected from 2 to 4, or may be 2. The two aryl groups constituting the diarylamino group may be the same or different. Furthermore, the two aryl groups may be linked by a single bond or a linking group. A preferred substituted or unsubstituted diarylamino group is a substituted or unsubstituted diphenylamino group. A substituted or unsubstituted carbazol-9-yl group in which two phenyl groups are bonded by a single bond may be used, or a substituted or unsubstituted diphenylamino group in which two phenyl groups are not bonded by a single bond may be used. R in general formula (1) １ ~R ７ When any of R is a substituted amino group, at least R ５ is preferably a substituted amino group, and R ５ More preferably, only R is a substituted amino group. ３ is not a substituted amino group. ５ is a donor group, and X １ is a nitrogen atom, R １６ or R １９ is preferably a donor group, and R １９ is more preferably a donor group. １ ~R ２６ may be, for example, all hydrogen atoms or all deuterium atoms, or, for example, R ３ , R ６ , R １５ , R ２０At least one of R may be a substituent (preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group), and the others may be hydrogen atoms or deuterium atoms. ５ is a donor group, and X １ is a boron atom, R ２０ or R ２３ is preferably a donor group, and R ２０ is more preferably a donor group. １ ~R ２６ may be, for example, all hydrogen atoms or all deuterium atoms, or, for example, R ３ , R ６ , R １９ , R ２４ At least one of R may be a substituent (preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group), and the others may be hydrogen atoms or deuterium atoms. ５ As a preferred group of compounds in which is a donor group, there can be mentioned compounds represented by the following general formula (12a) and compounds represented by the following general formula (12b):

[0109] In the general formula (12a) and the general formula (12b), Ar １ ~Ar ８ R each independently represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group can be preferably selected. ５ represents a donor group. ４１ ~R ４４ each independently represents a substituted or unsubstituted alkyl group. m1 to m4 each independently represents an integer of 0 to 5. n1, n3, n5, and n7 each independently represent an integer of 0 to 4, n4 and n8 each independently represent an integer of 0 to 3, and n2' and n6' each independently represent an integer of 0 to 2. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ ~Ar ８ , R４１ ~R ４４ , m1-m4, n1, n3-n5, n7, n8, A １ , A ２ For details of the formula (1a) and the formula (1b), the corresponding descriptions can be referred to. However, Ar bonded to adjacent carbon atoms １ Ar bonded to adjacent carbon atoms ３ Ar bonded to adjacent carbon atoms ５ Ar bonded to adjacent carbon atoms ７ They may be bonded to each other to form a ring structure, preferably a benzofuran (fused with a furan ring) or a benzothiophene (fused with a thiophene ring).

[0110] Specific examples of compounds represented by general formula (12a) and general formula (12b) are listed below. However, the compounds of general formula (12a) and general formula (12b) that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, the structure of each compound is defined by specifying R, Ar, and X in formulas F1 to F56 in the table. R is selected from A to D listed below, Ar is selected from a to d listed below, and X is selected from α to γ. For example, compound No. 1 in the table is a compound having a structure in which R is A and Ar is a in formula F1.

[0111]

[0112]

[0113] In one embodiment of the present invention, the above skeletons (1a) to (12b) are skeletons to which no other ring is further fused. In another embodiment of the present invention, the above skeletons (1a) to (12b) are skeletons to which another ring may be further fused. The other rings referred to here are those defined by the above R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ The description of the cyclic structure formed by bonding together can be referred to.

[0114] In one embodiment of the present invention, A in general formula (1) １ and A ２ is an acceptor group. For example, A １ and A ２ is an acceptor group, and examples thereof include compounds having any of the skeletons (1a) to (12b). For details and specific examples of the acceptor group, see A in the above general formula (1). １ and A２ The explanation and specific examples of the acceptor group in the above can be referred to. １ and A ２ Specific examples of compounds in which A is an acceptor group are as follows: １ and A ２ The compounds in which A is an acceptor group are not to be construed as being limited by the following specific examples. １ and A ２ have a structure in which both are "A", and the structure of each compound is specified by individually specifying the "A".

[0115] In one embodiment of the present invention, a compound having a rotationally symmetric structure is selected as the compound represented by general formula (1). In one embodiment of the present invention, a compound having an axisymmetric structure is selected as the compound represented by general formula (1). In one embodiment of the present invention, a compound having an asymmetric structure is selected as the compound represented by general formula (1). Specific examples of compounds having an asymmetric skeleton are listed below. Compounds having an asymmetric skeleton or compounds having an asymmetric structure that can be used in the present invention should not be construed as being limited by the specific examples below. Regarding specific examples containing X, compounds in which all Xs in the molecule are oxygen atoms and compounds in which all Xs in the molecule are sulfur atoms are respectively disclosed. Compounds in which some of the Xs in the molecule are oxygen atoms and the rest are sulfur atoms can also be used.

[0116] Specific examples of compounds that have a symmetrical skeleton but have an asymmetrical structure due to asymmetrically bonded substituents are given below. The compounds having an asymmetrical structure that can be used in the present invention should not be construed as being limited by the following specific examples.

[0117] In one embodiment of the present invention, R in general formula (1) ３ is not a diarylamino group (two aryl groups constituting the diarylamino group may be bonded to each other). In a preferred embodiment of the present invention, R ３ is a hydrogen atom, a deuterium atom, or an acceptor group (not a donor group). In one embodiment of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or greater. In a preferred embodiment of the present invention, at least one of m1 and m2 in general formula (1a) is 1 or greater. In a further preferred embodiment of the present invention, at least one of n1 to n4 in general formula (1a) is 1 or greater, and at least one of m1 and m2 in general formula (1a) is 1 or greater. In one embodiment of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or greater. In a preferred embodiment of the present invention, at least one of m3 and m4 in general formula (1b) is 1 or greater. In a further preferred embodiment of the present invention, at least one of n5 to n8 in general formula (1b) is 1 or greater, and at least one of m3 and m4 in general formula (1a) is 1 or greater. When at least one of m1 and m2 is 1 or more, and at least one of m3 and m4 is 1 or more, R ４１ and R ４２ At least one of and R ４３ and R ４４ At least one of R is preferably an alkyl group optionally substituted with a deuterium atom, for example, R ４１ ~R ４４ When at least one of n1 to n4 is 1 or more and at least one of n5 to n8 is 1 or more, Ar １ ~Ar ４ and Ar ５ ~Ar ８ At least one of the groups is preferably an aryl group which may be substituted with a deuterium atom or an alkyl group, for example, Ar １ ~Ar ８ In one embodiment of the present invention, all of X in general formula (1) are aryl groups which may be substituted with a deuterium atom or an alkyl group. １is a boron atom and R ８ , R １０ , R １２ , R １３ , R １５ , R １７ is an alkyl group (or a methyl group), R １ ~R ７ , R １８ ~R ２０ , R ２３ ~R ２６ At least one of X in general formula (1) is a substituent, preferably a group in the substituent group E, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. ２ is a boron atom and R ８ , R １０ , R １２ , R ２２ , R ２４ , R ２６ is an alkyl group (or a methyl group), R １ ~R ７ , R １３ ~R １６ , R １９ ~R ２１ At least one of X in general formula (1) is a substituent, preferably a group in the substituent group E, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. １ is a boron atom, and R ８ and R ９ , R ９ and R １０ and R １５ and R １６ , R １６ and R １７ When any pair of these is bonded to each other to form an aromatic ring (or a benzene ring), R １ ~R ７ , R １８ ~R ２０ , R ２３ ~R ２６ At least one of X in general formula (1) is a substituent, preferably a group in the substituent group E, for example, an aryl group which may be substituted with a deuterium atom or an alkyl group. ２ is a boron atom, and R ８ and R９ , R ９ and R １０ and R ２２ and R ２３ , R ２３ and R ２４ When any pair of these is bonded to each other to form an aromatic ring (or a benzene ring), R １ ~R ７ , R １３ ~R １６ , R １９ ~R ２１ At least one of R in general formula (1) is a substituent, preferably a group of substituent group E, for example, an aryl group optionally substituted with a deuterium atom or an alkyl group. ９ and R １１ is neither a cyano group nor an alkyl group. ９ and R １１ is a hydrogen atom, a deuterium atom, or a substituent other than a cyano group and an alkyl group. ９ and R １１ is neither a cyano group nor a tert-butyl group. ８ ~R １２ In one embodiment of the present invention, at least one of R in general formula (1) is a substituent. ３ is not a substituted amino group or an aryl group. ３ is not a substituted amino group or a phenyl group. ３ is not a dimethylamino group, a diphenylamino group, or a phenyl group. １ ~R ２６ At least one of R is a substituent, and more preferably R １ ~R ２６ At least one of the groups is an alkyl group, for example, an alkyl group having 1 to 4 carbon atoms.

[0118] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by vapor deposition, the molecular weight of the compound represented by general formula (1) is preferably 1,500 or less, more preferably 1,200 or less, even more preferably 1,000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1). It is preferably 624 or more.

[0119] The compound represented by general formula (1) preferably does not contain a metal atom. The metal atom here does not include a boron atom. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, sulfur, and boron. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and boron. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, sulfur, and boron. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and boron. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and boron.

[0120] The compound represented by general formula (1) can be synthesized by combining known reactions, for example, by utilizing a ring-closure reaction or a substitution reaction.

[0121] In this specification, the term "alkyl group" may be linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched moieties may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The alkyl group serving as a substituent may be further substituted with an aryl group. An "alkenyl group" may be linear, branched, or cyclic. It may also contain two or more of the linear, cyclic, and branched moieties. The alkenyl group may have, for example, two or more carbon atoms, or four or more carbon atoms. It may have 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less carbon atoms. Specific examples of alkenyl groups include ethenyl, n-propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, isopentenyl, n-hexenyl, isohexenyl, and 2-ethylhexenyl. The alkenyl group may be further substituted with a substituent. An "aryl group" or a "heteroaryl group" may be a monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and may be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a quinoline ring, a pyrazine ring, a quinoxaline ring, and a naphthyridine ring, and these may be condensed rings.Specific examples of the aryl group or heteroaryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group. The number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected from a range of 6 to 14, or may be selected from a range of 6 to 10. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected from a range of 5 to 14, or may be selected from a range of 5 to 10. The terms "arylene group" and "heteroaryl group" can be understood by replacing the valence of the aryl group and heteroaryl group from 1 to 2.

[0122] In the present specification, "substituent group A" refers to a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton atoms), a heteroaryl It means one group or a group formed by combining two or more groups selected from the group consisting of an arylthio group (for example, having 5 to 30 atoms constituting the ring skeleton), an acyl group (for example, having 1 to 40 carbon atoms), an alkenyl group (for example, having 1 to 40 carbon atoms), an alkynyl group (for example, having 1 to 40 carbon atoms), an alkoxycarbonyl group (for example, having 1 to 40 carbon atoms), an aryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a silyl group (for example, a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group. In the present specification, "substituent group B" refers to one group selected from the group consisting of alkyl groups (e.g., 1 to 40 carbon atoms), alkoxy groups (e.g., 1 to 40 carbon atoms), aryl groups (e.g., 6 to 30 carbon atoms), aryloxy groups (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 ring skeleton atoms), heteroaryloxy groups (e.g., 5 to 30 ring skeleton atoms), and diarylamino groups (e.g., 0 to 20 carbon atoms). In the present specification, "substituent group C" refers to one group selected from the group consisting of alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), heteroaryl groups (e.g., 5 to 20 ring skeleton atoms), and diarylamino groups (e.g., 12 to 20 carbon atoms). As used herein, "substituent group D" means one group or a group formed by combining two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms) and heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms).As used herein, "substituent group E" refers to one group selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms) or a group formed by combining two or more of these groups. In the present specification, when a "substituent" or "substituted or unsubstituted" is used, the substituent may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0123] [Compound represented by general formula (2)] Next, the compound represented by the following general formula (2) will be described.

[0124] In general formula (2), R １１２ and R １１３ One of R represents a cyano group or a substituted or unsubstituted triazinyl group. １１２ is a cyano group. １１３ is a cyano group. １１２ is a substituted or unsubstituted triazinyl group. １１３ is a substituted or unsubstituted triazinyl group. The substituent of the triazinyl group can be a group selected from any of Substituent Groups A to E, but is preferably one or more groups selected from the group consisting of alkyl groups, aryl groups, and heteroaryl groups, and more preferably a group of Substituent Group E. For example, an aryl group which may be substituted with one group selected from the group consisting of alkyl groups and aryl groups, or a group in combination of two or more groups, can be mentioned. For example, an unsubstituted aryl group can be mentioned. The triazinyl group is preferably a 2,4,6-triazinyl group which may be substituted at the 3- and 5-positions, more preferably a 2,4,6-triazinyl group which is substituted at both the 3- and 5-positions, and even more preferably a 2,4,6-triazinyl group which is substituted at both the 3- and 5-positions with substituted or unsubstituted aryl groups.

[0125] In general formula (2), R１１２ and R １１３ (i.e., the one that is not a cyano group or a substituted or unsubstituted triazinyl group) and R １１１ , R １１４ , R １１５ each independently represents a hydrogen atom, a deuterium atom, a donor group containing a substituted amino group, or a substituted or unsubstituted aryl group (excluding donor groups containing a substituted amino group). １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ At least one of the groups is independently a carbazol-9-yl group (the carbazol-9-yl group is at least substituted or further fused with a ring).

[0126] The donor group referred to here means a group having a negative Hammett σp value. In one embodiment of the present invention, the donor group has a σp value of -0.2 or less. In one embodiment of the present invention, the donor group has a σp value of -0.4 or less. The donor group has a σp value of -0.6 or less. The donor group containing a substituted amino group means a group having a substituted amino group within the donor group, and may be a substituted amino group or a group to which a substituted amino group is bonded. A typical donor group containing a substituted amino group has a structure represented by the following general formula (3): General formula (3)

[0127] In general formula (3), R １２１ and R １２２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １２１ and R １２２may be bonded to each other to form a cyclic structure. L represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. The substituent may be a group selected from any of substituent groups A to E, but is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a group selected from substituent group E. When multiple substituents are introduced, they may be the same or different. Furthermore, the substituent that can be introduced into the arylene group or heteroarylene group of L may be a group represented by general formula (3). * represents the bonding position to the carbon atom (C) that constitutes the ring skeleton of the ring in general formula (2).

[0128] The group represented by general formula (3) preferably contains a carbazol-9-yl structure. The carbazol-9-yl structure includes not only a substituted or unsubstituted carbazol-9-yl group (which may be further fused with a ring) but also a group substituted with a substituted or unsubstituted carbazol-9-yl group (which may be further fused with a ring). Two or more carbazol-9-yl structures may be contained. The ring fused to the carbazol-9-yl structure is one ring selected from the group consisting of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, or two or more fused rings. When two or more rings are fused, the rings may be two or more of the same type of ring fused, or two or more different types of ring fused. An example of the former is a naphthalene ring in which two benzene rings are fused, and an example of the latter is a benzofuran ring in which a benzene ring and a furan ring are fused. The fused ring is preferably one ring or two or more fused rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. An example of an aromatic hydrocarbon ring is a benzene ring. The aromatic heterocycle refers to a ring exhibiting aromaticity and containing a heteroatom as a ring skeleton-constituting atom. It is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the aromatic heterocycle. A substituent selected from Substituent Group E is preferably bonded to the nitrogen atom of the pyrrole ring, and more preferably an aryl group optionally substituted with an alkyl group or an aryl group is bonded to the nitrogen atom of the pyrrole ring. A furan ring and a thiophene ring are preferred as the aromatic heterocycle. An example of an aliphatic hydrocarbon ring is a cyclopentadiene ring.

[0129] In one embodiment of the present invention, the ring fused to the carbazol-9-yl structure is selected from one ring or two or more fused rings selected from the group consisting of a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, and a cyclopentadiene ring. In a preferred embodiment of the present invention, the ring is selected from one ring or two or more fused rings selected from the group consisting of a benzene ring, a furan ring, a thiophene ring, and a pyrrole ring. In a further preferred embodiment of the present invention, the ring is selected from one ring or two or more fused rings selected from the group consisting of a benzene ring, a furan ring, and a thiophene ring. In one embodiment of the present invention, the ring fused to the carbazol-9-yl structure is a benzene ring, a naphthalene ring, a benzofuran ring, a benzothiophene ring, or an indole ring. In a preferred embodiment of the present invention, the ring fused to the carbazol-9-yl structure is a benzene ring, a naphthalene ring, a benzofuran ring, or a benzothiophene ring. In a more preferred embodiment of the present invention, the ring fused to the carbazol-9-yl structure is a benzene ring, a benzofuran ring, or a benzothiophene ring. In a particularly preferred embodiment of the present invention, the ring fused to the carbazol-9-yl structure is a benzofuran ring or a benzothiophene ring. The benzofuran ring, benzothiophene ring, indole ring, and indene ring are 5-membered rings fused to the benzene ring constituting the carbazol-9-yl structure. The carbazol-9-yl structure may be fused with one to four rings, preferably one or two rings, and more preferably one ring. When rings are fused with two or more rings, the fused rings may be the same or different, but are preferably the same. Furthermore, the carbazol-9-yl structure to which a ring may be fused may be substituted with a substituent. Such a substituent can be selected, for example, from Substituent Groups A to E, and is preferably selected from Substituent Group E.

[0130] The donor group containing a substituted amino group is preferably a substituted or unsubstituted carbazol-9-yl group (which may further have a fused ring). For the substituted or unsubstituted carbazol-9-yl group (which may further have a fused ring), the above description of the carbazol-9-yl structure and the preferred range thereof can be referred to.

[0131] In general formula (2), R １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ At least one of R is independently a carbazol-9-yl group (here, the carbazol-9-yl group is at least substituted or further fused with a ring). １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ At least one of the donor groups represented by the formula (I) is a carbazol-9-yl group (the carbazol-9-yl group here is at least substituted or further fused with a ring). In one embodiment of the present invention, the carbazol-9-yl group here is substituted but not further fused with a ring. In one embodiment of the present invention, the carbazol-9-yl group here is further fused with a ring but is not substituted. In one embodiment of the present invention, the carbazol-9-yl group here is further fused with a ring and is also substituted. For the cases where the carbazol-9-yl group is substituted and where a further fused ring is present, reference can be made to the corresponding descriptions of the carbazol-9-yl structure above.

[0132] In a preferred embodiment of the present invention, R １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ At least one of the groups has a structure represented by the following general formula (4):

[0133] In the general formula (4), X is O, S, N(R １３４ ) or C(R １３５ ) (R １３６) is preferably O, S or N(R １３４ ), more preferably O or S. In a preferred embodiment of the present invention, X is O. In a preferred embodiment of the present invention, X is S. In addition, in the general formula (4), (R １３３ ) ｎ３ The benzene ring in the upper right corner to which (R １３２ ) ｎ２ The central benzene ring to which R is bonded is connected by a bond via X and a single bond, but the positional relationship between these two bonds is not limited. In the above general formula (4), the bond via X is written at the top and the single bond is written at the bottom, but general formula (4) also includes a structure in which the bond via X is at the bottom and the single bond is at the top. In general formula (4), n1 and n3 each independently represent an integer of 0 to 4, preferably 0 to 2, and more preferably 0 or 1. n2 represents an integer of 0 to 2, and preferably 0 or 1. n1 + n2 + n3 is an integer of 0 to 10, for example, 0 to 4, for example, 0 to 2. In one embodiment of the present invention, n1 is 1 to 4. In one embodiment of the present invention, n2 is 1 or 2. In one embodiment of the present invention, n3 is 1 to 4. In general formula (4), R １３１ ~R １３３ Each independently represents a deuterium atom or a substituent. The substituent can be selected from, for example, substituent groups A to E, and is preferably selected from substituent group E. In general formula (4), R bonded to adjacent ring skeleton carbon atoms １３１ R bonded to adjacent ring skeleton carbon atoms １３２ R bonded to adjacent ring skeleton carbon atoms １３３ may be bonded to each other to form a cyclic structure. For the cyclic structure formed, the description of the ring fused to the carbazol-9-yl structure above can be referred to. In one embodiment of the present invention, R bonded to adjacent carbon atoms constituting the ring skeleton １３１ In one embodiment of the present invention, R bonded to adjacent carbon atoms forming the ring skeleton are bonded to each other to form a cyclic structure, preferably a benzofuro structure or a benzothieno structure. １３３are bonded to each other to form a ring structure, preferably a benzofuro structure or a benzothieno structure. １３１ Comrade, R １３２ Comrade, R １３３ They are not bonded to each other to form a ring structure. １３１ and R １３２ , R １３２ and R １３３ do not bond to each other to form a cyclic structure. * in general formula (4) represents the bonding position to the carbon atom constituting the benzene ring skeleton in general formula (2).

[0134] In the following, R １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ Specific examples of donor groups that can be employed are shown below. However, the donor groups that can be employed in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position. Methyl groups are not shown, so for example, D2 has one methyl group.

[0135]

[0136] D421 to D840 are compounds in which all hydrogen atoms present in the above D1 to D420 have been replaced with deuterium atoms. D841 to D1084 are compounds in which all hydrogen atoms present in the phenyl or alkyl groups that are substituents present in the above D2 to D6, D19 to D42, D49 to D78, D100, D101, D106, D107, D112, D113, D118, D119, D153 to D156, D159 to D323, and D412 to D419 have been replaced with deuterium atoms. In one embodiment of the present invention, the donor groups are selected from the group consisting of D1 to D1084, and at least one donor group is selected from the group consisting of D2 to D1084. In one embodiment of the present invention, at least one donor group is selected from the group consisting of D13 to D78, D84 to D119, and D150 to D420.

[0137] R in general formula (1) １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ may be a substituted or unsubstituted aryl group. However, the substituted or unsubstituted aryl group referred to here excludes donor groups containing a substituted amino group. For the aryl group referred to here, the explanation of the aryl group in general formula (1) can be referred to. In a preferred embodiment of the present invention, the aryl group is a phenyl group. In one embodiment of the present invention, the aryl group is a 1-naphthyl group or a 2-naphthyl group. The substituent of the aryl group can be selected, for example, from any one of substituent groups A to E, and is preferably selected from substituent group E. In the following, R １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５ Specific examples of substituted or unsubstituted aryl groups that can be used are shown below. However, the substituted or unsubstituted aryl groups that can be used in the present invention should not be construed as being limited by these specific examples. Note that in the following specific examples, methyl groups are omitted. For example, Ar4 is substituted with a methyl group, and Ar5 is substituted with an isopropyl group. * indicates a bonding position.

[0138] Ar1 to Ar20 above, in which all hydrogen atoms have been replaced with deuterium atoms, are sequentially disclosed as Ar21 to Ar40. Ar41 to Ar57 are sequentially disclosed as Ar41 to Ar57, in which all hydrogen atoms in the phenyl or alkyl groups that are substituents of Ar4 to Ar20 have been replaced with deuterium atoms. In one aspect of the present invention, the substituted or unsubstituted aryl group is selected from Ar1 to Ar57. In one aspect of the present invention, the substituted or unsubstituted aryl group is selected from Ar1 to Ar3, Ar19 to Ar23, Ar39, Ar40, Ar56, and Ar57. In one aspect of the present invention, the substituted or unsubstituted aryl group is Ar1 or Ar21. In one aspect of the present invention, the substituted or unsubstituted aryl group is selected from Ar1, Ar4 to Ar18, Ar21, Ar24 to Ar38, and Ar41 to Ar55.

[0139] R in general formula (1) １１２ and R １１３ The other one and R １１１ , R １１４ , R １１５preferably has 1 to 4 donor groups, preferably has 0 to 2 substituted or unsubstituted aryl groups, and preferably has 0 to 2 hydrogen atoms or deuterium atoms. In one embodiment of the present invention, there are 4 donor groups. In one embodiment of the present invention, there are 3 donor groups and 1 substituted or unsubstituted aryl group. In one embodiment of the present invention, there are 3 donor groups and 1 hydrogen atom or deuterium atom. In one embodiment of the present invention, there are 2 donor groups and 2 substituted or unsubstituted aryl groups. In one embodiment of the present invention, there are 2 donor groups, 1 substituted or unsubstituted aryl group, and 1 hydrogen atom or deuterium atom. In one embodiment of the present invention, there are 2 donor groups and 2 hydrogen atoms or deuterium atoms. In one embodiment of the present invention, there is 1 donor group, 2 substituted or unsubstituted aryl groups, and 1 hydrogen atom or deuterium atom. In one embodiment of the present invention, there is one donor group, one substituted or unsubstituted aryl group, and two hydrogen atoms or deuterium atoms. In one embodiment of the present invention, there is one donor group and three hydrogen atoms or deuterium atoms. In a preferred embodiment of the present invention, all of the donor groups have a carbazol-9-yl structure. In one embodiment of the present invention, the donor groups include a group that does not contain a carbazol-9-yl structure. In one embodiment of the present invention, there is one carbazol-9-yl group (the carbazol-9-yl group is at least substituted or further fused with a ring) among the donor groups. In one embodiment of the present invention, when there are two or more donor groups, there are two carbazol-9-yl groups (the carbazol-9-yl group is at least substituted or further fused with a ring). In a preferred embodiment of the present invention, R １１２ is a cyano group or a substituted or unsubstituted triazinyl group, and R １１３ ~R １１５ is a donor group or a substituted or unsubstituted aryl group. １１１ is a hydrogen atom or a deuterium atom. １１４ is a substituted or unsubstituted aryl group. １１３ ~R １１５ is a donor group.

[0140] Specific examples of compounds represented by general formula (2) are listed below. However, compounds represented by general formula (2) that can be employed in the present invention are not limited to these specific examples. In the specific examples below, D represents a deuterium atom, tBu represents a tertiary butyl group, and Ph represents a phenyl group. Methyl groups are omitted. For example, T4 has a methyl group as a substituent.

[0141] When it is intended to use an organic layer containing the compound represented by general formula (2) by forming it into a film by vapor deposition, the molecular weight of the compound represented by general formula (2) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (2).

[0142] It is preferable that the compound represented by general formula (2) does not contain a metal atom. For example, as the compound represented by general formula (2), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected. For example, as the compound represented by general formula (2), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms can be selected. For example, as the compound represented by general formula (2), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms can be selected. For example, as the compound represented by general formula (2), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms can be selected.

[0143] [Film] The film of the present invention is a film containing a compound represented by general formula (1) and a compound represented by general formula (2). The film of the present invention may be composed solely of the compound represented by general formula (1) and the compound represented by general formula (2), or may contain other materials. As the other materials, it is preferable to use a compound whose lowest excited singlet energy is greater than that of the compound represented by general formula (1) or the compound represented by general formula (2). Such compounds can be used as host materials. The film of the present invention may contain two or more compounds represented by general formula (1). The film of the present invention may also contain two or more compounds represented by general formula (2). In some embodiments, the film of the present invention does not contain a metal element. In some embodiments, the film of the present invention can be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, sulfur atoms, and boron atoms. Alternatively, the film of the present invention can be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and boron atoms. The film of the present invention preferably contains a compound represented by general formula (2) in an amount greater than the compound represented by general formula (1). In one aspect of the present invention, when the compound represented by general formula (2) is taken as 100 parts by weight, the content of the compound represented by general formula (1) is 0.1 to 50 parts by weight, preferably 0.5 to 20 parts by weight, for example, 1 to 10 parts by weight. When the film of the present invention contains a host material, when the total amount of the host material, the compound represented by general formula (1), and the compound represented by general formula (2) is taken as 100 parts by weight, the content of the host material is preferably 35 to 99 parts by weight, more preferably 45 to 95 parts by weight, and can be, for example, 50 to 90 parts by weight. The method for producing the film of the present invention is not particularly limited. In one embodiment, the film of the present invention can be formed by a wet process. In the wet process, a solution in which a composition containing the compound of the present invention is dissolved is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing.In a wet process, an appropriate organic solvent capable of dissolving a composition containing a compound of general formula (1) and a compound of general formula (2) is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in an organic solvent can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited to this. When a vacuum deposition method is used, the compounds constituting the film may be co-deposited from separate deposition sources, or from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder containing compound powders may be used, a compression molded body obtained by compressing the mixed powder, or a mixture obtained by heating, melting, and cooling each compound may be used. In some embodiments, co-deposition is performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are identical or nearly identical, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film having a desired composition ratio can be easily formed by using a deposition source containing a mixture of multiple compounds in the same composition ratio as the composition ratio of the film to be formed. In some embodiments, the temperature at which each compound to be co-deposited exhibits the same weight loss rate can be determined, and this temperature can be used as the co-deposition temperature. The thickness of the film of the present invention can be appropriately determined depending on the application. For example, when used for light emission, the thickness can be within the range of 0.5 to 100 μm. The film of the present invention exhibits high orientation of the constituent materials, particularly the compound represented by general formula (1). The compound represented by general formula (1) has the advantage of being horizontally oriented on the film surface, resulting in high luminous efficiency. Orientation can be evaluated by the orientation value (S value). A larger negative value (a smaller numerical value) indicates higher orientation. The orientation value (S value) is calculated as follows: The orientation value of the compound represented by general formula (1) in the film of the present invention can be determined by the method described in JP-A-2004-24405. The orientation value of the compound represented by general formula (1) in the film of the present invention is preferably −0.35 or less, more preferably −0.38 or less, and even more preferably −0.41 or less. In some embodiments, the film of the present invention emits delayed fluorescence. In some embodiments of the present disclosure, the film of the present invention can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region when excited by thermal or electronic means.

[0144] When a host material is used in the present invention, it is preferable to select the host material from organic compounds having hole transporting and electron transporting functions. In some embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material of the light-emitting layer is an organic compound having a high glass transition temperature. In some embodiments, the host material is selected from the group consisting of: However, the host materials that can be used in the present invention should not be construed as being limited by the specific examples below.

[0145] In addition, a host material represented by the following general formula can also be preferably used. In the above general formula, R' represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. For example, it can be one group selected from the group consisting of a phenyl group, a pyridyl group, a dibenzofuryl group, and a dibenzothienyl group, or a group combining two or more groups. q represents an integer of 1 to 5, preferably 1 or 2, and more preferably 1. Specific examples of compounds represented by the above general formula are shown below.

[0146] In addition, a host material represented by the following general formula can also be preferably used.

[0147] In the above general formula, R １４１ ~R １４７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R １４１ ~R １４７ At least one of R is a substituted or unsubstituted aryl group. Q represents a substituted or unsubstituted 12H-benzofurocarbazol-12-ylphenyl group. In one embodiment of the present invention, R １４１ ~R １４７ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. １４１ ~R １４７ are each independently a hydrogen atom, a deuterium atom, or an aryl group which may be substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group formed by combining two or more of these. １４１ ~R １４７ In a preferred embodiment of the present invention, only one of R is an aryl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group formed by combining two or more of these, and the remaining groups are each independently a hydrogen atom or a deuterium atom. １４１ ~R １４７ is selected from P1 to P14 shown below. In one embodiment of the present invention, Q is a 12H-benzofurocarbazol-12-ylphenyl group optionally substituted with one atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group formed by combining two or more of these. In one embodiment of the present invention, Q is an unsubstituted 12H-benzofurocarbazol-12-ylphenyl group. In a preferred embodiment of the present invention, Q is selected from Q1 to Q18 shown below. Specific examples of compounds represented by the above general formula are shown below in tabular form. In Table 1, Q and R of each compound are １４１ ~R １４７ For example, compound 141-1-1 has Q1, R １４１ is P1 and R １４２ ~R １４７is a hydrogen atom, and compound 141-1-2 is a compound in which Q is Q1 and R １４１ is P2 and R １４２ ~R １４７ In each row of Table 2, 14 structures are collectively specified in one row. For example, in the row "141-1-1 to 141-1-14" in Table 2, Q is Q1, R １４１ are P1 to P14, and R １４２ ~R １４７ The compounds in which R is a hydrogen atom are collectively identified as Compounds 141-1-1 to 141-1-14, in that order. The structures of Compounds 141-1-1 to 141-1-14 collectively shown here correspond to the structures of Compounds 141-1-1 to 141-1-14 identified in Table 1. In the "141-2-1 to 141-2-14" row in Table 2, Q is Q2 and R １４１ are P1 to P14, and R １４２ ~R １４７ is a hydrogen atom are collectively identified as Compounds 141-2-1 to 141-2-14, in that order. The structures of the compounds in the following rows are identified in the same manner. Each compound identified in Table 2 is considered to be individually disclosed in the present specification.

[0148]

[0149]

[0150] [Organic Light-Emitting Device] The organic light-emitting device of the present invention is an organic light-emitting device using a compound represented by general formula (1) and a compound represented by general formula (2). In one embodiment, the organic light-emitting device includes an emitting layer. In one embodiment, the emitting layer includes the compound represented by general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (2) assists the light emission of the emitting material represented by general formula (1) included in the emitting layer (as a so-called assist dopant). In one embodiment, the emitting layer is the film of the present invention described above. In one embodiment, the organic photoluminescence device includes at least one emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least an emitting layer. In one embodiment, the organic layer includes only an emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the emitting layer. Examples of the organic layer 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, and an exciton blocking layer. In some embodiments, 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.

[0151] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0152] Substrate: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0153] Anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and ZnO. In some embodiments, IDIXO (In ２ O ３ An amorphous material capable of forming a transparent conductive film, such as ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly accurate (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as a printing method or a coating method is used. In some embodiments, when emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0154] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ２ O３ In some embodiments, a mixture of an electron-injecting metal and a second metal is used, the second metal being a stable metal having a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming an electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semitransparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semitransparent.

[0155] Injection Layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials:

[0156]

[0157] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0158] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functions of an electron blocking layer and an exciton blocking layer.

[0159] Hole Blocking Layer: The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer may be the same materials as those described above for the electron transporting layer. Examples of preferred compounds that can be used for the hole blocking layer are listed below.

[0160]

[0161] Electron Blocking Layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer may be the same materials as those described above for the hole transport layer. Examples of compounds that can be used as electron blocking materials include compounds represented by the following general formula: In the above general formula, Ar １１ ~Ar １３each independently represents a substituted or unsubstituted aryl group. Examples include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalen-1-yl group, and a substituted or unsubstituted naphthalen-2-yl group. Examples of substituents for hydrogen atoms in aryl groups include a deuterium atom, an alkyl group, and an aryl group, or a combination of two or more atoms or groups selected from the group consisting of aryl groups. Examples of substituted aryl groups include a 4-biphenylyl group, a 3-biphenylyl group, and an m-terphenyl-5'-yl group. Specific examples of compounds represented by the above general formula are shown below.

[0162] Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0163] Exciton Blocking Layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0164] Hole Transport Layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the following properties: hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0165]

[0166] Electron Transport Layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0167]

[0168] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0169]

[0170] Although specific examples of preferred materials that can be used in organic electroluminescence devices have been given, the materials that can be used in the present invention should not be construed as being limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be diverted to be used as materials having other functions.

[0171] Devices: In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0172] Bulb or Lamp: In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0173] Displays or Screens: In some embodiments, the light-emitting layers of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition on the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles in pixel regions protects etching in certain areas until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas experience similar etching rates, but their depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within a pixel, enabling the deep, localized etching required to create steep vertical bevel angles. A preferred material for the deposition mask is Invar. Invar is a metal alloy cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable, low-cost method for creating open areas in a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0174] Device Manufacturing Method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0175] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

[0176] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film, like the organic film formed on the edge of the barrier layer, is formed of polyimide or acrylic. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.

[0177] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0178] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0179] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on and cover the TFT layer. At the same time as the planarization film, made of, for example, polyimide or acrylic, is formed, the grooves at the interface are covered with an organic film, made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impact that occurs. That is, if all barrier layers were completely exposed without the organic film, the impact would be transmitted to the barrier layer when each cell panel is cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impact that would otherwise be transmitted to the barrier layer, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining portion of the organic film, so the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.

[0180] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

[0181] The features of the present invention will be explained in more detail below with reference to synthesis examples and working examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K., C4334 model). The orientation value was measured using a molecular orientation characteristic measuring device (Hamamatsu Photonics K.K., C14234-01).

[0182] (Synthesis Example 1) Synthesis of Compound 1

[0183] Under a nitrogen stream, carbazole (7.69 g, 46.0 mmol) was added to an N,N-dimethylformamide solution (160 mL) of sodium hydride (1.16 g, 29.0 mmol), and the mixture was stirred at room temperature for 30 minutes. 2,5-dibromo-1,4-difluorobenzene (5.00 g, 18.4 mmol) was then added, and the mixture was stirred at 60°C for 16 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. The solid was purified by silica gel column chromatography (toluene), and the resulting solid was washed with acetonitrile to obtain intermediate A (5.83 g, 10.3 mmol, yield 56%) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 8.19 (d, J = 8.0 Hz, 4H), 8.01 (s, 2H), 7.58-7.48 (m, 4H), 7.39-7.35 (m, 4H), 7.27-7.24 (m, 4H) MS (ASAP): 567.01 (M+H + ). Calcd for. C 30 H 18 Br2N2: 565.98

[0184]

[0185] Under a nitrogen stream, n-butyllithium (1.6 mol / L hexane solution, 4.5 mL, 7.19 mmol) was added to a toluene solution (100 mL) of intermediate A (1.00 g, 1.80 mmol) at -30°C, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to -30°C, and boron tribromide (0.991 g, 3.96 mmol) was added, followed by stirring at room temperature for 30 minutes. 1,2,2,6,6-pentamethylpiperidine (0.558 g, 3.60 mmol) was added to the reaction mixture, and the mixture was stirred at 120°C for 17 hours. The reaction mixture was cooled to room temperature, and 2-mesitylmagnesium bromide (1.0 mol / L tetrahydrofuran solution, 5.4 mL, 5.40 mmol) was added, followed by stirring at room temperature for 2.5 hours. The solvent from the resulting reaction mixture was evaporated, methanol was added, and the precipitate was filtered. This solid was purified by silica gel column chromatography (toluene:hexane=4:6) to obtain Compound 1 (0.258 g, 0.388 mmol, yield 22%) as an orange solid. 1 HNMR (400 MHz, CDCl3, δ): 9.26 (s, 2H), 8.52 (d, J= 6.8 Hz, 2H), 8.28-8.21 (m, 4H), 7.94-7.90 (m, 2H), 7.64-7.60 (m, 2H), 7.45-7.42 (m, 4H), 7.15-7.14 (m, 4H), 2.56 (s, 6H), 2.16 (s, 12H) MS (ASAP): 664.23 (M + ). Calcd for. C 48 H 38 B2N2: 664.32

[0186] (Synthesis Example 2) Synthesis of Compound 2

[0187] Under a nitrogen stream, 3,6-diphenylcarbazole (3.00 g, 9.39 mmol) was added to a solution of sodium hydride (0.376 g, 9.39 mmol) in N,N-dimethylformamide (70 mL) and stirred at room temperature for 30 minutes. 2,5-dibromo-1,4-difluorobenzene (1.02 g, 3.76 mmol) was then added and stirred at 60°C for 14 hours. The mixture was returned to room temperature, and water and methanol were added. The precipitated solid was filtered. The solid was dissolved in hot toluene and filtered through a silica gel pad (toluene), and the solvent in the filtrate was distilled off. The resulting solid was washed with acetonitrile to obtain Intermediate B (2.36 g, 2.71 mmol, yield 72%) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 8.46-8.44 (m, 4H), 8.10 (s, 2H), 7.79-7.75 (m, 12H), 7.54-7.49 (m, 8H), 7.41-7.35 (m, 8H) MS (ASAP): 870.20 (M + ). Calcd for. C 54 H 34 Br2N2: 870.11

[0188]

[0189] Under a nitrogen stream, n-butyllithium (1.6 mol / L hexane solution, 2.9 mL, 4.60 mmol) was added to a toluene solution (300 mL) of intermediate B (1.00 g, 1.15 mmol) at -30°C, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to -30°C, and boron tribromide (0.633 g, 2.53 mmol) was added, followed by stirring at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (0.357 g, 2.30 mmol) was added to the reaction mixture, and the mixture was stirred at 120°C for 17 hours. The reaction mixture was cooled to room temperature, and 2-mesitylmagnesium bromide (1.0 mol / L tetrahydrofuran solution, 3.4 mL, 3.40 mmol) was added, followed by stirring at room temperature for 4 hours. The resulting reaction mixture was filtered through a silica pad (toluene), and the solvent from the filtrate was evaporated. Ethyl acetate was added to the resulting viscous mass, and the precipitate was filtered to obtain Compound 2 (0.0710 g, 0.0732 mmol, yield 6%) as an orange solid. 1HNMR (400 MHz, CDCl3, δ): 9.29 (s, 2H), 8.81-8.79 (m, 2H), 8.53-8.52 (m, 2H), 8.46-8.45 (m, 2H), 7.82-7.78 (m, 8H), 7.59-7.36 (m, 14H), 7.20-7.18 (m, 4H), 2.59 (s, 6H), 2.22 (s, 12H) MS (ASAP): 968.67 (M + ). Calcd for. C 72 H 54 B2N2: 968.45

[0190] (Synthesis Example 3) Synthesis of Compound 3

[0191] Intermediate C Under a nitrogen stream, an N,N-dimethylformamide solution (360 mL) of 3,6-di-tert-butyl-9H-carbazole (29.2 g, 105 mmol), cesium carbonate (61.9 g, 190 mmol), and 2,5-dibromo-1,4-difluorobenzene (12.9 g, 47.5 mmol) was stirred at 120°C for 17 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. This was purified by silica gel column chromatography (toluene), and the obtained solid was recrystallized from toluene / methanol to obtain Intermediate C (17.5 g, 22.1 mmol, yield 47%) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 8.2-8.17 (m, 4H), 7.93 (s, 2H), 7.55-7.52 (m, 4H), 7.17 (d, J = 8.4 Hz, 4H), 1.49 (s, 36H) MS (ASAP): 791.47 (M+H + ). Calcd for. C 46 H 50 Br2N2: 790.23

[0192]

[0193] Compound 3: Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 4.7 mL, 7.56 mmol) was added to a toluene solution (100 mL) of intermediate C (2.00 g, 2.52 mmol) at -30°C, and the mixture was stirred at 50°C for 30 minutes. The reaction mixture was cooled to -30°C, and boron tribromide (3.16 g, 12.6 mmol) was added, followed by stirring at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (1.96 g, 12.6 mmol) was added to the reaction mixture, and the mixture was stirred at 130°C for 2 hours. 2-Mesitylmagnesium bromide (1.0 mol / L tetrahydrofuran solution, 25.2 mL, 25.2 mmol) was added to the reaction mixture, and the mixture was stirred for 17 hours while returning to room temperature. The solvent from the resulting reaction mixture was evaporated, methanol was added, and the precipitate was filtered. This solid was purified by silica gel column chromatography (toluene:hexane=1:9) to obtain Compound 3 (0.292 g, 0.328 mmol, yield 13%) as an orange solid. 1 HNMR (400 MHz, CDCl3, δ): 9.11 (s, 2H), 8.58 (d, J= 2.0 Hz, 2H), 8.25 (d, J = 2.0 Hz, 2H), 8.23 ​​(d, J = 1.6 Hz, 2H), 7.75 (d, J = 9.2 Hz, MS (ASAP): 888.85 (M) + ). Calcd for. C 64 H 70 B2N2: 888.57

[0194] (Synthesis Example 4) Synthesis of Compound 4

[0195] Compound 4: Under a nitrogen stream, a solution of compound 3 (250 mg, 0.281 mmol) and N-bromosuccinimide (99.6 mg, 0.562 mmol) in N,N-dimethylformamide (20 mL) is stirred at room temperature for 16 hours. Water is added to this mixture, and the precipitated solid is filtered. This is purified by silica gel column chromatography to obtain compound 4 as an orange solid.

[0196] (Synthesis Example 5) Synthesis of Compound 5

[0197] Compound 5: Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 0.13 mL, 0.201 mmol) was added to a tetrahydrofuran solution (10 mL) of compound 4 (100 mg, 0.0955 mmol) at -30°C, and the mixture was stirred at room temperature for 30 minutes. Dimethylmalononitrile (27.0 mg, 0.287 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 16 hours. The solvent was evaporated from the reaction mixture, and the mixture was purified by silica gel column chromatography to obtain compound 5 as a red solid.

[0198] (Synthesis Example 6) Synthesis of Compound 6

[0199] Compound 6: Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 4.7 mL, 7.56 mmol) was added to a toluene solution (100 mL) of Intermediate C (2.00 g, 2.53 mmol) at 0°C, and the mixture was stirred at 50°C for 30 minutes. The reaction mixture was cooled to 0°C, and boron tribromide (3.16 g, 12.6 mmol) was added, followed by stirring at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (1.96 g, 12.6 mmol) was added to the reaction mixture, and the mixture was stirred at 135°C for 2 hours. 2,4,6-Triisopropylmagnesium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 25.2 mL, 25.2 mmol) was added to the reaction mixture, and the mixture was stirred for 17 hours while returning to room temperature. The solvent from the resulting reaction mixture was evaporated, methanol was added, and the precipitate was filtered. This solid was purified by silica gel column chromatography (toluene:hexane=1:49) and recrystallized from toluene / methanol to obtain Compound 6 (0.140 g, 0.328 mmol, yield 5%) as an orange solid. 1HNMR (400 MHz, CDCl3, δ): 9.10 (s, 2H), 8.53 (d, J=1.6 Hz, 2H), 8.27 (d, J=1.6 Hz, 2H), 8.21 (d, J=1.6 Hz, 2H), 7.64 (d, J=8.8 Hz, 2H), 7.36 (dd, J=8.8, 1.6 Hz, 2H), 7.27 (s, 4H), 3.17 (sept, J=6.8 Hz, 2H), 2.55 (sept, J=6.8 Hz, 4H), 1.55 (d, J=6.8 Hz, 12H), 1.48 (s, 18H), 1.47 (s, 18H), 1.06 (d, MS (MALDI) : 1058.07 (M + ). Calcd for. C 76 H 96 B2N2: 1058.78

[0200] (Synthesis Example 7) Synthesis of Compounds 7 and 8

[0201] Intermediate D: Under a nitrogen stream, an N,N-dimethylformamide solution (50 mL) of 3-tert-butyl-9H-carbazole (1.8 g, 8.06 mmol), potassium carbonate (1.78 g, 12.9 mmol), and 2,5-dibromo-1,4-difluorobenzene (0.876 g, 3.22 mmol) was stirred at 120°C for 17 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. This was purified by silica gel column chromatography (chloroform:hexane=1:4) to obtain Intermediate D (0.44 g, 0.650 mmol, yield 20%) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 8.2-8.18 (m, 4H), 7.97 (s, 2H), 7.56 (d, J = 8.4 Hz, 2H), 7.48 (t, J = 8.4 Hz, 2H), 7.35 (t, J = 8.4 Hz, 2H), 7.25-7.18 (m, 6H), 1.49 (s, 18H) MS (ASAP) : 679.28 (M+H +). Calcd for. C 38 H 34 Br2N2: 678.11

[0202] Compounds 7 and 8: Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 5.23 mL, 8.37 mmol) was added to a toluene solution (100 mL) of intermediate D (1.90 g, 2.79 mmol) at -30°C, and the mixture was stirred at 50°C for 30 minutes. The reaction mixture was cooled to -30°C, and boron tribromide (3.49 g, 14.0 mmol) was added, followed by stirring at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (2.17 g, 14.0 mmol) was added to the reaction mixture, and the mixture was stirred at 135°C for 2 hours. 2-Mesitylmagnesium bromide (1.0 mol / L tetrahydrofuran solution, 27.9 mL, 27.9 mmol) was added to the reaction mixture, and the mixture was stirred for 17 hours while returning to room temperature. The solvent from the resulting reaction mixture was evaporated, methanol was added, and the precipitate was filtered. This solid was purified by silica gel column chromatography (toluene:hexane=1:9) to obtain Compound 7 (0.243 g, 0.313 mmol, yield 11%) and Compound 8 (0.313 g, 0.403 mmol, yield 14%) as orange solids. Compound 7 1 H NMR (400 MHz, CDCl3, δ): 9.21 (s, 2H), 8.52 (dd, J = 9.5, 2.0 Hz, 2H), 8.25 (d, J = 2.0 Hz, 2H), 8.20 (dd, J = 9.5, 2.0 Hz, 2H), 7.81 (d, J = MS (MALDI) : 776.90 (M + ). Calcd for. C 56 H 54 B2N2: 776.45 Compound 8 1H NMR (400 MHz, CDCl3, δ): 9.21 (s, 1H), 9.16 (s, 1H), 8.58 (d, J = 2.0 Hz, 1H), 8.52 (d, J = 7.6 Hz, 1H), 8.3-8.24 (m, 3H), 8.19 (d, J = 7.2 Hz, 1H), 7.92-7.85 (m, 1H), 7.82-7.75 (m, 1H), 7.60 (t, J = 7.2 Hz, 1H), 7.47-7.39 (m, 3H), 7.19-7.13 (m, 4H), 2.6-2.55 (m, 6H), 2.17-2.14 (m, 12H), 1.51 (s, 18H) MS (MALDI) : 776.98 (M + ). Calcd for. C 56 H 54 B2N2: 776.45

[0203] (Synthesis Example 8) Synthesis of Compound 9

[0204] Compound 9: Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 3.3 mL, 5.30 mmol) was added to a toluene solution (100 mL) of Intermediate A (1.00 g, 1.77 mmol) at -30°C, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled to -30°C, and boron tribromide (2.21 g, 8.83 mmol) was added, followed by stirring at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (1.37 g, 8.83 mmol) was added to the reaction mixture, and the mixture was stirred at 120°C for 15 hours. The reaction mixture was returned to room temperature, and 2,4,6-triisopropylmagnesium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 17.7 mL, 17.7 mmol) was added, followed by stirring at 120°C for 4 hours. The resulting reaction mixture was filtered, and the solvent from the filtrate was evaporated. The residue was purified by silica gel column chromatography (toluene:hexane=15:85) to obtain Compound 9 (0.128 g, 0.154 mmol, yield 9%) as an orange solid. 1H NMR (400 MHz, CDCl3, δ): 9.31 (s, 2H), 8.49 (d, J= 7.2 Hz, 2H), 8.28 (d, J = 7.2 Hz, 2H), 8.25 (d, J = 7.6 Hz, 2H), 7.85 (d, J = 8.4 Hz, 2H), 7.61 (t, J = 7.6 Hz, 2H), 7.41 (t, J = 7.6 Hz, 2H), 7.38-7.33 (m, 2H), 7.28 (s, 4H), 3.16 (sept, J = 6.8 Hz, 2H), 2.57 (sept, J = 6.8 Hz, 4H), 1.52 (d, J = 7.2 Hz, MS (MALDI) : 832.73 (M + ). Calcd for. C 60 H 62 B2N2: 832.51

[0205] (Synthesis Example 9) Synthesis of Compound 10

[0206] Intermediate E Under a nitrogen stream, an N,N-dimethylformamide solution (50 mL) of 3-tert-butyl-6-phenyl-9H-carbazole (2.70 g, 9.02 mmol), cesium carbonate (5.34 g, 16.4 mmol), and 2,5-dibromo-1,4-difluorobenzene (1.11 g, 4.10 mmol) was stirred at 120°C for 15 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. This was recrystallized from toluene to obtain Intermediate E (3.06 g, 3.68 mmol, yield 90%) as a white solid. 1HNMR (400 MHz, CDCl3, δ): 8.40 (d, J = 2.0 Hz, 2H), 8.23 ​​(d, J = 1.6 Hz, 2H), 8.02 (s, 2H), 7.79-7.76 (m, 4H), 7.73 (dd, J = 8.8, 1.6 Hz, 2H), 7.59 (dd, J = 8.4, 1.6 Hz, 2H), 7.53-7.48 (m, 4H), 7.41-7.35 (m, 2H), 7.31 (d, J = 7.6 Hz, 2H), 7.23 (d, J = 8.8 Hz, 2H), 1.50 (s, 18H) MS (ASAP) : 831.43 (M+H + ). Calcd for. C 50 H 42 Br2N2: 830.17

[0207] Compound 10: Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 2.27 mL, 3.63 mmol) was added to a toluene solution (100 mL) of intermediate E (1.00 g, 1.21 mmol) at -30°C, and the mixture was stirred at 50°C for 30 minutes. The reaction mixture was cooled to -30°C, and boron tribromide (1.52 g, 6.05 mmol) was added, followed by stirring at room temperature for 30 minutes. 1,2,2,6,6-Pentamethylpiperidine (0.939 g, 6.05 mmol) was added to the reaction mixture, and the mixture was stirred at 135°C for 2 hours. 2,4,6-Triisopropylmagnesium bromide-lithium chloride complex (1.0 mol / L tetrahydrofuran solution, 12.1 mL, 12.1 mmol) was added to the reaction mixture, and the mixture was stirred for 17 hours while returning to room temperature. The solvent from the resulting reaction mixture was distilled off, methanol was added, and the precipitate was filtered. This solid was purified by silica gel column chromatography (toluene:hexane=1:9) and recrystallized from toluene / methanol to obtain Compound 10 (0.364 g, 0.332 mmol, yield 27%) as an orange solid. 1H NMR (400 MHz, CDCl3, δ): 9.24-9.19 (m, 2H), 8.62-8.60 (m, 2H), 8.50-8.47 (m, 2H), 8.35-8.32 (m, 2H), 7.85-7.69 (m, 6H), 7.64-7.60 (m, 2H), 7.56-7.46 (m, 4H), 7.45-7.35 (m, 2H), 7.31 (s, 4H), 3.23-3.16 (m, 2H), 2.65-2.56 (m, 4H), 1.60-1.55 (m, 18H), 1.51-1.48 (m, 12H), 1.14-1.02 (m, 24H) MS (MALDI) : 1098.09 (M+H + ). Calcd for. C 80 H 86 B2N2: 1096.70 The compounds synthesized in the synthesis examples were purified by sublimation before being used for the following purposes.

[0208] (Example 1) Preparation of thin film A thin film was prepared by vacuum deposition on a quartz substrate at a vacuum level of 1×10 －３ Host 1, a delayed fluorescent material shown in Table 3, and a light-emitting material shown in Table 3 were evaporated from different evaporation sources under conditions of less than Pa to form a thin film with a thickness of 100 nm. The contents of Host 1, the delayed fluorescent material, and the light-emitting material were 64.5 mass%, 35.0 mass%, and 0.5 mass%, respectively. The orientation value S of the light-emitting material of the formed thin film was measured, and the results are shown in Table 3.

[0209] (Example 2) Fabrication and Evaluation of Organic Electroluminescence Device Each thin film was formed on a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 100 nm was formed by vacuum deposition at a vacuum degree of 1×10 －５The layers were laminated at 100 Pa. First, HATCN was formed to a thickness of 5 nm on ITO, NPD was formed thereon to a thickness of 60 nm, and EBL1 was further formed to a thickness of 10 nm. Next, Host 1, the delayed fluorescent material listed in Table 3, and the luminescent material listed in Table 3 were co-deposited from different evaporation sources to form a 35 nm thick luminescent layer. The contents of Host 1, the delayed fluorescent material, and the luminescent material were 64.5 mass%, 35.0 mass%, and 0.5 mass%, respectively. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different evaporation sources to form a 30 nm thick layer. The contents of Liq and SF3-TRZ in this layer were 30 mass% and 70 mass%, respectively. Liq was further formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, resulting in an organic electroluminescence device. When a current was applied to each organic electroluminescence element, light emission was observed from all elements. Of the materials contained in the light-emitting layer, the amount of light emitted from the light-emitting material was the largest. ２ The external quantum efficiency (EQE) was measured at 1000 kJ / s, and the results are shown in Table 3. The time taken for the luminous intensity to reach 95% at the start of energization was also measured, and the relative value (LT95) is shown in Table 3, with the time for Comparative Example 1 being taken as 1. The organic electroluminescent elements of the present invention (elements 1 to 3) all exhibited high EQE, had long element life, and were excellent in durability.

[0210]

[0211]

[0212] The film of the present invention exhibits excellent orientation of the light-emitting material and can be suitably used in organic light-emitting devices. Furthermore, the organic light-emitting devices of the present invention have high luminous efficiency, long device life, and excellent durability, and therefore have high industrial applicability.

Claims

1. A compound represented by the following general formula (1) and a compound represented by the following general formula (2) Machine light emitting element. General formula (1) 【Chemistry 1】 [In the general formula (1), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. It is. １ ~R ２６ , A １ and A ２ each independently represents a hydrogen atom, a deuterium atom or a substituted R represents a group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , and R ２５ and R ２６ are bonded together to form a ring structure A 1 and R 12 , A 1 and R 13 , A 2 and R 1 , and A 2 and R 26 may be mutually independent. They do not bond to form a ring structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other to form a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ Nitrogen A nitrogen atom, R ７ and R ８ and R ２１ and R ２２ is bonded via a nitrogen atom to form a six-membered ring. Formation, R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ Few At least one of R is a substituted or unsubstituted aryl group, １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , and R ５ and R ６ are bonded to each other to form an aromatic or heteroaromatic ring. When X 1 is a boron atom and X 2 is a nitrogen atom, the following At least one of conditions 1 and 2 is satisfied. (Requirement 1) R 7 and R 8 , and R 17 and R 18 are bonded to each other to form a cyclic structure containing a boron atom. When the ring structure is a 5- to 7-membered ring, R 7 and R 8, and R 17 and R 18 are bonded to each other to form -B(R 32 )-, -CO-, -CS- or R 32 and R 27 each independently represent a hydrogen atom, a deuterium atom, or Represents an atom or a substituent. (Condition 2) R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 1 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 2 0 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , and R 25 and R 26 1 to 6 of the groups are bonded together to form a benzofuran ring or a benzothiophene ring. ] General formula (2) 【Chemistry 2】 [In the general formula (2), R １１２ and R １１３ One of the groups is a cyano group or a substituted or unsubstituted R represents a substituted triazinyl group. １１２ and R １１３ On the other hand, R １１１ , R １１４ , and R １１５ each independently represents a donor group containing a hydrogen atom, a deuterium atom, or a substituted amino group, or It represents a substituted or unsubstituted aryl group (excluding donor groups including substituted amino groups). S, R １１２ and R １１３ The other one and R １１１ , R １１４ , and R １１５ At least one of Each of the carbazol-9-yl groups is independently a carbazol-9-yl group, At least one of the rings is substituted or further fused.

2. R in general formula (1) ３ and R ６ The organic light-emitting device according to claim 1 , wherein 。

3. R in general formula (1) ８ and R １２ The organic light-emitting device according to claim 1, child.

4. X in formula (1) １ is a nitrogen atom, and X ２ is a boron atom. Machine light emitting element.

5. R in general formula (1) ７ and R ８ , R １７ and R １８ are bonded to each other to form -B(R ３２ ) - Form And R ３２ Each of the formulas in claim 1 independently represents a hydrogen atom, a deuterium atom, or a substituent. The organic light-emitting element is shown.

6. R in general formula (1) ７ and R ８ , R １７ and R １８ are bonded together to form -CO- The organic light-emitting device according to claim 1 .

7. R in general formula (1) ７ and R ８ , R １７ and R １８ are bonded together to form -CS- The organic light-emitting device according to claim 1 .

8. R in general formula (1) ７ and R ８ , R １７ and R １８ are bonded to each other to form -N(R ２７ ) - Form And R ２７ Each of the formulas in claim 1 independently represents a hydrogen atom, a deuterium atom, or a substituent. The organic light-emitting element is shown.

9. R in general formula (1) １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , and R ２５ and R ２６ Of these, 1 to 6 pairs are bonded to each other to form a benzofuran ring or a benzothiophene ring. The organic light-emitting device according to claim 1 ,

10. Any one of claims 1 to 9, wherein the compound represented by formula (1) has a rotationally symmetric structure. The organic light-emitting element according to claim 1.

11. The compound represented by the general formula (1) has any one of the following structures: Machine light emitting element. 【Chemistry 3】 【change】

12. R in the general formula (2) １１２ is a cyano group or a substituted or unsubstituted triazinyl group The organic light-emitting device according to any one of claims 1 to 9.

13. Any one of claims 1 to 9, wherein the donor group of the general formula (2) contains a carbazol-9-yl structure.

10. The organic light-emitting element according to claim 1 .

14. A film containing a compound represented by the following general formula (1) and a compound represented by the following general formula (2): 。 General formula (1) 【Chemistry 4】 [In the general formula (1), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. It is. １ ~R ２６ , A １ and A ２ each independently represents a hydrogen atom, a deuterium atom or a substituted R represents a group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , and R ２５ and R ２６ are bonded together to form a ring structure A 1 and R 12 , A 1 and R 13 , A 2 and R 1 , and A 2 and R 26 may be mutually independent. They do not bond to form a ring structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other to form a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ Nitrogen A nitrogen atom, R ７ and R ８ and R ２１ and R ２２ is bonded via a nitrogen atom to form a six-membered ring. Formation, R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ Few At least one of R is a substituted or unsubstituted aryl group, １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , and R ５ and R ６ Either of these is bonded to an aromatic or heteroaromatic ring. When X 1 is a boron atom and X 2 is a nitrogen atom, the following At least one of conditions 1 and 2 is satisfied. (Requirement 1) R 7 and R 8 , and R 17 and R 18 are bonded to each other to form a cyclic structure containing a boron atom. When the ring structure is a 5- to 7-membered ring, R 7 and R 8, and R 17 and R 18 are bonded to each other to form -B(R 32 )-, -CO-, -CS- or R 32 and R 27 each independently represent a hydrogen atom, a deuterium atom, or Represents an atom or a substituent. (Condition 2) R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 1 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 2 0 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , and R 25 and R 26 1 to 6 of the groups are bonded together to form a benzofuran ring or a benzothiophene ring. ] General formula (2) 【Chemistry 5】 [In the general formula (2), R １１２ and R １１３ One of the groups is a cyano group or a substituted or unsubstituted R represents a substituted triazinyl group. １１２ and R １１３ On the other hand, R １１１ , R １１４ , and R １１５ each independently represents a donor group containing a hydrogen atom, a deuterium atom, or a substituted amino group, or It represents a substituted or unsubstituted aryl group (excluding donor groups including substituted amino groups). S, R １１２ and R １１３ The other one and R １１１ , R １１４ , and R １１５ At least one of Each of the carbazol-9-yl groups is independently a carbazol-9-yl group, At least one of the rings is substituted or further fused.

15. The content of the compound represented by the general formula (1) is higher than that of the compound represented by the general formula (2). The membrane of claim 14, wherein the

16. The compound represented by the general formula (1) and the compound represented by the general formula (2) The film according to claim 14 or 15, further comprising a host material having a high low excited singlet energy. 。

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