Compound, light-emitting material, and organic light-emitting element

Abstract

A compound represented by the following general formula has excellent properties. Ar represents an aromatic ring system having 1-4 rings; Don represents a donor group; Acp represents a group that is neither a deuterium atom nor a donor group; R1 and R2 are each an alkyl group, an aryl group or the like; a represents 0 or more; and b represents 1 or more.

Description

Compound, light-emitting material, and organic light-emitting device

[0001] The present invention relates to a compound having good properties, and also to a light-emitting material using the compound and an organic light-emitting device using the compound.

[0002] Organic light-emitting devices are light-emitting devices that use organic materials, can be manufactured by coating, and do not use rare elements, which has attracted attention in recent years. Organic electroluminescent devices (organic EL devices) in particular have the advantage of being lightweight and flexible because they emit light spontaneously and do not require a backlight. They also have the characteristics of fast response and high visibility, making them promising next-generation light sources. For this reason, active research is being conducted on the development of materials useful for organic light-emitting devices, including organic electroluminescent devices. Research on light-emitting materials, in particular, is being actively conducted (e.g., Non-Patent Document 1). Recently, light-emitting materials have been proposed that have a structure in which a donor group having a fused ring structure is bonded to an acceptor group having a fused ring structure (e.g., Patent Document 1).

[0003] Chem. Soc. Rev.,2017,46,915

[0004] U.S. Patent Publication No. 2022 / 0115600

[0005] On the other hand, there is still room for improvement in the properties of organic light-emitting devices, and further improvements in the properties are required. Therefore, the present inventors have conducted extensive research with the aim of developing a novel compound that contributes to improving the properties of organic light-emitting devices.

[0006] As a result of extensive research, the present inventors have found that compounds in which a group having a characteristic structure is bonded to a specific skeleton are useful compounds for organic light-emitting devices such as organic electroluminescence devices. The present invention has been proposed based on this finding and has the following configuration.

[0007] [1] A compound represented by the following general formula (1): In the general formula (1), Ar represents a monocyclic aromatic ring or an aromatic ring in which 2 to 4 rings are condensed. Don represents a donor group. Acp represents a deuterium atom or a substituent other than a donor group. R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Acp or Don may be bonded to each other to form a cyclic structure, １ and R ２ , R ２ and Acp, R ２ and Don, and Acp and Don do not bond to each other to form a cyclic structure. b is an integer of 1 or more and not more than the maximum substitutable number of the aromatic ring represented by Ar, and a is an integer of 0 or more and not more than the number obtained by subtracting b from the maximum substitutable number of the aromatic ring represented by Ar. When Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom, at least one of the b Don is a donor group containing a nitrogen-atom-shared fused ring structure in which two rings are fused together sharing a nitrogen atom.] [2] A compound represented by the following general formula (1a). General formula (1a) In the general formula (1a), Ar represents a monocyclic aromatic ring or an aromatic ring in which 2 to 4 rings are condensed. D represents a group containing a substituted amino group. R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ３ represents a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, but does not include a substituted amino group. １ and R ３ may be bonded to each other to form a cyclic structure, but R １ and R ２ , R １ and D.R. ２ and R ３ , R ２ and D.R. ３and D do not bond to each other to form a cyclic structure. m is an integer of 1 to 3, and n is an integer of 0 or more and not more than the number obtained by subtracting m from the maximum number of substitutions possible for the aromatic ring represented by Ar. When Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom, at least one of the m Ds is an amino group containing a nitrogen-atom-shared fused ring structure in which two rings are fused together, sharing a nitrogen atom.] [3] The compound according to [1] or [2], wherein at least one of the Dons in [1] is a group represented by the following general formula (2), and at least one of the Ds in [2] is a group represented by the following general formula (2): General formula (2) [In the general formula (2), R ５ ~R １５ each independently represents a hydrogen atom, a deuterium atom or a substituent, or 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 １２ and R １３ , R １３ and R １４ , R １４ and R １５ are bonded to each other to form a ring structure. X represents a single bond, an oxygen atom, or a sulfur atom. * represents a bonding site.] [4] R ５ ~R １５ are each independently a group containing a hydrogen atom, a deuterium atom or a cyano group, or 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 １２ and R １３ , R １３ and R １４ , R１４ and R １５ [5] The compound according to [1] or [2], wherein at least one of the D on in [1] is a group represented by the following general formula (b), and at least one of the Ds in [2] is a group represented by the following general formula (b): [In the general formula (b), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N, Z ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, Z ９ is C-R ２１ or N. １４ ~R ２１ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 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 At least one pair of R may be bonded to each other to form a cyclic structure. * indicates a bonding site.] [6] At least R １７ and R １８[7] The compound according to any one of [2] to [6], wherein Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom. [8] The compound according to any one of [2] to [6], wherein Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom. [9] R １ and R ２ are each independently one group selected from the group consisting of an alkyl group optionally substituted with a deuterium atom or a cyano group, an aryl group optionally substituted with a deuterium atom or a cyano group, and a heteroaryl group optionally substituted with a deuterium atom or a cyano group, or a group formed by linking two or more such groups.

[10] A compound represented by the following general formula (3): General formula (3): [In the general formula (3), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｄ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｄ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.]

[11] A compound represented by the following general formula (18): General formula (18) [In the general formula (18), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｄ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｄ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. X represents a single bond, an oxygen atom, a sulfur atom, or N(RＺ ) and R Ｚ represents a hydrogen atom, a deuterium atom, or a substituent.]

[12] A compound represented by the following general formula (19): General formula (19): [In the general formula (19), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｄ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｄ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. X represents a single bond, an oxygen atom, a sulfur atom, or N(R Ｚ ) and R Ｚ represents a hydrogen atom, a deuterium atom, or a substituent.]

[13] A compound represented by the following general formula (40): General formula (40): [In general formula (40), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｇ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｇeach independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.]

[14] The compound according to any one of [1] to

[13] , which has at least one cyano group.

[15] A light-emitting material comprising the compound according to any one of [1] to

[13] .

[16] An organic light-emitting device comprising the compound according to any one of [1] to

[13] .

[17] The organic light-emitting device according to

[16] , which is an organic electroluminescence device.

[18] The organic light-emitting device according to

[17] , wherein the organic electroluminescence device has a layer containing the compound, and the layer also contains a host material.

[19] The organic light-emitting device according to

[18] , wherein the layer also contains a light-emitting material having a structure outside the scope of general formula (1), in addition to the compound and the host material, and the lowest excited singlet energy of the light-emitting material is lower than that of the host material and lower than that of the compound.

[20] The organic light-emitting element according to

[18] or

[19] , wherein the compound has the largest amount of light emission among materials contained in the organic electroluminescence element.

[21] The organic light-emitting element according to any one of

[16] to

[20] , which emits delayed fluorescence.

[0008] The compound of the present invention has excellent properties and can be used as a light-emitting material. The compound of the present invention can also be used to produce organic light-emitting devices such as organic electroluminescence devices.

[0009] 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 ( ２In 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.

[0010] [Compound Represented by General Formula (1)] The compound of the present invention is a compound represented by the following general formula (1): General Formula (1)

[0011] In general formula (1), Ar represents a monocyclic aromatic ring or an aromatic ring in which 2 to 4 rings are condensed. Don represents a donor group. Acp represents a deuterium atom or a substituent other than a donor group. R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Acp or Don may be bonded to each other to form a cyclic structure, １ and R ２ , R ２ and Acp, R ２ and Don, and Acp and Don do not bond to each other to form a cyclic structure. b is an integer of 1 or more and not more than the maximum substitutable number of the aromatic ring represented by Ar, and n is an integer of 0 or more and not more than the number obtained by subtracting m from the maximum substitutable number of the aromatic ring represented by Ar.

[0012] The donor group that can be used for Don in general formula (1) can be selected from groups with a negative Hammett σp value. 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" and the numerical values ​​of each substituent in the present invention, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991). The donor group that can be represented by D preferably has a σp of -0.3 or less, and may be selected, for example, from the range of -0.5 or less, -0.7 or less, -0.9 or less, or -1.1 or less. For the donor group that can be represented by D, reference can be made to the description and specific examples of the group containing a substituted amino group that can be represented by D in general formula (1a) described below.

[0013] In general formula (1), b is preferably an integer of 1 to 4, and may be, for example, 1 or 2, or may be, for example, 1. Each of the b Don is preferably a group containing a substituted amino group, and is preferably, for example, a group represented by general formula (a) described later, and more preferably a group represented by general formula (b) described later. When Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom, at least one of the b Don is a donor group containing a nitrogen-atom-shared fused ring structure in which two rings are fused together, sharing a nitrogen atom. The nitrogen-atom-shared fused ring structure referred to here is, for example, as in the following structure: １ and Ring A ２means a structure in which the two rings are fused together while sharing a nitrogen atom (N). The two rings may share a nitrogen atom, and the two rings may share a carbon atom in addition to the nitrogen atom. The following structures are examples of structures in which two fused rings share a nitrogen atom and a carbon atom. For example, in the structure on the left, the two fused rings share the nitrogen atom on the left and the carbon atom above it. The hydrogen atoms in these structures may be substituted, and another ring may be fused to this structure. When * is the bonding position, this structure is a donor group and can be Don. Of these, the two structures on the right are preferred because they are diarylamino structures, and the structure on the right is particularly preferred.

[0014] It is particularly preferred that at least one of the b Don in general formula (1) is a group represented by general formula (2) described below. The group represented by general formula (2) is a donor group containing a nitrogen-atom-shared fused ring structure in which two rings are fused together while sharing a nitrogen atom. When b is an integer of 2 or greater, the multiple Dons may be the same or different. In this case, all Dons may be groups represented by general formula (2), or some may be groups represented by general formula (2) and the rest may be donor groups not represented by general formula (2). Specific examples of groups represented by general formula (2) include D1 to D270 described below. Examples of donor groups not represented by general formula (2) include groups represented by general formula (a) described below and groups represented by general formula (b) described below. Specific examples include Z1 to Z1241, Z1(m) to Z1241(m), and Z1(p) to Z1241(p) described below. In general formula (1), the b number of Don may all be groups represented by general formula (a), or may all be groups represented by general formula (b).

[0015] In general formula (1), Acp represents a deuterium atom or a substituent other than a donor group. Acp can be selected from, for example, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group (excluding donor groups). When a is an integer of 2 or more, multiple Acps may be the same or different. R １ and Acp or Don may be bonded to each other to form a cyclic structure. １ and Acp, or R １ and Don may be bonded to each other to form a cyclic structure. １ The cyclic structure that can be formed by bonding Acp or Don to each other may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring whose ring skeleton is composed only of carbon atoms, or a ring formed by condensing these. Aromatic rings and heteroaromatic rings whose ring skeleton is composed only of carbon atoms are preferred. For example, a substituted or unsubstituted benzene ring can be mentioned.

[0016] Ar and R in general formula (1) １ and R ２ The details of Ar and R in general formula (1a) will be described later. １ and R ２ You can refer to the explanation in

[0017] [Compound Represented by General Formula (1a)] The compound of the present invention is preferably a compound represented by the following general formula (1a): General Formula (1a)

[0018] In general formula (1a), Ar represents a monocyclic aromatic ring or an aromatic ring in which 2 to 4 rings are condensed. The aromatic ring referred to here may be an aromatic ring whose ring skeleton is composed only of carbon atoms, or an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom. That is, the aromatic ring that Ar can adopt may be composed only of a ring whose ring skeleton constituent atoms are composed only of carbon atoms, or may include a ring having at least one heteroatom as a ring skeleton constituent atom. The number of rings constituting Ar is preferably 1 to 3, for example, 1, 2, or 3.

[0019] When Ar is an aromatic ring whose ring skeleton is composed only of carbon atoms, each of the rings constituting Ar is a 4- to 7-membered ring, preferably a 5- to 7-membered ring, and may be composed of, for example, a 6-membered ring (i.e., a benzene ring). When Ar is composed of rings whose ring skeleton is composed only of carbon atoms, Ar preferably contains at least one benzene ring. Examples of aromatic rings whose ring skeleton is composed only of carbon atoms that Ar may take include a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a tetracene ring, a chrysene ring, a pyrene ring, and a triphenylene ring. Other examples of aromatic rings whose ring skeleton is composed only of carbon atoms that Ar may take include a pentalene ring, a heptalene ring, a biphenylene ring, an as-indacene ring, an s-indacene ring, an acenaphthylene ring, a fluoranthene ring, an acephenanthrylene ring, an aceanthrylene ring, and a priadene ring. In some embodiments of the present invention, Ar is selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and an anthracene ring. In some embodiments of the present invention, Ar is a benzene ring. In some embodiments of the present invention, Ar is a naphthalene ring. In some embodiments of the present invention, Ar is a phenanthrene ring. Examples of the condensation of Ar with the pyrimidine ring in general formula (1a) include benzo-condensation, naphtho[1,2]-condensation, naphtho[2,3]-condensation, naphtho[3,4]-condensation, phenanthra[1,2]-condensation, phenanthra[2,3]-condensation, phenanthra[3,4]-condensation, phenanthra[5,6]-condensation, phenanthra[6,7]-condensation, phenanthra[7,8]-condensation, phenanthra[9,10]-condensation, anthraceno[1,2]-condensation, anthraceno[2,3]-condensation, and anthraceno[3,4]-condensation. Examples of general formulas specifically showing the aromatic ring of Ar include general formulas (3) to (17) described below. In some embodiments of the present invention, a structure represented by any one of general formulas (3) to (7) and (17), particularly a structure represented by any one of general formulas (3) to (5), (7) and (17), for example, a structure represented by any one of (3) to (5) and (7), is employed. In some embodiments of the present invention, a structure represented by any one of general formulas (6) and (8) to (17), particularly a structure represented by any one of general formulas (8) to (16), is employed.In some embodiments of the present invention, a structure represented by any one of (4) to (17), for example, a structure represented by any one of (6), (8) to (17), is employed.

[0020] When Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom, the heteroatom is preferably one or more selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. In this case, one ring constituting Ar may contain one heteroatom as a ring skeleton-constituting atom, or may contain multiple heteroatoms. When multiple heteroatoms are contained, the heteroatoms may be the same (e.g., both nitrogen atoms) or different (e.g., nitrogen and oxygen atoms, e.g., nitrogen and sulfur atoms). Furthermore, when Ar is an aromatic ring having 2 to 4 condensed rings, only some of the 2 to 4 rings may contain heteroatoms as ring skeleton-constituting atoms, or all of the rings may contain heteroatoms as ring skeleton-constituting atoms. When multiple rings contain heteroatoms as ring skeleton-constituting atoms, the heteroatoms may be the same or different. In some embodiments of the present invention, the heteroatoms constituting the ring skeleton of the aromatic ring of Ar are exclusively oxygen atoms or sulfur atoms. In some embodiments of the present invention, the heteroatoms constituting the ring skeleton of the aromatic ring of Ar are exclusively nitrogen atoms. When Ar is an aromatic ring having 2 to 4 fused rings and the ring skeleton is composed of carbon atoms and at least one heteroatom, it is preferable that Ar contains at least one benzene ring. When Ar is an aromatic ring having 3 fused rings, two of the rings may be benzene rings. When Ar is an aromatic ring having 4 fused rings, two or three of the rings may be benzene rings. In these cases, it is preferable that the ring farthest from the pyrimidine ring in general formula (1a) is a benzene ring. Of the rings constituting Ar, the ring fused with the pyrimidine ring in general formula (1a) may be a benzene ring or a ring containing a heteroatom as a ring skeleton-constituting atom. When Ar is an aromatic ring having a ring skeleton composed of carbon atoms and at least one heteroatom, examples thereof include a furan ring, a thiophene ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring.In some embodiments of the present invention, a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring can be employed. In some embodiments of the present invention, Ar is a benzofuran ring, a benzothiophene ring, or an indole ring, for example, a benzofuran ring, for example, a benzothiophene ring. The benzofuran ring, the benzothiophene ring, and the indole ring are preferably fused to the pyrimidine ring of general formula (1a) via a furan ring, a thiophene ring, and a pyrrole ring, respectively. General formulas (18) to (57) described below can be cited as examples of general formulas specifically showing the aromatic ring of Ar. In some embodiments of the present invention, a structure represented by any one of general formulas (18) to (23), (30) to (39), (42) to (55), or (57) is employed, for example, a structure represented by any one of general formulas (18) or (19), for example, a structure represented by any one of general formulas (20) to (23), (30), or (31), for example, a structure represented by any one of general formulas (32) to (39), (43) to (46), (49) to (55), or (57), for example, a structure represented by any one of (42), (47), (48), or (56). In some embodiments of the present invention, a structure represented by any one of (40), (41), or (56) is employed. In some embodiments of the present invention, a structure in which X is O in general formulas (18) to (57) is employed. In some embodiments of the present invention, a structure in which X is S in general formulas (18) to (57) is employed. In general formulas (18) to (57), X is N-R. ３ In some aspects of the invention, R ３ is a substituted or unsubstituted aryl group. The substituent for the hydrogen atom of the aryl group may be selected from the substituent group A described below, the substituent group B described below, the substituent group C described below, the substituent group D described below, or the substituent group E described below. For example, an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group in which two or more of these are linked together, can be mentioned. In addition, as described below, R ３ is R １may be bonded to form a cyclic structure.

[0021] The aromatic ring represented by Ar in general formula (1a) has m Ds and n Rs in the ring skeleton. ３ When Ar represents an aromatic ring in which 2 to 4 rings are condensed, D and R ３ may be bonded to any of the benzene rings constituting these rings. In addition, m Ds and n Rs may be bonded to only one of the rings. ３ is bonded, and other rings have D and R ３ In this case, for example, m Ds and n Rs may be bonded to a ring whose ring skeleton is composed only of carbon atoms. ３ In addition, for example, m Ds and n Rs may be bonded only to the ring farthest from the pyrimidine ring in general formula (1a). ３ In some other embodiments of the present invention, m D's and n R's may be bonded together. ３ In some preferred embodiments of the present invention, n is 0, and m Ds are bonded to only one ring. In other preferred embodiments of the present invention, n is 0, and m Ds are bonded to only one ring, and the remainder are bonded to another ring. When Ar is a condensed aromatic ring consisting of a ring whose ring skeletal atoms are only carbon atoms and a ring containing a heteroatom as a ring skeletal atom, neither D nor R is present in the ring containing a heteroatom as a ring skeletal atom. ３ It is preferable that m Ds and n Rs are not bonded to each other. ３ In some embodiments of the present invention, when two or more rings each consisting of only carbon atoms are condensed in the aromatic ring represented by Ar, m Ds and n Rs are bonded to only one ring each consisting of only carbon atoms. ３ In some other embodiments of the present invention, m D's and n R's are bonded to each other across multiple rings whose ring skeletons are composed only of carbon atoms. ３ are bonded.

[0022] In general formula (1a), m is an integer of 1 to 3, preferably 1 or 2, and n is 0 or more and is a number obtained by subtracting m from the maximum number of possible substitutions on the aromatic ring represented by Ar. For example, when Ar is a benzene ring and m is 1, n is 3. When m is 2 or 3, two or three Ds may be the same or different. Furthermore, two or three Ds may be bonded to the same ring or different rings. When n is 2, two R ３ may be the same or different. ３ may be bonded to the same ring or different rings. In some preferred embodiments of the present invention, n is 0. For example, m is 1 and n is 0. For example, m is 2 and n is 0.

[0023] D in general formula (1a) is a group containing a substituted amino group. It may be a substituted amino group, or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In some preferred embodiments of the present invention, D in general formula (1a) is a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably 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, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. Here, the two aryl groups constituting the diarylamino group may be bonded to each other, or the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0024] Examples of D in general formula (1a) include a group represented by the following general formula (a).

[0025] In the general formula (a), Z １ is C-R １４ or N, Z ２ is C-R１５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N. Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. １４ and R １５ , R １５ and R １６ , R １６ and R １７ may be bonded to each other to form a cyclic structure. ５ and R １７ may be bonded to each other to form a cyclic structure.

[0026] Z １ ~Z ４ In some embodiments of the present invention, the number of N's is preferably 0 to 3, more preferably 0 to 2. １ ~Z ４ In some aspects of the invention, the number of N's is 1. １ ~Z ４ The number of N is 0. １４ ~R １７ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected, for example, from Substituent Group A described below, Substituent Group B described below, Substituent Group C described below, Substituent Group D described below, or Substituent Group E described below. １４ ~R １７ When two or more of R represent substituents, the two or more substituents may be the same or different. １４ ~R １７ It is preferred that 0 to 2 of these be substituents. For example, one may be a substituent, or none may be a substituent (R １４ ~R １７ may be a hydrogen atom or a deuterium atom). １４ and R １５ , R １５ and R １６, R １６ and R １７ may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic hydrocarbon ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a fused ring of these. An aromatic hydrocarbon ring or a heteroaromatic ring is preferred. An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be fused with another benzene ring or a heterocyclic ring such as a pyridine ring. The heteroaromatic ring refers to a ring exhibiting aromaticity containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be employed. In some embodiments of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. In some preferred embodiments of the present invention, the cyclic structure is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole referred to here may be unsubstituted, or may be substituted with a substituent selected from the below-described Substituent Group A, or may be substituted with a substituent selected from the below-described Substituent Group B, or may be substituted with a substituent selected from the below-described Substituent Group C, or may be substituted with a substituent selected from the below-described Substituent Group D, or may be substituted with a substituent selected from the below-described Substituent Group E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and examples of the substituent include a substituent selected from any of the groups A to E of Substituents. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In some embodiments of the present invention, R １４ and R １５ , R １５ and R １６ , R １６ and R １７ In some embodiments of the present invention, a pair of R １４ and R １５ , R １５ and R １６ , R１６ and R １７ are not bonded to each other to form a ring structure.

[0027] In the general formula (a), Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. ５ is C, and Ar ５ is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. ５ is N, and Ar ５ is a substituted or unsubstituted heteroaromatic ring. ５ An example of the aromatic hydrocarbon ring that can be used is a benzene ring. The benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocycle such as a pyridine ring. ５ The heteroaromatic ring that Z may take is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted. In some embodiments of the present invention, a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring may be adopted as the heteroaromatic ring. In some embodiments of the present invention, Z ５ is C and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline. ５is N, and the heteroaromatic ring is a pyrrole ring of substituted or unsubstituted indole, or an imidazole ring of substituted or unsubstituted benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole referred to here may be unsubstituted, or may be substituted with a substituent selected from the below-described Substituent Group A, may be substituted with a substituent selected from the below-described Substituent Group B, may be substituted with a substituent selected from the below-described Substituent Group C, may be substituted with a substituent selected from the below-described Substituent Group D, or may be substituted with a substituent selected from the below-described Substituent Group E.

[0028] Z in general formula (a) ５ When is C, it is preferably a group represented by the following general formula (b):

[0029] In the general formula (b), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N, Z ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, Z ９ is C-R ２１ or N. 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 At least one pair of R may be bonded to each other to form a ring structure. １４ and R１５ , R １５ and R １６ , R １６ and R １７ Only one pair of R may be bonded to each other to form a ring structure. １４ and R １５ are bonded to each other to form a cyclic structure, and R １６ and R １７ may be bonded to each other to form a cyclic structure. For example, R １６ and R １７ are bonded to each other to form a cyclic structure, and R １７ and R １８ may be bonded to each other to form a cyclic structure, and in this case, the two cyclic structures formed are condensed with each other. １ ~Z ４ , R １４ ~R １７ For Z in general formula (b), the corresponding explanation for general formula (a) can be referred to. ６ ~Z ９ , R １８ ~R ２１ is Z in general formula (a). １ ~Z ４ , R １４ ~R １７ These correspond in order to Z in general formula (a). １ ~Z ４ , R １４ ~R １７ In some aspects of the invention, Z １ ~Z ４ , Z ６ ~Z ９ In some embodiments of the present invention, the number of N's is preferably 0 to 2, and more preferably 0 or 1. １ ~Z ４ , Z ６ ~Z ９ In some preferred embodiments of the present invention, the number of N groups among Z １ ~Z ４ , Z ６ ~Z ９The number of N groups is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0030] D in general formula (1a) is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A described below, or may be substituted with a substituent selected from Substituent Group B described below, or may be substituted with a substituent selected from Substituent Group C described below, or may be substituted with a substituent selected from Substituent Group D described below, or may be substituted with a substituent selected from Substituent Group E described below. Furthermore, one or more rings may be fused to the two benzene rings constituting the carbazol-9-yl group. In some preferred embodiments of the present invention, the carbazol-9-yl group may be substituted with a group selected from Substituent Group E, or may be fused with one or more rings. When a carbazol-9-yl group not fused with a ring is substituted, the substitution position is not particularly limited, but is preferably at least one of the 2- to 7-positions, more preferably at least one of the 3- or 6-positions, and even more preferably the 3- and 6-positions.

[0031] In some embodiments of the present invention, D in general formula (1a) is a carbazol-9-yl group to which one or more rings are fused, and this will be referred to hereinafter as a "ring-fused carbazol-9-yl group." The ring-fused carbazol-9-yl group may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A described below, or Substituent Group B described below, or Substituent Group C described below, or Substituent Group D described below, or Substituent Group E described below. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a substituent selected from Substituent Group E. In some embodiments of the present invention, the ring-fused carbazol-9-yl group is unsubstituted. In some preferred embodiments of the present invention, the ring-fused carbazol-9-yl group is substituted with 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 linking two or more atoms.

[0032] The total number of fused rings in the ring-fused carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In some preferred embodiments of the present invention, the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).

[0033] The ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or may be a ring formed by further condensation of these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferred. Examples of aromatic hydrocarbon rings include substituted or unsubstituted benzene rings. The benzene ring may be fused with another benzene ring or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring may be employed. In some embodiments of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be employed as the aromatic heterocycle. In some embodiments of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from the below-described Substituent Group E (excluding cases where the substituent is only a deuterium atom), and more preferably to an aryl group optionally substituted with an alkyl group or an aryl group. In the present invention, it is preferable to employ a carbazol-9-yl group fused to a ring having one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton-constituting atoms. Of these, a carbazol-9-yl group fused to a benzofuro structure, a carbazol-9-yl group fused to a benzothieno structure, or a carbazol-9-yl group fused to an indolo structure can be preferably employed. In some embodiments of the present invention, the compound has at least one, for example, two or more, carbazol-9-yl groups fused to a benzofuro structure. In some embodiments of the present invention, the benzothieno structure has at least one carbazol-9-yl group fused thereto, for example, two or more.

[0034] Examples of the ring-fused carbazol-9-yl group include a benzofuro[2,3-a]carbazol-9-yl group, a benzofuro[3,2-a]carbazol-9-yl group, a benzofuro[2,3-b]carbazol-9-yl group, a benzofuro[3,2-b]carbazol-9-yl group, a benzofuro[2,3-c]carbazol-9-yl group, and a benzofuro[3,2-c]carbazol-9-yl group. Furthermore, as the ring-fused carbazol-9-yl group, a benzothieno[2,3-a]carbazol-9-yl group, a benzothieno[3,2-a]carbazol-9-yl group, a benzothieno[2,3-b]carbazol-9-yl group, a benzothieno[3,2-b]carbazol-9-yl group, a benzothieno[2,3-c]carbazol-9-yl group, or a benzothieno[3,2-c]carbazol-9-yl group can also be employed. Furthermore, examples of the ring-fused carbazol-9-yl group include an indolo[2,3-a]carbazol-9-yl group, an indolo[3,2-a]carbazol-9-yl group, an indolo[2,3-b]carbazol-9-yl group, an indolo[3,2-b]carbazol-9-yl group, an indolo[2,3-c]carbazol-9-yl group, and an indolo[3,2-c]carbazol-9-yl group.

[0035] When the ring-fused carbazol-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or 2. In some preferred embodiments of the present invention, the ring-fused carbazol-9-yl group is substituted at either the 3- or 6-position. In some preferred embodiments of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In some preferred embodiments of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In some preferred embodiments of the present invention, the ring-fused carbazol-9-yl group has substituents at all of the substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.

[0036] Specific examples of the substituted amino group that can be used for D in general formula (1a) are shown below. However, the substituted amino group 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, Ph represents a phenyl group (C ６ H ５ ) and * indicates the bond position. Methyl groups are not shown, so for example, Z2 has one methyl group. However, deuterated methyl groups are ３ Also, C ６ D ５ represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.

[0037] Z750 to Z1241 are groups in which all hydrogen atoms present in Z1 to Z491 and Z749 have been replaced with deuterium atoms. Phenyl groups in which Z1 to Z1241 are bonded to the 3-position (i.e., groups in which a metaphenylene group is further bonded to the * of Z1 to Z1241) are disclosed as Z1(m) to Z1241(m). Phenyl groups in which Z1 to Z1241 are bonded to the 4-position (i.e., groups in which a paraphenylene group is further bonded to the * of Z1 to Z1241) are disclosed as Z1(p) to Z1241(p). In some preferred embodiments of the present invention, the substituted amino group that can be taken by D in general formula (1a) is selected from the group consisting of Z1 to Z1241. In some embodiments of the present invention, the substituted amino group that can be taken by D is selected from the group consisting of Z460 to Z1241. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z1(m) to Z1241(m). In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z1(p) to Z1241(p). In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z1 to Z13, Z749 to Z761. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z14 to Z16, F762 to Z764. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z17 to Z87, Z765 to Z835. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z88 to Z123, Z836 to Z871. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z124 to Z189 and Z872 to Z937. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z190 to Z363, Z452 to Z491, Z938 to Z1111, and Z1200 to Z1239. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z364 to Z451 and Z1112 to Z1199. In some embodiments of the present invention, the substituted amino group that D may take is selected from Z460 to Z491 and Z1208 to Z1239. In some embodiments of the present invention, the substituted amino group that D may take is selected from the group consisting of Z492 to Z748.

[0038] At least one of the m Ds in general formula (1a) is an amino group containing a nitrogen-atom-shared fused ring structure in which two rings are fused together by sharing a nitrogen atom. For the nitrogen-atom-shared fused ring structure referred to here, the corresponding description of general formula (1) can be referred to. At least one of the m Ds in general formula (1a) is preferably a group containing a structure represented by the following general formula (2). When m in general formula (1a) is 2 or more, it is preferable that at least one of the multiple Ds is a group containing a structure represented by general formula (2). For example, all of the multiple Ds may be groups containing a structure represented by general formula (2). In some embodiments of the present invention, m is 1, and D is a group containing a structure represented by general formula (2), for example, D is a group consisting of a structure represented by general formula (2) (i.e., D is a group represented by general formula (2)). General formula (2)

[0039] In general formula (2), X represents a single bond, an oxygen atom, or a sulfur atom. In some preferred embodiments of the present invention, X is a single bond. In some embodiments of the present invention, X is an oxygen atom or a sulfur atom, for example, an oxygen atom, for example, a sulfur atom. In general formula (2), * represents a bonding site. In general formula (2), R ５ ~R １５ each independently represents a hydrogen atom, a deuterium atom or a substituent, or 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 １２ and R １３ , R １３ and R １４ , R １４ and R １５are bonded to each other to form a cyclic structure. The substituent may be selected, for example, from Substituent Group A described below, Substituent Group B described below, Substituent Group C described below, Substituent Group D described below, or Substituent Group E described below. In some preferred embodiments of the present invention, the substituent is one group selected from the group consisting of an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), and a cyano group, or a group formed by linking two or more groups. For example, the substituent may be a cyano group, or an aryl group optionally substituted with one group selected from the group consisting of a cyano group and an alkyl group, or a group formed by linking two or more groups. R ５ ~R １５ When two or more of R represent substituents, the two or more substituents may be the same or different. ５ ~R １５ Of these, 6 to 11 are preferably hydrogen atoms or deuterium atoms, and for example, 8 to 11 may be hydrogen atoms or deuterium atoms. ５ ~R １５ may all be hydrogen atoms or deuterium atoms. Alternatively, 8 to 10 may be hydrogen atoms or deuterium atoms. For example, 8 may be hydrogen atoms or deuterium atoms, 9 may be hydrogen atoms or deuterium atoms, or 10 may be hydrogen atoms or deuterium atoms. In some preferred embodiments of the present invention, R ５ ~R １５ One to four (more preferably one or two, and even more preferably one) of the above are cyano groups, or aryl groups optionally substituted with one group selected from the group consisting of cyano groups and alkyl groups, or a group formed by linking two or more of these groups together. For example, R ５ , R ６ , R ９ , R １０ , R １３ , R １４ one or more of (preferably R ９ or R １０ , for example, R １０ ) is a cyano group. For example, R ５, R ６ , R ９ , R １０ , R １３ , R １４ one or more of (preferably R ９ or R １０ , for example, R １０ ) is an aryl group optionally substituted with one group selected from the group consisting of a cyano group and an alkyl group, or a group formed by linking two or more groups selected from the group consisting of a cyano group and an alkyl group. 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 １２ and R １３ , R １３ and R １４ , R １４ and R １５may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic hydrocarbon ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring of these. An aromatic hydrocarbon ring or a heteroaromatic ring is preferred. An example of an aromatic hydrocarbon ring is a benzene ring. The heteroaromatic ring refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be employed. In some embodiments of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. In some preferred embodiments of the present invention, the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A described below, or may be substituted with a substituent selected from Substituent Group B described below, or may be substituted with a substituent selected from Substituent Group C described below, or may be substituted with a substituent selected from Substituent Group D described below, or may be substituted with a substituent selected from Substituent Group E described below. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and examples of the substituent include a substituent selected from any of Substituent Groups A to E described below. 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 １２ and R １３ , R １３ and R １４ , R １４ and R １５Among these, it is preferable that 0 to 2 pairs are bonded to each other to form a cyclic structure, and it is more preferable that 0 or 1 pair are bonded to each other to form a cyclic structure. One or two pairs may be bonded to each other to form a cyclic structure. Alternatively, only one pair may be bonded to each other to form a cyclic structure. Alternatively, there may be 0 pairs bonded to each other to form a cyclic structure. D in general formula (1a) may be a group consisting of a structure represented by general formula (2), or may be a group containing a structure represented by general formula (2) as a part thereof. In some preferred embodiments of the present invention, D is a group consisting of a structure represented by general formula (2). When D is a group consisting of a structure represented by general formula (2), * in general formula (2) represents the bonding site to Ar in general formula (1a). When D is a group containing a structure represented by general formula (2) as a part thereof, the structure of general formula (2) is bonded to Ar in general formula (1a) via a linking group. Therefore, * in general formula (2) represents the bonding site to the linking group. The linking group referred to here is preferably a conjugated linking group, and preferred examples thereof include a substituted or unsubstituted arylene group, a substituted or unsubstituted vinylene group (also referred to as an ethenylene group or a 1,2-ethenediyl group), or a group formed by linking these. The substituents of the arylene group and the vinylene group may be a substituent selected from the below-described Substituent Group A, a substituent selected from the below-described Substituent Group B, a substituent selected from the below-described Substituent Group C, a substituent selected from the below-described Substituent Group D, or a substituent selected from the below-described Substituent Group E. For example, an unsubstituted arylene group and a vinylene group are selected. Specific examples include a 1,4-phenylene group, a 1,3-phenylene group, and a vinylene group.

[0040] Among the specific examples of D that can be employed in general formula (1a), specific examples of a group having a structure represented by general formula (2) are shown below. D that can be employed in general formula (1a) may be a group containing the following structure. For example, it may be a phenyl group substituted with a group having the following structure, or a group in which a ring (e.g., a benzene ring) is fused to the benzene ring in the following structure. D that can be employed in the present invention should not be interpreted as being limited by the following specific examples. In the following specific examples, the wavy line indicates the bonding site.

[0041] Groups in which all hydrogen atoms present in D1 to D135 are substituted with deuterium atoms are exemplified here as D136 to D270, in that order. In some embodiments of the present invention, D in general formula (1a) is selected from D1 to D270. In some embodiments of the present invention, D in general formula (1a) is selected from D1 to D135. In some embodiments of the present invention, D in general formula (1a) is selected from D136 to D270. In some embodiments of the present invention, D in general formula (1a) is selected from D1 to D33, D35 to D55, D57 to D77, D79 to D99, D101 to D121, D123 to D134, D136 to D168, D170 to D190, D192 to D212, D214 to D234, D236 to D256, and D258 to D269. In some aspects of the present invention, D in general formula (1a) is selected from D1, D9 to D23, D45, D50, D89, D111, D134 to D136, D144 to D158, D180, D185, D224, D246, D269, and D270. In some aspects of the present invention, D in general formula (1a) is selected from D2 to D8, D24 to D44, D46 to D49, D51 to D88, D90 to D110, D112 to D133, D137 to D143, D159 to D179, D182 to D184, D186 to D223, D225 to D245, and D247 to D268. In some embodiments of the present invention, D in general formula (1a) is selected from D1 to D4, D34, D56, D78, D135 to D139, D169, D191, D213, and D270.

[0042] In general formula (1a), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. The alkyl group, aryl group, and heteroaryl group will be described in detail later. The substituents for the hydrogen atoms of the alkyl group, aryl group, and heteroaryl group may be selected from the substituent group A described later, the substituent group B described later, the substituent group C described later, the substituent group D described later, or the substituent group E described later. In some embodiments of the present invention, R １ and R ２ The alkyl group R may be substituted with one or more atoms or groups selected from the group consisting of deuterium atoms, cyano groups, aryl groups, and heteroaryl groups, for example, with one or more atoms or groups selected from the group consisting of deuterium atoms and cyano groups. １ and R ２ The aryl group represented by R may be substituted with one or more atoms or groups selected from the group consisting of deuterium atoms, cyano groups, alkyl groups, aryl groups, and heteroaryl groups, for example, with one or more atoms or groups selected from the group consisting of deuterium atoms and cyano groups. １ and R ２ The heteroaryl group represented by R may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, a cyano group, an alkyl group, an aryl group, and a heteroaryl group, for example, with one or more atoms or groups selected from the group consisting of a deuterium atom and a cyano group. １ and R ２are each independently one group selected from the group consisting of an alkyl group which may be substituted with a deuterium atom or a cyano group, an aryl group which may be substituted with a deuterium atom or a cyano group, and a heteroaryl group which may be substituted with a deuterium atom or a cyano group, or a group formed by linking two or more such groups. Here, the number of cyano groups substituting the alkyl group, aryl group, or heteroaryl group is preferably 1 to 3, for example, 1, for example, 2. The total number of cyano groups present in general formula (1) is preferably 0 to 4, for example, 0, for example, 1 to 3.

[0043] R １ and R ２ At least one of R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and may also be an acceptor group. The acceptor group here can be selected from groups having a positive Hammett σp value. １ ~R ８ The acceptor group that can be used preferably has a σp of 0.3 or more, and may be selected, for example, from the range of 0.5 or more, 0.7 or more, 0.9 or more, or 1.1 or more.

[0044] R １ and R ２ Preferably, at least one of R is a substituted or unsubstituted aryl group. １ and R ２ At least one of R is a phenyl group optionally substituted with a deuterium atom, for example, R １ and R ２ and R are phenyl groups optionally substituted with deuterium atoms. １ and R ２ At least one of R is a phenyl group (e.g., a cyanophenyl group) that is an acceptor group, for example, R １ and R ２ and R are both phenyl groups that are acceptor groups (e.g., cyanophenyl groups).１ and R ２ At least one of the groups is a substituted or unsubstituted carbazolyl group (limited to those bonded at any of the 1- to 8-positions), such as a substituted or unsubstituted carbazol-1-yl group, a substituted or unsubstituted carbazol-2-yl group, a substituted or unsubstituted carbazol-3-yl group, or a substituted or unsubstituted carbazol-4-yl group. Each carbazolyl group may be further fused with a ring.

[0045] In the following, R １ and R ２ Specific examples of groups that can be used in the present invention are shown below. １ and R ２ The following specific examples should not be construed as limiting. In the following specific examples, * indicates the bonding site. D represents a deuterium atom.

[0046] Groups in which all hydrogen atoms in the groups A9 to A42 have been substituted with deuterium atoms are exemplified here as A43 to A76, in that order.

[0047] R １ and R ２ At least one of R is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and may also be a donor group. The donor group here can be selected from groups with a negative Hammett σp value. １ ~R ８ The donor group R preferably has a σp of −0.3 or less, and may be selected from the range of −0.5 or less, −0.7 or less, −0.9 or less, or −1.1 or less, for example. １ and R ２At least one of may be a group represented by the above general formula (a) or may be a group represented by the above general formula (b). Specific examples include the above Z1 to Z1241, Z1(m) to Z1241(m), and Z1(p) to Z1241(p). R １ and R ２ For details and preferred ranges of the group represented by general formula (a) and the group represented by general formula (b), the corresponding descriptions of general formula (a) and general formula (b) above can be referred to. In some embodiments of the present invention, R １ and R ２ does not include the group represented by the above general formula (2).

[0048] R in general formula (1a) ３ represents a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, but is not a group represented by the above general formula (2). ３ For a description of the alkyl, aryl and heteroaryl groups that R can take, see １ and R ２ Reference may be made to the above discussion of the alkyl, aryl and heteroaryl groups that R may take. In some embodiments of the present invention, ３ is a deuterium atom or an unsubstituted alkyl group. In some aspects of the invention, R ３ is a deuterium atom.

[0049] In general formula (1a), R １ and R ３ may be bonded to each other to form a cyclic structure, but R １ and R ２ , R １ and D.R. ２ and R ３ , R ２ and D.R. ３ and D do not bond to each other to form a cyclic structure. １ and R ３The cyclic structure that can be formed by bonding together may be any of an aromatic hydrocarbon ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring of these. An aromatic hydrocarbon ring or a heteroaromatic ring is preferred. An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring or a heterocyclic ring such as a pyridine ring. The heteroaromatic ring refers to a ring that exhibits aromaticity and contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be employed. In some embodiments of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. In some preferred embodiments of the present invention, the cyclic structure is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole referred to here may be unsubstituted, or may be substituted with a substituent selected from the below-described Substituent Group A, or may be substituted with a substituent selected from the below-described Substituent Group B, or may be substituted with a substituent selected from the below-described Substituent Group C, or may be substituted with a substituent selected from the below-described Substituent Group D, or may be substituted with a substituent selected from the below-described Substituent Group E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and examples of the substituent include a substituent selected from any of the groups A to E of Substituents. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In some embodiments of the present invention, R １ and R ３ In some embodiments of the present invention, a structure represented by the below-described general formula (6) in which R １ and R ３ In some embodiments of the present invention, a structure represented by the below-described general formula (41) in which R １ and R ３ are not bonded to each other to form a ring structure.

[0050] Unless otherwise specified in the present specification, an "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. The "aryl group" and "heteroaryl group" 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 fused rings is preferably 2 to 6, and can 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 fused 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 the range of 6 to 14, or may be selected from the range of 6 to 10. The heteroaryl group preferably has 4 to 40 ring atoms, more preferably 5 to 20 ring atoms, and may have a ring number selected from the range of 5 to 14 ring atoms, or from the range of 5 to 10 ring atoms.

[0051] In the present specification, "Group A" refers to a deuterium atom, 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 atoms constituting the ring skeleton), a heteroaryloxy group (for example, The group consisting of alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups (e.g., having 5 to 30 ring atoms), heteroarylthio groups (e.g., having 5 to 30 ring atoms), heteroarylthio groups (e.g., having 5 to 30 ring atoms), acyl groups (e.g., having 1 to 40 carbon atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), alkynyl groups (e.g., having 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., having 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. The alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups, alkenyl groups, alkynyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, heteroaryloxycarbonyl groups, silyl groups, and nitro groups may be substituted with a deuterium atom constituting group A and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded. As used herein, "Group B" refers to a group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), aryloxy groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring skeleton atoms), heteroaryloxy groups (e.g., having 5 to 30 ring skeleton atoms), and diarylaminoamino groups (e.g., having 0 to 20 carbon atoms). The alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heteroaryl groups, heteroaryloxy groups, and diarylaminoamino groups referred to here may be substituted with the deuterium atoms constituting Group B and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded.As used herein, "Group C" refers to a group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). The alkyl groups, aryl groups, heteroaryl groups, and diarylamino groups referred to here may be substituted with a deuterium atom constituting Group C and a substituent having a structure in which one or more of the above-mentioned substituents are bonded. As used herein, "Group D" refers to a group consisting of deuterium atoms, 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). The alkyl groups, aryl groups, and heteroaryl groups referred to here may be substituted with a deuterium atom constituting Group D and a substituent having a structure in which one or more of the above-mentioned substituents are bonded. As used herein, "Group E" refers to a group consisting of a deuterium atom, alkyl groups (e.g., having 1 to 20 carbon atoms), and aryl groups (e.g., having 6 to 22 carbon atoms). The alkyl group and aryl group referred to here may be substituted with a deuterium atom constituting Group E and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded. In the present specification, when it is described as "substituted or unsubstituted" or "optionally substituted," the substituted deuterium atom or substituent may be selected, for example, from Group A, Group B, Group C, Group D, Group E, or from each of two or more of Groups A to E.

[0052] General formulas (3) to (57) specifying the specific structure of Ar in general formula (1a) are shown below. １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｈeach independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R ａ ~R ｈ In the general formulae (18) to (57), X represents a single bond, an oxygen atom, a sulfur atom, or an N(R Ｚ ) represents. Ｚ represents a hydrogen atom, a deuterium atom, or a substituent, and the substituent here may be selected from the above-mentioned Substituent Group A, or may be selected from the above-mentioned Substituent Group B, or may be selected from the above-mentioned Substituent Group C, or may be selected from the above-mentioned Substituent Group D, or may be selected from the above-mentioned Substituent Group E. For example, an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group in which two or more of these are linked together, can be mentioned. Hereinafter, specific examples of the compound represented by general formula (1a) are listed below, with reference to R in general formulas (3) to (57). １ , R ２ , R ａ ~R ｈ are specified in Tables 1 to 14. However, the compounds represented by general formula (1a) that can be used in the present invention should not be construed as being limited by these specific examples.

[0053] General formula (3)

[0054] In Table 1, R in general formula (3) １ , R ２ , R ａ ~R ｄ In Table 2 below, the R of multiple compounds is shown in each row. １ , R ２ , R ａ ~R ｄ The structures of compounds 1 to 2700 are shown by collectively displaying R １ and R ２ is fixed at A1, and R ｂ~R ｄ is fixed to a hydrogen atom, and R ａ In other words, the column of Compounds 1 to 270 in Table 2 shows all Compounds 1 to 270 specified in Table 1 in one column. Similarly, in the column of Compounds 271 to 540 in Table 2, R １ and R ２ is fixed at A1, and R ａ , R ｃ , R ｄ is fixed to a hydrogen atom, and R ｂ The compounds having the formula D1 to D270 are designated as compounds 271 to 540. Compounds 541 to 2700 in Table 2 are also identified in the same manner.

[0055] In Table 3, R in general formula (4) １ , R ２ , R ａ ~R ｆ The structures of compounds 2701 to 8370 are specified by indicating R in Table 3. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (5) are designated as compounds 8371 to 14040 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (6) are designated as compounds 14041 to 19710, in order.

[0056] In Table 4, R in general formula (7) １ , R ２ , R ａ ~R ｆ The structures of compounds 19711 to 23760 are identified by showing the formula:

[0057] In Table 5, R in general formula (8) １ , R ２ , R ａ ~R ｈThe structures of compounds 23761 to 28350 are specified by indicating R １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (9) are designated as compounds 28351 to 32940 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (10) are designated as compounds 32941 to 37530 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the above to general formula (11) are designated as compounds 37531 to 42120, in this order.

[0058] In Table 6, R in general formula (12) １ , R ２ , R ａ ~R ｈ The structures of compounds 42121 to 46440 are specified by indicating R １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (13) are designated as compounds 46441 to 50760 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (14) are designated as compounds 50761 to 55080 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (15) are designated as compounds 55081 to 59400 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (16) are designated as compounds 59401 to 63720 in order. １ , R ２ , R ａ ~R ｈThe compounds obtained by applying the formula (17) are designated as compounds 63721 to 68040, in this order.

[0059] In Table 7, R in general formula (18) １ , R ２ , R ａ ~R ｄ The structures of compounds 68041 to 76140 are specified by indicating R １ , R ２ , R ａ ~R ｄ The compounds obtained by applying the formula (19) are designated as compounds 76141 to 84240, in order.

[0060] In the tables that follow, "Ph" represents a phenyl group.

[0061] In Table 8, R in general formula (20) １ , R ２ , R ａ ~R ｆ The structures of compounds 84241 to 101250 are specified by indicating R １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (21) are designated as compounds 101251 to 118260 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (22) are designated as compounds 118261 to 135270 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (23) are designated as compounds 135271 to 152280 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (24) are designated as compounds 152281 to 169290 in order. １ , R ２ , R ａ ~R ｆThe compounds obtained by applying the formula (25) are designated as compounds 169291 to 186300 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (26) are designated as compounds 186301 to 203310 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (27) are designated as compounds 203311 to 220320 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (28) are designated as compounds 220321 to 237330 in order. １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (29) are designated as compounds 237331 to 254340, in order.

[0062] In Table 9, R in general formula (30) １ , R ２ , R ａ ~R ｆ The structures of compounds 254341 to 269730 are specified by indicating R １ , R ２ , R ａ ~R ｆ The compounds obtained by applying the formula (21) are designated as compounds 269731 to 285120, in this order.

[0063] In Table 10, R in general formula (32) １ , R ２ , R ａ ~R ｈ The structures of compounds 285121 to 298890 are specified by indicating R １ , R ２ , R ａ ~R ｈThe compounds obtained by applying the formula (33) are designated as compounds 298891 to 312660 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (34) are designated as compounds 312661 to 326430 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (35) are designated as compounds 326431 to 340200 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (36) are designated as compounds 340201 to 353970 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (37) are designated as compounds 353971 to 367740 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (38) are designated as compounds 367741 to 381510 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (39) are designated as compounds 381511 to 395280 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (40) are designated as compounds 395281 to 409050 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (41) are designated as compounds 409051 to 422820 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (42) are designated as compounds 422821 to 436590, in order.

[0064] In Table 11, R in general formula (43) １ , R ２ , R ａ ~R ｈ The structures of compounds 436591 to 449550 are specified by indicating R １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (44) are designated as compounds 449551 to 462510 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (45) are designated as compounds 462511 to 475470 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (46) are designated as compounds 475471 to 488430 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (47) are designated as compounds 488431 to 501390 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (48) are designated as compounds 501391 to 514350, in this order.

[0065] In Table 12, R in general formula (49) １ , R ２ , R ａ ~R ｈ The structures of compounds 514351 to 527850 are specified by indicating R １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (50) are designated as compounds 527851 to 541350 in order. １ , R ２ , R ａ ~Rｈ The compounds obtained by applying the formula (51) are designated as compounds 541351 to 554850 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (52) are designated as compounds 554851 to 568350 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (53) are designated as compounds 568351 to 581850 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (54) are designated as compounds 581851 to 595350 in order. １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (55) are designated as compounds 595351 to 608850, in order.

[0066] In Table 13, R in general formula (56) １ , R ２ , R ａ ~R ｈ The structures of compounds 608851 to 621540 are specified by indicating R １ , R ２ , R ａ ~R ｈ The compounds obtained by applying the formula (57) are designated as compounds 621541 to 634230, in this order.

[0067] The compounds having the structures specified in Tables 2 to 13, in which all "D1 to D270" are replaced with "Z1 to Z270", are designated as compounds 634231 to 1268460, in that order. For example, in the case of compounds 634231 to 634500, R １ and R ２ is fixed at A1, and R ｂ ~R ｄ is fixed to a hydrogen atom, and R ａThe compounds 634231 to 634500 are compounds having a structure in which Don in general formula (1) is a donor group not represented by general formula (2). ａ ~R ｈ Among these, the compounds having the structures specified in the table in which the leftmost "H" is replaced with "Z1" are designated as compounds 1268461 to 1902690 in order. For example, in the case of compounds 1268461 to 1268730, R １ and R ２ is fixed at A1, and R ｂ is fixed at Z1, and R ｃ and R ｄ is fixed to a hydrogen atom, and R ａ The compounds having D1 to D270 are designated, in order, as compounds 1268461 to 1268730. Compounds 1268461 to 1902690 are compounds having a plurality of donor groups with mutually different structures as Don in general formula (1).

[0068] Furthermore, as described in Table 14, １ and R ２ The last eight rows of Table 14 specify compounds in which D1 to D270 present in the compounds are respectively replaced with the corresponding groups beginning with Z. For example, the eighth row from the bottom, "D1 to D270 present in Nos. 1 to 68040 are respectively replaced with Z1 to Z270," specifies compounds in which, for example, if D1 is present in Compounds 1 to 68040, it is replaced with Z1; if D2 is present, it is replaced with Z2; if D3 is present, it is replaced with Z3. For example, if there are multiple D1s in a compound, it specifies a structure in which all of them are replaced with Z1.

[0069] Compounds 1d to 1681946370d are also disclosed in which all hydrogen atoms present in the molecules of Compounds 1 to 1681946370 have been replaced with deuterium atoms. When rotamers exist among the compounds exemplified above, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification.

[0070] Compound group 1 of the present invention includes a compound group represented by general formula (3). Compound group 1 is a compound represented by general formula (2) in which the group R ａ and a compound group 1a in which the group of general formula (2) is R ｂ and a compound group 1b in which the group of general formula (2) is R ｃ and a compound group 1c in which the group of general formula (2) is R ｄ and a compound group 1d in which the group of general formula (2) is R ａ and a compound group 1a′ in which the group of general formula (2) is R ｂ and a compound group 1b' in which the group of general formula (2) is R ｃ and a compound group 1c' in which the group of general formula (2) is R ｄ For each of these compound groups 1a to 1d and 1a' to 1d', embodiments that further satisfy the following additional conditions can be exemplified. In some embodiments of the present invention, the number corresponding to n in general formula (1a) is 0. In some embodiments of the present invention, R １ is an aryl group optionally substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, a cyano group, an alkyl group, an aryl group, and a heteroaryl group. １ and R ２ are each independently an aryl group optionally substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, a cyano group, an alkyl group, an aryl group, and a heteroaryl group. １ and R ２ At least one of R is an aryl group substituted with a cyano group. １ and R ２is an aryl group substituted with a cyano group. In some aspects of the invention, R １ and R ２ In some embodiments of the present invention, at least one of R １ and R ２ is an unsubstituted aryl group. In some aspects of the invention, R ２ is a substituted or unsubstituted diarylamino group. In some embodiments of the present invention, R ２ is a substituted or unsubstituted carbazolyl group (the carbazolyl group may further be fused with a ring). In some embodiments of the present invention, R ２ is a substituted or unsubstituted carbazol-9-yl group (the carbazolyl group may further be fused with a ring). In some embodiments of the present invention, R ２ is a substituted or unsubstituted fused carbazol-9-yl group. １ and R ２ In some aspects of the invention, R １ and R ２ are different from each other.

[0071] Compound group 2 of the present invention includes compounds represented by general formulas (4) to (7). Compound group 2 is a compound represented by general formula (2) where the group is R ａ and a compound group 2a in which the group of general formula (2) is R ｂ and a compound group 2b in which the group of general formula (2) is R ｃ and a compound group 2c in which the group of general formula (2) is R ｄ and a compound group 2d in which the group of general formula (2) is R ｅ and a compound group 2e in which the group of general formula (2) is R ｆ and a compound group 2f in which the group of general formula (2) is R ａ and a compound group 2a′ in which the group of general formula (2) is R ｂ and a compound group 2b' in which the group of general formula (2) is R ｃ and a compound group 2c' in which the group of general formula (2) is R ｄ and a compound group 2d′ in which the group of general formula (2) is Rｅ and a compound group 2e′ in which the group of general formula (2) is R ｆ For each of these compound groups 2a to 2f and 2a' to 2f', there can be exemplified embodiments that further satisfy the additional conditions described for compound groups 1a to 1d and 1a' to 1d'.

[0072] Compound group 3 of the present invention includes compounds represented by general formulas (8) to (17). Compound group 3 is a compound in which the group of general formula (2) is R ａ and a compound group 3a in which the group of general formula (2) is R ｂ and a compound group 3b in which the group of general formula (2) is R ｃ and a compound group 3c in which the group of general formula (2) is R ｄ and a compound group 3d in which the group of general formula (2) is R ｅ and a compound group 3e in which the group of general formula (2) is R ｆ and a compound group 3f in which the group of general formula (2) is R ｇ and a compound group 3g in which the group of general formula (2) is R ｈ and a compound group 3h in which the group of general formula (2) is R ａ and a compound group 3a′ in which the group of general formula (2) is R ｂ and a compound group 3b′ in which the group of general formula (2) is R ｃ and a compound group 3c' in which the group of general formula (2) is R ｄ and a compound group 3d′ in which the group of general formula (2) is R ｅ and a compound group 3e′ in which the group of general formula (2) is R ｆ and a compound group 3f′ in which the group of general formula (2) is R ｇ and a compound group 3g′ in which the group of general formula (2) is R ｈ For each of these compound groups 3a to 3h and 3a' to 3h', there can be exemplified embodiments that further satisfy the additional conditions described for compound groups 1a to 1d and 1a' to 1d'.

[0073] Compound group 4 of the present invention includes compounds represented by general formulas (18) and (19). Compound group 4 is a compound represented by general formula (2) where the group is R ａ and a compound group 4a in which the group of general formula (2) is R ｂ and a compound group 4b in which the group of general formula (2) is R ｃ and a compound group 4c in which the group of general formula (2) is R ｄ and a compound group 4d in which the group of general formula (2) is R ａ and a compound group 4a′ in which the group of general formula (2) is R ｂ and a compound group 4b' in which the group of general formula (2) is R ｃ and a compound group 4c' in which the group of general formula (2) is R ｄ For each of these compound groups 4a to 4d and 4a' to 4d', there can be exemplified embodiments that further satisfy the additional conditions described for compound groups 1a to 1d and 1a' to 1d'.

[0074] Compound group 5 of the present invention includes compounds represented by general formulas (20) to (31). Compound group 5 is a compound represented by general formula (2) where the group is R ａ and a compound group 5a in which the group of general formula (2) is R ｂ and a compound group 5b in which the group of general formula (2) is R ｃ and a compound group 5c in which the group of general formula (2) is R ｄ and a compound group 5d in which the group of general formula (2) is R ｅ and a compound group 5e in which the group of general formula (2) is R ｆ and a compound group 5f in which the group of general formula (2) is R ａ and a compound group 5a' in which the group of general formula (2) is R ｂ and a compound group 5b' in which the group of general formula (2) is R ｃ and a compound group 5c' in which the group of general formula (2) is R ｄ and a compound group 5d′ in which the group of general formula (2) is R ｅ and a compound group 5e′ in which the group of general formula (2) is R ｆFor each of these compound groups 5a to 5f and 5a' to 5f', there can be exemplified embodiments that further satisfy the additional conditions described for compound groups 1a to 1d and 1a' to 1d'.

[0075] Compound group 6 of the present invention includes compounds represented by general formulas (32) to (57). Compound group 6 is a compound represented by general formula (2) where the group is R ａ and a compound group 6a in which the group of general formula (2) is R ｂ and a compound group 6b in which the group of general formula (2) is R ｃ and a compound group 6c in which the group of general formula (2) is R ｄ and a compound group 6d in which the group of general formula (2) is R ｅ and a compound group 6e in which the group of general formula (2) is R ｆ and a compound group 6f in which the group of general formula (2) is R ｇ and a compound group 6g in which the group of general formula (2) is R ｈ and a compound group 6h in which the group of general formula (2) is R ａ and a compound group 6a′ in which the group of general formula (2) is R ｂ and a compound group 6b' in which the group of general formula (2) is R ｃ and a compound group 6c' in which the group of general formula (2) is R ｄ and a compound group 6d′ in which the group of general formula (2) is R ｅ and a compound group 6e′ in which the group of general formula (2) is R ｆ and a compound group 6f′ in which the group of general formula (2) is R ｇ and a compound group 6g′ in which the group of general formula (2) is R ｈ For each of these compound groups 6a to 6h and 6a' to 6h', there can be exemplified embodiments that further satisfy the additional conditions described for compound groups 1a to 1d and 1a' to 1d'.

[0076] In some embodiments of the present invention, the compound represented by general formula (1a) is selected from the following group of compounds:

[0077] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less, when it is intended to use an organic layer containing the compound represented by general formula (1) as a film formed by a vapor deposition method. 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). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. Using a coating method, it is possible to form a film even from compounds with relatively large molecular weights. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also easy to purify to increase its purity.

[0078] Compounds represented by general formula (1), particularly compounds represented by general formula (1a), are useful as light-emitting materials. Therefore, organic light-emitting devices can be manufactured using compounds represented by general formula (1), particularly compounds represented by general formula (1a). Organic light-emitting devices using compounds represented by general formula (1), particularly compounds represented by general formula (1a), are characterized by excellent device durability and long device life. For example, compared to organic light-emitting devices using compounds having a structure in which the pyrimidine ring in general formula (1a) is replaced with a pyrazine ring, organic light-emitting devices using compounds represented by general formula (1a) have the unexpected effect of long device life. Furthermore, organic light-emitting devices using compounds represented by general formula (1), particularly compounds represented by general formula (1a), tend to have low initial driving voltages. Furthermore, compounds represented by general formula (1), particularly compounds represented by general formula (1a), can be effectively used in organic light-emitting devices.

[0079] By applying the present invention, it is also conceivable to use a compound containing multiple structures represented by general formula (1) in its molecule as a light-emitting material. For example, it is conceivable to use a polymer obtained by pre-preparing a polymerizable group in the structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any site of general formula (1) and polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material. Alternatively, it is conceivable to couple compounds having a structure represented by general formula (1) together to obtain a dimer or trimer, and use these as a light-emitting material.

[0080] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas.

[0081] In the above general formula, Q represents a group containing a structure represented by general formula (1), L １ and L ２ represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１ Preferably, X has a structure represented by the formula: １１ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. １０１ , R １０２ , R １０３ and R １０４each independently represents a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L １ and L ２ The linking group represented by the following formula (1) can be bonded to any site of Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0082] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0083] A polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of general formula (1), reacting the hydroxy group as a linker with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group.

[0084] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. Furthermore, the repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may contain two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.

[0085] In some embodiments, the compound represented by general formula (1) is a light-emitting material. Compounds represented by general formula (1) include compounds with long luminescence lifetimes. Compounds represented by general formula (1) can improve the properties of organic light-emitting devices when used in such devices. For example, compounds represented by general formula (1) include compounds that can extend the device lifetime when used in such devices. In some embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. Compounds represented by general formula (1) include compounds with a high proportion of delayed fluorescent components. For example, compounds in which 80% or more of the total emission is the delayed fluorescent component, such as compounds in which 90% or more of the total emission is the delayed fluorescent component, are included. In some embodiments of the present disclosure, the compound represented by general formula (1) 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. In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (eg, 280-400 nm) when excited by thermal or electronic means.In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means.

[0086] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, time-dependent density functional theory using a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional can be used to analyze the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) and screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, donor moieties ("D") can be selected if they have a HOMO energy (e.g., ionization potential) above -6.5 eV, for example. Acceptor moieties ("A") can be selected if they have a LUMO energy (e.g., electron affinity) below -0.5 eV, for example. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly constrain the acceptor and donor moieties into specific configurations. In certain embodiments, compound libraries are screened using one or more of the following properties: 1. Emission near a specific wavelength; 2. Calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ＳＴ ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ＳＴThe quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0087] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) includes a novel compound. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, the compound represented by general formula (1) can be synthesized using a known coupling reaction. Furthermore, the compound represented by general formula (1) can be synthesized using a known ring-closure reaction. Furthermore, the compound represented by general formula (1) can be synthesized using a known substitution reaction. For details of the reaction conditions, please refer to the synthesis examples described below.

[0088] Compositions Using Compounds of Formula (1) In some embodiments, compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, compounds of Formula (1) may be combined with electroactive materials to form a film. In some cases, compounds of Formula (1) may be combined with hole transporting polymers. In some cases, compounds of Formula (1) may be combined with electron transporting polymers. In some cases, compounds of Formula (1) may be combined with hole transporting and electron transporting polymers. In some cases, compounds of Formula (1) may be combined with copolymers having both hole transporting and electron transporting moieties. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0089] [Film Formation] In some embodiments, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing a compound represented by general formula (1) 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 the wet process, an appropriate organic solvent capable of dissolving the composition containing a compound represented by general formula (1) is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing a compound represented by general formula (1) 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 thereto. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or a mixture of the compounds may be co-deposited from a single deposition source. When a single vapor deposition source is used, a mixed powder of compound powders may be used, a compression molded body obtained by compressing the mixed powder may be used, 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 the multiple compounds contained in a single vapor 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 vapor deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed as a vapor deposition source, a film having a desired composition ratio can be easily formed. In some embodiments, the temperature at which each compound to be co-deposited has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[0090] [Application of Compounds Represented by General Formula (1)] By using a compound represented by general formula (1), for example, an organic optical semiconductor device with excellent performance can be fabricated. The organic optical semiconductor device may be an organic light-emitting device that emits light, an organic light-receiving device that receives light, or a device that causes light-induced energy transfer within the device. In some embodiments of the present invention, an organic electroluminescence device can be fabricated using a compound represented by general formula (1). In some embodiments of the present invention, a CMOS (complementary metal oxide semiconductor) can be fabricated using a compound represented by general formula (1). In some embodiments of the present invention, a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1).

[0091] [Organic Light-Emitting Device] The compound represented by general formula (1) is useful as a material for an organic light-emitting device. It is particularly preferably used in organic light-emitting diodes and the like. Organic Light-Emitting Diodes: Some aspects of the present invention relate to the use of a compound represented by general formula (1) of the present invention as an emitting material for an organic light-emitting device. In some embodiments, the compound represented by general formula (1) of the present invention can be effectively used as an emitting material in the emitting layer of an organic light-emitting device. In some embodiments, the compound represented by general formula (1) includes a delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of a compound represented by general formula (1) as a delayed fluorescent material. In some embodiments, the compound represented by general formula (1) can be used as a host material and can be used together with one or more emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF materials (delayed fluorescent materials). In some embodiments, the compound represented by general formula (1) can also be used as a hole-transporting material. In some embodiments, the compound represented by general formula (1) can be used as an electron-transporting material. In some embodiments, the present invention relates to a method for generating delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device comprising the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the emitting layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects or determines the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by general formula (1) improves the light extraction efficiency from the emitting layer. Some aspects of the present invention relate to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emitting layer. In some embodiments, the emitting layer comprises a compound represented by general formula (1) as an emitting material. In some embodiments, 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 (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic light-emitting device includes at least one light-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 light-emitting layer. In one embodiment, the organic layer includes only an light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole-transporting layer, a hole-injecting layer, an electron-blocking layer, a hole-blocking layer, an electron-injecting layer, an electron-transporting 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.

[0092] Emitting Layer: In some embodiments, the emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excited singlet and triplet energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency. In other words, any host material that can achieve high light emission efficiency can be used in the present invention without any particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF material and a host material are used. In some embodiments, the TADF material is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer. In some embodiments, the organic electroluminescent device has a layer containing a compound represented by general formula (1). In some embodiments, the layer also contains a host material.In one embodiment, the layer containing the compound represented by general formula (1) and a host material also contains a delayed fluorescent material having a structure outside the scope of general formula (1), and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound represented by general formula (1). In this case, in one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the compound represented by general formula (1) is maximized. In another embodiment, the organic electroluminescent device has a layer containing the compound represented by general formula (1) and a light-emitting material having a structure outside the scope of general formula (1) (this layer may further contain a host material). In this case, in one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the light-emitting material having a structure outside the scope of general formula (1) is maximized.

[0093] When the compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined. Examples of luminescent materials that can be used in combination with an assist dopant having a structure represented by general formula (1) are listed below.

[0094]

[0095] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be particularly preferably used as light-emitting materials used together with an assist dopant having a structure represented by general formula (1).

[0096] Further preferred light-emitting materials include compounds represented by the following general formula (F1):

[0097] In general formula (F1), R １ , R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. 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 ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４At least one of C-R in general formula (F1) is O or NR, and the remaining one may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be replaced by N.

[0098] In some aspects of the invention, X ２ When is O or NR, R ７ is an acceptor group, or R ６ and R ７ are bonded to each other to form an acceptor group, or R ７ and R ８ In some embodiments of the present invention, X ３ When is O or NR, R １０ is an acceptor group, or R ９ and R １０ are bonded to each other to form an acceptor group, or R １０ and R １１ In some embodiments of the present invention, X ４ When is O or NR, R １５ is an acceptor group, or R １４ and R １５ are bonded to each other to form an acceptor group, or R １５ and R １６ In some embodiments of the present invention, X ２ is NR, R is a substituted or unsubstituted phenyl group, and R ８In some embodiments of the present invention, when X is directly bonded to the carbon atom to which it is attached to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ３ is NR, R is a substituted or unsubstituted phenyl group, and R ９ In some embodiments of the present invention, when X is directly bonded to the carbon atom to which it is attached to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ４ is NR, R is a substituted or unsubstituted phenyl group, and R １６ In some embodiments of the present invention, when X is directly bonded to the carbon atom to which it is attached to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. １ is NR, R is a substituted or unsubstituted phenyl group, and R １ When a carbazole ring is formed by directly bonding to the carbon atom to which is bonded, the 3-position of the carbazole ring is substituted with an acceptor group (where the 3-position is on the phenyl group). In some embodiments of the present invention, the compound is represented by the following general formula (F2):

[0099] In general formula (F2), R １ , R ３ , R ６ ~R １１ , R １４ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R１０ and R １１ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of Ar is O or NR, and the remaining may be O or NR or may not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ Each of C-R in general formula (F2) independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ , C-R ３ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １４ , C-R １５ , C-R １６ may be replaced by N.

[0100] Further preferred light-emitting materials include compounds represented by the following general formula (F3):

[0101] In general formula (F3), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R ２ , R ２ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １ may be bonded to each other to form a cyclic structure. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be replaced by N.

[0102] In some aspects of the invention, R １ and R ２ are each independently a substituted or unsubstituted phenyl group to which other rings may be fused. In some embodiments of the present invention, R ３ and R １０ are each independently a substituted amino group. In some aspects of the invention, R １ and R ３ , and R ２ and R １０ are bonded to each other to form a cyclic structure. In some embodiments of the present invention, the cyclic structure comprises a benzoazaborine ring.

[0103] Further preferred light-emitting materials include compounds represented by the following general formula (F4):

[0104] In formula (F4), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ ~R ９ 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 ７ and R ８ , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ at least one of the rings formed by bonding together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２At least one of the C-R in general formula (F4) has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be replaced by N.

[0105] In some aspects of the invention, Z １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. １ ~R ９ are each independently a substituted or unsubstituted aryl group or an acceptor group, or R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ and R are bonded to each other to form a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. ８ is a substituted or unsubstituted aryl group, or an acceptor group. In some embodiments of the present invention, the compound contains two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.

[0106] Further preferred light-emitting materials include compounds having a ring-fused structure A (in which hydrogen atoms may be substituted with deuterium atoms or substituents) in which a carbon-carbon bond a in the following structure α is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring, or a benzene ring constituting a substituted or unsubstituted dibenzodioxane ring.

[0107] In the structure α, X １ and X ２ each independently represents a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom; Z represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent; Z and X ２ In the fused ring structure A, the structure fused to b and X may be bonded to each other to form a cyclic structure. １ , b and Z, Z and X ２ may be bonded to each other to form a cyclic structure.

[0108] Further preferred light-emitting materials include compounds represented by the following general formula (F5):

[0109] In formula (F5), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R１ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0110] Further preferred light-emitting materials include compounds represented by the following general formula (F6):

[0111] In general formula (F6), X ３ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ ~R ７ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0112] Further preferred light-emitting materials include compounds represented by the following general formula (F7):

[0113] In general formula (F7), X ４ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ａ ~R ７ａ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ａ and R ５ａ , R ５ａ and R ６ａ , R ６ａ and R ７ａ , R ７ａ and R １ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0114] Further preferred light-emitting materials include compounds represented by the following general formula (F8):

[0115] In general formula (F8), Z １represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ８ ~R １４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0116] Further preferred light-emitting materials include compounds represented by the following general formula (F9):

[0117] In formula (F9), Z １ and Z ４ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ and R １５ ~R １７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , Z ４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0118] Further preferred light-emitting materials include compounds represented by the following general formula (F10):

[0119] In general formula (F10), Z １ and Z ５ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ５ , Z ５ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0120] Further preferred light-emitting materials include compounds represented by the following general formula (F11):

[0121] In general formula (F11), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２１ ~R ２７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ 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 , R ２６ and R ２７ may be bonded to each other to form a cyclic structure.

[0122] Further preferred light-emitting materials include compounds represented by the following general formula (F12):

[0123] In general formula (F12), Z １ and Z ６ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２８ ~R ３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２８ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and Z ６ may be bonded to each other to form a cyclic structure.

[0124] Further preferred light-emitting materials include compounds represented by the following general formula (F13):

[0125] In general formula (F13), Z １ and Z ７ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z７ , Z ７ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0126] Further preferred light-emitting materials include compounds represented by the following general formula (F14):

[0127] In general formula (F14), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ３１ ~R ４４ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ３１ and R ３２ , R ３２ and R ３３ , R ３３ and R ３４ , R ３４ and R ３５ , R ３５ and R ３６ , R ３６ and R ３７ , R ３７ and R ３８ , R ３８ and R ３９ , R ３９ and R ４０ , R ４０ and R ４１ , R ４１ and R ４２ , R ４２ and R ４３ , R ４３ and R ４４ may be bonded to each other to form a cyclic structure.

[0128] Further preferred light-emitting materials include compounds represented by the following general formula (F15):

[0129] In general formula (F15), Z １ and Z８ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ５１ ~R ６０ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , R ５１ and R ５２ , R ５２ and R ５３ , R ５３ and R ５４ , R ５４ and R ５５ , R ５５ and R ５６ , R ５６ and R ５７ , R ５７ and R ５８ , R ５８ and R ５９ , R ５９ and R ６０ , R ６０ and Z ８ may be bonded to each other to form a cyclic structure.

[0130] Further preferred light-emitting materials include compounds represented by the following general formula (F16):

[0131] In general formula (F16), Z １ , Z ８ and Z ９ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６１ ~R ６６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , Z ９ and R ６１ , R ６１ and R ６２ , R ６２ and R ６３ , R６３ and R ６４ , R ６４ and R ６５ , R ６５ and R ６６ , R ６６ and Z ８ may be bonded to each other to form a cyclic structure.

[0132] Further preferred light-emitting materials include compounds represented by the following general formula (F17):

[0133] In general formula (F17), Z １ , Z ９ and Z １０ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６７ ~R ６９ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７０ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , Z ９ and R ６７ , R ６７ and R ６８ , R ６８ and R ６９ , R ６９ and Z １０ , Z １０ and R ７０ may be bonded to each other to form a cyclic structure.

[0134] Further preferred light-emitting materials include compounds represented by the following general formula (F18):

[0135] (In general formula (F18), Z １ , Z １１ and Z １２each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７２ ~R ７４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７１ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７１ and Z １１ , Z １１ and R ７２ , R ７２ and R ７３ , R ７３ and Z ７４ , R ７４ and Z １２ may be bonded to each other to form a cyclic structure.

[0136] Further preferred light-emitting materials include compounds represented by the following general formula (F19):

[0137] In general formula (F19), Z １ and Z １１ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７６ ~R ８２ each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R ７５ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７５ and Z １１ , Z １１ and R ７６ , R ７６ and R ７７ , R ７７ and R ７８ , R ７８ and R７９ , R ７９ and R ８０ , R ８０ and R ８１ , R ８１ and R ８２ may be bonded to each other to form a cyclic structure.

[0138] Further preferred light-emitting materials include compounds represented by the following general formula (F20):

[0139] In general formula (F20), X ５ represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded; R １０１ ~R １３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R １０１ and R １０２ , R １０２ and R １０３ , R １０３ and R １０４ , R １０４ and R １０５ , R １０５ and R １０６ , R １０６ and R １０７ , R １０７ and R １０８ , R １０８ and R １０９ , R １０９ and R １１０ , R １１０ and R １１１ , R １１１ and R １１２ , R １１２ and R １１３ , R １１３ and R １１４ , R １１４ and R １１５ , R １１５ and R １１６ , R １１６ and R １１７ , R １１７ and R １１８ , R １１８ and R １１９ , R １１９ and R １２０ , R １２０ and R １２１ , R１２１ and R １２２ , R １２２ and R １２３ , R １２３ and R １２４ , R １２４ and R １２５ , R １２５ and R １２６ , R １２６ and R １２７ , R １２７ and R １２８ , R １２８ and R １２９ , R １２９ and R １３０ , R １３０ and R １０１ may be bonded to each other to form a cyclic structure.

[0140] Further preferred light-emitting materials include compounds represented by the following general formula (F21):

[0141] In general formula (F21), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heteroaromatic ring; R ３ ~R ９ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , R ２ , Z １ and Z ２ At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. １ and Z １ , Z １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and Z ２ , Z ２ and R ２ , R２ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １ may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be replaced by N.

[0142] In some aspects of the invention, R １ and R ２ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring. １ and Z １ are bonded to each other to form a ring structure. In some aspects of the present invention, R １ and Z １ are bonded to each other to form a pyrrole ring.

[0143] Further preferred light-emitting materials include compounds represented by the following general formula (F22):

[0144] In general formula (F22), 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 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.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 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 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 are bonded to each other to form an aromatic hydrocarbon ring or a heteroaromatic ring. For a detailed description of the compound represented by general formula (F22), a preferred range, and specific examples thereof, reference can be made to

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as part of the present specification.

[0145] Further preferred light-emitting materials include compounds represented by the following general formula (F23):

[0146] In general formula (F23), R １ ~R ２２ 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 , R６ and R ７ , R ７ and R, R and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １２ and R １３ , 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, R and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ may be bonded to each other to form a cyclic structure. １ and X ２ Each independently represents O, S, or NR. R represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Compounds encompassed by this general formula include compounds represented by the general formula described in

[0022] of WO2022 / 085714A1, which is incorporated herein by reference, and compounds described in

[0040] to

[0043] and

[0221] , as well as BBCz-R (5) and BBCz-Y-II (6) of J. Am. Chem. Soc. 2020,142,46,19468-19472, which is incorporated herein by reference.

[0147] Further preferred light-emitting materials include compounds represented by the following general formula (F24):

[0148] In general formula (F24), R １ ~R １７ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R２ and R ３ , R ３ and R ４ , 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 １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １ may be bonded to each other to form a cyclic structure. Compounds encompassed by this general formula include BBCz-SB (2), BBCz-G (3), and BBCz-Y (4) described in J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which are incorporated herein by reference.

[0149] Further preferred light-emitting materials include compounds represented by the following general formula (F25):

[0150] In general formula (F25), R １ ~R ２０ 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 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 １１and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ may be bonded to each other to form a cyclic structure. Compounds encompassed by this general formula include BBCz-DB(1) in J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which is incorporated herein by reference.

[0151] Further preferred light-emitting materials include compounds represented by the following general formula (F26):

[0152] In general formula (F26), X １ and X ２ Each independently represents O or S. １ and Y ２ are each independently a single bond, O, S or C(R ａ ) (R ｂ ) represents. １ ~R ２２ , R ａ , R ｂ each independently represents a hydrogen atom, a deuterium atom, or a substituent, and R １ ~R ２２ At least one of R is a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ , R ７ and Y １ , Y １ and R ８ , R ８ and R ９ , R ９ and R１０ , R １０ and R １１ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １６ and R １７ , R １７ and R １８ , R １８ and Y ２ , Y ２ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ may be bonded to each other to form a cyclic structure. ２１ and R １ , R ４ and R ５ , R １０ and R １２ , R １５ and R １６ are not bonded to each other to form a cyclic structure. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ , C-R １７ , C-R １８ , C-R １９ , C-R ２０ , C-R ２１ , C-R ２２ may be replaced by N.

[0153] Specific examples of the compound represented by formula (F26) include the following compounds.

[0154] Further preferred light-emitting materials include compounds containing a BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) structure. For example, a compound represented by the following general formula (F27) is used. General formula (F27)

[0155] In general formula (F27), R １ ~R ９ are each independently a hydrogen atom, a deuterium atom, or a substituent. １ ~R ７ At least one of R is preferably a group represented by the following general formula (F28): ８ and R ９ is preferably a halogen atom.

[0156] In general formula (F28), R １１ ~R １５ each independently represents a hydrogen atom, a deuterium atom or a substituent, and * represents the bonding position.

[0157] Specific examples of light-emitting materials are listed below. In the structural formulas below, t-Bu represents a tertiary butyl group. Derivatives of the following exemplary compounds also include compounds in which at least one hydrogen atom is substituted with a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, or a diarylamino group.

[0158] In some embodiments, when a host material is used, the amount of the compound used in the present invention as the emissive material in the emissive layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 10% by weight or less. In some embodiments, the host material in the emissive layer is an organic compound having hole transport and electron transport functions. In some embodiments, the host material in the emissive layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the emissive layer is an organic compound having a high glass transition temperature.

[0159] In some embodiments, the host material is selected from the group consisting of:

[0160] In some embodiments, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are higher in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. ＳＴis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition within the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the luminescence quantum yield φPL1(A) upon photoexcitation of a co-deposited film of the first TADF molecules and the host material (wherein the concentration of the first TADF molecules in this co-deposited film is A wt %) and the luminescence quantum yield φPL2(A) upon photoexcitation of a co-deposited film of the second TADF molecules and the host material (wherein the concentration of the second TADF molecules in this co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In some embodiments, the luminescence quantum yield φPL2(B) upon photoexcitation of a co-deposited film of the second TADF molecule and the host material (where the concentration of the second TADF molecule in this co-deposited film is B wt %) and the luminescence quantum yield φPL2(100) upon photoexcitation of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the emitting layer may contain three types of TADF molecules with different structures. The compound of general formula (1) may be any of the multiple TADF compounds contained in the emitting layer. In some embodiments, the emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and an emitting material. In some embodiments, the emitting layer does not contain a metal element.In some embodiments, the light-emitting layer can be made of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of general formula (1), the TADF material can be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0161] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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:

[0166]

[0167] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0168] 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 term "electron blocking layer" or "exciton blocking layer" includes a layer that has both the function of an electron blocking layer and the function of an exciton blocking layer.

[0169] 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.

[0170]

[0171] 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. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0172]

[0173] 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.

[0174] 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.

[0175]

[0176] 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.

[0177]

[0178] 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.

[0179]

[0180] 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.

[0181] 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).

[0182] 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.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] 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.

[0190] 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.

[0191] The features of the present invention will be explained in more detail below with reference to examples and synthesis examples of compounds represented by general formula (1). 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).

[0192] (Synthesis Example 1) Synthesis of Compound A

[0193] Intermediate a: Under a nitrogen stream, toluene (63 mL) was added to a mixture of 6-chloro-2,4-diphenylquinazoline (1.00 g, 3.15 mmol), 4-amino-3-(1-fluoro-8,8a-dihydro-9H-carbazol-9-yl)benzonitrile (1.13 g, 3.78 mmol), potassium carbonate (435 mg, 3.15 mmol), palladium(II) acetate (70.7 mg, 315 μmol), and tri-tert-butylphosphonium tetrafluoroborate (182 mg, 630 μmol), and the mixture was stirred at 110°C for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, and purified water was added, followed by filtration and extraction. The resulting mixture was purified by silica gel column chromatography to obtain intermediate a (1.27 g, 2.18 mmol, yield 69.3%). ASAP mass spectrometry: theoretical 581.20, observed 582.

[0194] Compound A: Under a nitrogen atmosphere, degassed dimethylformamide (100 mL) was added to a mixture of intermediate a (1.20 g, 2.06 mmol) and sodium tert-butoxide (462 mg, 4.12 mmol), and the mixture was heated to 120°C and reacted for 1 hour. After the reaction was complete, the mixture was cooled to room temperature, purified water was added, and the precipitated solid was filtered and washed with purified water and methanol. The resulting mixture was purified by silica gel column chromatography to obtain Compound A (920 mg, 1.63 mmol, 80.0% yield). ASAP mass spectrometry: theoretical 561.20, observed 562.38.

[0195] (Synthesis Example 2) Synthesis of Compound B

[0196] Intermediate b: Under a nitrogen stream, toluene (50 mL) was added to a mixture of 4-(6-chloro-4-phenyl-2-quinazolinyl)benzonitrile (0.80 g, 2.34 mmol), 4-amino-3-(1-fluoro-8,8a-dihydro-9H-carbazol-9-yl)benzonitrile (705 mg, 2.34 mmol), potassium carbonate (323 mg, 2.34 mmol), palladium(II) acetate (52.5 mg, 234 μmol), and tri-tert-butylphosphonium tetrafluoroborate (135 mg, 468 μmol), and the mixture was stirred at 110°C for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was filtered and extracted. The resulting mixture was purified by silica gel column chromatography to obtain Intermediate b (974 mg, 1.62 mmol, yield 69.1%). ASAP mass spectrometry: theoretical 606.20, observed 607.23.

[0197] Compound B: Under a nitrogen atmosphere, degassed dimethylformamide (30 mL) was added to a mixture of intermediate b (900 mg, 1.48 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (64.6 mg, 1.62 mmol). The mixture was heated to 150°C and reacted for 15 hours. After the reaction was complete, the mixture was cooled to room temperature, purified water was added, and the precipitated solid was filtered and washed with purified water and methanol. The resulting mixture was purified by silica gel column chromatography to obtain Compound B (520 mg, 886 μmol, yield 59.9%). 1H-NMR (400 MHz, CDCl3) δ 8.89-8.87 (m, 2H), 8.49 (d, J = 9.2 Hz, 1H), 8.26 (d, J = 2.3 Hz, 1H), 8.03 (d, J = 7.3 Hz, 1H), 7.95-7.85 (m, 6H), 7.74 (d, J = 1.8 Hz, 1H), 7.61-7.56 (m, 4H), 7.37 (t, J = 7.3 Hz, 1H), 7.29 (d, J = 6.9 Hz, 1H), 6.92 (dd, J = 8.2, 1.8 Hz, 1H), 6.75 (t, J = 7.8 Hz, 1H), 6.00 (d, J = 8.2 Hz, 1H), 5.70 (d, J = 7.3 Hz, 1H) ASAP mass spectrometry: Calculated 586.19, Observed 587.23.

[0198] (Synthesis Example 3) Synthesis of Compound C

[0199] Intermediate c: Under a nitrogen stream, tetrahydrofuran (THF, 276 mL) and water (138 mL) were added to a mixture of 2,4,7-trichloro[1]benzothieno[3,2-d]pyrimidine (8.00 g, 27.6 mmol), 4-cyanophenylboronic acid (4.05 g, 27.6 mmol), sodium carbonate (5.85 g, 55.2 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.59 g, 1.38 mmol), and the mixture was stirred at 80°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and water was added, followed by filtration and extraction. The resulting mixture was purified by reprecipitation from dichloromethane and methanol to obtain intermediate c (2.50 g, 7.01 mmol, yield 25.4%). 1 H-NMR (400 MHz, CDCl3) δ 8.54 (d, J = 8.2 Hz, 1H), 8.34 (dt, J = 8.2, 1.8 Hz, 2H), 7.93 (td, J = 7.3, 1.8 Hz, 3H), 7.62 (dd, J = 8.7, 1.8 Hz, 1H) ASAP mass spectrum analysis: theoretical value 354.97, observed value 355.99.

[0200] Intermediate d: Under a nitrogen stream, THF (35 mL) and water (17 mL) were added to a mixture of intermediate c (1.25 g, 3.50 mmol), phenylboronic acid (1.10 g, 3.85 mmol), sodium carbonate (741 mg, 7.00 mmol), and tetrakis(triphenylphosphine)palladium(0) (202 mg, 175 μmol), and the mixture was stirred at 80° C. for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, and water was added, followed by filtration and extraction. The resulting mixture was purified by silica gel column chromatography to obtain intermediate d (1.11 g, 2.78 mmol, 79.8% yield). 1 H-NMR (400 MHz, CDCl3) δ 8.75-8.73 (m, 2H), 8.65 (dd, J = 8.5, 0.5 Hz, 1H), 8.46 (dd, J = 6.6, 2.1 Hz, 2H), 7.95-7.93 (m, 3H), 7.63-7.56 (m, 4H) ASAP mass spectrum analysis: theoretical value 397.04, observed value 398.12.

[0201] Compound C: Under a nitrogen stream, degassed toluene (110 mL) was added to a mixture of intermediate d (1.10 g, 2.76 mmol), 4-amino-3-(1-fluoro-8,8a-dihydro-9H-carbazol-9-yl)benzonitrile (913 mg, 3.05 mmol), potassium carbonate (762 mg, 5.52 mmol), palladium(II) acetate (61.9 mg, 276 μmol), and tri-tert-butylphosphonium tetrafluoroborate (160 mg, 552 μmol), and the mixture was stirred at 110°C for 12 hours. After completion of the reaction, the reaction solution was filtered while still hot. The solid obtained by filtration was purified by recrystallization using 1,2-dichlorobenzene (o-DCB) to obtain an orange solid. This orange solid was purified by silica gel column chromatography to obtain Compound C (880 mg, 1.36 mmol, yield 49.7%). 1H-NMR (400 MHz, CDCl3) δ 9.05 (d, J = 8.5 Hz, 1H), 8.79 (dd, J = 7.8, 1.8 Hz, 2H), 8.52-8.49 (m, 2H), 8.05-8.03 (m, 2H), 7.98-7.96 (m, 2H), 7.92 (d, J = 8.5 Hz, 1H), 7.76 (d, J = 1.6 Hz, 1H), 7.68 (dd, J = 8.2, 1.8 Hz, 1H), 7.63-7.58 (m, 4H), 7.41-7.37 (m, 1H), 7.30-7.27 (m, 1H), 6.94 (dd, J = 8.5, 1.8 Hz, 1H), 6.76 (t, J = 7.9 Hz, 1H), 6.06 (d, J = 8.5 Hz, 1H), 5.74 (d, J = 7.6 Hz, 1H). ASAP mass spectrometry: Calculated 642.16, Observed 643.24.

[0202] (Synthesis Example 4) Synthesis of Compound D

[0203] Intermediate e: Under a nitrogen stream, THF (78 mL) and water (38 mL) were added to a mixture of 2,4,7-trichloro[1]benzothieno[3,2-d]pyrimidine (6.76 g, 23.3 mmol), phenylboronic acid (2.84 g, 23.3 mmol), sodium carbonate (4.93 g, 46.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (1.34 g, 1.16 mmol), and the mixture was stirred at 80°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered and extracted. The resulting mixture was purified by reprecipitation from dichloromethane and methanol to obtain intermediate e (3.06 g, 9.23 mmol, yield 39.6%). ASAP mass spectrometry: theoretical 329.98, observed 331.06.

[0204] Intermediate f: Under a nitrogen stream, THF (15 mL) and water (7.5 mL) were added to a mixture of intermediate e (1.50 g, 4.52 mmol), 4-cyanophenylboronic acid (0.994 g, 6.77 mmol), sodium carbonate (1.43 g, 13.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.261 g, 0.226 mmol), and the mixture was stirred at 80°C for 15 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was filtered and extracted. The resulting mixture was purified by reprecipitation from dichloromethane and methanol to obtain intermediate f (1.30 g, 3.26 mmol, yield 72.0%). 1 H-NMR (400 MHz, DMSO-D6) δ 8.88 (d, J = 8.5 Hz, 2H), 8.70 (d, J = 8.7 Hz, 1H), 8.50 (d, J = 1.8 Hz, 1H), 8.36-8.34 (m, 2H), 8.11 (d, J = 8.5 Hz, 2H), 7.80 (d, J = 8.2 Hz, 1H), 7.76-7.74 (m, 3H) ASAP mass spectrum analysis: theoretical value 397.04, observed value 398.03.

[0205] Intermediate g: Under a nitrogen stream, degassed toluene (104 mL) was added to a mixture of intermediate f (1.25 g, 3.14 mmol), 4-amino-3-(1-fluoro-8,8a-dihydro-9H-carbazol-9-yl)benzonitrile (1.03 g, 3.45 mmol), sodium tert-butoxide (603 mg, 6.28 mmol), palladium(II) acetate (70.4 mg, 0.314 mmol), and tri-tert-butylphosphonium tetrafluoroborate (182 mg, 0.628 mmol), and the mixture was stirred at 110°C for 14 hours. After completion of the reaction, the reaction solution was filtered while still hot to remove the precipitate. The filtrate was concentrated and purified by silica gel column chromatography to obtain intermediate g (1.13 g, 1.70 mmol, yield 54.3%). ASAP mass spectrometry: theoretical 662.17, observed 663.30.

[0206] Compound D: Under a nitrogen atmosphere, degassed dimethylformamide (169 mL) was added to a mixture of intermediate g (1.13 g, 1.70 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (74.6 mg, 1.87 mmol), and the mixture was heated to 150°C and reacted for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, and the precipitated solid was filtered. The solid obtained by filtration was purified by silica gel column chromatography to obtain compound D (268 mg, 0.417 mmol, yield 24.5%). 1 H-NMR (400 MHz, CDCl3) δ 9.02 (d, J = 8.2 Hz, 1H), 8.93 (dd, J = 6.6, 1.8 Hz, 2H), 8.38 (dd, J = 7.9, 1.7 Hz, 2H), 8.05-8.04 (m, 2H), 7.93-7.87 (m, 3H), 7.76 (d, J = 1.6 Hz, 1H), 7.71-7.66 (m, 4H), 7.61-7.57 (m, 1H), 7.41-7.36 (m, 1H), 7.30-7.27 (m, 1H), 6.94 (dd, J = 8.5, 1.6 Hz, 1H), 6.76 (t, J = 7.9 Hz, 1H), 6.06 (d, J = 8.5 Hz, 1H), 5.74 (d, J = 7.1 Hz, 1H). ASAP mass spectrometry: Calculated 642.16, Observed 643.27.

[0207] (Synthesis Example 5) Synthesis of Compound E

[0208] Intermediate h: Under a nitrogen stream, degassed toluene (720 mL) was added to a mixture of intermediate f (8.60 g, 21.6 mmol), 2-(1-fluoro-9H-carbazol-9-yl)benzenamine (6.54 g, 23.7 mmol), potassium carbonate (5.97 g, 43.2 mmol), palladium(II) acetate (484 mg, 2.16 mmol), and tri-tert-butylphosphonium tetrafluoroborate (1.25 g, 4.32 mmol), and the mixture was stirred at 110°C for 12 hours. After completion of the reaction, the reaction solution was filtered while still hot to remove the precipitate. The filtrate was concentrated and purified by silica gel column chromatography to obtain intermediate h (8.60 g, 13.4 mmol, yield 62.7%). 1 H-NMR (400 MHz, DMSO-D6) δ 8.80-8.78 (m, 2H), 8.58 (s, 1H), 8.28-8.23 (m, 3H), 8.16 (d, J = 7.6 Hz, 1H), 8.06 (dd, J = 6.6, 1.8 Hz, 2H), 7.98 (dd, J = 7.4, 1.3 Hz, 1H), 7.73-7.67 (m, 4H), 7.58-7.54 (m, 1H), 7.50-7.46 (m, 2H), 7.41-7.37 (m, 1H), 7.31-7.14 (m, 6H) ASAP mass spectrum analysis: theoretical value 637.17, Observed value 638.23.

[0209] Compound E: Under a nitrogen atmosphere, degassed dimethylformamide (134 mL) was added to a mixture of intermediate h (8.60 g, 13.4 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (586 mg, 14.7 mmol), and the mixture was heated to 150°C and reacted for 15 hours. After completion of the reaction, the mixture was cooled to room temperature, and the precipitated solid was filtered. The solid obtained by filtration was purified by silica gel column chromatography to obtain Compound E (7.35 g, 11.8 mmol, yield 88.8%). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.99 (d, J = 7.8 Hz, 1H), 8.94 (dd, J = 6.9, 1.8 Hz, 2H), 8.38 (dd, J = 8.0, 1.6 Hz, 2H), 8.07-7.99 (m, 3H), 7.88 (dd, J = 6.8, 1.9 Hz, 2H), 7.73-7.65 (m, 5H), 7.56-7.51 (m, 1H), 7.33 (t, J = 7.6 Hz, 1H), 7.25 (s, 1H), 6.86-6.83 (m, 1H), 6.74 (t, J = 7.8 Hz, 1H), 6.69-6.65 (m, 1H), 6.12 (dd, J = 8.2, 1.4 Hz, 1H), 5.75 (d, J = 7.1 Hz, 1H). ASAP mass spectrometry: Calculated 617.17, Observed 618.22.

[0210] (Synthesis Example 6) Synthesis of Compound F

[0211] Intermediate i: Under a nitrogen stream, degassed toluene (125 mL) was added to a mixture of intermediate f (1.00 g, 2.51 mmol), 9-(2-aminophenyl)-8-fluoro-9H-carbazole-3-carbonitrile (0.831 g, 2.76 mmol), potassium carbonate (693 mg, 5.02 mmol), palladium(II) acetate (56.3 mg, 0.251 mmol), and tri-tert-butylphosphonium tetrafluoroborate (145 mg, 0.502 mmol), and the mixture was stirred at 110°C for 14 hours. After the reaction was complete, the hot reaction solution was filtered to remove the precipitate. The filtrate was concentrated and purified by silica gel column chromatography to obtain intermediate i (0.657 g, 0.991 mmol, 39.5% yield). ASAP mass spectrometry analysis: theoretical 662.17, observed 662.31.

[0212] Compound F: Under a nitrogen atmosphere, degassed dimethylformamide (20.0 mL) was added to a mixture of intermediate i (0.657 g, 0.991 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (47.1 mg, 1.18 mmol), and the mixture was heated to 150°C and reacted for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, and the precipitated solid was filtered. The solid obtained by filtration was purified by silica gel column chromatography to obtain compound F (0.610 g, 0.949 mmol, yield 95.9%). 1 H-NMR (400 MHz, CDCl3) δ 9.01 (d, J = 8.5 Hz, 1H), 8.94 (d, J = 8.7 Hz, 2H), 8.39-8.35 (m, 3H), 8.07-8.05 (m, 2H), 7.88 (d, J = 8.7 Hz, 2H), 7.77 (dd, J = 8.8, 1.7 Hz, 1H), 7.71-7.65 (m, 5H), 7.27-7.25 (m, 1H), 6.90 (t, J = 7.7 Hz 1H), 6.84 (t, J = 7.8 Hz, 1H), 6.78 (t, J = 7.2 Hz, 1H), 6.19 (dd, J = 8.2, 1.4 Hz, 1H), 5.85 (d, J = 7.1 Hz, 1H). ASAP mass spectrometry: Calculated 642.16, Observed 643.24.

[0213] (Synthesis Example 7) Synthesis of Compound G

[0214] Intermediate j: Under a nitrogen stream, degassed toluene (182 mL) was added to a mixture of 7-chloro-2,4-diphenyl[1]benzothieno[3,2-d]pyrimidine (1.36 g, 3.64 mmol), 2-(1-fluoro-9H-carbazol-9-yl)benzenamine (1.10 g, 4.00 mmol), potassium carbonate (1.00 g, 7.28 mmol), palladium(II) acetate (81.7 mg, 0.364 mmol), and tri-tert-butylphosphonium tetrafluoroborate (211 mg, 0.728 mmol), and the mixture was stirred at 110°C for 38 hours. After completion of the reaction, the reaction solution was filtered while still hot to remove the precipitate. The filtrate was concentrated and purified by silica gel column chromatography to obtain intermediate j (1.58 g, 2.57 mmol, yield 70.8%). ASAP mass spectrometry: theoretical 612.18, observed 612.27.

[0215] Compound G: Under a nitrogen atmosphere, degassed dimethylformamide (51.3 mL) was added to a mixture of intermediate j (1.58 g, 2.57 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (133 mg, 3.34 mmol), and the mixture was heated to 150°C and reacted for 14 hours. After completion of the reaction, the mixture was cooled to room temperature, and the precipitated solid was filtered. The solid obtained by filtration was purified by silica gel column chromatography to obtain compound G (0.940 g, 1.58 mmol, yield 61.7%). 1 H-NMR (400 MHz, CDCl3) δ 9.00 (d, J = 8.2 Hz, 1H), 8.82 (dd, J = 8.2, 1.6 Hz, 2H), 8.41-8.38 (m, 2H), 8.05-7.99 (m, 3H), 7.71-7.51 (m, 9H), 7.32 (t, J = 7.4 Hz, 1H), 7.23 (d, J = 7.6 Hz, 1H), 6.86-6.82 (m, 1H), 6.74 (t, J = 7.8 Hz, 1H), 6.70-6.65 (m, 1H), 6.13 (dd, J = 8.2, 1.4 Hz, 1H), 5.75 (d, J = 7.6 Hz, 1H) ASAP Mass Spectral Analysis: Calculated 592.17, Observed 593.13

[0216] (Synthesis Example 8) Synthesis of Compound H

[0217] Intermediate k: Under a nitrogen stream, THF (21.4 mL) and water (10.7 mL) were added to a mixture of 2,4-dichloro-6,7-difluoroquinazoline (505 mg, 2.14 mmol), phenylboronic acid (260 mg, 2.14 mmol), sodium carbonate (453 mg, 4.28 mmol), and tetrakis(triphenylphosphine)palladium(0) (123 mg, 107 μmol), and the mixture was stirred at 60°C for 3 hours. The reaction solution was cooled to room temperature, and 4-cyanophenylboronic acid (314 mg, 2.14 mmol), sodium carbonate (453 mg, 4.28 mmol), and tetrakis(triphenylphosphine)palladium(0) (123 mg, 107 μmol) were added, followed by stirring at 60°C for 15 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was filtered and extracted. The resulting mixture was purified by silica gel column chromatography to obtain intermediate k (500 mg, 1.45 mmol, yield 68.1%). ASAP mass spectrometry analysis: theoretical value 343.09, observed value 344.26.

[0218] Compound H: Under a nitrogen atmosphere, degassed dimethylformamide (28.9 mL) was added to a mixture of 4H-4-azadibenzo[g,ij]naphtho[2,1,8-cde]azulene (929 mg, 3.19 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (121 mg, 3.04 mmol), and the mixture was cooled to 0°C. A solution of intermediate k (500 mg, 1.45 mmol) in degassed dimethylformamide (30 mL) was slowly added dropwise to the mixture. After stirring at room temperature for 15 minutes, the mixture was heated to 120°C and reacted for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitated solid was filtered. The resulting mixture was purified by silica gel column chromatography to obtain Compound H (1.27 g, 1.43 mmol, yield 99.2%). ASAP mass spectrometry analysis: theoretical value 885.29, observed value 886.34

[0219] (Synthesis Example 9) Synthesis of Compound I

[0220] Intermediate 1: Under a nitrogen atmosphere, 4-chloro-2-fluorobenzonitrile (18.2 g, 117 mmol) was added to degassed dimethylformamide (292 mL) and cooled to 0°C. A solution of 2-[(2-bromophenyl)amino]-1-phenylethanone (34.0 g, 117 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (4.86 g, 122 mmol) in degassed dimethylformamide (292 mL) was slowly added dropwise. The mixture was stirred at 0°C for 1 hour and then reacted at room temperature for 15 hours. After completion of the reaction, water was added for extraction. The resulting mixture was purified by silica gel column chromatography to obtain Intermediate 1 (34.4 g, 80.8 mmol, 69.0% yield). ASAP Mass Spectral Analysis: Calculated 424.00, Observed 425.26.

[0221] Intermediate m: Intermediate l (31.0 g, 72.8 mmol), 4-formylbenzonitrile (14.2 g, 109 mmol), and ammonium acetate (28.0 g, 364 mmol) were added to acetic acid (364 mL) and stirred at 120°C for 15 hours. The reaction solution was cooled to room temperature, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.29 g, 145 mmol) was added. The mixture was stirred at 120°C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. The resulting mixture was purified by silica gel column chromatography to obtain intermediate m (14.0 g, 26.1 mmol, 35.8% yield). ASAP mass spectrometry analysis: theoretical value 534.02, observed value 535.29.

[0222] Intermediate n: Under a nitrogen stream, degassed dimethylacetamide (522 mL) was added to a mixture of intermediate m (14.0 g, 26.1 mmol), palladium(II) acetate (585 mg, 2.61 mmol), tricyclohexylphosphine (2.19 g, 7.83 mmol), and cesium carbonate (17.0 g, 52.2 mmol), and the mixture was stirred at 130°C for 1.5 hours. After the reaction was complete, the mixture was cooled to room temperature, and water was added. The mixture was filtered and extracted. The resulting mixture was purified by silica gel column chromatography to obtain intermediate n (4.30 g, 9.45 mmol, 36.4% yield). ASAP mass spectrometry analysis: theoretical value 454.10, observed value 455.31.

[0223] Intermediate o: Under a nitrogen stream, degassed toluene (522 mL) was added to a mixture of intermediate n (4.00 g, 8.79 mmol), 2-(1-fluoro-9H-carbazol-9-yl)benzenamine (2.66 g, 9.66 mmol), palladium(II) acetate (197 mg, 8.79 mmol), tri-tert-butylphosphonium tetrafluoroborate (507 mg, 1.75 mmol), and potassium carbonate (7.41 g, 17.5 mmol), and the mixture was stirred at 110°C for 15 hours. After the reaction was complete, the mixture was cooled to room temperature, and water was added. The mixture was then filtered and extracted. The resulting mixture was purified by silica gel column chromatography to obtain intermediate o (4.17 g, 6.00 mmol, 68.3% yield). ASAP mass spectrometry analysis: theoretical value 694.23, observed value 695.45.

[0224] Compound I: Under a nitrogen atmosphere, degassed dimethylformamide (120 mL) was added to a mixture of intermediate o (4.17 g, 6.00 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (158 mg, 6.60 mmol), and the mixture was heated to 150°C and reacted for 15 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the precipitated solid was filtered. The resulting mixture was purified by silica gel column chromatography to obtain Compound I (3.49 g, 5.17 mmol, yield 86.3%). ASAP mass spectrometry analysis: theoretical value 674.22, observed value 675.34

[0225] (Example 1) Preparation and evaluation of thin film A thin film was prepared by vacuum deposition on a quartz substrate at a vacuum level of 1×10 －３ Compound A was evaporated under conditions of less than 1×10 Pa to form a thin film consisting of only Compound A to a thickness of 100 nm, which was used as a neat thin film. －３ Compounds A and H1 were evaporated from different evaporation sources under conditions of less than 1 Pa, and a thin film with a concentration of compound A of 20 wt % was formed to a thickness of 100 nm to serve as a doped thin film. Instead of compound A, compounds B to I and comparative compound 1 were used, respectively, to form neat thin films and doped thin films. The HOMO and LUMO energies were measured using each of the formed neat thin films. Delayed fluorescence was observed when each of the formed doped thin films was irradiated with 300 nm excitation light. The results of measuring the emission peak wavelength, photoluminescence quantum yield (PLQY), and delayed fluorescence lifetime (τ2) are shown in the table below, along with the measurement results of the HOMO and LUMO energies. It was confirmed that the compound represented by general formula (1) has a higher luminous efficiency and a shorter delayed fluorescence lifetime than comparative compound 1 described in U.S. Patent Publication No. 2022 / 0115600.

[0226]

[0227] (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 －６The layers were laminated at 100 Pa. First, HATCN was formed on ITO to a thickness of 10 nm, and NPD was formed on top of that to a thickness of 30 nm. Next, TrisPCz was formed on top of that to a thickness of 10 nm, and H2 was further formed on top of that to a thickness of 5 nm. Next, Compound A and H2 were co-deposited from different evaporation sources to form a 30 nm thick light-emitting layer. At this time, the concentration of Compound A was 35 wt%. SF3TRZ was formed on top of that to a thickness of 10 nm, and SF3TRZ and Liq were co-deposited on top of that to a thickness of 30 nm from different evaporation sources. At this time, the SF3TRZ:Liq (weight ratio) was 7:3. Next, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode. Using the above procedure, an organic electroluminescent device was fabricated. In addition, instead of compound A, compounds B to I and comparative compound 1 were used to prepare organic electroluminescence devices by the same procedure. When a current was applied to each organic electroluminescence device, delayed fluorescence was observed. The light emitted from each device was greatest from compounds A to I and comparative compound 1. Each device was operated at a current of 15.4 mA / cm ２ and the external quantum efficiency (EQE) when driven at 50 mA / cm ２ The time (LT95) until the light emission intensity reached 95% of the initial value when the device was continuously driven at 1000 kJ / s was measured. The results are shown in the table below.

[0228]

[0229] It was confirmed that organic electroluminescence devices using a compound represented by general formula (1) have higher luminous efficiency and longer device lifetimes than comparative compound 1 described in U.S. Patent Publication No. 2022 / 0115600. Introducing a cyano group as a substituent into a donor group such as the group represented by general formula (2) typically results in poor donor properties and a shorter device lifetime. Despite the introduction of a cyano group into the donor group represented by general formula (2), compounds A to D and F achieved significantly longer device lifetimes than comparative compound 1, which does not have a cyano group. This demonstrates the significant improvement in device lifetime of the compound represented by general formula (1). Furthermore, an organic electroluminescence device was prepared using comparative compound 2 using the same procedure, and the LT95 was measured, resulting in a value of 3.5 hours. It was also confirmed that the compound represented by general formula (1) has higher device stability and a longer device lifetime than comparative compound 2, which has a pyrazine ring instead of a pyrimidine ring.

[0230] Example 3: Preparation and Evaluation of Organic Electroluminescence Devices Using Compound A as an Assist Dopant

[0043] An organic electroluminescence device was prepared in the same manner as in Example 2, except that Compound A, H2, and F38 were co-deposited from different deposition sources to form a 30 nm thick light-emitting layer. At this time, the concentration of Compound A was 35 wt%, the concentration of H2 was 64.5 wt%, and the concentration of F38 was 0.5 wt%. Furthermore, instead of Compound A, Compounds B to G, I, and Comparative Compound 1 were used, and organic electroluminescence devices were prepared in the same manner. When a current was applied to each organic electroluminescence device, delayed fluorescence was observed. The light emitted from each device was greatest from Compounds A to G, I, and Comparative Compound 1. Each device was operated at 15.4 mA / cm ２ The initial driving voltage and external quantum efficiency (EQE) were measured when the device was driven at 1000 kJ / s. The results are shown in the table below.

[0231]

[0232] It was confirmed that the organic electroluminescence device using the compound represented by general formula (1) had a lower initial driving voltage and higher luminous efficiency than the comparative compound 1 described in U.S. Patent Publication No. 2022 / 0115600. Furthermore, when the LT95 of each device was compared, the stability of the devices using compounds A to G and I was equal to or greater than that of the device using comparative compound 1, and in particular, the LT95 of the devices using compounds A to C, E, and I was more than seven times that of the device using comparative compound 1. When an organic electroluminescence device was prepared using the same procedure using comparative compound 2 and the LT95 was measured, it was less than half that of the device using comparative compound 2 and was clearly inferior to the device using compounds A to G and I. From this, it was confirmed that the device using the compound represented by general formula (1) had a low initial driving voltage, high luminous efficiency, and excellent device stability.

[0233]

[0234] By using the compound represented by general formula (1), an organic light-emitting device such as an organic electroluminescence device having good characteristics can be provided. Therefore, the present invention has a high industrial applicability.

Claims

1. A compound represented by the following general formula (1): General formula (1) In the general formula (1), Ar represents a monocyclic aromatic ring or an aromatic ring in which 2 to 4 rings are condensed. Don represents a donor group. Acp represents a deuterium atom or a substituent other than a donor group. R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Acp or Don may be bonded to each other to form a cyclic structure, １ and R ２ , R ２ and Acp, R ２ and Don, and Acp and Don do not bond to each other to form a cyclic structure. b is an integer of 1 or more and not more than the maximum substitutable number of the aromatic ring represented by Ar, and a is an integer of 0 or more and not more than the number obtained by subtracting b from the maximum substitutable number of the aromatic ring represented by Ar. When Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom, at least one of the b Don is a donor group containing a nitrogen-atom-shared fused ring structure in which two rings are fused together, sharing a nitrogen atom.] 2. The compound according to claim 1, which is represented by the following general formula (1a): General formula (1a) In the general formula (1a), Ar represents a monocyclic aromatic ring or an aromatic ring in which 2 to 4 rings are condensed. D represents a group containing a substituted amino group. R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ３ represents a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, but does not include a substituted amino group. １ and R ３ may be bonded to each other to form a cyclic structure, but R １ and R ２ , R １ and D.R. ２ and R ３ , R ２ and D.R. ３ and D do not bond to each other to form a cyclic structure. m is an integer of 1 to 3, and n is an integer of 0 or more and not more than the maximum substitutable number of the aromatic ring represented by Ar minus m. When Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom, at least one of the m Ds is an amino group containing a nitrogen-atom-shared fused ring structure in which two rings are fused together, sharing a nitrogen atom.] 3. The compound according to claim 1, wherein at least one of Don is a group represented by the following general formula (2): [In the general formula (2), R ５ ~R １５ each independently represents a hydrogen atom, a deuterium atom or a substituent, or 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 １２ and R １３ , R １３ and R １４ , R １４ and R １５ are bonded to each other to form a ring structure. X represents a single bond, an oxygen atom, or a sulfur atom. * represents the bonding site.

4. R ５ ~R １５ are each independently a group containing a hydrogen atom, a deuterium atom or a cyano group, or 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 １２ and R １３ , R １３ and R １４ , R １４ and R １５ The compound of claim 3 , wherein: are linked to each other to form a cyclic structure.

5. The compound according to claim 1, wherein at least one of Don is a group represented by the following general formula (b): [In the general formula (b), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N, Z ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, Z ９ is C-R ２１ or N. １４ ~R ２１ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 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 At least one pair of these may be bonded to each other to form a cyclic structure. * indicates the bonding site.] 6. At least R １７ and R １８ The compound of claim 5 , wherein are bonded to each other to form a cyclic structure.

7. The compound according to claim 2, wherein Ar is a monocyclic aromatic ring whose ring skeleton is composed only of carbon atoms, or an aromatic ring having 2 to 4 condensed rings whose ring skeleton is composed only of carbon atoms.

8. The compound according to claim 2, wherein Ar is an aromatic ring whose ring skeleton is composed of carbon atoms and at least one heteroatom.

9. R １ and R ２ are each independently one group or a group formed by linking two or more groups selected from the group consisting of an alkyl group optionally substituted with a deuterium atom or a cyano group, an aryl group optionally substituted with a deuterium atom or a cyano group, and a heteroaryl group optionally substituted with a deuterium atom or a cyano group.

10. The compound according to claim 2, which is represented by the following general formula (3): General formula (3) [In the general formula (3), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｄ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｄ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

11. The compound according to claim 2, which is represented by the following general formula (18): General formula (18) [In the general formula (18), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｄ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｄ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. X represents a single bond, an oxygen atom, a sulfur atom, or N(R Ｚ ) and R Ｚ represents a hydrogen atom, a deuterium atom, or a substituent.

12. The compound according to claim 2, which is represented by the following general formula (19): General formula (19) [In the general formula (19), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｄ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｄ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. X represents a single bond, an oxygen atom, a sulfur atom, or N(R Ｚ ) and R Ｚ represents a hydrogen atom, a deuterium atom, or a substituent.

13. The compound according to claim 2, which is represented by the following general formula (40): General formula (40) [In general formula (40), R １ and R ２ R each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ａ ~R ｇ One to three of R represent a substituted amino group, and the remaining R ａ ~R ｇ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

14. The compound of claim 1 having at least one cyano group.

15. A light-emitting material comprising the compound according to any one of claims 1 to 14.

16. An organic light-emitting device comprising a compound according to any one of claims 1 to 14.

17. The organic light-emitting device according to claim 16, which is an organic electroluminescence device.

18. The organic light-emitting device of claim 17, wherein the organic electroluminescent device has a layer containing the compound, the layer also containing a host material.

19. The organic light-emitting element according to claim 18, wherein the layer further comprises, in addition to the compound and the host material, a light-emitting material having a structure outside the scope of general formula (1), and the lowest excited singlet energy of the light-emitting material is lower than those of the host material and the compound.

20. The organic light-emitting device according to claim 18, wherein the compound emits the greatest amount of light among the materials contained in the organic electroluminescent device.

21. The organic light-emitting device according to claim 16, which emits delayed fluorescence.

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