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

Abstract

A compound represented by general formula below is useful as a material for an organic light-emitting device. X1 and X2 respectively represent O or S; Y1 and Y2 respectively represent a single bond, O, S or C(Ra)(Rb); and R1-R22, Ra and Rb respectively represent H, deuterium atom or a substituent provided that one or more of R1-R22 are substituents.

Description

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

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

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

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

[0004] Although various studies have been conducted on compounds that exhibit the multiple resonance effect, there are still many unknowns regarding the relationship between their structure and luminescence properties. In order to manufacture practical light-emitting devices, it is necessary to provide materials with even slightly better luminescence properties. Therefore, the present inventors have conducted extensive research with the aim of developing compounds having a new ring skeleton.

[0005] As a result of extensive investigations, the present inventors have found that compounds that exhibit a multiple resonance effect and have a characteristic skeletal structure are useful as materials for organic light-emitting devices. The present invention has been proposed based on this finding and has the following configuration.

[0006] [1] A compound represented by the following general formula (1): [In the general formula (1), 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 R １０ , 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 , R１０ 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 substituted with N.] [2] R １ ~R ２２ is a group formed by combining one or more selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group, and an aryl group (some or all of the hydrogen atoms in the group may be substituted with deuterium atoms), or a substituted or unsubstituted diarylamino group (two aryl groups constituting the diarylamino group may be linked to each other via a linking group). １ ~R ２２ [4] The compound according to [1] or [2], wherein at least one of R is an aryl group optionally substituted with one or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group. ６ , R ９ , R １７ , R ２０ [5] The compound according to any one of [1] to [3], wherein R １ ~R ２２ Among them, R ２ , R ３ , R ６ , R ９ , R１３ , R １４ , R １７ , R ２０ [6] The compound according to any one of [1] to [4], wherein only 1 to 6 selected from the group consisting of R １ ~R ２２ [7] The compound according to any one of [1] to [5], wherein R １ ~R ２２ The compound according to any one of [1] to [6], wherein the total number of benzene rings is 2 to 6. [8] Y １ and Y ２ [9] The compound according to any one of [1] to [7], wherein X is a single bond. １ and X ２ is O.

[10] The compound according to any one of [1] to [9], having a point-symmetric structure.

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

[10] .

[12] A film comprising the compound according to any one of [1] to

[10] .

[13] An organic semiconductor device comprising the compound according to any one of [1] to

[10] .

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

[10] .

[15] The organic light-emitting device according to

[14] , wherein the device has a layer comprising the compound, and the layer also contains a host material.

[16] The organic light-emitting device according to

[15] , wherein the layer comprising the compound also contains a delayed fluorescent material in addition to the host material, 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.

[17] The organic light-emitting device according to

[14] , wherein the device has a layer comprising the compound, and the layer also contains a light-emitting material having a structure different from that of the compound.

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

[14] to

[16] , wherein the compound has the largest amount of light emission among the materials contained in the device.

[19] The organic light-emitting device according to

[17] , wherein the amount of light emission from the light-emitting material is greater than the amount of light emission from the compound.

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

[14] to

[19] , wherein the organic light-emitting device emits delayed fluorescence.

[0007] The compounds of the present invention exhibit excellent luminescence properties and are easy to synthesize. The compounds of the present invention include compounds with high orientation, compounds with narrow half-widths, and compounds that exhibit high luminescence efficiency. Furthermore, the compounds of the present invention include compounds that exhibit red luminescence.

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

[0009] [Compound Represented by General Formula (1)] The compound of the present invention is a compound represented by the following general formula (1).

[0010]

[0011] In general formula (1), X １ and X ２ Each independently represents O or S. In a preferred embodiment of the present invention, X １ and X ２ are both O. In one aspect of the present invention, X １ and X ２ and are both S. In one aspect of the present invention, X １ and X ２ One of the groups is O and the other is S. In general formula (1), Y １and Y ２ are each independently a single bond, O, S or C(R ａ ) (R ｂ In a preferred embodiment of the present invention, Y １ and Y ２ In one aspect of the present invention, Y １ and Y ２ are both O. In one aspect of the present invention, Y １ and Y ２ and are both S. In one aspect of the present invention, Y １ and Y ２ Both are C(R ａ ) (R ｂ In one aspect of the present invention, X １ and X ２ In one embodiment of the present invention, X １ and X ２ One of the groups is O and the other is S. In a preferred embodiment of the present invention, X １ and X ２ are both O, and Y １ and Y ２ are both a single bond, O or S, more preferably a single bond or O, and even more preferably a single bond. １ and X ２ are both S and Y １ and Y ２ are both a single bond, O or S, more preferably a single bond. １ and X ２ are both O, and Y １ and Y ２ are both O, S or C(R ａ ) (R ｂ ) more preferably, both are O or S, and even more preferably, both are O. In one aspect of the present invention, X １ and X ２ are both S and Y １ and Y ２ are both O, S or C(R ａ ) (R ｂ ) and more preferably both are O or S.

[0012] In general formula (1), R 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. The substituent here may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, R １ ~R ２２ is a group consisting of one or a combination of two or more selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group, and an aryl group (some or all of the hydrogen atoms in the group may be substituted with deuterium atoms), or a substituted or unsubstituted diarylamino group (two aryl groups constituting the diarylamino group may be linked to each other via a linking group). In a preferred embodiment of the present invention, R ａ , R ｂ are each independently a hydrogen atom, a deuterium atom, or one group selected from the group consisting of an alkyl group and an aryl group, or a group consisting of a combination of two or more groups (some or all of the hydrogen atoms in the group may be substituted with deuterium atoms).

[0013] The "aryl group" referred to herein may be a monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of rings after fusion 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 naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. Specific examples of the aryl group include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalen-1-yl group, and a substituted or unsubstituted naphthalen-2-yl group. Some or all of the hydrogen atoms of the aryl group may be substituted with deuterium atoms. Some or all of the hydrogen atoms of the aryl group may be substituted with a substituent. The substituent for the aryl group may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. The "alkyl group" referred to herein may be linear, branched, or cyclic. In addition, two or more of the straight-chain portion, cyclic portion, and branched portion may be present in combination. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 3 or more. The number of carbon atoms can 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. Some or all of the hydrogen atoms in the alkyl group may be substituted with deuterium atoms. The substituent of the alkyl group may be selected, for example, from Substituent Group A, from Substituent Group B, from Substituent Group C, from Substituent Group D, or from Substituent Group E.

[0014] In a preferred embodiment of the present invention, R １ ~R ２２The substituent that can be taken by is one group selected from the group consisting of alkyl groups and aryl groups, or a group combining two or more groups (some or all of the hydrogen atoms present in the group may be substituted with deuterium atoms). For example, it is an alkyl group that may be substituted with one or more groups selected from the group consisting of deuterium atoms and aryl groups. Preferably, it is an aryl group that may be substituted with one or more groups selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups, and more preferably, it is a phenyl group that may be substituted with one or more groups selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups.

[0015] In one aspect of the present invention, R １ ~R ２２ The substituent may be an aryl group substituted with an electron-withdrawing group. The electron-withdrawing group referred to here has a Hammett σp value of 0.3 or more, preferably 0.5 or more, and more preferably 0.6 or more. The Hammett σp value was proposed by L. P. Hammett and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the σp is a constant specific to the substituent in the para-substituted benzene derivative, which holds between the substituent and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant of the benzene derivative without a substituent, k is the rate constant of the benzene derivative substituted with a substituent, K0 is the equilibrium constant of the benzene derivative without a substituent, K is the equilibrium constant of the benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett σp value" in the present invention and the numerical values ​​of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991). Specific examples of the electron-withdrawing group include a fluorinated alkyl group and a cyano group. The fluorinated alkyl group is preferably a perfluoroalkyl group, and examples thereof include perfluoroalkyl groups having 1 to 4 carbon atoms.

[0016] In a preferred embodiment of the present invention, R １ ~R ２２ The substituent that can be taken by is a substituted or unsubstituted diarylamino group. The two aryl groups constituting the diarylamino group may be linked to each other by a linking group. For example, a single bond, —O—, —S—, —C(R ｃ ) (R ｄ ) -, -N(R ｅ )- may be linked. ｃ , R ｄ , R ｅ each independently represents a hydrogen atom, a deuterium atom, or a substituent, and is preferably one group selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group, and an aryl group, or a group combining two or more of these groups (some or all of the hydrogen atoms in the group may be substituted with deuterium atoms). The diarylamino group may be substituted with a substituent, and the substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the substituent of the diarylamino group is one or a group combining two or more selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group (some or all of the hydrogen atoms in the group may be substituted with deuterium atoms). R １ ~R ２２The substituted or unsubstituted diarylamino group represented by the formula (I) is preferably a substituted or unsubstituted carbazol-9-yl group. The two benzene rings constituting the carbazol-9-yl group may each independently be fused with another ring. The fused ring may be an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, or an aliphatic heterocyclic ring, or may be a ring formed by further condensing these. An aromatic ring, a heteroaromatic ring, or a fused ring thereof is preferred. An example of an aromatic 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; for example, a 5-membered ring or a 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, a pyrrole ring, or a pyridine ring can be employed as the heteroaromatic ring. In one embodiment of the present invention, the cyclic structure is an optionally substituted benzene ring, which may be fused with one or more other cyclic structures, such as a benzene ring or a furan ring. The benzene ring may be unsubstituted. In one embodiment of the present invention, the cyclic structure is a furan ring which may be substituted, and may be fused with one or more other cyclic structures such as a benzene ring or a furan ring. Preferred examples of the carbazol-9-yl group include an unsubstituted carbazol-9-yl group, a carbazol-9-yl group substituted at least at one of the 3- and 6-positions, and a carbazol-9-yl group substituted at both the 3- and 6-positions.

[0017] R １ ~R ２２ The number of substituents is preferably 1 to 12, more preferably 1 to 8, and even more preferably 1 to 6. For example, it may be selected from the range of 1 to 3, or may be selected from the range of 4 to 6. More preferably, it is 4 to 6. In one preferred embodiment of the present invention, R ２ , R ３ , R ６ , R ９ , R １３ , R １４ , R １７ , R ２０ are substituents, and R ２ , R ３ , R６ , R ９ , R １３ , R １４ , R １７ , R ２０ In a preferred embodiment of the present invention, R ６ , R ９ , R １７ , R ２０ is a substituent. For example, R ６ , R ９ , R １７ , R ２０ is the only substituent. For example, R ２ , R ６ , R ９ , R １３ , R １７ , R ２０ is the only substituent. For example, R ３ , R ６ , R ９ , R １４ , R １７ , R ２０ is the only substituent. １ ~R ２２ When there are two or more substituted or unsubstituted aryl groups among R, the two or more aryl groups are preferably the same, but may be different. １ ~R ２２ The compound represented by the general formula (1) is superior to a compound having zero substituents.

[0018] R １ ~R ２２ The total number of carbon atoms in R may be, for example, 10 or more, 20 or more, or 30 or more, and may be 80 or less, 60 or less, or 40 or less. １ ~R ２２ The total number of carbon atoms in R is selected from the range of 10 to 80, preferably from the range of 10 to 60. １ ~R ２２ The total number of carbon atoms in R may be selected from the range of 20 to 40, for example, from 20 to 30, or from 31 to 40. １ ~R ２２The total number of benzene rings in R is selected from the range of 0 to 24. For example, it may be 1 or more, 2 or more, 4 or more, or 6 or more, or 18 or less, 12 or less, 8 or less, or 6 or less. In one embodiment of the present invention, R １ ~R ２２ The total number of benzene rings is selected from the range of 2 to 8, preferably from the range of 2 to 6, and may be selected from the range of 4 to 6, for example.

[0019] In the following, R １ ~R ２２ Among specific examples of the substituents that R may take, specific examples of one group or a combination of two or more groups selected from the group consisting of alkyl groups and aryl groups are shown as N1 to N36. １ ~R ２２ Among specific examples of substituents that may be taken by N1, specific examples of substituted or unsubstituted diarylamino groups are shown as D1 to D117. However, the substituents that can be employed in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position, and methyl groups are omitted. For example, N1 is a methyl group, N2 is an ethyl group, N3 is an isopropyl group, and N4 is a tert-butyl group.

[0020] Groups in which all hydrogen atoms of N1 to N36 and D1 to D117 have been replaced with deuterium atoms are herein referred to as N1(D) to N36(D) and D1(D) to D117(D), respectively. Groups in which all hydrogen atoms of alkyl groups of N8 to N25, D2 to D14, D34 to D45, D64 to D75, and D100 to D111 have been replaced with deuterium atoms are herein referred to as N8(a) to N25(a), D2(a) to D14(a), D34(a) to D45(a), D64(a) to D75(a), and D100(a) to D111(a), respectively. Groups in which all hydrogen atoms of the phenyl groups N26 to N30, D15 to D21, D46 to D57, and D76 to D117 have been substituted with deuterium atoms are herein referred to as N26(Ph) to N30(Ph), D15(Ph) to D21(Ph), D46(Ph) to D57(Ph), and D76(Ph) to D117(Ph), respectively.

[0021] Y １ and Y ２ C(R ａ ) (R ｂ ) R ａ and R ｂ is preferably one group selected from the group consisting of alkyl groups and aryl groups, or a group consisting of a combination of two or more groups (some or all of the hydrogen atoms present in the group may be substituted with deuterium atoms). ａ and R ｂ may be the same or different, but are preferably the same. Specific examples include the above-mentioned N1 to N36 and N1(D) to N36(D). In a preferred embodiment of the present invention, R ａ and R ｂ are both unsubstituted aryl groups, more preferably unsubstituted phenyl groups. ａ and R ｂ are both unsubstituted alkyl groups, more preferably alkyl groups having 1 to 4 carbon atoms, such as a methyl group.

[0022] In general formula (1), R 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 R １０ , 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. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a ring formed by condensing these. An aromatic ring or a heteroaromatic ring is preferred. An example of the aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring, or may be condensed with 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, and for example, a 5-membered ring or a 6-membered ring may be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be adopted as the heteroaromatic ring. In one embodiment of the present invention, R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ , R７ and Y １ , Y １ 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 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 In one embodiment of the present invention, one or more pairs of R 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 R １０ , 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 , R１９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ In general formula (1), none of R 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 ring structure.

[0023] C-R in general formula (1) 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 substituted with N. When substituted with N, the number of substitutions is preferably 1 to 6, and may be, for example, 4 to 6, or 1 to 3. For example, C-R １ , C-R ２ , C-R ３ , C-R ４ , C-R １２ , C-R １３ , C-R １４ , C-R １５ Of these, 0 to 4, for example 1 to 2 may be substituted with N. For example, C—R ５ , C-R ６ , C-R ７ , C-R ８ , C-R９ , C-R １０ Of these, 0 to 4, for example 1 to 2 may be substituted with N. For example, C—R １６ , C-R １７ , C-R １８ , C-R １９ , C-R ２０ , C-R ２１ , C-R ２２ In one embodiment of the present invention, 0 to 4, for example 1 to 2 of C—R 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 None of the groups are substituted with N.

[0024] The compound represented by general formula (1) preferably does not contain a metal atom. The metal atom here does not include a boron atom. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, sulfur, and boron. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and boron. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, nitrogen, oxygen, and boron. For example, the compound represented by general formula (1) may be a compound consisting of atoms selected from the group consisting of carbon, hydrogen, nitrogen, sulfur, and boron. In one embodiment of the present invention, the number of oxygen atoms in the molecule is 2 to 4, for example, 2, for example, 4. In one embodiment of the present invention, the number of nitrogen atoms in the molecule is 2 to 8, preferably 2 to 4, for example, 2, for example, 4. The number of boron atoms in the molecule is 2 to 8, preferably 2 to 4, for example 2, for example 4.

[0025] In the present specification, "substituent group A" refers to a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton atoms), a heteroaryl ... It means one group or a combination of two or more groups selected from the group consisting of a heteroarylthio group (for example, having 5 to 30 atoms constituting the ring skeleton), an acyl group (for example, having 1 to 40 carbon atoms), an alkenyl group (for example, having 1 to 40 carbon atoms), an alkynyl group (for example, having 1 to 40 carbon atoms), an alkoxycarbonyl group (for example, having 1 to 40 carbon atoms), an aryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a silyl group (for example, a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group. In the present specification, "substituent group B" refers to one group or a combination of two or more groups selected from the group consisting of 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 atoms), heteroaryloxy groups (e.g., having 5 to 30 ring atoms), and diarylamino groups (e.g., having 0 to 20 carbon atoms). In the present specification, "substituent group C" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), heteroaryl groups (e.g., having 5 to 20 ring atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). As used herein, "substituent group D" means one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms) and heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms).As used herein, "substituent group E" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms). Some or all of the hydrogen atoms present in the groups described in these substituent groups A to E may be substituted with deuterium atoms. In the present specification, when a "substituent" or "substituted or unsubstituted" is used, the substituent may be selected, for example, from substituent group A, from substituent group B, from substituent group C, from substituent group D, or from substituent group E.

[0026] In one embodiment of the present invention, a compound having a rotationally symmetric structure is selected as the compound represented by general formula (1). １ ~R １１ are in order of R １２ ~R ２２ is the same as X １ and X ２ are identical, and Y １ and Y ２ In one embodiment of the present invention, a compound having an asymmetric structure is selected as the compound represented by general formula (1).

[0027] The compound represented by general formula (1) preferably has, for example, any one of the following skeleton structures: X in the skeleton structure represents O or S, and Y represents O, S, or C(R ａ ) (R ｂ ) and R ａ and R ｂ is as defined in general formula (1). At least one hydrogen atom in the following skeleton may be substituted with a deuterium atom or a substituent. Furthermore, rings may be fused. For details of the substituents and fused rings, please refer to the corresponding descriptions in the explanation of general formula (1).

[0028]

[0029] Specific examples of the compound represented by general formula (1) are shown below. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, R in general formula (I) ２ , R ３ , R ６ , R ９ , R １３ , R １４ , R １７ , R ２０ The structures of compounds 1 to 480 are shown individually by specifying each compound. In Table 2, R ２ , R ３ , R ６ , R ９ , R １３ , R １４ , R １７ , R ２０ For example, in the column of compounds 1 to 160 in Table 2, R ３ and R １４ is fixed to a hydrogen atom (H), and R ２ , R ６ , R ９ , R １３ , R １７ , R ２０ are all any of X1 to X160, are designated as Compounds 1 to 160 in order. That is, the column of Compounds 1 to 160 in Table 2 collectively displays Compounds 1 to 160 specified in Table 1. Similarly, in the column of Compounds 161 to 320 in Table 2, R ２ and R １３ is fixed to a hydrogen atom (H), and R ３ , R ６ , R ９ , R １４ , R １７ , R ２０are all either X1 to X160, are designated as compounds 161 to 320, in that order. The structures of compounds 321 to 67200 in Table 2 are also identified in the same manner. In Table 2, - in the Y column means that Y is a single bond. NPh in the Z column represents a nitrogen atom bonded to a phenyl group. The structures of X1 to X160 are listed after Table 2.

[0030]

[0031] Groups in which all hydrogen atoms present in X1 to X58 have been substituted with deuterium atoms are shown here as X103 to X160, in that order. Compounds 1(D) to 67200(D) are disclosed in which all hydrogen atoms present in the molecules of the above compounds have been substituted with deuterium atoms. All compounds identified by the above numbers are considered to be individually disclosed. In addition, when rotamers exist among the above specific compound examples, both the mixture of rotamers and each separated rotamer are considered to be disclosed in the present specification.

[0032] In one embodiment of the present invention, a compound is selected from compounds 1 to 67200. In one embodiment of the present invention, a compound is selected from compounds 1(D) to 67200(D). In one embodiment of the present invention, a compound is selected from compounds 1 to 32641. In one embodiment of the present invention, a compound is selected from compounds 32642 to 67200. In one embodiment of the present invention, a compound is selected from compounds 1 to 2560. In one embodiment of the present invention, a compound is selected from compounds 2561 to 26560. In one embodiment of the present invention, a compound is selected from compounds 26561 to 30400. In one embodiment of the present invention, a compound is selected from compounds 30401 to 32641. In one embodiment of the present invention, a compound is selected from compounds 32642 to 36160. In one embodiment of the present invention, a compound is selected from compounds 36161 to 60160. In one embodiment of the present invention, a compound is selected from compounds 60161 to 64000. In one embodiment of the present invention, a compound is selected from compounds 64001 to 67200. In one embodiment of the present invention, compounds are selected from the range of compounds 1 to 2080. In one embodiment of the present invention, compounds are selected from the range of compounds 2081 to 2240. In one embodiment of the present invention, compounds are selected from the range of compounds 2241 to 2400. In one embodiment of the present invention, compounds are selected from the range of compounds 2401 to 2560. In one embodiment of the present invention, compounds are selected from the range of compounds 2561 to 4960. In one embodiment of the present invention, compounds are selected from the range of compounds 4961 to 7360. In one embodiment of the present invention, compounds are selected from the range of compounds 7361 to 9760. In one embodiment of the present invention, compounds are selected from the range of compounds 9761 to 12160. In one embodiment of the present invention, compounds are selected from the range of compounds 12161 to 14560. In one embodiment of the present invention, compounds are selected from the range of compounds 14561 to 16960. In one embodiment of the present invention, compounds are selected from the range of compounds 19961 to 19360. In one embodiment of the present invention, compounds are selected from the range of compounds 19361 to 21760. In one embodiment of the present invention, compounds are selected from the range of compounds 21761 to 22240. In one aspect of the present invention, a compound is selected from among 22241 to 22720. In one aspect of the present invention, a compound is selected from among 22721 to 23200. In one aspect of the present invention, a compound is selected from among 23201 to 23680.In one embodiment of the present invention, a compound is selected from the range of 23681 to 24160. In one embodiment of the present invention, a compound is selected from the range of 24161 to 24640. In one embodiment of the present invention, a compound is selected from the range of 24641 to 25120. In one embodiment of the present invention, a compound is selected from the range of 25121 to 25600. In one embodiment of the present invention, a compound is selected from the range of 25601 to 26080. In one embodiment of the present invention, a compound is selected from the range of 26081 to 26560. In one embodiment of the present invention, a compound is selected from the range of 26561 to 28960. In one embodiment of the present invention, a compound is selected from the range of 28961 to 29440. In one embodiment of the present invention, a compound is selected from the range of 29441 to 29920. In one embodiment of the present invention, a compound is selected from the range of 29921 to 30400. In one embodiment of the present invention, a compound is selected from the range of 30401 to 32000. In one embodiment of the present invention, a compound is selected from the range of 32001 to 32320. In one embodiment of the present invention, a compound is selected from the range of 32321 to 32640. In one embodiment of the present invention, a compound is selected from the range of 32641 to 32960. In one embodiment of the present invention, a compound is selected from the range of 32961 to 33280. In one embodiment of the present invention, a compound is selected from the range of 33281 to 33600. In one embodiment of the present invention, a compound is selected from the range of 33601 to 35680. In one embodiment of the present invention, a compound is selected from the range of 35681 to 35840. In one embodiment of the present invention, a compound is selected from the range of 35841 to 36000. In one embodiment of the present invention, a compound is selected from the range of 36001 to 36160. In one embodiment of the present invention, a compound is selected from the range of 36161 to 38560. In one embodiment of the present invention, a compound is selected from the range of 38561 to 40960. In one embodiment of the present invention, a compound is selected from the range of 40961 to 43360. In one embodiment of the present invention, a compound is selected from the range of 43361 to 45760. In one aspect of the present invention, a compound is selected from among 45761 to 48160. In one aspect of the present invention, a compound is selected from among 48161 to 50560. In one aspect of the present invention, a compound is selected from among 50561 to 52960. In one aspect of the present invention, a compound is selected from among 52961 to 55360. In one aspect of the present invention, a compound is selected from among 55361 to 55840.In one embodiment of the present invention, a compound is selected from the range of 55841 to 56320. In one embodiment of the present invention, a compound is selected from the range of 56321 to 56800. In one embodiment of the present invention, a compound is selected from the range of 56801 to 57280. In one embodiment of the present invention, a compound is selected from the range of 57281 to 57760. In one embodiment of the present invention, a compound is selected from the range of 57761 to 58240. In one embodiment of the present invention, a compound is selected from the range of 58241 to 58720. In one embodiment of the present invention, a compound is selected from the range of 58721 to 59200. In one embodiment of the present invention, a compound is selected from the range of 59201 to 59680. In one embodiment of the present invention, a compound is selected from the range of 59681 to 60160. In one embodiment of the present invention, a compound is selected from the range of 60161 to 62560. In one embodiment of the present invention, a compound is selected from the range of 62561 to 63040. In one embodiment of the present invention, a compound is selected from the range of 63041 to 63520. In one embodiment of the present invention, a compound is selected from among 63521 to 64000. In one embodiment of the present invention, a compound is selected from among 64001 to 65600. In one embodiment of the present invention, a compound is selected from among 65601 to 65920. In one embodiment of the present invention, a compound is selected from among 65921 to 66240. In one embodiment of the present invention, a compound is selected from among 66241 to 66560. In one embodiment of the present invention, a compound is selected from among 66561 to 66880. In one embodiment of the present invention, a compound is selected from among 66881 to 67200.

[0033] In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds:

[0034] 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 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. By using a coating method, it is possible to form a film even from a compound with a relatively large molecular weight. 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.

[0035] The compounds represented by general formula (1) include compounds with high orientation. For example, compounds with high orientation when a composition containing the compound represented by general formula (1) is formed into a film are included. The orientation can be evaluated by the orientation value (S value). The larger the negative value of the orientation value (the smaller the numerical value), the higher the orientation. The orientation value (S value) is calculated as follows: 7, 8405.

[0036] 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.

[0037] 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.

[0038] 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 １０４ each 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.

[0039] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0040] 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.

[0041] 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.

[0042] In certain embodiments, the compound represented by general formula (1) is a light-emitting material. In certain embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In certain embodiments, the compound represented by general formula (1) is a compound with a narrow half-width. In certain embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, 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. In certain embodiments of the present disclosure, the compound 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 610 nm to about 780 nm, about 650 nm). In certain embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the infrared spectral region (e.g., 780 nm to 2 μm). In an embodiment of the present disclosure, an organic semiconductor device can be fabricated using a compound represented by general formula (1). For example, a CMOS (complementary metal oxide semiconductor) can be fabricated using a compound represented by general formula (1). In an embodiment of the present disclosure, an organic optical device such as an organic electroluminescence device or a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1).

[0043] 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 ＳＴ The 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.

[0044] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) includes novel compounds. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, it can be synthesized by utilizing a ring-closure reaction or a substitution reaction. When utilizing a ring-closure reaction, for example, as shown in the following reaction formula, the compound can be synthesized by preparing a chloride, reacting it with n-butyllithium, adding boron tribromide, and then adding an amine to cause cyclization. For details of the reaction conditions, please refer to the synthesis examples described below. The compound represented by general formula (1) is easier to synthesize than other compounds that have similar skeletons and exhibit multiple resonance effects.

[0045] 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).

[0046] [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 the compound of the present invention 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 (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention 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 the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited to this. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compression molded product obtained by compressing the mixed powder may be used, or a mixture of the individual compounds may be used by heating, melting, and cooling. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film having a desired composition ratio can be easily formed by mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the resulting deposition source. In some embodiments, a temperature at which the weight loss rates of the co-deposited compounds are the same can be identified, and this temperature can be used as the temperature during co-deposition.

[0047] [Examples of Use of Compounds Represented by General Formula (1)] Compounds represented by general formula (1) are useful as materials for organic light-emitting devices. They are particularly suitable for use in organic light-emitting diodes and the like. Organic Light-Emitting Diodes: One aspect of the present invention relates to the use of compounds represented by general formula (1) of the present invention as light-emitting materials for organic light-emitting devices. In some embodiments, compounds represented by general formula (1) of the present invention can be effectively used as light-emitting materials in the light-emitting layer of organic light-emitting devices. In some embodiments, compounds represented by general formula (1) include 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 compounds represented by general formula (1) as delayed fluorescent materials. In some embodiments, the present invention can be used as a host material and can be used together with one or more light-emitting materials, which may be fluorescent materials, phosphorescent materials, or delayed fluorescent materials (TADFs). In some embodiments, compounds represented by general formula (1) can also be used as hole-transporting materials. In some embodiments, compounds represented by general formula (1) can be used as electron-transporting materials. In one embodiment, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In one embodiment, an organic light-emitting device comprising the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In one embodiment, an emitting layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is aligned parallel to a substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, 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 one embodiment, aligning the propagation direction of light emitted by the compound represented by general formula (1) improves light extraction efficiency from the emitting layer. One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device comprises an emitting layer. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device).In one embodiment, the compound represented by general formula (1) is the light-emitting material with the highest emission intensity among the components contained in the light-emitting layer. In one embodiment, the lowest excited singlet energy level of the compound represented by general formula (1) is the lowest among the lowest excited singlet energy levels of the components contained in the light-emitting layer. In one embodiment, two or more components having a lowest excited singlet energy level higher than the lowest excited singlet energy level of the compound represented by general formula (1) are contained. For example, three or more components are contained. 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 lowest excited singlet energy level of the compound represented by general formula (1) contained in the light-emitting layer 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 photoluminescent device includes at least one light-emitting layer. In one embodiment, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least an emissive layer. In some embodiments, the organic layer includes only an emissive layer. In some embodiments, the organic layer includes one or more organic layers in addition to the emissive layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, 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.

[0048] 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; that is, any host material capable of achieving high light emission efficiency can be used in the present invention without 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 molecule and a host material are used. In some embodiments, TADF 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.

[0049] When a 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.

[0050]

[0051] 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).

[0052] In one embodiment, when a host material is used, the amount of the compound of the present invention contained as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of the present invention contained as the light-emitting material in the light-emitting layer is 1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of the present invention contained as the light-emitting material in the light-emitting layer is 50% by weight or less. In one embodiment, when a host material is used, the amount of the compound of the present invention contained as the light-emitting material in the light-emitting layer is 20% by weight or less. In one embodiment, when a host material is used, the amount of the compound of the present invention contained as the light-emitting material in the light-emitting layer is 10% by weight or less. In one embodiment, the host material in the light-emitting layer is an organic compound having hole-transporting and electron-transporting functions. In one embodiment, the host material in the light-emitting layer is an organic compound that prevents an increase in the wavelength of emitted light. In one embodiment, the host material in the light-emitting layer is an organic compound having a high glass transition temperature. Preferred compounds that can be used as the host material are listed below, but the host materials that can be used in the present invention should not be construed as being limited by the following specific examples.

[0053] In the light-emitting layer, a delayed fluorescent material can be used as the light-emitting material or the assist dopant. Different delayed fluorescent materials can be used as the light-emitting material and the assist dopant. When the emission lifetime is measured using a fluorescence lifetime measurement system (such as a streak camera system manufactured by Hamamatsu Photonics), fluorescence with an emission lifetime of 100 ns (nanoseconds) or more is usually observed. The delayed fluorescent material has a difference ΔE between the lowest excited singlet energy and the lowest excited triplet energy 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. ＳＴ If the δ is small, reverse intersystem crossing from the excited singlet state to the excited triplet state is easily achieved by absorbing thermal energy, and the material functions as a thermally activated delayed fluorescent material. Thermally activated delayed fluorescent materials absorb heat emitted by a device and relatively easily undergo reverse intersystem crossing from the excited triplet state to the excited singlet state, allowing the excited triplet energy to efficiently contribute to light emission.

[0054] In the present invention, the lowest excited singlet energy (E Ｓ１ ) and the lowest excited triplet energy (E Ｔ１ ) is a value determined by the following procedure. ＳＴ is E Ｓ１ -E Ｔ１ (1) The lowest excited singlet energy (E Ｓ１ ) Thin film or toluene solution of the compound to be measured (concentration 10 －５ A sample is prepared by preparing a solution of 1000 mol / L. The fluorescence spectrum of this sample is measured at room temperature (300K). The fluorescence spectrum has the vertical axis representing emission and the horizontal axis representing wavelength. A tangent line is drawn to the rising edge of the short wavelength side of this emission spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is determined. This wavelength value is converted to an energy value using the following conversion formula, and the value is called E Ｓ１ Conversion formula: E Ｓ１ [eV] = 1239.85 / λedge. The emission spectra in the examples described below were measured using an LED light source (Thorlabs, M300L4) as the excitation light source and a detector (Hamamatsu Photonics, PMA-12 multichannel spectrometer C10027-01). (2) Lowest excited triplet energy (E Ｔ１ ) lowest excited singlet energy (E Ｓ１The same sample used in the measurement of ) is cooled to 77 [K] with liquid nitrogen, and the sample for phosphorescence measurement is irradiated with excitation light (300 nm), and the phosphorescence is measured using a detector. The emission from 100 milliseconds after irradiation with excitation light is taken as the phosphorescence spectrum. A tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is determined. This wavelength value is converted to an energy value using the following conversion formula, and the value E Ｔ１ Conversion formula: E Ｔ１ [eV] = 1239.85 / λedge A tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider a tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is maximum is defined as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points having peak intensities that are 10% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is maximum and is closest to the shortest wavelength maximum is defined as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.

[0055] It is preferable that the delayed fluorescent material does not contain metal atoms. For example, a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected as the delayed fluorescent material. For example, a compound consisting of carbon atoms, hydrogen atoms, and nitrogen atoms may be selected as the delayed fluorescent material. Typical delayed fluorescent materials include compounds having a structure in which one to two acceptor groups and at least one donor group are bonded to a benzene ring. Preferred examples of the acceptor group include groups containing a heteroaryl ring containing a nitrogen atom as a ring skeleton-constituting atom, such as a cyano group or a triazinyl ring. Preferred examples of the donor group include a substituted or unsubstituted carbazol-9-yl group. Examples of such compounds include a compound in which three or more substituted or unsubstituted carbazol-9-yl groups are bonded to the benzene ring, and a compound in which each of the five-membered ring moieties of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, or a substituted or unsubstituted silaindene ring is condensed to at least one of the two benzene rings constituting the carbazol-9-yl group.

[0056] In a preferred embodiment of the present invention, a compound represented by the following general formula (T1) is used as the delayed fluorescent material. In general formula (T1), R ２１ ~R ２３ one of R represents a cyano group or a group represented by the following general formula (T2): ２１ ~R ２３ The remaining two and R ２４ and R ２５ At least one of R represents a group represented by the following general formula (T3): ２１ ~R ２５ The remainder represents a hydrogen atom or a substituent (however, the substituent here does not represent a cyano group, a group represented by the following general formula (T2), or a group represented by the following general formula (T3)). In general formula (T2), L １ represents a single bond or a divalent linking group, R ３１ and R ３２each independently represents a hydrogen atom or a substituent, and * represents the bonding position. In general formula (T3), L ２ represents a single bond or a divalent linking group, R ３３ and R ３４ each independently represents a hydrogen atom or a substituent, and * represents the bonding position.

[0057] In a preferred embodiment of the present invention, R ２２ is a cyano group. In a preferred embodiment of the present invention, R ２２ is a group represented by general formula (T2). ２１ is a cyano group or a group represented by general formula (T2). ２３ is a cyano group or a group represented by general formula (T2). ２１ ~R ２３ In one embodiment of the present invention, one of R ２１ ~R ２３ One of these is a group represented by general formula (T2).

[0058] In a preferred embodiment of the present invention, L in general formula (T2) １ is a single bond. In one aspect of the present invention, L １ is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group, and even more preferably a substituted or unsubstituted 1,4-phenylene group (with, for example, an alkyl group having 1 to 3 carbon atoms as the substituent). In one embodiment of the present invention, R ３１ and R ３２ are each independently one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring skeleton atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), and alkynyl groups (e.g., having 1 to 40 carbon atoms) (hereinafter, these groups are referred to as "groups of substituent group A"). In a preferred embodiment of the present invention, R ３１ and R ３２are each independently a substituted or unsubstituted aryl group (e.g., having 6 to 30 carbon atoms), and examples of the substituent of the aryl group include the groups in Substituent Group A. In a preferred embodiment of the present invention, R ３１ and R ３２ are identical.

[0059] In a preferred embodiment of the present invention, L in general formula (T3) ２ is a single bond. In one aspect of the present invention, L ２ is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group, and even more preferably a substituted or unsubstituted 1,4-phenylene group (with, for example, an alkyl group having 1 to 3 carbon atoms as the substituent). In one embodiment of the present invention, R ３３ and R ３４each independently represents a substituted or unsubstituted alkyl group (e.g., having 1 to 40 carbon atoms), a substituted or unsubstituted alkenyl group (e.g., having 1 to 40 carbon atoms), a substituted or unsubstituted aryl group (e.g., having 6 to 30 carbon atoms), or a substituted or unsubstituted heteroaryl group (e.g., having 5 to 30 carbon atoms). Examples of the substituents on the alkyl group, alkenyl group, aryl group, and heteroaryl group mentioned here include a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 atoms constituting the ring skeleton), a heteroaryloxy group (e.g., having 5 to 30 atoms constituting the ring skeleton), and a heteroarylthi group. Examples of the substituents include one or a combination of two or more groups selected from the group consisting of an aryl group (e.g., 5 to 30 atoms constituting the ring skeleton), an acyl group (e.g., 1 to 40 carbon atoms), an alkenyl group (e.g., 1 to 40 carbon atoms), an alkynyl group (e.g., 1 to 40 carbon atoms), an alkoxycarbonyl group (e.g., 1 to 40 carbon atoms), an aryloxycarbonyl group (e.g., 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (e.g., 1 to 40 carbon atoms), a silyl group (e.g., a trialkylsilyl group having 1 to 40 carbon atoms), a nitro group, and a cyano group (hereinafter, these groups are referred to as "groups of substituent group B"). ３３ and R ３４ may be bonded to each other via a single bond or a linking group to form a cyclic structure. ３３ and R ３４ are aryl groups, they are preferably bonded to each other via a single bond or a linking group to form a cyclic structure. The linking group here includes -O-, -S-, -N(R ３５ ) -, -C(R ３６ ) (R ３７ )-, -C(=O)-, and -O-, -S-, -N(R ３５ ) -, -C(R ３６ ) (R ３７ )- is preferred, and —O—, —S—, —N(R ３５ )- is more preferred.３５ ~R ３７ each independently represents a hydrogen atom or a substituent. The substituent may be selected from the groups in the above-mentioned Substituent Group A or the groups in the below-mentioned Substituent Group B, and is preferably one group or a combination of two or more groups selected from the group consisting of alkyl groups having 1 to 10 carbon atoms and aryl groups having 6 to 14 carbon atoms.

[0060] The group represented by general formula (T3) is preferably a group represented by the following general formula (T4).

[0061] L in general formula (T4) １１ represents a single bond or a divalent linking group. １１ For the description and preferred range of L ２ The explanation and preferred range of R in general formula (T4) can be referred to. ４１ ~R ４８ R each independently represents a hydrogen atom or a substituent. ４１ and R ４２ , R ４２ and R ４３ , R ４３ and R ４４ , R ４４ and R ４５ , R ４５ and R ４６ , R ４６ and R ４７ , R ４７ and R ４８may be bonded to each other to form a cyclic structure. The cyclic structure formed by bonding to each other may be an aromatic ring or an aliphatic ring, may contain a heteroatom, and may further be a fused ring of two or more rings. The heteroatom referred to here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the cyclic structure formed include a benzene ring, a naphthalene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, an imidazoline ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentaene ring, a cycloheptatriene ring, a cycloheptadiene ring, a cycloheptaene ring, a furan ring, a thiophene ring, a naphthyridine ring, a quinoxaline ring, and a quinoline ring. For example, a ring formed by condensing multiple rings, such as a phenanthrene ring or a triphenylene ring, may be formed. The number of rings contained in the group represented by general formula (T4) may be selected from the range of 3 to 5, or may be selected from the range of 5 to 7. ４１ ~R ４８ Examples of the substituent that R may have include the groups in the above-mentioned substituent group B, and preferably an unsubstituted alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms which may be substituted with an unsubstituted alkyl group having 1 to 10 carbon atoms. In a preferred embodiment of the present invention, R ４１ ~R ４８ is a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. In a preferred embodiment of the present invention, R ４１ ~R ４８ is a hydrogen atom or an unsubstituted aryl group having 6 to 10 carbon atoms. ４１ ~R ４８ are all hydrogen atoms. In general formula (T4), * represents a bonding position.

[0062] In a preferred embodiment of the present invention, an azabenzene derivative is used as the delayed fluorescent material. In a preferred embodiment of the present invention, the azabenzene derivative has an azabenzene structure in which three of the carbon atoms constituting the ring skeleton of the benzene ring are substituted with nitrogen atoms. For example, an azabenzene derivative having a 1,3,5-triazine structure can be preferably selected. In a preferred embodiment of the present invention, the azabenzene derivative has an azabenzene structure in which two of the carbon atoms constituting the ring skeleton of the benzene ring are substituted with nitrogen atoms. For example, azabenzene derivatives having a pyridazine structure, pyrimidine structure, or pyrazine structure can be mentioned, and an azabenzene derivative having a pyrimidine structure can be preferably selected. In one embodiment of the present invention, the azabenzene derivative has a pyridine structure in which one of the carbon atoms constituting the ring skeleton of the benzene ring is substituted with a nitrogen atom.

[0063] In a preferred embodiment of the present invention, a compound represented by the following general formula (T5) is used as the delayed fluorescent material. In formula (T5), Y １ , Y ２ and Y ３ In one embodiment of the present invention, Y １ is a nitrogen atom, and Y ２ and Y ３ is a methine group. １ and Y ２ is a nitrogen atom, and Y ３ is a methine group. １ ~Y ３ In general formula (T5), all of Z １ ~Z ３ Each of Z independently represents a hydrogen atom or a substituent, and at least one of them is a donor substituent. A donor substituent refers to a group having a negative Hammett σp value. １ ~Z ３ At least one of Z is a group containing a diarylamino structure (two aryl groups bonded to a nitrogen atom may be bonded to each other), more preferably a group represented by the above general formula (T3), for example, a group represented by the above general formula (T4). １~Z ３ In one embodiment of the present invention, only one of Z １ ~Z ３ In one embodiment of the present invention, only two of Z are independently a group represented by general formula (T3) or (7). １ ~Z ３ are each independently a group represented by general formula (T3) or (7). For details and preferred ranges of general formula (T3) and general formula (T4), the corresponding descriptions above can be referred to. The remaining Z １ ~Z ３ is preferably a substituted or unsubstituted aryl group (e.g., having 6 to 40 carbon atoms, preferably 6 to 20 carbon atoms), and examples of the substituent of the aryl group here include one group selected from the group consisting of aryl groups (e.g., having 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms) and alkyl groups (e.g., having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms), or a group in which two or more groups are combined. In one embodiment of the present invention, general formula (T5) does not contain a cyano group.

[0064] In a preferred embodiment of the present invention, a compound represented by the following general formula (T6) is used as the delayed fluorescent material.

[0065] In one embodiment of the present invention, in General Formula (T6), Ar １ is the following A １ and D １ Ar forms a cyclic structure which may be substituted by Ar and represents a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring. ２ , Ar ３ may each form a cyclic structure, and when a cyclic structure is formed, it represents a benzene ring, a naphthalene ring, a pyridine ring, or a benzene ring substituted with a cyano group. m1 represents an integer of 0 to 2, and m2 represents an integer of 0 to 1. A １ represents a cyano group, a phenyl group, a pyrimidyl group, a triazyl group, or a benzonitrile group. １represents a substituted or unsubstituted 5H-indolo[3,2,1-de]phenazin-5-yl group, or a substituted or unsubstituted heterocyclic-fused carbazolyl group not containing a naphthalene structure, and １ When present, they may be the same or different. １ The substituents may be bonded to each other to form a ring structure.

[0066] In another embodiment of the present invention, in general formula (T6), Ar １ represents a cyclic structure, such as a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring. １ represents a group represented by the general formula (T7). １ represents one group or a combination of two or more groups selected from the group consisting of a cyano group, a phenyl group, a pyrimidyl group, a triazyl group, and an alkyl group (excluding substituted alkyl groups). m is 1 or 2, and n is 0, 1, or 2. When m is 2, two D １ may be the same or different. When n is 2, two A １ may be the same or different. ２ , Ar ３ may each independently form a cyclic structure selected from the group consisting of a benzene ring, a naphthalene ring, and a pyridine ring, and the formed cyclic structure may be substituted with one group or a combination of two or more groups selected from the group consisting of an alkyl group, an aryl group, a heteroaryl group, and a cyano group.

[0067] [In general formula (T7), R ５ ~R １５ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 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 １２and R １３ , R １３ and R １４ , R １４ and R １５ may be bonded to each other to form a cyclic structure. X represents a single bond, an oxygen atom or a sulfur atom. * represents the bonding position.

[0068] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E1):

[0069] In general formula (E1), 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 (E1) 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 substituted with N.

[0070] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E2).

[0071] In general formula (E2), 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 , R ６ 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 substituted with N.

[0072] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E3).

[0073] In formula (E3), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic 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 ３are 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 ２ At least one of the C-R in the general formula (E3) 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 substituted with N.

[0074] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E4).

[0075] In formula (E4), 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 ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３each 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.

[0076] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E5).

[0077] In general formula (E5), 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 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 , R ２ and R６ , 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 substituted with N.

[0078] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E6).

[0079] In general formula (E6), 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 as a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ is a nitrogen atom, and R ７ and R ８ and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ are bonded to each other to form an aromatic ring or a heteroaromatic ring.

[0080] Further preferred delayed fluorescent materials include compounds represented by the following general formula (E7):

[0081] In general formula (E7), R ２０１ ~R ２２１ R each independently represents a hydrogen atom, a deuterium atom, or a substituent, and preferably represents a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or a group in which an alkyl group and an aryl group are bonded. ２０１ and R ２０２ , R ２０２ and R ２０３ , R ２０３ and R ２０４ , R ２０５ and R ２０６ , R ２０６ and R ２０７ , R ２０７ and R ２０８ , R ２１４ and R ２１５ , R ２１５ and R ２１６ , R ２１６ and R ２１７ , R ２１８ and R ２１９ , R ２１９ and R ２２０ , R ２２０ and R ２２１ At least one pair of R is bonded to each other to form a benzofuro structure or a benzothieno structure. ２０１ and R ２０２ , R ２０２ and R ２０３ , R ２０３ and R ２０４ , R ２０５ and R ２０６ , R ２０６ and R ２０７ , R ２０７ and R ２０８ and one or two pairs of R ２１４ and R ２１５ , R ２１５ and R ２１６ , R ２１６ and R ２１７ , R ２１８ and R ２１９ , R ２１９ and R ２２０ , R ２２０ and R ２２１One or two of the groups bond together to form a benzofuro structure or a benzothieno structure. ２０３ and R ２０４ are bonded to each other to form a benzofuro or benzothieno structure, and even more preferably R ２０３ and R ２０４ , R ２１６ and R ２１７ are bonded to each other to form a benzofuro structure or a benzothieno structure. Particularly preferably, R ２０３ and R ２０４ , R ２１６ and R ２１７ are bonded to each other to form a benzofuro structure or a benzothieno structure, and R ２０６ and R ２１９ is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group).

[0082] Furthermore, compounds represented by general formula (1) described in the specifications of Japanese Patent Application Nos. 2021-103698, 2021-103699, 2021-103700, 2021-081332, 2021-103701, 2021-151805, and 2021-188860 can be used as delayed fluorescent materials. These descriptions of general formula (1) and specific compounds are herein cited as part of this specification.

[0083] Preferred compounds that can be used as delayed fluorescent materials are listed below: In the structural formulas of the following exemplary compounds, t-Bu represents a tertiary butyl group (tert-butyl group).

[0084] In addition to the above, known delayed fluorescent materials can be used in appropriate combination. Even unknown delayed fluorescent materials can be used. Examples of 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 paragraphs 0008 to 007 of WO2013 / 081088. 1 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, paragraphs 0008 to 0032 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- JP-A-2017-226838, paragraphs 0010 to 0050, JP-A-2018-100411, paragraphs 0012 to 0043, and WO 2018 / 047853, paragraphs 0016 to 0044. Compounds encompassed by the general formulas described in paragraphs 0012 to 0025, particularly exemplary compounds, which emit delayed fluorescence can be mentioned.Also, Japanese Patent Application Laid-Open No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 00858 0 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 / 133 It is also possible to employ luminescent materials that emit delayed fluorescence, such as 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.

[0085] 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 one embodiment, the luminescence quantum yield φPL2(B) upon photoexcitation of a co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-deposited film = 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 one embodiment, the luminescent layer can contain three types of TADF molecules with different structures. The compound of the present invention can be any of the multiple TADF compounds contained in the luminescent layer.

[0086] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0087] 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.

[0088] 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.

[0089] 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 O ３ 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.

[0090] 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:

[0091]

[0092] Next, examples of preferred compounds that can be used as the electron injection material will be given.

[0093] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functions of an electron blocking layer and an exciton blocking layer.

[0094] 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.

[0095]

[0096] 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.

[0097]

[0098] 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.

[0099] 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.

[0100]

[0101] 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.

[0102]

[0103] 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.

[0104]

[0105] 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.

[0106] 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).

[0107] 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.

[0108] 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.

[0109] 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 planarizing 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 into cell panels. 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 planarizing 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 into cell panels.

[0110] 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.

[0111] 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.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] The features of the present invention will be explained in more detail below with reference to synthesis examples and working examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), an absolute PL quantum yield measurement system (Hamamatsu Photonics K.K.: C11347 model), and a streak camera (Hamamatsu Photonics K.K.: C4334 model). The orientation value was measured using a molecular orientation property measurement system (Hamamatsu Photonics K.K.: C14234-01).

[0117] (Synthesis Example 1) Synthesis of Compound 120

[0118] Intermediate A Under a nitrogen stream, an N,N-dimethylformamide solution (60 mL) of 1,4-dibromo-2,5-difluorobenzene (5.00 g, 18.4 mmol), 2-chlorophenol (4.96 g, 38.6 mmol), and cesium carbonate (18.0 g, 55.2 mmol) was stirred at 120°C for 17 hours. The mixture was returned to room temperature, water was added, and the solid was filtered. The solid was purified by silica gel column chromatography (toluene:hexane=1:3) to obtain Intermediate A (5.22 g, 10.7 mmol, yield 58%) as a white solid. 1 H NMR (400 MHz, CDCl3, δ) : 7.59 (dd, J = 7.6, 1.2 Hz, 2H), 7.29-7.24 (m, 2H), 7.17-7.12 (m, 2H), 7.09 (s, 2H), 6.93 (dd, J = 8.0, 1.6 Hz, 2H) MS (ASAP) : 488.20 (M+H + ). Calcd for. C 18 H 10 Br2Cl2O2: 487.84

[0119] Intermediate B: Under a nitrogen stream, a xylene solution (30 mL) of Intermediate A (4.00 g, 8.18 mmol), 3,6-diphenylcarbazole (7.84 g, 24.5 mmol), copper iodide (0.598 g, 3.14 mmol), 1,10-phenanthroline (0.567 g, 3.14 mmol), potassium carbonate (6.78 g, 49.1 mmol), and 18-crown-6 (0.324 g, 1.23 mmol) was stirred at 160°C for 17 hours. The mixture was returned to room temperature and filtered through Celite, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene) and recrystallized from toluene and methanol to obtain Intermediate B (4.14 g, 4.29 mmol, yield 52%) as a white solid. 1H NMR (400 MHz, CDCl3, δ) : 8.35 (d, J = 2.0 Hz, 4H), 7.77-7.72 (m, 12 H), 7.59 (d, J = 8.8 Hz, 4H), 7.52-7.47 (m, 8H), 7.39-7.34 (m, 4H), 7.28-7.24 (m, 4H), 7.10-7.05 (m, 2H), 7.00 (dd, J = 8.0, 1.6 Hz, 2H), 6.96-6.91 (m, 2H) MS (ASAP): 965.56 (M+H + ). Calcd for. C 66 H 42 Cl2N2O2: 964.26

[0120]

[0121] Compound 120: Under a nitrogen stream, t-BuLi (1.6 mol / L pentane solution, 9.7 mL, 15.5 mmol) was added to a toluene solution (200 mL) of intermediate B (3.00 g, 3.11 mmol) at 0°C, and the mixture was stirred at 50°C for 45 minutes. The reaction mixture was cooled to 0°C, and boron tribromide (3.89 g, 15.5 mmol) was added. The mixture was stirred at room temperature for 30 minutes, after which N,N-diisopropylethylamine (4.01 g, 31.1 mmol) and o-dichlorobenzene were added and the mixture was stirred at 170°C for 20 hours. The mixture was returned to room temperature, filtered through Celite, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene) and recrystallized from o-dichlorobenzene and acetonitrile to give compound 120 (138 mg, 0.151 mmol, 5% yield) as a purple solid. MS (MALDI): 913.23 (M+H + ). Calcd for. C 66 H 38 B2N2O2: 912.31

[0122] (Synthesis Example 2) Synthesis of Compound 4

[0123] Intermediate C Under a nitrogen stream, a solution of 5-bromo-2-chlorophenol (10.4 g, 50.0 mmol), phenylboronic acid (6.40 g, 52.5 mmol), tetrakis(triphenylphosphine)palladium(0) (2.89 g, 2.50 mmol), and potassium carbonate (17.3 g, 125 mmol) in tetrahydrofuran / distilled water (100 mL / 50 mL) was stirred at 80°C for 16 hours. This mixture was returned to room temperature and filtered through Celite, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene:hexane=9:1) to obtain Intermediate C (8.63 g, 42.2 mmol, yield 84%) as a pale yellow oil. 1 H NMR (400 MHz, CDCl3, δ) : 7.57-7.53 (m, 2H), 7.467.40 (m, 2H), 7.38-7.33 (m, 2H), 7.26-7.25 (m, 1H), 7.10 (dd, J = 8.0, 2.0 Hz, 1H), 5.57 (s, 1H) MS (ASAP) : 204.94 (M+H + ). Calcd for. C 12 H9ClO: 204.03

[0124]

[0125] Intermediate D Under a nitrogen stream, an N,N-dimethylformamide solution (100 mL) of Intermediate C (8.63 g, 42.2 mmol), 1,4-dibromo-2,5-difluorobenzene (5.21 g, 19.17 mmol), and cesium carbonate (25.0 g, 76.7 mmol) was stirred at 140°C for 17 hours. The mixture was returned to room temperature, water was added, and the solid was filtered. The solid was purified by silica gel column chromatography (toluene) and recrystallized from toluene and methanol to obtain Intermediate D (4.09 g, 6.37 mmol, yield 33%) as a white solid. 1 H NMR (400 MHz, CDCl3, δ): 7.55 (d, J = 8.4 Hz), 7.53-7.49 (m, 4H), 7.46-7.41 (m, 4H), 7.40-7.35 (m, 4H), 7.15-7.14 (m, 4H) MS (ASAP): 640.03 (M+ ). Calcd for. C 30 H 18 Br2Cl2O2: 639.90

[0126]

[0127] Intermediate E: Under a nitrogen stream, a xylene solution (80 mL) of Intermediate D (4.08 g, 6.37 mmol), 3,6-diphenylcarbazole (6.11 g, 19.1 mmol), copper iodide (1.21 g, 6.37 mmol), 1,10-phenanthroline (1.15 g, 6.37 mmol), potassium carbonate (5.28 g, 38.2 mmol), and 18-crown-6 (0.253 g, 0.956 mmol) was stirred at 160°C for 16 hours. The mixture was returned to room temperature and filtered through Celite. The solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene) and recrystallized from toluene and methanol to obtain Intermediate E (4.42 g, 3.96 mmol, yield 62%) as a white solid. 1 H NMR (400 MHz, CDCl3, δ) : 8.32 (d, J = 2.0 Hz, 4H), 7.73-7.67 (m, 12 H), 7.59 (d, J = 8.8 Hz, 4H), 7.52-7.47 (m, 8H), 7.39-7.27 (m, 18H), 7.12-7.08 (m, 4H)

[0128]

[0129] Compound 4: Under a nitrogen stream, t-BuLi (1.6 mol / L pentane solution, 5.6 mL, 8.95 mmol) was added to a toluene solution (200 mL) of intermediate E (2.00 g, 1.79 mmol) at 0°C, and the mixture was stirred at 50°C for 30 minutes. The reaction mixture was cooled to 0°C, and boron tribromide (2.24 g, 8.95 mmol) was added. The mixture was stirred at room temperature for 30 minutes, after which N,N-diisopropylethylamine (2.31 g, 17.9 mmol) and o-dichlorobenzene were added and the mixture was stirred at 170°C for 20 hours. The mixture was returned to room temperature, and the precipitate was filtered. The solid was purified by silica gel column chromatography (o-dichlorobenzene) and recrystallized from o-dichlorobenzene and acetonitrile to obtain compound 4 (40.0 mg, 0.0375 mmol, 2% yield) as a purple solid.

[0130] (Synthesis Example 3) Synthesis of Compound 1979

[0131] Intermediate F: Under a nitrogen stream, a toluene solution (450 mL) of 4-amino-2-chlorophenol (12.9 g, 90.0 mmol), bromobenzene-d5 (32.1 g, 198 mmol), tris(dibenzylideneacetone)dipalladium(0) (4.12 g, 4.50 mmol), tri-tert-butylphosphonium tetrafluoroborate (2.61 g, 9.00 mmol), and sodium tert-butoxide (43.2 g, 450 mmol) was stirred at 110°C for 15 hours. This mixture was returned to room temperature, water was added, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate and then filtered, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (dichloromethane:hexane = 1:1) to obtain intermediate F (20.1 g, 65.8 mmol, 73% yield) as a yellow solid. 1 H NMR (400 MHz, CDCl3, δ) : 7.10 (d, J = 2.0 Hz, 1H), 6.97 (dd, J= 8.8 Hz, 2.0 Hz, 1H), 6.93 (d, J = 8.8 Hz, 1H). MS (ASAP) : 306.19 (M+H) + ). Calcd for. C 18 H4D 10ClNO: 305.14

[0132]

[0133] Intermediate G Under a nitrogen stream, an N,N-dimethylformamide solution (150 mL) of 1,4-dibromo-2,5-difluorobenzene (8.16 g, 30.0 mmol), Intermediate F (20.1 g, 65.8 mmol), and cesium carbonate (39.1 g, 120 mmol) was stirred at 160°C for 12 hours. The mixture was returned to room temperature, water was added, and the solid was filtered. The solid was purified by silica gel column chromatography (dichloromethane:hexane=1:3) to obtain Intermediate G (8.44 g, 10.0 mmol, yield 33%) as a yellow solid. 1 H NMR (400 MHz, CDCl3, δ): 7.17 (d, J = 2.8 Hz, 2H), 7.09 (s, 2H), 6.94 (dd, J = 8.8 Hz, 2.8 Hz, 2H), 6.83 (d, J = 8.8 Hz, 2H). MS (ASAP): 843.42 (M+H + ). Calcd for. C 42 H8D 20 Br2Cl2N2O2: 842.11

[0134]

[0135] Intermediate H: Under a nitrogen stream, a xylene solution (64 mL) of Intermediate G (7.89 g, 12.7 mmol), carbazole (4.67 g, 27.9 mmol), copper iodide (1.21 g, 6.35 mmol), 1,10-phenanthroline (1.14 g, 6.35 mmol), cesium carbonate (16.6 g, 50.8 mmol), and 18-crown-6 (0.671 g, 2.54 mmol) was stirred at 160°C for 42 hours. The mixture was returned to room temperature, water was added, and the mixture was extracted three times with toluene. The organic layer was dried over magnesium sulfate and then filtered, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (dichloromethane:hexane = 1:3) to obtain Intermediate H (2.06 g, 2.02 mmol, yield 16%) as a white solid. 1H NMR (400 MHz, CDCl3, δ) : 8.14 (d, J = 8.0 Hz, 4H), 7.50-7.44 (m, 8H), 7.35-7.31 (m, 4H), 7.30 (s, 2H), 8.50 (d, J = 2.8 Hz, 2H), 6.71 (d, J = 8.8 Hz, 2H), 6.65 (dd, J = 8.8 Hz, 2.8 Hz, 2H). MS (ASAP): (M+H + ). Calcd for. C 66 H 24 D 20 Cl2N4O2: 1014.41

[0136]

[0137] Compound 1979: Under a nitrogen stream, tert-butyllithium (1.6 mol / L pentane solution, 9.4 mL, 15.0 mmol) was added to a toluene solution (30 mL) of intermediate H (3.01 g, 3.00 mmol) at 0°C, and the mixture was stirred at 70°C for 30 minutes. The reaction mixture was cooled to 0°C, and boron tribromide (3.76 g, 15.0 mmol) was added. The mixture was stirred at room temperature for 1 hour, after which N,N-diisopropylethylamine (3.88 g, 30.0 mmol) and o-dichlorobenzene were added and the mixture was stirred at 185°C for 14 hours. The mixture was returned to room temperature, filtered through Celite, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene:hexane = 1:3) and recrystallized from dichloromethane and acetonitrile to give compound 1979 (120 mg, 0.125 mmol, 4% yield) as a purple solid. 1 H NMR (400 MHz, CDCl3, δ) : 8.57 (d, J = 2.8 Hz, 2H), 8.46-8.42 (m, 4H), 8.23 ​​(d, J = 7.6 Hz, 2H), 7.96 (d, J = 8.4 Hz, 2H), 7.59-7.54 (m, 4H), 7.52-7.43 (m, 4H), 7.39 (d, J = 8.8 Hz, 2H).

[0138] (Synthesis Example 4) Synthesis of Compound 33499

[0139] Intermediate I: Under a nitrogen atmosphere, Intermediate G (9.28 g, 11.0 mmol), 3-(phenyl-2,3,4,5,6-d ５ A xylene solution (90 mL) of 18-crown-6 (0.581 g, 2.20 mmol), copper iodide (1.05 g, 5.50 mmol), 1,10-phenanthroline (0.991 g, 5.50 mmol), cesium carbonate (14.3 g, 44.0 mmol), and 18-crown-6 (0.581 g, 2.20 mmol) was stirred at 160°C for 36 hours. The mixture was returned to room temperature, water was added, and the mixture was extracted three times with dichloromethane. The organic layer was dried over magnesium sulfate and then filtered, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (dichloromethane:hexane = 1:3) to obtain Intermediate I (7.93 g, 6.73 mmol, 61% yield) as a white solid. 1 H NMR (400 MHz, CDCl3, δ) : 8.75 (d, J = 2.0 Hz, 2H), 8.19 (d, J = 7.6 Hz, 2H), 7.74-7.71 (m, 2H), 7.57 (dd, J = 8.8 Hz, 3.6 Hz, 2H), 7.52-7.47 (m, 4H), 7.38-7.33 (m, 2H), 7.32 (s, 2H), 6.89 (d, J = 2.8 Hz, 2H), 6.77 (d, J = 8.8 Hz, 2H), 6.70 (dd, J = 8.8 Hz, 2.8 Hz, 2H). MS (ASAP): 1177.87 (M+H + ). Calcd for. C 78 H 22 D 30 Cl2N4O2: 1176.54

[0140]

[0141] Compound 33499: Under a nitrogen stream, tert-butyllithium (1.6 mol / L pentane solution, 6.8 mL, 11.0 mmol) was added to a toluene solution (22 mL) of intermediate I (2.59 g, 2.20 mmol) at −78°C and stirred at 70°C for 30 minutes. The reaction mixture was cooled to −78°C, and boron tribromide (2.76 g, 11.0 mmol) was added. The mixture was stirred at room temperature for 30 minutes. N,N-diisopropylethylamine (2.84 g, 22.0 mmol) and o-dichlorobenzene were then added and stirred at 185°C for 15 hours. The mixture was returned to room temperature and filtered through a silica gel pad. The solvent in the filtrate was then distilled off. The residue was purified by silica gel column chromatography (toluene:hexane=3:7) and recrystallized from dichloromethane and acetonitrile to give compound 33499 (289 mg, 0.257 mmol, 12% yield) as a purple solid. 1 H NMR (400 MHz, CDCl3, δ) : 8.6-8.4 (m, 4H), 8.39-8.30 (m, 2H), 8.19 (t, J = 8.0 Hz, 2H), 7.95-7.87 (m, 2H), 7.71 (dd, J = 8.8 Hz, 2.0 Hz, 2H), 7.52-7.38 (m, 4H), 7.34-7.28 (m, 2H).

[0142] (Synthesis Example 5) Synthesis of Compound 33179

[0143] Intermediate J: Under a nitrogen stream, a xylene solution (124 mL) of Intermediate G (5.25 g, 6.22 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (2.40 g, 13.7 mmol), copper iodide (0.592 g, 3.11 mmol), 1,10-phenanthroline (0.561 g, 3.11 mmol), cesium carbonate (8.11 g, 24.9 mmol), and 18-crown-6 (0.329 g, 1.24 mmol) was stirred at 170°C for 96 hours. The mixture was returned to room temperature, water was added, and the mixture was extracted three times with dichloromethane. The organic layer was dried over magnesium sulfate and then filtered, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (dichloromethane) and recrystallized from toluene to obtain Intermediate J (5.33 g, 5.17 mmol, 83% yield) as a brown solid. 1 H NMR (400 MHz, CDCl3, δ) : 7.31 (s, 2H), 6.85 (d, J = 2.4 Hz, 2H), 6.71 (d, J = 8.8 Hz, 2H), 6.65 (dd, J = 8.8 Hz, 2.4 Hz, 2H). MS (ASAP): 1031.79 (M+H + ). Calcd for. C 66 H8D 36 Cl2N4O2: 1030.51

[0144]

[0145] Compound 33179: Under a nitrogen stream, tert-butyllithium (1.6 mol / L pentane solution, 6.1 mL, 9.70 mmol) was added to a toluene solution (30 mL) of intermediate J (2.00 g, 1.94 mmol) at 0°C, and the mixture was stirred at 70°C for 30 minutes. The reaction mixture was cooled to 0°C, and boron tribromide (1.52 g, 9.70 mmol) was added. The mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (2.51 g, 19.4 mmol) and o-dichlorobenzene were then added, and the mixture was stirred at 185°C for 14 hours. The mixture was returned to room temperature, filtered through Celite, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene:hexane = 1:3) and recrystallized from dichloromethane and acetonitrile to give compound 33179 (75.8 mg, 0.0776 mmol, 4% yield) as a purple solid.

[0146] (Synthesis Example 6) Synthesis of Compound 1931

[0147] Intermediate K: Under a nitrogen stream, a toluene solution (580 mL) of 4-amino-2-chlorophenol (25.0 g, 174 mmol), bromobenzene (62.9 g, 401 mmol), tris(dibenzylideneacetone)dipalladium(0) (7.97 g, 8.71 mmol), tri-tert-butylphosphonium tetrafluoroborate (5.05 g, 17.4 mmol), and sodium tert-butoxide (58.6 g, 609 mmol) was stirred at 100°C for 15 hours. This mixture was returned to room temperature, water was added, and the mixture was extracted three times with toluene. The organic layer was dried over magnesium sulfate and then filtered, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene) to obtain Intermediate K (51.2 g, 173 mmol, 99% yield) as a dark orange liquid.

[0148]

[0149] Intermediate L Under a nitrogen stream, an N,N-dimethylformamide solution (490 mL) of 1,4-dibromo-2,5-difluorobenzene (40.0 g, 147 mmol), intermediate K (100 g, 338 mmol), and cesium carbonate (192 g, 588 mmol) was stirred at 160°C for 12 hours. The mixture was returned to room temperature, water was added, and the solid was filtered. The solid was washed with hexane, methanol, and acetone, respectively, to obtain intermediate L (46.0 g, 55.9 mmol, yield 38%) as a yellow solid. 1 H NMR (400 MHz, CDCl3, δ): 7.16 (d, J = 2.8 Hz, 2H), 7.13-7.03 (m, 22H), 6.94 (dd, J= 8.8 Hz, 2.8 Hz, 2H), 6.83 (d, J = 8.8 Hz, 2H). MS (ASAP): 823.22 (M+H + ). Calcd for. C 42 H 28 Br2Cl2N2O2: 821.99

[0150]

[0151] Intermediate M: Under a nitrogen stream, a xylene solution (533 mL) of Intermediate L (43.9 g, 53.3 mmol), carbazole (19.6 g, 117 mmol), copper iodide (5.07 g, 26.6 mmol), 1,10-phenanthroline (4.80 g, 26.6 mmol), cesium carbonate (69.4 g, 213 mmol), and 18-crown-6 (2.81 g, 10.6 mmol) was stirred at 170°C for 60 hours. The mixture was returned to room temperature, water was added, and the mixture was extracted three times with toluene. The organic layer was dried over magnesium sulfate and then filtered, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (dichloromethane:hexane = 1:3) and recrystallized from toluene to obtain Intermediate M (12.4 g, 12.4 mmol, yield 23.3%) as a brown solid. 1H NMR (400 MHz, CDCl3, δ) : 8.14 (d, J = 8.0 Hz, 4H), 7.50-7.44 (m, 8H), 7.35-7.30 (m, 6H), 7.20-7.15 (m, 8H), 7.00-6.95 (m, 4H), 6.87-6.84 (m, 10H), 6.71 (d, J = 8.4 Hz, 2H), 6.65 (dd, J = 8.1 Hz, 2.8 Hz, 2H). MS (ASAP): 995.59 (M+H + ). Calcd for. C 66 H 44 Cl2N4O2: 994.28

[0152]

[0153] Compound 1931: Under a nitrogen stream, tert-butyllithium (1.6 mol / L pentane solution, 9.4 mL, 15.1 mmol) was added to a toluene solution (30 mL) of intermediate M (3.00 g, 3.01 mmol) at -78 °C, and the mixture was stirred at 70 °C for 30 minutes. The reaction mixture was cooled to -78 °C, boron tribromide (3.77 g, 15.1 mmol) was added, and the mixture was stirred at room temperature for 1 hour. N,N-diisopropylethylamine (3.89 g, 30.1 mmol) and o-dichlorobenzene were then added, and the mixture was stirred at 160 °C for 14 hours. The mixture was returned to room temperature, filtered through Celite, and the solvent in the filtrate was distilled off. The residue was purified by silica gel column chromatography (toluene:hexane = 1:3) and recrystallized from dichloromethane and acetonitrile to obtain compound 1931 (88.1 mg, 0.0934 mmol, 3% yield) as a purple solid. 1 H NMR (400 MHz, CDCl3, δ) : 8.59-8.55 (m, 2H), 8.45-8.41 (m, 4H), 8.23 ​​(d, J= 8.0 Hz, 2H), 7.95 (d, J = 8.0 Hz, 2H), 7.58-7.54 (m, 4H), 7.50-7.43 (m, 4H), 7.39-7.30 (m, 10H), 7.26-7.24 (m, 8H), 7.08 (t, J = 8.0 Hz, 4H). MS (ASAP): 943.55 (M+H)+ ). Calcd for. C 66 H 44 B2N4O2: 942.33

[0154] (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 Compounds 120 and H1 were evaporated from different evaporation sources under conditions of less than 100 Pa to form a thin film with a compound 120 concentration of 0.5 wt % and a thickness of 100 nm. The photoluminescence quantum yield (PLQY) of the formed thin film was measured, and a high value of 86% was observed. The maximum emission wavelength was 612 nm, and the half-width was 38 nm. Furthermore, a thin film was formed using the same procedure using compound 4 instead of compound 120, and measurement was performed. The photoluminescence quantum yield (PLQY) was a high value of 92%. The maximum emission wavelength was 615 nm, and the half-width was 39 nm.

[0155] (Example 2) Fabrication and Evaluation of Organic Electroluminescence Device Each thin film was formed on a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 100 nm was formed by vacuum deposition at a vacuum degree of 1×10 －５The layers were laminated at 100 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 30 nm, TrisPCz was further formed to a thickness of 10 nm, and H1 was further formed to a thickness of 5 nm. Next, H1, T64, and Compound 120 were co-deposited from different evaporation sources to form a 40 nm thick light-emitting layer. The contents of H1, T64, and Compound 120 were 64.5 mass%, 35.0 mass%, and 0.5 mass%, respectively. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different evaporation sources to form a 30 nm thick layer. The contents of Liq and SF3-TRZ in this layer were 30 mass% and 70 mass%, respectively. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing an organic electroluminescence device. When a current was applied to the fabricated organic electroluminescence device, light emission was observed. Of the materials contained in the light-emitting layer, the amount of light emitted from Compound 120 was the largest. The S value of the light-emitting layer of Compound 120 was measured and found to be -0.4, confirming high orientation.

[0156] Example 3: Fabrication and evaluation of another organic electroluminescence device An organic electroluminescence device of Example 3 was fabricated by the same procedure as in Example 2, except that T153 was used instead of T64 used in forming the light-emitting layer. The S value of the light-emitting layer of Compound 120 was measured and found to be −0.4, confirming that Compound 120 had high orientation.

[0157] Example 4: Fabrication and evaluation of another organic electroluminescence device An organic electroluminescence device of Example 4 was fabricated by the same procedure as in Example 3, except that Compound 4 was used instead of Compound 120 used in forming the light-emitting layer. The S value of the light-emitting layer of Compound 4 was measured and found to be −0.25, confirming that Compound 4 had high alignment.

[0158] Instead of Compound 120 and Compound 4, a compound represented by general formula (1) other than these can be used to prepare a thin film and an organic electroluminescence device in the same manner as in Examples 1 to 3.

[0159]

[0160] The compound represented by the general formula (1) has good light-emitting performance. Therefore, by using the compound represented by the general formula (1), an excellent organic light-emitting device can be provided. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): [In the general formula (1), X １ and X ２ represents O. Y １ and Y ２ are each independently a single bond, O, S or C(R ａ ) (R ｂ ) represents R １ ~R ２２ , R ａ , R ｂ each independently represents a hydrogen atom, a deuterium atom, or a substituent; , R １ ~R ２２ At least one of is a substituent. R 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 R １０ , 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 １ ９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ are bonded to each other to form a ring structure Good. ２１ and R １ , R ４ and R ５ , R １０ and R １２ , R １５ and R １６ are combined with each other It does not form a ring structure. C-R in general formula (1) 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 substituted with N.

2. R １ ~R ２２ is selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group, and an aryl group. A group consisting of one or more selected groups (including some of the hydrogen atoms in the group) may all be substituted with deuterium atoms), or substituted or unsubstituted diaryl An amino group (two aryl groups constituting a diarylamino group are linked to each other by a linking group) 2. The compound of claim 1, wherein

3. R １ ~R ２２ At least one of the groups is a deuterium atom, an alkyl group, and an aryl group.

2. The aryl group according to claim 1, wherein the aryl group is an aryl group optionally substituted with one or more groups selected from the group consisting of: compound.

4. R ６ , R ９ , R １７ , R ２０ The compound of claim 1 , wherein is a substituent.

5. R １ ~R ２２ Among them, R ２ , R ３ , R ６ , R ９ , R １３ , R １４ , R １７ , R ２０ from 2. The compound of claim 1, wherein only 1 to 6 selected from the group consisting of are substituents.

6. R １ ~R ２２ The compound according to claim 1, wherein the total number of carbon atoms is 10 to 60.

7. R １ ~R ２２ The compound according to claim 1, wherein the total number of benzene rings is 2 to 6.

8. Y １ and Y ２ The compound of claim 1 , wherein is a single bond.

9. The compound according to claim 1, which has a point-symmetric structure.

10. A light-emitting material comprising the compound according to any one of claims 1 to 9.

11. A film comprising the compound according to any one of claims 1 to 9.

12. An organic semiconductor device comprising the compound according to any one of claims 1 to 9.

13. An organic light-emitting device comprising the compound according to any one of claims 1 to 9.

14. 14. The device according to claim 13, wherein the device has a layer including the compound, the layer also including a host material. The organic light-emitting element according to claim 1.

15. The layer containing the compound contains a delayed fluorescent material in addition to the host material, and 10. The compound according to claim 1, wherein the lowest excited singlet energy is lower than that of the host material and higher than that of the compound.

5. The organic light-emitting element according to claim 4.

16. The element has a layer containing the compound, and the layer has a structure different from that of the compound. The organic light-emitting device of claim 13 , further comprising a light-emitting material that

17. The compound according to claim 13, wherein the compound emits the maximum amount of light among the materials contained in the element. The organic light-emitting device described above.

18. The amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound according to claim 16 . Organic light-emitting devices.

19. The organic light-emitting device according to claim 13, which emits delayed fluorescence.

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