Compound, Light-Emitting Material, and Light-Emitting Element

Abstract

A compound represented by the general formula herein is an excellent light-emitting material. R1 to R5 each represent a hydrogen atom, a deuterium atom, or a substituent other than a cyano group, with at least one among R1 to R5 being an alkyl group and at least one among R1 to R5 being a condensed-ring indol-1-yl group.

Description

Technical Field

[0001] The present invention relates to a compound useful as a light-emitting material and a light-emitting device using the same.

Background Art

[0002] Research has been actively conducted to improve the luminous efficiency of light-emitting devices such as organic electroluminescence devices (organic EL devices). In particular, various efforts have been made to improve the luminous efficiency by newly developing and combining an electron transport material, a hole transport material, a light-emitting material, etc. constituting the organic electroluminescence device. Among them, research on organic electroluminescence devices using a delayed fluorescence material can also be seen.

[0003] A delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after generating reverse intersystem crossing from the excited triplet state to the excited singlet state in the excited state. Fluorescence by such a path is observed later than fluorescence from the excited singlet state directly generated from the ground state (normal fluorescence), and thus is called delayed fluorescence. Here, for example, when a luminescent compound is excited by carrier injection, the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%. Therefore, there is a limit to the improvement of the luminous efficiency only with fluorescence from the directly generated excited singlet state. On the other hand, in a delayed fluorescence material, not only the excited singlet state but also the excited triplet state can be used for fluorescence emission through the above-mentioned reverse intersystem crossing path, so that a higher luminous efficiency can be obtained compared with a normal fluorescence material.

[0004] Since such a principle was clarified, various delayed fluorescence materials have been discovered through various studies. Among them, many compounds in which a donor group is substituted for cyanobenzene are included. As a typical compound, cyanobenzene substituted with a carbazol-9-yl group as follows has been proposed (see Patent Document 1).

[0005]

Chemical Formula

[0006] [Non-Patent Document 1] WO2016 / 202251A1 [Summary of the Invention] [Problems to be Solved by the Invention]

[0007] However, a material that emits delayed fluorescence is not immediately useful as a luminescent material. For example, the above compound described in Patent Document 1 has a problem that the delayed fluorescence lifetime (τ2) becomes long. When trying to shorten the delayed fluorescence lifetime, the emission wavelength tends to shift to a longer wavelength. Therefore, it is not easy to shorten the delayed fluorescence lifetime while maintaining color purity. In addition, since the relationship between the chemical structure and the luminescent properties has not been fully elucidated, it is not easy to generalize the chemical structure of useful luminescent materials.

[0008] Under such circumstances, the present inventors have conducted extensive research with the aim of providing a more useful compound as a luminescent material for light-emitting elements. Then, they have intensively studied to derive and generalize the general formula of a more useful compound as a luminescent material. [Means for Solving the Problems]

[0009] As a result of intensive studies to achieve the above object, the present inventors have found that a cyanobenzene compound having a structure satisfying specific conditions is useful as a luminescent material. The present invention has been proposed based on such findings, and specifically, has the following configuration.

[0010] [1] A compound represented by the following general formula (1). [Chemical Formula] [In general formula (1), R1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, or a substituent other than a cyano group. However, among R 1 ~R 5 at least one is an alkyl group, and among R 1 ~R 5 at least one is a substituted or unsubstituted ring-fused indol-1-yl group. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 may be bonded to each other to form a cyclic structure.] [2] The compound according to [1], wherein the substituted or unsubstituted ring-fused indol-1-yl group is a substituted or unsubstituted ring-fused carbazol-9-yl group. [3] The compound according to [1], wherein the substituted or unsubstituted ring-fused indol-1-yl group is a ring-fused carbazol-9-yl group substituted with a substituent. [4] The compound according to [1], wherein the substituted or unsubstituted ring-fused indol-1-yl group is a ring-fused carbazol-9-yl group substituted with an aryl group or a heteroaryl group. [5] The compound according to [1], wherein the substituted or unsubstituted ring-fused indol-1-yl group is a ring-fused carbazol-9-yl group substituted with an aryl group. [6] The compound according to any one of [1] to [5], wherein the substituted or unsubstituted ring-fused indol-1-yl group is a carbazol-9-yl group condensed with a ring having as ring skeleton constituent atoms one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom. [7] The compound according to any one of [1] to [5], wherein the substituted or unsubstituted ring-fused indol-1-yl group is a carbazol-9-yl group condensed with a ring having as ring skeleton constituent atoms one or more atoms selected from the group consisting of an oxygen atom and a sulfur atom. [8] R 1 ~R 5 ​​​​Two to four of them are substituted or unsubstituted ring-fused indol-1-yl groups, and there are two or more kinds of these two to four substituted or unsubstituted ring-fused indol-1-yl groups, a compound according to any one of [1] to [7]. [9] One of the two or more kinds is a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms is condensed, and the other one is a carbazol-9-yl group in which no ring is condensed, a compound according to [8].

[10] One of the two or more kinds is a substituted or unsubstituted carbazol-9-yl group, and the other one is a carbazol-9-yl group substituted with a substituent different from the substituted or unsubstituted carbazol-9-yl group, a compound according to [8] or [9].

[11] R 1 ~R 5 Four of them are substituted or unsubstituted carbazol-9-yl groups, a compound according to any one of [1] to

[10] , wherein one of R 1 ~R 5 is an alkyl group.

[12] R 1 ~R 5 are each independently a hydrogen atom, a deuterium atom, an alkyl group, or a substituted or unsubstituted ring-fused indol-1-yl group, a compound according to any one of [1] to

[11] .

[13] A compound according to any one of [1] to

[12] , having a line-symmetric structure.

[14] Only R 3 is an alkyl group, a compound according to any one of [1] to

[13] .

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

[14] .

[16] A delayed phosphor comprising a compound according to any one of [1] to

[14] .

[17] A film containing a compound according to any one of [1] to

[14] .

[18] An organic semiconductor device containing a compound according to any one of [1] to

[14] .

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

[14] .

[20] The organic light-emitting device according to

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

[21] The organic light-emitting device according to

[20] , wherein the layer containing the compound further contains a delayed fluorescence material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound.

[22] The organic light-emitting device according to

[20] , wherein the device has a layer containing the compound, and the layer also contains a luminescent material having a structure different from that of the compound.

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

[20] to

[22] , wherein among the materials contained in the device, the amount of light emission from the compound is the largest.

[24] The organic light-emitting device according to

[22] , wherein the amount of light emission from the luminescent material is more than the amount of light emission from the compound.

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

[19] to

[24] , which is an organic electroluminescence device.

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

[19] to

[24] , which emits delayed fluorescence.

Advantages of the Invention

[0011] The compounds of the present invention are useful as luminescent materials. Further, among the compounds of the present invention, there are compounds having a short delayed fluorescence lifetime and emitting light at a short wavelength. Furthermore, among the organic light-emitting devices using the compounds of the present invention, there are devices having high luminous efficiency.

Brief Description of the Drawings

[0012]

Figure 1

Embodiments for Carrying Out the Invention

[0013] Hereinafter, the content of the present invention will be described in detail. The description of the constituent elements described below may be based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In this specification, a numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. In addition, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention can be substituted with deuterium atoms ( 2 H, deuterium D). In the chemical structural formulas in this specification, a hydrogen atom is represented as H or the representation is omitted. For example, when the representation of the atoms bonded to the ring skeleton constituent carbon atoms of a benzene ring is omitted, it is assumed that H is bonded to the ring skeleton constituent carbon atoms at the positions where the representation is omitted. In the chemical structural formulas in this specification, a deuterium atom is represented as D.

[0014] [Compound represented by general formula (1)] [Chemical formula]

[0015] In general formula (1), R 1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, or a substituent other than a cyano group. R 1 ~R 5 At least one of them is an alkyl group. In one aspect of the present invention, at least R 1 is an alkyl group. In one aspect of the present invention, at least R 2 is an alkyl group. In one aspect of the present invention, at least R 3 is an alkyl group. R 1 ~R 5 The number of those that are alkyl groups is 1 to 4. In one aspect of the present invention, 4 of R 1 ~R 5 are alkyl groups. In one aspect of the present invention, 3 of R 1 ~R 5 are alkyl groups. For example, R 1 , R3 and R 5 is an alkyl group. For example, R 2 and R 3 and R 4 is an alkyl group. For example, R 1 and R 2 and R 3 is an alkyl group. For example, R 1 and R 2 and R 4 is an alkyl group. For example, R 1 and R 3 and R 4 is an alkyl group. In one aspect of the present invention, R 1 to R 5 Among them, two are alkyl groups. For example, R 1 and R 2 are alkyl groups. For example, R 1 and R 3 are alkyl groups. For example, R 1 and R 4 are alkyl groups. For example, R 1 and R 5 are alkyl groups. For example, R 2 and R 3 are alkyl groups. For example, R 2 and R 4 are alkyl groups. In one aspect of the present invention, R 1 to R 5 Among them, only one is an alkyl group. R 1 to R 5The alkyl group that can be adopted may be linear, branched, or cyclic. Also, two or more of the linear part, cyclic part, and branched part may be mixed. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, 4 or less. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, preferably methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, and for example, methyl group. R 1 ~R 5 The alkyl group that can be adopted is an unsubstituted alkyl group. However, some or all of the hydrogen atoms of the alkyl group may be substituted with deuterium atoms. In a preferred embodiment of the present invention, the alkyl group is a methyl group (CH3) or a deuterated methyl group (CD3).

[0016] In general formula (1), at least one of R 1 ~R 5 is a substituted or unsubstituted ring-fused indol-1-yl group. Hereinafter, the "substituted or unsubstituted ring-fused indol-1-yl group" is referred to as an IDL group. In one embodiment of the present invention, at least R 5 is an IDL group. In one embodiment of the present invention, at least R 4 is an IDL group. In one embodiment of the present invention, at least R 3 is an IDL group. R 1 ~R 5 The number of those which are IDL groups among R 1 ~R 5 is 1 to 4. In one embodiment of the present invention, 4 of R 1 ~R 5 are IDL groups. For example, R1 , R 3 , R 5 is an IDL group. For example, R 2 , R 3 , R 4 is an IDL group. For example, R 3 , R 4 , R 5 is an IDL group. For example, R 2 , R 4 , R 5 is an IDL group. For example, R 2 , R 3 , R 5 is an IDL group. In one aspect of the present invention, two of R 1 to R 5 are IDL groups. For example, R 4 and R 5 are IDL groups. For example, R 3 and R 5 are IDL groups. For example, R 2 and R 5 are IDL groups. For example, R 1 and R 5 are IDL groups. For example, R 3 and R 4 are IDL groups. For example, R 2 and R 4 are IDL groups. In one aspect of the present invention, only one of R 1 to R 5 is an IDL group. In one aspect of the present invention, R 3 is an alkyl group, and at least R 5 is an IDL group. In one aspect of the present invention, R 3 is an alkyl group, and at least R 4 is an IDL group. In one aspect of the present invention, R 3 is an alkyl group, and at least R 4 and R 5 are IDL groups. In one aspect of the present invention, R 3 is an alkyl group, and at least R 2 and R 5 are IDL groups. In one aspect of the present invention, R 3 is an alkyl group, and at least R 1 and R 5is an IDL group. In one aspect of the present invention, R 3 is an alkyl group, and at least R 1 and R 4 and R 5 are IDL groups. In one aspect of the present invention, R 3 is an alkyl group, and at least R 2 and R 4 and R 5 are IDL groups. In one aspect of the present invention, R 3 is an alkyl group, and R 1 and R 2 and R 4 and R 5 are IDL groups. In one aspect of the present invention, R 2 is an alkyl group, and at least R 5 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and at least R 4 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and at least R 3 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and at least R 1 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and at least R 4 and R 5 are IDL groups. In one aspect of the present invention, R 2 is an alkyl group, and at least R 3 and R 5 are IDL groups. In one aspect of the present invention, R 2 is an alkyl group, and at least R 1 and R 5 are IDL groups. In one aspect of the present invention, R 2 is an alkyl group, and at least R 3 and R 4 are IDL groups. In one aspect of the present invention, R 2 is an alkyl group, and at least R 1 and R 4 are IDL groups. In one aspect of the present invention, R 2 is an alkyl group, and at least R1 and R 3 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and at least R 3 and R 4 and R 5 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and at least R 1 and R 4 and R 5 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and at least R 1 and R 3 and R 4 is an IDL group. In one aspect of the present invention, R 2 is an alkyl group, and R 1 and R 3 and R 4 and R 5 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 5 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 4 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 3 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 2 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 4 and R 5 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 3 and R 5 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 2 and R 5 is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 3 and R 4is an IDL group. In one aspect of the present invention, R 1 is an alkyl group, and at least R 2 and R 4 are IDL groups. In one aspect of the present invention, R 1 is an alkyl group, and at least R 2 and R 3 are IDL groups. In one aspect of the present invention, R 1 is an alkyl group, and at least R 3 and R 4 and R 5 are IDL groups. In one aspect of the present invention, R 1 is an alkyl group, and at least R 2 and R 4 and R 5 are IDL groups. In one aspect of the present invention, R 1 is an alkyl group, and at least R 2 and R 3 and R 4 are IDL groups. In one aspect of the present invention, R 1 is an alkyl group, and R 2 and R 3 and R 4 and R 5 are IDL groups.

[0017] The IDL group has a ring-fused indole structure in which a ring is fused to indole. Indole has a structure in which a benzene ring and a pyrrole ring are fused, but it is preferable that at least one more ring is fused to the pyrrole ring. In one aspect of the present invention, the ring is fused only to the pyrrole ring. In one aspect of the present invention, the ring is fused to the pyrrole ring and the benzene ring, respectively. The fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or a ring in which these are further fused. Preferably, they are an aromatic hydrocarbon ring and an aromatic heterocyclic ring. Examples of the aromatic hydrocarbon ring include a substituted or unsubstituted benzene ring. Another benzene ring may be further fused to the benzene ring, or a heterocyclic ring such as a pyridine ring may be fused. The aromatic heterocyclic ring means a ring having aromaticity containing a heteroatom as a ring skeleton constituting atom, and is preferably a 5- to 7-membered ring. For example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, a thiophene ring, and a pyrrole ring can be adopted as the aromatic heterocyclic ring. In one aspect of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. It should be noted that a substituent selected from the substituent group E is preferably bonded to the nitrogen atom of the pyrrole ring, and an aryl group which may be substituted with an alkyl group or an aryl group is more preferably substituted.

[0018] In one aspect of the present invention, the IDL group is a substituted or unsubstituted ring-fused carbazol-9-yl group. In one aspect of the present invention, the IDL group is a ring-fused carbazol-9-yl group substituted with a substituent. In one aspect of the present invention, the IDL group is a ring-fused carbazol-9-yl group substituted with an aryl group. In one aspect of the present invention, the IDL group is a ring-fused carbazol-9-yl group substituted with a heteroaryl group. In one aspect of the present invention, the IDL group is a carbazol-9-yl group having a ring condensed with one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms. In one aspect of the present invention, the IDL group is a carbazol-9-yl group having a ring condensed with one or more atoms selected from the group consisting of an oxygen atom and a sulfur atom as ring skeleton constituent atoms. R 1 ~R 5 When two to four of them are IDL groups, the two to four IDL groups may all be the same or different. In one aspect of the present invention, R 1 ~R 5 Among them, two to four are IDL groups, and the two to four IDL groups are composed of two or more types of IDL groups. For example, there may be two types. In one aspect of the present invention, when two or more types of IDL groups are present, one of them is a carbazol-9-yl group having a ring condensed with one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms, and the other is a carbazol-9-yl group without a condensed ring. In one aspect of the present invention, when two or more types of IDL groups are present, one of them is a substituted or unsubstituted carbazol-9-yl group, and the other is a different substituted or unsubstituted carbazol-9-yl group.

[0019] The IDL group is preferably a group represented by the following general formula (2).

Chemical formula

[0020] In general formula (2), Z 1 is C-R 11represents O or N, and Z 2 represents C-R 12 represents O or N, and Z 3 represents C-R 13 represents O or N, and Z 4 represents C-R 14 represents O or N. Ar represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocyclic ring. R 11 and R 12 , R 12 and R 13 , R 13 and R 14 may be bonded to each other to form a cyclic structure.

[0021] Z 1 to Z 4 Among them, the number of N is preferably 0 to 3, and preferably 0 to 2. In one aspect of the present invention, Z 1 to Z 4 Among them, the number of N is 1. In one aspect of the present invention, Z 1 to Z 4 Among them, the number of N is 0. R 11 to R 14 each independently represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected, for example, from among the substituent group A, or from among the substituent group B, or from among the substituent group C, or from among the substituent group D, or from among the substituent group E. When two or more of R 11 to R 14 represent substituents, these two or more substituents may be the same or different. It is preferable that 0 to 2 of R 11 to R 14 are substituents. For example, one may be a substituent, or 0 may be a substituent (R 11 to R 14 is a hydrogen atom or a deuterium atom). R 11 and R 12 , R 12 and R 13 , R 13 and R 14They may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring thereof. Preferably, it is an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Examples of the aromatic hydrocarbon ring include a substituted or unsubstituted benzene ring. Another benzene ring may be further condensed to the benzene ring, or a heterocyclic ring such as a pyridine ring may be condensed. The aromatic heterocyclic ring means a ring showing aromaticity containing a hetero atom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring. For example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the aromatic heterocyclic ring. In a preferred aspect of the present invention, the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. Here, benzofuran, benzothiophene, and indole may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E. It is preferable that a substituted or unsubstituted aryl group is bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of the substituent include a substituent selected from any of the substituent groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R 11 and R 12 , R 12 and R 13 , R 13 and R 14 in one set are bonded to each other to form a cyclic structure. In one aspect of the present invention, R 11 and R 12 , R 12 and R 13 , R 13 and R 14 are not bonded to each other to form a cyclic structure.

[0022] In general formula (2), Ar represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocyclic ring. In one aspect of the present invention, Ar is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocyclic ring. In one aspect of the present invention, Ar is a substituted or unsubstituted aromatic heterocyclic ring. Examples of the aromatic hydrocarbon ring that Ar can take include a benzene ring. Another benzene ring may be further condensed with the benzene ring, or a heterocyclic ring such as a pyridine ring may be condensed. The aromatic heterocyclic ring that Ar can take is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring can be adopted as the aromatic heterocyclic ring. In one aspect of the present invention, the aromatic heterocyclic ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, a pyridine ring of substituted or unsubstituted quinoline, or a pyridine ring of substituted or unsubstituted isoquinoline. Here, benzofuran, benzothiophene, quinoline, and isoquinoline may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E.

[0023] The IDL group is preferably a group represented by the following general formula (3).

Chemical formula

[0024] In general formula (3), Z 1 represents C-R 11 or N, and Z 2 represents C-R 12 or N, and Z 3 represents C-R13 represents O or N, and Z 4 is C-R 14 represents O or N, and Z 6 is C-R 16 represents O or N, and Z 7 is C-R 17 represents O or N, and Z 8 is C-R 18 represents O or N, and Z 9 is C-R 19 represents O or N. R 11 and R 12 、R 12 and R 13 、R 13 and R 14 、R 16 and R 17 、R 17 and R 18 、R 18 and R 19 may be bonded to each other to form a cyclic structure. Z in the general formula (3) 1 ~Z 4 、R 11 ~R 14 For these, the corresponding description of the general formula (2) can be referred to. Z in the general formula (3) 6 ~Z 9 、R 16 ~R 19 corresponds in order to Z 1 ~Z 4 、R 11 ~R 14 in the general formula (2), and for the descriptions of these, the description of Z 1 ~Z 4 、R 11 ~R 14 in the general formula (2) can be referred to. In one aspect of the present invention, among Z 1 ~Z 4 、Z 6 ~Z 9 the number of those which are N is preferably 0 to 2, and preferably 0 or 1. In one aspect of the present invention, among Z 1 ~Z 4 、Z 6 ~Z 9 the number of those which are N is 1. In a preferred aspect of the present invention, Z1 ~Z 4 , Z 6 ~Z 9 Among them, the number of those that are N is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group may be unsubstituted, may be substituted with a substituent selected from substituent group A, may be substituted with a substituent selected from substituent group B, may be substituted with a substituent selected from substituent group C, may be substituted with a substituent selected from substituent group D, or may be substituted with a substituent selected from substituent group E. Preferably, it is a case where it is substituted with an aryl group, and it is superior in terms of luminous efficiency and device lifetime compared to the case where it is substituted with a heteroaryl group. In a preferred embodiment of the present invention, the IDL group is a carbazol-9-yl group substituted with a group containing at least one substituted or unsubstituted aryl group. For example, it is a carbazol-9-yl group substituted with at least one substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one of the 2-position and the 7-position is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one of the 3-position and the 6-position is a substituted or unsubstituted aryl group. The aryl group referred to here may be unsubstituted, may be substituted with a substituent selected from substituent group A, may be substituted with a substituent selected from substituent group B, may be substituted with a substituent selected from substituent group C, may be substituted with a substituent selected from substituent group D, or may be substituted with a substituent selected from substituent group E.

[0025] The IDL group is a substituted or unsubstituted indol-1-yl group, and a ring is condensed to the indole ring constituting the indol-1-yl group, thereby forming a condensed ring having 3 or more rings. In the present specification, a group satisfying this condition is referred to as a "ring-condensed indol-1-yl group".

[0026] The ring-condensed indol-1-yl group may have one monocyclic ring, one polycyclic ring, or two or more polycyclic or monocyclic rings condensed to the benzene ring or pyrrole ring that constitutes the indol-1-yl group. For example, when two rings are condensed, it is preferable that one is condensed to the benzene ring and one is condensed to the pyrrole ring. The two condensed rings may be the same or different. Condensation of a ring to the indole ring may form a condensed ring having 4 or more, 5 or more, 6 or more rings, and it is preferable to form a condensed ring having 5 or more rings. For example, a compound forming a condensed ring having 4 rings, a compound forming a condensed ring having 5 rings, a compound forming a condensed ring having 6 rings, a compound forming a condensed ring having 7 rings, or a compound forming a condensed ring having 8 rings may be employed. The ring may be condensed only at the 2,3-position (b) of the indole ring, only at the 4,5-position (e), only at the 5,6-position (f), only at the 6,7-position (g), or may be condensed at both the 4,5-position (e) and the 6,7-position (g). Further, it may be condensed with any one of the 4,5-position (e), 5,6-position (f), and 6,7-position (g) and the 2,3-position (b) (see the following formula, * represents the bonding position).

Chemical formula

[0027] The ring directly condensed to the benzene ring or pyrrole ring that constitutes the indol-1-yl group (when the condensed ring is a polycyclic ring, it refers only to the ring directly condensed among the rings constituting the polycyclic ring) may be any of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring. Preference is given to the case where one or more rings selected from the group consisting of a benzene ring and an aromatic heterocyclic ring are directly condensed. The heterocyclic ring referred to herein is a ring containing a heteroatom. The heteroatom is preferably selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom, and more preferably selected from an oxygen atom, a sulfur atom, and a nitrogen atom. In a preferred embodiment, the heteroatom is an oxygen atom. In another preferred embodiment, the heteroatom is a sulfur atom. In still another preferred embodiment, the heteroatom is a nitrogen atom. The number of heteroatoms included as ring skeleton constituent atoms of the heterocyclic ring is one or more, preferably 1 to 3, and more preferably 1 or 2. In a preferred embodiment, the number of heteroatoms is 1. When the number of heteroatoms is two or more, they are preferably the same kind of heteroatom, but may also be composed of different kinds of heteroatoms. For example, all of two or more heteroatoms may be nitrogen atoms. Ring skeleton constituent atoms other than the heteroatom are carbon atoms. The number of ring skeleton constituent atoms of the heterocyclic ring directly condensed to the benzene ring constituting the indol-1-yl group is preferably 4 to 8, more preferably 5 to 7, and even more preferably 5 or 6. In a preferred embodiment, the number of ring skeleton constituent atoms constituting the heterocyclic ring is 5. It is preferable that there are two or more conjugated double bonds in the heterocyclic ring, and it is preferable that the conjugated system of the indole ring is extended by the condensation of the heterocyclic ring (that is, it preferably has aromaticity). Preferred examples of the heterocyclic ring include a furan ring, a thiophene ring, and a pyrrole ring. Another ring may be further condensed to the ring directly condensed to the benzene ring or pyrrole ring constituting the indol-1-yl group. Further, the ring to be condensed may be a monocyclic ring or a condensed ring. Examples of the ring to be condensed include an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring. In a preferred embodiment of the present invention, at least one heterocyclic ring is directly condensed to the benzene ring or pyrrole ring constituting the indol-1-yl group. In a preferred embodiment of the present invention, the condensed ring constituting the ring-condensed indol-1-yl group contains two or more heterocyclic rings. For example, the case of containing two heterocyclic rings or the case of containing three heterocyclic rings can be exemplified.

[0028] Examples of the aromatic hydrocarbon ring in this specification include a benzene ring. Examples of the aromatic heterocyclic ring include a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a pyrrole ring, a pyrazole ring, and an imidazole ring. Examples of the aliphatic hydrocarbon ring include a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. Examples of the aliphatic heterocyclic ring include a piperidine ring, a pyrrolidine ring, and an imidazoline ring. Specific examples of the condensed ring include a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyran ring, a tetracene ring, an indole ring, an isoindole ring, a benzimidazole ring, a benzotriazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, and a cinnoline ring.

[0029] In a preferred embodiment of the present invention, the ring-fused indol-1-yl group is a benzofuran-fused indol-1-yl group, a benzothiophene-fused indol-1-yl group, an indole-fused indol-1-yl group, or a silainden-fused indol-1-yl group. In a more preferred embodiment of the present invention, the indol-1-yl group is a benzofuran-fused indol-1-yl group, a benzothiophene-fused indol-1-yl group, or an indole-fused indol-1-yl group.

[0030] In the present invention, as the benzofuran-fused indol-1-yl group, a substituted or unsubstituted benzofuro[2,3-e]indol-1-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[3,2-e]indol-1-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[2,3-f]indol-1-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[3,2-f]indol-1-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[2,3-g]indol-1-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[3,2-g]indol-1-yl group can be adopted. The condensed ring constituting these groups may or may not have an additional ring condensed thereto. In the present invention, as the benzofuran-fused indol-1-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazol-9-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[2,3-b]carbazol-9-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[3,2-b]carbazol-9-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[2,3-c]carbazol-9-yl group can be adopted. Also, a substituted or unsubstituted benzofuro[3,2-c]carbazol-9-yl group can be adopted. In the condensed rings constituting these groups, further rings may or may not be condensed. As the preferable benzofuran-fused indol-1-yl group, groups having any of the following structures can be mentioned. The hydrogen atoms in the following structures may or may not be substituted. For example, those substituted with an aryl group such as a phenyl group or those in which the 3-position of the carbazole ring is substituted can be preferably exemplified. Also, in the benzene ring in the following structures, further rings may or may not be condensed. The wavy line represents the bonding position.

Chemical formula

[0031] A carbazol-9-yl group in which two benzofuran rings are condensed at the 2,3-positions can also be adopted. Specifically, it is a group having any of the following structures. The hydrogen atoms in the following structures may or may not be substituted. Also, in the benzene ring in the following structures, further rings may or may not be condensed.

Chemical formula

[0032] In the present invention, as the benzothiophene-fused indole-1-yl group, a substituted or unsubstituted benzothieno[2,3-e]indole-1-yl group can be employed. Further, a substituted or unsubstituted benzothieno[3,2-e]indole-1-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[2,3-f]indole-1-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[3,2-f]indole-1-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[2,3-g]indole-1-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[3,2-g]indole-1-yl group can also be employed. The condensed ring constituting these groups may or may not have an additional ring condensed thereto. In the present invention, as the benzothiophene-fused indole-1-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be employed. Further, a substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be employed. The condensed ring constituting these groups may or may not have an additional ring condensed thereto. Preferred benzothiophene-fused indole-1-yl groups include groups having any of the following structures. The hydrogen atoms in the following structures may or may not be substituted. For example, those substituted with an aryl group such as a phenyl group or those in which the 3-position of the carbazole ring is substituted can be preferably exemplified. Further, the benzene ring in the following structures may or may not have an additional ring condensed thereto. [Chemical formula]

[0033] A carbazol-9-yl group in which two benzothiophene rings are condensed at the 2- and 3-positions can also be employed. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may or may not be substituted. Further, in the benzene ring in the following structures, a ring may or may not be further condensed.

Chemical formula

[0034] In the present invention, as the indole-condensed indol-1-yl group, a substituted or unsubstituted indolo[2,3-e]indol-1-yl group can be employed. Further, a substituted or unsubstituted indolo[3,2-e]indol-1-yl group can also be employed. Further, a substituted or unsubstituted indolo[2,3-f]indol-1-yl group can also be employed. Further, a substituted or unsubstituted indolo[3,2-f]indol-1-yl group can also be employed. Further, a substituted or unsubstituted indolo[2,3-g]indol-1-yl group can also be employed. Further, a substituted or unsubstituted indolo[3,2-g]indol-1-yl group can also be employed. In the condensed rings constituting these groups, a ring may or may not be further condensed. In the present invention, as the indole-condensed indol-1-yl group, a substituted or unsubstituted indolo[2,3-a]carbazol-9-yl group can be employed. Also, a substituted or unsubstituted indolo[3,2-a]carbazol-9-yl group can be employed. Also, a substituted or unsubstituted indolo[2,3-b]carbazol-9-yl group can be employed. Also, a substituted or unsubstituted indolo[3,2-b]carbazol-9-yl group can be employed. Also, a substituted or unsubstituted indolo[2,3-c]carbazol-9-yl group can be employed. Also, a substituted or unsubstituted indolo[3,2-c]carbazol-9-yl group can be employed. In the condensed rings constituting these groups, further rings may or may not be condensed. Preferred indole-condensed indol-1-yl groups include groups having any of the following structures. The hydrogen atoms in the following structures may or may not be substituted. For example, those substituted with an aryl group such as a phenyl group or those in which the 3-position of the carbazole ring is substituted can be preferably exemplified. Also, in the benzene rings in the following structures, further rings may or may not be condensed.

Chemical formula

[0035] In a preferred embodiment of the present invention, the benzofuran-fused indol-1-yl group, benzothiophene-fused indol-1-yl group, indole-fused indol-1-yl group, and silaindene-fused indol-1-yl group are substituted with a substituted or unsubstituted aryl group. Preferably, they are substituted with a substituted or unsubstituted phenyl group. As the substituents of the aryl group or phenyl group mentioned herein, a group selected from any of the substituent groups A to E can be selected, and preferably a group selected from the substituent group E can be selected. Also, it is preferable that the aryl group or phenyl group mentioned herein is unsubstituted. In a preferred embodiment of the present invention, the ring-fused indol-1-yl group is a benzofuran-fused indol-1-yl group substituted with a substituted or unsubstituted aryl group.

[0036] Hereinafter, specific examples of the IDL group that can be adopted in the general formula (1) are shown. However, the IDL group that can be adopted in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, D represents a deuterium atom, * indicates the bonding position, and the methyl group is omitted from the display. Therefore, for example, D150 represents a 3-methylcarbazol-9-yl group.

[0037]

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chem.

[0038] R in the general formula (1) 1 ~R 5 Among them, those that are neither a cyano group, an alkyl group, nor an IDL group (hereinafter referred to as "the remaining R 1 ~R 5 ") are a hydrogen atom, a deuterium atom, or a substituent that is neither a cyano group, an alkyl group, nor an IDL group (hereinafter referred to as "the remaining substituent"). The remaining R 1 ~R 5 may all be hydrogen atoms or deuterium atoms. For example, they may all be hydrogen atoms, or for example, they may all be deuterium atoms. Among the remaining R 1 ~R 5 , the number of those that are the remaining substituents is preferably 0 to 3. For example, it may be within the range of 0 to 2, may be 0 or 1, or may be 0. The remaining substituents may be selected from the following substituent group A, may be selected from the following substituent group B, may be selected from the following substituent group C, may be selected from the following substituent group D, or may be selected from the following substituent group E. In one aspect of the present invention, the remaining substituents contain a donor group. In one aspect of the present invention, all of the remaining substituents are donor groups. The donor group referred to here can be selected from among groups having a negative Hammett σp value. The Hammett σp value was proposed by L.P. Hammett and quantifies the influence of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, the following formula that holds between the substituent in a para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp Or log(K / K0) = ρσp It is a constant (σp) specific to the substituent in []. In the above formula, k0 is the rate constant of a benzene derivative having no substituent, k is the rate constant of a benzene derivative substituted with a substituent, K0 is the equilibrium constant of a benzene derivative having no substituent, K is the equilibrium constant of a benzene derivative substituted with a substituent, and ρ represents a reaction constant determined by the type and conditions of the reaction. For the description of the "Hammett's 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). In one aspect of the present invention, the remaining substituents are substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups. In a preferred aspect of the present invention, the other substituents are substituted or unsubstituted aryl groups, for example, phenyl groups which may be substituted with an alkyl group or an aryl group. The "aryl group" and "heteroaryl group" in the present specification may be monocyclic or a condensed ring in which two or more rings are condensed. In the case of a condensed ring, the number of condensed rings is preferably 2 - 6, and can be selected, for example, from 2 - 4. Specific examples of the ring include benzene ring, pyridine ring, pyrimidine ring, triazine ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, quinoline ring, pyrazine ring, quinoxaline ring, naphthyridine ring. Specific examples of the arylene group or heteroarylene group include phenyl group, 1 - naphthyl group, 2 - naphthyl group, 1 - anthracenyl group, 2 - anthracenyl group, 9 - anthracenyl group, 2 - pyridyl group, 3 - pyridyl group, 4 - pyridyl group. The substituents of the aryl group and heteroaryl group may be selected from the following substituent group A, or may be selected from the following substituent group B, or may be selected from the following substituent group C, or may be selected from the following substituent group D, or may be selected from the following substituent group E.

[0039] In one aspect of the present invention, R in the general formula (1) 1 ~R 5 Among them, 3 - 4 are donor groups, and R 1 ~R5 Among them, 1 to 2 are alkyl groups, and the remaining R 1 ~R 5 are hydrogen atoms or deuterium atoms. Preferably, some or all of the donor groups are substituted or unsubstituted carbazol-9-yl groups. In one aspect of the present invention, among 3 to 4 donor groups, there are donor groups with different structures from each other. For example, there are carbazol-9-yl groups with different substitution states, and specifically, a case where a substituted carbazolyl group and an unsubstituted carbazolyl group are mixed can be exemplified. For example, R 1 and R 2 are donor groups with the same structure, and R 4 and R 5 may be donor groups with a structure different from that of R 1 and R 2 . On the other hand, all of the 3 to 4 donor groups may have the same structure. In a preferred aspect of the present invention, R 3 is an alkyl group. In one aspect of the present invention, the donor group has a structure represented by the following general formula (4). R 21 and R 22 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 21 and R 22 may be bonded to each other to form a cyclic structure. L represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. * represents the bonding position to the carbon atom (C) constituting the ring skeleton of the ring in the general formula (1).

Chemical formula

[0040] In the general formula (1), R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5They may be combined with each other to form a cyclic structure. For the description and specific examples of the cyclic structure mentioned here, reference can be made to the description and specific examples of the condensed rings in the above description of "ring condensation". In one embodiment of the present invention, R 1 and R 2 at least one pair of 4 and R 5 are combined with each other to form a cyclic structure. In one embodiment of the present invention, R 2 and R 3 at least one pair of 3 and R 4 are combined with each other to form a cyclic structure. In one embodiment of the present invention, R 1 and R 2 at least one pair of 4 and R 5 are not combined with each other to form a cyclic structure. In one embodiment of the present invention, R 2 and R 3 at least one pair of 3 and R 4 are not combined with each other to form a cyclic structure. In one embodiment of the present invention, R 1 and R 2 at least one pair of 2 and R 3 at least one pair of 3 and R 4 at least one pair of 4 and R 5 are not combined with each other to form a cyclic structure.

[0041] The compound represented by the general formula (1) preferably does not contain a metal atom, and may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. In a preferred embodiment of the present invention, the compound represented by the general formula (1) is composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and an oxygen atom. Further, the compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and a sulfur atom. The compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, and a nitrogen atom. The compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, and a nitrogen atom. Furthermore, the compound represented by the general formula (1) may not contain a hydrogen atom and may be a compound containing a deuterium atom. For example, the compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. In one embodiment of the present invention, the compound represented by the general formula (1) has a symmetric structure. For example, it may have a line-symmetric structure. When it has a line-symmetric structure, R in the general formula (1) 1 and R 5 are the same, and R 2 and R 4 are the same. In one embodiment of the present invention, the compound represented by the general formula (1) has an asymmetric structure.

[0042] As used herein, the "substituent group A" means one group selected from the group consisting of 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 ring skeleton constituent atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton constituent atoms), a heteroarylthio group (e.g., having 5 to 30 ring skeleton constituent atoms), an acyl group (e.g., having 1 to 40 carbon atoms), an alkenyl group (e.g., having 1 to 40 carbon atoms), an alkynyl group (e.g., having 1 to 40 carbon atoms), an alkoxycarbonyl group (e.g., having 1 to 40 carbon atoms), an aryloxycarbonyl group (e.g., having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (e.g., having 1 to 40 carbon atoms), a silyl group (e.g., a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group, or a group formed by combining two or more thereof. As used herein, the "substituent group B" means one group selected from the group consisting of an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy 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), a heteroaryl group (e.g., having 5 to 30 ring skeleton constituent atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton constituent atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms), or a group formed by combining two or more thereof. As used herein, the "substituent group C" means one group selected from the group consisting of an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton constituent atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms), or a group formed by combining two or more thereof. As used herein, the "substituent group D" means one group selected from the group consisting of an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton constituent atoms), or a group formed by combining two or more thereof. As used herein, the "substituent group E" means one group selected from the group consisting of an alkyl group (e.g., having 1 to 20 carbon atoms) and an aryl group (e.g., having 6 to 22 carbon atoms), or a group formed by combining two or more thereof. When the terms "substituent" or "substituted or unsubstituted" are used herein, the substituent may be selected, for example, from among the substituent group A, or from among the substituent group B, or from among the substituent group C, or from among the substituent group D, or from among the substituent group E.

[0043] In Tables 1 to 3 below, specific examples of the compound represented by the general formula (1) are illustrated. However, the compound represented by the 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, the R of the general formula (1) 1 ~R 5 is specified for each compound to individually show the structures of Compounds 1 to 135. In Table 2, the R of a plurality of compounds in each row 1 ~R 5 are collectively shown to indicate the structures of Compounds 1 to 475718. For example, in the row of Compounds 1 to 135 in Table 2, R 2 , R 4 , R 5 are fixed to H (hydrogen atom), R 3 is fixed to CH3 (methyl group), and those in which R 1 is D1 to D135 are sequentially regarded as Compounds 1 to 135. That is, the row of Compounds 1 to 135 in Table 2 is a collective display of the Compounds 1 to 135 specified in Table 1. Similarly, in the row of Compounds 136 to 270 in Table 2, R 1 , R 4 , R 5 are fixed to H (hydrogen atom), R 3 is fixed to CH3 (methyl group), and those in which R 2 is D1 to D135 are sequentially regarded as Compounds 136 to 270. In the same manner, Compounds 237860 to 238129 in Table 2 are also specified. In the range of compounds 271 to 21600, R 2 and R 4 are fixed to H (hydrogen atom), R 3 is fixed to CH3 (methyl group), R 1 is D1 to D135, and R 5 is D1 to D158. Among the non-fixed groups, R 1 taking D1 to D135 is fixed first, and R 5 taking D1 to D158 is sequentially permuted to assign compound numbers. For this reason, those with R 1 being D1 and R 5 being D1 to D158 become compounds 271 to 428 in sequence, those with R 1 being D2 and R 5 being D1 to D158 become compounds 429 to 586 in sequence, those with R 1 being D3 and R 5 being D1 to D158 are assigned compound numbers in the order that they become compounds 587 to 744, and those with R 1 being D135 and R 5 being D1 to D158 become compounds 21443 to 21600 in sequence. According to the same principle, compounds 42931 to 67894 and compounds 238130 to 305753 in Table 2 are also specified. In the range of compounds 67895 to 89224, R 1 is fixed to H (hydrogen atom), R 3 is fixed to CH3 (methyl group), R 2 is D1 to D135, and R 4 and R 5 being the same are grouped and displayed. Those with R 2 being D1 and R 4 and R 5 being D1 to D158 become compounds 67895 to 68052 in sequence, those with R 2 being D2 and R 4 and R 5 being D1 to D158 become compounds 68053 to 68210 in sequence, those with R 2 being D3 and R 4 and R 5 being D1 to D158 are assigned compound numbers in the order that they become compounds 68211 to 68368, and R 2is D135, R 4 and R 5 being D1 to D158 become Compounds 89067 to 89224 in order. In the same manner, Compounds 89225 to 237859 and Compounds 305754 to 475718 in Table 2 are also specified. In Table 3, R 1 ~R 5 of the general formula (1) are specified for each compound to individually show the structures of Compounds 475719 to 475758. In Tables 1 to 3, CD3 represents a methyl group in which three hydrogen atoms are substituted with deuterium atoms, Cy represents a cyclohexyl group, Et represents an ethyl group, iPr represents an isopropyl group, and tBu represents a tert-butyl group.

Table 1

Table 2

Table 3

[0044] Those in which all hydrogen atoms present in the molecules of the above Compounds 1 to 475758 are substituted with deuterium atoms are disclosed as Compounds 1(D) to 475758(D). Among the above specific examples of the compounds, when there are rotational isomers, the mixture of rotational isomers and each separated rotational isomer are also considered to be those disclosed in this specification.

[0045] As other specific examples included in the general formula (1), compounds having the following structures can also be exemplified.

Chemical formula

[0046] In a preferred embodiment of the present invention, the compound represented by the general formula (1) is selected from the following group of compounds.

Chemical formula

[0047] When the compound represented by the general formula (1) is intended to be used, for example, by forming a film of an organic layer containing the compound represented by the general formula (1) by vapor deposition, the molecular weight is preferably 1500 or less, more preferably 1200 or less, still more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1). The compound represented by the general formula (1) may be formed into a film by a coating method regardless of its molecular weight. If the coating method is used, it is possible to form a film even with a compound having a relatively large molecular weight. The compound represented by the general formula (1) has the advantage of being easily soluble in an organic solvent. Therefore, the compound represented by the general formula (1) is easy to apply the coating method and is easy to purify and increase the purity.

[0048] Applying the present invention, it is also conceivable to use a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light-emitting material. For example, it is conceivable to use, as a light-emitting material, a polymer obtained by previously allowing a polymerizable group to be present in the structure represented by the general formula (1) and polymerizing the polymerizable group. For example, a monomer containing a polymerizable functional group at any site of the general formula (1) is prepared, and this is polymerized alone or copolymerized with another monomer to obtain a polymer having a repeating unit, and it is conceivable to use the polymer as a light-emitting material. Alternatively, it is also conceivable to obtain dimers or trimers by coupling compounds having the structure represented by the general formula (1) and use them as light-emitting materials.

[0049] Examples of polymers having repeating units containing the structure represented by the general formula (1) include polymers containing the structure represented by any of the following two general formulas. [Chemical formula]

[0050] In the above general formula, Q represents a group containing the structure represented by the general formula (1), and L 1 and L 2 represent linking groups. 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 preferably has a structure represented by -X 11 -L 11 -. Here, X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. L 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. In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represent a substituent. Preferably, they are 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. The linking groups represented by L 1 and L 2 can be bonded to any site of the general formula (1) constituting Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.

[0051] As a specific structural example of the repeating unit, a structure represented by the following formula can be cited. [Chemical formula]

[0052] A polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of the general formula (1), using it as a linker to react with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group. [Chemical formula]

[0053] A polymer containing a structure represented by the general formula (1) in the molecule may be a polymer composed only of a repeating unit having a structure represented by the general formula (1), or a polymer containing a repeating unit having another structure. Further, the repeating unit having a structure represented by the general formula (1) contained in the polymer may be a single type or two or more types. Examples of the repeating unit having no structure represented by the general formula (1) include those derived from monomers used in ordinary copolymerization. For example, repeating units derived from monomers having an ethylenically unsaturated bond such as ethylene and styrene can be cited.

[0054] In a certain embodiment, the compound represented by the general formula (1) is a luminescent material. In a certain embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence. In a certain embodiment of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the UV region, the blue, green, yellow, orange, or red region (for example, about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) of the visible spectrum, or the near-infrared region. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the red or orange region (e.g., from about 620 nm to about 780 nm, about 650 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the orange or yellow region (e.g., from about 570 nm to about 620 nm, about 590 nm, about 570 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the green region (e.g., from about 490 nm to about 575 nm, about 510 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the blue region (e.g., from about 400 nm to about 490 nm, about 475 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the ultraviolet spectral region (e.g., 280 - 400 nm). In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the infrared spectral region (e.g., 780 nm - 2 μm). In certain embodiments of the present disclosure, an organic semiconductor device can be fabricated using a compound represented by General Formula (1). The organic semiconductor device referred to herein may be an organic optoelectronic device in which light is involved, or may be an organic device in which light is not involved. The organic optoelectronic device may be an organic light-emitting device in which the device emits light, an organic light-receiving device in which the device receives light, or a device in which energy transfer by light occurs within the device. In certain embodiments of the present disclosure, an organic optoelectronic device such as an organic electroluminescence device or a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using the compound represented by General Formula (1). In certain embodiments of the present disclosure, a CMOS (complementary metal oxide semiconductor), etc. can be fabricated using the compound represented by General Formula (1).

[0055] The electronic properties of a library of small molecule chemical substances can be calculated using known ab initio quantum chemical calculations. For example, based on the basis, 6-31G*, and the time-dependent density functional theory using a group of functions known as the three-parameter Becke, Lee-Yang-Parr hybrid functional, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) is analyzed to screen for molecular fragments (portions) having a HOMO above a specific threshold and a LUMO below a specific threshold. Thereby, for example, when there is a HOMO energy (e.g., ionization potential) of -6.5 eV or higher, a donor moiety (“D”) can be selected. Also, for example, when there is a LUMO energy (e.g., electron affinity) of -0.5 eV or lower, an acceptor moiety (“A”) can be selected. The bridge moiety (“B”) is, for example, a strong conjugated system that can severely restrict the acceptor and donor moieties to a specific steric configuration, thereby preventing overlap between the π-conjugated systems of the donor and acceptor moieties. In certain embodiments, the compound library is selected 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 STValue 4. Quantum yield above a specific value 5. HOMO level 6. LUMO level In certain embodiments, the difference (ΔE ST ) between the lowest singlet excited state and the lowest triplet excited state at 77K 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 certain embodiments, the value of ΔE ST 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 General Formula (1) exhibits a quantum yield of more than 25%, such as 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.

[0056] [Synthesis method of the 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, a cyanobenzene having an alkyl group and a halogen atom can be reacted with a substituted or unsubstituted carbazole to synthesize a compound of General Formula (1) substituted with a substituted or unsubstituted carbazol-9-yl group. For details of the reaction conditions, reference can be made to the synthesis examples described below.

[0057] [Composition using the compound represented by General Formula (1)] In one embodiment, it is used in combination with a compound represented by the general formula (1), the compound is dispersed, covalently bonded to the compound, coated with the compound, supported by the compound, or associated with one or more materials (such as small molecules, polymers, metals, metal complexes, etc.) to form a solid film or layer. For example, a film can be formed by combining the compound represented by the general formula (1) with an electroactive material. In some cases, the compound represented by the general formula (1) may be combined with a hole-transporting polymer. In some cases, the compound represented by the general formula (1) may be combined with an electron-transporting polymer. In some cases, the compound represented by the general formula (1) may be combined with a hole-transporting polymer and an electron-transporting polymer. In some cases, the compound represented by the general formula (1) may be combined with a copolymer having both a hole-transporting part and an electron-transporting part. According to the above embodiments, electrons and / or holes formed in the solid film or layer can be made to interact with the compound represented by the general formula (1).

[0058] [Film Formation] In one embodiment, a film containing the compound represented by the general formula (1) can be formed by a wet process. In the wet process, a solution in which a composition containing the compound of the present invention is dissolved is applied to a surface, and a film is formed after removing the solvent. Examples of the wet process include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In one embodiment, a substituent (such as an alkyl group) that increases the solubility of the compound contained in the composition in the organic solvent can be introduced into the compound. In certain embodiments, a film containing the compound of the present invention can be formed by a dry process. In certain embodiments, a vacuum deposition method can be employed as the dry process, but is not limited thereto. When the vacuum deposition method is employed, the compounds constituting the film may be co-deposited from individual deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed. When using a single deposition source, a mixed powder obtained by mixing the compound powders may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating and melting each compound and then cooling may be used. In certain embodiments, by performing co-deposition under conditions where the deposition rates (weight loss rates) of the plurality of compounds contained in the single deposition source are the same or substantially the same, a film having a composition ratio corresponding to the composition ratio of the plurality of compounds contained in the deposition source can be formed. If a plurality of compounds are mixed at the same composition ratio as the composition ratio of the film to be formed to form a deposition source, a film having a desired composition ratio can be easily formed. In certain embodiments, the temperature at which each co-deposited compound has the same weight loss rate can be specified and adopted as the temperature during co-deposition.

[0059] [Examples of the use of the compound represented by the general formula (1)] The compound represented by the general formula (1) is useful as a material for an organic light-emitting element. It is particularly preferably used for an organic light-emitting diode or the like. Organic light-emitting diode: One aspect of the present invention relates to the use of the compound represented by the general formula (1) of the present invention as a light-emitting material for an organic light-emitting device. In certain embodiments, the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In certain embodiments, the compound represented by the general formula (1) includes delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In certain embodiments, the present invention provides a delayed phosphor having a structure represented by the general formula (1). In certain embodiments, the present invention relates to the use of the compound represented by the general formula (1) as a delayed phosphor. In certain embodiments, the compound represented by the general formula (1) can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting materials can be fluorescent materials, phosphorescent materials, or TADF. In certain embodiments, the compound represented by the general formula (1) can also be used as a hole transport material. In certain embodiments, the compound represented by the general formula (1) can be used as an electron transport material. In certain embodiments, the present invention relates to a method for generating delayed fluorescence from the compound represented by the general formula (1). In certain embodiments, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. In certain embodiments, the light-emitting layer contains the compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to the substrate. In certain embodiments, the substrate is a film-forming surface. In certain embodiments, the orientation of the compound represented by the general formula (1) with respect to the film-forming surface affects or determines the propagation direction of the light emitted by the compound that aligns it. In certain embodiments, by aligning the propagation direction of the light emitted by the compound represented by the general formula (1), the light extraction efficiency from the light-emitting layer is improved. One aspect of the present invention relates to an organic light-emitting device. In certain embodiments, the organic light-emitting device includes a light-emitting layer. In certain embodiments, the light-emitting layer includes a compound represented by the general formula (1) as a light-emitting material. In certain embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device). In certain embodiments, the organic light-emitting device is an organic electroluminescence device (organic EL device). In certain embodiments, the compound represented by the general formula (1) assists (as a so-called assist dopant) the light emission of other light-emitting materials contained in the light-emitting layer. In certain embodiments, the compound represented by the general formula (1) contained in the light-emitting layer is in its lowest excited singlet energy level and is included 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 other light-emitting materials contained in the light-emitting layer. In certain embodiments, the organic photoluminescence device includes at least one light-emitting layer. In certain embodiments, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In certain embodiments, the organic layer includes at least a light-emitting layer. In certain embodiments, the organic layer includes only the light-emitting layer. In certain embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer, and an exciton barrier layer. In certain 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. An example of the organic electroluminescence device is shown in FIG. 1.

[0060] Light-emitting layer: In certain embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and the cathode, respectively, recombine to form excitons. In certain embodiments, the layer emits light. In certain embodiments, only the luminescent material is used as the light-emitting layer. In certain embodiments, the light-emitting layer comprises a luminescent material and a host material. In certain embodiments, the luminescent material is one or more compounds represented by General Formula (1). In certain embodiments, singlet excitons and triplet excitons generated in the luminescent material are confined within the luminescent material in order to improve the light emission efficiency of the organic electroluminescence device and the organic photoluminescence device. In certain embodiments, a host material is used in addition to the luminescent material in the light-emitting layer. In certain embodiments, the host material is an organic compound. In certain embodiments, the organic compound has singlet excitation energy and triplet excitation energy, at least one of which is higher than those of the luminescent material of the present invention. In certain embodiments, singlet excitons and triplet excitons generated in the luminescent material of the present invention are confined within the molecules of the luminescent material of the present invention. In certain embodiments, singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In certain embodiments, despite still obtaining a high light emission efficiency, singlet excitons and triplet excitons are not sufficiently confined, that is, a host material capable of achieving a high light emission efficiency can be used in the present invention without particular limitation. In certain embodiments, light emission occurs in the luminescent material in the light-emitting layer of the device of the present invention. In certain embodiments, the emitted light includes both fluorescence and delayed fluorescence. In certain embodiments, the emitted light includes the emitted light from the host material. In certain embodiments, the emitted light consists of the emitted light from the host material. In certain embodiments, the emitted light includes the emitted light from the compound represented by General Formula (1) and the emitted light from the host material. In certain embodiments, a TADF molecule and a host material are used. In certain embodiments, TADF is an assist dopant, having a lower singlet excitation energy than the host material in the light-emitting layer and a higher singlet excitation energy than the luminescent material in the light-emitting layer.

[0061] When using the compound represented by the general formula (1) as an assist dopant, various compounds can be adopted as the luminescent material (preferably a fluorescent material). As such luminescent materials, anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives having metals (Al, Zn), etc. can be used. These exemplified skeletons may or may not have substituents. Also, these exemplified skeletons may be combined with each other. Hereinafter, luminescent materials that can be used in combination with the assist dopant having the structure represented by the general formula (1) will be exemplified.

[0062]

Chemical formula

Chemical formula

Chemical formula

[0063] Also, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can be particularly preferably adopted as the luminescent materials used together with the assist dopant having the structure represented by the general formula (1).

[0064] In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 0.1 wt% or more. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 1 wt% or more. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 50 wt% or less. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 20 wt% or less. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 10 wt% or less. In certain embodiments, the host material of the light-emitting layer is an organic compound having a hole transport function and an electron transport function. In certain embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of the emitted light from increasing. In certain embodiments, the host material of the light-emitting layer is an organic compound having a high glass transition temperature.

[0065] In some embodiments, the host material is selected from the group consisting of:

Chemical formula

Chemical formula

[0066] Hereinafter, each member of the organic electroluminescence element and each layer other than the light-emitting layer will be described.

[0067] Substrate: In some embodiments, the organic electroluminescence element of the present invention is held by a substrate, and the substrate is not particularly limited, and any material formed of, for example, glass, transparent plastic, quartz, and silicon, which is generally used in organic electroluminescence elements, may be used.

[0068] Anode: In some embodiments, the anode of the organic electroluminescence device is manufactured from 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 more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material such as IDIXO (In2O3-ZnO) that can form a transparent conductive film is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is produced by vapor deposition or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, when high precision of the pattern is not required (for example, about 100 μm or more), the pattern may be formed using a mask having a shape suitable for vapor deposition or sputtering on the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film forming method such as a printing method or a coating method is used. In some embodiments, when the 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 or less per unit area. 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.

[0069] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal having a low work function (4 eV or less, referred to as an electron injection metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron injection metal and a second metal, which is a stable metal having a work function higher than that of the electron injection metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection characteristics and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the cathode is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, in order to transmit the emitted light, either the anode or the cathode of the organic electroluminescence device is transparent or translucent. In some embodiments, the transparent or translucent electroluminescence device improves the light emission luminance. In some embodiments, the cathode is formed of the conductive transparent material described above with respect to the anode, thereby forming a transparent or translucent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or translucent.

[0070] 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 emission luminance. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the light-emitting layer or the hole transport layer, and between the cathode and the light-emitting layer or the electron transport layer. In some embodiments, an injection layer exists. In some embodiments, no injection layer exists. Examples of preferred compounds that can be used as the hole injection material are given below.

[0071]

Chemical formula

[0072] Next, examples of preferred compounds that can be used as the electron injection material are given.

Chemical formula

[0073] Barrier layer: The barrier layer is a layer that can prevent the charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, the electron barrier layer exists between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer and reaching the hole transport layer. In some embodiments, the hole barrier layer exists between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer and reaching the electron transport layer. In some embodiments, the barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. As used herein, the term "electron barrier layer" or "exciton barrier layer" includes a layer having both the functions of an electron barrier layer and an exciton barrier layer.

[0074] Hole barrier layer: The hole blocking layer functions as an electron transport layer. In some embodiments, during the transport of electrons, the hole blocking layer prevents holes from reaching the electron transport layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The material used for the hole blocking layer may be the same as the material described above for the electron transport layer. Examples of preferred compounds that can be used for the hole blocking layer are given below.

[0075]

Chemical formula

[0076] Electron blocking layer: The electron blocking layer transports holes. In some embodiments, during the transport of holes, 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 material used for the electron blocking layer may be the same as the material described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are given below.

[0077]

Chemical formula

[0078] Exciton blocking layer: The exciton barrier layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton barrier layer enables effective confinement of excitons in the light-emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton barrier layer is on either the anode side or the cathode side, and adjacent to the light-emitting layer on both sides thereof. In some embodiments, when the exciton barrier layer is present on the anode side, the layer is present between the hole transport layer and the light-emitting layer and may be adjacent to the light-emitting layer. In some embodiments, when the exciton barrier layer is present on the cathode side, the layer is present between the light-emitting layer and the cathode and may be adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron barrier layer or a similar layer is present between the anode and the exciton barrier layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron barrier layer, a hole barrier layer or a similar layer is present between the cathode and the exciton barrier layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton barrier layer includes singlet excitation energy and triplet excitation energy, at least one of which is higher than the singlet excitation energy and the triplet excitation energy of the light-emitting material, respectively.

[0079] Hole transport layer: The hole transport layer includes a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has a plurality of layers. In some embodiments, the hole transport material has one of the hole injection or transport properties and the electron barrier property. 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 porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as the hole transport material are given below.

[0080] [Chemical formula]

[0081] Electron transport layer: The electron transport layer contains 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 have the function of transporting the electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole barrier material. Examples of the electron transport layer that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide, fluorenylidene methane derivatives, anthraquinodimethane, 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 the electron transport material are given below.

[0082]

Chemical formula

[0083] Furthermore, preferred compound examples of materials that can be added to each organic layer are given. For example, it is conceivable to add it as a stabilizing material or the like.

[0084]

Chemical formula

[0085] Although preferred materials that can be used in the organic electroluminescence device have been specifically exemplified, the materials that can be used in the present invention should not be construed as being limited by the following exemplified compounds. Also, even the compounds exemplified as materials having specific functions can be diverted as materials having other functions.

[0086] Device: In some embodiments, the light-emitting layer is incorporated into the device. For example, the device includes, but is not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones and tablets. In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivatable devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for promoting charge transfer or energy transfer within the device and / or as hole transport materials. Examples of 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 detection devices, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0087] Valve or lamp: In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (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 combination of two colors, four colors, or more colors. In some embodiments, the device is a circuit board having a first surface with an attachment surface and a second surface opposite thereto and defining at least one opening, At least one OLED on the mounting surface, wherein the at least one OLED has a light-emitting configuration including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. A housing for a circuit board, At least one connector disposed at an end of the housing, wherein the housing and the connector define a package suitable for attachment to a lighting fixture. The OLED light includes at least one connector. In some embodiments, the OLED light has a plurality of OLEDs mounted on a circuit board such that light is emitted in a plurality of directions. In some embodiments, some 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.

[0088] Display or screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or a display. In some embodiments, the compounds according to 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 in two-sided etching that provides pixels with a unique aspect ratio. The screen (also referred to as a mask) is used in the manufacturing process of an OLED display. The design of the corresponding artwork pattern enables the arrangement of very sharp and narrow tethers between pixels in the vertical direction and a large wide-angle aperture in the horizontal direction. This enables a fine pattern configuration of pixels required for a high-resolution display while optimizing chemical vapor deposition onto the TFT backplane. Internal patterning of the pixels enables the formation of three-dimensional pixel apertures with various aspect ratios in the horizontal and vertical directions. Further, the use of imaged "stripes" or halftone circles in the pixel region protects the etching in specific regions until these specific patterns are undercut and removed from the substrate. At that time, all pixel regions are processed at a similar etching rate, but the depth varies with the halftone pattern. By changing the size and spacing of the halftone pattern, etching with various different protection rates within the pixel becomes possible, enabling localized deep etching necessary to form a sharp vertical bevel. A preferred material for the evaporation mask is Invar. Invar is a metal alloy cold-rolled in a long thin sheet form at a steel mill. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming an opening region in the evaporation mask is a method 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 processed using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is processed using wet chemical etching. In further embodiments, the screen or display pattern is processed using plasma etching.

[0089] Method for manufacturing a device: An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panel units. Usually, each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light emitting layer, a counter electrode, and a encapsulation layer over time, and then cutting from the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panel units. Usually, each cell panel on the mother panel forms a thin-film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applies a planarization film to the TFT, and sequentially forms a pixel electrode, a light-emitting layer, a counter electrode, and a encapsulation layer over time, and is formed by cutting from the mother panel.

[0090] In another aspect of the present invention, there is provided a method for manufacturing an organic light-emitting diode (OLED) display, the method comprising: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units in cell panel units on the barrier layer; forming an encapsulation layer on each of the display units of the cell panel; applying an organic film to an interface portion between the cell panels. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and an end portion of the barrier layer is covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists the mother panel to be cut softly in cell panel units. In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may have 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 portion is formed of the same material as the material of the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to either the display unit or the encapsulation layer.

[0091] Each of the organic film and the planarization film may include either polyimide or 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 further includes 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 one surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface portion. 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 for coating the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylic, similar to the organic film formed at the end of the barrier layer. 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 at the end of the barrier layer, such that a part of the organic film is in direct contact with the base substrate, and the remaining part of the organic film surrounds the end of the barrier layer and contacts the barrier layer.

[0092] In some embodiments, the light-emitting layer has 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 the 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, whereby the organic light-emitting layer emits light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display unit and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which an organic film and an inorganic film are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is disposed at intervals from each of the plurality of display units. In some embodiments, the organic film is formed in such a manner that some of the organic film is in direct contact with the base substrate, and the remaining portion of the organic film surrounds the end portion of the barrier layer while being in contact with the barrier layer.

[0093] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide. In some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated. In some embodiments, the barrier layer is formed on the surface of the base substrate on the opposite side of 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, whereby grooves are formed in the interface portion between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0094] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, where grooves are formed in the barrier layer, at least a part of the organic film is formed by the grooves, and the grooves do not penetrate the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and the passivation layer which is an inorganic film and the planarization film which is an organic film are disposed on the TFT layer to cover the TFT layer. For example, when a planarization film made of polyimide or acrylic is formed, the grooves in the interface portion are covered with an organic film made of polyimide or acrylic, for example. This prevents cracking by allowing the generated impact to be absorbed by the organic film when each cell panel is cut along the groove at the interface portion. That is, when all the barrier layers are completely exposed without the organic film, when each cell panel is cut along the groove at the interface portion, the generated impact is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the grooves in the interface portion between the barrier layers are covered with an organic film to absorb the impact that could be transmitted to the barrier layer without the organic film, so that each cell panel may be cut softly to prevent cracking in the barrier layer. In one embodiment, the organic film covering the grooves in the interface portion and the planarization film are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, there is a risk that external moisture may enter the display unit through the remaining portions of the planarization film and 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.

[0095] In some embodiments, the display unit is formed by forming a light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit. Thereby, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is radiated to the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in the coefficient of thermal expansion between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into cell panel units. In some embodiments, the mother panel is cut along the interface portion between the cell panels using a cutter. In some embodiments, since the groove of the interface portion along which the mother panel is cut is covered with an organic film, the organic film absorbs an impact during cutting. In some embodiments, it is possible to prevent cracks from occurring in the barrier layer during cutting. In some embodiments, the method reduces the defect rate of the product and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to an end portion of the barrier layer.

Example

[0096] The features of the present invention will be further specifically described below with reference to synthesis examples and examples. The materials, treatment details, treatment procedures, etc. shown below can be appropriately changed as long as they do not depart from the gist 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 evaluation of the light emission characteristics was carried out using a source meter (manufactured by Keithley Instruments, Inc.: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies, Inc.: E5273A), an optical power meter measuring device (manufactured by Newport Corporation: 1930C), an optical spectrometer (manufactured by Ocean Optics, Inc.: USB2000), a spectro-radiometer (manufactured by Topcon Corporation: SR-3), and a streak camera (model C4334 manufactured by Hamamatsu Photonics K.K.). The measurement of the energies of HOMO and LUMO was carried out by air photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-3, etc.). In the following synthesis example, the compound contained in the general formula (1) was synthesized.

[0097] (Synthesis Example) Synthesis of Compound 236780 and Compound 236925 [Chemical Formula]

[0098] Intermediate A Under a nitrogen stream, 20 mL of a solution of 4.92 g (30.0 mmol) of 1,2,4,5-tetrafluoro-3-methylbenzene in tetrahydrofuran was added dropwise to 20 mL of a hexane-tetrahydrofuran solution of lithium diisopropylamide (LDA) (1.09 mol / L) at -78°C over 30 minutes, and the mixture was stirred for 1 hour. A solution of 11.4 g (45.0 mmol) of iodine in 17.5 mL of tetrahydrofuran was added to the reaction solution, and the mixture was stirred at room temperature for 12 hours. The reaction solution was washed with a saturated aqueous sodium pyrosulfite solution, the aqueous layer was extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane) to obtain 5.41 g (18.7 mmol, yield 62%) of Intermediate A as a colorless transparent liquid. 1H-NMR (400 MHz, CDCl3): δ 2.27 (t, J = 2.3 Hz, 3H).

[0099] Intermediate B Under a nitrogen stream, 2.49 g (27.8 mmol) of copper cyanide was added to a solution of intermediate A (5.41 g, 18.7 mmol) in tetrahydrofuran (12 mL), and the mixture was stirred at 150 °C for 2 hours. Chloroform was added to the reaction solution, and the organic layer filtered through celite was washed with aqueous ammonia and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (hexane) to obtain 2.49 g (13.2 mmol, yield 71%) of intermediate B as a pale yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 2.39 (t, J = 2.3 Hz, 3H).

[0100] Intermediate C Under a nitrogen stream, tetrahydrofuran (10 mL) was added to 0.84 g (5.00 mmol) of 9H-carbazole and 0.12 g (5.13 mmol) of sodium hydride, and the mixture was stirred at room temperature for 30 minutes. The resulting mixed solution was added to a solution of intermediate B (0.47 g, 2.50 mmol) in tetrahydrofuran (25 mL) at -50 °C, and the mixture was stirred for 24 hours. Water was added to the reaction solution, and the precipitate was filtered off. The solid on the filter was washed with methanol and dried under vacuum. The crude product was purified by silica gel column chromatography (hexane:dichloromethane = 2:1) to obtain 0.41 g (0.85 mmol, yield 34%) of intermediate C as a white solid. 1 H-NMR (400 MHz, CDCl3, δ): 8.16 (d, J = 8.2 Hz, 4H), 7.51 (t, J = 8.2 Hz, 4H), 7.37 (t, J = 8.2 Hz, 4H), 7.22 (d, J = 8.2 Hz, 4H), 2.51 (s, 3H). ASAP MS spectrum analysis: C 32 H 19 F2N3 Theoretical value 483.15 Observed value 484.13

[0101] Compound 236780 Under a nitrogen stream, 0.75 g (2.25 mmol) of 2-phenyl-5H-benzo[f] [3,2-c]carbazole and 0.37 g (2.70 mmol) of potassium carbonate were added to an N,N-dimethylformamide (9.0 mL) solution, and intermediate C (0.44 g, 0.90 mmol) was added thereto. The mixture was stirred at 110 °C for 6 hours. The reaction mixture was returned to room temperature, water was added, and the precipitate was filtered off. The residue on the filter was washed with methanol and dried under vacuum. The crude product was purified by silica gel column chromatography (hexane:toluene:chloroform = 3.5:6.0:0.5) to obtain 0.76 g (0.68 mmol, 76% yield) of compound 236780 as a pale yellow solid. 1 1H-NMR (400 MHz, CDCl3): 8.42-8.40 (m, 2H), 7.99-7.96 (m, 2H), 7.87 (d, J = 8.2 Hz, 1H), 7.79 (d, J = 8.2 Hz, 1H), 7.76-7.67 (m, 10H), 7.54-7.49 (m, 6H), 7.47-7.35 (m, 10H), 7.32-7.18 (m, 9H), 7.17-7.12 (m, 3H), 7.09-7.01 (m, 3H), 1.96 (s, 3H). ASAP MS spectrum analysis: C 80 H 47 N5O2: Theoretical value 1109.37, Observed value 1110.69

[0102] Compound 236925 Under a nitrogen stream, 0.68 g (2.15 mmol) of 3,6-diphenylcarbazole and 0.40 g (2.9 mmol) of potassium carbonate were added to a dimethylformamide solution (19.5 mL), and intermediate C (0.47 g, 0.97 mmol) was added thereto. The mixture was stirred at 110 °C for 13 hours. The mixture was returned to room temperature, quenched by adding methanol, and the precipitated solid was filtered, washed with water and methanol. The obtained solid was purified by silica gel column chromatography to obtain 1.05 g (0.97 mmol, 99.0% yield) of compound 236925. 1 1H-NMR (400 MHz, CDCl3, δ) 8.02 (s, 4H), 7.75 (d, J = 7.6 Hz, 4H), 7.62 (d, J = 6.8 Hz, 8H), 7.48 - 7.41 (m, 12H), 7.38 - 7.33 (m, 8H), 7.51 - 7.11 (m, 8H), 7.247 - 7.171 (m, 8H), 7.12 (t, J = 7.2, 6.8 Hz, 4H), 2.06 (s, 3H) ASAP mass spectrum analysis: theoretical value 1081.41, observed value 1082.82

[0103] (Example 1) Preparation and evaluation of thin films On a quartz substrate, compound 236780 and H1 were vapor-deposited from different vapor-deposition sources under the condition of a vacuum degree of less than 1×10 -3 Pa by vacuum evaporation, and a thin film with a concentration of compound 236780 of 20 wt% was formed with a thickness of 100 nm. Using compound 236925, comparative compound 1, and comparative compound 2 instead of compound 236780 respectively, thin films were prepared by the same procedure. The maximum emission wavelength (λmax) when each formed thin film was irradiated with 300 nm excitation light was measured, and the energy of HOMO and the energy of LUMO were also measured. The measurement results were summarized in Table 4. Also, the energy difference ΔE ST between the lowest excited singlet state and the lowest excited triplet state at 77K was measured. For compound 1, it was 0.12 eV, and for compound 2, it was 0.18 eV. [Chemical formula]

[0104] (Example 2) Preparation and evaluation of organic electroluminescence devices On a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, each thin film was vacuum-evaporated under a vacuum degree of 5.0×10 -5They were laminated at Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 35 nm, and PTCz was further formed thereon to a thickness of 10 nm. Next, H1 and Compound 236780 were co-evaporated from different evaporation sources to form a layer with a thickness of 40 nm as the light-emitting layer. The concentration of Compound 236780 in the light-emitting layer was 30% by mass. Next, ET1 was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a layer with a thickness of 20 nm. The concentrations of Liq and SF3-TRZ in this layer were 30% by mass and 70% by mass, respectively. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form the cathode, resulting in an organic electroluminescence device. Using Compound 236925, Comparative Compound 1, and Comparative Compound 2, respectively, instead of Compound 236780, each organic electroluminescence device was fabricated by the same procedure. When measuring the maximum external quantum efficiency (EQE) of each organic electroluminescence device using Compound 236780 and Compound 236925, high values of 11 - 15% were shown. Also, when measuring the chromaticity, as shown in Table 4, each organic electroluminescence device using Compound 236780 and Compound 236925 had a desirable deep blue emission color compared to the organic electroluminescence devices using Comparative Compound 1 or Comparative Compound 2. Furthermore, when measuring the lifetime τ2 of the delayed fluorescence, each organic electroluminescence device using Compound 236780 and Compound 236925 was 2.2 μs and 3.8 μs, respectively, which was shorter than that of the organic electroluminescence device using Comparative Compound 1 (28 μs).

[0105]

Table 4

[0106] The compound represented by the general formula (1) has ΔE STIt was an excellent luminescent material with a small size, a short delayed fluorescence lifetime, and a preferable deep blue color tone. Also, the organic electroluminescence device using the compound represented by the general formula (1) had a high luminous efficiency and was excellent as a device. In particular, by introducing an alkyl group into cyanobenzene having a donor group, it was possible to shorten the delayed fluorescence lifetime while suppressing the elongation of the emission wavelength and maintaining good color purity. [Chemical formula]

Explanation of symbols

[0107] 1 Substrate 2 Anode 3 Hole injection layer 4 Hole transport layer 5 Light-emitting layer 6 Electron transport layer 7 Cathode

Claims

1. A compound represented by the following general formula (1). 【Chemical 1】 In general formula (1), R ３ is an alkyl group, and R １ , R ２ , R ４ and R5 are each independently a substituted or unsubstituted carbazol-9-yl group which may have a condensed ring, and the carbazol-9-yl groups of R2 and R4 are each independently substituted with a substituted or unsubstituted aryl group.]

2. The compound according to Claim 1, wherein at least one of R1, R2, R4, and R5 is a substituted or unsubstituted carbazol-9-yl group having a condensed ring.

3. The compound according to Claim 1, wherein at least one of R1, R2, R4, and R5 is a substituted carbazol-9-yl group having a condensed ring.

4. The compound according to Claim 1, wherein at least one of R1, R2, R4, and R5 is a carbazol-9-yl group having a condensed ring and is substituted with a substituted or unsubstituted heteroaryl group.

5. The compound according to Claim 1, wherein at least one of R1, R2, R4, and R5 is a carbazol-9-yl group having a condensed ring and is substituted with a substituted or unsubstituted aryl group.

6. The compound according to any one of Claims 1 to 5, wherein at least one of R1, R2, R4, and R5 is a substituted or unsubstituted carbazol-9-yl group having a condensed ring with one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms.

7. The compound according to any one of Claims 1 to 5, wherein at least one of R1, R2, R4, and R5 is a substituted or unsubstituted carbazol-9-yl group having a condensed ring with one or more atoms selected from the group consisting of an oxygen atom and a sulfur atom as ring skeleton constituent atoms.

8. The compound according to any one of Claims 1 to 7, wherein there are two or more kinds of substituted or unsubstituted carbazol-9-yl groups in which the ring may be condensed, represented by R1, R2, R4, and R5.

9.

10. One of the two or more kinds is a substituted or unsubstituted carbazol-9-yl group having a condensed ring with one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms, and the other kind is a substituted or unsubstituted carbazol-9-yl group having no condensed ring. The compound according to Claim 8.

10. Among the above two or more kinds, one kind is a substituted or unsubstituted carbazol-9-yl group, and the other kind is a carbazol-9-yl group substituted with a substituent different from the substituted or unsubstituted carbazol-9-yl group, the compound according to claim 8 or 9.

11. The compound according to any one of claims 1 to 10, which has a line-symmetric structure.

12. A light-emitting material comprising the compound according to any one of claims 1 to 11.

13. A delayed phosphor comprising the compound according to any one of claims 1 to 11.

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

15. An organic semiconductor device comprising the compound according to any one of claims 1 to 11.

16. An organic light-emitting device comprising the compound according to any one of claims 1 to 11.

17. The organic light-emitting device according to claim 16, wherein the device has a layer containing the compound, and the layer also contains a host material.

18. The layer containing the compound further contains a delayed fluorescence material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound, the organic light-emitting device according to claim 17.

19. The organic light-emitting device according to claim 17, wherein the device has a layer containing the compound, and the layer also contains a light-emitting material having a structure different from that of the compound.

20. Among the materials contained in the device, the amount of light emission from the compound is the largest, the organic light-emitting device according to any one of claims 17 to 19.

21. The amount of light emission from the light-emitting material is larger than the amount of light emission from the compound, the organic light-emitting device according to claim 19.

22. The organic light-emitting device according to any one of claims 16 to 21, which is an organic electroluminescence device.

23. The organic light-emitting device according to any one of claims 16 to 21, which emits delayed fluorescence.

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