Organic light emitting element

Abstract

To provide an organic light emitting element with excellent light emission characteristics.SOLUTION: This organic light emitting element comprises a compound of the general formula below and a boron compound, where R1 to R5 each represent H, D, an alkyl group, an aryl group, a non-fused carbazol-9-yl group, a triazinyl group substituted with Ar3 and Ar4, or the like; R2 or R3 is the triazinyl group or the like; and one or more of R1 to R5 are each the non-fused carbazol-9-yl group; one to three of X1 to X3 each represent N, and the remainder each represent C(R6); and Ar1 to Ar4 each represent an aryl group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an organic light-emitting device using a compound having a skeleton in which a plurality of nitrogen-atom-containing heteroaromatic rings are bonded to a benzene ring. [Background technology]

[0002] Research into the development of luminescent materials such as organic electroluminescent elements (organic EL elements) is being actively conducted. Fluorescent materials, phosphorescent materials, and fluorescent materials have long been known as luminescent materials, but fluorescent materials have the problem of low luminous efficiency, and phosphorescent materials contain rare metals, making them expensive and difficult to emit deep blue light. In recent years, delayed fluorescent materials have been developed as luminescent materials that address these issues.

[0003] A delayed fluorescent material is a material that emits fluorescence when it returns from an excited singlet state to a ground state after reverse intersystem crossing from an excited triplet state to an excited singlet state in an excited state. Fluorescence by such a route is observed later than fluorescence from an excited singlet state directly generated from a ground state (normal fluorescence), and is therefore called delayed fluorescence. Here, for example, when a light-emitting compound is excited by carrier injection, the probability of occurrence of an excited singlet state and an excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency only by fluorescence from an excited singlet state directly generated. On the other hand, in a delayed fluorescent material, not only an excited singlet state but also an excited triplet state can be used for fluorescence emission by a route via the above-mentioned reverse intersystem crossing, and therefore a higher luminous efficiency can be obtained than that of a normal fluorescent material.

[0004] Since this principle was clarified, various delayed fluorescent materials have been discovered through various researches. Many of these materials include compounds in which a donor group and an acceptor group are substituted on a benzene ring. For example, a compound has been proposed that has a skeleton in which a carbazol-9-yl group, which is a donor group, and a cyano group and a substituted triazinyl group, which are acceptor groups, are substituted on a benzene ring (see Patent Document 1). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] WO2022 / 270600A1 Summary of the Invention [Problem to be solved by the invention]

[0006] On the other hand, even if a material emits delayed fluorescence, its characteristics are very good and there are no practical problems, so far there has been no material provided. In addition, when used in organic light-emitting devices such as organic electroluminescence devices, it is necessary to devise a way of using it in order to provide an element with excellent performance. For this reason, the improvement of delayed fluorescent materials and the improvement of the performance of organic light-emitting devices have been issues for many years, but solutions to these issues are still in the trial and error stage. Under these circumstances, the present inventors have carried out extensive research with the aim of providing an organic light-emitting device having excellent light-emitting properties. [Means for solving the problem]

[0007] As a result of intensive research to achieve the above object, the present inventors have found that the light-emitting properties of an organic light-emitting device can be improved by using a compound having a structure that satisfies a specific condition in combination with a compound that satisfies another condition. The present invention has been proposed based on this finding, and specifically has the following configuration. [1] An organic light-emitting device comprising a compound represented by the following general formula (1) and a light-emitting material having a boron atom (excluding boron complexes): [ka] [In the general formula (1), R 1 ~R 5each independently represents a non-condensed carbazol-9-yl group which may be substituted with one or a combination of two or more selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a deuterium atom, an alkyl group, and an aryl group, or a group represented by the following general formula (2). 2 or R 3 is a group represented by the following general formula (2), R 1 ~R 5 At least one of X is the non-fused carbazol-9-yl group. 1 ~X 3 At least one of them is N and the rest are C(R 6 ) stands for R 6 represents a hydrogen atom, a deuterium atom or a substituent. 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group. [ka] In the general formula (2), X 4 ~X 6 At least one of them is N and the rest are C(R 7 ) stands for R 7 represents a hydrogen atom, a deuterium atom or a substituent. 3 and Ar 4 Each independently represents a substituted or unsubstituted aryl group. 1 represents a single bond or a divalent linking group. * represents the bonding position.] [2] R 2 is a group represented by general formula (2). [3] R 3 is a group represented by general formula (2). [4] R 1 ~R 5 The organic light-emitting element according to any one of [1] to [3], wherein two or more of the groups are the non-fused carbazol-9-yl group. [5] R 1 ~R 5The organic light-emitting element according to any one of [1] to [3], wherein three of the groups are the non-fused carbazol-9-yl group. [6] X 1 ~X 3 The organic light-emitting device according to any one of [1] to [5], wherein two or more of the above are N. [7] X 4 ~X 6 The organic light-emitting device according to any one of [1] to [6], wherein two or more of the above are N. [8] L 1 The organic light-emitting device according to any one of [1] to [7], wherein [9] R 1 The organic light-emitting device according to any one of [1] to [8], wherein

[10] The organic light-emitting device according to any one of [1] to [9], which has at least one deuterium atom.

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

[10] , wherein the light-emitting material having a boron atom is a compound represented by the following general formula (3): [ka] [In the general formula (3), X 1 and X 2 is a nitrogen atom on one side and a boron atom on the other side. 1 ~R 26 , A 1 , A 2 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 may be bonded to each other to form a cyclic structure. 1 is a nitrogen atom, R 17 and R 18 are bonded to each other to form a single bond to form a pyrrole ring, and X 2 is a nitrogen atom, R 21 and R 22 are bonded to each other as a single bond to form a pyrrole ring.

[12] R in general formula (3) 3 and R 6 and each of the groups is a substituent.

[13] R in general formula (3) 8 , R 10 and R 12 and each of the groups represented by the formula (11) and (12) is a substituent.

[14] X in formula (3) 1 is a nitrogen atom, and X 2 The organic light-emitting element according to any one of

[11] to

[13] , wherein is a boron atom.

[15] R in general formula (3) 1 and R 2 , R 2 and R 3 , R 3and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 The organic light-emitting device according to any one of

[11] to

[14] , wherein none of the pairs are bonded to each other to form a cyclic structure.

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

[10] , wherein the light-emitting material having a boron atom is a compound having the following skeleton: [ka] Effect of the Invention

[0008] The organic light-emitting device of the present invention has excellent light-emitting properties. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "~" means a range including the numerical values ​​before and after "~" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( 2 In the chemical structural formulas of this specification, hydrogen atoms are represented as H or are omitted. For example, when the atom bonded to the ring-structuring carbon atom of a benzene ring is omitted, H is assumed to be bonded to the ring-structuring carbon atom at the omitted position. In this specification, the term "substituent" means an atom or atomic group other than hydrogen atoms and deuterium atoms. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0010] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be described. [ka]

[0011] In the general formula (1), R 1 ~R 5 each independently represents a non-condensed carbazol-9-yl group which may be substituted with one or more groups selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a deuterium atom, an alkyl group, and an aryl group, or a group represented by the general formula (2) described below. 2 or R 3 is a group represented by general formula (2), R 1 ~R 5 At least one of X is the non-fused carbazol-9-yl group. 1 ~X 3At least one of them is N and the rest are C(R 6 ) stands for R 6 represents a hydrogen atom, a deuterium atom or a substituent. 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group.

[0012] R 1 ~R 5 The alkyl group may be linear, branched, or cyclic. Two or more of the linear, cyclic, and branched portions may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The alkyl group as a substituent may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. In one embodiment of the present invention, the alkyl group has one or more substituents selected from the group consisting of an aryl group and a deuterium atom. In a preferred embodiment of the present invention, the alkyl group is unsubstituted and may be selected from the group consisting of, for example, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.

[0013] R 1 ~R 5 , Ar 1 and Ar 2The aryl group may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, and is preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E. In one embodiment of the present invention, the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is substituted with at least one deuterium atom. In one aspect of the invention, the aryl group is unsubstituted. In the following, R 1 ~R 5 , Ar 1 and Ar 2 Specific examples of substituted or unsubstituted aryl groups that can be used are given below. However, the aryl groups that can be used in the present invention should not be construed as being limited to the following specific examples. In the following specific examples, * indicates a bonding position. Also, methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups. [ka] JPEG2024177837000007.jpg206167JPEG2024177837000008.jpg148164

[0014] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar25 are substituted with deuterium atoms are exemplified here as Ar45 to Ar69, in that order. In one aspect of the invention, R 1 ~R 5The aryl group that can be taken by R is selected from the group consisting of Ar1 to Ar69. 1 ~R 5 The aryl group of R can be Ar or Ar. 1 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, and Ar46 to Ar55. 1 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, and Ar56 to Ar63. 1 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar21 to Ar25 and Ar65 to Ar69. 1 ~R 5 The aryl group which can be taken is selected from the group consisting of Ar1, Ar12 to Ar14, Ar23, Ar36 to Ar38, Ar45, Ar56 to Ar58, and Ar67. In one aspect of the present invention, Ar 1 or Ar 2 The aryl group that can be taken by Ar is selected from the group consisting of Ar1 to Ar69. 1 or Ar 2 The aryl group of Ar can be Ar or Ar. 1 or Ar 2 The aryl group that can be taken by Ar is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, and Ar46 to Ar55. 1 or Ar 2 The aryl group that R can take is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, and Ar56 to Ar63. 1 ~R 5 The aryl group which can be taken is selected from the group consisting of Ar1, Ar12 to Ar14, Ar36 to Ar38, Ar45, and Ar56 to Ar58.

[0015] R in general formula (1) 1 ~R 5may be a non-fused carbazol-9-yl group optionally substituted with a group consisting of a deuterium atom, an alkyl group, and an aryl group. The non-fused carbazol-9-yl group here means a group in which no other ring is fused to the carbazole of a three-ring structure. 1 ~R 5 The non-fused carbazol-9-yl group may be unsubstituted or substituted with a group consisting of one or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group. When substituted, all of the 10 hydrogen atoms present in the non-fused carbazol-9-yl group may be substituted, or only a portion of them may be substituted. Examples of the embodiment in which only a portion of the 10 hydrogen atoms is substituted include an embodiment in which 1 to 5 are substituted, an embodiment in which 3 are substituted, an embodiment in which 2 are substituted, and an embodiment in which 1 is substituted. Examples of the embodiment in which only the 3-position is substituted, an embodiment in which the 3- and 6-positions are substituted, an embodiment in which the 1- and 8-positions are substituted, and an embodiment in which the 2- and 7-positions are substituted. The non-fused carbazol-9-yl group may be substituted only with a deuterium atom, may be substituted only with an unsubstituted alkyl group, may be substituted only with a partially or fully deuterated alkyl group, may be substituted only with an unsubstituted aryl group, or may be substituted only with a partially or fully deuterated aryl group. In addition, the non-fused carbazol-9-yl group may be substituted with an alkylaryl group which may be partially or fully deuterated, or with an arylalkyl group which may be partially or fully deuterated. 1 ~R 5The non-fused carbazol-9-yl group which can be taken is a carbazol-9-yl group in which at least one hydrogen atom is deuterated, more preferably a carbazol-9-yl group in which all hydrogen atoms are deuterated. In one embodiment of the present invention, the carbazol-9-yl group is an aryl group which may be substituted with one or two atoms selected from the group consisting of a deuterium atom and an alkyl group at at least one of the 3-position and the 6-position. In one embodiment of the present invention, the carbazol-9-yl group is an alkyl group which may be substituted with a deuterium atom at at least one of the 3-position and the 6-position.

[0016] In the following, R in general formula (1) 1 ~R 5 Specific examples of non-fused carbazol-9-yl groups that can be used are shown below. However, the non-fused carbazol-9-yl groups that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, Ph represents a phenyl group (C6H5), and * represents a bonding position. Since methyl groups are not shown, for example, D2 has one methyl group. However, a deuterated methyl group is represented as CD3. Also, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom. [ka] JPEG2024177837000010.jpg38170

[0017] D26 to D50 are disclosed as compounds obtained by substituting all hydrogen atoms present in the above D1 to D25 with deuterium atoms.

[0018] In one aspect of the invention, R 1 ~R 5 The non-fused carbazol-9-yl group that R can take is selected from the group consisting of D1 to D50. 1 ~R 5 The non-fused carbazol-9-yl group that R can take is selected from the group consisting of D14 to D50. 1 ~R 5The non-fused carbazol-9-yl group that R can take is selected from the group consisting of D1 to D7, D14 to D19, D26 to 32, and D39 to D44. 1 ~R 5 The non-fused carbazol-9-yl group which can be taken is selected from the group consisting of D8 to D13, D20 to D25, D33 to D38, and D45 to D50.

[0019] R in general formula (1) 1 ~R 5 At least one of R is a non-fused carbazol-9-yl group which may be substituted with one or a combination of two or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group. 1 ~R 5 It is preferable that 2 to 4 of R are the non-fused carbazol-9-yl group. 1 ~R 5 It is more preferable that two or three of R are the non-fused carbazol-9-yl group. 1 is not the non-fused carbazol-9-yl group. 2 ~R 5 In one embodiment of the present invention, at least two or three of R 2 or R 3 is the non-fused carbazol-9-yl group. In one embodiment of the present invention, at least R 4 is the non-fused carbazol-9-yl group. In one embodiment of the present invention, at least R 5 is the non-fused carbazol-9-yl group. 5 In one embodiment of the invention, R 3 and R 5 In one embodiment of the invention, R 2 and R 5 In one embodiment of the invention, R 2 and R 4In one embodiment of the invention, R 3 and R 4 and R 5 In one embodiment of the invention, R 2 and R 4 and R 5 Only the non-fused carbazol-9-yl group is R 1 ~R 5 When two or more of the above are the non-fused carbazol-9-yl groups, they may be the same or different. R 1 ~R 5 The number of hydrogen atoms or deuterium atoms among R is 0 to 2, preferably 0 or 1, for example 1, for example 0. For example, R 1 is a hydrogen atom or a deuterium atom. 1 ~R 5 R has better luminescence properties than compounds in which the number of hydrogen or deuterium atoms is three. 1 ~R 5 The number of substituted or unsubstituted aryl groups among R is 0 or 1, and preferably 1. 1 ~R 5 Among these, the number of those which are substituted or unsubstituted alkyl groups is 0 to 3, preferably 0 to 2, and may be 1 or 0. In one aspect of the invention, R 1 ~R 5 are each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, the non-fused carbazol-9-yl group, and a group represented by general formula (2). 1 ~R 5 are each independently selected from a hydrogen atom, a deuterium atom, the non-fused carbazol-9-yl group, and a group represented by general formula (2). 1 ~R 5 are each independently selected from a hydrogen atom, a deuterium atom, a carbazol-9-yl group which may be substituted with a deuterium atom, and a group represented by general formula (2).

[0020] In the general formula (1), X 1 ~X 3 One to three of them are N, and the rest are C(R 6 ) stands for R 6 represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected from the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E. In a more preferred embodiment of the present invention, X 1 ~X 3 is N. In a more preferred embodiment of the present invention, X 1 and X 2 is N and X 3 C(R 6 In a preferred embodiment of the present invention, X 1 and X 3 is N and X 2 C(R 6 In one aspect of the present invention, X 1 is N and X 2 and X 3 C(R 6 In one aspect of the present invention, X 3 is N and X 1 and X 2 C(R 6 In one aspect of the present invention, R 6 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 6 is an alkyl group optionally substituted with a deuterium atom. In one embodiment of the present invention, R 6 is an aryl group which may be substituted with a deuterium atom, an alkyl group, or an aryl group.

[0021] In one aspect of the invention, X 1 ~X 3 is N and Ar 1 and Ar 2 In one aspect of the present invention, X 1 ~X 3 is N and Ar 1 and Ar 2are each independently an at least partially deuterated aryl group. In one aspect of the invention, X 1 and X 2 is N and X 3 C(R 6 ) and R 6 is a hydrogen atom or a deuterium atom, and Ar 1 and Ar 2 In one aspect of the present invention, X 1 and X 2 is N and X 3 C(R 6 ) and R 6 is a hydrogen atom or a deuterium atom, and Ar 1 and Ar 2 are each independently an at least partially deuterated aryl group. In one aspect of the invention, X 1 and X 3 is N and X 2 C(R 6 ) and R 6 is a hydrogen atom or a deuterium atom, and Ar 1 and Ar 2 In one aspect of the present invention, X 1 and X 3 is N and X 2 C(R 6 ) and R 6 is a hydrogen atom or a deuterium atom, and Ar 1 and Ar 2 are each independently an at least partially deuterated aryl group.

[0022] In the general formula (1), R 2 or R 3 is a group represented by the following general formula (2). 1 , R 4 , R 5 can also be a group represented by the following general formula (2). [ka]

[0023] In the general formula (2), X4 ~X 6 One to three of them are N, and the rest are C(R 7 ) stands for R 7 represents a hydrogen atom, a deuterium atom or a substituent. 3 and Ar 4 Each independently represents a substituted or unsubstituted aryl group. 1 represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. * represents the bonding position.

[0024] L in general formula (2) 1 represents a single bond or a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group. In a preferred embodiment of the present invention, L 1 is a single bond. In one embodiment of the present invention, L 1 is a substituted or unsubstituted arylene group. In one embodiment of the present invention, L 1 is a substituted or unsubstituted heteroarylene group. The aryl moiety constituting the arylene group is as defined above for R 1 ~R 5 Refer to the description and preferred range of the aryl group in the description section of "1. Heteroarylene group" can be exemplified by a linking group in which at least one of the ring skeleton carbon atoms constituting an arylene group is substituted with a nitrogen atom. In the following, L 1 However, the following are specific examples of L that can be used in the present invention. 1 is not to be construed as being limited by these specific examples. In the following specific examples, the methyl group is omitted. Therefore, for example, L3 to L5 are substituted with a methyl group. * indicates a bond position. L1 is a single bond.

[0025] [ka]

[0026] All hydrogen atoms in L2 to L13 are replaced with deuterium atoms, and L14 to L25 are disclosed as such. 1 is selected from the group consisting of L1 to L25. In one embodiment of the present invention, L 1 is selected from the group consisting of L1 to L7 and L14 to L19. 1 is selected from the group consisting of L1, L8 to L13, and L20 to L25. 1 is selected from the group consisting of L2 to L25.

[0027] X in general formula (2) 4 ~X 6 One to three of them are N, and the rest are C(R 7 ) stands for R 7 represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected from the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E. In a preferred embodiment of the present invention, X 4 ~X 6 is N. In a preferred embodiment of the present invention, X 4 and X 5 is N and X 6 C(R 7 In one aspect of the present invention, X 4 and X 6 is N and X 5 C(R 7 In one aspect of the present invention, X 4 is N and X 5 and X 6 C(R 7 In one aspect of the present invention, X 6 is N and X 4 and X 5 C(R 7 In one aspect of the present invention, R 7 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 7 is an alkyl group optionally substituted with a deuterium atom. In one embodiment of the present invention, R 7is an aryl group which may be substituted with a deuterium atom, an alkyl group, or an aryl group.

[0028] Ar in general formula (2) 3 and Ar 4 Specific examples and preferred ranges of Ar 1 and Ar 2 In one embodiment of the present invention, Ar 1 and Ar 3 In a preferred embodiment of the present invention, Ar 1 and Ar 3 are identical, and Ar 2 and Ar 4 In one aspect of the present invention, Ar 1 ~Ar 4 are identical.

[0029] In a preferred embodiment of the present invention, X 4 ~X 6 is N and L 1 In one embodiment of the present invention, X 4 ~X 6 is N and L 1 is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group (for example, L2, for example, L6). In a preferred embodiment of the present invention, X 4 and X 5 is N and X 6 C(R 7 ) and R 7 is a hydrogen atom or a deuterium atom, and L 1 In one embodiment of the present invention, X 4 and X 5 is N and X 6 C(R 7 ) and R 7 is a hydrogen atom or a deuterium atom, and L 1is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group (for example, L2, for example, L6). In one aspect of the invention, X 4 and X 6 is N and X 5 C(R 7 ) and R 7 is a hydrogen atom or a deuterium atom, and L 1 In one embodiment of the present invention, X 4 and X 6 is N and X 5 C(R 7 ) and R 7 is a hydrogen atom or a deuterium atom, and L 1 is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, and more preferably an unsubstituted phenylene group (for example, L2, for example, L6).

[0030] In one aspect of the invention, X 4 ~X 6 is N and L 1 is a single bond, and Ar 3 and Ar 4 In one aspect of the present invention, X 4 ~X 6 is N and L 1 is a single bond, and Ar 3 and Ar 4 are each independently an at least partially deuterated aryl group. In one aspect of the invention, X 4 and X 5 is N and X 6 C(R 7 ) and R 7 is a hydrogen atom or a deuterium atom, and L 1 is a single bond, and Ar 3 and Ar 4 In one aspect of the present invention, X 4 and X 5 is N and X 6 C(R 7 ) and R 7is a hydrogen atom or a deuterium atom, and L 1 is a single bond, and Ar 3 and Ar 4 are each independently an at least partially deuterated aryl group. In one aspect of the invention, X 4 and X 6 is N and X 5 C(R 7 ) and R 7 is a hydrogen atom or a deuterium atom, and L 1 is a single bond, and Ar 3 and Ar 4 In one aspect of the present invention, X 4 and X 6 is N and X 5 C(R 7 ) and R 7 is a hydrogen atom or a deuterium atom, and L 1 is a single bond, and Ar 3 and Ar 4 are each independently an at least partially deuterated aryl group.

[0031] In a preferred embodiment of the present invention, X 1 and X 4 are identical and X 2 and X 5 are identical and X 3 and X 6 are identical, and Ar 1 and Ar 3 are identical, and Ar 2 and Ar 4 In a more preferred embodiment of the present invention, L 1 is a single bond. In a preferred embodiment of the present invention, X 1 ~X 3 Two of them are N and X 4 ~X 6 Two of them are N. For example, X 1 , X 2 , X 4 , X 5 Only N is included. For example, X 1 , X 3 , X 4 , X6 Only X is N. In one embodiment of the present invention, 1 ~X 3 One of them is N and the other is X 4 ~X 6 Two of them are N. For example, X 1 , X 4 , X 5 Only N is included. For example, X 1 , X 4 , X 6 Only N is included. For example, X 3 , X 4 , X 5 Only N is included. For example, X 3 , X 4 , X 6 Only X is N. In one embodiment of the present invention, 1 ~X 3 One of them is N and the other is X 4 ~X 6 One of the is N. For example, X 1 and X 4 Only N is included. For example, X 3 and X 6 Only N is used.

[0032] In a preferred embodiment of the present invention, R 2 In a preferred embodiment of the present invention, only R 3 In one embodiment of the present invention, R 1 , R 3 , R 4 , R 5 One of them and R 2 In one embodiment of the present invention, R 1 , R 2 , R 4 , R 5 One of them and R 3 are each independently a group represented by general formula (2).

[0033] The compound represented by the general formula (1) preferably does not contain metal atoms, and may be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by the general formula (1) is composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. The compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen ... and nitrogen atoms. Furthermore, the compound represented by the general formula (1) may not contain hydrogen atoms, but may contain deuterium atoms.

[0034] In the present specification, the term "substituent group A" refers to a deuterium atom, 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 atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means one atom or group, or a combination of two or more selected from the group consisting of heteroarylthio groups (e.g., having 5 to 30 ring skeleton atoms), acyl groups (e.g., having 1 to 40 carbon atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), alkynyl groups (e.g., having 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., having 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. In this specification, "substituent group B" means one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, 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 atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms). In this specification, the term "substituent group C" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, 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 atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). In this specification, the term "substituent group D" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, 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 atoms). As used herein, the term "substituent group E" refers to one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms). In the present specification, when it is described as "substituted or unsubstituted" or "optionally substituted", the substituent may be selected, for example, from Substituent Group A, or may be selected from Substituent Group B, or may be selected from Substituent Group C, or may be selected from Substituent Group D, or may be selected from Substituent Group E.

[0035] Specific examples of the compound represented by general formula (1) are shown in the following Tables 1 to 12. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, R 3 ~R 5The structure of each compound is shown individually by specifying each compound. 2 is a group represented by general formula (2), Ar 1 ~Ar 4 is a perdeuterated phenyl group (Ar45), and X 1 ~X 6 is a nitrogen atom (N), and R 1 is a hydrogen atom, and L 1 is a single bond (L1), and R 3 ~R 5 The structures in which is a group specified in Table 1 are shown individually as the structures of compounds 1 to 250. [ka] [Table 1] JPEG2024177837000015.jpg255153

[0036] In Table 2, multiple compounds are listed in each row. 3 ~R 5 The structures of compounds 1 to 250 are shown by displaying them together. For example, in the column of compounds 1 to 50 in Table 2, R 3 ~R 5 In addition, in the case of the columns of compounds 51 to 100 in Table 2, R 4 is fixed to Ar1 (phenyl group), and R 3 and R 5 In the same manner, in the case of the row of compounds 101 to 150 in Table 2, R 4 is fixed at Ar14, and R 3 and R 5 The compounds having the same structure and D1 to D50 are designated as compounds 101 to 150, respectively. Compounds 151 to 250 in Table 2 are also specified in the same manner. That is, the compounds in Table 2 are compounds 1 to 250 specified in Table 1, which are displayed together in five rows.

[0037] [Table 2]

[0038] In the same manner as in Table 2, the structures of compounds 251 to 500 represented by general formula (1b) are specified in Table 3 below. Similarly, in Tables 4 to 11, compounds 501 to 2500 represented by general formulas (1c) to (1j) are specified.

[0039] [Table 3]

[0040] [Table 4]

[0041] [Table 5]

[0042] [Table 6]

[0043] [Table 7]

[0044] [Table 8]

[0045] [Table 9]

[0046] [Table 10]

[0047] [Table 11]

[0048] In Tables 1 to 11, Ar 1 ~Ar 4 The structures of compounds 1 to 2500 were identified as those in which Ar is a perdeuterated phenyl group (Ar45). Table 12 shows the structure of each of compounds 1 to 2500. 1 ~Ar 4 The compounds in which the Ar was changed as shown in Table 12 are displayed in order in the form of a table. In Table 12, in order to make the correspondence easier to understand, compounds 1 to 2500 are also displayed in the first row. In the second row of Table 12, the Ar of compounds 1 to 2500 is displayed in the second row. 2 and Ar 4 The compounds in which both are Ar1 are named Compounds 1(1) to 2500(1), respectively. For example, Compound 1(1) is Compound 1 with Ar 2 and Ar 4 Compound 2(1) is a compound having a structure in which Ar is substituted with Ar1. 2 and Ar 4 Compound 2500(1) is a compound having a structure in which Ar is substituted with Ar1. 2 and Ar 4 The third row of Table 12 shows compounds having a structure in which Ar is substituted with Ar1. 2 and Ar 4 The compounds in which both are Ar2 are named compounds 1(2) to 2500(2) in this order. 1 and Ar 3 , Ar 2 and Ar 4 The compounds are specified in order as shown in Table 12. Among the compounds specified in Table 12, R 1 , R 6 , R 7 is a hydrogen atom, and L 1 is a single bond (L1). [Table 12]

[0049] All compounds identified by numbers in Tables 1 to 12 are considered to be individually disclosed. In addition, when rotamers exist among the specific examples of the compounds, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification. In one embodiment of the present invention, the compound is selected from the group of compounds specified in Tables 1 to 12. In one embodiment of the present invention, the compound is selected from the group of compounds specified in Tables 1 to 11.

[0050] An example of a preferred compound group represented by the general formula (1) is given below. [ka]

[0051] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by deposition, for example, the molecular weight of the compound represented by general formula (1) is preferably 2000 or less, more preferably 1600 or less, and even more preferably 1400 or less, and may be, for example, 1300 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by the general formula (1) may be formed into a film by a coating method regardless of the molecular weight. By using the coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by the general formula (1) has the advantage that it is easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) is easy to apply the coating method to, and is easy to purify to increase the purity.

[0052] It is also conceivable that the present invention can be applied to use a compound containing a plurality of structures represented by general formula (1) in the molecule as a light-emitting material. For example, a polymerizable group may be present in the structure represented by general formula (1) in advance, and the polymer may be polymerized to obtain a polymer, which may be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with another monomer to obtain a polymer having a repeating unit, which may be used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) may be coupled together to obtain a dimer or trimer, which may be used as a light-emitting material.

[0053] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas. [ka]

[0054] In the above general formula, Q represents a group containing a structure represented by general formula (1), L 1 and L 2 represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and further preferably 2 to 10. The linking group is -X 11 -L 11 In this case, it is preferable that X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. 11 represents a linking group, which 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 104each independently represents a substituent, preferably 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 further preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L 1 and L 2 The linking group represented by the following formula can be bonded to any site of general formula (1) constituting Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0055] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0056] A polymer having repeating units containing these formulas can be synthesized by introducing a hydroxyl group into any site of general formula (1), reacting the hydroxyl group as a linker with the compound below to introduce a polymerizable group, and polymerizing the polymerizable group. [ka]

[0057] The polymer containing the structure represented by general formula (1) in the molecule may be a polymer consisting of only repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. The repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type or of two or more types. Examples of repeating units not having the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, examples of repeating units include those derived from monomers having an ethylenically unsaturated bond such as ethylene and styrene.

[0058] The electronic properties of small molecule chemical libraries can be calculated using known ab initio quantum chemical calculations. For example, the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) can be solved using time-dependent density functional theory with a family of functions known as 6-31G*, Becke's three-parameter, and Lee-Yang-Parr hybrid functionals as a basis to screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, the donor moiety ("D") can be selected, for example, for its HOMO energy (e.g., ionization potential) of -6.5 eV or greater, and the acceptor moiety ("A") can be selected, for example, for its LUMO energy (e.g., electron affinity) of -0.5 eV or less. The bridging moiety ("B") prevents overlap between the pi-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly restrict the acceptor and donor moieties to specific conformations. In certain embodiments, the compound library is screened using one or more of the following properties: 1. Emission around a specific wavelength 2. Calculated triplet states above a specific energy level 3. ΔE below a certain value ST value 4. Quantum yield above a certain value 5.HOMO level 6.LUMO Level In one embodiment, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ST The value 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 compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0059] [Method for synthesizing the compound represented by general formula (1)] The compound represented by the general formula (1) can be synthesized by combining known reactions. 1 ~R 5 At least one of the above is a non-fused carbazol-9-yl group. For example, a precursor in which the non-fused carbazol-9-yl group site is a fluorine atom is reacted with a non-fused carbazole which may be substituted with a group consisting of a deuterium atom, an alkyl group, and an aryl group, to synthesize a compound of general formula (1) in which the non-fused carbazol-9-yl group has been introduced.

[0060] [Light-emitting materials containing boron atoms] The organic light-emitting device of the present invention includes a compound represented by general formula (1) and a light-emitting material having a boron atom. The minimum excited singlet energy of the light-emitting material having a boron atom is preferably lower than that of the compound represented by general formula (1). The luminescent material having a boron atom can be a wide variety of boron compounds that can emit light when used in combination with a compound represented by general formula (1). However, in the present invention, boron complexes are not used. In the present invention, it is preferable to use a luminescent material that utilizes the multiple resonance effect of boron atoms and nitrogen atoms. As such a luminescent material, a compound having a structure in which boron atoms and nitrogen atoms are introduced into the skeleton of a polycyclic aromatic compound can be mentioned. In the skeleton, it is preferable that the boron atom and the nitrogen atom have a structure in which they are linked to each other via two carbon atoms that constitute the ring skeleton.

[0061] As the light-emitting material having a boron atom, a compound represented by the following general formula (3) can be preferably used. [ka]

[0062] In the general formula (3), X 1 and X 2 In one embodiment of the present invention, X is a nitrogen atom and the other is a boron atom. 1 is a nitrogen atom, and X 2 is a boron atom. In this case, R 17 and R 18 are bonded to each other to form a single bond to form a pyrrole ring. 1 is a boron atom, and X 2 is a nitrogen atom. In this case, R 21 and R 22 are bonded to each other to form a single bond to form a pyrrole ring. 1 ~R 26 , A 1 , A 2 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17, R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 may be bonded to each other to form a cyclic structure. In a preferred embodiment of the present invention, R 3 and R 6 In a preferred embodiment of the present invention, R 8 , R 10 and R 12 In a preferred embodiment of the present invention, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 22 and R 23 , R 23and R 24 , R 24 and R 25 , R 25 and R 26 None of the pairs are bonded to each other to form a ring structure. For details and specific examples of the compound represented by general formula (3), reference can be made to

[0019] to

[0128] of WO2022 / 270354A1, which is incorporated herein by reference as part of this specification.

[0063] As the light-emitting material having a boron atom, a compound having the following skeleton can also be preferably used. [ka]

[0064] The compound having the above skeleton is preferably a compound represented by the following general formula (4). [ka]

[0065] In the general formula (4), R 1 ~R 10 each independently represents a deuterium atom or a substituent, n1 and n4 to n10 each independently represent an integer of 0 to 5, and n2 and n3 each independently represent an integer of 0 to 4. R 1 ~R 10 is preferably a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group. 1 ~R 10 are each independently a deuterium atom, an alkyl group optionally substituted with a deuterium atom, or an aryl group optionally substituted with a deuterium atom or an alkyl group. 1 ~R 10are each independently a deuterium atom or an alkyl group which may be substituted with a deuterium atom. In one embodiment of the present invention, no ring is further condensed to the skeleton of general formula (4). In one embodiment of the present invention, at least one of n1 to n10 is an integer of 1 or more. In one embodiment of the present invention, at least one of n1 to n10 is an integer of 1 or more, and R 1 ~R 10 At least one of the is a deuterium atom.

[0066] As the light-emitting material having a boron atom, compounds represented by the following general formulas (5) to (24) can also be used.

[0067] [ka]

[0068] In the general formula (5), R 1 , R 3 ~R 16 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 2 represents an acceptor group, or R 1 and R 2 are bonded together to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group. 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16may be bonded to each other to form a cyclic structure. 1 represents O or NR, and R represents a substituent. X 2 ~X 4 Of these, X 3 and X 4 At least one of the groups is O or NR, and the remaining group may be O or NR or may not be linked. When not linked, each of the two ends independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 , C.R. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0069] [ka]

[0070] In the general formula (6), R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R 3 ~R 16 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9and R 2 , R 2 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 1 may be bonded to each other to form a cyclic structure. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0071] [ka]

[0072] In the general formula (7), Z 1 and Z 2 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 ~R 9 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R8 and R 9 may be bonded to each other to form a ring structure. 1 , Z 2 , R 1 and R 2 are bonded together to form a ring, R 2 and R 3 are bonded together to form a ring, R 4 and R 5 A ring formed by bonding together with R 5 and R 6 At least one of the rings formed by bonding to each other is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole, and R 1 ~R 9 At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or 1 and Z 2 At least one of the rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. 1 , C.R. 2 , C.R. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 may be substituted with N.

[0073] [ka]

[0074] In the general formula (8), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2and Z 3 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 Each of Z independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0075] [ka]

[0076] In the general formula (9), X 3 represents an oxygen atom or a sulfur atom, and Z 2 and Z 3 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 4 ~R 7 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R7 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0077] [ka]

[0078] In the general formula (10), X 4 represents an oxygen atom or a sulfur atom, and Z 2 and Z 3 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 4a ~R 7a represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 , R 4a and R 5a , R 5a and R 6a , R 6a and R 7a , R 7a and R 1 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0079] [ka]

[0080] In the general formula (11), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 8 ~R 14 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and Z 3 , Z 3 and R 3 may be bonded to each other to form a cyclic structure.

[0081] [ka]

[0082] In the general formula (12), Z 1 and Z 4 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 15 ~R 17each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and Z 3 , Z 3 and R 3 may be bonded to each other to form a cyclic structure.

[0083] [ka]

[0084] In the general formula (13), Z 1 and Z 5 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 Each of Z independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 2 and Z 5 , Z 5 and Z 3 , Z 3 and R 3 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0085] [ka]

[0086] In the general formula (14), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 21 ~R 27 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 2 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 , R 26 and R 27 may be bonded to each other to form a cyclic structure.

[0087] [ka]

[0088] In the general formula (15), Z 1 and Z 6 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 28 ~R 30 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 2 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and Z 6 may be bonded to each other to form a cyclic structure.

[0089] [ka]

[0090] In the general formula (16), Z 1 and Z 7 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and Z 7 , Z 7 and R 3 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z7 , Z 7 and R 3 At least one pair of is bonded to each other to form a ring structure.

[0091] [ka]

[0092] In the general formula (17), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, R 1 and R 31 ~R 44 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 31 and R 32 , R 32 and R 33 , R 33 and R 34 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , R 42 and R 43 , R 43 and R 44 may be bonded to each other to form a cyclic structure.

[0093] [ka]

[0094] In the general formula (18), Z1 and Z 8 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 51 ~R 60 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and Z 1 , R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 , R 60 and Z 8 may be bonded to each other to form a cyclic structure.

[0095] [ka]

[0096] In the general formula (19), Z 1 , Z 8 and Z 9 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 61 ~R 66 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , R 66 and Z 8 may be bonded to each other to form a cyclic structure.

[0097] [ka]

[0098] In the general formula (20), Z 1 , Z 9 and Z 10 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 67 ~R 69 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 70 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , Z 9 and R 67 , R 67 and R 68 , R 68 and R 69 , R 69 and Z 10 , Z 10 and R 70 may be bonded to each other to form a cyclic structure.

[0099] [ka]

[0100] In the general formula (21), Z 1 , Z 11 and Z 12each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 72 ~R 74 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 71 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 71 and Z 11 , Z 11 and R 72 , R 72 and R 73 , R 73 and Z 74 , R 74 and Z 12 may be bonded to each other to form a cyclic structure.

[0101] [ka]

[0102] In the general formula (22), Z 1 and Z 11 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 76 ~R 82 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R 75 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 75 and Z 11 , Z 11 and R 76 , R 76 and R 77 , R 77 and R 78 , R78 and R 79 , R 79 and R 80 , R 80 and R 81 , R 81 and R 82 may be bonded to each other to form a cyclic structure.

[0103] [ka]

[0104] In the general formula (23), X 5 represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded; R 101 ~R 130 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 101 and R 102 , R 102 and R 103 , R 103 and R 104 , R 104 and R 105 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 109 and R 110 , R 110 and R 111 , R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 114 and R 115 , R 115 and R 116 , R 116 and R 117 , R 117 and R 118 , R 118 and R 119 , R 119 and R 120 , R 120and R 121 , R 121 and R 122 , R 122 and R 123 , R 123 and R 124 , R 124 and R 125 , R 125 and R 126 , R 126 and R 127 , R 127 and R 128 , R 128 and R 129 , R 129 and R 130 , R 130 and R 101 may be bonded to each other to form a cyclic structure.

[0105] [ka]

[0106] In the general formula (24), R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z 1 and Z 2 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 3 ~R 9 each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 , R 2 , Z 1 and Z 2 At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. 1 and Z 1 , Z 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and Z 2 , Z2 and R 2 , R 2 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 may be substituted with N.

[0107] In the organic light-emitting device of the present invention, the content of the compound having a boron atom is preferably smaller than that of the compound represented by general formula (1). The content of the compound having a boron atom may be selected within the range of 0.01 to 50% by weight, 0.1 to 30% by weight, or 0.5 to 10% by weight of the content of the compound represented by general formula (1). In the organic light-emitting device of the present invention, two or more types of compounds represented by general formula (1) or two or more types of compounds having a boron atom may be used.

[0108] [Host material] In the organic light-emitting device of the present invention, the layer (light-emitting layer) containing the compound represented by the general formula (1) and the compound having a boron atom may further contain a host material. The content of the host material in the layer is 20% by weight or more, preferably 30% by weight or more, for example 40% by weight or more. The upper limit is 99% by weight or less, and may be, for example, 90% by weight or less, 70% by weight or less, or 50% by weight or less. In one embodiment, the host material of the light-emitting layer is an organic compound having hole transporting and electron transporting functions. In one embodiment, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In one embodiment, the host material of the light-emitting layer is an organic compound having a high glass transition temperature. The lowest excited singlet energy and the lowest excited triplet energy of the host material are preferably higher than those of the compound represented by general formula (1) and the compound having a boron atom.

[0109] In some embodiments, the host material is selected from the group consisting of: [ka] JPEG2024177837000055.jpg255168

[0110] In a preferred embodiment of the present invention, the host material is a compound having a structure represented by the following general formula (25): [ka]

[0111] In the general formula (25), X 11 is O, S, N(R A ) or C(R B )(R C In one aspect of the present invention, X 11 is O, S or N(R A In one aspect of the present invention, X 11 is O or S. In one embodiment of the present invention, X 11 is N(R A In one aspect of the present invention, X 11 is O. In one embodiment of the present invention, X 11 is S. X 11 is O, S or C(R B )(R C ), then L is (R 115 )n is bonded to the benzene ring to which X 11 N(R A ), then L is (R115 )n is attached to the benzene ring or X 11 The bond extending from L to the right is represented by (R 115 )n is attached to the benzene ring to which it is attached, or X 11 When N, X 11 (i.e. N).

[0112] In the general formula (25), A 11 and A 12 are each independently a benzene ring, a furan ring, a thiol ring, a pyrrole ring or a cyclopentadiene ring, and these rings may be further condensed with other rings or may be substituted. 11 is a benzene ring. In a preferred embodiment of the present invention, A 12 is a benzene ring. In a further preferred embodiment of the present invention, A 11 and A 12 are both benzene rings. 11 and A 12 At least one of A is a furan ring, a thiol ring, a pyrrole ring, or a cyclopentadiene ring. 11 and A 12 At least one of A is a furan ring. 11 and A 12 At least one of A is a thiol ring. 11 and A 12 At least one of A is a pyrrole ring. 11 and A 12 At least one of these is a cyclopentadiene ring. The benzene ring, furan ring, thiol ring, pyrrole ring and cyclopentadiene ring may further be condensed with another ring. The condensed ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring and an aliphatic heterocycle, and may be a ring in which two or more of these are condensed. An aromatic hydrocarbon ring, an aromatic heterocycle, or a ring in which two or more of these are condensed is preferable. An example of the aromatic hydrocarbon ring is a benzene ring. The aromatic heterocycle means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton constituent atom, and 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 embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the aromatic heterocycle. The aliphatic hydrocarbon ring is preferably a hydrocarbon ring that does not exhibit aromaticity, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. For example, a cyclopentadiene ring can be adopted. The aliphatic heterocycle means a ring that contains a heteroatom as a ring skeleton-constituting atom and does not exhibit aromaticity, 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 11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are condensed. 11 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are condensed. 11 is a benzene ring, and the furan ring of benzofuran or the thiophene ring of benzothiophene is condensed to the benzene ring. 11 is fused to the furan ring of the benzofuran. 11 is fused to the thiophene ring of the benzothiophene. 12is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are condensed. 12 is a benzene ring, and the benzene ring is further condensed with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are condensed. 12 is a benzene ring, and the furan ring of benzofuran or the thiophene ring of benzothiophene is condensed to the benzene ring. 12 is fused to the furan ring of the benzofuran. 12 is condensed with the thiophene ring of benzothiophene. A 11 Or A 12 The hydrogen atoms of the rings constituting the ring may be substituted with deuterium atoms or substituents. The substituents can be selected from any of the substituent groups A to E, for example, from the substituent group E. In one embodiment of the present invention, A 11 Or A 12 The ring constituting A may be substituted with one atom or group, or a combination of two or more atoms selected from the group consisting of a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, and a cyano group. 11 Or A 12 The ring constituting A may be substituted with a deuterium atom, an alkyl group, an aryl group, or a combination thereof. 11 Or A 12 At least one of the rings constituting A is substituted with a deuterium atom, an alkyl group, an aryl group, or a combination thereof. 11 Or A 12 When a pyrrole ring is included as a ring constituting the ring, it is preferable that a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group is bonded to a nitrogen atom constituting the ring skeleton of the pyrrole ring (the same applies to the nitrogen atom of the indole ring described below). 11 Or A 12When two or more hydrogen atoms of the ring constituting the ring are replaced, they may be replaced by the same atom or group or by different atoms or groups.

[0113] In the general formula (25), R 111 ~R 114 , R B , R C R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. 115 R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a cyano group, or a bond to L (i.e., a single bond to L). A represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond with L (i.e., a single bond to L). For the aryl group, the heteroaryl group, and the alkyl group, the above explanations of "aryl group", "heteroaryl group", and "alkyl group" can be referred to. The number of carbon atoms of the aryl group is preferably 6 to 14, and examples thereof include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. The heteroaryl group is preferably composed of a 5-membered or 6-membered ring, and examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a dibenzofuryl group, and a dibenzothienyl group. The number of carbon atoms of the alkyl group is preferably 1 to 6, and examples thereof include a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group. These aryl groups, heteroaryl groups, and alkyl groups may be substituted, and when substituted, they are preferably substituted with one atom or group or a combination of two or more selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, and a cyano group, and more preferably substituted with one atom or group or a combination of two or more selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group. 112is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a cyano group. 111 ~R 114 are each independently a hydrogen atom or a deuterium atom. R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , two adjacent R 115 , R B and R C may be bonded to each other to form a cyclic structure. The cyclic structure referred to here is as defined above in A 11 and A 12 In one embodiment of the present invention, R 111 and R 112 , R 112 and R 113 , R 113 and R 114 are bonded together to form a benzofuran ring (fused with a furan ring), a benzothiophene ring (fused with a thiophene ring), or an indole ring (fused with a pyrrole ring).

[0114] In one embodiment of the present invention, the group bonded to L from the left in general formula (25) is a substituted or unsubstituted carbazol-9-yl group. For example, it is a carbazol-9-yl group in which at least one (preferably both) of the 3-position and the 6-position is substituted with a deuterium atom, an alkyl group, an aryl group, or a combination of these groups. It may also be an unsubstituted carbazol-9-yl group. In one embodiment of the present invention, the group bonded to L from the left in general formula (25) is a substituted or unsubstituted benzofuro[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzofuro[3,2-c]carbazol-5-yl group. In one embodiment of the present invention, the group bonded to L from the left in general formula (25) is a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group. In one embodiment of the present invention, the group bonded to L from the left in general formula (25) is a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazol-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazol-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group. In one embodiment of the present invention, the group bonded to L from the right in general formula (25) may also be any of the groups exemplified above as the group bonded to L from the left, provided that the group is not an unsubstituted carbazol-9-yl group.

[0115] In the following, specific examples of groups that can be used as the group bonded to the left of L in general formula (25) are given. However, the groups that can be used in the present invention are not limited to these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, Z2 and Z3 are substituted with methyl groups. * indicates the bonding position to L. [ka] JPEG2024177837000058.jpg226170JPEG2024177837000059.jpg211170JPEG2024177837000060.jpg235170JPEG2024177837000061.jpg215170 JPEG2024177837000062.jpg221170JPEG2024177837000063.jpg212170JPEG2024177837000064.jpg237170JPEG2024177837000065.jpg131170

[0116] In addition to the above specific examples, groups in which all hydrogen atoms of the alkyl groups Z2, Z3, Z5, Z7 to Z12, Z87 to Z104, and Z179 to Z196 are replaced with deuterium atoms are exemplified here as Z2(m), Z3(m), Z5(m), Z7(m) to Z12(m), Z87(m) to Z104(m), and Z179(m) to Z196(m), respectively. Also, groups in which the phenyl groups (CH) of Z4 to Z6, Z19 to Z86, and Z111 to Z178 are replaced with deuterated C6D5 are exemplified here as Z4(p) to Z6(p), Z19(p) to Z86(p), and Z111(p) to Z178(p), respectively. Furthermore, groups in which all hydrogen atoms in Z1 to Z196 are deuterated are exemplified here as Z1(D) to Z196(D), respectively.

[0117] In general formula (25), specific examples of the group that can be bonded to the right of L include the above Z2 to Z196 and their deuterium atom-substituted derivatives, as well as the specific examples shown below. However, the groups that can be employed in the present invention are not limited to these specific examples. Note that in the following specific examples, methyl groups are omitted. * indicates the bonding position to L. [ka] JPEG2024177837000067.jpg230170JPEG2024177837000068.jpg246170JPEG2024177837000069.jpg243170JPEG2024177837000070.jpg102170

[0118] In addition to the above specific examples, groups in which the methyl groups (CH3) of X31 to X33 and X64 to X79 are replaced with deuterated CD3 are exemplified here as X31(m) to X33(m) and X64(m) to X79(m), respectively. Groups in which the phenyl groups (CH5) of X5 to X21, X38 to X54 and X68 to X70 are replaced with deuterated C6D5 are exemplified here as X5(p) to X21(p), X38(p) to X54(p) and X68(p) to X70(p), respectively. Furthermore, groups in which all hydrogen atoms of X1 to X79 are deuterated are exemplified here as X1(D) to X79(D), respectively.

[0119] In the general formula (25), n represents an integer of 3 or 4. 11 is O, S or C(R B )(R C ), then L is (R 115 )n is bonded to the benzene ring to which it is attached, so n is 3. X 11 N(R A ) and L is (R 115 ) n is bonded to the benzene ring to which it is attached, n is 3, and X 11 N(R A ) where L is X 11When R is bonded to N, n is 4. 115 may be the same or different from each other.

[0120] L in the general formula (25) represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group to which two or more of these are bonded. For the aryl structure of the arylene group and the heteroaryl structure of the heteroarylene group, the above explanations of "aryl group" and "heteroaryl group" can be referred to. The arylene group and the heteroarylene group may be substituted, and if substituted, they are preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, an alkyl group, and a cyano group, or a group combining two or more of these, and more preferably substituted with one atom or group selected from the group consisting of a deuterium atom, an aryl group, a heteroaryl group, and an alkyl group, or a group combining two or more of these. If substituted, they are preferably methyl, ethyl, isopropyl, tert-butyl, phenyl, or deuterated versions thereof. In one embodiment of the present invention, L is an unsubstituted arylene group. Specific examples of L are given below. However, L that can be adopted in the present invention is not limited to these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates a bond position. L1 is a single bond.

[0121] [ka]

[0122] In one embodiment of the present invention, the group bonded from the left of L in general formula (25) is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (embodiment 1). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z12 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (embodiment 2). In one embodiment of the present invention, the group bonded from the left of L is selected from Z13 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X79 and their deuterated forms (embodiment 3). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X66 and their deuterated forms (embodiment 4). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X33 and their deuterated forms (Aspect 5). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X1 to X21, X31 to X33 and their deuterated forms (Aspect 6). In one embodiment of the present invention, the group bonded from the left of L is selected from Z1 to Z196 and their deuterated forms, and the group bonded from the right of L is selected from X22 to X30 and their deuterated forms (Aspect 7). In one embodiment of the invention, in embodiment 1, L is L1. In one embodiment of the invention, in embodiment 2, L is L1. In one embodiment of the invention, in embodiment 3, L is L1. In one embodiment of the invention, in embodiment 4, L is L1. In one embodiment of the invention, in embodiment 5, L is L1. In one embodiment of the invention, in embodiment 6, L is L1. In one embodiment of the invention, in embodiment 7, L is L1. In one embodiment of the invention, in embodiment 1, L is L6. In one embodiment of the invention, in embodiment 2, L is L6. In one embodiment of the invention, in embodiment 3, L is L6. In one embodiment of the invention, in embodiment 4, L is L6. In one embodiment of the invention, in embodiment 5, L is L6. In one embodiment of the invention, in embodiment 6, L is L6. In one embodiment of the invention, in embodiment 7, L is L6. In one embodiment of the invention, in embodiment 1, L is L14. In one embodiment of the invention, in embodiment 2, L is L14. In one embodiment of the invention, in embodiment 3, L is L14. In one embodiment of the invention, in embodiment 4, L is L14. In one embodiment of the invention, in embodiment 5, L is L14. In one embodiment of the invention, in embodiment 6, L is L14. In one embodiment of the invention, in embodiment 7, L is L14. In one embodiment of the invention, in embodiment 1, L is L16. In one embodiment of the invention, in embodiment 2, L is L16. In one embodiment of the invention, in embodiment 3, L is L16. In one embodiment of the invention, in embodiment 4, L is L16. In one embodiment of the invention, in embodiment 5, L is L16. In one embodiment of the invention, in embodiment 6, L is L16. In one embodiment of the invention, in embodiment 7, L is L16.

[0123] Specific examples of the compound represented by general formula (25) are shown below. However, the compound represented by general formula (25) that can be used in the present invention is not limited to the following specific examples.

[0124] [ka]

[0125] In addition to the above specific examples, compounds in which all hydrogen atoms in the substituted or unsubstituted carbazol-9-yl groups in H1 to H13 are replaced with deuterium atoms are exemplified here as H1(d) to H13(d), respectively. Compounds in which all hydrogen atoms in H1 to H13 are replaced with deuterium atoms are exemplified here as H1(D) to H13(D), respectively.

[0126] The molecular weight of the compound represented by general formula (25), for example, when it is intended to form an organic layer containing the compound represented by general formula (25) into a film by a vapor deposition method and use it, is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 800 or less, and may be, for example, 600 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (25).

[0127] The compound represented by the general formula (25) is preferably one having a smaller dipole moment because the orientation of the film formed therefrom is higher. The dipole moment is preferably smaller than 2.3, more preferably smaller than 2.0, even more preferably smaller than 1.7, and even more preferably smaller than 1.4.

[0128] As the compound represented by the general formula (25), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected. For example, as the compound represented by the general formula (25), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms can be selected. For example, as the compound represented by the general formula (25), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms can be selected. For example, as the compound represented by the general formula (25), a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms can be selected.

[0129] [Organic light-emitting element] The organic light-emitting device of the present invention includes a compound represented by general formula (1) and a light-emitting material having a boron atom (excluding boron complexes). The layer (light-emitting layer) including the compound represented by general formula (1) and the light-emitting material having a boron atom may further include a host material. In this case, the compound represented by general formula (1) functions as an assist dopant. In the light-emitting layer of the organic light-emitting device of the present invention, a delayed fluorescent material other than the compound represented by formula (1) may be used in combination. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. JP 2013-256490 A, paragraphs 0009 to 0046 and 0093 to 0134; JP 2013-116975 A, paragraphs 0008 to 0020 and 0038 to 0040; WO 2013 / 133359 A, paragraphs 0007 to 0032 and 0079 to 0084; WO 2013 / 161437 A, paragraph 0 JP 2014-9352 A, paragraphs 0007-0041 and 0060-0069, JP 2014-9224 A, paragraphs 0008-0048 and 0067-0076, JP 2017-119663 A, paragraphs 0013-0025, JP 2017-119664 A, paragraphs 0013-0026, JP 2017-119664 A, The compounds included in the general formulas described in paragraphs 0012 to 0025 of JP 017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO 2018 / 047853 A, particularly the example compounds, which are capable of emitting delayed fluorescence, are included.In addition, the following publications are included herein: JP2013-253121A, WO2013 / 133359A, WO2014 / 034535A, WO2014 / 115743A, WO2014 / 122895A, WO2014 / 126200A, WO2014 / 136758A, WO2014 / 133121A, WO20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714A, WO2015 / 129715A, WO2015 / 13350 The luminescent materials described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541, which are capable of emitting delayed fluorescence, can be preferably used. Note that the above publications described in this paragraph are hereby incorporated by reference as part of this specification. The organic light-emitting element of the present invention may include light emission from a compound represented by general formula (1). In one embodiment of the present invention, the amount of light emitted from the compound represented by general formula (1) is 10% or less, for example 1% or less, for example 0.1% or less, of the amount of light emitted from a light-emitting material having a boron atom. In one embodiment of the present invention, 90% or more of the amount of light emitted from the organic light-emitting element is light emission from a light-emitting material having a boron atom, for example 99% or more, for example 99.9% or more is light emission from a light-emitting material having a boron atom. In some embodiments, the light-emitting layer does not contain any metal element (boron atoms are not included in the metal elements in the present invention). In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, boron atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, boron atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material that contains all of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, boron atoms, and oxygen atoms, and does not contain any other elements. In the organic light-emitting device of the present invention, the compound represented by formula (1) may be used in a layer other than the light-emitting layer. For example, the compound represented by formula (1) may be used in a layer adjacent to the light-emitting layer.

[0130] When forming layers of an organic light-emitting device, a film forming technique can be used. In an embodiment, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In an embodiment, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In an embodiment, the film containing the compound of the present invention can be formed by a dry process. In an embodiment, the dry process can be a vacuum deposition method, but is not limited thereto. When the vacuum deposition method is adopted, 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 a single deposition source is used, a mixed powder in which powders of the compounds are mixed may be used, or a compression molded body in which the mixed powder is compressed may be used, or a mixture in which each compound is heated, melted, and cooled may be used. In an embodiment, a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source can be formed by performing co-deposition under conditions in which the deposition rates (weight reduction rates) of the multiple compounds contained in a single deposition source are the same or almost the same. If the multiple compounds are mixed in the same composition ratio as the composition ratio of the film to be formed and used as the deposition source, a film having a desired composition ratio can be easily formed. In an embodiment, a temperature at which each compound to be co-deposited has the same weight reduction rate can be specified, and the temperature can be used as the temperature during co-deposition.

[0131] In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer is at 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 the other light-emitting materials contained in the light-emitting layer. In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least a light-emitting layer. In some embodiments, the organic layer includes only a light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer with a hole injection function, and the electron transport layer may be an electron injection transport layer with an electron injection function.

[0132] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0133] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0134] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or 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 capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering. In some embodiments, the film is patterned by a photolithographic method. In some embodiments, if the pattern does not need to be highly accurate (e.g., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for evaporation 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 formation method, such as a printing method or a coating method, is used. In some embodiments, the anode has a transmittance of more than 10% when emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0135] cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is 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-injecting metal and a second metal, which is a stable metal having a higher work function than the electron-injecting 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-injecting properties 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 cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, one of the anode and cathode of the organic electroluminescent device is transparent or semi-transparent to transmit emitted light. In some embodiments, a transparent or semi-transparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semi-transparent cathode, hi some embodiments, an element includes an anode and a cathode, both of which are transparent or semi-transparent.

[0136] Injection layer: An injection layer is a layer between an electrode and an organic layer. In some embodiments, the injection layer reduces driving voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the 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 is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as the hole injection material are given below.

[0137] [ka]

[0138] Next, preferred examples of compounds that can be used as the electron injection material will be given. [ka]

[0139] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron barrier layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole barrier layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron 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 layers that have both the functions of an electron barrier layer and of an exciton barrier layer.

[0140] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport, 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 materials used for the hole blocking layer can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.

[0141] [ka]

[0142] Electron barrier layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer blocks electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron blocking material are given below.

[0143] [ka] JPEG2024177837000077.jpg46170

[0144] Exciton blocking layer: The exciton blocking 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 blocking layer allows for 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 blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, the layer may be present between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is present on the cathode side, the layer may be present between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0145] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. 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 hole transport materials are given below.

[0146] [ka]

[0147] Electron transport layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as electron transport materials are given below.

[0148] [ka]

[0149] In addition, examples of compounds that can be added to each organic layer are given below, which may be used as stabilizing materials, for example.

[0150] [ka]

[0151] Although the preferred materials that can be used in the organic electroluminescence element are specifically exemplified, the materials that can be used in the present invention are not limited to the following exemplified compounds. In addition, even if a compound is exemplified as a material having a specific function, it can be diverted to a material having other functions.

[0152] device: In some embodiments, the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein may be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions may be useful for facilitating charge or energy transfer within the device and / or as hole transport materials, such as organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0153] Bulb or Lamp: In some embodiments, the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device 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, four, or more colors. In some embodiments, the device comprises: a circuit board having a first side having a mounting surface and an opposing second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light comprises 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.

[0154] Display or Screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful in two-sided etching to provide pixels of unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of an OLED display. The corresponding artwork pattern design allows for the placement of very steep narrow tie bars between pixels in the vertical direction, as well as large wide angled openings in the horizontal direction. This allows for the fine patterning of pixels required for high resolution displays while optimizing chemical vapor deposition onto the TFT backplane. The internal patterning of the pixel allows for the construction of three-dimensional pixel openings of various aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles in the pixel area protects etching in certain areas until those particular patterns are undercut and removed from the substrate. At that point, all pixel areas are treated with similar etch rates, but the depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with different protection rates within the pixel, allowing for the localized deep etching required to create steep vertical bevels. The preferred material for the deposition mask is Invar. Invar is a metal alloy that is cold rolled into long thin sheets at steel mills. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask. A suitable and low-cost method for forming open areas in the deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0155] How the device is manufactured: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Usually, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Usually, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel.

[0156] In another aspect of the 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 on the barrier layer in units of cell panels; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example made of SiNx, and the ends of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film helps the mother panel to be cut softly into cell panels. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed at the same time as the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, the 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 the display unit or the encapsulation layer.

[0157] Each of the organic film and the planarization film may include one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide prior to forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate prior to cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer for covering 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, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0158] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source / drain electrode of a TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit 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 units and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films 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 an interval with each of the plurality of display units. In some embodiments, the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the end of the barrier layer.

[0159] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and the carrier substrate is then separated. In some embodiments, a barrier layer is formed on a surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0160] In some embodiments, the method further includes a step of cutting along the interface, where a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on the TFT layer to cover the TFT layer. At the same time as the planarization film, which is made of, for example, polyimide or acrylic, is formed, the groove of the interface is covered with an organic film, which is made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the groove at the interface by having the organic film absorb the impact that occurs. That is, if all the barrier layers are completely exposed without the organic film, when each cell panel is cut along the groove at the interface, the impact that occurs will be transmitted to the barrier layer, thereby increasing the risk of cracks. However, in one embodiment, the groove of the interface between the barrier layers is covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel can be cut softly and prevent cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface are spaced apart from each other. For example, when the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining part of the organic film, so the organic film and the planarization film are spaced apart from each other so that the organic film is spaced apart from the display unit.

[0161] 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. Thus, 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 irradiated onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, the grooves at the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting. In some embodiments, the barrier layer is prevented from cracking during cutting. In some embodiments, the methods reduce product defect rates and stabilize product quality. Another embodiment 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 the edges of the barrier layer. EXAMPLES

[0162] The characteristics of the present invention will be described in more detail below with reference to synthesis examples and examples. The materials, processing contents, processing procedures, etc. shown below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below. The evaluation of the emission characteristics was performed using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics C4334).

[0163] (Synthesis Example 1) Synthesis of Compound T1 [ka]

[0164] Under a nitrogen stream, potassium carbonate (15.7 g, 113.8 mmol) was added to a solution of compound a (10.0 g, 16.2 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (17.1 g, 97.6 mmol) in N,N-dimethylformamide (DMF, 500 mL), and the mixture was stirred at 150 °C for 24 hours. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in heated o-dichlorobenzene (ODCB), and the solution was used for charging and purification by column chromatography (toluene: hexane = 1:1). Further recrystallization from toluene gave yellow compound T1 (14.8 g, 13.7 mmol, yield 84%). 1 H-NMR (400 MHz, CDCl3): δ 9.39 (s, 1H). ASAP MS Spectral Analysis: C 72 HD 44 N9: Theoretical value 1080.5, Observed value 1081.2

[0165] Example 1: Preparation and evaluation of organic electroluminescence device Each thin film was deposited on a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm by vacuum deposition at a vacuum degree of 5.0 × 10 -5The layers were laminated at 1000 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed on top of that to a thickness of 30 nm, TrisPCz was further formed on top of that to a thickness of 10 nm, and H1' was formed on top of that to a thickness of 5 nm. Next, H1', ​​T1, and D1 were co-evaporated from different evaporation sources to form a layer with a thickness of 40 nm to serve as the light-emitting layer. The concentration of H1' in the light-emitting layer was 34.2 wt%, the concentration of T1 was 65.0 wt%, and the concentration of D1 was 0.8 wt%. Next, SF3-TRZ 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 30 nm. The concentrations of Liq and SF3-TRZ in this layer were 30 wt% and 70 wt%, 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 a cathode, thereby producing an organic electroluminescence element, Element 1. Comparative element 1 was prepared in the same manner except that comparative compound T was used in place of T1. Each element was fabricated at 6.3mA / cm 2 The external quantum efficiency (EQE) was measured by driving the device at 1000 V. The orientation degree (S value) of compound T1 and comparative compound T in the light-emitting layer was also measured. The orientation degree was measured according to the method described in Scientific Reports 2017, The orientation of the light-emitting material in the light-emitting layer was determined by the method described in Jpn. Appln. Phys. 2004, 143, 1111-1155, 2004. The results are shown in the following table. It was confirmed that the organic light-emitting device satisfying the conditions of the present invention has high orientation of the light-emitting material in the light-emitting layer and excellent light-emitting characteristics. [Table 13] [ka]

[0166] Example 2: Preparation of an organic electroluminescence device An organic electroluminescent device, Device 2, is prepared following the same procedure as in Example 1, except that D2 is used instead of D1.

[0167] Example 3: Preparation of an organic electroluminescence device An organic electroluminescent device, Device 3, is prepared following the same procedure as in Example 1, except that D3 is used instead of D1.

[0168] [ka] [Industrial Applicability]

[0169] By using the compound represented by the general formula (1) in combination with a boron compound, a light-emitting device having good alignment in the light-emitting layer and excellent light-emitting properties can be provided. Therefore, the present invention has a high industrial applicability.

Claims

1. Compounds represented by the following general formula (1), and Luminescent materials containing boron atoms, excluding luminescent materials that are boron complexes. Organic light-emitting element containing [a specific component]. 【Chemistry 1】 In general formula (1), R １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a non-fused carbazole-9-yl group optionally substituted with one or more combinations selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group represented by the following general formula (2). Also, R ２ or R ３ is a group represented by the following general formula (2), and at least one of R １ ~R ５ is the non-fused carbazole-9-yl group. At least one of X １ ~X ３ is N, and the rest represents C(R ６ ). R ６ represents a hydrogen atom, a deuterium atom, or a substituent. Ar １ and Ar ２ each independently represents a substituted or unsubstituted aryl group. 【Chemistry 2】 In general formula (2), X ４ ~X ６ At least one of them is N, and the rest are C(R) ７ ) represents R ７ Ar represents a hydrogen atom, a deuterium atom, or a substituent. ３ and Ar ４ Each of these independently represents a substituted or unsubstituted aryl group. １ * represents a single bond or a divalent linking group. * indicates the bond position.

2. R ２ The organic light-emitting element according to claim 1, wherein is a group represented by the general formula (2).

3. R ３ The organic light-emitting element according to claim 1, wherein is a group represented by the general formula (2).

4. R １ ~R ５ The organic light-emitting element according to claim 1, wherein two or more of these are the non-fused carbazole-9-yl groups.

5. R １ ~R ５ The organic light-emitting element according to claim 1, wherein three of these are the non-fused carbazole-9-yl groups.

6. X １ ~X ３ The organic light-emitting element according to claim 1, wherein two or more of the elements are N.

7. X ４ ~X ６ The organic light-emitting element according to claim 1, wherein two or more of the elements are N.

8. L １ The organic light-emitting element according to claim 1, wherein the bond is a single bond.

9. R １ The organic light-emitting element according to claim 1, wherein is a hydrogen atom.

10. The organic light-emitting element according to claim 1, having at least one deuterium atom.

11. The organic light-emitting element according to any one of claims 1 to 10, wherein the light-emitting material having boron atoms is a compound represented by the following general formula (3). 【Transformation 3】 [In general formula (3), X １ and X ２ One atom is a nitrogen atom, and the other is a boron atom. １ ~R ２６ A １ A ２ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ They may be joined to each other to form a ring structure. However, X １ When R is a nitrogen atom, １７ and R １８ They bond to each other to form a single bond and create a pyrrole ring, X ２ When it is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond and form a pyrrole ring.]

12. R in general formula (3) ３ and R ６ The organic light-emitting element according to claim 11, wherein both are substituents.

13. R in general formula (3) ８ , R １０ and R １２ The organic light-emitting element according to claim 11, wherein all of them are substituents.

14. X of the general formula (3) １ is a nitrogen atom, and X ２ is a boron atom. The organic light-emitting device according to claim 11.

15. R in general formula (3) １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ The organic light-emitting element according to claim 11, wherein none of the sets are bonded to each other to form a ring structure.

16. The organic light-emitting element according to any one of claims 1 to 10, wherein the light-emitting material having the boron atom is a compound having the following skeleton. 【Chemistry 4】

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