Organic light emitting element

Abstract

This organic light emitting element, which uses a compound of the general formula and a boron compound, has excellent light emission characteristics. In the general formula, 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 a 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.

Description

Organic light-emitting devices

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

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

[0003] Delayed fluorescent materials are materials that, in an excited state, undergo reverse intersystem crossing from an excited triplet state to an excited singlet state, and then emit fluorescence when returning from the excited singlet state to the ground state. Fluorescence via this route is observed later than fluorescence from the excited singlet state (normal fluorescence) directly generated from the ground state, and is therefore called delayed fluorescence. Here, for example, when a light-emitting compound is excited by carrier injection, the probability of occurrence of the excited singlet state and the excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency when only fluorescence from the directly generated excited singlet state is used. On the other hand, delayed fluorescent materials can utilize not only the excited singlet state but also the excited triplet state for fluorescence emission via the above-mentioned reverse intersystem crossing route, thereby achieving higher luminous efficiency than ordinary fluorescent materials.

[0004] Since this principle was clarified, various researches have led to the discovery of various delayed fluorescent materials. These include many 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).

[0005] WO2022 / 270600A1

[0006] On the other hand, even for materials that emit delayed fluorescence, those with extremely good properties and no practical problems have not yet been provided. Furthermore, when used in organic light-emitting elements such as organic electroluminescence elements, elements with excellent performance cannot be provided unless the usage mode is devised. For this reason, improving delayed fluorescent materials and improving the performance of organic light-emitting elements have been long-standing challenges, but solutions to these challenges are still being found through trial and error. Under these circumstances, the present inventors have conducted extensive research with the aim of providing an organic light-emitting element with excellent light-emitting properties.

[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): [In general formula (1), R １ ~R ５ each independently represents 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 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), and R １ ~R ５ At least one of X is the non-fused carbazol-9-yl group. １ ~X ３ At least one of the groups is N, and the rest are C(R ６ ) represents. ６ represents a hydrogen atom, a deuterium atom or a substituent. １ and Ar ２ each independently represents a substituted or unsubstituted aryl group. In general formula (2), X ４ ~X ６ At least one of the groups is N, and the rest are C(R ７ ) represents. 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 a bonding position.] [2] R ２ [3] The organic light-emitting element according to [1], wherein R is a group represented by the general formula (2). ３ [4] The organic light-emitting element according to [1], wherein R is a group represented by the general formula (2). １ ~R ５ [5] The organic light-emitting device according to any one of [1] to [3], wherein two or more of R １ ~R ５ [6] The organic light-emitting device according to any one of [1] to [3], wherein three of X are the non-fused carbazol-9-yl group. １ ~X ３ [7] The organic light-emitting device according to any one of [1] to [5], wherein two or more of X are N. ４ ~X ６ [8] The organic light-emitting device according to any one of [1] to [6], wherein two or more of the following are N: １ [9] The organic light-emitting device according to any one of [1] to [7], wherein R is a single bond. １ is a hydrogen atom.

[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): [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 ２R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other as a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other as a single bond to form a pyrrole ring.]

[12] R in general formula (3) ３ and R ６

[13] The organic light-emitting element according to

[11] , wherein R in general formula (3) is a substituent. ８ , R １０ and R １２

[14] The organic light-emitting element according to

[11] or

[12] , wherein X in general formula (3) is a substituent. １ is a nitrogen atom, and X ２

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

[11] to

[13] , wherein R in general formula (3) is a boron atom. 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

[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:

[0008] The organic light-emitting device of the present invention has excellent light-emitting properties.

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

[0010] [Compound Represented by General Formula (1)] The compound represented by the following general formula (1) will be explained.

[0011] 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, a non-fused carbazol-9-yl group which may be substituted with one or a combination of two or more selected from the group consisting of 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), and R １ ~R ５ At least one of X is the non-fused carbazol-9-yl group. １ ~X ３ At least one of the groups is N, and the rest are C(R６ ) represents. 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 groups 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 substituent of the alkyl group is one or more 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 can 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 monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and 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 naphthalen-1-yl group, or a substituted or unsubstituted naphthalen-2-yl group, preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. 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 embodiment of the present invention, the aryl group is unsubstituted. １ ~R ５ , Ar １ and Ar ２ Specific examples of substituted or unsubstituted aryl groups that can be used are listed below. However, the aryl 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, * indicates a bonding position. Also, methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.

[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 this order. １ ~R ５ The aryl group that R can take is selected from the group consisting of Ar1 to Ar69. １ ~R ５ The aryl group that R can take is Ar1 or Ar45. In one embodiment of the present invention, R １~R ５ The aryl group that R can take is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, and Ar46 to Ar55. １ ~R ５ 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 that R can take is selected from the group consisting of Ar21 to Ar25 and Ar65 to Ar69. １ ~R ５ The aryl group that can be taken by Ar is selected from the group consisting of Ar1, Ar12 to Ar14, Ar23, Ar36 to Ar38, Ar45, Ar56 to Ar58, and Ar67. 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 that can be taken by Ar is 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 by Ar 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 ５ may 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, in combination with one or more groups. The non-fused carbazol-9-yl group referred to 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 represented by the formula (I) may be unsubstituted or substituted with a combination 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 some of them may be substituted. Examples of embodiments in which only some of the 10 hydrogen atoms are substituted include embodiments in which 1 to 5 are substituted, embodiments in which 3 are substituted, embodiments in which 2 are substituted, and embodiments in which 1 is substituted. Examples of embodiments in which only the 3-position is substituted include embodiments in which the 3- and 6-positions are substituted, embodiments in which the 1- and 8-positions are substituted, and embodiments in which the 2- and 7-positions are substituted. The non-fused carbazol-9-yl group may be substituted only with deuterium atoms, may be substituted only with unsubstituted alkyl groups, may be substituted partially or completely with deuterated alkyl groups, may be substituted only with unsubstituted aryl groups, or may be substituted partially or completely with deuterated aryl groups. 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 ５ The non-fused carbazol-9-yl group represented by the formula (I) is a carbazol-9-yl group in which at least one hydrogen atom is deuterated, and 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 optionally substituted with one or two groups selected from the group consisting of a deuterium atom and an alkyl group at at least one of the 3- and 6-positions. In another embodiment of the present invention, the carbazol-9-yl group is an alkyl group optionally substituted with a deuterium atom at at least one of the 3- and 6-positions.

[0016] In the following, R in general formula (1) １ ~R ５Specific examples of the non-fused carbazol-9-yl group that can be used are shown below. However, the non-fused carbazol-9-yl group that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, Ph represents a phenyl group (C ６ H ５ ) and * indicates the bond position. Methyl groups are omitted, so for example, D2 has one methyl group. However, deuterated methyl groups are ３ Also, C ６ D ５ represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.

[0017] The compounds D26 to D50 are those in which all hydrogen atoms present in the above D1 to D25 have been replaced with deuterium atoms.

[0018] In one aspect of the present 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 R may take is selected from the group consisting of D14 to D50. １ ~R ５ The 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 D32, and D39 to D44. １ ~R ５ The non-fused carbazol-9-yl group that can be taken by 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 optionally 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 ５Preferably, two to four of R are the non-fused carbazol-9-yl groups. １ ~R ５ In a preferred embodiment of the present invention, two or three of R １ is not the non-fused carbazol-9-yl group. ２ ~R ５ In one embodiment of the present invention, two or three of R ２ or R ３ is the non-fused carbazol-9-yl group. ４ is the non-fused carbazol-9-yl group. ５ is the non-fused carbazol-9-yl group. ５ is the only non-fused carbazol-9-yl group. ３ and R ５ is the only non-fused carbazol-9-yl group. ２ and R ５ is the only non-fused carbazol-9-yl group. ２ and R ４ is the only non-fused carbazol-9-yl group. ３ and R ４ and R ５ is the only non-fused carbazol-9-yl group. ２ and R ４ and R ５ is the non-fused carbazol-9-yl group. １ ~R ５ When two or more of R are the non-fused carbazol-9-yl groups, they may be the same or different. 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 １is a hydrogen atom or a deuterium atom. １ ~R ５ R １ ~R ５ The number of substituted or unsubstituted aryl groups among R is 0 or 1, and preferably 1. １ ~R ５ The number of substituted or unsubstituted alkyl groups among R is 0 to 3, preferably 0 to 2, and may be 1 or 0. 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 general formula (1), X １ ~X ３ One to three of these are N, and the rest are C(R ６ ) represents. ６ represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or 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 is C(R ６ In a preferred embodiment of the present invention, X １ and X３ is N and X ２ is C(R ６ In one aspect of the present invention, X １ is N and X ２ and X ３ is C(R ６ In one aspect of the present invention, X ３ is N and X １ and X ２ is C(R ６ In one aspect of the present invention, R ６ is a hydrogen atom or a deuterium atom. ６ is an alkyl group optionally substituted with a deuterium atom. 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 present 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 ２ are each independently an at least partially deuterated aryl group. １ and X ２ is N and X ３ is 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 is 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. １ and X ３ is N and X ２ is 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 is 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 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).

[0023] In the general formula (2), X ４ ~X ６ One to three of these are N, and the rest are C(R ７ ) represents. 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 aspect of the present invention, L １ is a substituted or unsubstituted arylene group. １ is a substituted or unsubstituted heteroarylene group. The aryl moiety constituting the arylene group is １ ~R ５The description of the aryl group and the preferred range thereof can be referred to in the section on the heteroarylene group. Examples of the heteroarylene group include a linking group in which at least one of the ring skeleton carbon atoms constituting the arylene group is substituted with a nitrogen atom. １ However, the L that can be used in the present invention is １ is not to be construed as being limited by these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0025]

[0026] All hydrogen atoms in L2 to L13 are replaced with deuterium atoms, and L14 to L25 are disclosed. １ is selected from the group consisting of L1 to L25. １ is selected from the group consisting of L1 to L7, 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 these are N, and the rest are C(R ７ ) represents. ７ represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or 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 is C(R ７ In one aspect of the present invention, X ４ and X ６ is N and X５ is C(R ７ In one aspect of the present invention, X ４ is N and X ５ and X ６ is C(R ７ In one aspect of the present invention, X ６ is N and X ４ and X ５ is C(R ７ In one aspect of the present invention, R ７ is a hydrogen atom or a deuterium atom. ７ is an alkyl group optionally substituted with a deuterium atom. ７ is 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 in general formula (1) are １ and Ar ２ In one aspect 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 aspect 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, more preferably an unsubstituted phenylene group (e.g., L2, e.g., L6). In a preferred embodiment of the present invention, X ４ and X ５ is N and X ６is C(R ７ ) and R ７ is a hydrogen atom or a deuterium atom, and L １ In one aspect of the present invention, X ４ and X ５ is N and X ６ is 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, more preferably an unsubstituted phenylene group (e.g., L2, e.g., L6). In one embodiment of the present invention, X ４ and X ６ is N and X ５ is C(R ７ ) and R ７ is a hydrogen atom or a deuterium atom, and L １ In one aspect of the present invention, X ４ and X ６ is N and X ５ is 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 present 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. ４ and X ５ is N and X ６ is 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 In one aspect of the present invention, X ４ and X ５ is N and X ６ is 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. ４ and X ６ is N and X ５ is 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 is 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 In a preferred embodiment of the present invention, X １ ~X ３ Two of them are N and X ４ ~X ６Two of them are N. For example, X １ , X ２ , X ４ , X ５ Only N is used. For example, X １ , X ３ , X ４ , X ６ In one aspect of the invention, only X １ ~X ３ One of the two is N, and X ４ ~X ６ Two of them are N. For example, X １ , X ４ , X ５ Only N is used. For example, X １ , X ４ , X ６ Only N is used. For example, X ３ , X ４ , X ５ Only N is used. For example, X ３ , X ４ , X ６ In one aspect of the invention, only X １ ~X ３ One of the two is N, and X ４ ~X ６ One of the is N. For example, X １ and X ４ Only N is used. For example, X ３ and X ６ Only N is.

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

[0033] The compound represented by general formula (1) preferably does not contain metal atoms, and may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and sulfur atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, and nitrogen atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound containing no hydrogen atoms but containing 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 groups, selected from the group consisting of heteroarylthio groups (e.g., having 5 to 30 atoms constituting the ring skeleton), 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. As used herein, "substituent group B" 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 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 atoms), a heteroaryloxy group (e.g., having 5 to 30 ring atoms), and a diarylamino group (e.g., having 0 to 20 carbon atoms). As used herein, "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 atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). As used herein, the term "substituent group D" refers to one atom or group, or a combination of two or more groups, 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, "substituent group E" 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), and an aryl group (e.g., having 6 to 22 carbon atoms). In the present specification, when "substituted or unsubstituted" or "optionally substituted" is described, the substituent may be selected, for example, from substituent group A, from substituent group B, from substituent group C, from substituent group D, or from substituent group E.

[0035] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 12 below. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, R ３ ~R ５ The structure of each compound is individually shown by specifying each compound. ２ is a group represented by general formula (2), and 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.

[0036] In Table 2, each row contains R ３ ~R ５ The structures of compounds 1 to 250 are shown by collectively displaying R ３ ~R ５ In the case of the columns of compounds 51 to 100 in Table 2, R ４ is fixed to Ar1 (phenyl group), and R３ and R ５ In the same manner, in the case of the columns of compounds 101 to 150 in Table 2, R ４ is fixed to 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, grouped together and displayed in five rows.

[0037]

[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]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048] In Tables 1 to 11, Ar in general formula (1) 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 ４The compounds in which the Ar of compounds 1 to 2500 have been changed as shown in Table 12 are listed in order in a table format. In Table 12, in order to make the correspondence easier to understand, compounds 1 to 2500 are also listed in the first row. In the second row of Table 12, the Ar of compounds 1 to 2500 are listed in order in a table format. ２ and Ar ４ The compounds in which both are Ar1 are designated as compounds 1(1) to 2500(1) in order. For example, compound 1(1) is the compound 1 in which Ar ２ and Ar ４ In addition, compound 2(1) is a compound having a structure in which Ar is substituted with Ar in compound 2. ２ and Ar ４ Compound 2500(1) shows a compound having a structure in which Ar is substituted with Ar. 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 designated as Compounds 1(2) to 2500(2) in this order. １ and Ar ３ , Ar ２ and Ar ４ The compounds listed in Table 12 are identified in order. Among the compounds identified in Table 12, R of compounds 1(m) to 2500(m) (m is an integer of 1 to 138) １ , R ６ , R ７ is a hydrogen atom, and L １ is a single bond (L1).

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

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

[0051] 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, for example, 1300 or less, when it is intended to use an organic layer containing the compound represented by general formula (1) as a film formed by a vapor deposition method. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using a coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also easy to purify to increase its purity.

[0052] By applying the present invention, it is also conceivable to use a compound containing multiple structures represented by general formula (1) in its molecule as a light-emitting material. For example, it is conceivable to use a polymer obtained by pre-preparing a polymerizable group in the structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any site of general formula (1) and polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material. Alternatively, it is conceivable to couple compounds having a structure represented by general formula (1) together to obtain a dimer or trimer, and use these as a light-emitting material.

[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.

[0054] In the above general formula, Q represents a group containing a structure represented by general formula (1), L １ and L ２represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１ Preferably, X has a structure represented by the formula: １１ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. １０１ , R １０２ , R １０３ and R １０４ each independently represents a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L １ and L ２ The linking group represented by the following formula (1) can be bonded to any site of Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

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

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

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

[0058] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, time-dependent density functional theory using a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional can be used to analyze the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) and screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, donor moieties ("D") can be selected if they have a HOMO energy (e.g., ionization potential) above -6.5 eV, for example. Acceptor moieties ("A") can be selected if they have a LUMO energy (e.g., electron affinity) below -0.5 eV, for example. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly constrain the acceptor and donor moieties into specific configurations. In certain embodiments, compound libraries are screened using one or more of the following properties: 1. Emission near a specific wavelength; 2. Calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ＳＴ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ＳＴ The quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

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

[0060] [Light-emitting material having a boron atom] 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). As the light-emitting material having a boron atom, a wide variety of boron compounds that can emit light when used in combination with the compound represented by general formula (1) can be used. However, boron complexes are not used in the present invention. In the present invention, it is preferable to use a light-emitting material that utilizes the multiple resonance effect of boron atoms and nitrogen atoms. Examples of such light-emitting materials include compounds having a structure in which boron atoms and nitrogen atoms are introduced into the skeleton of a polycyclic aromatic compound. It is preferable that the boron atom and the nitrogen atom have a structure in which they are connected 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.

[0062] In 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 as a single bond to form a pyrrole ring. １ is a boron atom, and X ２ is a nitrogen atom. In this case, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. 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 R５ , 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. ３ and R ６ are both substituents. In a preferred embodiment of the present invention, R ８ , R １０ and R １２ are all substituents. 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 ９and 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 pairs of are not bonded to each other to form a cyclic 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 the present specification.

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

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

[0065] In 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 are each preferably independently 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 １０are 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 １０ are each independently a deuterium atom or an alkyl group optionally substituted with a deuterium atom. In one embodiment of the present invention, no further rings are fused 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 atoms 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]

[0068] In 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 to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R１５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of C-R is O or NR, and the remaining may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0069]

[0070] In 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 ９ and R ２ , R ２ and R１０ , 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]

[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 , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R １ and R２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ at least one of the rings formed by bonding together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２ At least one of the C-R 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]

[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 ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0075]

[0076] In the general formula (9), X ３ represents an oxygen atom or a sulfur atom, 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 R ７ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0077]

[0078] In the general formula (10), X ４ represents an oxygen atom or a sulfur atom, 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 cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0079]

[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 ３represents 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]

[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 １７ 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 , 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]

[0084] In the general formula (13), Z１ 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 independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ５ , Z ５ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0085]

[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 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]

[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 ２ represents 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 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]

[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; Z２ 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 cyclic structure. ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ At least one pair of these is bonded to each other to form a ring structure.)

[0091]

[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]

[0094] In the general formula (18), Z １ 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]

[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; R１ and R ６１ ~R ６６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , Z ９ and R ６１ , R ６１ and R ６２ , R ６２ and R ６３ , 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]

[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 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]

[0100] In the general formula (21), Z １ , Z １１ and Z１２ 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 ７２ ~R ７４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７１ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７１ and Z １１ , Z １１ and R ７２ , R ７２ and R ７３ , R ７３ and Z ７４ , R ７４ and Z １２ may be bonded to each other to form a cyclic structure.

[0101]

[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 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７５ and Z １１ , Z １１ and R ７６ , R ７６ and R ７７ , R ７７ and R ７８ , R ７８ and R ７９ , R ７９ and R ８０ , R８０ and R ８１ , R ８１ and R ８２ may be bonded to each other to form a cyclic structure.

[0103]

[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 １２０ and R １２１ , R １２１ and R １２２ , R １２２ and R １２３ , R １２３ and R １２４ , R １２４ and R１２５ , 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]

[0106] In 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 , Z ２ 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 １may 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 from the range of 0.01 to 50 wt %, 0.1 to 30 wt %, or 0.5 to 10 wt % of the content of the compound represented by general formula (1). The organic light-emitting device of the present invention may use two or more compounds represented by general formula (1) or two or more compounds having a boron atom.

[0108] [Host Material] In the organic light-emitting device of the present invention, the layer (light-emitting layer) containing the compound represented by 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 may be 99% by weight or less, 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 an increase in the wavelength of emitted light. 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 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:

[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):

[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 aspect of the invention, X １１ is N(R Ａ In one aspect of the present invention, X １１ is O. In one aspect 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. １１ is N (R Ａ ), then L is (R １１５ ) n is bonded to a benzene ring, or X １１ The bond extending from L to the right is, as explained herein, (R １１５ ) n is bonded to the benzene ring to which it is bonded, 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. １１ and A１２ 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 In one embodiment of the present invention, at least one of A is a furan ring. １１ and A １２ In one embodiment of the present invention, at least one of A is a thiol ring. １１ and A １２ In one embodiment of the present invention, at least one of A is a pyrrole ring. １１ and A １２ At least one of the rings is a cyclopentadiene ring. The benzene ring, furan ring, thiol ring, pyrrole ring, and cyclopentadiene ring referred to herein may be fused with another ring. The fused ring may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or may be a ring in which two or more of these rings are fused. An aromatic hydrocarbon ring, an aromatic heterocycle, or a ring in which two or more of these rings are fused is preferred. An example of an aromatic hydrocarbon ring is a benzene ring. The aromatic heterocycle refers to a ring that exhibits aromaticity and contains heteroatoms as ring skeleton-constituting atoms. It is preferably a 5- to 7-membered ring, and for example, a 5- or 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the aromatic heterocycle. 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- or 6-membered ring can be employed. For example, a cyclopentadiene ring can be employed. The aliphatic heterocycle means a ring containing a heteroatom as a ring skeleton-constituting atom and not exhibiting 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. １１ is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are fused.１１ is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are fused. １１ is a benzene ring, and a furan ring of benzofuran or a 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. １２ is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, a pyrrole ring, or a ring in which two or more of these are fused. １２ is a benzene ring, and the benzene ring is further fused with a benzene ring, a furan ring, a thiol ring, or a ring in which two or more of these are fused. １２ is a benzene ring, and a furan ring of benzofuran or a 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. １１ Or A １２ The hydrogen atoms of the rings constituting the formula (I) may be substituted with deuterium atoms or substituents. The substituents can be selected from any of the groups A to E, for example, from the 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 １２At least one ring constituting A is substituted with a deuterium atom, an alkyl group, an aryl group, or a group combining these. １１ Or A １２ When a pyrrole ring is included as a ring constituting the formula (I), it is preferred 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 １２ When two or more hydrogen atoms of the ring constituting the formula (I) are substituted, they may be substituted with the same atom or group, or with different atoms or groups.

[0113] In 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). Ａrepresents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a bond to L (i.e., a single bond to L). For the aryl group, heteroaryl group, and alkyl group, please refer to the explanations of "aryl group," "heteroaryl group," and "alkyl group" above. The aryl group preferably has 6 to 14 carbon atoms, 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- 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 alkyl group preferably has 1 to 6 carbon atoms, 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 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. １１２ is 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. 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. １１ and A １２ In one embodiment of the present invention, the description of the ring further fused to the benzene ring in the description of R １１１ and R１１２ , R １１２ and R １１３ , R １１３ and R １１４ are bonded to each other 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- and 6-positions is substituted with a deuterium atom, an alkyl group, an aryl group, or a combination thereof. Alternatively, it may 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) can 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] Specific examples of groups that can be used as the group bonded to the left of L in general formula (25) are listed below. However, the groups that can be used in the present invention should not be construed as being limited by these specific examples. Note that in the following specific examples, methyl groups are omitted. For this reason, for example, Z2 and Z3 are substituted with methyl groups. * indicates the bonding position to L.

[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 have been substituted 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. In addition, the phenyl groups (C ６ H ５ ) to deuterated C ６ D ５ Groups substituted with Z4(p) to Z6(p), Z19(p) to Z86(p), and Z111(p) to Z178(p) are exemplified herein 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 of Z1 to Z196 are deuterated are exemplified herein as Z1(D) to Z196(D), respectively.

[0117] In general formula (25), specific examples of the group 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 should not be construed as being limited by these specific examples. Note that in the following specific examples, methyl groups are omitted. * indicates the bonding position to L.

[0118] In addition to the above specific examples, methyl groups (CH ３ ) to deuterated CD ３ The groups substituted with X are exemplified here as X31(m) to X33(m) and X64(m) to X79(m), respectively. ６ H ５ ) to deuterated C ６ D ５ Examples of groups substituted with X are X5(p) to X21(p), X38(p) to X54(p), and X68(p) to X70(p), respectively. Furthermore, examples of groups in which all hydrogen atoms of X1 to X79 are deuterated are 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 is N (R Ａ ) and L is (R １１５ ) n is 3 when bonded to the benzene ring to which it is bonded, and X １１ is N (R Ａ ) and L is X １１ When the group is bonded to N represented by n, n is 4. １１５ may be the same or different from each other.

[0120] In general formula (25), L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a linking group formed by bonding two or more of these. For the aryl structure of an arylene group and the heteroaryl structure of a heteroarylene group, the explanations of "aryl group" and "heteroaryl group" above can be referred to. The arylene group and heteroarylene group may be substituted. If 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 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. 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 listed below. However, the L that can be employed in the present invention should not be construed as being limited by these specific examples. In the following specific examples, methyl groups are omitted. For example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0121]

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

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

[0124]

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

[0126] When it is intended to use an organic layer containing the compound represented by general formula (25) by forming it into a film by vapor deposition, for example, the molecular weight of the compound represented by general formula (25) 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 general formula (25) preferably has a smaller dipole moment, since this increases the orientation when the film is formed. 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 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 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 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 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 Device] The organic light-emitting device of the present invention comprises a compound represented by general formula (1) and a light-emitting material having a boron atom (excluding boron complexes). The layer (light-emitting layer) comprising the compound represented by general formula (1) and the light-emitting material having a boron atom may further comprise a host material. In this case, the compound represented by general formula (1) functions as an assist dopant. The light-emitting layer of the organic light-emitting device of the present invention may also contain a delayed fluorescent material other than the compound represented by general formula (1). Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, light-emitting materials capable of emitting delayed fluorescence are employed, as described in WO 2015 / 136880, WO 2015 / 137244, WO 2015 / 137202, WO 2015 / 137136, WO 2015 / 146541, and WO 2015 / 159541. The above publications described in this paragraph are incorporated herein by reference. The organic light-emitting device of the present invention may contain light emitted 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 aspect of the present invention, 90% or more of the light emitted from the organic light-emitting device is emitted from the light-emitting material having boron atoms, for example, 99% or more, for example, 99.9% or more is emitted from the light-emitting material having boron atoms. In some embodiments, the light-emitting layer does not contain any metal element (in the present invention, boron atoms are not included in the metal elements). In some embodiments, the light-emitting layer can be composed of a material consisting only of 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 may be composed of a material consisting only of 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 may be composed of a material containing all of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, boron atoms, and oxygen atoms, but not any other elements. In the organic light-emitting device of the present invention, the compound represented by general formula (1) may be used in a layer other than the light-emitting layer. For example, the compound represented by general formula (1) may be used in a layer adjacent to the light-emitting layer.

[0130] Film-forming techniques can be used to form layers of organic light-emitting devices. In some embodiments, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited thereto. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or a single deposition source containing a mixture of the compounds may be co-deposited. When a single vapor deposition source is used, a mixed powder of compound powders may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating, melting, and cooling each compound may be used. In some embodiments, co-deposition is performed under conditions where the deposition rates (weight loss rates) of the multiple compounds contained in a single vapor deposition source are identical or nearly identical, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the vapor deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed as a vapor deposition source, a film having a desired composition ratio can be easily formed. In some embodiments, the temperature at which each compound to be co-deposited has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[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 has its lowest excited singlet energy level, and is located between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic photoluminescence device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least an light-emitting layer. In one embodiment, the organic layer includes only an light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

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

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

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

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

[0136] Injection Layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials:

[0137]

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

[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 blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functions of an electron blocking layer and an exciton blocking layer.

[0140] Hole Blocking Layer: The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer may be the same materials as those described above for the electron transporting layer. Examples of preferred compounds that can be used for the hole blocking layer are listed below.

[0141]

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

[0143]

[0144] Exciton Blocking Layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

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

[0146]

[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, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0148]

[0149] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0150]

[0151] Although specific examples of preferred materials that can be used in organic electroluminescence devices have been given, the materials that can be used in the present invention should not be construed as being limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be diverted to be used as materials having other functions.

[0152] Devices: In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0153] Bulb or Lamp: In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

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

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

[0156] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

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

[0158] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

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

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

[0161] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

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

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

[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), charged with the solution, and purified by column chromatography (toluene:hexane = 1:1). Further recrystallization from toluene afforded yellow compound T1 (14.8 g, 13.7 mmol, 84% yield). 1 H-NMR (400 MHz, CDCl): 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: Fabrication and evaluation of organic electroluminescence device Each thin film was deposited by vacuum deposition on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed, at a vacuum degree of 5.0×10 －５The layers were laminated at 100 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 40 nm thick layer, which served 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 30 nm thick layer. 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 vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing an organic electroluminescence element, Element 1. Comparative Element 1 was produced in the same manner using Comparative Compound T instead of T1. Each of the produced elements was subjected to a current drain of 6.3 mA / cm. ２ The external quantum efficiency (EQE) was measured by driving the device at 1000 Hz. 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 J. Appl. Phys. Lett., 2005, pp. 7, 8405. The results are shown in the table below. 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 properties.

[0166] Example 2 Preparation of Organic Electroluminescent Device An organic electroluminescent device, Device 2, is prepared according to the same procedure as in Example 1, except that D2 is used instead of D1.

[0167] Example 3 Preparation of Organic Electroluminescent Device An organic electroluminescent device, Device 3, is prepared according to the same procedure as in Example 1, except that D3 is used instead of D1.

[0168]

[0169] By using the compound represented by general formula (1) in combination with a boron compound, it is possible to provide a light-emitting device having good orientation in the light-emitting layer and excellent light-emitting properties. Therefore, the present invention has high industrial applicability.

Claims

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). [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 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 the groups is N, and the rest are C(R ６ ) represents 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. In the general formula (2), X ４ ~X ６ At least one of the groups is N, and the rest are C(R ７ ) represents 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 The organic light-emitting element according to claim 1 , wherein 3. R ３ The organic light-emitting element according to claim 1 , wherein 4. R １ ~R ５ The organic light-emitting device according to claim 1, wherein two or more of the following are the non-fused carbazol-9-yl groups:

5. R １ ~R ５ The organic light-emitting device according to claim 1, 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 claim 1 , wherein two or more of 7. X ４ ~X ６ The organic light-emitting device according to claim 1 , wherein two or more of 8. L １ The organic light-emitting device according to claim 1 , wherein is a single bond.

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

10. The organic light-emitting element according to claim 1, which has 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 a boron atom is a compound represented by the following general formula (3): [In the general formula (3), X １ and X ２ is a nitrogen atom and the other is a boron atom. 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 , R１４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other to form a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring.

12. R in general formula (3) ３ and R ６ The organic light-emitting device 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 each of the groups is a substituent.

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

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 ６and 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 of claim 11 , wherein none of the pairs are bonded to each other to form a ring structure.

16. The organic light-emitting device according to any one of claims 1 to 10, wherein the light-emitting material having a boron atom is a compound having the following skeleton:

Images