Compounds, light-emitting materials and organic light-emitting devices

Abstract

The compound represented by the general formula has excellent light-emitting characteristics and emits light having a short wavelength. Y1 is N-RA; Y2 is O, S, C=O or N-RA; RA is an aryl group, etc.; R1-R11 are hydrogen atoms or substituents; and at least one of R1-R3 is a carbazolyl group substituted by an aryl group, etc.

Description

[Technical Field]

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

[0002] There has been much research into improving the luminous efficiency of organic light-emitting devices such as organic light-emitting diodes (OLEDs). For example, Non-Patent Document 1 describes that the use of boron compounds having a structure such as 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phenazaborine (DABNA-1) results in thermally activated delayed fluorescence due to a reverse intersystem crossing process, resulting in emission of a narrow half-width and high color purity. Such emission can achieve high luminous efficiency, making it useful for display-oriented applications. Furthermore, Non-Patent Documents 1 and 2 describe that modifying DABNA-1 adjusts the energy levels of the highest accessible molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), and also promotes the fluorescence emission process and reverse intersystem crossing process that contribute to light emission, thereby improving the electroluminescence quantum efficiency. These documents report that the luminescence quantum yield could be improved by introducing substituents into DABNA-1, but the resulting light emission has a longer wavelength than DABNA-1. [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] Adv. Mater. 2016, 28, 2777-2781 [Non-patent document 2] Angew. Chem. Int. Ed. 2018, 57, 11316-11320 Summary of the Invention [Problem to be solved by the invention]

[0004] As described in Non-Patent Documents 1 and 2, molecular modification of compounds that exhibit multiple resonance effects, such as DABNA-1, is a useful method for improving various physical properties required for luminescent materials in organic light-emitting devices. However, such modifications broaden the conjugated system, which leads to a shift in the emission wavelength. This has led to the problem of being unable to provide the desired luminescent materials in the blue region, which are in need of development. In view of the problems with the conventional technology, the present inventors have conducted extensive research with the aim of providing derivatives that emit light at shorter wavelengths than compounds that exhibit the multiple resonance effect, or derivatives that exhibit superior luminescence properties to compounds that exhibit the multiple resonance effect. [Means for solving the problem]

[0005] As a result of extensive research, the present inventors have unexpectedly found that by introducing specific substituents into specific positions of a compound that exhibits a multiple resonance effect, it is possible to obtain derivatives that emit light at short wavelengths or derivatives with improved light-emitting properties. The present invention has been proposed based on this finding and has the following configuration. [1] A compound represented by the following general formula (1): [ka] [In general formula (1), Y 1 is NR A Represents. Y 2 is O, S, C=O or NR A Represents. R A each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 ~R 11 each independently represents a hydrogen atom or a substituent, R 1 and R 2 , R2 and R 3 , 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 A and R 4 , R A and R 11 may be bonded to each other to form a cyclic structure. 1 , R 2 and R 3 At least one of the groups is a group represented by the following general formula (2). [ka] R 21 ~R 28 each independently represents a hydrogen atom or a substituent, R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , R 27 and R 28 may be bonded to each other to form a cyclic structure. 21 ~R 28 At least one of is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. * indicates the bonding position.] [2] Y 2 NR A The compound according to [1], [3] R 7 and R 8 and [3] are both hydrogen atoms. [4] R AThe compound according to any one of [1] to [3], wherein each independently represents a substituted or unsubstituted aryl group. [5] R 1 ~R 11 The compound according to any one of [1] to [4], wherein each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. [6] R 5 and R 10 The compound according to any one of [1] to [5], wherein each of the groups independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group. [7] R 6 and R 9 The compound according to any one of [1] to [6], wherein each of the groups independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group. [8] R 2 The compound according to any one of [1] to [7], wherein is a group represented by general formula (2): [9] R in general formula (2) 21 ~R 28 The compound according to any one of [1] to [8], wherein each independently represents a hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[10] R in general formula (2) 23 and R 26 The compound according to [9], wherein at least one of is a substituted or unsubstituted aryl group.

[11] R in general formula (2) 23 and R 26 and each independently represents a substituted or unsubstituted aryl group.

[12] The compound according to [1], having any one of the following structures: [ka]

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

[12] .

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

[12] .

[15] The organic light-emitting device of

[14] , wherein the device has a layer containing the compound, the layer also containing a host material.

[16] The organic light-emitting device according to

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

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

[14] to

[16] , wherein the compound emits the greatest amount of light among the materials contained in the device.

[18] The organic light-emitting device according to

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

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

[14] to

[18] , which is an organic light-emitting diode (OLED).

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

[14] to

[19] , which emits delayed fluorescence.

[21] A compound represented by the following general formula (A): [ka] [In the general formula (A), X 1 represents a halogen atom. Y 1 is NR A Represents. Y 2 is O, S, C=O or NR A Represents. R A each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 ~R 11 each independently represents a hydrogen atom or a substituent, R 1 and R 2 , R 2 and R 3 , 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 A and R 4 , R A and R 11 may be bonded to each other to form a cyclic structure. 1 , R 2 and R 3 At least one of the groups is a group represented by the following general formula (2). [ka] R 21 ~R 28 each independently represents a hydrogen atom or a substituent, R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , R 27 and R 28 may be bonded to each other to form a cyclic structure. 21 ~R 28 At least one of is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. * indicates the bonding position.] [Effects of the Invention]

[0006] According to the present invention, it is possible to provide a compound that emits light at a short wavelength while exhibiting a multiple resonance effect, a compound that has good light-emitting properties, and an organic light-emitting device that exhibits excellent light-emitting properties and emits light at a short wavelength. [Brief explanation of the drawings]

[0007] [Figure 1] FIG. 2 is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescence element. [Figure 2] 1 is a graph showing the results of thermogravimetric differential thermal analysis of Compound 1. DETAILED DESCRIPTION OF THE INVENTION

[0008] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits.

[0009] [Compound represented by general formula (1)] The present invention provides a compound represented by the following general formula (1): [ka]

[0010] In general formula (1), Y 1 is NR A represents Y 2 is O, S, C=O or NR A Y 2 NR A When expressing Y 1 and Y 2 may be the same or different, but are preferably the same. R in general formula (1) 7 and R 8 may be bonded to each other to form a ring structure. 7 and R 8 are combined together to form -Y 3 -, and form a linking group represented by Y 3 is O, S, C=O or NR A In one aspect of the present invention, Y 3 As NR A In another aspect of the present invention, Y 3 In another embodiment of the present invention, Y 3 C=O can be selected as

[0011] In one aspect of the present invention, Y 1 and Y 2 are each independently NR A and R 7 and R 8 is a hydrogen atom. In this case, Y 1 and Y 2 In another aspect of the present invention, Y 2 is O and R 7 and R 8 is a hydrogen atom. In another aspect of the present invention, Y 2 is S and R 7 and R 8 is a hydrogen atom. In another aspect of the present invention, Y 2 is C=O and R 7 and R 8 is a hydrogen atom. In another aspect of the present invention, R 7 and R 8 are combined together to form -Y 3 -, and Y 1 ~Y 3 are each independently NR A In this case, Y 1 ~Y 3 An example can be given in which two of the above are the same and one is different. 1 ~Y 3 In another embodiment of the present invention, Y 1 and Y 2 are each independently NR A and Y 3 is O. In this case, Y 1 and Y 2 In another aspect of the present invention, Y 1 and Y 2 are each independently NR A and Y 3 is S. In this case, Y 1 and Y 2 In another aspect of the present invention, Y 1 and Y 2 are each independently NRA and Y 3 is C=O. In this case, Y 1 and Y 2 In another aspect of the present invention, Y 1 and Y 3 are each independently NR A and Y 2 is O. In this case, Y 1 and Y 3 In another aspect of the present invention, Y 1 and Y 3 are each independently NR A and Y 2 is S. In this case, Y 1 and Y 3 In another aspect of the present invention, Y 1 and Y 3 are each independently NR A and Y 2 is C=O. In this case, Y 1 and Y 3 are preferably the same.

[0012] NR A R A Each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Aare each independently a substituted or unsubstituted aryl group. Examples of the substituents of the aryl and heteroaryl groups mentioned here include substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted heteroaryloxy groups. Preferred are substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups, and more preferred are substituted or unsubstituted alkyl groups and substituted or unsubstituted aryl groups. For example, a substituted or unsubstituted alkyl group can be preferably selected. Examples of the substituents of the alkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, and heteroaryloxy group include alkyl groups, aryl groups, heteroaryl groups, alkoxy groups, aryloxy groups, and heteroaryloxy groups. R A When two or more substituents are present in each of the aryl group and heteroaryl group represented by R, these substituents may be bonded to each other to form a cyclic structure. In this case, the cyclic structure may be an aromatic ring or a non-aromatic ring. It may also be a hydrocarbon ring or a heterocyclic ring. For example, a benzene ring can be mentioned. A When two or more substituents are present in each of the aryl group and heteroaryl group represented by R, these substituents may not be bonded to each other. A The substituents present in the aryl group and heteroaryl group represented by R in general formula (1) 1 ~R 11 In another embodiment of the present invention, R A The substituents present in the aryl group and heteroaryl group represented by R in general formula (1) 4 and R 11 In yet another embodiment of the present invention, Y 1 is NR A and the R AThe substituents present in the aryl group and heteroaryl group represented by R 11 and bond to each other to form a ring structure (preferably R 11 is a single bond and R A and Y is bonded to an aryl or heteroaryl ring of 2 is NR A and the R A The substituents present in the aryl group and heteroaryl group represented by R 4 and bond to each other to form a ring structure (preferably R 11 is a single bond and R A attached to an aryl or heteroaryl ring of Below is NR A Specific examples of NR that can be used in the present invention are given below. A The symbols * represent bonding positions. [ka]

[0013] R in general formula (1) 1 ~R 11 each independently represents a hydrogen atom or a substituent. Among them, R 1 , R 2 and R 3 At least one of them is a group represented by the following general formula (2). The compound represented by general formula (1) includes a compound whose emission wavelength is shortened by bonding with a group represented by general formula (2). By substituting a hydrogen atom with a group represented by general formula (2), the emission wavelength is shortened preferably by 5 nm or more, more preferably by 10 nm or more, and even more preferably by 15 nm or more (see Example 1 and Comparative Example 1 described later for measurement conditions). Furthermore, the maximum emission wavelength of the compound represented by general formula (1) is preferably 460 nm or less, more preferably 455 nm or less, and even more preferably 450 nm or less. The compound represented by general formula (1) includes a compound whose luminous efficiency is improved by the addition of a group represented by general formula (2). For example, the photoluminescence quantum efficiency (PLQY) measured by irradiating a thin film doped with PYD2Cz at a concentration of 1 wt% with 300 nm excitation light is preferably improved by 2% or more, more preferably by 3% or more, and even more preferably by 3.5% or more by the addition of a group represented by general formula (2). The measurement conditions for the luminous efficiency can be seen, for example, in Example 1 and Comparative Example 1 described below. The compound represented by general formula (1) includes a compound whose full width at half maximum is reduced by the addition of a group represented by general formula (2). For example, the full width at half maximum of the visible region emission peak of the emission spectrum observed when a thin film doped with PYD2Cz at a concentration of 1 wt % is irradiated with 300 nm excitation light is preferably reduced by 3 nm or more, more preferably by 5 nm or more, and even more preferably by 7 nm or more, by the addition of a group represented by general formula (2). For the measurement conditions of the full width at half maximum, reference can be made to, for example, the measurement conditions of Example 1 and Comparative Example 1 described later. The compound represented by general formula (1) is R 1 , R 2 and R 3 Only one of the groups may be a group represented by general formula (2), in which case R 2 is preferably a group represented by general formula (2). 1 may be a group represented by general formula (2), or R 3 may be a group represented by general formula (2). 1 , R 2 and R 3 When two or three of the groups are groups represented by general formula (2), the groups represented by the general formula (2) may be the same or different from each other. It is preferable that they are the same. When there are two groups, R 1 and R 2 or R 2 and R 3 or R 1and R 3 R which is not a group represented by general formula (2) may also be 1 ~R 3 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a hydrogen atom or a substituted or unsubstituted alkyl group. 1 ~R 3 It is also preferable that all of R are hydrogen atoms. The explanation and preferred ranges of the substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group mentioned here are as follows: A Reference can be made to the corresponding description in [ka]

[0014] In general formula (2), * represents the bonding position. 21 ~R 28 each independently represents a hydrogen atom or a substituent, R 21 ~R 28 At least one of is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and is preferably a substituted or unsubstituted aryl group. The explanation and preferred ranges of the substituted or unsubstituted aryl group and the substituted or unsubstituted heteroaryl group are given in R A Reference can be made to the corresponding description in R 21 ~R 28 Among these, the number of substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups is 1 to 8, preferably 1 to 6, and more preferably 1 to 4. For example, it may be 1. Also, it is preferable that it is 2. When there are 2 or more, they may be the same or different, but it is preferable that they are the same. R 21 ~R 28 Among them, R 22 , R23 , R 24 , R 25 , R 26 and R 27 It is preferable that at least one of R is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, 22 , R 23 , R 26 and R 27 It is more preferable that at least one of R is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, 23 and R 26 It is more preferable that at least one of R is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 23 and R 26 may both be substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups. R 21 ~R 28 Among these, it is preferable that the group other than a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is a hydrogen atom or a substituted or unsubstituted alkyl group. 21 ~R 28 Among these, those that are not substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups may all be hydrogen atoms. 1 to 4 may be substituted or unsubstituted alkyl groups, or 1 to 2 may be substituted or unsubstituted alkyl groups. An example of the substituent of the alkyl group mentioned here is an aryl group. It is also preferred that the alkyl group is unsubstituted.

[0015] R in general formula (1) 4 ~R 6 and R 9 ~R 11 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 4~R 6 and R 9 ~R 11 may be all hydrogen atoms. 4 ~R 6 and R 9 ~R 11 Three to five of R may be hydrogen atoms. 4 ~R 6 and R 9 ~R 11 In one embodiment of the present invention, 0 to 2 of R 5 and R 10 In one aspect of the present invention, at least one of R 6 and R 9 At least one of R is a substituent, and more preferably both are substituents. 5 and R 10 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R 4 , R 6 , R 9 and R 11 When R is a hydrogen atom, 6 and R 9 are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R 4 , R 5 , R 10 and R 11 is a hydrogen atom.

[0016] R in general formula (1) 1 and R 2 , R 2 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R11 , R A and R 4 , R A and R 11 may be bonded to each other to form a cyclic structure. 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , R 27 and R 28 may be bonded to each other to form a cyclic structure. However, it is also preferable that none of these combinations are bonded to each other to form a cyclic structure. When a cyclic structure is formed, the cyclic structure formed may be an aromatic ring or a non-aromatic ring. It may also be a hydrocarbon ring or a heterocyclic ring. For example, a benzene ring can be mentioned.

[0017] Below is R 1 ~R 11 Specific examples of the substituents are as follows. * indicates the bonding position. Among them, G2 to G5 are R 21 ~R 28 It is also a specific example of a substituted or unsubstituted aryl group of the formula: 1 ~R 11 and R 21 ~R 28 The present invention is not to be construed as being limited by these specific examples. [ka]

[0018] In a preferred group 1 of the present invention, R A are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and R 1 ~R 11are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R in general formula (2) 21 ~R 28 At least one of the groups is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. In a preferred group 2 of the present invention, R A are each independently a substituted or unsubstituted aryl group, R 1 ~R 11 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R in general formula (2) 21 ~R 28 At least one of the groups is a substituted or unsubstituted aryl group. In a preferred group 3 of the present invention, R A are each independently a substituted or unsubstituted aryl group, R 1 ~R 11 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and R in general formula (2) 21 ~R 28 At least one of the groups is a substituted or unsubstituted aryl group. In preferred groups 1 to 3, Y 2 NR A The groups in which the formula is as follows are designated as preferred groups 4 to 6, respectively. In preferred groups 1 to 3, Y 2 is O are preferred groups 7 to 9, respectively. In preferred groups 1 to 3, Y 2 is S, are designated as preferred groups 10 to 12, respectively. In preferred groups 1 to 3, Y 2 or C═O are preferred groups 13 to 15, respectively. In preferred groups 1 to 15, R 7 and R 8 is a hydrogen atom are preferred groups 16 to 30. In preferred groups 1 to 15, Y 3NR A The groups in which the formula is as follows are designated as preferred groups 31 to 45, respectively. In preferred groups 1 to 15, Y 3 is O are preferred groups 46 to 60, respectively. In preferred groups 1 to 15, Y 3 is S are designated as preferred groups 61 to 75. In preferred groups 1 to 15, Y 3 or C═O are designated as preferred groups 76 to 90, respectively. In preferred groups 1 to 90, R A is an unsubstituted aryl group are preferred groups 91 to 180. In preferred groups 1 to 90, R A is an aryl group substituted with a substituted or unsubstituted alkyl group are preferred groups 181 to 270, respectively. In preferred groups 1 to 90, R A is an aryl group substituted with a substituted or unsubstituted aryl group are preferred groups 271 to 360, respectively. In preferred groups 1 to 360, R 1 are groups represented by the general formula (2), are designated as preferred groups 361 to 720. In preferred groups 1 to 360, R 2 are groups represented by the general formula (2), are designated as preferred groups 721 to 1080. In preferred groups 1 to 360, R 3 are groups represented by the general formula (2), are designated as preferred groups 1081 to 1440, respectively. In preferred groups 1 to 1440, R 21 ~R 28 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group are preferred groups 1441 to 2880, respectively. In preferred groups 1 to 1440, R 21 ~R 28are each independently a hydrogen atom or a substituted or unsubstituted aryl group are preferred groups 2881 to 4320, respectively. In preferred groups 1 to 4320, R 4 ~R 11 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group are preferred groups 4320 to 8640, respectively. In preferred groups 1 to 4320, R 4 ~R 11 are each independently a hydrogen atom or a substituted or unsubstituted aryl group are preferred groups 8640 to 12960, respectively. In preferred groups 1 to 12960, R 1 and R 2 , R 2 and R 3 , 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 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , R 27 and R 28 However, groups that are not bonded to each other are preferred groups 12961 to 25920, respectively.

[0019] Among the compounds represented by general formula (1), for example, a compound represented by the following general formula (3) can be preferably used. [ka]

[0020] In general formula (3), Y 1 is NR A Y 2 is O, S, C=O or NR A Represents R A R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 5 , R 6 , R 9 and R 10 each independently represents a hydrogen atom or a substituent, R 5 and R 6 , R 9 and R 10 may be bonded to each other to form a cyclic structure. 23 and R 26 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Y in general formula (3) 1 , Y 2 , R 5 , R 6 , R 9 , R 10 , R 23 and R 26 For the explanation and preferred range of , please refer to the corresponding description in general formula (1). In one aspect of the present invention, R 5 and R 6 , R 9 and R 10 are not bonded to each other. In one aspect of the present invention, R 23 and R 26 are each independently a substituted or unsubstituted aryl group, preferably R 23 and R 26 are identical. In the present invention, R 5 , R 6 , R 9 and R 10 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 5 , R 6 , R 9 and R 10is a hydrogen atom. In another aspect of the present invention, R 5 and R 10 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 6 and R 9 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0021] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by vapor deposition, the molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less. 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. If a coating method is used, it is possible to form a film even from a compound with a relatively large molecular weight.

[0022] The present invention may be applied to prepare a compound containing a plurality of structures represented by general formula (1) in the molecule, and such a compound may be used, for example, as a charge transport material. For example, a polymerizable group may be present in the structure represented by general formula (1) in advance, and the polymerizable group may be polymerized to obtain a polymer. 1 ~R 11 and R 21 ~R 28 A polymer having a repeating unit can be obtained by preparing a monomer containing a polymerizable functional group in either one of the above and polymerizing it alone or copolymerizing it with other monomers. Alternatively, a dimer or trimer can be obtained by coupling compounds having a structure represented by general formula (1) together. Note that compounds not containing a repeating unit can also be preferably used in the present invention.

[0023] In one embodiment, the compound represented by general formula (1) does not contain a metal atom. In one embodiment, the compound represented by general formula (1) is composed only of hydrogen atoms, carbon atoms, boron atoms, and nitrogen atoms. In one embodiment, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, boron atoms, nitrogen atoms, and oxygen atoms. In one embodiment, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, boron atoms, nitrogen atoms, and sulfur atoms. In one embodiment, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of hydrogen atoms, carbon atoms, boron atoms, nitrogen atoms, oxygen atoms, sulfur atoms, and silicon atoms. In one embodiment, the compound represented by general formula (1) does not contain a cyano group. In one embodiment, the compound represented by general formula (1) does not contain a diarylamino group (provided that the two amino groups constituting the diarylamino group are not bonded to each other by a single bond or a linking group to form a cyclic structure).

[0024] Specific examples of compounds represented by general formula (3) are listed in the table below. The structures of compounds 1 to 3 in the table are also shown below. The scope of the compounds of the present invention should not be construed as being limited by these specific examples. [ka] [Table 1-1] [Table 1-2] [Table 1-3]

[0025] Other specific examples of the compound represented by general formula (1) are shown below. [ka]

[0026] [Method for synthesizing the compound represented by general formula (1)] The compound represented by general formula (1) can be synthesized by combining known reactions. For example, it can be synthesized via intermediate (A) according to the following reaction scheme. [ka]

[0027] In this reaction scheme, Y 1 , Y 2 , R 1 ~R 11 The definition of Y in the above general formula (1) 1 , Y 2 , R 1 ~R 11 This is the same as the definition of X. 1 and X 2 Each of X independently represents a halogen atom. Preferred examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. 1 and X 2 are preferably different halogen atoms, for example, X 1 Select the chlorine atom as X 2 For example, a bromine atom can be selected as the aryl group. In the above reaction scheme, R 1 , R 2 and R 3 The starting material is a trihalide of benzene substituted with HY. 2 substituted or unsubstituted benzene having a HY group; 1 By reacting this with a substituted or unsubstituted benzene having a methyl group, intermediate (A) is obtained. Furthermore, by adding t-BuLi to this intermediate (A) and cooling, adding tribromoboron, and then adding diisopropylamine and stirring, the target compound represented by general formula (1) can be obtained. For details of these reactions, please refer to the synthesis examples described below. The compound represented by general formula (1) can also be synthesized by combining other known synthesis reactions.

[0028] [Synthetic intermediates] The compounds represented by the following general formula (A), which are synthetic intermediates of the compounds represented by general formula (1), include novel compounds. [ka]

[0029] X 1 represents a halogen atom. Y 1 is NR A Represents. Y 2 is O, S, C=O or NR A Represents. R A each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 ~R 11 each independently represents a hydrogen atom or a substituent, R 1 and R 2 , R 2 and R 3 , 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 A and R 4 , R A and R 11 may be bonded to each other to form a cyclic structure. 1 , R 2 and R 3 At least one of the groups is a group represented by the following general formula (2). [ka]

[0030] R 21 ~R 28 each independently represents a hydrogen atom or a substituent, R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , R 27 and R 28 may be bonded to each other to form a cyclic structure. 21 ~R 28 At least one of is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. * indicates the bonding position. Y in general formula (A) 1 , Y 2 , R 1 ~R 11 The description and preferred range of Y in the general formula (1) above are as follows: 1 , Y 2 , R 1 ~R 11 Please refer to the description and preferred ranges of X. 1 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom, a chlorine atom, and a bromine atom being more preferred, and a chlorine atom being even more preferred.

[0031] Specific examples of the compound represented by formula (A) include compounds represented by the same Y 1 , Y 2 , R 1 ~R 11 X 1 is a chlorine atom. As representative examples, the structures of compounds A1 to A3 are shown below. Note that the scope of the compounds represented by general formula (A) should not be construed as being limited by these specific examples. [ka]

[0032] [Definition] Unless otherwise defined herein, scientific and technical terms used herein have the meanings commonly understood by those of ordinary skill in the art. Generally, the nomenclature and techniques for chemical compounds described herein are well known and commonly used in the art. The term "alkoxy" refers to an alkyl group having an oxygen atom attached thereto. In certain embodiments, an alkoxy has 1-20 carbon atoms. In certain embodiments, an alkoxy has 1-20 carbon atoms. Representative alkoxy groups include methoxy, trifluoromethoxy, ethoxy, propoxy, tert-butoxy, and the like. An "alkyl" group or "alkane" is a fully saturated, straight- or branched-chain non-aromatic hydrocarbon. Typically, a straight- or branched-chain alkyl group has from 1 to about 20 carbon atoms, preferably from 1 to about 12 carbon atoms, unless otherwise defined. In certain embodiments, an alkyl group has from 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms, or 1 to 3 carbon atoms. Examples of straight- or branched-chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, and octyl groups. Furthermore, the term "alkyl," as used throughout the specification, examples, and claims, is intended to include "unsubstituted alkyl" and "substituted alkyl," the latter of which refers to alkyl moieties having substituents replacing a hydrogen on one or more available carbon atoms in the hydrocarbon backbone. Unless otherwise specified, such substituents may include, for example, halogen groups (e.g., fluoro), hydroxyl groups, carbonyl groups (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl groups), thiocarbonyl groups (e.g., thioester, thioacetate, or thioformate groups), alkoxy groups, phosphoryl groups, phosphate groups, phosphonate groups, phosphinate groups, amino groups, amido groups, amidine groups, imine groups, cyano groups, nitro groups, azide groups, sulfhydryl groups, alkylthio groups, sulfate groups, sulfonate groups, sulfamoyl groups, sulfonamido groups, sulfonyl groups, heterocyclyl groups, aralkyl groups, or aromatic or heteroaromatic moieties. In preferred embodiments, the substituent on a substituted alkyl group is C 1-6 Alkyl group, C 3-6 The substituents on the substituted alkyl group are selected from cycloalkyl groups, halogen groups, carbonyl groups, cyano groups, and hydroxyl groups. In a more preferred embodiment, the substituents on the substituted alkyl group are selected from fluoro groups, carbonyl groups, cyano groups, and hydroxyl groups. Those skilled in the art will appreciate that the substituted moieties on the hydrocarbon chain may themselves be substituted, if desired. For example, substituents on the substituted alkyl group may include substituted and unsubstituted amino groups, azide groups, imino groups, amido groups, phosphoryl groups (including phosphonate groups and phosphinate groups), sulfonyl groups (including sulfate groups, sulfonamido groups, sulfamoyl groups, and sulfonate groups), and silyl groups, as well as ether groups, alkylthio groups, carbonyl groups (including ketone groups, aldehyde groups, carboxylate groups, and esters), -CF3, -CN, and the like. Exemplary substituted alkyl groups are described below. The cycloalkyl group may be further substituted with alkyl groups, alkenyl groups, alkoxy groups, alkylthio groups, aminoalkyl groups, alkyl groups substituted with carbonyl groups, -CF3, -CN, and the like. "C x-yThe term "C" when used in reference to a chemical moiety (e.g., an acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy group) is meant to encompass groups containing x to y carbon atoms in the chain. For example, "C x-y The term "alkyl group" includes straight-chain and branched-chain alkyl groups, substituted or unsubstituted, saturated hydrocarbon groups containing x to y carbon atoms in the chain, and also includes haloalkyl groups. Preferred haloalkyl groups include trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, and pentafluoroethyl groups. A CO alkyl group refers to a hydrogen atom when the group is in a terminal position, or a bond when the group is internal. The term "C 2-y Alkenyl group" and "C 2-y "Alkynyl" refers to substituted or unsubstituted unsaturated aliphatic groups analogous in length and substitutability to the alkyl groups described above, but which contain at least one double or triple bond respectively. The terms "amine" and "amino" are well known in the art and refer to unsubstituted and substituted amines and their salts, for example, groups represented by any of the following general formulas: [ka] In the formula, R A each independently represents a hydrogen or a hydrocarbyl group, or two R A together with the N atom to which they are attached form a heterocycle having 4 to 8 atoms in the ring structure. As used herein, the term "aryl" includes substituted or unsubstituted monocyclic aromatic groups in which each atom of the ring is a carbon atom. Preferably, the ring is a 6- or 20-membered ring, more preferably a 6-membered ring. Preferably, an aryl has 6 to 10 carbon atoms, more preferably 6 to 25 carbon atoms. The term "aryl" also includes polycyclic ring systems having two or more cyclic rings in which two or more carbon atoms are shared between two adjacent rings, where at least one of the rings is aromatic and the other rings may be, for example, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclyl groups. Aryl groups include benzene, naphthalene, phenanthrene, phenol, aniline, and the like. As used herein, the terms "carbocycle" and "carbocyclic" refer to a saturated or unsaturated ring in which each atom of the ring is a carbon atom. Preferably, a carbocyclic group has 3 to 20 carbon atoms. The term "carbocycle" includes both aromatic and non-aromatic carbocycles. Non-aromatic carbocycles include cycloalkane rings in which all carbon atoms are saturated and cycloalkene rings containing at least one double bond. Carbocycles include 5- to 7-membered monocyclic rings and 8- to 12-membered bicyclic rings. Each ring of a bicyclic carbocycle may be selected from saturated, unsaturated, and aromatic rings. Carbocycles include bicyclic molecules in which one, two, or three or more atoms are shared between the two rings. The term "fused carbocycle" refers to a bicyclic carbocycle in which each ring shares two adjacent atoms with the other ring. Each ring of a fused carbocycle may be selected from saturated, unsaturated, and aromatic rings. In typical embodiments, an aromatic ring (e.g., a phenyl (Ph) group) may be fused to a saturated or unsaturated ring (e.g., cyclohexane, cyclopentane, or cyclohexene). Any combination of saturated, unsaturated, and aromatic bicyclic rings, valence permitting, is included in the definition of carbocycle. Exemplary "carbocycles" include cyclopentane, cyclohexane, bicyclo[2.2.1]heptane, 1,5-cyclooctadiene, 1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]oct-3-ene, naphthalene, and adamantane. Examples of fused carbocycles include decalin, naphthalene, 1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]octane, 4,5,6,7-tetrahydro-1H-indene, and bicyclo[4.1.0]hept-3-ene. A "carbocycle" may be substituted at any one or more positions capable of retaining a hydrogen atom. As used herein, the terms "halo" and "halogen" refer to halogen atoms and include chlorine, fluorine, bromine, and iodine. The terms "heteroaryl" and "hetaryl" include substituted or unsubstituted aromatic monocyclic ring structures, preferably 5- to 20-membered, more preferably 5- to 6-membered, containing at least one heteroatom, preferably 1-4 heteroatoms, and more preferably 1 or 2 heteroatoms. Preferably, heteroaryls have 2-40 carbon atoms, more preferably 2-25 carbon atoms. The terms "heteroaryl" and "hetaryl" also include polycyclic ring systems having two or more cyclic rings in which two or more carbon atoms are shared between two adjacent rings, at least one of which is heterocyclic, and the other rings may be, for example, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclyl groups. Examples of heteroaryl groups include pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, and carbazole. The terms "heterocyclyl," "heterocycle," and "heterocyclic" refer to a substituted or unsubstituted, preferably 3- to 20-membered, more preferably 3- to 7-membered, non-aromatic ring structure containing at least one heteroatom, preferably 1 to 4 heteroatoms, and more preferably 1 or 2 heteroatoms. The terms "heterocyclyl" and "heterocyclic" also include polycyclic ring systems having two or more rings in which two or more carbon atoms are shared between two adjacent rings, where at least one of the rings is heterocyclic and the other rings may be, for example, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclyl groups. Heterocyclyl groups include, for example, piperidine, piperazine, pyrrolidine, morpholine, lactones, lactams, and the like. The term "substituted" refers to a moiety having a substituent replacing a hydrogen on one or more carbon atoms in the backbone. It should be understood that the terms "substituted" or "substituted with" imply that such substitution is in accordance with the valency of the substituted atom and the substituent, and that the substitution stabilizes the compound (e.g., does not spontaneously result in a transformation such as rearrangement, cyclization, or elimination). Optionally substituted moieties include any suitable substituent described herein, such as acyl, acylamino, acyloxy, alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylamino, alkylthio, arylthio, alkynyl, amido, amino, aminoalkyl, aralkyl, carbamate, carbocyclyl, cycloalkyl, carbocyclylalkyl, carbonate, ester, ether, heteroaralkyl, heterocyclyl, heterocyclylalkyl, hydrocarbyl, silyl, sulfone, or thioether. As used herein, the term "substituted" is intended to include all possible substituents present in organic compounds. In a broad sense, the substituents that may be present include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and non-aromatic substituents of organic compounds. The substituents that may be present may be one or more, the same or different, for appropriate organic compounds. For purposes of this invention, heteroatoms such as nitrogen may have hydrogen substituents and / or any substituents that may be present in organic compounds that satisfy the valence of the heteroatom as described herein. Substituents include any of the substituents described herein, such as halogens, hydroxyl groups, carbonyl groups (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl groups), thiocarbonyl groups (e.g., thioester, thioacetate, or thioformate groups), alkoxy groups, phosphoryl groups, phosphate groups, phosphonate groups, phosphinate groups, amino groups, amido groups, amidine groups, imine groups, cyano groups, nitro groups, azide groups, sulfhydryl groups, alkylthio groups, sulfate groups, sulfonate groups, sulfamoyl groups, sulfonamide groups, sulfonyl groups, heterocyclyl groups, aralkyl groups, or aromatic or heteroaromatic moieties.In a preferred embodiment, the substituents of the substituted alkyl group are C. 1-6 Alkyl group, C 3-6 The substituents are selected from cycloalkyl groups, halogen groups, carbonyl groups, cyano groups, and hydroxy groups. In a more preferred embodiment, the substituents of the substituted alkyl groups are selected from fluoro groups, carbonyl groups, cyano groups, and hydroxy groups. Those skilled in the art will understand that the substituents may themselves be substituted, if appropriate. Unless specifically described as "unsubstituted," references herein to chemical moieties are understood to include substituted modifications. For example, references to "aryl" groups or moieties implicitly include substituted and unsubstituted modifications. "Hole transport layer (HTL)" and similar terms refer to a layer made of a material that transports holes. A high hole transport capability is recommended. The HTL is used to block the passage of electrons transported by the emissive layer. A low electron affinity is typically required for electron blocking. The HTL should preferably have a high triplet potential to block exciton transfer from the adjacent emissive layer (EML). "Emitting layer" and similar terms refer to a layer that emits light. In some embodiments, the emitting layer is composed of a host material and a guest material. The guest material is also referred to as a dopant material, although the present disclosure is not limited thereto. The host material may be bipolar or unipolar and may be used alone or in combination with two or more host materials. The opto-electrical properties of the host material may vary depending on the type of guest material (TADF, phosphorescent, or fluorescent) used. For fluorescent guest materials, the host material should have good spectral overlap between the absorption of the guest material and the emission of the host material to induce good Förster transfer to the guest material. For phosphorescent guest materials, the host material should have high triplet energy to confine the triplet of the guest material. For TADF guest materials, the host material should have both spectral overlap and high triplet energy. "Dopant" and similar terms refer to additives for carrier transport layers, emissive layers, or other layers. In carrier transport layers, dopant and similar terms refer to electron acceptors or donors that, when added to an organic layer as an additive, increase the conductivity of the organic layer in an organic electronic device. Organic semiconductors can similarly be affected in terms of their electrical conductivity by doping. Such organic semiconductor matrix materials can be made from compounds with electron-donating or electron-accepting properties. In emissive layers, dopant and similar terms refer to emissive materials dispersed in a matrix, such as a host. When a triplet harvesting material is doped into the emissive layer or included in an adjacent layer to increase the exciton generation efficiency, it is called an assist dopant. The assist dopant can actually shorten the exciton lifetime. The content of the assist dopant in the emissive layer or an adjacent layer is not particularly limited, as long as the triplet harvesting material increases the exciton generation rate. The content of the assist dopant in the emissive layer is preferably greater than that of the emissive material, more preferably at least twice that of the emissive material. In the light-emitting layer, the content of the host material is preferably 50% by weight or more, the content of the assist dopant is preferably 5% by weight to less than 50% by weight, and the content of the light-emitting material is preferably 0% by weight to 30% by weight, more preferably 0% by weight to less than 10% by weight. The content of the assist dopant in the adjacent layer may be 50% by weight or more, or may be 100% by weight. When a device containing a triplet harvesting material in the light-emitting layer or an adjacent layer has a higher luminous efficiency than a device not containing the triplet harvesting material, the triplet harvesting material functions as an assist dopant. The light-emitting layer containing a host material, an assist dopant, and a light-emitting material satisfies the following (A), and preferably satisfies the following (B). ES1(A)>ES1(B)>ES1(C) (A) ET1(A)>ET1(B) (B) Here, ES1(A) represents the lowest excited singlet energy level of the host material, ES1(B) represents the lowest excited singlet energy level of the assist dopant, ES1(C) represents the lowest excited singlet energy level of the light-emitting material, ET1(A) represents the lowest excited triplet energy level of the host material at 77 K, and ET1(B) represents the lowest excited triplet energy level of the assist dopant at 77 K. The assist dopant preferably has an energy difference ΔE between the lowest singlet excited state and the lowest triplet excited state at 77 K of 0.3 eV or less, more preferably 0.2 eV or less, and even more preferably 0.1 eV or less. ST It has. In the compounds of the present invention, any atom not specified as a particular isotope is encompassed as any stable isotope of that atom. Unless otherwise specified, when a state is specified as "H" or "hydrogen," the state is understood to have hydrogen in its natural isotopic composition. Also, unless otherwise specified, when a state is specified as "D" or "deuterium," the state is understood to have an amount of deuterium at least 3340 times greater than the natural amount of deuterium, 0.015% (i.e., a deuterium content of at least 50.1%). As used herein, the term "isotope enrichment" refers to the ratio of the amount of an isotope to the amount of that particular isotope found in nature. In various embodiments, the compounds of the invention have an isotope enrichment (for each deuterium atom content) of at least 3500 (52.5% deuterium content for each deuterium atom content), at least 4000 (60% deuterium content), at least 4500 (67.5% deuterium content), at least 5000 (75% deuterium content), at least 5500 (82.5% deuterium content), at least 6000 (90% deuterium content), at least 6333.3 (95% deuterium content), at least 6466.7 (97% deuterium content), at least 6600 (99% deuterium content), or at least 6633.3 (99.5% deuterium content). The term "isotopomer" refers to species that differ from specific compounds of the invention only in isotopic composition. When referring to compounds of the present invention, the term "compound" refers to a collection of molecules having the same chemical structure, although isotopic variations may exist among the constituent atoms of the molecule. Thus, as will be apparent to those skilled in the art, a compound represented by a particular chemical structure containing a given deuterium atom may also contain some isotopic substitutions, which have hydrogen atoms in place of one or more of the given deuterium atoms within the structure. The relative amount of such isotopic substitutions in the compounds of the present invention will depend on many factors, including the isotopic purity of the deuteration reagent used to prepare the compound and the efficiency of deuterium incorporation in the various synthetic steps used to prepare the compound. However, as noted above, the relative amount of such isotopic substitutions is less than 49.9% of the overall compound. In other embodiments, the relative amount of such isotopic substitutions is less than 47.5%, less than 40%, less than 32.5%, less than 25%, less than 17.5%, less than 10%, less than 5%, less than 3%, less than 1%, or less than 0.5% of the overall compound. "Deuterium-substituted" refers to one or more hydrogen atoms being replaced with the corresponding number of deuterium atoms. "D" and "d" refer to deuterium.

[0033] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) are capable of emitting light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (e.g., 280-400 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means.

[0034] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, the Hartree-Fock equations can be solved using time-dependent density functional theory (TD-DFT / B3LYP / 6-31G*) with a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional, to screen for molecular fragments (moieties) with a HOMO above a certain threshold and a LUMO below a certain threshold, and the calculated triplet state of the moieties is greater than 2.75 eV. Thus, the donor moiety ("D") can be selected for its HOMO energy (e.g., ionization potential) of, for example, -6.5 eV or greater, and the acceptor moiety ("A") can be selected for its LUMO energy (e.g., electron affinity) of, for example, -0.5 eV or less. 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 tightly restricts the acceptor and donor moieties to specific configurations. In some embodiments, the compound library is screened using one or more of the following properties: 1. Emission around a specific wavelength 2. Calculated triplet states above a specific energy level 3. Delta E below a certain value ST value 4. Quantum yield above a certain value 5.HOMO level 6.LUMO level In one embodiment, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ST The value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0035] [Compositions using compounds of the present disclosure] In some embodiments, the compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, the compounds of Formula (1) may be combined with an electroactive material to form a film. In some cases, the compounds of Formula (1) may be combined with a hole transporting polymer. In some cases, the compounds of Formula (1) may be combined with an electron transporting polymer. In some cases, the compounds of Formula (1) may be combined with a hole transporting polymer and an electron transporting polymer. In some cases, the compounds of Formula (1) may be combined with a copolymer having both a hole transporting moiety and an electron transporting moiety. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0036] [Film formation] In one embodiment, a film containing the compound of the present invention 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. 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 one embodiment, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, the dry process can be a vacuum deposition process, but is not limited thereto. When a vacuum deposition process is used, the compounds constituting the film can be co-deposited from separate deposition sources, or from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders can be used, a compressed compact of the mixed powder can be used, or a mixture of the compounds can be used by heating, melting, and cooling. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, thereby forming a film with a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the deposition source as a deposition source, a film with a desired composition ratio can be easily formed. In some embodiments, the temperature at which each of the co-deposited compounds has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[0037] Examples of Use of Compounds of the Present Disclosure Organic Light-Emitting Diode: One aspect of the present invention relates to the use of a compound represented by general formula (1) of the present invention as an emitting material in an organic light-emitting device. In some embodiments, the compound represented by general formula (1) of the present invention can be effectively used as an emitting material in the emitting layer of an organic light-emitting device. In some embodiments, the compound represented by general formula (1) includes a delayed fluorescent material (delayed fluorescent material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of a compound represented by general formula (1) as a delayed fluorescent material. In some embodiments, the compound represented by general formula (1) can be used as a host material and can be used together with one or more emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF materials. In some embodiments, the compound represented by general formula (1) can also be used as a hole transport material. In some embodiments, the compound represented by general formula (1) can be used as an electron transport material. In some embodiments, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device containing the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the light-emitting layer comprises a compound represented by Formula (1), and the compound represented by Formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by Formula (1) relative to the film-forming surface influences or dictates the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by Formula (1) improves light extraction efficiency from the light-emitting layer. One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes an emissive layer. In one embodiment, the emissive layer includes a compound represented by general formula (1) as an emissive material. In one embodiment, the organic light-emitting device is an organic photoluminescent device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescent device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other emissive materials in the emissive layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) in the emissive layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material in the emissive layer and the lowest excited singlet energy level of the other emissive materials in the emissive layer. In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least an light-emitting layer. In some embodiments, the organic layer includes only an light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer with hole injection functionality, and the electron transport layer may be an electron injection transport layer with electron injection functionality. An example of an organic electroluminescent device is shown in Figure 1.

[0038] Emitting layer: In some embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has singlet and triplet excited energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, the singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency. That is, any host material that can achieve high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in an emissive material in an emissive layer of a device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from a host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from a compound represented by formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 10% by weight or less. In some embodiments, the host material of the light-emitting layer is an organic compound that has hole-transporting and electron-transporting functions. In some embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.

[0039] In some embodiments, the host material is selected from the group consisting of: [ka] [ka]

[0040] In one embodiment, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are in the order of highest to lowest. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. STis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The content of the first TADF molecules in the light-emitting layer is preferably greater than the content of the second TADF molecules. The content of the host material in the light-emitting layer is preferably greater than the content of the second TADF molecules. The content of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the content of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition of the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the photoexcitation luminescence quantum yield φPL1(A) of a co-deposited film of the first TADF molecules and the host material (where the content of the first TADF molecules in the co-deposited film is A wt %) and the photoexcitation luminescence quantum yield φPL2(A) of a co-deposited film of the second TADF molecules and the host material (where the content of the second TADF molecules in the co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photoexcitation luminescence quantum yield φPL2(B) of a co-deposited film of the second TADF molecules and the host material (where the content of the second TADF molecules in the co-deposited film is B wt %) and the photoexcitation luminescence quantum yield φPL2(100) of a film of the second TADF molecules alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the light-emitting layer may contain three structurally different TADF molecules, and the compound of the present invention may be any of the TADF compounds contained in the light-emitting layer. In some embodiments, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer does not contain a metal element. 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, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, and nitrogen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011955, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 081088, and ~0071 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of JP 2013-256490 A, paragraphs 0008~0020 and 0038~0040 of JP 2013-116975 A, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359 A, paragraph 0 of WO2013 / 161437 A 008 to 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of JP 2014-9352 A, paragraphs 0008 to 0048 and 0067 to 0076 of JP 2014-9224 A, paragraphs 0013 to 0025 of JP 2017-119663 A, paragraphs 0013 to 0026 of JP 2017-119664 A, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP 017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO 2018 / 047853 A, particularly exemplary compounds, that are capable of emitting delayed fluorescence are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO2013 / 133359 A, WO2014 / 034535 A, WO2014 / 115743 A, WO2014 / 122895 A, WO2014 / 126200 A, WO2014 / 136758 A, WO2014 / 133121 A, WO20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0041] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, and the substrate is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0042] 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 greater). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is 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, the anode has a transmittance of greater than 10% when emitted light passes through it, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0043] 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), alloy, conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron-injecting metal and a second metal, which is a stable metal having a higher work function than the electron-injecting metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injecting properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms 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, one of the anode and 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 semi-transparent cathode. In some embodiments, a device includes an anode and a cathode, both of which are transparent or semi-transparent.

[0044] Injection layer: An injection layer is a layer between an electrode and an organic layer. In some embodiments, the injection layer reduces driving voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the 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. Preferred examples of compounds that can be used as hole injection materials are listed below.

[0045] [ka]

[0046] Next, preferred examples of compounds that can be used as the electron injection material will be listed. [ka]

[0047] Barrier layer: A blocking 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 blocking 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 functionality of an electron blocking layer and an exciton blocking layer.

[0048] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer prevents holes from reaching the electron transport layer during electron transport. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are listed below.

[0049] [ka]

[0050] Electron barrier 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 can 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.

[0051] [ka]

[0052] 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 enables 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.

[0053] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0054] [ka]

[0055] 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.

[0056] [ka]

[0057] 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.

[0058] [ka]

[0059] 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 by the exemplified compounds. Furthermore, even if a compound is given as an example of a material having a specific function, it can also be used as a material having other functions.

[0060] [device] In some embodiments, the compounds of the present disclosure are incorporated into devices, including, but not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, cell phones, and tablets. In one embodiment, an electronic device includes an OLED having an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode, the emissive layer including a host material and a compound represented by General Formula (1). In some embodiments, the light-emitting layer of the OLED further comprises a fluorescent material in which the compound represented by general formula (1) converts triplets to singlets for phosphorescence. 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. Devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detection devices, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0061] [Bulb or Lamp] In one embodiment, an electronic device includes an OLED including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode, and an OLED driver circuit, wherein the emissive layer includes a host material and a compound represented by General Formula (1) as an emissive material. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a 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 one embodiment, the device is an OLED light comprising: (1) a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; (2) at least one OLED on the mounting surface, the at least one OLED configured to emit light, the at least one OLED including at least one organic layer including an anode, a cathode, and an emissive layer between the anode and the cathode, the emissive layer including a host material and a compound represented by general formula (1) as an emissive material; (3) a housing for the circuit board; and (4) 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 includes multiple OLEDs mounted on a circuit board to emit light in multiple directions. In some embodiments, some of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0062] [OLED principle] OLEDs typically consist of a layer of organic material or compound between two electrodes (anode and cathode). Organic molecules are electrically conductive due to the delocalization of π electrons resulting from bonding with some or all of the molecules. When a voltage is applied, electrons from the highest occupied molecular orbital (HOMO), present at the anode, flow into the lowest unoccupied molecular orbital (LUMO) of the organic molecule, present at the cathode. Removal of an electron from the HOMO is also referred to as injecting an electron-hole into the HOMO. Electrostatic forces force the electron and hole toward each other, causing them to recombine and form an exciton (a combined electron-hole state). When the excited state is deactivated and the electron energy levels relax, radiation with frequencies in the visible spectrum is emitted. The frequency of this radiation depends on the bandgap of the material, i.e., the energy difference between the HOMO and LUMO. When electrons and holes are fermions with half-integer spins, excitons can exist in either a singlet or triplet state, depending on how the electron and hole spins couple. Statistically, three triplet excitons are formed for every singlet exciton. Decay from the triplet state is spin-forbidden, which increases the transition timescale and limits the internal efficiency of fluorescent devices. Phosphorescent organic light-emitting diodes utilize spin-orbit coupling to promote intersystem crossing between the singlet and triplet states, thereby generating light emission from both the singlet and triplet states and improving internal efficiency. One prototypical phosphorescent material is iridium tris(2-phenylpyridine) (Ir(ppy)3), in which charge transfer from the Ir atom to an organic ligand results in an excited state. Such an approach has reduced the triplet lifetime to about a few microseconds, several orders of magnitude slower than the radiative lifetime of fully allowed transitions such as fluorescence. While Ir-based phosphors have proven acceptable for many display applications, losses due to high triplet density have prevented the application of OLEDs to high-brightness solid-state lighting devices. Thermally activated delayed fluorescence (TADF) is a luminescent material that emits light with a large energy difference between the singlet and triplet states (ΔE ST The reduction of the exchange splitting from typical values ​​of 0.4–0.7 eV to gaps on the order of thermal energy (proportional to kBT, where kB is the Boltzmann constant and T is the temperature) means that thermal stirring can transition the population between the singlet and triplet levels on reasonable timescales, even if the coupling between the states is small. TADF molecules consist of donor and acceptor moieties that are linked by a covalent bond directly or via a conjugated linker (or "bridge"). The "donor" moiety has the property of transferring an electron from its HOMO to the "acceptor" moiety upon excitation. The "acceptor" moiety has the property of accepting an electron from the "donor" moiety to its LUMO. The donor-acceptor nature of TADF molecules allows for very low ΔE STThis results in a low-lying excited state that exhibits charge transfer, indicating a . Because thermal molecular motion can randomly change the optical properties of the donor-acceptor system, the rigid steric configuration of the donor and acceptor moieties can be used to limit non-radiative deactivation of the charge-transfer state by internal conversion during the excited state lifetime. Therefore, ΔE ST It would be beneficial to develop systems with high reverse intersystem crossing (RISC) that can utilize triplet excitons and reduce the charge transport. Such systems would result in increased quantum efficiency and reduced emission lifetime. Systems with these characteristics would be able to emit light without the rapid decomposition typically seen in today's OLEDs.

[0063] [Display or Screen] In some embodiments, the compound represented by general formula (1) can be used in a screen or display. In some embodiments, the compound represented by general formula (1) is deposited onto a substrate using a process 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. Screens (also called masks) are used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for 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 onto 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 within the pixel area protects etching in specific regions until these specific patterns are undercut and removed from the substrate. At that point, all pixel areas are subjected to similar etch rates, but the 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 the pixel, enabling the deep, localized etching required to create steep vertical bevels. The preferred material for the evaporation mask is Invar, a metal alloy that is cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a rotating mandrel as a nickel mask. A suitable, low-cost method for forming open areas in the evaporation 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.

[0064] [Method for manufacturing a device using the compound of the present disclosure] OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. In another aspect of the present invention, there is provided a method for manufacturing an organic light-emitting diode (OLED) display, the method including the steps of forming a barrier layer on a base substrate of a mother panel, forming a plurality of display units in cell panels on the barrier layer, 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 one embodiment, the barrier layer is an inorganic film made of, for example, SiNx, and the edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In one embodiment, the organic film helps the mother panel to be cut softly into individual cell panels. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to either the display unit or the encapsulation layer. Each of the organic film and the planarization film may include one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate before forming the barrier layer on the other surface of the base substrate formed of polyimide, 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 is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film directly contacts the base substrate and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer. In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, and in some embodiments, the pixel electrode is coupled to the source / drain electrodes of the TFT layer. In one embodiment, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display units and prevents 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 an interval with each of the multiple display units. In some embodiments, the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer. In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and the carrier substrate is then separated. In some embodiments, the 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. In one embodiment, 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 one embodiment, a TFT layer for each cell panel is formed, and a passivation layer (an inorganic film) and a planarization film (an organic film) are disposed on and cover the TFT layer. At the same time as the planarization film (e.g., polyimide or acrylic) is formed, the grooves in the interface are covered with an organic film (e.g., 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 impacts that may occur. That is, if all barrier layers were completely exposed without the organic film, the impacts would be transmitted to the barrier layers when each cell panel was cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves in the interface between the barrier layers are covered with an organic film to absorb any impacts that would otherwise be transmitted to the barrier layers, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layers. In one embodiment, the organic film and the planarizing film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarizing film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarizing film and the remaining portion of the organic film, so the organic film and the planarizing film are spaced apart from each other such that the organic film is spaced apart from the display unit. In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is irradiated onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, the grooves at the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting. In some embodiments, cracks can be prevented from occurring in the barrier layer during cutting. In one embodiment, the method reduces product rejection rates and stabilizes product quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the edges of the barrier layer. [Example]

[0065] The following synthesis examples and examples further illustrate the features of the present invention. The materials, processing details, processing procedures, and other aspects described 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 described below. The characteristics of the following samples were evaluated using an NMR (500 MHz nuclear magnetic resonance spectroscopy, Bruker), an LC / MS (liquid chromatography mass spectrometer, Waters), an AC3 (Riken Keiki), a high-performance UV / Vis / NIR spectrophotometer (Lambda 950, PerkinElmer), a fluorescence spectrophotometer (FluoroMax-4, Horiba), a photonic multichannel analyzer (PMA-12 C10027-01, Hamamatsu Photonics), an absolute PL quantum yield measurement system (C11347, Hamamatsu Photonics), and an automatic current-voltage-luminance measurement system (ETS-170, System Giken).

[0066] [Synthesis Example 1] Compound 1 was synthesized according to the following scheme. [ka]

[0067] Compound a (5.0 g, 17.3 mmol) was added to a solution (52 mL) of compound b (6.7 g, 20.8 mmol) and potassium carbonate (4.8 g, 34.7 mmol) in N-methyl-2-pyrrolidone (NMP) under a nitrogen stream, and the mixture was stirred at 110 °C for 15 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. This was purified by silica gel column chromatography (dichloromethane:hexane = 1:2) to obtain compound c (6.75 g, 11.5 mmol, 83% yield) as a white solid. 1 H NMR (500 MHz, CDCl3, δ): 8.38 (s, 2H), 7.91 (s, 2H), 7.74-7.71 (m, 6H), 7.51-7.48 (m, 6H),7.37 (t, J = 7.5 Hz, 2H) ASAP mass spectrum analysis: Calculated 587.7, observed 587.9

[0068] To a solution of compound c (0.20 g, 0.34 mmol) and diphenylamine (0.10 g, 0.82 mmol) in toluene (1.4 mL), tri-t-butylphosphine tetrafluoroborate (10 mg, 0.03 mmol), tris(dibenzylideneacetone)dipalladium(0) (16 mg, 0.02 mmol), and sodium t-butoxide (0.13 g, 1.4 mmol) were added under a nitrogen stream and stirred at 80 °C for 15 hours. The mixture was returned to room temperature and filtered through Celite. The solvent was evaporated from the filtrate, and methanol was added to the residue. The suspension was filtered and washed with methanol. This was purified by silica gel column chromatography (dichloromethane:hexane = 1:1) to obtain compound d (0.20 g, 0.26 mmol, 76% yield) as a white solid. 1H NMR (500 MHz, CDCl3, δ): 8.34 (s, 2H), 7.68 (d, J = 7.5 Hz, 4H), 7.58 (d, J = 8.5 Hz, 2H), 7.47 (t, J = 7.5 Hz, 4H), 7.36 (t, J = 8.5 Hz, 4H), 7.33 (s, 2H), 7.29 (t, J = 8.0 Hz, 8H), 7.10 (t, J = 8.0 Hz, 8H), 7.02 (t, J = 7.5 Hz, 4H) ASAP mass spectrum analysis: theoretical 763.3, observed 764.4

[0069] Under a nitrogen stream, t-BuLi (1.9 mol / L pentane solution, 2.1 mL, 3.9 mmol) was added to a solution of compound d (2.0 g, 2.6 mmol) in toluene (39 mL) at 0 °C and stirred at 90 °C for 1 hour. The reaction mixture was cooled to 0 °C, tribromoboron (0.98 g, 3.9 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. N-ethyldiisopropylamine (0.68 g, 5.2 mmol) was added to the reaction mixture and stirred at 100 °C for 15 hours. The resulting reaction mixture was filtered through Celite, and the solvent in the filtrate was evaporated. This was purified by silica gel column chromatography (ethyl acetate:hexane = 1:9) to obtain compound 1 (0.73 g, 0.99 mmol, 38% yield) as a yellow solid. 1 H NMR (500 MHz, CDCl3, δ): 9.02 (d, J = 7.5 Hz, 2H), 8.27 (s, 2H), 7.69-7.64 (m, 8H), 7.54 (d, J = 8.5 Hz, 2H), 7.51-7.45 (m, 12H), 7.38 (d, J = 8.5 Hz, 2H), 7.34 (t, J = 7.5 Hz, 4H), 6.83 (d, J = 8.5 Hz, 2H), 6.38 (s, 2H) ASAP mass spectrum analysis: Calculated 737.3, observed 737.5

[0070] [Synthesis Example 2] Compound 2 was synthesized according to the following scheme. [ka]

[0071] Under a nitrogen stream, PdCl2(Am-phos)2 (Amphos: 16 mg, 0.020 mmol) and potassium t-butoxide (250 mg, 2.3 mmol) were added to a xylene (8 mL) solution of compound e (415 mg, 0.75 mmol) and p,p'-ditolylamine (370 mg, 1.9 mmol) and stirred at 80 °C for 15 hours. The mixture was returned to room temperature and the solvent was distilled off. The residue was dissolved in dichloromethane and methanol was added. The suspension was filtered and the residue was washed with methanol. This was purified by silica gel column chromatography (toluene:hexane = 1:1) to give compound f (410 mg, 0.53 mmol, 72% yield) as a white solid. 1 H NMR (500 MHz, CDCl3, δ): 8.30 (s, 2H), 7.70 (d, J = 8.0 Hz, 4H), 7.62 (d, J = 8.5 Hz, 2H), 7.47 (t, J = 8.5 Hz, 6H), 7.34 (t, J = 7.5 Hz, 2H), 7.05 (m, 16H), 6.80 (s, 1H), 6.70 (s, 2H), 2.27 (s, 12H) ASAP mass spectrum analysis: Calculated 786.4, observed 786.5

[0072] Triiodoboron (390 mg, 1.0 mmol) and triphenylboron (920 mg, 0.80 mmol) were added to a solution of compound f (310 mg, 0.40 mmol) in o-dichlorobenzene (1.0 mL) under a nitrogen stream, and the mixture was stirred at 150 °C for 15 hours. Water was added to the reaction solution, which was then extracted with toluene, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then distilled off. The resulting mixture was purified by silica gel column chromatography (ethyl acetate:hexane = 1:20) to obtain compound 2 (46 mg, 0.060 mmol, 15% yield) as a yellow solid. Compound 2: 1H NMR (500 MHz, CDCl3, δ): 9.32 (s, 2H), 8.98 (s, 2H), 8.74 (s, 2H), 7.98 (d, J = 7.0 Hz, 2H), 7.64 (t, J = 7.5 Hz, 4H), 7.50-7.47 (m, 6H), 7.18-7.05 (m, 12H), 6.80 (d, J = 8.5 Hz, 2H), 2.57 (s, 6H), 2.53 (s, 6H) ASAP mass spectrum analysis: 794.4 theoretical, 794.5 observed

[0073] [Synthesis Example 3] Compound 3 was synthesized according to the following scheme. [ka]

[0074] A solution of 3-biphenylamine (compound g, 3.0 g, 18 mmol) and 3-bromobiphenyl (compound h, 3.7 g, 16.0 mmol) in toluene (36 mL) was added to tri-t-butylphosphine tetrafluoroborate (514 mg, 1.77 mmol), tris(dibenzylideneacetone)dipalladium(0) (810 mg, 0.89 mmol), and sodium t-butoxide (3.4 g, 36 mmol) under a nitrogen stream and stirred at 90 °C for 15 hours. The mixture was then cooled to room temperature and filtered through Celite. The filtrate was evaporated and purified by silica gel column chromatography (dichloromethane:hexane = 1:3) to give compound i (3.6 g, 11 mmol, 70% yield) as a colorless liquid. 1 H NMR (500 MHz, CDCl3, δ): 7.69 (d, J = 7.5 Hz, 4H), 7.46 (t, J = 7.5 Hz, 4H), 7.39-7.36 (m, 6H), 7.20 (d, J = 7.5 Hz, 2H), 7.15 (d, J = 7.5 Hz, 2H), 5.89 (brs, 1H) ASAP mass spectrum analysis: Calculated 321.2, observed 321.1

[0075] To a solution of compound c (2.5 g, 4.3 mmol) and compound i (3.0 g, 9.4 mmol) in toluene (17 mL), tri-t-butylphosphine tetrafluoroborate (120 mg, 0.43 mmol), tris(dibenzylideneacetone)dipalladium(0) (190 mg, 0.21 mmol), and sodium t-butoxide (1.6 g, 17.0 mmol) were added under a nitrogen stream, and the mixture was stirred at 90 °C for 15 hours. The mixture was returned to room temperature and filtered through Celite. The solvent was evaporated from the filtrate, and methanol was added to the residue. The suspension was filtered, and the residue was washed with methanol. This was purified by silica gel column chromatography (dichloromethane:hexane = 1:2) to obtain compound j (3.7 g, 3.5 mmol, 82% yield) as a white solid. 1 H NMR (500 MHz, CDCl3, δ): 8.30 (s, 1H), 7.66 (d, J = 7.5 Hz, 2H), 7.56 (d, J = 7.5 Hz, 4H), 7.48-7.41 (m, 10H), 7.63 (d, J = 7.5 Hz, 2H), 7.31-7.30 (m, 4H), 7.13 (d, J = 7.5 Hz, 2H) ASAP mass spectrum analysis: theoretical 1068.4, observed 1068.6

[0076] Under a nitrogen stream, t-BuLi (1.9 mol / L pentane solution, 2.0 mL, 3.8 mmol) was added to a solution of compound j (2.7 g, 2.5 mmol) in toluene (37 mL) at 0 °C and stirred at 90 °C for 1 h. The reaction mixture was cooled to 0 °C, tribromoboron (0.95 g, 3.8 mmol) was added, and the mixture was stirred at room temperature for 40 min. N-ethyldiisopropylamine (0.98 g, 7.6 mmol) was added to the reaction mixture and stirred at 100 °C for 15 h. The resulting reaction mixture was filtered through Celite, and the solvent in the filtrate was evaporated. The mixture was purified by silica gel column chromatography (toluene:hexane = 1:2-2:3, ethyl acetate:hexane = 1:9) to obtain compound 3 (0.85 g, 0.82 mmol, 32% yield) as a yellow solid. 1 H NMR (500 MHz, CDCl3, δ): 9.18 (d, J = 8.0 Hz, 2H), 8.26 (s, 2H), 7.88-7.34 (m, 42H), 7.24 (brs, 3H), 6.52 (s, 2H) ASAP mass spectrum analysis: theoretical 1041.4, observed 1041.5

[0077] [Synthesis Example 4] Compound 271 was synthesized according to the following scheme. [ka]

[0078] Compound k (0.32 g, 1.0 mmol) was added to a dimethylformamide solution (10 mL) of carbazole (0.35 g, 2.1 mmol) and potassium carbonate (0.42 g, 3.0 mmol) under a nitrogen stream, and the mixture was stirred at 130 °C for 15 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. This was purified by silica gel column chromatography (dichloromethane:hexane = 1:2) to obtain compound m (0.42 g, 0.68 mmol, 68% yield) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 8.15 (d, J = 7.7 Hz, 4H), 8.00 (d, J= 0.8 Hz, 2H), 7.48 (t, J = 7.7 Hz, 4H), 7.33 (t, J = 7.7 Hz, 4H), 7.20 (d, J = 8.1 Hz, 4H). ASAP mass spectrum analysis: Calculated 611.97, observed 612.90

[0079] A solution of compound m (7.36 g, 12.0 mmol) and 3,6-diphenylcarbazole (5.74 g, 18.0 mmol) in dimethylformamide (120 mL) was added with 1,10-phenanthroline (2.16 g, 12.0 mmol), copper iodide (2.29 g, 12.0 mmol), and potassium carbonate (3.31 g, 24.0 mmol) under a nitrogen stream and stirred at 135 °C for 6 hours. The mixture was cooled to room temperature, water was added, and the precipitated solid was filtered through Celite. The residue was dissolved in dichloromethane. The solvent was evaporated from the filtrate, and the mixture was purified by silica gel column chromatography (toluene:hexane = 4:6-1:0) to obtain compound n (6.29 g, 7.81 mmol, 65% yield) as a white solid. 1 HNMR (400 MHz, CDCl3, δ): 8.35 (s, 2H), 8.19 (d, J= 7.7 Hz, 4H), 8.05 (s, 2H), 7.71-7.66 (m, 8H), 7.54 (t, J = 7.7 Hz, 4H), 7.46 (t, J = 7.7 Hz, 4H), 7.39 (d, J = 7.7 Hz, 6H), 7.35 (d, J = 7.7 Hz, 4H). ASAP mass spectrum analysis: theoretical value 803.19, observed value 804.25

[0080] Under a nitrogen stream, n-BuLi (1.6 mol / L hexane solution, 0.04 mL, 0.06 mmol) was added to a solution of compound n (48 mg, 0.06 mmol) in toluene (0.6 mL) at -30 °C and stirred at 0 °C for 30 min. The reaction mixture was cooled to -30 °C, tribromoboron (16.5 mg, 0.07 mmol) was added, and the mixture was stirred at room temperature for 30 min. N,N-diisopropylethylamine (15.5 mg, 0.12 mmol) was added to the reaction mixture and stirred at 120 °C for 3 h. The resulting reaction mixture was filtered through Celite, and the solvent in the filtrate was distilled off. This was purified by silica gel column chromatography (ODCB) to obtain compound 4 (31 mg, 0.03 mmol, 58% yield) as a yellow solid. 1H-NMR (400 MHz, CDCl3, δ): 9.08 (d, J = 7.4 Hz, 2H), 8.67 (s, 2H), 8.52 (s, 2H), 8.46 (d, J = 7.4 Hz, 2H), 8.38 (d, J= 8.5 Hz, 2H), 8.28 (d, J = 7.4 Hz, 2H), 7.95 (d, J = 8.5 Hz, 2H), 7.82-7.77 (m, 8H), 7.58-7.45 (m, 8H), 7.38 (t, J = 7.4 Hz, 2H). ASAP mass spectrum analysis: Calculated 733.80, observed 733.27

[0081] [Example] Vacuum deposition method on a quartz substrate at a vacuum level of 3 x 10 -3 Compound 1 and PYD2Cz were evaporated from different evaporation sources under conditions of less than Pa to form a thin film with a thickness of 100 nm and a concentration of Compound 1 of 1 wt %.

[0082] [Comparative Example] A thin film was formed in the same manner except for using the following comparative compound 1 instead of compound 1, and this was used as a doped thin film of comparative example 1. In the structure of comparative compound 1, Ph represents an unsubstituted phenyl group.

[0083] [Measurement and Evaluation] The emission spectra of these thin films were observed using 300 nm excitation light, and the emission maximum wavelength and full width at half maximum were measured, as well as the photoluminescence quantum efficiency (PLQY). The results are shown in Table 2. The results in Table 2 indicate that, despite the fact that Compound 1 has a wider conjugated system than Comparative Compound 1, the emission maximum wavelength is shorter. Furthermore, Compound 1 has a smaller full width at half maximum and a higher photoluminescence quantum efficiency than Comparative Compound 1, indicating superior emission properties. [Table 2]

[0084] The relationship between Compound 1 of the present invention and Comparative Compound 1 is the same as the relationship between Compound 2 of the present invention and Comparative Compound 2, the relationship between Compound 3 of the present invention and Comparative Compound 3, and the relationship between Compound 271 of the present invention and Comparative Compound 271. For example, a thin film formed using compound 3 instead of compound 1 has a shorter maximum emission wavelength, a smaller full width at half maximum, and a higher PLQY than a thin film formed using comparative compound 3 instead of compound 1. Specifically, it has been confirmed that the thin film formed using compound 3 has a maximum emission wavelength of 468 nm, a small full width at half maximum of 27 nm, and a high PLQY of 90%. For example, it has been confirmed that a thin film formed using comparative compound 271 instead of compound 1 has an emission maximum wavelength of 486 nm and a full width at half maximum of 42 nm, whereas a thin film formed using compound 271 of the present invention has a shorter emission maximum wavelength of 473 nm and a significantly smaller full width at half maximum of 28 nm. It has also been confirmed that a thin film formed using compound 271 of the present invention maintains high luminous efficiency. The relationship between the compounds of the present invention and the comparative compounds is also supported by computational chemistry using the Q-Chem 5.1 program from Q-Chem. Here, the molecular structure in the ground singlet state SO was optimized and the electronic state was calculated using the B3LYP / 6-31G(d) method. The lowest excited singlet energy level (E S1 ) was calculated using the time-dependent density functional theory (TD-DFT). As a result, the calculated results showed that the wavelength of Compound 1 was shorter than that of Comparative Compound 1, which agreed well with the trend of the measured emission maximum wavelength. When the same calculation was performed for Compound 2 and Comparative Compound 2, the calculated results showed that the wavelength of Compound 2 was shorter than that of Comparative Compound 2.

[0085] [ka] [ka]

[0086] Thermogravimetric differential thermal analysis of compound 1 was performed using a thermogravimetric differential thermal analyzer (STA 2500 Regulus, NETSCH). The measurement was performed at atmospheric pressure while increasing the temperature from 20°C to 500°C at a rate of 10°C / min. Figure 2 shows a graph showing the results of weight change measurement (TG) and a graph showing the results of differential thermal analysis (DTA). Figure 2 shows that the temperature (Td5) at which compound 1 loses 5% of its mass from the initial value exceeds 500°C, confirming that compound 1 has excellent heat resistance. The heat resistance of Compound 2, Compound 3 and Compound 271 can also be evaluated in the same manner. [Industrial Applicability]

[0087] According to the present invention, it is possible to provide a compound having excellent luminescent properties and a compound that emits light at a short wavelength. Therefore, the luminescent material of the present invention can be effectively used in organic light-emitting devices such as organic electroluminescence elements. Therefore, the present invention has high industrial applicability. [Explanation of symbols]

[0088] 1 board 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6 Electron transport layer 7 Cathode

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 [In general formula (1), Y １ is N-R Ａ Represents. Y ２ is O, S, C=O or N-R Ａ Represents. R Ａ are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. represents an aryl group. R １ and R ３ ~R １１ each independently represents a hydrogen atom or a substituent, or 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 Ａ and R 4 are bonded to each other to form a cyclic structure. ２ is the following general formula It is a group represented by (2). 【Chemistry 2】 R ２１ ~R ２８ each independently represents a hydrogen atom or a substituent, or R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２５ and R ２６ , R ２６ and R ２７ , R ２７ and R ２８ Is that They are bonded to each other to form a ring structure. ２１ ~R ２８ At least one of is a substituted or unsubstituted aryl group. The general formula (1) satisfies any one of the following conditions 1 to 3. Condition 1: R ５ and R １０ are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, R ４ , R ６ , R ９ and R １１ is a hydrogen atom do. Condition 2: R ６ and R ９ are each independently a substituted or unsubstituted alkyl group. Condition 3: 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 Ａ and R 4 do not bond to each other to form a cyclic structure. stomach. * indicates the bond position.

2. Y ２ N-R Ａ 2. The compound of claim 1, wherein:

3. R ７ and R ８ The compound according to claim 1 or 2, wherein both are hydrogen atoms.

4. R Ａ are each independently a substituted or unsubstituted aryl group. Item 1. The compound according to item 1.

5. R １ and R ３ ~R １１ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, or or a substituted or unsubstituted aryl group, thing.

6. R ５ and R １０ are each independently a substituted or unsubstituted aryl group, or a substituted or The compound according to any one of claims 1 to 5, which is an unsubstituted alkyl group.

7. R ６ and R ９ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted The compound according to any one of claims 1 to 6, which is a substituted alkyl group.

8. R in general formula (2) ２１ ~R ２８ are each independently a hydrogen atom or a substituted or unsubstituted 8. Any of claims 1 to 7, wherein the aryl group is a substituted or unsubstituted heteroaryl group. The compound according to any one of claims 1 to 10.

9. R in general formula (2) ２３ and R ２６ At least one of the groups is substituted or unsubstituted. The compound of claim 8, which is an aryl group.

10. R in general formula (2) ２３ and R ２６ each independently represents a substituted or unsubstituted aryl; The compound of claim 9, wherein the compound is a group.

11. 10. The compound of claim 1 having any of the following structures: 【Transformation 3】

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

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

14. 10. The device according to claim 9, wherein the device has a layer comprising the compound, the layer also comprising a host material.

14. The organic light-emitting device according to 13.

15. The device has a layer containing the compound, and the layer has a structure different from the compound.

14. The organic light emitting device of claim 13, also comprising a light emitting material having

16. 10. The device according to claim 1, wherein the compound emits the greatest amount of light of any of the materials contained therein.

16. The organic light-emitting device according to any one of claims 3 to 15.

17. The amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound according to claim 15 . Organic light-emitting devices.

18. The photodiode according to any one of claims 13 to 17, which is an organic light emitting diode (OLED). Machine light-emitting device.

19. The organic light-emitting device according to any one of claims 13 to 18, which emits delayed fluorescence.

20. A compound represented by the following general formula (A): 【Chemistry 4】 [In general formula (A), X １ represents a halogen atom. Y １ is N-R Ａ Represents. Y ２ is O, S, C=O or N-R Ａ Represents. R Ａ are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. represents an aryl group. R １ and R ３ ~R １１ each independently represents a hydrogen atom or a substituent, or 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 Ａ and R 4 is are bonded to each other to form a ring structure. ２ is represented by the following general formula (2): It is a group that can be 【Transformation 5】 R ２１ ~R ２８ each independently represents a hydrogen atom or a substituent, or R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２５ and R ２６ , R ２６ and R ２７ , R ２７ and R ２８ Is that They are bonded to each other to form a ring structure. ２１ ~R ２８ At least one of is a substituted or unsubstituted aryl group. The general formula (1) satisfies any one of the following conditions 1 to 3. Condition 1: R ５ and R １０ are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, R ４ , R ６ , R ９ and R １１ is a hydrogen atom do. Condition 2: R ６ and R ９ are each independently a substituted or unsubstituted alkyl group. Condition 3: 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 Ａ and R 4 do not bond to each other to form a cyclic structure. stomach. * indicates the bond position.

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