Compounds, host materials, hole barrier materials, and organic light-emitting devices

Abstract

To provide a compound useful as a host material.SOLUTION: The invention provides a compound of the general formula in the figure, where: Z1 is N or C(R11); Z2 is N or C(R12); and R1 to R12 are each a hydrogen atom, a deuterium atom, or a substituent, provided that at least one of R1 to R12 is a dibenzofuryl group or the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to a compound useful as a host material, and to an organic light-emitting device using the same compound. [Background technology]

[0002] Active research and development is underway on materials used in organic light-emitting devices such as organic electroluminescent devices (organic EL devices). In particular, various attempts have been made to improve the characteristics of organic electroluminescent devices by newly developing and combining electron transport materials, hole transport materials, light-emitting materials, and host materials that constitute the device. As for host materials, compounds with the following structures, for example, have been widely recognized as useful host materials (Non-Patent Documents 1-3). [ka] [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] JYLee et al.,Chem.Eur.J.2013,19(4),1194-1198 [Non-Patent Document 2] CWLee et al.,Organic Electronics,14(2013),1009-1014 [Non-Patent Document 3] KSYook et al., Journal of Luminescence, 143(2013), 432-435 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, even when using conventionally known host materials, it may not always be possible to provide an organic light-emitting device having excellent characteristics. For example, when combined with a delayed fluorescence material, even if a host material that is considered useful is used as it is, it is often impossible to manufacture an organic light-emitting device having excellent characteristics. In particular, when used in an organic electroluminescence device, there is room for improvement in terms of the driving voltage. Therefore, the inventors have conducted studies for the purpose of improving the characteristics of an organic light-emitting device by providing an excellent host material.

Means for Solving the Problems

[0005] As a result of intensive studies, the inventors have found that the characteristics can be improved by using a compound having a specific structure in an organic light-emitting device. The present invention has been proposed based on such findings and specifically has the following configuration.

[0006] [1] A compound represented by the following general formula (1).

Chemical Formula

Chemical formula

[10] Z 1 is C(R 11 ) and Z 2 is C(R 12 ) and Z 3 and Z 4 The compound described in [8], wherein N is present.

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

[10] , wherein the molecule contains only one group represented by the general formula (2).

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

[10] , wherein the molecule contains only two groups represented by the general formula (2).

[13] R 1 ~R 6 , R 11 , R 12 A compound according to any one of [1] to

[12] , wherein at least one of the groups is represented by the general formula (2).

[14] R 7 ~R 10 A compound according to any one of [1] to

[13] , wherein at least one of the groups is represented by the general formula (2).

[15] The compound according to any one of [1] to

[14] , wherein the group represented by the general formula (2) has a structure represented by the general formula (2a) below. [ka] [In general formula (2a), R21 and R 22 Each of the following independently represents a deuterium atom or substituent, and Ar represents a substituted or unsubstituted arylene group. n1 represents an integer from 0 to 4, n2 represents an integer from 0 to 3, and n3 represents 0 or 1. Adjacent R 21 Allies, adjacent R 22 They may be bonded to each other to form a ring structure. X is O, S, C(R 23 )(R 24 ) or N(R 25 ) represents R 23 and R 24 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 25 * represents a substituent. * represents a bond position.

[16] A compound described in any one of [1] to

[15] , wherein X is O.

[17] R 1 ~R 12 A compound according to any one of [1] to

[16] , wherein each of them is independently a hydrogen atom, a deuterium atom, or a group represented by the general formula (2).

[18] A symmetric compound, one of the compounds described in [1] to

[17] .

[19] A host material containing one of the compounds described in [1] to

[18] .

[20] The host material described in

[19] for use with a delayed fluorescence material.

[21] A hole barrier material comprising one of the compounds described in [1] to

[18] .

[22] An organic light-emitting element comprising one of the compounds described in any one of [1] to

[18] .

[23] The organic light-emitting element according to

[22] , having a light-emitting layer containing the compound and a delayed fluorescence material.

[24] The organic light-emitting element according to

[22] or

[23] , wherein the light-emitting layer further comprises a host material not represented by the general formula (1).

[25] The organic light-emitting element according to

[24] , wherein the host material not represented by the general formula (1) has a structure represented by the following general formula (3). [ka] [In general formula (3), R 31 ~R 35 Each is independently selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group consisting of combinations thereof. 31 ~R 34 This is the other R 31 ~R 34 Although it does not bond with adjacent R to form a ring structure, 35 These elements may combine with each other to form a benzoflo or benzothieno skeleton. n31, n33, n34, and n35 each independently represent an integer from 0 to 4, and n32 represents an integer from 0 to 3.

[26] The organic light-emitting element according to

[22] , further comprising a layer containing the compound as a layer adjacent to the light-emitting layer. [Effects of the Invention]

[0007] By using the compounds of the present invention, it is possible to provide organic light-emitting devices with excellent properties. For example, organic light-emitting devices using the compounds of the present invention include organic electroluminescent devices with low driving voltages. [Modes for carrying out the invention]

[0008] The contents of the present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, numerical ranges represented by "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits.

[0009] (Compounds represented by general formula (1)) In this invention, a compound represented by the following general formula (1) is used. [ka]

[0010] In general formula (1), Z 1 is N or C(R11 ) represents Z 2 is N or C(R 12 ) represents. In one aspect of the present invention, Z 1 is C(R 11 ) and Z 2 is C(R 12 ) In one aspect of the present invention, Z 1 and Z 2 It is N. 1 and Z 2 They are preferably the same, but they may be different. R 1 ~R 12 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituents referred to here may be selected from, for example, groups A and substituents with a Hammett σp value of 0.3 or more, groups B and substituents with a Hammett σp value of 0.3 or more, groups C and substituents with a Hammett σp value of 0.3 or more, groups D and substituents with a Hammett σp value of 0.3 or more, or groups E and substituents with a Hammett σp value of 0.3 or more.

[0011] In this specification, "substituent group A" refers to a hydroxyl group, halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (e.g., C1-40), alkoxy group (e.g., C1-40), alkylthio group (e.g., C1-40), aryl group (e.g., C6-30), aryloxy group (e.g., C6-30), arylthio group (e.g., C6-30), heteroaryl group (e.g., ring skeleton constituent atoms number 5-30), heteroaryloxy group (e.g., ring skeleton constituent atoms number 5-30), heteroarylthio group (e.g., This refers to a group consisting of one or more groups selected from the group comprising the following: ring skeletons with 5 to 30 constituent atoms, acyl groups (e.g., 1 to 40 carbon atoms), alkenyl groups (e.g., 1 to 40 carbon atoms), alkynyl groups (e.g., 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups with 1 to 40 carbon atoms), and nitro groups, where some or all of the hydrogen atoms may be deuterium atoms. In this specification, "substituent group B" means one or more groups selected from the group consisting of alkyl groups (e.g., 1 to 40 carbon atoms), alkoxy groups (e.g., 1 to 40 carbon atoms), aryl groups (e.g., 6 to 30 carbon atoms), aryloxy groups (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 atoms in the ring skeleton), heteroaryloxy groups (e.g., 5 to 30 atoms in the ring skeleton), and diarylaminoamino groups (e.g., 0 to 20 carbon atoms), wherein some or all of the hydrogen atoms may be deuterium atoms. In this specification, "substituent group C" means one or more groups selected from the group consisting of alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton), and diarylamino groups (e.g., 12 to 20 carbon atoms), and the hydrogen atoms may be partially or entirely deuterium atoms. In this specification, "substituent group D" means one or more groups selected from the group consisting of alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), and heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton), and the hydrogen atoms may be partially or entirely deuterium atoms. In this specification, "substituent group E" means one or more groups selected from the group consisting of alkyl groups (e.g., C1 to C20) and aryl groups (e.g., C6 to C22), and the hydrogen atoms may be partially or entirely deuterium atoms. In this specification, when a substituent is described as "substituent" or "substituted or unsubstituted," it may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0012] "Hammett's σp value" was proposed by L.P. Hammett and quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, the following formula holds true between substituents and the reaction rate constant or equilibrium constant in para-substituted benzene derivatives: log(k / k0) = ρσp or log(K / K0) = ρσp This is a constant (σp) specific to the substituent in the above formula. In the above formula, k is the rate constant of the unsubstituted benzene derivative, k0 is the rate constant of the substituted benzene derivative, K is the equilibrium constant of the unsubstituted benzene derivative, K0 is the equilibrium constant of the substituted benzene derivative, and ρ is the reaction constant determined by the type and conditions of the reaction. For an explanation of "Hammett's σp value" in this invention and the numerical values ​​of each substituent, refer to the description of σp value in Hansch, C. et. al., Chem. Rev., 91, 165-195 (1991). Groups with a negative Hammett's σp value tend to exhibit electron-donating properties, while groups with a positive Hammett's σp value tend to exhibit electron-withdrawing properties. Groups with a Hammett σp value of 0.3 or higher include cyano groups, alkyl halides, and heteroaryl groups containing a nitrogen atom as a ring skeleton component. Preferably, these include cyano groups, alkyl fluorides, substituted or unsubstituted triazinyl groups, and substituted or unsubstituted pyrimidinyl groups. More preferably, these include cyano groups, perfluoroalkyl groups, and substituted or unsubstituted diaryltriazinyl groups. Even more preferably, these include cyano groups, trifluoromethyl groups, and diphenyltriazinyl groups. In one preferred embodiment of the present invention, a cyano group is used as the Hammett σp value of 0.3 or higher.

[0013] In general formula (1), R 1 and R 2 , R 2 and R 3 , R 3 and R 11 , R 12 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10These rings may bond to each other to form a cyclic structure. The cyclic structure formed by the bonding may be an aromatic ring or an antilipid ring, and may contain heteroatoms. Furthermore, the cyclic structure may be a fused ring of two or more rings. The heteroatoms here are preferably selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. Examples of the cyclic structures formed include benzene rings, naphthalene rings, pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, pyrrole rings, imidazole rings, pyrazole rings, imidazoline rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, cyclohexadiene rings, cyclohexene rings, cyclopentaene rings, cycloheptatriene rings, cycloheptadiene rings, cycloheptaene rings, furan rings, thiophene rings, naphthyridine rings, quinoxaline rings, and quinoline rings. For example, a ring formed by the fusion of multiple rings, such as a phenanthrene ring or a triphenylene ring, may be formed. A preferred example is a benzene ring. The hydrogen atoms in the formed cyclic structure may be substituted with deuterium atoms or substituents. Examples of substituents include R 1 ~R 12 You can refer to the description of the substituents and their preferred ranges. The number of rings formed by bonding to each other is preferably 1 to 5, more preferably 1 to 3, and may be, for example, 1 or 2. When the number of rings formed is 2 or more, rings may be formed at multiple locations, or polyrings may be formed at one location. In one embodiment of the present invention, R 7 and R 8 These are bonded to each other to form a cyclic structure (preferably a benzene ring). In a preferred embodiment of the present invention, R 7 and R 8 , R 9 and R 10 These elements are bonded to each other to form a cyclic structure (preferably a benzene ring). In general formula (1), Z 1 is C(R 11 ) and Z 2 is C(R 12 When R 11 and R 12They do not combine with each other to form a ring structure.

[0014] R in general formula (1) 1 ~R 12 At least one of them is a group represented by the following general formula (2). [ka]

[0015] In general formula (2), R 21 and R 22 Each of these independently represents a deuterium atom or a substituent. The substituents are R 1 ~R 12 You can refer to the description and preferred range of substituents. In one aspect of the present invention, R 21 and R 22 Each is independently selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group consisting of combinations thereof. In a preferred embodiment of the present invention, R 21 and R 22 Each of these is independently a deuterium atom, a C1-C4 alkyl group (preferably a methyl group or an ethyl group), or a phenyl group which may be further substituted with a phenyl group. In general formula (2), n1 represents an integer from 0 to 4, and n2 represents an integer from 0 to 3. In one aspect of the present invention, n1 is 0 or 1, and n2 is 0 or 1. In one aspect of the present invention, n1 + n2 is 1. In one aspect of the present invention, both n1 and n2 are 0. When n1 is 2 or greater and n2 is 2 or greater, adjacent R 21 Allies, adjacent R 22 They may be joined to each other to form a ring structure. In one preferred embodiment of the present invention, adjacent R 21 Allies, adjacent R 22 They are not connected to each other to form a ring structure. In general formula (2), Ar represents a substituted or unsubstituted arylene group. The aromatic ring constituting the arylene group has 1 to 20 carbon atoms, preferably 1 to 10, and more preferably 6. The substituents of the arylene group are R 1~R 12 You can refer to the description and preferred range of the substituents. In one aspect of the present invention, the substituent of the arylene group is selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group consisting of a combination thereof. In a preferred aspect of the present invention, the substituent of the arylene group is a deuterium atom, an alkyl group having 1 to 4 carbon atoms (preferably a methyl group or an ethyl group), or a phenyl group which may be substituted with a phenyl group, and more preferably a deuterium atom. The arylene group may also be unsubstituted. Preferred Ars include substituted or unsubstituted o-phenylene groups, substituted or unsubstituted m-phenylene groups, substituted or unsubstituted p-phenylene groups, substituted or unsubstituted naphthalene-1,8-diyl groups, substituted or unsubstituted naphthalene-1,5-diyl groups, substituted or unsubstituted naphthalene-2,6-diyl groups, and substituted or unsubstituted naphthalene-2,7-diyl groups, and a more preferred Ar is a substituted or unsubstituted phenylene group. In a preferred embodiment of the present invention, Ar is a substituted or unsubstituted m-phenylene group, for example, an unsubstituted m-phenylene group. In a preferred embodiment of the present invention, Ar is a substituted or unsubstituted p-phenylene group, for example, an unsubstituted p-phenylene group. In general formula (2), n3 is 0 or 1. In one aspect of the present invention, n3 is 1. In one aspect of the present invention, n3 is 0. In general formula (2), X is O, S, C(R 23 )(R 24 ) or N(R 25 ) represents R 23 and R 24 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 23 and R 24 They may be bonded to each other to form a cyclic structure (preferably a cycloalkyl ring which may be substituted with a deuterium atom or an alkyl group), R 25 represents a substituent. R is an example of a substituent. 1 ~R 12 You can refer to the description and preferred range of substituents. In one aspect of the present invention, R 23 and R 24Each is independently selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, and a group consisting of combinations thereof. In one aspect of the present invention, R 25 is an aryl group (preferably a phenyl group) which may be substituted with a deuterium atom or an alkyl group. In one aspect of the present invention, X is O, S or C(R 23 )(R 24 ) In one aspect of the present invention, X is O, S or N(R 25 ) In one aspect of the present invention, X is O or S, preferably O. In one aspect of the present invention, X is C(R 23 )(R 24 ) In one aspect of the present invention, X is N(R 25 ) In general formula (2), R 23 ~R 25 One of the following and R 21 They do not combine with each other to form a ring structure, R 23 ~R 25 One of the following and R 22 They do not combine with each other to form a ring structure, R 22 The substituents that substitute for the arylene group of Ar do not bond to each other to form a cyclic structure. In general formula (2), * represents the bond position.

[0016] In one aspect of the present invention, X in general formula (2) is O or S, and R 21 and R 22 Each of these is independently selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group consisting of combinations thereof, n3 is 1, and Ar is a phenylene group which may be substituted with a deuterium atom. In one aspect of the present invention, X in general formula (2) is O or S, and R 21 and R 22 is a deuterium atom, Ar is a phenylene group which may be substituted with a deuterium atom, and n3 is 1. In one aspect of the present invention, X in general formula (2) is O or S, and R 21 and R 22Each of these is independently selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group consisting of a combination thereof, and n3 is 0. In one aspect of the present invention, X in general formula (2) is O or S, and R 21 and R 22 This is a deuterium atom, and n3 is 0.

[0017] In one preferred embodiment of the present invention, the group represented by general formula (2) has a structure represented by the following general formula (2a). [ka]

[0018] In general formula (2a), R 21 and R 22 Each of the following independently represents a deuterium atom or substituent, and Ar represents a substituted or unsubstituted arylene group. n1 represents an integer from 0 to 4, n2 represents an integer from 0 to 3, and n3 represents 0 or 1. Adjacent R 21 Allies, adjacent R 22 They may be bonded to each other to form a ring structure. X is O, S, C(R 23 )(R 24 ) or N(R 25 ) represents R 23 and R 24 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 25 * represents a substituent. * represents a bond position. X, R 21 ~R 25 For explanations of Ar, n1 to n3 and their preferred ranges, refer to the corresponding description in general formula (2).

[0019] Specific examples of the group represented by general formula (2) are given below. However, the group represented by general formula (2) that can be used in the present invention is not limited to these specific examples. Note that the CH3 notation is omitted for the methyl group. For example, X65 to X80 represent structures in which the benzene ring constituting the dibenzofuryl group is substituted with a methyl group. [ka] JPEG0007899981000011.jpg202170JPEG0007899981000012.jpg234170JPEG0007899981000013.jpg222170JPEG0007899981000014.jpg213170 JPEG0007899981000015.jpg242170JPEG0007899981000016.jpg213167JPEG0007899981000017.jpg225162JPEG0007899981000018.jpg122169

[0020] X1 to X120 are specific examples of groups in general formula (2) where X is O. The groups obtained by substituting O with S in X1 to X120 are shown here as X121 to X240, respectively. The groups obtained by substituting O with C(CH3)2 in X1 to X120 are shown here as X241 to X360, respectively. The groups obtained by substituting O with C(C6H5)2 in X1 to X120 are shown here as X361 to X480, respectively. The groups obtained by substituting O with N(C6H5) in X1 to X120 are shown here as X481 to X600, respectively. The groups obtained by substituting all hydrogen atoms in X1 to X600 with deuterium atoms are shown here as X1(D) to X600(D), respectively. Furthermore, the groups obtained by substituting all hydrogen atoms in the phenyl, biphenylyl, and methyl substituents of X5 to X80, X85 to X100, X105 to X120, X125 to X200, X205 to X220, X225 to X240, X245 to X320, X325 to X340, X345 to X360, X365 to X440, X445 to X460, X465 to X480, X485 to X560, X565 to X580, and X585 to X600 with deuterium atoms are shown here as X5(d) to X80(d), X85(d), and X100, respectively. (d) is exemplified here as X105(d)~X120(d), X125(d)~X200(d), X205(d)~X220(d), X225(d)~X240(d), X245(d)~X320(d), X325(d)~X340(d), X345(d)~X360(d), X365(d)~X440(d), X445(d)~X460(d), X465(d)~X480(d), X485(d)~X560(d), X565(d)~X580(d), and X585(d)~X600(d).

[0021] In one aspect of the present invention, R 1 ~R 12 One to four of these are groups represented by general formula (2), preferably one or two are groups represented by general formula (2). In one aspect of the present invention, R 1 Only is the group represented by general formula (2). In one aspect of the present invention, R 2 Only is the group represented by general formula (2). In one preferred embodiment of the present invention, R 3 Only is the group represented by general formula (2). In one aspect of the present invention, R 11 Only is the group represented by general formula (2). In one aspect of the present invention, R 9 Only is the group represented by general formula (2). In one aspect of the present invention, R 10 Only this is a base represented by general formula (2). In one aspect of the present invention, R 1 and R 6 Only is the group represented by general formula (2). In one aspect of the present invention, R 2 and R5 Only is the group represented by general formula (2). In one preferred embodiment of the present invention, R 3 and R 4 Only is the group represented by general formula (2). In one aspect of the present invention, R 11 and R 12 Only is the group represented by general formula (2). In one aspect of the present invention, R 8 and R 9 Only is the group represented by general formula (2). In one aspect of the present invention, R 7 and R 10 Only is the group represented by general formula (2). In one aspect of the present invention, R 1 ~R 12 When two or more of these groups are represented by general formula (2), the structures of those groups are identical.

[0022] In one aspect of the present invention, R 1 ~R 12 Each of these is independently a hydrogen atom, a deuterium atom, a group represented by general formula (2), an aryl group (preferably a phenyl group), an alkyl group (preferably a methyl group), or a group with a Hammett σp of 0.3 or more (preferably a cyano group). In one aspect of the present invention, R 1 ~R 12 Each of these is independently a hydrogen atom, a deuterium atom, a group represented by general formula (2), a phenyl group, or a group with a Hammett σp of 0.3 or more (preferably a cyano group). In one aspect of the present invention, R 1 ~R 12 Except for the group represented by general formula (2), the other elements are hydrogen atoms or deuterium atoms. In one aspect of the present invention, R 7 and R 8 , R 9 and R 10 These are bonded to each other to form a cyclic structure (preferably a benzene ring), R 1 ~R 6 , R 11 , R 12 Except for the group represented by general formula (2), R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 7 and R 8 , R 9 and R 10These are bonded to each other to form a cyclic structure (preferably a benzene ring), and this cyclic structure is substituted with a group (preferably a cyano group) with a Hammett σp of 0.3 or more, R 1 ~R 6 , R 11 , R 12 Except for the group represented by general formula (2), the other elements are hydrogen atoms or deuterium atoms. In one aspect of the present invention, the compound represented by general formula (1) does not have a cyano group. In one aspect of the present invention, the compound represented by general formula (1) has one or two cyano groups. For example, it has one cyano group. For example, it has two cyano groups.

[0023] R in general formula (1) 7 and R 8 , R 9 and R 10 When these elements are bonded to each other to form a ring structure, it is preferable that they have a structure represented by the following general formula (1a). [ka]

[0024] In general formula (1a), Z 1 is N or C(R 11 ) represents Z 2 is N or C(R 12 ) represents Z 3 is N or C(R 19 ) represents Z 4 is N or C(R 20 ) represents R 1 ~R 6 , R 11 ~R 20 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 2 , R 2 and R 3 , R 3 and R 11 , R 12 and R 4 , R 4 and R 5 , R 5 and R 6 , R13 and R 14 , R 14 and R 15 , R 15 and R 19 , R 20 and R 16 , R 16 and R 17 , R 17 and R 18 They may be bonded to each other to form a ring structure, 11 and R 12 They do not combine with each other to form a ring structure, R 19 and R 20 They do not combine with each other to form a ring structure. However, R 1 ~R 6 , R 11 , R 12 At least one of them is a group represented by general formula (2). R 13 ~R 20 , Z 3 , Z 4 For an explanation and preferred range, see R in general formula (1). 1 ~R 12 , Z 1 , Z 2 You can refer to the corresponding description.

[0025] In this application, the "alkyl group" may be linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched portions may be mixed. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group. In one aspect of the present invention, the number of carbon atoms in the alkyl group is 1 to 4. In one aspect of the present invention, the alkyl group is a methyl group. In one aspect of the present invention, the alkyl group is an isopropyl group. In one aspect of the present invention, the alkyl group is a tert-butyl group. When multiple alkyl groups exist in a molecule represented by general formula (1), these alkyl groups may be identical or different. In one aspect of the present invention, all alkyl groups in the molecule represented by general formula (1) are identical. The number of alkyl groups in the molecule represented by general formula (1) can be 0 or more, 1 or more, 2 or more, 4 or more, or 8 or more. The number of alkyl groups in the molecule represented by general formula (1) may be 20 or less, 10 or less, 5 or less, or 3 or less. The number of alkyl groups in the molecule represented by general formula (1) may be 0. The "aryl group" may be a monoring or a fused ring formed by the fusion of two or more rings. When it is a monoring, the aryl group is a phenyl group. When it is a fused ring, the aryl group is a group formed by the fusion of a phenyl group with one or more additional rings. The ring fused to the phenyl group may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a ring formed by the fusion of these. Preferably, it is an aromatic hydrocarbon ring. A benzene ring can be given as an example of an aromatic hydrocarbon ring. The benzene ring may have other benzene rings fused to it. Specific examples of aryl groups include the phenyl group, the naphthalene-1-yl group, and the naphthalene-2-yl group. These specific examples may be substituted.

[0026] The compound represented by general formula (1) does not contain any metal elements. In one aspect of the present invention, the compound represented by general formula (1) consists only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In one aspect of the present invention, the compound represented by general formula (1) consists only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, and even more preferably 1000 or less. For example, it may be selected within the range of 800 or less. The lower limit of the molecular weight is the minimum molecular weight of the structure represented by general formula (1). The compound represented by general formula (1) may be a symmetric compound. In one aspect of the present invention, the compound represented by general formula (1) is a line-symmetric compound. In one aspect of the present invention, the compound represented by general formula (1) is an asymmetric compound.

[0027] Specific examples of compounds represented by general formula (1) are shown below. However, the group represented by general formula (1) that can be used in the present invention is not limited to these specific examples. First, specific examples of compounds having the structure represented by the following general formula (1b) are shown. In Table 1, the R of each compound is shown. 1 ~R 12 By identifying the atoms or groups, the structure of each compound from 1 to 600 is determined. [ka] [Table 1] JPEG0007899981000022.jpg255158JPEG0007899981000023.jpg255160

[0028] In Table 2, R 1 ~R 12 The structures of compounds 1 to 26400 are identified by identifying the atoms or groups. In the row for compounds 1 to 600 in Table 2, R2 ~R 12 The hydrogen atom (H) is fixed, and R 1 The structures of 600 compounds are sequentially identified by changing X1 to X600. Compounds 1 to 600 in Table 2 are the same as those identified in Compounds 1 to 600 in Table 1. In the row for compounds 601 to 1200 in Table 2, R 1 , R 3 ~R 12 The hydrogen atom (H) is fixed, and R 2 The structures of 600 compounds are sequentially identified by changing X1 to X600. In the row for compounds 1201 to 1800 in Table 2, R 1 , R 2 , R 4 ~R 12 The hydrogen atom (H) is fixed, and R 3 The structures of 600 compounds are sequentially identified by changing X1 to X600. In the row for compounds 1801 to 2400 in Table 2, R 1 ~R 10 , R 12 The hydrogen atom (H) is fixed, and R 11 The structures of 600 compounds are sequentially identified by changing X1 to X600. In the row for compounds 2401 to 3000 in Table 2, R 2 ~R 5 , R 7 ~R 12 The hydrogen atom (H) is fixed, and R 1 and R 6 The structures of 600 compounds are sequentially identified by simultaneously changing X1 to X600 (R 1 and R 6 (This is always the same structural basis). The structure is identified in the same way in each row of Table 2 thereafter. Tables 3-5 show the structures of each compound represented by the general formulas (1c), (1d), and (1e), respectively, in the same manner as in Table 2. [Table 2] JPEG0007899981000025.jpg255123 [Table 3] JPEG0007899981000027.jpg249170 [Table 4] [Table 5]

[0029] Compounds obtained by substituting all hydrogen atoms in compounds 1 to 50400 with deuterium atoms are shown here as compounds 1(D) to 50400(D), respectively. Furthermore, compounds obtained by substituting all hydrogen atoms in the group represented by general formula (2) of compounds 1 to 50400 with deuterium atoms are shown here as compounds 1(d) to 50400(d), respectively. In one aspect of the present invention, a compound is selected from compounds 1 to 26400, compounds 1(D) to 26400(D), and compounds 1(d) to 26400(d). In one aspect of the present invention, a compound is selected from compounds 26401 to 43200, compounds 26401(D) to 43200(D), and compounds 26401(d) to 43200(d). In one aspect of the present invention, a compound is selected from compounds 43201 to 45600, compounds 43201(D) to 45600(D), and compounds 43201(d) to 45600(d). In one aspect of the present invention, a compound is selected from compounds 45601 to 50400, compounds 45601(D) to 50400(D), and compounds 45601(d) to 50400(d).

[0030] The compound represented by general formula (1) is useful as a host material for doping luminescent materials. It is particularly useful as a host material for doping delayed fluorescence materials. The doping material may be one type or more types. The doping material should be selected from those with a lower minimum excitation singlet energy than the compound represented by general formula (1). Compounds represented by general formula (1) are also useful as carrier barrier materials, for example, as hole barrier materials. They can be effectively used as barrier layers (e.g., hole barrier layers) in organic light-emitting devices such as organic electroluminescent elements.

[0031] (Delayed fluorescence materials) Compounds represented by general formula (1) are useful as host materials for use with delayed fluorescence materials. In this context, a "delayed fluorescence material" refers to an organic compound that, in its excited state, undergoes a reverse intersystem crossover from an excited triplet state to an excited singlet state, and emits delayed fluorescence when returning from that excited singlet state to the ground state. In this invention, a delayed fluorescence material is defined as one in which fluorescence with an emission lifetime of 100 ns (nanoseconds) or longer is observed when measured using a fluorescence lifetime measurement system (such as the Hamamatsu Photonics Streak Camera System). When a compound represented by general formula (1) is used in combination with a delayed fluorescence material, the delayed fluorescence material receives energy from the compound represented by general formula (1) in an excited singlet state and transitions to an excited singlet state. Alternatively, the delayed fluorescence material may receive energy from the compound represented by general formula (1) in an excited triplet state and transition to an excited triplet state. The delayed fluorescence material is the difference between the excited singlet energy and the excited triplet energy (ΔE ST Because the ) is small, excited triplet state delayed fluorescence material readily crosses back into excited singlet state delayed fluorescence material. The excited singlet state delayed fluorescence material generated by these pathways contributes to the emission.

[0032] The delayed fluorescence material is the difference ΔE between the lowest excitation singlet energy and the lowest excitation triplet energy at 77K. ST It is preferable that the voltage is 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. ΔE STIf the thermal energy absorption is small, the reverse intersystem crossover from the excited singlet state to the excited triplet state is more likely to occur, thus functioning as a thermally activated delayed fluorescence material. Thermally activated delayed fluorescence materials absorb the heat emitted by the device and relatively easily reverse intersystem crossover from the excited triplet state to the excited singlet state, and can efficiently contribute that excited triplet energy to luminescence.

[0033] In the present invention, the lowest excitation singlet energy (E) of the compound S1 ) and the lowest excited triplet energy (E T1 ) is the value obtained by the following procedure: ΔE ST is E S1 -E T1 This is the value obtained by calculation. (1) Lowest excitation singlet energy (E S1 ) A thin film or toluene solution of the compound to be measured (concentration 10%) -5 Prepare a sample (mol / L). Measure the fluorescence spectrum of this sample at room temperature (300K). The fluorescence spectrum has emission on the vertical axis and wavelength on the horizontal axis. Draw a tangent to the rising edge of the short-wave side of the emission spectrum, and determine the wavelength value λedge [nm] at the intersection of this tangent and the horizontal axis. Convert this wavelength value to an energy value using the following conversion formula: E S1 Let's assume that. Conversion formula: E S1 [eV]=1239.85 / λedge In the examples described below, the emission spectra were measured using an LED light source (Thorlabs, M300L4) as the excitation light source and a detector (Hamamatsu Photonics, PMA-12 multi-channel spectrometer C10027-01). (2) Lowest excited triplet energy (E T1 ) Lowest excitation singlet energy (E S1The same sample used in the measurement is cooled to 77[K] with liquid nitrogen, and excitation light (300 nm) is irradiated onto the phosphorescence measurement sample. Phosphorescence is measured using a detector. The emission from 100 milliseconds after excitation light irradiation is taken as the phosphorescence spectrum. A tangent line is drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the wavelength value λedge[nm] at the intersection of this tangent line and the horizontal axis is determined. This wavelength value is converted to an energy value using the following conversion formula E T1 Let's assume that. Conversion formula: E T1 [eV]=1239.85 / λedge The tangent to the rise of the phosphorescence spectrum on the short-wavelength side is drawn as follows: When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum is taken as the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 10% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side.

[0034] In this invention, known delayed fluorescence materials can be used in appropriate combinations with compounds represented by general formula (1). Furthermore, even unknown delayed fluorescence materials can be used. As delayed fluorescence materials, paragraphs 0008-0048 and 0095-0133 of Publication No. WO2013 / 154064, paragraphs 0007-0047 and 0073-0085 of Publication No. WO2013 / 011954, paragraphs 0007-0033 and 0059-0066 of Publication No. WO2013 / 011955, and paragraphs 0008-007 of Publication No. WO2013 / 081088 Paragraphs 1 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of Japanese Patent Publication No. 2013-256490, paragraphs 0008~0020 and 0038~0040 of Japanese Patent Publication No. 2013-116975, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359, paragraph 0008~ Paragraphs 0054 and 0101-0121, paragraphs 0007-0041 and 0060-0069 of JP 2014-9352, paragraphs 0008-0048 and 0067-0076 of JP 2014-9224, paragraphs 0013-0025 of JP 2017-119663, paragraphs 0013-0026 of JP 2017-119664, JP 2017- Examples include compounds included in the general formulas described in paragraphs 0012-0025 of Japanese Patent Publication No. 222623, paragraphs 0010-0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012-0043 of Japanese Patent Application Publication No. 2018-100411, and paragraphs 0016-0044 of Japanese Patent Application Publication No. WO2018 / 047853, particularly exemplary compounds that emit delayed fluorescence.Also, Japanese Patent Publication No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO2014 / 136860, WO20 14 / 196585 publication, WO2014 / 189122 publication, WO2014 / 168101 publication, WO2015 / 008580 publication, WO2014 / 203840 publication , WO2015 / 002213, WO2015 / 016200, WO2015 / 019725, WO2015 / 072470, WO2015 / 1080 Publication No. 49, Publication No. WO2015 / 080182, Publication No. WO2015 / 072537, Publication No. WO2015 / 080183, JP Publication No. 2015-129240, Publication No. WO2015 / 129714, Publication No. WO2015 / 129715, Publication No. WO2015 / 133501, Publication No. WO2015 / 136880, Publication No. WO2015 / 137244, W Light-emitting materials that emit delayed fluorescence, as described in sections

[0028] to

[0056] of Publication O2015 / 137202, Publication WO2015 / 137136, Publication WO2015 / 146541, Publication WO2015 / 159541, and sections

[0028] to

[0056] of Publication WO2020 / 111205, and pages 62 to 159 of Publication WO2019 / 191665, can also be used. The above publications described in this paragraph are incorporated herein by reference as part of this specification.

[0035] The delayed fluorescence material used in the present invention preferably does not contain metal atoms. For example, a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected as the delayed fluorescence material. For example, a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms can be selected as the delayed fluorescence material. For example, a compound consisting of carbon atoms, hydrogen atoms, and nitrogen atoms can be selected as the delayed fluorescence material. In one aspect of the present invention, a compound having a phenazine skeleton, preferably a compound having a dibenzo[a,c]phenazine skeleton, is used as a delayed fluorescence material.

[0036] (composition) The present invention also provides compositions comprising a compound represented by general formula (1) and a delayed fluorescence material. In one aspect of the present invention, the composition comprises only one or more compounds represented by general formula (1) and one or more delayed fluorescence materials. In one aspect of the present invention, the composition comprises only one compound represented by general formula (1) and one delayed fluorescence material. In one aspect of the present invention, the composition comprises a third component in addition to the compound represented by general formula (1) and the delayed fluorescence material. The third component here is neither a compound represented by general formula (1) nor a delayed fluorescence material. For example, the third component may be a host material not represented by general formula (1) or a fluorescent material that does not emit delayed fluorescence. The third component may consist of only one type or two or more types. If the third component in the composition is not a host material, the content of the third component may be selected within the range of 30% by mass or less, 10% by mass or less, 1% by mass or less, or 0.1% by mass or less. If the third component in the composition is a host material, the content of the third component may be selected within the range of 80% by mass or less, 60% by mass or less, 1% by mass or more, 10% by mass or more, or 20% by mass or more. In one preferred embodiment of the present invention, the dominant component of the emission from the composition of the present invention is fluorescence (including delayed fluorescence). In the composition of the present invention, the compound represented by general formula (1) is present in a greater amount by mass than the delayed fluorescence material. The content of the compound represented by general formula (1) may be selected within a range of 3 times or more by mass of the content of the delayed fluorescence material, or within a range of 10 times or more by mass. Alternatively, it may be selected within a range of, for example, 10,000 times or less by mass, or within a range of 1,000 times or less by mass. In the compositions of the present invention, it is preferable to select a delayed fluorescence material having an excitation singlet energy smaller than the excitation singlet energy of the compound represented by general formula (1). The difference in excitation singlet energy may be 0.1 eV or more, 0.3 eV or more, 0.5 eV or more, 2 eV or less, 1.5 eV or less, or 1.0 eV or less. The compositions of the present invention preferably do not contain metallic elements. In one aspect of the present invention, the compositions of the present invention consist only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms, and halogen atoms. In one aspect of the present invention, the compositions of the present invention consist only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

[0037] Furthermore, in one aspect of the present invention, the compound represented by general formula (1) is useful as a host material for use together with a delayed fluorescence material and a fluorescent compound. For this reason, in one aspect of the present invention, the composition of the present invention includes a fluorescent compound in addition to the compound represented by general formula (1) and the delayed fluorescence material.

[0038] Fluorescent compounds have a lower excitation singlet energy (E) than compounds represented by general formula (1) and delayed fluorescence materials. S1 It is preferable that the ) is small. The fluorescent compound receives energy from the compound represented by general formula (1) in the excited singlet state and the delayed fluorescent material, and from the delayed fluorescent material which has crossed from the excited triplet state to the excited singlet state via reverse intersystem crossing, and then emits fluorescence when it returns to the ground state. The fluorescent compound is not particularly limited as long as it can receive energy from the compound represented by general formula (1) and the delayed fluorescent material and emit fluorescence, and the emission may be either fluorescence or delayed fluorescence. In particular, it is preferable that the emitter used as the fluorescent compound emits fluorescence when it returns from the lowest excited singlet energy level to the ground energy level. Two or more types of fluorescent compounds may be used. For example, by using two or more fluorescent compounds with different emission colors in combination, it is possible to emit a desired color. As fluorescent compounds, it is possible to use compounds that exhibit multiple resonance effects, such as anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluorantene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, duroridine derivatives, thiazole derivatives, derivatives containing metals (Al,Zn), and compounds having a boron-containing polycyclic aromatic skeleton such as diazabora naphthanothracene. These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons may be combined with each other.

[0039] Specific examples of fluorescent compounds include those listed as specific examples of delayed fluorescence materials. In this case, the composition of the present invention will contain two or more delayed fluorescence materials, with the one having a higher minimum excitation singlet energy functioning as an assist dopant, and the one having a lower minimum excitation singlet energy functioning primarily as a fluorescent compound that emits light. The compound used as the fluorescent compound preferably exhibits a PL emission quantum yield of 60% or more, and more preferably 80% or more. Furthermore, the compound used as the fluorescent compound preferably exhibits an instantaneous fluorescence lifetime of 50 ns or less, and more preferably 20 ns or less. The instantaneous fluorescence lifetime in this case refers to the emission lifetime of the component that decays the fastest among multiple exponential decay components observed when emission lifetime measurements are performed on a compound exhibiting thermally activated delayed fluorescence. Furthermore, the compound used as the third compound preferably has a fluorescence emission rate from the minimum excitation singlet (S1) to the ground state that is greater than the intersystem crossover rate from S1 to the minimum excitation triplet (T1). For information on how to calculate the rate constant of a compound, refer to known literature on thermally activated delayed fluorescence materials (e.g., H. Uoyama, et al., Nature 492, 234 (2012) and K. Masui, et al., Org. Electron. 14, 2721, (2013)).

[0040] The following are some preferred compounds that can be used as fluorescent compounds in combination with delayed fluorescence materials, but the fluorescent compounds that can be used in the present invention are not limited to these specific examples.

[0041] [ka] JPEG0007899981000031.jpg237170JPEG0007899981000032.jpg157170

[0042] Furthermore, the compounds described in paragraphs 0220-0239 of Publication No. WO2015 / 022974 can also be particularly preferred as fluorescent compounds of the present invention.

[0043] Furthermore, in one aspect of the present invention, the compound represented by general formula (1) can be used together with other host materials to form a light-emitting layer (composition) containing multiple host materials. That is, in one aspect of the present invention, the composition of the present invention contains a host material represented by general formula (1) and a host material not represented by general formula (1). Examples of host materials not represented by general formula (1) include compounds represented by the following general formula (3). [ka]

[0044] In general formula (3), R 31 ~R 35 Each is independently selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group consisting of combinations thereof. 31 ~R 34 This is the other R 31 ~R 34 Although it does not bond with adjacent R to form a ring structure, 35 These elements may combine with each other to form a benzoflo or benzothieno skeleton (condensed via a furan or thiophene ring). n31, n33, n34, and n35 each independently represent an integer from 0 to 4, and n32 represents an integer from 0 to 3. For descriptions of alkyl groups and aryl groups and their preferred ranges, refer to the above description of alkyl groups and aryl groups and their preferred ranges. In one aspect of the present invention, R 31 ~R 35 Each of these is independently a deuterium atom, a methyl group, a phenyl group, an o-biphenylyl group, an m-biphenylyl group, or a p-biphenylyl group. In one aspect of the present invention, R 31 ~R 35 Each of these is independently a deuterium atom, a phenyl group, an o-biphenylyl group, an m-biphenylyl group, or a p-biphenylyl group. In one aspect of the present invention, R 31 ~R 35is a deuterium atom. In one aspect of the present invention, n31 to n35 are each independently integers from 0 to 2, for example 0 or 1. In one aspect of the present invention, the sum of n31 to n35 is from 0 to 5, for example 0 to 3, for example 0 to 2, for example 0, for example 1, for example 2. In general formula (3), (R 33 ) n33 The dibenzoplan ring is preferably bonded at the meta or para position to the carbazole ring bonded to the central benzene ring to which the compound is bonded, and more preferably at the meta position.

[0045] In general formula (3), adjacent R 35 Compounds in which these elements are bonded to each other to form a benzoflo or benzothieno skeleton are shown in the following general formula (3a). [ka]

[0046] In general formula (3a), R 31 ~R 36 Each is independently selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group consisting of combinations thereof. 31 ~R 36 This is the other R 31 ~R 36 It does not combine with other elements to form a cyclic structure. n31, n33, n34, and n36 each independently represent an integer from 0 to 4, n32 represents an integer from 0 to 3, and n35 represents an integer from 0 to 2. X represents O, S, or N(R). R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0047] In the following, the general formula (3) (R 33 ) n33 Specific examples of groups having a carbazole ring bonded to a central benzene ring are given. However, these examples do not mean that groups having a carbazole ring should be interpreted restrictively. [ka] JPEG0007899981000036.jpg233170JPEG0007899981000037.jpg222170JPEG0007899981000038.jpg242170JPEG0007899981000039.jpg196170 JPEG0007899981000040.jpg216170JPEG0007899981000041.jpg248170JPEG0007899981000042.jpg235170JPEG0007899981000043.jpg204170

[0048] (R) of general formula (3) 33 ) n33 Specific examples of groups having a dibenzofuran ring bonded to a central benzene ring to which is bonded include X3, X7, X11, X15, X19, X22, X26, X30, X34, X37, X41, X45, X49, X52, X56, X60, X64, X67, X71, X75, and X79. However, these specific examples do not mean that groups having a dibenzofuran ring are interpreted restrictively.

[0049] Specific examples of compounds represented by general formula (3) are shown below. However, the compounds represented by general formula (3) that can be used in the present invention are not limited to these specific examples. First, let's look at specific examples of compounds having the structure represented by general formula (3b). In Table 6, the structures of H1 to H238 are identified by specifying the atoms or groups X and D of each compound. [ka] [Table 6]

[0050] In Table 7, the structures of H1 to H2499 are identified by identifying the atoms or groups of X and D. In the H1 to H119 section of Table 7, the structures of 119 compounds are sequentially identified by fixing X to X3 and changing D to D1 to D119. The H1 to H119 in Table 7 are the same as those identified in Table 6. In the H120 to H238 section of Table 7, the structures of 119 compounds are sequentially identified by fixing X to X7 and changing D to D1 to D119. The structures of each subsequent section of Table 7 are identified in the same manner. Table 8 identifies the structure of each compound represented by general formula (3c) in the same manner as in Table 7. [Table 7] [Table 8]

[0051] Compounds in which all hydrogen atoms from H1 to H4998 are replaced with deuterium atoms are exemplified here, denoted as H1(D) to H4998(D), respectively.

[0052] The form of the composition of the present invention is not particularly limited. In one particularly preferred embodiment of the present invention, the composition of the present invention is in the form of a film. The film made of the composition of the present invention may be formed by a wet process or by a dry process. In the wet process, a solution containing the composition of the present invention is applied to a surface, and a light-emitting layer is formed after the solvent is removed. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, a suitable organic solvent capable of dissolving the composition of the present invention is selected and used. In some embodiments, substituents (e.g., alkyl groups) that increase solubility in organic solvents can be introduced into the compounds contained in the composition of the present invention. As a dry process, vacuum deposition can be preferably employed. When using vacuum deposition, each compound constituting the composition of the present invention may be co-deposited from an individual deposition source, or all compounds may be co-deposited from a single deposition source containing a mixture. When using a single deposition source, a mixed powder containing the powders of all compounds may be used, a compressed molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating, melting, mixing, and then cooling each compound may be used. In one embodiment, by performing co-deposition under conditions where the deposition rates (mass loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, a film with a composition ratio corresponding to the composition ratio of multiple compounds contained in the deposition source can be formed. By mixing multiple compounds in the same composition ratio as the composition ratio of the formed film to create a deposition source, a film with a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-deposited compound has the same mass loss rate can be identified, and that temperature can be adopted as the temperature during co-deposition. When the film is formed by vapor deposition, the molecular weight of each compound constituting the composition 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 may be, for example, 450, 500, or 600.

[0053] (Organic light-emitting device) By forming a light-emitting layer made from the composition of the present invention, excellent organic light-emitting elements such as organic photoluminescent elements (organic PL elements) and organic electroluminescent elements (organic EL elements) can be provided. The organic light-emitting element of the present invention is a fluorescent light-emitting element, and the largest component of light emitted from the element is fluorescence (fluorescence here includes delayed fluorescence). The thickness of the light-emitting layer can be, for example, 1-15 nm, 2-10 nm, or 3-7 nm. Organic photoluminescent elements have a structure in which at least a light-emitting layer is formed on a substrate. Organic electroluminescent elements have a structure in which at least an anode, a cathode, and an organic layer are formed between the anode and the cathode. The organic layer includes at least a light-emitting layer, and may consist only of a light-emitting layer, or it may have one or more organic layers in addition to the light-emitting layer. Examples of other such organic layers include hole transport layers, hole injection layers, electron barrier layers, electron injection layers, electron transport layers, and exciton barrier layers. The hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function. When the organic light-emitting element of the present invention is a multi-wavelength emitting organic light-emitting element, the shortest wavelength emission may include delayed fluorescence. Alternatively, the shortest wavelength emission may not include delayed fluorescence. An organic light-emitting element using the composition of the present invention can emit light in the ultraviolet region, the blue, green, yellow, orange, and red regions of the visible spectrum (e.g., 420-500 nm, 500-600 nm, or 600-700 nm), or the near-infrared region when excited by thermal or electronic means. For example, an organic light-emitting element can emit light in the red or orange region (e.g., 620-780 nm). For example, an organic light-emitting element can emit light in the orange or yellow region (e.g., 570-620 nm). For example, an organic light-emitting element can emit light in the green region (e.g., 490-575 nm). For example, an organic light-emitting element can emit light in the blue region (e.g., 400-490 nm). For example, an organic light-emitting element can emit light in the ultraviolet spectral region (e.g., 280-400 nm). For example, an organic light-emitting element can emit light in the infrared spectral region (e.g., 780 nm to 2 μm). The most abundant component of the light emitted from an organic light-emitting element using the composition of the present invention is preferably the light emitted from the delayed fluorescence material contained in the composition of the present invention. The light emitted from the compound represented by general formula (1) is preferably less than 10% of the light emitted from the organic light-emitting element, and may be, for example, less than 1%, less than 0.1%, less than 0.01%, or below the detection limit. The light emitted from the delayed fluorescence material may be, for example, more than 50%, more than 90%, or more than 99% of the light emitted from the organic light-emitting element. If the layer containing the composition of the present invention (light-emitting layer) contains a fluorescent material as a third component, the most abundant component of the light emitted from the organic light-emitting element may be the light emitted from that fluorescent material. In that case, the light emitted from the light-emitting material may be, for example, more than 50%, more than 90%, or more than 99% of the light emitted from the organic light-emitting element.

[0054] The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer.

[0055] Base material: In some embodiments, the organic electroluminescent element of the present invention is held by a substrate, which is not particularly limited and may be any of the materials commonly used in organic electroluminescent elements, such as glass, transparent plastic, quartz, and silicon.

[0056] anode: In some embodiments, the anode of an organic electroluminescent apparatus is manufactured from a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is manufactured by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, if the pattern does not need to be highly precise (e.g., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, wet film formation methods such as printing or coating methods are used. In some embodiments, when synchrotron radiation passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0057] 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-injection metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of the electron-injection metal and a second metal that is a stable metal having a higher work function than the electron-injection metal is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injection properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by vapor deposition or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the cathode is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, either the anode or cathode of the organic electroluminescent element is transparent or translucent in order to transmit synchrotron radiation. In some embodiments, a transparent or translucent electroluminescent element enhances the light radiance. In some embodiments, a transparent or translucent cathode is formed by forming the cathode with respect to the conductive transparent material described above. In some embodiments, the element includes an anode and a cathode, both of which are transparent or translucent.

[0058] Injection layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be located between the anode and the light-emitting layer or hole transport layer, and between the cathode and the light-emitting layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is absent. The following are examples of preferred compounds that can be used as hole injection materials.

[0059] [ka]

[0060] Next, we will list some examples of preferred compounds that can be used as electron injection materials. [ka]

[0061] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing to the outside of the light-emitting layer. In some embodiments, an electron barrier layer exists between the light-emitting layer and the hole transport layer, preventing electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole barrier layer exists between the light-emitting layer and the electron transport layer, preventing holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing to the outside of the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. As used herein, the terms “electron barrier layer” or “exciton barrier layer” include layers that have both the functions of an electron barrier layer and an exciton barrier layer.

[0062] Hole barrier layer: The positive hole blocking layer functions as an electron transport layer. In some embodiments, during the transport of electrons, the positive hole blocking layer prevents holes from reaching the electron transport layer. In some embodiments, the positive hole blocking layer increases the probability of recombination of electrons and holes in the light emitting layer. The material used for the positive hole blocking layer may be the same as that described above for the electron transport layer. In one aspect of the present invention, a compound represented by the general formula (1) is used as a positive hole blocking material in the positive hole blocking layer. Examples of preferable compounds that can be used for the positive hole blocking layer are given below.

[0063]

Chemical Formula

[0064] Electron blocking layer: The electron blocking layer transports holes. In some embodiments, during the transport of holes, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light emitting layer. The material used for the electron blocking layer may be the same as that described above for the hole transport layer. Specific examples of preferable compounds that can be used as electron blocking materials are given below.

[0065]

Chemical Formula

[0066] Exciton blocking layer: The exciton barrier layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton barrier layer enables effective confinement of excitons in the light-emitting layer. In some embodiments, the optical emission efficiency of the device is improved. In some embodiments, the exciton barrier layer is located on either the anode side or the cathode side and adjacent to the light-emitting layers on both sides. In some embodiments, when the exciton barrier layer is located on the anode side, it may be located between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton barrier layer is located on the cathode side, it may be located between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, electron barrier layer, or similar layer is located between the anode and the exciton barrier layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, electron barrier layer, hole barrier layer, or similar layer is located between the cathode and the exciton barrier layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton barrier layer includes an excitation singlet energy and an excitation triplet energy, at least one of which is higher than the excitation singlet energy and excitation triplet energy of the light-emitting material, respectively.

[0067] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the hole injection or transport characteristics and the electron barrier characteristics. 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 (particularly thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as the hole transport material are given below.

[0068] [Chemical formula] JPEG0007899981000054.jpg41170

[0069] Electron transport layer: The electron transport layer contains an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to have the function of transporting electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole barrier material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole inducer 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.

[0070] [ka]

[0071] Furthermore, examples of preferred compounds that can be added to each organic layer are given. For example, they can be added as stabilizing materials.

[0072] [ka]

[0073] While specific examples of preferred materials that can be used in organic electroluminescent elements have been provided, the materials that can be used in the present invention are not limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials with specific functions can be repurposed as materials with other functions.

[0074] device: In some embodiments, the light-emitting layer is incorporated into the device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the components described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the components may be useful for facilitating charge transfer or energy transfer within the device and / or as hole transport materials. Examples of such devices include organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0075] Bulb or lamp: In some embodiments, the electronic device includes an OLED comprising an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising combinations of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, and blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device is A circuit board having a first surface with a mounting surface and a second surface opposite to it, defining at least one opening, The mounting surface comprises at least one OLED having a light-emitting configuration, wherein the at least one OLED includes an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, A housing for a circuit board, An OLED light comprising at least one connector located at the end of the housing, wherein the housing and the connector define a package suitable for mounting to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some of the light emitted in the 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.

[0076] Display or screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compound according to the present invention is deposited on a substrate using a process such as vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD), but is not limited. In some embodiments, the substrate is a photoplate structure useful in two-sided etching, providing pixels with a unique aspect ratio. The screen (also called a mask) is used in the manufacturing process of an OLED display. The design of the corresponding artwork pattern allows for the arrangement of very steep, narrow tie bars between pixels in the vertical direction, as well as large, wide oblique apertures in the horizontal direction. This enables the fine pattern configuration of pixels required for high-resolution displays, while optimizing chemical vapor deposition on a TFT backplane. Internal patterning of pixels allows for the creation of three-dimensional pixel apertures with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within a pixel area protects etching in specific areas until these particular patterns are undercut and removed from the substrate. At that time, all pixel areas are processed at a similar etching rate, but the depth varies depending on the halftone pattern. By changing the size and spacing of the halftone patterns, etching with varying degrees of protection within the pixel becomes possible, enabling localized deep etching necessary to form steep vertical bevels. A preferred material for deposition masks is Invar. Invar is a metal alloy that is cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming openings within a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0077] Device manufacturing method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin-film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, coating the TFT with a planarization film, sequentially forming pixel electrodes, an emissive layer, a counter electrode, and an encapsulation layer over time, and then cutting it from the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Usually, each cell panel on the mother panel forms a thin-film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applies a planarization film to the TFT, and sequentially forms a pixel electrode, a light-emitting layer, a counter electrode, and a encapsulation layer over time, and is formed by cutting from the mother panel.

[0078] In another aspect of the present invention, there is provided a method for manufacturing an organic light-emitting diode (OLED) display, the method comprising: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units in cell panel units on the barrier layer; forming an encapsulation layer on each of the display units of the cell panel; applying an organic film to an interface portion between the cell panels, and the method includes. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and an end portion of the barrier layer is covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel in cell panel units. In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may have a thin-film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface portion is formed of the same material as the material of the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer covering and protecting 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.

[0079] Each of the organic film and the planarization film may contain either polyimide or acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include the steps of attaching a carrier substrate made of glass material to another surface of the base substrate before forming a barrier layer on one surface of the polyimide base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film placed on the TFT layer for coating the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is made of polyimide or acrylic, as is the organic film formed at the edges of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed at the edges of the barrier layer, so that a portion of the organic film is in direct contact with the base substrate, and the remaining portion of the organic film is in contact with the barrier layer while surrounding the edges of the barrier layer.

[0080] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to the source / drain electrodes of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit will be referred to as a display unit. In some embodiments, the encapsulation layer covering the display unit and preventing the penetration of external moisture may be formed as a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film is in direct contact with the base substrate, while the remaining portion of the organic film surrounds the edges of the barrier layer while also being in contact with the barrier layer.

[0081] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of glass material, and then the carrier substrate is 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 interface between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0082] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, where a groove is formed in the barrier layer, and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, a TFT layer is formed for each cell panel, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on the TFT layer and cover the TFT layer. At the same time that a planarization film made of, for example, polyimide or acrylic is formed, the groove in the interface portion is covered with an organic film made of, for example, polyimide or acrylic. This prevents cracking by allowing the organic film to absorb the impact generated when each cell panel is cut along the groove at the interface portion. That is, if all barrier layers are completely exposed without an organic film, when each cell panel is cut along the groove at the interface portion, the impact generated is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the groove in the interface portion between barrier layers may be covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel is cut softly and cracking in the barrier layer is prevented. In one embodiment, the organic film and the planarizing film covering the grooves of the interface portion are arranged with a gap between them. For example, if the organic film and the planarizing film are connected to each other as a single layer, there is a risk that external moisture may penetrate the display unit through the remaining parts of the planarizing film and organic film. Therefore, the organic film and the planarizing film are arranged with a gap between them so that the organic film is spaced away from the display unit.

[0083] In some embodiments, the display unit is formed by the formation of a light-emitting unit, and an encapsulation layer is placed on the display unit to cover it. This separates the carrier substrate supporting the base substrate from the base substrate after the mother panel is completely manufactured. In some embodiments, when a laser beam is emitted onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficients between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into cell panel units. In some embodiments, the mother panel is cut along the interface between cell panels using a cutter. In some embodiments, the grooves of the interface along which the mother panel is cut are covered with an organic film so that the organic film absorbs the impact during cutting. In some embodiments, cracking can be prevented in the barrier layer during cutting. In some embodiments, the method reduces the defect rate of the product and stabilizes its 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 coated on the edges of the barrier layer. [Examples]

[0084] The features of the present invention will be further described in detail below with reference to synthesis examples and embodiments. The materials, processing content, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below. The luminescence characteristics were evaluated using a source meter (Keithley Corporation: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport Corporation: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon Corporation: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). In the following synthesis examples, compounds included in general formula (1) were synthesized.

[0085] (Synthesis Example 1) Synthesis of Compound 1204 [ka]

[0086] Under a nitrogen atmosphere, 3-bromodibenzo[a,c]phenazine (1.1 g, 3.06 mmol), 1-dibenzofuranylboronic acid (636 mg, 3.00 mmol), tetrakistriphenylphosphinepalladium (0) (346 mg, 0.299 mmol), and potassium carbonate (1.24 g, 8.97 mmol) were dissolved in a mixed solution of tetrahydrofuran and water (100 / 50 ml) and stirred at 75°C for 12 hours. The reaction solution was cooled to room temperature, the solid was filtered, and the obtained solid was washed twice with ethyl acetate. The obtained solid was purified by silica gel column chromatography (eluent: toluene), and then recrystallized in toluene to obtain compound 1204 as a pale yellow solid (1.08 g, 81%). 1 H NMR (400MHz, CDCl3, δ): 9.59 (d, J = 8 Hz, 1H), 9.48 (m, 1H), 8.87 (s, 1H), 8.58 (m, 1H), 8.39 (m, 2H), 8.05 (d, J= 8 Hz, 1H), 7.90 (m, 2H), 7.79 (m, 2H),7.68-7.59 (m, 4H), 7.50 (d, J = 8 Hz, 1H), 7.43 (t, J = 8 Hz, 1H), 7.09 (t, J = 8 Hz, 1H). MS (ASAP): 447.40 (M+H + Calcd for C 32 H 18 N2O: 446.14.

[0087] (Synthesis Example 2) Synthesis of Compound 30004 [ka]

[0088] 3,6-Dibromo-9,10-phenanceredione (3.66 g, 10 mmol), 1-dibenzofuranylboronic acid (2.12 g, 10 mmol), tetrakistriphenylphosphinepalladium (0) (1.16 g, 1 mmol), and potassium carbonate (5.52 g, 4 mmol) were dissolved in a mixed solution of tetrahydrofuran and water (200 / 100 ml) and stirred at 75°C for 12 hours. The reaction solution was cooled to room temperature, acetone was added, and the resulting solid was further washed with acetone. The resulting solid was purified by silica gel column chromatography (eluent: dichloromethane) and then recrystallized with toluene to obtain an orange solid intermediate a (2.12 g, 39%). MS (ASAP): 541.37 (M+H + Calcd for C 38 H 20 O4: 540.14.

[0089] Intermediate a (1.1 g, 2.03 mmol) and 9,10-diaminophenanthrene (500 mg, 2.4 mmol) were dissolved in 200 ml of acetic acid and stirred at room temperature for 12 hours. Methanol was added to the reaction solution, and the solid was filtered. The obtained solid was purified by short silica gel column chromatography (eluent: toluene). After removing the solvent, the obtained solid was washed with chloroform to obtain compound 30004 as a pale yellow solid (0.59 g, 41%). MS (ASAP): 713.64 (M+H + Calcd for C 52 H 28 N2O2: 712.22.

[0090] (Synthesis Example 3) Synthesis of Compound 30084 [ka]

[0091] Compound 30084 is synthesized according to the above reaction equation, using the same synthesis method as in Synthesis Example 2. This compound is useful as a hole barrier material.

[0092] (Example 1) Fabrication of an organic electroluminescent element Each thin film is deposited onto a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm using a vacuum deposition method at a vacuum of 5 × 10⁻¹⁰. -5 The layers were stacked using Pa. First, HATCN was formed to a thickness of 10 nm on ITO, and then NPD was formed on top of it to a thickness of 30 nm. Next, TrisPCz was formed to a thickness of 10 nm on top of that, and then H1 was formed to a thickness of 5 nm. Then, compound 1204 and TADF1 were co-deposited from different deposition sources to form a light-emitting layer with a thickness of 40 nm. The content of compound 1204 and TADF1 was 95 mass% and 5 mass%, respectively. On top of that, SF3TRZ was formed to a thickness of 10 nm, and then SF3TRZ and Liq were co-deposited from different deposition sources at 70 mass% and 30 mass%, respectively, to form a layer with a thickness of 30 nm. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form the cathode. Device 1 was fabricated by the above procedure. The only change made was the use of H1 instead of compound 1204; otherwise, the same procedure was followed to fabricate comparison element 1. When current was applied to the electrodes of each fabricated element, delayed fluorescence originating from TADF1 was observed. Furthermore, 15.4 mA / cm² was detected. 2 When the drive voltage was measured, the drive voltage of element 1 of the present invention was 24.61V lower than that of comparative element 1, confirming that the drive voltage is lowered when the compound of general formula (1) is used as a host material in combination with a delayed fluorescence material. Element 2 was fabricated following the same procedure, with the only change being the use of compound 30004 instead of compound 1204. When the drive voltage was measured in the same manner, it was found to be 23.78V lower than that of comparison element 1, confirming that using the compound of general formula (1) as a host material in combination with a delayed fluorescence material results in a lower drive voltage.

[0093] (Example 2) Fabrication of an organic electroluminescent device Element 3 was fabricated following the same procedure as in Example 1, except that the light-emitting layer of Example 1 was formed by co-depositing H1, compound 1204, and TADF1 from different deposition sources in amounts of 60% by mass, 20% by mass, and 20% by mass. Furthermore, the only modification to the light-emitting layer of Example 1 was that compound 1204 and TADF1 were co-deposited from different deposition sources in amounts of 80% by mass and 20% by mass, respectively, to create element 4, which was otherwise the same procedure as in Example 1. When current was applied to the electrodes of each fabricated element, delayed fluorescence originating from TADF1 was observed. Furthermore, 15.4 mA / cm² was detected. 2 When the driving voltage was measured, element 3 of the present invention had a driving voltage 0.36V lower than element 4. This confirmed that the driving voltage could be further reduced by using a total of two types of host materials in combination with the delayed fluorescence material in the light-emitting layer, by using a host material and a compound of general formula (1) in combination. Element 5 was fabricated following the same procedure, with the only change being the use of compound 30004 instead of compound 1204. When the drive voltage was measured similarly, it was 0.30V lower than that of element 4. This confirmed that the drive voltage could be further reduced by using a total of two types of host materials in combination with the delayed fluorescence material in the light-emitting layer, by using the host material and the compound of general formula (1) in combination.

[0094] [ka] [Industrial applicability]

[0095] Compounds represented by general formula (1) are useful as host materials, etc. Organic light-emitting devices using compounds represented by general formula (1) have excellent properties. For this reason, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1). 【Chemistry 1】 In general formula (1), Z １ represents N or C(R １１ ), and Z ２ represents N or C(R １２ ). R １ to R １２ each independently represents a hydrogen atom, a deuterium atom or a substituent. R １ and R ２ , R ２ and R ３ , R ３ and R １１ , R １２ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ may be bonded to each other to form a cyclic structure, but R １１ and R １２ do not bond to each other to form a cyclic structure. However, at least one of R １ to R １２ is a group represented by the following general formula (2). 【Chemistry 2】 [In general formula (2), R ２１ and R ２２ Each of the following independently represents a deuterium atom or substituent, and Ar represents a substituted or unsubstituted arylene group. n1 represents an integer from 0 to 4, n2 represents an integer from 0 to 3, and n3 represents 0 or 1. Adjacent R ２１ Allies, adjacent R ２２ They may be bonded to each other to form a ring structure. X is O, S, C(R ２３ ) (Caution ２４ ) or N(R ２５ ) represents R ２３ and R ２４ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ２５ represents a substituent. * represents a bond position. However, at least one of the following conditions (1) to (3) must be met. (1) The compound represented by the general formula (1) has a structure represented by the following general formula (1a). 【Transformation 3】 In general formula (1a), Z1 represents N or C (R11), Z2 represents N or C (R12), Z3 represents N or C (R19), and Z4 represents N or C (R20). R1 ​​to R6 and R11 to R20 each independently represent a hydrogen atom, a deuterium atom, or a substituent. R1 and R2, R2 and R3, R3 and R11, R12 and R4, R4 and R5, R5 and R6, R13 and R14, R14 and R15, R15 and R19, R20 and R16, R16 and R17, and R17 and R18 may combine to form a ring structure, but R11 and R12 will not combine to form a ring structure, nor will R19 and R20 combine to form a ring structure. However, at least one of R1 to R6, R11, and R12 is a group represented by the general formula (2) above. (2) The group represented by the general formula (2) has the structure represented by the general formula (2a) below. 【Chemistry 4】 (3) The compound represented by the general formula (1) is a symmetric compound.

2. The compound according to claim 1, wherein n3 is 0.

3. The compound according to claim 1, wherein n3 is 1.

4. The compound according to claim 3, wherein Ar is an m-phenylene group or a p-phenylene group.

5. Z １ is C(R １１ ) and Z ２ is C(R １２ The compound according to claim 1, which is the compound described in claim 1.

6. Z １ and Z ２ The compound according to claim 1, wherein is N.

7. R １ and R ２ , R ２ and R ３ , R ３ and R １１ , R １２ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ The compound according to claim 1, wherein none of them are bonded to each other to form a cyclic structure.

8. The compound according to claim 1, which satisfies the conditions of (1) above.

9. Z １ is C(R １１ ) and Z ２ is C(R １２ ) and Z ３ is C(R １９ ) and Z ４ is C(R ２０ The compound according to claim 8, which is the compound described in claim 8.

10. Z １ is C(R １１ ) and Z ２ is C(R １２ ) and Z ３ and Z ４ The compound according to claim 8, wherein is N.

11. The compound according to claim 1, wherein the molecule contains only one group represented by the general formula (2).

12. The compound according to claim 1, wherein the molecule contains only two groups represented by the general formula (2).

13. R １ ~R ６ , R １１ , R １２ The compound according to claim 1, wherein at least one of the groups is a group represented by the general formula (2).

14. R ７ ~R １０ The compound according to claim 1, wherein at least one of the groups is a group represented by the general formula (2).

15. The compound according to claim 1, which satisfies the conditions of (2) above.

16. The compound according to claim 1, wherein X is O.

17. R １ ~R １２ The compound according to claim 1, wherein each of them is independently a hydrogen atom, a deuterium atom, or a group represented by the general formula (2).

18. The compound according to claim 1, which satisfies the conditions of (3) above.

19. A host material comprising the compound described in any one of claims 1 to 18.

20. A host material for use with a delayed fluorescence material, comprising a compound represented by the following general formula (1). 【Transformation 5】 In general formula (1), Z1 represents N or C (R11), and Z2 represents N or C (R12). R1 ​​to R12 each independently represent a hydrogen atom, a deuterium atom, or a substituent. R1 and R2, R2 and R3, R3 and R11, R12 and R4, R4 and R5, R5 and R6, R7 and R8, R8 and R9, and R9 and R10 may bond to each other to form a cyclic structure, but R11 and R12 will not bond to each other to form a cyclic structure. However, at least one of R1 to R12 is a group represented by the following general formula (2). 【Transformation 6】 [In general formula (2), R 21 and R 22 each independently represent a deuterium atom or a substituent, and Ar represents a substituted or unsubstituted arylene group. n1 represents an integer from 0 to 4, n2 represents an integer from 0 to 3, and n3 represents 0 or 1. Adjacent R 21s and adjacent R 22s may bond to each other to form a cyclic structure. X represents O, S, C (R 23) (R 24) or N (R 25). R 23 and R 24 each independently represent a hydrogen atom, a deuterium atom, or a substituent, and R 25 represents a substituent. * indicates a bond position.]

21. A hole barrier material comprising a compound represented by the following general formula (1). 【Transformation 7】 In general formula (1), Z1 represents N or C (R11), and Z2 represents N or C (R12). R1 ​​to R12 each independently represent a hydrogen atom, a deuterium atom, or a substituent. R1 and R2, R2 and R3, R3 and R11, R12 and R4, R4 and R5, R5 and R6, R7 and R8, R8 and R9, and R9 and R10 may bond to each other to form a cyclic structure, but R11 and R12 will not bond to each other to form a cyclic structure. However, at least one of R1 to R12 is a group represented by the following general formula (2). 【Transformation 8】 [In general formula (2), R 21 and R 22 each independently represent a deuterium atom or a substituent, and Ar represents a substituted or unsubstituted arylene group. n1 represents an integer from 0 to 4, n2 represents an integer from 0 to 3, and n3 represents 0 or 1. Adjacent R 21s and adjacent R 22s may bond to each other to form a cyclic structure. X represents O, S, C (R 23) (R 24) or N (R 25). R 23 and R 24 each independently represent a hydrogen atom, a deuterium atom, or a substituent, and R 25 represents a substituent. * indicates a bond position.]

22. An organic light-emitting element comprising the compound according to any one of claims 1 to 18.

23. An organic light-emitting element having a light-emitting layer containing a compound represented by the following general formula (1) and a delayed fluorescence material. 【Chemistry 9】 In general formula (1), Z1 represents N or C (R11), and Z2 represents N or C (R12). R1 ​​to R12 each independently represent a hydrogen atom, a deuterium atom, or a substituent. R1 and R2, R2 and R3, R3 and R11, R12 and R4, R4 and R5, R5 and R6, R7 and R8, R8 and R9, and R9 and R10 may bond to each other to form a cyclic structure, but R11 and R12 will not bond to each other to form a cyclic structure. However, at least one of R1 to R12 is a group represented by the following general formula (2). 【Chemistry 10】 [In general formula (2), R 21 and R 22 each independently represent a deuterium atom or a substituent, and Ar represents a substituted or unsubstituted arylene group. n1 represents an integer from 0 to 4, n2 represents an integer from 0 to 3, and n3 represents 0 or 1. Adjacent R 21s and adjacent R 22s may bond to each other to form a cyclic structure. X represents O, S, C (R 23) (R 24) or N (R 25). R 23 and R 24 each independently represent a hydrogen atom, a deuterium atom, or a substituent, and R 25 represents a substituent. * indicates a bond position.]

24. The organic light-emitting element according to claim 23, wherein the light-emitting layer further comprises a host material not represented by the general formula (1).

25. The organic light-emitting element according to claim 24, wherein the host material not represented by the general formula (1) has a structure represented by the following general formula (3). 【Chemistry 11】 [In general formula (3), R ３１ to R ３５ are each independently selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a group combining these. R ３１ to R ３４ do not combine with other R ３１ to R ３４ to form a cyclic structure, but adjacent R ３５ may combine with each other to form a benzofuro skeleton or a benzothieno skeleton. n31, n33, n34, and n35 each independently represent an integer of 0 to 4, and n32 represents an integer of 0 to 3. ]

26. The organic light-emitting element according to claim 22, further comprising a layer containing the compound as a layer adjacent to the light-emitting layer.

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