Compound, light-emitting material, and light-emitting element

Abstract

The compound represented by the following general formula has excellent luminescence characteristics. R1, R2, R3 and Z are D or substituent groups; r < 4 > to R < 8 > are H, D or substituent groups; at least one of R1-R8 represents an aryl group or an acceptor group; p is 0-3: q is 1-4. # imgabs0 #

Description

Technical Field

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

[0002] Research is actively being conducted to improve the luminous efficiency of light-emitting elements such as organic electroluminescent elements (organic EL elements). In particular, much effort has been made to improve the luminous efficiency by newly developing and combining an electron transport material, a hole transport material, a luminescent material, etc. constituting an organic electroluminescent element. Among them, research related to an organic electroluminescent element using a delayed fluorescence material has also been seen.

[0003] A delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after undergoing reverse intersystem crossing from the excited triplet state in the excited state. Fluorescence generated by this pathway is observed later than fluorescence from the excited singlet state directly generated from the ground state (ordinary fluorescence), and thus is called delayed fluorescence. Here, for example, in the case of exciting a luminescent compound by injection of carriers, the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%. Therefore, if only fluorescence from the directly generated excited singlet state is used, there is a limit to the improvement of luminous efficiency. On the other hand, in a delayed fluorescence material, in addition to the excited singlet state, the excited triplet state can also be used for fluorescence emission through the above-mentioned reverse intersystem crossing pathway, and thus higher luminous efficiency can be obtained compared with ordinary fluorescence materials.

[0004] After this principle was clarified, various delayed fluorescence materials were discovered through various studies. Among them, several compounds in which terephthalonitrile is substituted in a donor group are included. For example, a compound in which 9-carbazolyl as a donor group is substituted in terephthalonitrile has been proposed, and as an example, a compound (4CzTPN) having the following structure is actually used (refer to Non-Patent Document 1).

[0005] [Chemical formula 1]

[0006]

[0007] Prior Art Documents

[0008] Non-Patent Documents

[0009] Non-Patent Document 1: H.Uoyama et al., Nature 492, 234-238 (2012) Summary of the Invention

[0010] Technical Problem to be Solved by the Invention

[0011] So far, there has been no material that provides the following: even for a material that emits delayed fluorescence, its properties are extremely good and there are no practical problems. Therefore, if a delayed fluorescence material with good luminescence properties can be provided, it would be extremely useful. However, the improvement of delayed fluorescence materials is still in the experimental stage, and it is not easy to generalize the chemical structures of useful luminescent materials.

[0012] Under such circumstances, the present inventors repeatedly conducted research in order to provide a compound that is more useful as a luminescent material for a light-emitting element. Moreover, they painstakingly explored to derive and generalize the general formula of a compound that is more useful as a luminescent material.

[0013] Means for Solving the Technical Problem

[0014] As a result of painstaking exploration to achieve the above object, the present inventors found that terephthalonitrile having a structure that satisfies specific conditions can be used as a luminescent material. The present invention is proposed based on this insight, and specifically, it has the following structure.

[0015] [1] A compound represented by the following general formula (1),

[0016] [Chemical formula 2]

[0017]

[0018] In general formula (1), X represents an oxygen atom, a sulfur atom or

[0019] [Chemical formula 3]

[0020]

[0021] , * represents the bonding position, R 1 ~R 3 and Z each independently represent a deuterium atom or a substituent, R 4 ~R 8 each independently represent a hydrogen atom, a deuterium atom or a substituent, and at least one of R 1 ~R 8 is a substituted or unsubstituted aryl group or acceptor group. Among them, when R 2 is not an acceptor group, at least one of R 1 and R 3 ~R 8 is a substituted or unsubstituted 2,4,6-triazinyl group, n1 and n3 each independently represent any integer from 0 to 4, n2 represents any integer from 0 to 2, p represents any integer from 0 to 3, q represents any integer from 1 to 4. When n1 is an integer of 2 or more, two or more R 1 may be the same or different. When n2 is 2, two R 2may be the same or different. When n3 is an integer of 2 or more, two or more Rs 3 may be the same or different. When p is an integer of 2 or more, two or more Zs may be the same or different. When q is an integer of 2 or more, two or more structures within the parentheses may be the same or different.

[0022] [2] The compound according to [1], wherein at least one of R 1 ~R 3 is a receptor group.

[0023] [3] The compound according to [2], wherein R 2 is a receptor group.

[0024] [4] The compound according to any one of [1] to [3], wherein the receptor group is represented by the following general formula (b),

[0025] [Chemical formula 4]

[0026] General formula (b)

[0027]

[0028] [In the general formula (b), X 1 ~X 3 each independently represents N or C(R), wherein at least one of X 1 ~X 3 is N, R represents a hydrogen atom, a deuterium atom or a substituent, and Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.]

[0029] [5] The compound according to [4], wherein X 1 ~X 3 is N.

[0030] [6] The compound according to any one of [1] to [5], wherein Z is a substituted or unsubstituted diarylamino group (wherein the two aryl groups may be bonded to each other), or Z is a substituted or unsubstituted aryl group.

[0031] [7] The compound according to [6], wherein Z is a substituted or unsubstituted carbazol-9-yl group.

[0032] [8] The compound according to any one of [1] to [7], wherein X is an oxygen atom or a sulfur atom.

[0033] [9] The compound according to any one of [1] to [8], wherein q is 1.

[0034]

[10] The compound according to any one of [1] to [9], wherein n1 + n2 + n3 is 1 or more.

[0035]

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

[10] , which has at least one deuterium atom.

[0036]

[12] A luminescent material comprising the compound according to any one of [1] to

[11] .

[0037]

[13] A delayed phosphor comprising the compound according to any one of [1] to

[11] .

[0038]

[14] A film comprising the compound according to any one of [1] to

[11] .

[0039]

[15] An organic semiconductor element comprising the compound according to any one of [1] to

[11] .

[0040]

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

[11] .

[0041]

[17] The organic light-emitting element according to

[16] , wherein the element has a layer containing the compound, and the layer further contains a host material.

[0042]

[18] The organic light-emitting element according to

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

[0043]

[19] The organic light-emitting element according to

[17] , wherein

[0044] the element has a layer containing the compound, and the layer further contains a luminescent material having a structure different from that of the compound.

[0045]

[20] The organic light-emitting element according to

[17] , wherein

[0046] the amount of light emission from the compound in the materials contained in the element is the largest.

[0047]

[21] The organic light-emitting element according to

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

[0048]

[22] The organic light-emitting element according to any one of

[16] to

[21] , which is an organic electroluminescent element.

[0049]

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

[16] to

[22] emits delayed fluorescence.

[0050] Advantages of the Invention

[0051] The compound of the present invention exhibits excellent light-emitting properties. The compound of the present invention can be used as a material for an organic light-emitting element. Detailed Description of the Invention

[0052] The content of the present invention will be described in detail below. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, in this specification, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. And, a part or all of the hydrogen atoms in the molecule of the compound used in the present invention can be substituted with deuterium atoms ( 2 H, deuterium D). In the chemical structural formula of this specification, a hydrogen atom is represented as H or its representation is omitted. For example, when an atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom constituting the ring skeleton at the omitted position. In this specification, the term "substituent" means an atom or atomic group other than a hydrogen atom and a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom can be substituted with a deuterium atom or a substituent.

[0053] [Compound represented by General Formula (1)]

[0054] The compound represented by the following General Formula (1) will be described.

[0055] [Chemical Formula 5]

[0056] General Formula (1)

[0057]

[0058] In general formula (1), Z represents a deuterium atom or a substituent. Among them, Z is not a cyano group, and Z is also not the polycyclic carbazole-9-yl described in the parentheses of q. p represents any integer from 0 to 3. When p is 2 or 3, the two or three Zs can be the same or different. The substituents that Z can adopt can be selected, for example, from the following substituent group A, or from substituent group B, or from substituent group C, or from substituent group D, or from substituent group E. In a preferred embodiment of the present invention, the substituents that Z can adopt are a substituted or unsubstituted aryl group, or a substituted or unsubstituted diarylamino group. The diarylamino group mentioned herein also includes a group in which the two aryl groups bonded to the nitrogen atom are bonded to each other via a single bond or a linking group, for example, it also includes carbazole-9-yl. Except for the polycyclic carbazole-9-yl described in the parentheses of q.

[0059] In one embodiment of the present invention, at least one Z is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one Z is a substituted or unsubstituted diarylamino group, for example, at least one Z is a substituted or unsubstituted carbazole-9-yl. In one embodiment of the present invention, at least one Z is a deuterium atom. In one embodiment of the present invention, all Zs are substituted or unsubstituted aryl groups. In one embodiment of the present invention, all Zs are substituted or unsubstituted diarylamino groups, for example, all Zs are substituted or unsubstituted carbazole-9-yl. In one embodiment of the present invention, all Zs are deuterium atoms. In one embodiment of the present invention, p is 2 or 3, at least one Z is a substituted or unsubstituted aryl group, and at least one Z is a substituted or unsubstituted diarylamino group. In one embodiment of the present invention, p is 1. In one embodiment of the present invention, p is 2. In one embodiment of the present invention, p is 3.

[0060] bonded to (Z) p Two cyano groups are bonded to the benzene ring. In one embodiment of the present invention, the two cyano groups are in a para relationship. In one embodiment of the present invention, the two cyano groups are in a meta relationship. In one embodiment of the present invention, the two cyano groups are in an ortho relationship.

[0061] q in general formula (1) represents any integer from 1 to 4. In one embodiment of the present invention, p + q is 4. In one embodiment of the present invention, p + q is 3. In one embodiment of the present invention, p + q is 2. In one embodiment of the present invention, p + q is 1. Preferably, p + q is 2 to 4, more preferably 3 or 4. In one embodiment of the present invention, p is 2 or 3 and q is 1, for example, p is 3 and q is 1, for example, p is 2 and q is 1. In one embodiment of the present invention, p is 1 or 2 and q is 2, for example, p is 2 and q is 2, for example, p is 1 and q is 2.

[0062] Hereinafter, specific examples of the bonding positions of the fused-ring carbazol-9-yl group described in parentheses of cyano, Z, and q are given, but the bonding positions that can be used in the present invention are not restrictively interpreted by the following specific examples. In the following specific examples, the fused-ring carbazol-9-yl group described in parentheses of q in the general formula (1) is denoted as Cz. When there are multiple Zs, these Zs may be the same or different, for example, the same. When there are multiple Czs, these Czs may be the same or different, for example, the same. I7 to I11, P5, P6, T7 to T10 are specific examples when Z is a deuterium atom (D).

[0063] [Chemical formula 6]

[0064]

[0065] In one embodiment of the present invention, it has any one of the structures of T1 to T10. In one embodiment of the present invention, it has any one of the structures of T1 to T6. For example, it has the structure of T1, T3, T4, or T5. For example, it has the structure of T3, T4, T5, or T6. For example, it has the structure of T5 or T6. In one embodiment of the present invention, it has any one of the structures of T7 to T10. For example, it has the structure of T7, T8, or T9. In one embodiment of the present invention, it has any one of the structures of P1 to P6. In one embodiment of the present invention, it has any one of the structures of P1 to P4. For example, it has the structure of P3 or P4. For example, it has the structure of P1 or P2. In one embodiment of the present invention, it has the structure of P5 or P6. In one embodiment of the present invention, it has any one of the structures of I1 to I11. In one embodiment of the present invention, it has any one of the structures of I1 to I6. For example, it has the structure of I1 or I3. For example, it has the structure of I2 or I4. In one embodiment of the present invention, it has any one of the structures of I7 to I11. For example, it has the structure of I7, I9, or I11. For example, it has the structure of I8 or I10.

[0066] In one embodiment of the present invention, it has any one of the structures of I1 to I6, P1 to P4, and T1 to T6. In one embodiment of the present invention, it has any one of the structures of I7 to I11, P5, P6, and T7 to T10. In one embodiment of the present invention, it has any one of the structures of I1, I3, I5, I7, I9, I11, P3 to P6, T1, T3 to T5, and T7 to T9. In one embodiment of the present invention, it has any one of the structures of I7 to I11, P5, P6, and T7 to T10. In one embodiment of the present invention, it has any one of the structures of I7, I9, I11, P5, P6, and T7 to T9.

[0067] Hereinafter, specific examples of the substituents that Z can adopt are given. However, the substituents that can be adopted as Z are not restrictively interpreted by these specific examples. In the following specific examples, * represents the bonding position, and "D" represents a deuterium atom.

[0068] [Chemical formula 7-1]

[0069]

[0070] [Chemical formula 7-2]

[0071]

[0072] In one embodiment of the present invention, Z is selected from Z1 to Z35. In one embodiment of the present invention, Z is selected from Z27 to Z35. In one embodiment of the present invention, Z is selected from Z5 to Z26, Z31 to Z35. In one embodiment of the present invention, Z is selected from Z7 to Z26, Z33 to Z35.

[0073] In the general formula (1), X represents an oxygen atom, a sulfur atom, or a group represented by the following general formula (a).

[0074] [Chemical formula 8]

[0075] General formula (a)

[0076]

[0077] In the general formula (a), * represents the bonding position, and R 4 ~R 8 each independently represents a hydrogen atom, a deuterium atom, or a substituent. R 4 ~R 8 The substituents that can be adopted can be selected from the substituent group A described later, can be selected from the substituent group B, can be selected from the substituent group C, can be selected from the substituent group D, and can be selected from the substituent group E. R 4 ~R 8 can be the same, and for example, cases where all are hydrogen atoms or all are deuterium atoms can be exemplified. In one embodiment of the present invention, R 4 ~R 8 is selected from a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, and a group formed by combining them. In one embodiment of the present invention, R 4 ~R 8 is selected from a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, a diarylamino group (the two aryl groups can be bonded to each other), and a group formed by combining them. In one embodiment of the present invention, R 4 ~R 8Select from hydrogen atoms, deuterium atoms, alkyl groups, and groups formed by combining them.

[0078] In one embodiment of the present invention, X is an oxygen atom or a sulfur atom, and the oxygen atom can be selected, or the sulfur atom can be selected. In one embodiment of the present invention, X is a group represented by the general formula (a). In the general formula (1), it also includes the case where the positional relationship between the benzene ring bonded to (R 3 ) n3 and the benzene ring bonded to (R 2 ) n2 through X and a single bond is opposite. That is, in the above general formula (1), X is described on the upper side and the single bond is described on the lower side, but the case where X is on the lower side and the single bond is on the upper side is also included in the general formula (1).

[0079] The benzene ring bonded to (R 3 ) n3 and X are fused to the carbazole ring through a single bond, thereby forming a ring-fused carbazol-9-yl. As such a ring-fused carbazol-9-yl, benzofuro[2,3-a]carbazol-9-yl, benzofuro[3,2-a]carbazol-9-yl, benzofuro[2,3-b]carbazol-9-yl, benzofuro[3,2-b]carbazol-9-yl, benzofuro[2,3-c]carbazol-9-yl, benzofuro[3,2-c]carbazol-9-yl can be used. And, as the ring-fused carbazol-9-yl, benzothieno[2,3-a]carbazol-9-yl, benzothieno[3,2-a]carbazol-9-yl, benzothieno[2,3-b]carbazol-9-yl, benzothieno[3,2-b]carbazol-9-yl, benzothieno[2,3-c]carbazol-9-yl, benzothieno[3,2-c]carbazol-9-yl can also be used. And, as the ring-fused carbazol-9-yl, indolo[2,3-a]carbazol-9-yl, indolo[3,2-a]carbazol-9-yl, indolo[2,3-b]carbazol-9-yl, indolo[3,2-b]carbazol-9-yl, indolo[2,3-c]carbazol-9-yl, indolo[3,2-c]carbazol-9-yl can also be used. The benzene rings constituting these groups are each substituted on (R 1 ) n1 , (R 2 ) n2 and (R 3 ) n3 as shown in the general formula (1).

[0080] R 1 to R 3 each independently represent a deuterium atom or a substituent. R 1 to R 3The substituents that can be used can be selected, for example, from the following substituent group A, or can be selected from substituent group B, or can be selected from substituent group C, or can be selected from substituent group D, or can be selected from substituent group E.

[0081] In general formula (1), R 1 ~R 8 At least one of them is a substituted or unsubstituted aryl group or acceptor group. In a preferred embodiment of the present invention, R 1 ~R 3 At least one of them is a substituted or unsubstituted aryl group or acceptor group. In a more preferred embodiment of the present invention, R 2 At least one of them is a substituted or unsubstituted aryl group or acceptor group, and more preferably an acceptor group.

[0082] Regarding the "acceptor group", it can be selected from groups having a positive Hammett σp value. The Hammett σp value was proposed by L.P. Hammett to quantify the influence of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, it is the following formula established between the substituent in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant:

[0083] log(k / k0) = ρσp

[0084] Or

[0085] log(K / K0) = ρσp

[0086] The substituent-specific constant (σp) in the above formula. In the above formula, k0 represents the rate constant of the benzene derivative without a substituent, k represents the rate constant of the benzene derivative substituted with a substituent, K0 represents the equilibrium constant of the benzene derivative without a substituent, K represents the equilibrium constant of the benzene derivative substituted with a substituent, and ρ represents the reaction constant determined by the type and conditions of the reaction. Regarding the description related to the "Hammett σp value" in the present invention and the numerical values of each substituent, reference can be made to the description related to the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991).

[0087] R 1 ~R 8 The σp of the acceptor group that can be used is preferably 0.3 or more, more preferably 0.5 or more, and further preferably 0.7 or more. For example, it can be selected from the range of 0.9 or more or from the range of 1.1 or more.

[0088] In a preferred embodiment of the present invention, R 1 ~R 8The receptor group that can be used is a heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom. More preferably, it is a group represented by the following general formula (b).

[0089] [Chemical Formula 9]

[0090] General formula (b)

[0091]

[0092] In general formula (b), X 1 ~X 3 each independently represents N or C(R). Among them, at least one of X 1 ~X 3 is N. R represents a hydrogen atom, a deuterium atom or a substituent. Regarding the substituents described herein, they can be selected from substituent group A, or from substituent group B, or from substituent group C, or from substituent group D, or from substituent group E. In a preferred embodiment of the present invention, X 1 ~X 3 are N. In one embodiment of the present invention, X 1 and X 3 are N, and X 2 is C(R). In one embodiment of the present invention, X 1 and X 2 are N, and X 3 is C(R). In one embodiment of the present invention, X 1 is N, and X 2 and X 3 are C(R). In one embodiment of the present invention, X 2 is N, and X 1 and X 3 are C(R). In one embodiment of the present invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R is an alkyl group that can be substituted with a deuterium atom. In one embodiment of the present invention, R is an aryl group that can be substituted with a deuterium atom, an alkyl group or an aryl group.

[0093] In general formula (b), Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0094] Ar 1 and Ar 2The aryl groups that can be used and the aryl groups in the present invention can be monocyclic or polycyclic fused by two or more rings. In the case of polycyclic fused rings, the number of fused rings is preferably 2 to 6, and can be selected from 2 to 4, for example. Specific examples of the ring include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, and triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, preferably a substituted or unsubstituted phenyl group. Regarding the substituents of the aryl group, they can be selected from substituent group A, or from substituent group B, or from substituent group C, or from substituent group D, or from substituent group E, for example. In one embodiment of the present invention, the substituents of the aryl group are one or more selected from the group consisting of alkyl groups, aryl groups, and deuterium atoms. In a preferred embodiment of the present invention, the aryl group is substituted with at least one deuterium atom. In one embodiment of the present invention, the aryl group is unsubstituted.

[0095] Ar 1 and Ar 2 The heteroaryl groups that can be used and the heteroaryl groups in the present invention can be monocyclic or polycyclic fused by two or more rings. In the case of polycyclic fused rings, the number of fused rings is preferably 2 to 6, and can be selected from 2 to 4, for example. Specific examples of the ring include pyridine ring, pyrimidine ring, and pyrrole ring, and these rings can be further fused with other rings. Specific examples of the heteroaryl group include 2-pyridyl, 3-pyridyl, 4-pyridyl, carbazol-9-yl, carbazol-1-yl, carbazol-2-yl, carbazol-3-yl, and carbazol-4-yl. These groups can be substituted with substituents, for example, they can be substituted with deuterium atoms, alkyl groups, aryl groups, carbazolyl groups, and groups formed by combining them.

[0096] Hereinafter, specific examples of the acceptor groups that can be used in the present invention are shown. However, the acceptor groups that can be used in the present invention should not be construed as being limited by these specific examples. In the following specific examples, * represents the bonding position, and "D" represents a deuterium atom.

[0097] [Chemical formula 10-1]

[0098]

[0099] [Chemical formula 10-2]

[0100]

[0101] [Chemical formula 10-3]

[0102]

[0103] In one embodiment of the present invention, the acceptor group is selected from A1 to A32. In one embodiment of the present invention, the acceptor group is selected from A16 to A32. In one embodiment of the present invention, the acceptor group is selected from A4 to A15, A19 to 32. In one embodiment of the present invention, the acceptor group is selected from A4 to A10, A19 to 28. In one embodiment of the present invention, the acceptor group is selected from A11 to A14, A29 to 31.

[0104] In a preferred embodiment of the present invention, R 1 ~R 3 is selected from a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted triazinyl group. In a preferred embodiment of the present invention, R 1 ~R 3 is selected from a deuterium atom, a substituted or unsubstituted aryl group, and a substituted or unsubstituted 2,4,6-triazinyl group. In a preferred embodiment of the present invention, R 1 ~R 3 is selected from a deuterium atom, an aryl group that may be substituted with a deuterium atom, and A1 to A32.

[0105] n1 and n3 each independently represent any integer from 0 to 4, n2 represents any integer from 0 to 2, and p represents any integer from 0 to 3. Among them, n1 + n2 + n3 is preferably an integer of 1 or more, more preferably 1 to 3, for example 1, for example 2. When n1 is an integer of 2 or more, two or more R 1 may be the same or different. When n2 is 2, the two R 2 may be the same or different. When n3 is an integer of 2 or more, two or more R 3 may be the same or different. When p is an integer of 2 or more, two or more Zs may be the same or different.

[0106] In the general formula (1), at least one of R 1 ~R 8 is a substituted or unsubstituted aryl group or an acceptor group. In a preferred embodiment of the present invention, at least one of R 1 ~R 8 is an acceptor group, for example, a group represented by the general formula (b), preferably a substituted or unsubstituted 2,4,6-triazinyl group. In a preferred embodiment of the present invention, at least one of R 1 ~R 3 is an acceptor group, for example, a group represented by the general formula (b), preferably a substituted or unsubstituted 2,4,6-triazinyl group. In one embodiment of the present invention, R 3At least one of them is a receptor group, for example, a group represented by the general formula (b), preferably a substituted or unsubstituted 2,4,6-triazinyl group. In a preferred embodiment of the present invention, R 1 At least one of them is a receptor group, for example, a group represented by the general formula (b), preferably a substituted or unsubstituted 2,4,6-triazinyl group. In another preferred embodiment of the present invention, R 2 At least one of them is a receptor group, for example, a group represented by the general formula (b), preferably a substituted or unsubstituted 2,4,6-triazinyl group. Additionally, when none of R 2 is a receptor group, at least one of R 1 and R 3 ~R 8 is a substituted or unsubstituted 2,4,6-triazinyl group.

[0107] In one embodiment of the present invention, n1 + n2 + n3 is 1 to 3, and at least one (for example, one) of R 1 ~R 3 is a receptor group, for example, a group represented by the general formula (b), preferably a substituted or unsubstituted 2,4,6-triazinyl group, and 0 to 2 (for example, 0, for example, 1) of R 1 ~R 3 are substituted or unsubstituted aryl groups, for example, aryl groups that can be substituted by deuterium atoms, alkyl groups, or aryl groups.

[0108] Hereinafter, specific examples of the fused-ring carbazol-9-yl group described in the parentheses of q are given. However, the structure of the fused-ring carbazol-9-yl group that can be used in the present invention is not restrictively interpreted by these specific examples. In the following specific examples, * represents the bonding position, A represents the receptor group, and D represents the deuterium atom.

[0109] [Chemical formula 11-1]

[0110]

[0111] [Chemical formula 11-2]

[0112]

[0113] [Chemical formula 11-3]

[0114]

[0115] [Chemical formula 11-4]

[0116]

[0117] [Chemical formula 11-5]

[0118]

[0119] [Chemical Formula 11-6]

[0120]

[0121] [Chemical Formula 11-7]

[0122]

[0123] [Chemical Formula 11-8]

[0124]

[0125] [Chemical Formula 11-9]

[0126]

[0127] [Chemical Formula 11-10]

[0128]

[0129] [Chemical Formula 11-11]

[0130]

[0131] [Chemical Formula 11-12]

[0132]

[0133] [Chemical Formula 11-13]

[0134]

[0135] [Chemical Formula 11-14]

[0136]

[0137] [Chemical Formula 11-15]

[0138]

[0139] [Chemical Formula 11-16]

[0140]

[0141] [Chemical Formula 11-17]

[0142]

[0143] [Chemical Formula 11-18]

[0144]

[0145] [Chemical Formula 11-19]

[0146]

[0147] In one embodiment of the present invention, the fused-ring carbazol-9-yl is selected from Cz1 to Cz279. In one embodiment of the present invention, the fused-ring carbazol-9-yl is selected from Cz163 to Cz279. In one embodiment of the present invention, the fused-ring carbazol-9-yl is selected from Cz1 to Cz48, Cz67 to Cz90, Cz103 to Cz126, Cz139 to Cz146, Cz151 to Cz158, Cz163 to Cz198, Cz216 to Cz233, Cz243 to Cz260, Cz270 to Cz279. In one embodiment of the present invention, the fused-ring carbazol-9-yl is selected from Cz49 to Cz66, Cz91 to Cz102, Cz127 to Cz138, Cz147 to Cz150, Cz159 to Cz162, Cz199 to 215, Cz234 to Cz242, Cz261 to Cz269.

[0148] The compound represented by the general formula (1) is preferably a compound that does not contain a metal atom and may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. In a preferred embodiment of the present invention, the compound represented by the general formula (1) is composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and an oxygen atom. Further, the compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and a sulfur atom. The compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, and a nitrogen atom. The compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, and a nitrogen atom. In addition, the compound represented by the general formula (1) may be a compound that contains a deuterium atom and does not contain a hydrogen atom.

[0149] In this specification, "substituent group A" means an atom or group selected from the group consisting of a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton-constituting atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton-constituting atoms), a heteroarylthio group (e.g., having 5 to 30 ring skeleton-constituting atoms), an acyl group (e.g., having 1 to 40 carbon atoms), an alkenyl group (e.g., having 1 to 40 carbon atoms), an alkynyl group (e.g., having 1 to 40 carbon atoms), an alkoxycarbonyl group (e.g., having 1 to 40 carbon atoms), an aryloxycarbonyl group (e.g., having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (e.g., having 1 to 40 carbon atoms), a silyl group (e.g., a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group, or a group obtained by combining two or more thereof.

[0150] In this specification, "substituent group B" means an atom or group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton-constituting atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton-constituting atoms), and a diarylamino group (e.g., having 0 to 20 carbon atoms), or a group obtained by combining two or more thereof.

[0151] In this specification, "substituent group C" means an atom or group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton-constituting atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms), or a group obtained by combining two or more thereof.

[0152] In this specification, "substituent group D" means an atom or group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton-constituting atoms), or a group obtained by combining two or more thereof.

[0153] In this specification, "substituent group E" means an atom or group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), and an aryl group (e.g., having 6 to 22 carbon atoms), or a group obtained by combining two or more thereof.

[0154] In this specification, when a substituent is described as "substituted or unsubstituted" or "may be substituted", it can be selected from substituent group A, or from substituent group B, or from substituent group C, or from substituent group D, or from substituent group E, for example.

[0155] In the following table, specific examples of the compound represented by the general formula (1) are illustrated. However, the compound represented by the general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples.

[0156] In Table 1, after determining the basic skeleton (designated as PN) of the structure represented by the following general formula (1) from I1 to I11, P1 to P6, and T1 to T10, Z, Cz, and A are specified, thereby determining the structure of each compound. For example, for Compound 1, it has the basic skeleton of T5, and has the structure where Z in T5 is Z33, Cz in T5 is Cz13, and A in T5 is A1. For Compounds 2 to 64, the structures are determined in the same manner.

[0157] In Table 2, the structures of multiple compounds are determined and summarized in each section. For example, in the section of Compounds 1 to 32, when the basic skeleton is T5, Z is fixed as 33, and Cz is fixed as 13, the structures where A is A1 to A32 are sequentially determined as the structures of Compounds 1 to 32. That is, in the section of Compounds 1 to 32 in Table 2, the structures of Compounds 1 to 32 in Table 1 are summarized and described. The sections of Compounds 33 to 64 and subsequent sections are determined in the same manner.

[0158] [Table 1]

[0159]

[0160] [Table 2-1]

[0161]

[0162] [Table 2-2]

[0163]

[0164] [Table 2-3]

[0165]

[0166] [Table 2-4]

[0167]

[0168] [Table 2-5]

[0169]

[0170] [Table 2-6]

[0171]

[0172] [Table 2-7]

[0173]

[0174] [Table 2-8]

[0175]

[0176] In a preferred embodiment of the present invention, the compound represented by the general formula (1) is selected from the following compound groups.

[0177] [Chemical formula 12-1]

[0178]

[0179] [Chemical formula 12-2]

[0180]

[0181] In a preferred embodiment of the present invention, the compound represented by the general formula (1) is selected from the following compound groups.

[0182] [Chemical formula 13]

[0183]

[0184] Regarding the molecular weight of the compound represented by the general formula (1), for example, when attempting to form a film of an organic layer containing the compound represented by the general formula (1) by vapor deposition, it is preferably 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1).

[0185] The compound represented by the general formula (1) can be formed into a film by a coating method regardless of its molecular weight. If the coating method is used, even a compound with a relatively large molecular weight can be formed into a film. The compound represented by the general formula (1) has advantages such as being easily soluble in organic solvents. Therefore, the compound represented by the general formula (1) is easily applicable to the coating method and is easily purified to increase the purity.

[0186] It is also possible to consider applying the present invention and using a compound containing multiple structures represented by the general formula (1) in the molecule as a light-emitting material.

[0187] For example, it is possible to consider using, as a luminescent material, a polymer obtained by pre - existing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group. For example, it is possible to consider preparing a monomer containing a polymerizable functional group at any position in the general formula (1), obtaining a polymer having a repeating unit by polymerizing it alone or copolymerizing it with other monomers, and using this polymer as a luminescent material. Alternatively, it is also possible to consider obtaining a dimer or trimer by coupling compounds having the structure represented by the general formula (1) with each other and using these as luminescent materials.

[0188] As an example of a polymer having a repeating unit containing the structure represented by the general formula (1), a polymer containing the structure represented by any one of the following two general formulas can be cited.

[0189] [Chemical formula 14]

[0190]

[0191] In the above general formula, Q represents a group containing the structure represented by the general formula (1), and L 1 and L 2 represent a linking group. The number of carbon atoms of the linking group is preferably 0 to 20, more preferably 1 to 15, and further preferably 2 to 10. The linking group is preferably a linking group having a structure represented by -X 11 -L 11 -. Here, X 11 represents an oxygen atom or a sulfur atom, preferably an oxygen atom. L 11 represents a linking group, preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group.

[0192] In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represent a substituent. Preferably, they are a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, a chlorine atom, and further preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms.

[0193] L 1 and L 2The represented linking group can bond to any site in the general formula (1) constituting Q. Two or more linking groups can be connected to one Q to form a crosslinked structure or a network structure.

[0194] As a specific structural example of the repeating unit, the structure represented by the following formula can be cited.

[0195] [Chemical formula 15]

[0196]

[0197] A polymer having repeating units containing these formulas can be synthesized as follows: A hydroxyl group is introduced into any site in the general formula (1), and the following compound is reacted using this as a linking group to introduce a polymerizable group, and the polymerizable group is polymerized.

[0198] [Chemical formula 16]

[0199]

[0200] The polymer containing the structure represented by the general formula (1) in the molecule can be a polymer composed only of repeating units having the structure represented by the general formula (1), or can be a polymer containing repeating units having other structures. And, the repeating units having the structure represented by the general formula (1) contained in the polymer can be a single type or two or more types. As the repeating units not having the structure represented by the general formula (1), repeating units derived from monomers usually used for copolymerization can be cited. For example, repeating units derived from monomers having an ethylenic unsaturated bond such as ethylene and styrene can be cited.

[0201] In one embodiment, the compound represented by the general formula (1) is a luminescent material.

[0202] In one embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence.

[0203] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the UV region, the blue, green, yellow, orange, red regions (for example, about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) in the visible spectrum, or the near-infrared region.

[0204] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the red or orange region (for example, about 620 nm to about 780 nm, about 650 nm) in the visible spectrum.

[0205] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the orange or yellow region (for example, about 570 nm to about 620 nm, about 590 nm, about 570 nm) of the visible spectrum.

[0206] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the green region (for example, about 490 nm to about 575 nm, about 510 nm) of the visible spectrum.

[0207] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the blue region (for example, about 400 nm to about 490 nm, about 475 nm) of the visible spectrum.

[0208] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the ultraviolet spectral region (for example, 280 - 400 nm).

[0209] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the infrared spectral region (for example, 780 nm to 2 μm).

[0210] In one embodiment of the present invention, an organic semiconductor element using the compound represented by the general formula (1) can be fabricated. The organic semiconductor element described herein can be an organic optical element involving light or an organic element not involving light. The organic optical element can be an organic light-emitting element that emits light, an organic light-receiving element that receives light, or an element in which energy transfer occurs due to light within the element. In one embodiment of the present invention, an organic optical element such as an organic electroluminescent element or a solid-state imaging element (for example, a CMOS image sensor) can be fabricated using the compound represented by the general formula (1). In one embodiment of the present invention, a CMOS (complementary metal oxide semiconductor) etc. using the compound represented by the general formula (1) can be fabricated.

[0211] The electronic properties of a chemical library of small molecules can be calculated using quantum chemical calculations based on known ab initio. For example, as a basis set, the time-dependent density functional theory using a functional group known as 6-31G* and the three-parameter Becke and Lee-Yang-Parr hybrid functional is used to analyze the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*), and molecular fragments (parts) having a HOMO above a specific threshold and a LUMO below a specific threshold can be screened.

[0212] Thus, when there is a HOMO energy (e.g., ionization potential) of more than -6.5 eV, for example, a donor moiety ("D") can be selected. Also, when there is a LUMO energy (e.g., electron affinity) of -0.5 eV or less, for example, an acceptor moiety ("A") can be selected. The bridge moiety ("B") is, for example, a strong conjugated system that can strictly confine the acceptor and donor moieties to a unique three-dimensional structure, thereby preventing overlap between the π-conjugated systems of the donor and acceptor moieties.

[0213] In one embodiment, the compound library is screened using one or more of the following properties.

[0214] 1. Emission near a specific wavelength

[0215] 2. A triplet state higher than a calculated specific energy level

[0216] 3. A ΔE lower than a specific value ST Value

[0217] 4. A quantum yield higher than a specific value

[0218] 5. HOMO level

[0219] 6. LUMO level

[0220] In one embodiment, the difference (ΔE ST ) between the lowest excited singlet state and the lowest excited triplet state at 77 K is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, the ΔE ST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV.

[0221] In one embodiment, the compound represented by the general formula (1) exhibits a quantum yield of more than 25%, such as about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or more.

[0222] [Synthesis method of the compound represented by the general formula (1)]

[0223] The compound represented by the general formula (1) includes novel compounds.

[0224] The compound represented by the general formula (1) can be synthesized by combining known reactions. For example, by reacting a substituted or unsubstituted aryl group (e.g., phenyl) and a cyanobenzene having a halogen atom with a substituted ring-fused carbazol-9-yl group, a compound of the general formula (1) substituted with a substituted ring-fused carbazol-9-yl group can be synthesized. For the detailed content of the reaction conditions, reference can be made to the synthesis examples described later.

[0225] [Structure using the compound represented by the general formula (1)]

[0226] In one embodiment, one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that are combined with the compound represented by the general formula (1) to disperse the compound, covalently bond to the compound, coat the compound, support the compound, or associate with the compound are used together to form a solid film or layer. For example, a film can be formed by combining the compound represented by the general formula (1) with an electroactive material. In some cases, the compound represented by the general formula (1) can also be combined with a hole-transporting polymer. In some cases, the compound represented by the general formula (1) can also be combined with an electron-transporting polymer. In some cases, the compound represented by the general formula (1) can also be combined with a hole-transporting polymer and an electron-transporting polymer. In some cases, the compound represented by the general formula (1) can also be combined with a copolymer having both a hole-transporting part and an electron-transporting part. Through the above embodiments, electrons and / or holes formed in the solid film or layer can interact with the compound represented by the general formula (1).

[0227] [Formation of film]

[0228] In one embodiment, a film containing the compound represented by the general formula (1) can be formed by a wet process. In the wet process, a solution obtained by dissolving a composition containing the compound of the present invention is coated on a surface, and after removing the solvent, a film is formed. Examples of the wet process include spin coating, slot coating, inkjet printing (spray coating), gravure printing, offset printing, and flexographic printing, but are not limited thereto. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected. In one embodiment, a substituent (e.g., an alkyl group) that improves the solubility in an organic solvent can be introduced into the compound contained in the composition.

[0229] In one embodiment, a film containing the compound of the present invention can be formed by a dry process. In one embodiment, as the dry process, a vacuum evaporation method can be employed, but it is not limited thereto. In the case of using the vacuum evaporation method, the compounds constituting the film can be co-evaporated from separate evaporation sources, or can be co-evaporated from a single evaporation source mixed with the compounds. In the case of using a single evaporation source, a mixed powder containing a powder of the compound can be used, a compression molded body obtained by compressing the mixed powder can be used, or a mixture obtained by heating and melting each compound and then cooling can be used. In one embodiment, co-evaporation is performed under the condition that the evaporation rates (weight reduction rates) of the plurality of compounds contained in the single evaporation source are the same or substantially the same, whereby a film having a composition ratio corresponding to the composition ratio of the plurality of compounds contained in the evaporation source can be formed. If a plurality of compounds are mixed as an evaporation source in the same composition ratio as the composition ratio of the formed film, a film having a desired composition ratio can be easily formed. In one embodiment, the temperature at which each compound for co-evaporation has the same weight reduction rate can be determined, and this temperature can be adopted as the temperature during co-evaporation.

[0230] [Example of use of the compound represented by the general formula (1)]

[0231] The compound represented by the general formula (1) is used as a material for an organic light-emitting element. In particular, it is preferably used in an organic light-emitting diode or the like.

[0232] Organic light-emitting diode:

[0233] One aspect of the present invention relates to the use of the compound represented by the general formula (1) of the present invention in the form of a light-emitting material of an organic light-emitting device. In one embodiment, the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In one embodiment, the compound represented by the general formula (1) contains delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed phosphor having a structure represented by the general formula (1). In one embodiment, the present invention relates to the use of the compound represented by the general formula (1) as a delayed phosphor. In one embodiment, the compound represented by the general formula (1) of the present invention can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting materials can be fluorescent materials, phosphorescent materials, or TADF. In one embodiment, the compound represented by the general formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by the general formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from the compound represented by the general formula (1). In one embodiment, an organic light-emitting device containing a compound as a light-emitting material emits delayed fluorescence and exhibits high luminous efficiency.

[0234] In one embodiment, the light-emitting layer contains a compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is the film-forming surface. In one embodiment, the orientation of the compound represented by the general formula (1) on the film-forming surface affects or determines the propagation direction of the light emitted by the arranged compound. In one embodiment, by arranging in the propagation direction of the light emitted by the compound represented by the general formula (1), the light extraction efficiency from the light-emitting layer is improved.

[0235] One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes a light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by the general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by the general formula (1) assists the luminescence of other light-emitting materials contained in the light-emitting layer (as a so-called co-dopant). In one embodiment, the compound represented by the general formula (1) contained in the light-emitting layer is in its lowest excited singlet state energy level, which is included between the lowest excited singlet state energy level of the host material contained in the light-emitting layer and the lowest excited singlet state energy level of another light-emitting material contained in the light-emitting layer.

[0236] In one embodiment, the organic photoluminescence device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least a light-emitting layer. In one embodiment, the organic layer only includes a light-emitting layer. In one embodiment, the organic layer includes more than one organic layer other than the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In one embodiment, the hole transport layer can be a hole injection and transport layer having a hole injection function, and the electron transport layer can be an electron injection and transport layer having an electron injection function.

[0237] Light-emitting layer:

[0238] In one embodiment, the light-emitting layer is a layer in which holes and electrons injected from the anode and the cathode are re-bonded to form excitons. In one embodiment, the layer emits light.

[0239] In one embodiment, only a luminescent material is used as the light-emitting layer. In one embodiment, the light-emitting layer contains a luminescent material and a host material. In one embodiment, the luminescent material is one or more compounds represented by the general formula (1). In one embodiment, in order to enable an organic electroluminescent device and an organic photoluminescent device to exhibit high luminous efficiency, singlet excitons and triplet excitons generated in the luminescent material are confined in the luminescent material. In one embodiment, in addition to the luminescent material, a host material is also used in the light-emitting layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has singlet excitation energy and triplet excitation energy, at least one of which is higher than those of the luminescent material of the present invention. In one embodiment, singlet excitons and triplet excitons generated in the luminescent material of the present invention are confined in the molecules of the luminescent material of the present invention. In one embodiment, the singlet and triplet excitons are confined sufficiently to promote luminous efficiency. In one embodiment, the singlet excitons and triplet excitons are not confined sufficiently, but still a high luminous efficiency is obtained, that is, a host material capable of achieving a high luminous efficiency can be used in the present invention without particular limitation. In one embodiment, light emission occurs in the luminescent material in the light-emitting layer of the device of the present invention. In one embodiment, the emitted light contains both fluorescence and delayed fluorescence. In one embodiment, the emitted light contains light emitted from the host material. In one embodiment, the emitted light consists of light emitted from the host material. In one embodiment, the emitted light contains light emitted from the compound represented by the general formula (1) and light emitted from the host material. In one embodiment, a TADF molecule and a host material are used. In one embodiment, the TADF is a co-dopant, the singlet excitation energy of which is lower than that of the host material in the light-emitting layer and higher than that of the luminescent material in the light-emitting layer.

[0240] When a compound represented by the general formula (1) is used as a co-dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Such luminescent materials can be those using anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, Derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives having metals (Al, Zn), etc. These exemplified skeletons may or may not have substituents. Also, these exemplified skeletons can be combined with each other.

[0241] The following exemplifies luminescent materials that can be used in combination with a co-dopant having the structure represented by the general formula (1).

[0242] [Chemical formula 17-1]

[0243]

[0244] [Chemical formula 17-2]

[0245]

[0246] [Chemical formula 17-3]

[0247]

[0248] Also, it is particularly preferable to use the compound described in paragraphs 0220 to 0239 of WO2015 / 022974 as the luminescent material used in combination with the co-dopant having the structure represented by the general formula (1).

[0249] As a further preferable luminescent material, the compound represented by the following general formula (2) can also be cited.

[0250] [Chemical formula 18]

[0251] General formula (2)

[0252]

[0253] In the general formula (2), R 1 , R 3 to R 16 each independently represent a hydrogen atom, a deuterium atom or a substituent. R 2 represents an acceptor group or R 1 and R 2 are bonded to each other to form an acceptor group or R 2 and R 3 are bonded to each other to form an acceptor group. R 3 and R 4, R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 may bond to each other to form a ring structure. X 1 represents O or NR, and R represents a substituent. X 2 to X 4 in X 3 and X 4 at least one of which may be O or NR and the remaining part may be O or NR, or may not be connected. When not connected, the two ends independently represent a hydrogen atom, a deuterium atom or a substituent. C-R 1 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 , C-R 10 , C-R 11 , C-R 12 , C-R 13 , C-R 14 , C-R 15 , C-R 16 can be substituted by N.

[0254] In one embodiment of the present invention, when X 2 is O or NR, R 7 is a receptor group, R 6 and R 7 bond to each other to form a receptor group or R 7 and R 8 bond to each other to form a receptor group. In one embodiment of the present invention, when X 3 is O or NR, R 10 is a receptor group, R 9 and R 10Bonded to each other to form a receptor group or R 10 and R 11 Bonded to each other to form a receptor group. In one embodiment of the present invention, when X 4 is O or NR, R 15 is a receptor group, R 14 and R 15 Bonded to each other to form a receptor group or R 15 and R 16 Bonded to each other to form a receptor group. In one embodiment of the present invention, when X 2 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 8 , at least one of the 3-position and the 6-position of the carbazole ring is substituted with a receptor group. In one embodiment of the present invention, when X 3 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 9 , at least one of the 3-position and the 6-position of the carbazole ring is substituted with a receptor group. In one embodiment of the present invention, when X 4 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 16 , at least one of the 3-position and the 6-position of the carbazole ring is substituted with a receptor group. In one embodiment of the present invention, when X 1 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 1 , the 3-position of the carbazole ring is substituted with a receptor group (wherein the 3-position is present on the phenyl group). In one embodiment of the present invention, it is a compound represented by the following general formula (2a).

[0255] [Chemical formula 19]

[0256] General formula (2a)

[0257]

[0258] In the general formula (2a), R 1 , R 3 , R 6 ~R 11 , R 14 ~R 16 Each independently represents a hydrogen atom, a deuterium atom or a substituent. R 2 represents a receptor group or R 1 and R 2 Bonded to each other to form a receptor group or R 2 and R 3 Bonded to each other to form a receptor group.

[0259] R 6 and R 7 、R 7 and R 8 、R 9 and R 10 、R 10 and R 11 、R 14 and R 15 、R 15 and R 16 may be bonded to each other to form a cyclic structure. X 1 represents O or NR, and R represents a substituent. X 2 ~X 4 in X 3 and X 4 at least one of which may be O or NR and the remaining part may be O or NR, or may not be connected. When not connected, each end independently represents a hydrogen atom, a deuterium atom or a substituent. Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. C-R in the general formula (2a) 1 、C-R 3 、C-R 6 、C-R 7 、C-R 8 、C-R 9 、C-R 10 、C-R 11 、C-R 14 、C-R 15 、C-R 16 may be substituted with N.

[0260] As a further preferred luminescent material, a compound represented by the following general formula (3) can also be cited.

[0261] [Chemical formula 20]

[0262] General formula (3)

[0263]

[0264] In the general formula (3), R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 3 ~R 16 each independently represents a hydrogen atom, a deuterium atom or a substituent. R 1 and R 3 、R 3 and R 4 、R4 and R 5 、R 5 and R 6 、R 6 and R 7 、R 7 and R 8 、R 8 and R 9 、R 9 and R 2 、R 2 and R 10 、R 10 and R 11 、R 11 and R 12 、R 12 and R 13 、R 13 and R 14 、R 14 and R 15 、R 15 and R 16 、R 16 and R 1 may be bonded to each other to form a cyclic structure. C-R in the general formula (3) 3 、C-R 4 、C-R 5 、C-R 6 、C-R 7 、C-R 8 、C-R 9 、C-R 10 、C-R 11 、C-R 12 、C-R 13 、C-R 14 、C-R 15 、C-R 16 may be replaced by N.

[0265] In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted phenyl group which may be fused with other rings. In one embodiment of the present invention, R 3 and R 10 are each independently a substituted amino group. In one embodiment of the present invention, R 1 and R 3 and R 2 and R 10 at least one combination of them may be bonded to each other to form a cyclic structure. In one embodiment of the present invention, the cyclic structure contains a benzazaborane ring.

[0266] As a further preferred luminescent material, a compound represented by the following general formula (4) can also be mentioned.

[0267] [Chemical Formula 21]

[0268] General formula (4)

[0269]

[0270] In general formula (4), Z 1 and Z 2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R 1 ~R 9 each independently represent a hydrogen atom, a deuterium atom or a substituent. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 may bond to each other to form a ring structure. Among them, Z 1 , Z 2 , R 1 and R 2 bonding to each other to form a ring, R 2 and R 3 bonding to each other to form a ring, R 4 and R 5 bonding to each other to form a ring and R 5 and R 6 bonding to each other to form a ring, at least one of which is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyrrole ring of a substituted or unsubstituted indole, and at least one of R 1 ~R 9 is a substituted or unsubstituted aryl or acceptor group or a ring in which at least one of Z 1 and Z 2 has an aryl or acceptor group as a substituent. The carbon atoms in the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring that can be substituted can be substituted by nitrogen atoms. C-R in general formula (4) 1 , C-R 2 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7, C-R 8 , C-R 9 may be substituted with N.

[0271] In one embodiment of the present invention, Z 1 and Z 2 are each independently an unsubstituted or substituted non-fused benzene ring, a furan ring fused with an unsubstituted or substituted benzene ring, a thiophene ring fused with an unsubstituted or substituted benzene ring, or a pyrrole ring fused with an unsubstituted or substituted benzene ring. In one embodiment of the present invention, R 1 to R 9 are each independently an unsubstituted or substituted aryl group or an acceptor group, or one or more rings selected from the group consisting of a ring formed by bonding R 1 and R 2 to each other, a ring formed by bonding R 2 and R 3 to each other, a ring formed by bonding R 4 and R 5 to each other, and a ring formed by bonding R 5 and R 6 to each other are an unsubstituted or substituted furan ring fused with a benzene ring, an unsubstituted or substituted thiophene ring fused with a benzene ring, or an unsubstituted or substituted pyrrole ring fused with a benzene ring. In one embodiment of the present invention, R 8 is an unsubstituted or substituted aryl group or an acceptor group. In one embodiment of the present invention, it contains two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.

[0272] As a further preferred luminescent material, there can be mentioned a compound in which a carbon-carbon bond a having the following structure α is fused with a furan ring constituting an unsubstituted or substituted benzofuran ring, a thiophene ring constituting an unsubstituted or substituted benzothiophene ring, or a pyrrole ring constituting an unsubstituted or substituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting an unsubstituted or substituted dibenzofuran ring, a benzene ring constituting an unsubstituted or substituted dibenzothiophene ring, a benzene ring constituting an unsubstituted or substituted carbazole ring, or a benzene ring constituting an unsubstituted or substituted dibenzodioxane ring to form a fused ring structure A (the hydrogen atoms in the structure may be replaced by deuterium atoms or substituents).

[0273] [Chemical formula 22]

[0274] Structure a

[0275]

[0276] In structure α, X 1 and X 2Each independently represents a substituted or unsubstituted aryl group, or a nitrogen atom or an oxygen atom formed by bonding of substituted or unsubstituted aryl groups. Z represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, and Z and X 2 may bond to each other to form a cyclic structure.

[0277] In the fused ring structure A, the structure fused with b, the structure fused with X 1 , b, and Z, Z and X 2 may bond to each other to form a cyclic structure.

[0278] As a further preferred luminescent material, a compound represented by the following general formula (5) can also be cited.

[0279] [Chemical formula 23]

[0280] General formula (5)

[0281]

[0282] In general formula (5), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring. Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R 1 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 may bond to each other to form a cyclic structure. Among them, at least one group of R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 bonds to each other to form a cyclic structure.

[0283] As a further preferred luminescent material, a compound represented by the following general formula (6) can also be cited.

[0284] [Chemical formula 24]

[0285] General formula (6)

[0286]

[0287] In general formula (6), X 3 represents an oxygen atom or a sulfur atom, and Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R 1 and R 4 ~R 7 represent a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 can bond to each other to form a cyclic structure. Among them, at least one group of R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 bond to each other to form a cyclic structure.

[0288] As a further preferred luminescent material, a compound represented by the following general formula (7) can also be cited.

[0289] [Chemical formula 25]

[0290] General formula (7)

[0291]

[0292] In general formula (7), X 4 represents an oxygen atom or a sulfur atom, and Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R 1 and R 4a ~R 7a represent a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3Each independently represents a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl. R 2 and Z 2 、Z 2 and Z 3 、Z 3 and R 3 、R 4a and R 5a 、R 5a and R 6a 、R 6a and R 7a 、R 7a and R 1 may bond to each other to form a cyclic structure. Among them, at least one group of R 2 and Z 2 、Z 2 and Z 3 、Z 3 and R 3 bond to each other to form a cyclic structure.

[0293] As a further preferred luminescent material, a compound represented by the following general formula (8) can also be cited.

[0294] [Chemical formula 26]

[0295] General formula (8)

[0296]

[0297] In general formula (8), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 8 ~R 14 each independently represents a hydrogen atom, a deuterium atom or a substituent, R 3 represents a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl. Z 1 and R 1 、R 8 and R 9 、R 9 and R 10 、R 10 and R 11 、R 11 and R 12 、R 12 and R 13 、R 13 and R 14, R 14 and Z 3 , Z 3 and R 3 may bond to each other to form a cyclic structure.

[0298] As a further preferred luminescent material, a compound represented by the following general formula (9) can also be cited.

[0299] [Chemical formula 27]

[0300] General formula (9)

[0301]

[0302] In general formula (9), Z 1 and Z 4 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring. Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 15 ~R 17 each independently represent a hydrogen atom, a deuterium atom or a substituent, and R 3 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and Z 3 , Z 3 and R 3 may bond to each other to form a cyclic structure.

[0303] As a further preferred luminescent material, a compound represented by the following general formula (10) can also be cited.

[0304] [Chemical formula 28]

[0305] General formula (10)

[0306]

[0307] In general formula (10), Z 1 and Z 5Each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 、R 2 and Z 5 、Z 5 and Z 3 、Z 3 and R 3 can bond to each other to form a cyclic structure. Among them, R 2 and Z 2 、Z 2 and Z 3 、Z 3 and R 3 in at least one group bond to each other to form a cyclic structure.

[0308] As a further preferred luminescent material, a compound represented by the following general formula (11) can also be cited.

[0309] [Chemical formula 29]

[0310] General formula (11)

[0311]

[0312] In the general formula (11), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 21 ~R 27 each independently represent a hydrogen atom, a deuterium atom or a substituent, R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 、R 2 and Z 2 、Z 2 and R 21 、R 21 and R 22 、R22 and R 23 、R 23 and R 24 、R 24 and R 25 、R 25 and R 26 、R 26 and R 27 can be bonded to each other to form a ring structure.

[0313] As a further preferred luminescent material, a compound represented by the following general formula (12) can also be cited.

[0314] [Chemical formula 30]

[0315] General formula (12)

[0316]

[0317] In general formula (12), Z 1 and Z 6 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 28 ~R 30 each independently represents a hydrogen atom, a deuterium atom or a substituent, R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 、R 2 and Z 2 、Z 2 and R 28 、R 28 and R 29 、R 29 and R 30 、R 30 and Z 6 can be bonded to each other to form a cyclic structure.

[0318] As a further preferred luminescent material, a compound represented by the following general formula (13) can also be cited.

[0319] [Chemical formula 31]

[0320] General formula (13)

[0321]

[0322] In general formula (13), Z1 and Z 7 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 、R 2 and Z 2 、Z 2 and Z 7 、Z 7 and R 3 may be bonded to each other to form a cyclic structure. Among them, R 2 and Z 2 、Z 2 and Z 7 、Z 7 and R 3 in at least one group of them are bonded to each other to form a cyclic structure.

[0323] As a further preferred luminescent material, the compound represented by the following general formula (14) can also be cited.

[0324] [Chemical formula 32]

[0325] General formula (14)

[0326]

[0327] In the general formula (14), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, R 1 and R 31 ~R 44 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 、R 31 and R 32 、R 32 and R 33 、R 33 and R 34 、R 34 and R 35 、R 35 and R36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , R 42 and R 43 , R 43 and R 44 can be bonded to each other to form a cyclic structure.

[0328] As a further preferred luminescent material, a compound represented by the following general formula (15) can also be cited.

[0329] [Chemical formula 33]

[0330] General formula (15)

[0331]

[0332] In the general formula (15), Z 1 , and Z 8 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and R 1 and R 51 ~R 60 each independently represents a hydrogen atom, a deuterium atom, or a substituent. R 1 and Z 1 , R 51 and R 52 , R 52 and R 53 , R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 , R 60 and Z 8 can be bonded to each other to form a cyclic structure.

[0333] As a further preferred luminescent material, a compound represented by the following general formula (16) can also be cited.

[0334] [Chemical formula 34]

[0335] General formula (16)

[0336]

[0337] In general formula (16), Z 1 , Z 8 and Z 9 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring. R 1 and R 61 ~R 66 each independently represent a hydrogen atom, a deuterium atom or a substituent. R 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , R 66 and Z 8 can bond to each other to form a ring structure.

[0338] As a further preferred luminescent material, a compound represented by the following general formula (17) can also be cited.

[0339] [Chemical formula 35]

[0340] General formula (17)

[0341]

[0342] In general formula (17), Z 1 , Z 9 and Z 10 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring. R 1 and R 67 ~R 69 each independently represent a hydrogen atom, a deuterium atom or a substituent, R 70Represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 、Z 9 and R 67 、R 67 and R 68 、R 68 and R 69 、R 69 and Z 10 、Z 10 and R 70 may be bonded to each other to form a cyclic structure.

[0343] As a further preferred luminescent material, a compound represented by the following general formula (18) may also be mentioned.

[0344] [Chemical formula 36]

[0345] General formula (18)

[0346]

[0347] In general formula (18), Z 1 、Z 11 and Z 12 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and R 1 and R 72 ~R 74 each independently represent a hydrogen atom, a deuterium atom or a substituent, and R 71 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 、R 71 and Z 11 、Z 11 and R 72 、R 72 and R 73 、R 73 and Z 74 、R 74 and Z 12 may be bonded to each other to form a ring structure.

[0348] As a further preferred luminescent material, a compound represented by the following general formula (19) may also be mentioned.

[0349] [Chemical formula 37]

[0350] General formula (19)

[0351]

[0352] In general formula (19), Z 1 and Z 11 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, R 1 and R 76 ~R 82 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 75 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 、R 75 and Z 11 、Z 11 and R 76 、R 76 and R 77 、R 77 and R 78 、R 78 and R 79 、R 79 and R 80 、R 80 and R 81 、R 81 and R 82 may bond to each other to form a ring structure.

[0353] As a further preferred luminescent material, a compound represented by the following general formula (20) can also be cited.

[0354] [Chemical formula 38]

[0355] General formula (20)

[0356]

[0357] In general formula (20), X 5 represents an oxygen atom, a sulfur atom, or a nitrogen atom bonded by a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 101 ~R 130 each independently represent a hydrogen atom, a deuterium atom or a substituent, R 101 and R 102 、R 102 and R 103 、R 103 and R 104 、R 104 and R 105 、R 105 and R 106 、R106 and R 107 、R 107 and R 108 、R 108 and R 109 、R 109 and R 110 、R 110 and R 111 、R 111 and R 112 、R 112 and R 113 、R 113 and R 114 、R 114 and R 115 、R 115 and R 116 、R 116 and R 117 、R 117 and R 118 、R 118 and R 119 、R 119 and R 120 、R 120 and R 121 、R 121 and R 122 、R 122 and R 123 、R 123 and R 124 、R 124 and R 125 、R 125 and R 126 、R 126 and R 127 、R 127 and R 128 、R 128 and R 129 、R 129 and R 130 、R 130 and R 101 may bond to each other to form a cyclic structure.

[0358] As a further preferred luminescent material, a compound represented by the following general formula (21) may also be mentioned.

[0359] [Chemical formula 39]

[0360] General formula (21)

[0361]

[0362] In general formula (21), R 1 and R 2Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Z 1 and Z 2 Each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 3 ~R 9 Each independently represents a hydrogen atom, a deuterium atom, or a substituent. Among them, R 1 , R 2 , Z 1 and Z 2 At least one of them contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. R 1 and Z 1 , Z 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and Z 2 , Z 2 and R 2 , R 2 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 can be bonded to each other to form a cyclic structure. The carbon atoms in the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring that can be substituted can be substituted by nitrogen atoms. C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 in the general formula (21) can be substituted by N.

[0363] In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. In one embodiment of the present invention, Z 1 and Z 2Each independently is a substituted or unsubstituted non-fused benzene ring, a furan ring fused by substituted or unsubstituted benzene rings, a thiophene ring fused by substituted or unsubstituted benzene rings, a pyrrole ring fused by substituted or unsubstituted benzene rings, a benzene ring fused by substituted or unsubstituted benzofuran rings, a benzene ring fused by substituted or unsubstituted benzothiophene rings, or a benzene ring fused by substituted or unsubstituted indole rings. In one embodiment of the present invention, R 1 and Z 1 bond to each other to form a cyclic structure. In one embodiment of the present invention, R 1 and Z 1 bond to each other to form a pyrrole ring.

[0364] As a further preferred luminescent material, a compound represented by the following general formula (22) can also be mentioned.

[0365] [Chemical formula 40]

[0366] General formula (22)

[0367]

[0368] In the general formula (22), one of X 1 and X 2 is a nitrogen atom, and the other is a boron atom. R 1 ~R 26 , A 1 , A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R16 and R 17 、R 17 and R 18 、R 18 and R 19 、R 19 and R 20 、R 20 and R 21 、R 21 and R 22 、R 22 and R 23 、R 23 and R 24 、R 24 and R 25 、R 25 and R 26 can be bonded to each other to form a ring structure. Among them, when X 1 is a nitrogen atom, R 17 and R 18 are bonded to each other to form a single bond to form a pyrrole ring. When X 2 is a nitrogen atom, R 21 and R 22 are bonded to each other to form a single bond to form a pyrrole ring. Among them, when X 1 is a nitrogen atom, R 7 and R 8 and R 21 and R 22 are bonded via a nitrogen atom to form a 6-membered ring. When R 17 and R 18 are bonded to each other to form a single bond, at least one of R 1 ~R 6 is a substituted or unsubstituted aryl group or any one of R 1 and R 2 、R 2 and R 3 、R 3 and R 4 、R 4 and R 5 、R 5 and R 6 are bonded to each other to form an aromatic ring or a heteroaromatic ring.

[0369] In one embodiment of the present invention, at least one of R 3 and R 6 is a substituent. In one embodiment of the present invention, both R 3 and R 6 are substituents. In one embodiment of the present invention, both R 3 and R 6The substituents represented are a group selected from the group consisting of an alkyl group and an aryl group or a group obtained by combining two or more thereof. In one embodiment of the present invention, R 8 and R 12 are both substituents. In one embodiment of the present invention, it is represented by the following general formula (22a).

[0370] [Chemical formula 41]

[0371] General formula (22a)

[0372]

[0373] In the general formula (22a), Ar 1 to Ar 4 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 41 and R 42 each independently represent a substituted or unsubstituted alkyl group. m1 and m2 each independently represent an integer from 0 to 5, n1 and n3 each independently represent an integer from 0 to 4, and n2 and n4 each independently represent an integer from 0 to 3. A 1 , A 2 each independently represent a hydrogen atom, a deuterium atom or a substituent.

[0374] In one embodiment of the present invention, A 1 and A 2 are each independently a group having a Hammett σp value greater than 0.2. In one embodiment of the present invention, A 1 and A 2 are both cyano groups. In one embodiment of the present invention, A 1 and A 2 are both halogen atoms. In one embodiment of the present invention, it has a rotationally symmetric structure.

[0375] Hereinafter, preferred specific examples of the compound having the condensed ring structure A and the compound represented by any one of the general formulas (5) to (22) are given.

[0376] [Chemical formula 42-1]

[0377]

[0378] [Chemical formula 42-2]

[0379]

[0380] [Chemical formula 42-3]

[0381]

[0382] [Chemical formula 42-4]

[0383]

[0384] [Chemical Formula 42-5]

[0385]

[0386] [Chemical Formula 42-6]

[0387]

[0388] [Chemical Formula 42-7]

[0389]

[0390] [Chemical Formula 42-8]

[0391]

[0392] [Chemical Formula 42-9]

[0393]

[0394] [Chemical Formula 43-1]

[0395]

[0396] [Chemical Formula 43-2]

[0397]

[0398] [Chemical Formula 44-1]

[0399]

[0400] [Chemical Formula 44-2]

[0401]

[0402] In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 0.1 wt% or more. In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 1 wt% or more. In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 50 wt% or less. In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 20 wt% or less. In one embodiment, when a host material is used, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 10 wt% or less.

[0403] In one embodiment, the host material in the light-emitting layer is an organic compound having a hole-transporting function and an electron-transporting function. In one embodiment, the host material in the light-emitting layer is an organic compound that prevents an increase in the wavelength of the emitted light. In one embodiment, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0404] In some embodiments, the host material is selected from the group consisting of:

[0405] [Chemical formula 45-1]

[0406]

[0407] [Chemical formula 45-2]

[0408]

[0409] In one embodiment, the light-emitting layer contains two or more TADF molecules having different structures. For example, a light-emitting layer can be provided that contains these three materials in which the singlet excitation energy levels are high in the order of the host material, the first TADF molecule, and the second TADF molecule. At this time, the difference δE between the lowest singlet excitation energy level of the first TADF molecule and the second TADF molecule and the lowest triplet excitation energy level at 77K STAll are preferably below 0.3 eV, more preferably below 0.25 eV, still more preferably below 0.2 eV, even more preferably below 0.15 eV, further preferably below 0.1 eV, still further preferably below 0.07 eV, yet further preferably below 0.05 eV, and even further preferably below 0.03 eV, and particularly preferably below 0.01 eV. The concentration of the first TADF molecule in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. Also, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. The concentration of the first TADF molecule in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition in the light-emitting layer may be set as follows: the host material is 10 to 70% by weight, the first TADF molecule is 10 to 80% by weight, and the second TADF molecule is 0.1 to 30% by weight. In one embodiment, the composition in the light-emitting layer may be set as follows: the host material is 20 to 45% by weight, the first TADF molecule is 50 to 75% by weight, and the second TADF molecule is 5 to 20% by weight. In one embodiment, the photoluminescence quantum yield φPL1(A) based on photoexcitation of the co-evaporated film of the first TADF molecule and the host material (the concentration of the first TADF molecule in this co-evaporated film = A% by weight) and the photoluminescence quantum yield φPL2(A) based on photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-evaporated film = A% by weight) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photoluminescence quantum yield φPL2(B) based on photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-evaporated film = B% by weight) and the photoluminescence quantum yield φPL2(100) based on photoexcitation of the single film of the second TADF molecule satisfy the relationship φPL2(B) > φPL2(100). In one embodiment, the light-emitting layer can contain three TADF molecules with different structures. The compound of the present invention can be any one of the multiple TADF compounds contained in the light-emitting layer.

[0410] In one embodiment, the light-emitting layer can be composed of materials selected from the group consisting of a host material, a co-dopant, and a luminescent material. In one embodiment, the light-emitting layer does not contain a metal element. In one embodiment, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. Alternatively, the light-emitting layer can also be composed of a material consisting only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and an oxygen atom. Alternatively, the light-emitting layer can also be composed of a material consisting only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, and an oxygen atom.

[0411] When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescence material. Preferred delayed fluorescence materials may include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, paragraphs 0008 to 0071 and 0118 to 0133 of WO2013 / 081088, paragraphs 0009 to 0046 and 0093 to 0134 of JP-A-2013-256490, paragraphs 0008 to 0020 and 0038 to 0040 of JP-A-2013-116975, paragraphs 0007 to 0032 and 0079 to 0084 of WO2013 / 133359, paragraphs 0008 to 0054 and 0101 to 0121 of WO2013 / 161437, paragraphs 0007 to 0041 and 0060 to 0069 of JP-A-2014-9352, paragraphs 0008 to 0048 and 0067 to 0076 of JP-A-2014-9224, paragraphs 0013 to 0025 of JP-A-2017-119663, paragraphs 0013 to 0026 of JP-A-2017-119664, paragraphs 0012 to 0025 of JP-A-2017-222623, paragraphs 0010 to 0050 of JP-A-2017-226838, paragraphs 0012 to 0043 of JP-A-2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, compounds contained in the general formulas described therein, especially exemplified compounds capable of emitting delayed fluorescence.Moreover, it is preferable to use a luminescent material described in Japanese Patent Application Laid-Open No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO2015 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japanese Patent Application Laid-Open No. 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, WO2015 / 159541, which can emit delayed fluorescence. In addition, the above-mentioned gazettes described in this paragraph are incorporated herein by reference as part of this specification. Moreover, it is also preferable to use the following delayed fluorescence materials.

[0412] [Chemical formula 46]

[0413]

[0414] Hereinafter, each component of the organic electroluminescent element and each layer other than the light-emitting layer will be described.

[0415] Substrate:

[0416] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, where the substrate is not particularly limited and can be any of those substrates that have been commonly used in organic electroluminescent elements, such as those substrates formed of glass, transparent plastic, quartz, and silicon.

[0417] Anode:

[0418] In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a relatively large work function (above 4 eV). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material can be selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material such as IDIXO (In2O3-ZnO) that can form a transparent conductive film is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is fabricated by evaporation or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, when high precision of the pattern is not required (e.g., above about 100 μm), the pattern can be formed using a mask with a desired shape during evaporation or sputtering of 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 and coating are used. In some embodiments, when the emitted light passes through the anode, the transmittance of the anode is greater than 10%, and the sheet resistance of the anode is several hundred ohms per square or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0419] Cathode:

[0420] In some embodiments, the cathode is made of an electrode material such as a metal with a small work function (below 4 eV) (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 metals. In some embodiments, a mixture of an electron injection metal and a second metal is used, where the second metal is a stable metal with a larger work function than the electron injection metal. 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 increases the electron injection characteristics and the durability against oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film by evaporation or sputtering. In some embodiments, the sheet resistance of the cathode is several hundred ohms per square or less. In some embodiments, the thickness of the cathode is in the range of 10 nm to 5 μm. In some embodiments, the thickness of the cathode is in the range of 50 to 200 nm. In some embodiments, in order to transmit the emitted light, either the anode or the cathode of the organic electroluminescent element is transparent or semi-transparent. In some embodiments, the transparent or semi-transparent electroluminescent element enhances the emission brightness.

[0421] In some embodiments, the cathode is formed of a conductive transparent material as described for the anode to form a transparent or semi-transparent cathode. In some embodiments, the element includes both a transparent or semi-transparent anode and a cathode.

[0422] Injection layer:

[0423] 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 emission brightness. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the light-emitting layer or the hole transport layer, and between the cathode and the light-emitting layer or the electron transport layer. In some embodiments, there is an injection layer. In some embodiments, there is no injection layer.

[0424] The following includes preferred compound examples that can be used as hole injection materials.

[0425] [Chemical formula 47]

[0426] MoO3,

[0427]

[0428] Next, preferred compound examples that can be used as an electron injection material are given.

[0429] [Chemical formula 48]

[0430] LiF, CsF,

[0431] Blocking layer:

[0432] The blocking layer is a layer that can suppress the diffusion of charges (electrons or holes) and / or excitons in the light-emitting layer to the outside of the light-emitting layer. In some embodiments, the electron blocking layer is between the light-emitting layer and the hole transport layer, and suppresses electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, the hole blocking layer is between the light-emitting layer and the electron transport layer, and suppresses holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer suppresses the diffusion of excitons to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer form an exciton blocking layer. The term "electron blocking layer" or "exciton blocking layer" used in this specification includes a layer having the functions of both an electron blocking layer and an exciton blocking layer.

[0433] Hole blocking layer:

[0434] The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer suppresses holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material as that described for the electron transport layer.

[0435] The following includes preferred compound examples that can be used for the hole blocking layer.

[0436] [Chemical formula 49]

[0437]

[0438] Electron blocking layer:

[0439] Holes are transported by the electron blocking layer. In some embodiments, the electron blocking layer suppresses electrons from reaching the hole transport layer while transporting holes. 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 can be the same material as that described for the hole transport layer.

[0440] The following includes specific examples of preferred compounds that can be used as an electron blocking material.

[0441] [Chemical formula 50]

[0442]

[0443] Exciton blocking layer:

[0444] The exciton blocking layer inhibits the diffusion of excitons generated by the rebonding of holes and electrons in the light-emitting layer into the electron transport layer. In some embodiments, the exciton blocking layer enables effective confinement of excitons in the light-emitting layer. In some embodiments, the light-emitting efficiency of the device is enhanced. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side and the cathode side or on both sides. In some embodiments, when the exciton blocking layer is on the anode side, the layer may be between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, the layer may be between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or the same layer is between the anode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or the same layer is between the cathode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer includes singlet excitation energy and triplet excitation energy, at least one of which is higher than the singlet excitation energy and triplet excitation energy of the light-emitting material, respectively.

[0445] Hole transport layer:

[0446] The hole transport layer contains 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.

[0447] In some embodiments, the hole transport material has one of the characteristics of hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include (but are not limited to) triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, chalcone derivatives substituted with amino groups, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers) or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amines, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. The following includes specific examples of preferred compounds that can be used as hole transport materials.

[0448] [Chemical Formula 51]

[0449]

[0450] Electron transport layer:

[0451] 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.

[0452] In some embodiments, the electron transport material only needs to have the function of transporting electrons, which is injected from the cathode into the light-emitting layer. In some embodiments, the electron transport material also functions as a hole blocking material. Examples of electron transport layers that can be used in the present invention include (but are not limited to) fluorene derivatives substituted with nitro groups, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenediylmethane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, or combinations thereof or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymeric material. The following includes specific examples of preferred compounds that can be used as electron transport materials.

[0453] [Chemical Formula 52]

[0454]

[0455] In addition, examples of compounds that are more preferably used as materials that can be added to each organic layer are included. For example, addition as a stabilizing material can be considered, etc.

[0456] [Chemical Formula 53]

[0457]

[0458] Specific examples of preferred materials that can be used in the organic electroluminescent element are illustrated, but the materials that can be used in the present invention should not be construed as being limited to the following exemplified compounds. Also, even compounds exemplified as materials having specific functions can be used as materials having other functions.

[0459] Device:

[0460] In some embodiments, the light-emitting layer is incorporated into the device. For example, the device includes an OLED bulb, an OLED lamp, a television screen, a computer monitor, a mobile phone, and a tablet computer, but is not limited to these.

[0461] In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer containing a light-emitting layer between the anode and the cathode.

[0462] In some embodiments, the compositions described in this specification can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be suitable for promoting charge transfer or energy transfer within the device and / or can be used as hole transport materials. The devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic photodetectors, organic photosensors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0463] Light bulb or lamp:

[0464] In some embodiments, an electronic device includes an OLED that includes an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode.

[0465] In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, or blue (e.g., orange and yellowish green). In some embodiments, the combination of OLEDs is a combination of two, four, or more than four colors.

[0466] In some embodiments, the device is an OLED lamp, and the OLED lamp includes:

[0467] A circuit board having a first surface with a mounting surface and a second surface opposite thereto, and defining at least one opening;

[0468] At least one OLED disposed on the mounting surface and having a structure in which the at least one OLED includes an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode and emits light;

[0469] A housing for the circuit board; and

[0470] At least one connector disposed at an end of the housing, and the housing and the connector define a package adapted to be mounted on a lighting device.

[0471] In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is deflected to be emitted in a second direction. In some embodiments, a reflector is used to deflect the light emitted in the first direction.

[0472] Display or screen:

[0473] In some embodiments, the light-emitting layer of the present invention can be used in a screen or a display. In some embodiments, a method including (but not limited to) vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD) is used to deposit the compounds involved in the present invention onto a substrate. In some embodiments, the substrate is a photoplate structure suitable for double-sided etching, providing unique aspect ratio pixels. A screen (which can also be referred to as a mask) is used in the method for manufacturing an OLED display. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and larger sweep angle openings in the horizontal direction. Thereby, it allows for the close patterning of pixels required for a high-definition display while optimizing chemical vapor deposition onto the TFT substrate.

[0474] The internal patterning of the pixels allows for the construction of three-dimensional pixel openings with aspect ratio variations in the horizontal and vertical directions. In addition, imaging "strips" or halftone circles are used within the pixel area to inhibit etching in specific areas until these specific patterns are undercut and removed from the substrate. At this time, all pixel areas are processed at the same etching rate, but the depth varies depending on the halftone pattern. Changing the size and spacing of the halftone pattern allows etching to be inhibited at different rates within the pixel, allowing for local deeper etching required to form steep vertical chamfers.

[0475] A preferred material for the evaporation mask is invar. Invar is a metal alloy cold-rolled into long thin sheets in a steel mill. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming an opening area within the evaporation mask is a wet chemical etching-based method.

[0476] In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is manufactured using lithography (such as photolithography and e-beam lithography). In some embodiments, the screen or display pattern is manufactured using wet chemical etching. In additional embodiments, the screen or display pattern is manufactured using plasma etching.

[0477] Method for manufacturing the device:

[0478] OLED displays are generally manufactured by forming a large mother board and then cutting the mother board into unit board units. Generally, each unit board on the mother board is formed by: forming a thin film transistor (TFT) including a functional layer and source / drain electrodes on a substrate, coating a planarization film on the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting from the mother board.

[0479] In another aspect of the present invention, there is provided a method for manufacturing an organic light-emitting diode (OLED) display, the method comprising:

[0480] a step of forming a barrier layer on a substrate of a mother board;

[0481] a step of forming a plurality of display units in unit board units on the barrier layer;

[0482] a step of forming an encapsulation layer on each of the display units of the unit board; and

[0483] a step of coating an organic film on an interface portion between the unit boards.

[0484] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and an edge portion of the barrier layer is covered with an organic film formed of polyimide or acryloyl. In some embodiments, the organic film helps to gently cut the mother board into unit board units.

[0485] 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 include a thin film transistor (TFT), a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein the organic film coated on 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, with a passivation layer, a planarization film, and an encapsulation layer therebetween, and the encapsulation layer covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film does not contact either the display unit or the encapsulation layer.

[0486] Each of the organic film and the planarization film may include either polyimide or acryloyl group. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the substrate may be formed of polyimide. The method may further include mounting a carrier substrate formed of a glass material onto the other surface of the substrate formed of polyimide before forming a barrier layer on one surface of the substrate formed of polyimide, and separating the carrier substrate from the substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display.

[0487] In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acryloyl group, such as the organic film formed on the edge portion of the barrier layer. In some embodiments, when manufacturing an OLED display, the planarization film and the organic film are formed simultaneously. In some embodiments, the organic film may be formed on the edge portion of the barrier layer such that a part of the organic film directly contacts the substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0488] In some embodiments, the light-emitting layer has a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to the source electrode / drain electrode of the TFT layer.

[0489] In some embodiments, when a voltage is applied to the pixel electrode via the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, whereby the organic light-emitting layer emits light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.

[0490] In some embodiments, an encapsulation layer that covers the display unit and prevents external moisture from penetrating may be formed to have a thin film encapsulation structure in which an organic film and an inorganic film are alternately stacked. In some embodiments, the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are stacked. In some embodiments, the organic film coated on 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 part of the organic film directly contacts the substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0491] In one embodiment, the OLED display is flexible and uses a soft substrate formed of polyimide. In some embodiments, the substrate is formed on a carrier substrate formed of a glass material and then the carrier substrate is separated.

[0492] In some embodiments, a barrier layer is formed on a surface of the substrate on a side opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit panel. For example, while the substrate is formed over the entire surface of the mother board, the barrier layer is formed according to the size of each unit panel, thereby forming a groove at an interface portion between the unit panel barrier layers. Each unit panel can be cut along the groove.

[0493] In some embodiments, the manufacturing method further includes a process of cutting along the interface portion, where a groove is formed in the barrier layer, at least a part of an organic film is formed in the groove, and the groove does not penetrate into the substrate. In some embodiments, a TFT layer of each unit panel is formed, and a passivation layer (i.e., an inorganic film) and a planarization film (i.e., an organic film) are disposed on the TFT layer to cover the TFT layer. While forming the planarization film formed of, for example, polyimide or acryloyl, the groove at the interface portion is covered with an organic film formed of, for example, polyimide or acryloyl. This is when cracking is prevented from occurring by allowing the organic film to absorb the impact that is generated when each unit panel is cut along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the impact generated when each unit panel is cut along the groove at the interface portion is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, since the groove at the interface portion between the barrier layers is covered with the organic film and the organic film absorbs the impact that would otherwise be transferred to the barrier layer, each unit panel can be gently cut and cracking in the barrier layer can be prevented. In one embodiment, the organic film covering the groove at the interface portion is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected to each other as a single layer, since external moisture may penetrate into the display unit via the planarization film and a part where the organic film remains, the organic film is spaced apart from the planarization film so that the organic film is spaced apart from the display unit.

[0494] In some embodiments, a display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother board is completely manufactured, the carrier substrate supporting the substrate is separated from the substrate. In some embodiments, when a laser beam is emitted toward the carrier substrate, the carrier substrate is separated from the substrate due to a difference in the coefficient of thermal expansion between the carrier substrate and the substrate.

[0495] In some embodiments, a mother board is cut into unit board units. In some embodiments, a cutting machine is used to cut the mother board along the interface portion between the unit boards. In some embodiments, since the grooves at the interface portion along which the mother board is cut are covered with an organic film, the organic film absorbs impacts during cutting. In some embodiments, cracking can be prevented from occurring in the barrier layer during cutting.

[0496] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0497] Another aspect is an OLED display, which includes: a barrier layer formed on a substrate; a display unit formed on the barrier layer; an encapsulation layer formed on the display unit; and an organic film coated on an edge portion of the barrier layer.

[0498] Examples

[0499] The following presents synthesis examples and examples to further specifically illustrate the features of the present invention. Materials, processing contents, processing steps, etc. shown below can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. In addition, for the evaluation of luminous characteristics, a source meter (manufactured by Keithley: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies Japan, Ltd.: E5273A), an optical power meter measuring device (manufactured by Newport Corporation: 1930C), a spectrometer (manufactured by Ocean Optics: USB2000), a spectroradiometer (manufactured by TOPCON CORPORATION: SR-3), and a streak camera (type C4334 manufactured by Hamamatsu Photonics K.K.) are used. And, for the measurement of the energies of HOMO and LUMO, it is carried out by an atmospheric photoelectron spectrometer (manufactured by RIKEN KEIKI CO., LTD.: AC-3, etc.).

[0500] In the following synthesis examples, the compounds included in the general formula (1) were synthesized.

[0501] (Synthesis Example)

[0502] [Chemical Formula 54]

[0503]

[0504] Intermediate a

[0505] Under a nitrogen stream, degassed 1,4-dioxane (50 mL) was added to a mixture of 6-bromo-12H-[1]benzothieno[2,3-a]carbazole (2.00 g, 5.68 mmol), bis(pinacolato)diboron (2.16 g, 8.52 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.083 g, 0.11 mmol), and potassium acetate (1.39 g, 14.2 mmol), and the mixture was stirred at 110 °C for 15 h. After stirring, it was cooled to room temperature, and 2-chloro-4,6-bis(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (1.89 g, 6.81 mmol), tetrakis(triphenylphosphine)palladium(0) (0.33 g, 0.28 mmol), potassium carbonate (1.96 g, 14.2 mmol), and degassed tetrahydrofuran (50 mL) / water (25 mL) were added to the reaction solution, and the mixture was stirred at 75 °C for 24 h. After completion of the reaction, it was cooled to room temperature, water was added, and filtration and extraction were carried out. The obtained mixture was purified by silica gel column chromatography to obtain intermediate a (0.356 g, 0.692 mmol, yield 12.2%).

[0506] 1 H NMR (400 MHz, CDCl3) δ 8.76 (s, 1H), 8.48 (s, 1H), 8.22 (d, J = 7.6 Hz, 1H), 8.13 (d, J = 7.8 Hz, 1H), 7.97 (d, J = 7.3 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 7.54 - 7.49 (m, 1H), 7.46 - 7.41 (m, 1H), 7.37 - 7.33 (m, 1H), 7.24 - 7.20 (m, 1H)

[0507] ASAP mass spectrometry: theoretical value 514.20, observed value 515.47.

[0508] [Chemical formula 55]

[0509]

[0510] Intermediate b

[0511] Under a nitrogen stream, dichloromethane (200 mL) was added to a mixture of 12H-[1]benzothieno[2,3-a]carbazole (7.50 g, 27.4 mmol) and N-bromosuccinimide (10.2 g, 57.6 mmol), and the mixture was stirred at room temperature for 1 h. After stirring, water was added for extraction, and it was dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure and reprecipitated to obtain intermediate b (10.8 g, 25.0 mmol, crude yield 91.1%).

[0512] ASAP mass spectrometry: theoretical value 431.15, observed value 431.96

[0513] Intermediate c

[0514] Under a nitrogen stream, a degassed mixed solution of tetrahydrofuran (250 mL) and water (125 mL) was added to a mixture of intermediate b (9.40 g, 21.8 mmol), phenyl-d5-boronic acid (2.24 g, 17.6 mmol), tetrakis(triphenylphosphine)palladium(0) (1.13 g, 0.980 mmol), and potassium carbonate (8.13 g, 58.8 mmol). The temperature was raised to 75 °C and the mixture was reacted for 15 hours. After the reaction was completed, it was cooled to room temperature and extraction was carried out. The obtained mixture was purified by silica gel column chromatography to obtain intermediate c (1.30 g, 3.00 mmol, yield 13.8%).

[0515] 1 H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.24 - 8.17 (m, 1H), 7.91 - 7.88 (m, 2H), 7.55 (dd, J = 8.6, 2.0 Hz, 1H), 7.44 (d, J = 8.7 Hz, 1H), 7.38 (t, J = 7.5 Hz, 1H), 7.21 - 7.09 (m, 2H)

[0516] ASAP mass spectrometry: theoretical value 433.38, observed value 435.14

[0517] Intermediate d

[0518] Under a nitrogen stream, degassed 1,4-dioxane (30 mL) was added to a mixture of intermediate c (1.30 g, 3.00 mmol), bis(pinacolato)diboron (1.52 g, 6.00 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.219 g, 0.300 mmol), and potassium acetate (1.47 g, 15.0 mmol), and the mixture was stirred at 110 °C for 15 hours. After stirring, it was cooled to room temperature, and 2-chloro-4,6-bis(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (1.08 g, 3.90 mmol), dichloro-bis(triphenylphosphine)palladium(II) (0.211 g, 0.300 mmol), potassium carbonate (1.59 g, 15.0 mmol), degassed tetrahydrofuran (30 mL), and water (15 mL) were added to the reaction solution, and the mixture was stirred at 75 °C for 24 hours. After the reaction was completed, it was cooled to room temperature and water was added, followed by filtration and extraction. The obtained mixture was purified by silica gel column chromatography to obtain intermediate d (0.444 g, 0.745 mmol, yield 24.6%).

[0519] 1 H NMR (400 MHz, CDCl3) δ 9.58 (s, 1H), 8.46 (dd, J = 8.7, 1.4 Hz, 1H), 8.56 (s, 1H), 8.18 (s, 1H), 7.93 (d, J = 7.8 Hz, 1H), 7.73 (d, J = 8.7 Hz, 1H), 7.38 (t, J = 6.4 Hz, 1H), 7.25 - 7.11 (m, 2H)

[0520] ASAP mass spectrometry: Theoretical value 595.80, Observed value 596.38.

[0521] [Chemical formula 56]

[0522]

[0523] Intermediate e

[0524] Under a nitrogen stream, degassed 1,4-dioxane (240 mL) was added to a mixture of 2-chloro-4-iodoaniline (30.0 g, 118 mmol), bis(pinacolato)diboron (45.1 g, 178 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (8.66 g, 11.8 mmol), and potassium acetate (58.1 g, 592 mmol), and the mixture was stirred at 110 °C for 15 h. After completion of the reaction, the mixture was cooled to room temperature, water was added, and filtration and extraction were performed. The obtained mixture was purified by silica gel column chromatography to obtain intermediate e (17.5 g, 69.1 mmol, yield 58.4%).

[0525] 1 H NMR (400 MHz, CDCl3) δ 7.69 (d, J = 1.4 Hz, 1H), 7.49 (dd, J = 8.2, 1.4 Hz, 1H), 6.73 (d, J = 8.2 Hz, 1H), 4.24 (s, 2H), 1.32 (s, 12H)

[0526] ASAP mass spectrometry: calculated value 253.10, observed value 254.09.

[0527] Intermediate f

[0528] Under a nitrogen stream, degassed toluene (60 mL) and water (30 mL) were added to a mixture of intermediate e (6.00 g, 23.7 mmol), 2-chloro-4,6-bis(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (6.57 g, 23.7 mmol), dichloro-bis(triphenylphosphine)palladium(II) (1.66 g, 2.37 mmol), and sodium carbonate (12.5 g, 118 mmol), and the mixture was stirred at 110 °C for 15 h. After completion of the reaction, the mixture was cooled to room temperature, water was added, and filtration and extraction were performed. The obtained mixture was purified by silica gel column chromatography to obtain intermediate f (1.87 g, 5.07 mmol, yield 21.4%).

[0529] 1 H NMR (400 MHz, CDCl3) δ 8.71 (d, J = 1.8 Hz, 1H), 8.53 (dd, J = 8.7, 1.8 Hz, 1H), 6.90 (d, J = 8.7 Hz, 1H), 4.52 (s, 2H)

[0530] ASAP mass spectrometry: calculated value 368.16, observed value 369.24.

[0531] Intermediate g

[0532] Under a nitrogen stream, degassed toluene (150 mL) was added to a mixture of intermediate f (1.66 g, 4.50 mmol), 4-iododibenzothiophene (1.67 g, 5.40 mmol), palladium(II) acetate (0.101 g, 0.450 mmol), bis[2-(diphenylphosphino)phenyl] ether (0.364 g, 0.675 mmol), and sodium tert-butoxide (0.865 g, 9.00 mmol), and the mixture was stirred at 80 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and water was added, followed by filtration and extraction. The obtained mixture was purified by silica gel column chromatography to give intermediate g (0.648 g, 1.18 mmol, yield 26.1%).

[0533] 1 H NMR (400 MHz, CDCl3) δ 8.85 (d, J = 2.1 Hz, 1H), 8.54 (dd, J = 8.7, 1.6 Hz, 1H), 8.22 - 8.20 (m, 1H), 8.07 (dd, J = 7.1, 1.6 Hz, 1H), 7.88 - 7.86 (m, 1H), 7.57 - 7.49 (m, 4H), 7.10 (d, J = 8.7 Hz, 1H), 6.64 (s, 1H)

[0534] ASAP mass spectrometry: theoretical value 550.18, observed value 551.34.

[0535] Intermediate h

[0536] Under a nitrogen stream, degassed dimethylacetamide (30 mL) was added to a mixture of intermediate g (0.640 g, 4.50 mmol), palladium(II) acetate (0.0521 g, 0.232 mmol), tricyclohexylphosphine (0.130 g, 0.465 mmol), and cesium carbonate (1.14 g, 3.48 mmol), and the mixture was stirred at 150 °C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and water was added, followed by filtration and extraction. The obtained mixture was purified by silica gel column chromatography to give intermediate h (0.280 g, 0.544 mmol, yield 46.9%).

[0537] 1 H NMR (400 MHz, CDCl3) δ 9.60 (s, 1H), 8.95 (dd, J = 8.6, 1.7 Hz, 1H), 8.51 (s, 1H), 8.38 (d, J = 8.2 Hz, 1H), 8.29 (d, J = 7.3 Hz, 1H), 8.14 (d, J = 8.2 Hz, 1H), 7.96 - 7.93 (m, 1H), 7.69 (d, J = 8.5 Hz, 1H), 7.55 - 7.47 (m, 2H)

[0538] ASAP mass spectrometry: theoretical value 514.20, observed value 515.52.

[0539] [Chemical formula 57]

[0540]

[0541] Intermediate i

[0542] Under a nitrogen stream, a solution of 2-amino-3,5,6-trifluoro-1,4-benzenedicarbonitrile (6.00 g, 30.4 mmol) and 42 wt% aqueous tetrafluoroboric acid (6.36 g, 304 mmol) in acetonitrile (250 mL) was stirred at 0 °C for 15 minutes. Then, bromotrichloromethane (12.1 g, 60.9 mmol) and sodium nitrite (5.25 g, 76.1 mmol) dissolved in water (63 mL) were added, and the mixture was stirred at room temperature for 15 hours. The mixture was returned to room temperature, an aqueous sodium bisulfite solution was added, and the mixture was extracted with dichloromethane and dried over anhydrous magnesium sulfate. It was concentrated under reduced pressure, and the obtained mixture was purified by silica gel column chromatography to obtain intermediate i (3.10 g, 11.9 mmol, yield 38.4%).

[0543] ASAP mass spectrometry: theoretical value 259.92, observed value 260.94.

[0544] Intermediate j

[0545] Under a nitrogen stream, intermediate i (0.20 g, 0.77 mmol) was added to a solution of carbazole-1,2,3,4,5,6,7,8-d8 (0.40 g, 2.3 mmol) and potassium carbonate (0.53 g, 3.8 mmol) in dimethylformamide (20 mL), and the mixture was stirred at room temperature for 2 hours. The mixture was returned to room temperature, quenched with water, the precipitated solid was filtered, and washed with methanol. The obtained solid was purified by silica gel column chromatography to obtain intermediate j (0.43 mg, 0.59 mmol, yield 77%).

[0546] ASAP mass spectrometry: theoretical value 725.27, observed value 726.73

[0547] Compound 16

[0548] Under a nitrogen stream, intermediate j (0.29 g, 0.40 mmol) was added to a solution of intermediate a (0.27 g, 0.52 mmol) and cesium carbonate (0.16 g, 0.48 mmol) in dimethylformamide (5 mL), and the mixture was stirred at 110 °C for 2 hours. The mixture was returned to room temperature, quenched with water, the precipitated solid was filtered, and washed with methanol. The obtained solid was purified by silica gel column chromatography to give compound 16 (0.42 g, 0.36 mmol, 90% yield).

[0549] 1 H NMR (400 MHz, CDCl3) δ 8.46 (s, 1H), 8.08 (t, J = 7.7 Hz, 2H), 7.82 (d, J = 7.6 Hz, 1H), 7.58 - 7.54 (m, 1H), 7.29 (t, J = 7.1 Hz, 1H), 7.11 - 7.07 (m, 1H), 6.97 - 6.93 (m, 2H)

[0550] ASAP mass spectrometry: theoretical value 1159.55, observed value 1160.13

[0551] Compound 2608

[0552] Under a nitrogen stream, intermediate j (0.417 g, 0.570 mmol) was added to a solution of intermediate d (0.417 g, 0.750 mmol) and cesium carbonate (0.224 g, 0.689 mmol) in dimethylformamide (20 mL), and the mixture was stirred at 110 °C for 2 hours. The mixture was returned to room temperature, quenched with water, the precipitated solid was filtered, and washed with methanol. The obtained solid was purified by silica gel column chromatography to give compound 2608 (0.560 g, 0.451 mmol, 78.6% yield).

[0553] 1 H NMR (400 MHz, CDCl3) δ 9.15 (s, 1H), 8.46 (d, J = 10.3 Hz, 1H), 8.01 (d, J = 6.2 Hz, 1H), 7.89 (s, 1H), 7.50 (t, J = 4.8 Hz, 1H), 7.27 - 7.12 (m, 3H)

[0554] ASAP mass spectrometry: theoretical value 1241.65, observed value 1242.08

[0555] Compound 880

[0556] Under a nitrogen stream, intermediate j (0.456 g, 0.627 mmol) was added to a degassed dimethylformamide solution (20 mL) of intermediate h (0.420 g, 0.816 mmol) and cesium carbonate (0.245 g, 0.753 mmol), and the mixture was stirred at 110 °C for 2 hours. The mixture was returned to room temperature, quenched with water, the precipitated solid was filtered, and washed with methanol. The obtained solid was purified by silica gel column chromatography to obtain compound 880 (0.497 g, 0.428 mmol, yield 68.3%).

[0557] 1 H NMR (400 MHz, CDCl3) δ 9.20 (d, J = 0.9 Hz, 1H), 8.34 (dd, J = 8.7, 1.6 Hz, 2H), 8.18 (s, 2H), 8.08 - 8.06 (m, 1H), 7.65 - 7.63 (m, 2H), 7.06 (d, J = 9.2 Hz, 1H)

[0558] ASAP mass spectrometry: Theoretical value 1159.55, Observed value 1160.79

[0559] (Example 1) Fabrication and Evaluation of Organic Electroluminescent Device

[0560] By vacuum evaporation, on a glass substrate formed with an anode composed of indium tin oxide (ITO) with a film thickness of 50 nm, each thin film was laminated at a vacuum degree of 5.0×10 -5 Pa. First, HAT-CN with a thickness of 10 nm was formed on the ITO, NPD with a thickness of 30 nm was formed thereon, TrisPCz with a thickness of 10 nm was further formed thereon, and EBL1 with a thickness of 5 nm was formed thereon. Then, H1 and compound 16 were co-evaporated from different evaporation sources to form a layer with a thickness of 40 nm, which was set as the light-emitting layer. The concentration of compound 16 in the light-emitting layer was set to 35 wt%. Then, after forming SF3-TRZ with a thickness of 10 nm, Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a layer with a thickness of 30 nm. The concentrations of Liq and SF3-TRZ in this layer were 30 wt% and 70 wt%, respectively. Further, Liq was formed with a thickness of 2 nm, and then aluminum (Al) was evaporated with a thickness of 100 nm to form a cathode, which was set as the organic electroluminescent device of Example 1.

[0561] Comparative compound 1 was used to replace compound 16, and the organic electroluminescent device of Comparative Example 1 was fabricated through the same steps.

[0562] The 15.4 mA / cm of each organic electroluminescent device was measured 2The external quantum yield (EQE) under [conditions], as a result, it was 7.48% for Example 1 and 4.35% for Comparative Example 1. Thus, it was confirmed that by using the compound represented by General Formula (1), an efficient organic light-emitting device can be provided.

[0563] (Example 2) Fabrication and Evaluation of an Organic Electroluminescent Device Used as a Co-Dopant

[0564] An organic light-emitting device of Example 2 was fabricated by the same procedure as in Example 1, except that the light-emitting layer having a thickness of 40 nm was formed by sequentially vapor-depositing H1, Compound 16, and E1 as a dopant from different vapor-deposition sources at 64.5 wt%, 35.0 wt%, and 0.5 wt%, respectively, only changing this point instead of the light-emitting layer in Example 1.

[0565] An organic light-emitting device of Comparative Example 2 was fabricated by the same procedure using Comparative Compound 1 instead of Compound 16.

[0566] The external quantum yield (EQE) at 15.4 mA / cm 2 was measured for each organic light-emitting device. As a result, it was 16.31% for Example 2 and 14.78% for Comparative Example 2. Thus, it was confirmed that by using the compound represented by General Formula (1) as a co-dopant, a high-efficiency organic light-emitting device can be provided.

[0567] (Example 3) Fabrication and Evaluation of an Organic Electroluminescent Device Using Two Host Materials

[0568] An organic light-emitting device of Example 3 was fabricated by the same procedure as in Example 1, except that the light-emitting layer having a thickness of 40 nm was formed by sequentially vapor-depositing H1, H2, Compound 16, and E1 from different vapor-deposition sources at 44.5 wt%, 20.0 wt%, 35.0 wt%, and 0.5 wt%, respectively, only changing this point instead of the light-emitting layer in Example 1.

[0569] The external quantum yield (EQE) at 15.4 mA / cm 2 was measured, and as a result, it was 14.93%. It was confirmed that good light-emitting characteristics were exhibited even when two host materials were used.

[0570] [Chemical Formula 58]

[0571]

[0572] Industrial Applicability

[0573] By using the compound represented by General Formula (1), an organic light-emitting device having good light-emitting characteristics can be provided. Therefore, the industrial applicability of the present invention is high.

Claims

1. A compound represented by the following general formula (1): [Chemical formula 1] In general formula (1), X represents an oxygen atom, a sulfur atom or [Chemical formula 2] * indicates the bonding position, R 1 ~R 3 and Z each independently represent a deuterium atom or a substituent, R 4 ~R 8 each independently represent a hydrogen atom, a deuterium atom or a substituent, R 1 ~R 8 at least one of which is a substituted or unsubstituted aryl group or acceptor group, wherein, When R 2 is not a receptor group, at least one of R 1 and R 3 ~R 8 is a substituted or unsubstituted 2,4,6-triazinyl group, n1 and n3 each independently represent any integer from 0 to 4, n2 represents any integer from 0 to 2, p represents any integer from 0 to 3, q represents any integer from 1 to 4. When n1 is an integer of 2 or more, two or more R 1 may be the same or different. When n2 is 2, the two R 2 may be the same or different. When n3 is an integer of 2 or more, two or more R 3 may be the same or different. When p is an integer of 2 or more, two or more Z may be the same or different. When q is an integer of 2 or more, two or more of the structures within the parentheses may be the same or different.

2. The compound according to claim 1, wherein R 1 ~R 3 At least one of them is a receptor group.

3. The compound according to claim 2, wherein R 2 is a receptor group.

4. The compound according to claim 1, wherein the acceptor group is represented by the following general formula (b): [Chemical formula 3] In general formula (b), X 1 ~X 3 each independently represents N or C(R), where at least one of X 1 ~X 3 is N, R represents a hydrogen atom, a deuterium atom or a substituent, and Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

5. The compound according to claim 4, wherein X 1 ~X 3 is N.

6. The compound according to claim 1, wherein Z is a substituted or unsubstituted diarylamino group, wherein the two aryl groups may be bonded to each other, or Z is a substituted or unsubstituted aryl group.

7. The compound according to claim 6, wherein Z is a substituted or unsubstituted carbazol-9-yl group.

8. The compound according to claim 1, wherein X is an oxygen atom or a sulfur atom.

9. The compound according to claim 1, wherein q is 1.

10. The compound according to claim 1, wherein n1 + n2 + n3 is 1 or more.

11. The compound according to claim 1, which has at least one deuterium atom.

12. A luminescent material composed of the compound according to any one of claims 1 to 11.

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

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

15. An organic semiconductor element containing the compound according to any one of claims 1 to 11.

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

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

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

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

20. The organic light-emitting element according to claim 17, wherein the amount of light emission from the compound in the materials contained in the element is the largest.

21. The organic light-emitting element according to claim 19, wherein the amount of light emission from the luminescent material is more than the amount of light emission from the compound.

22. The organic light-emitting element according to claim 16, which is an organic electroluminescent element.

23. The organic light-emitting element according to claim 16, which emits delayed fluorescence.

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