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

Abstract

Compounds represented by the following general formulas are useful for organic light-emitting diodes. X1 to X4 represent N or CR, and R and R1 to R7 represent hydrogen atoms, deuterium atoms, alkyl groups, aryl groups, etc. Ar represents an arylene group or a heteroarylene group, and A represents a cyclic structure.

Description

Technology Field

[0001] The present invention relates to a compound having good characteristics. The present invention also relates to a light-emitting material and an organic light-emitting device using said compound. Background Technology

[0002] Organic light-emitting devices are light-emitting devices utilizing organic materials and have recently been attracting attention. Among them, organic electroluminescent devices (organic EL devices) are expected to serve as next-generation light sources. For this reason, research on the development of materials useful for organic light-emitting devices, including organic electroluminescent devices, is actively underway. For example, a compound having a structure in which a donor group containing a phenazine backbone is combined with an acceptor group, the 5H-indolo[3,2,1-de]phenazine-5-yl group, has been proposed (see Patent Document 1). Prior art literature

[0003] Patent Document 1: WO2022 / 168956A1 The problem to be solved

[0004] Meanwhile, there is still room for improvement regarding the characteristics of organic light-emitting diodes, and further improvement in characteristics is desired.

[0005] Accordingly, the inventors conducted a thorough examination with the aim of developing a novel compound that contributes to the improvement of the characteristics of an organic light-emitting device. means of solving the problem

[0006] As a result of conducting a review, the inventors have discovered that a compound in which a group having a characteristic structure for a specific framework is combined is a compound useful for organic light-emitting diodes. The present invention is proposed based on such knowledge and has the following composition.

[0007] [1] A compound represented by the following general formula (1).

[0008] General formula (1)

[0009] [Chemical Formula 1]

[0010]

[0011] [In general formula (1), X 1 is N or CR 11 Represents, and X 2 is N or CR 12 Represents, X 3 is N or CR 13 Represents, and X 4 is N or CR 14 It represents. R 1 ~R 7 and R 11 ~R 14 represents, respectively, a hydrogen atom, a deuterium atom, or a substituent. R 8 It represents silver, a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar and R 1 , R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 Ar and Ar and A never combine to form a cyclic structure. Ar represents a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. A represents a cyclic structure.

[0012] [2] Compounds described in [1] in which Ar is a substituted or unsubstituted arylene group.​

[0013] [3] Compounds described in [2] in which Ar is a substituted or unsubstituted phenylene group.

[0014] [4] R 8 A compound described in any one of [1] to [3], which is a substituted or unsubstituted aryl group.

[0015] [5] A compound described in any one of [1] to [4] having a benzothieno structure, benzofuro structure, indolo structure, benzo structure, naphtho structure or phenantro structure.

[0016] [6] A compound described in any one of [1] to [5], which is a cyclic structure in which A may be substituted with one or more atoms selected from the group consisting of deuterium atoms and general formula (2').

[0017] General formula (2')

[0018] [Chemical Formula 2]

[0019]

[0020] [In general formula (2'), X 1 ' is N or CR 11 Represents ', X 2 ' is N or CR 12 Representing ', X 3 ' is N or CR 13 Represents ', X 4 ' is N or CR 14 Represents '. R 1 '~R 7 Each represents a hydrogen atom, a deuterium atom, or a cyano group independently. * indicates a bonding position.]

[0021] [7] X 1 This CR 11 and X 2 Ga CR 12 is, X 3 This CR 13 and X 4 Ga CR 14A compound described in any one of [1] to [6].

[0022] [8] R 11 ~R 14 A compound described in [7], in which at least one of the groups may be a cyano group or an aryl group that may be substituted with a deuterium atom.

[0023] [9] R 11 ~R 14 Compounds described in [7], each having either a hydrogen atom or a deuterium atom independently.

[0024]

[10] Ar is a substituted or unsubstituted arylene group, and R 8 A compound described in any one of [1] to [9], wherein the aryl group is substituted or unsubstituted and A has a benzothieno structure.

[0025]

[11] X 1 This CR 11 and X 2 Ga CR 12 is, X 3 This CR 13 and X 4 Ga CR 14 Phosphorus,

[10] compound.

[0026]

[12] A luminescent material comprising a compound described in any one of [1] to

[11] .

[0027]

[13] A delayed fluorescent material comprising a compound described in any one of [1] to

[11] .

[0028]

[14] An organic electroluminescent device comprising a compound described in any one of [1] to

[11] .

[0029]

[15] An organic electroluminescent device described in

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

[0030]

[16] An organic electroluminescent device described in

[14] or

[15] , wherein the organic electroluminescent device has a layer containing the compound, and the layer also includes a light-emitting material having a structure outside the range of the general formula (1).

[0031]

[17] An organic electroluminescent device described in

[16] , in which the amount of light emitted from the above-mentioned light-emitting material is greater than the amount of light emitted from the above-mentioned compound. Effects of the invention

[0032] The compound of the present invention is a compound useful for organic light-emitting devices. By using the compound of the present invention, an organic light-emitting device with excellent characteristics can be manufactured. Specific details for implementing the invention

[0033] The content of the present invention is described in detail below. The description of the constituent elements described below may be based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. Furthermore, numerical ranges indicated by "~" in this specification refer to a range that includes the values ​​described before and after "~" as lower and upper limits. Also, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention are deuterium atoms ( 2 It can be substituted with H (deuterium D). In the chemical structural formulas of this specification, hydrogen atoms are represented as H or their representation is omitted. For example, when the representation of 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 location where the representation is omitted. In this specification, the term "substituent" refers to an atom or group of atoms other than hydrogen atoms and deuterium atoms. Meanwhile, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0034] [Compounds represented by general formula (1)]

[0035] The following general formula (1) describes a compound represented by the following general formula.

[0036] General formula (1)

[0037] [Chemical Formula 3]

[0038]

[0039] In general formula (1), X 1 is N or CR 11 Represents, and X 2 is N or CR 12 Represents, X 3 is N or CR 13 Represents, and X 4 is N or CR 14 It represents.

[0040] In some embodiments of the present invention, X 1 ~X 4 Not all are N. In some embodiments of the present invention, X 1 ~X 4 At least one of (preferably 1 to 3, more preferably 2, for example 1, for example 2) is N. In some embodiments of the present invention, X 1 Only N. In some embodiments of the present invention, X 2 Only N. In some embodiments of the present invention, X 3 Only N. In some embodiments of the present invention, X 4 Only N. In some embodiments of the present invention, X 1 and X 2 Only N. In some embodiments of the present invention, X 1 and X 3 Only N. In some embodiments of the present invention, X 1 and X 4 Only N. In some embodiments of the present invention, X 2 and X​3 Only N. In some embodiments of the present invention, X 2 and X 4 Only N. In some embodiments of the present invention, X 3 and X 4 Only N.

[0041] In general formula (1), R 11 ~R 14 Each represents independently a hydrogen atom, a deuterium atom, or a substituent. The deuterium atom and substituent referred to herein may, for example, be selected from Group A described below, from Group B described below, from Group C described below, from Group D described below, from Group E described below, or from any multiple of Groups A through E. In some embodiments of the present invention, R 11 ~R 14 Each is independently a hydrogen atom, a deuterium atom, a group comprising a cyano group, or a substituted or unsubstituted aryl group. In some aspects of the present invention, R 11 ~R 14 is an aryl group that may be independently substituted with a hydrogen atom, a deuterium atom, a cyano group, or a deuterium atom. In some embodiments of the present invention, R 11 ~R 14 is, each independently, a hydrogen atom, a deuterium atom, or a cyano group. In some aspects of the present invention, R 11 ~R 14 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group (e.g., an aryl group that may be substituted with a deuterium atom). In some embodiments of the present invention, R 11 ~R 14Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted heteroaryl group bonded to a carbon atom, e.g., a substituted or unsubstituted heteroaryl group bonded to a nitrogen atom). In some aspects of the present invention, R 11 ~R 14 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group (e.g., an alkyl group that may be substituted with a deuterium atom). In some embodiments of the present invention, R 11 ~R 14 At least one of them is a cyano group, or an aryl group that may be substituted with a deuterium atom (e.g., a phenyl group that may be substituted with a deuterium atom). In some embodiments of the present invention, R 11 ~R 14 It comprises at least one (e.g., one, e.g., two) cyano groups as a whole. In some aspects of the present invention, R 11 This includes cyano, for example R 11 This is a cyano group. In some aspects of the present invention, R 12 ga includes cyano, for example R 12 ga is a cyano. In some aspects of the present invention, R 13 This includes cyano, for example R 13 This is a cyano group. In some aspects of the present invention, R 14 ga includes cyano, for example R 14α is a cyano group. The phrase "including a cyano group" as used herein includes not only the case where it is a cyano group itself, but also groups in which the cyano group is bonded through other atomic groups, such as an aryl group that is substituted at least with a cyano group and may also be substituted with something other than a cyano group, a heteroaryl group that is substituted at least with a cyano group and may also be substituted with something other than a cyano group, or an alkyl group that is substituted at least with a cyano group and may also be substituted with something other than a cyano group. In some embodiments of the present invention, R 11 ~R 14 Each is independently a hydrogen atom or a deuterium atom.

[0042] R 11 and R 12 , R 12 and R 13 , R 13 and R 14 There are no cases where they all combine with each other to form a ring structure.

[0043] In general formula (1), R 1 ~R 7 Each represents independently a hydrogen atom, a deuterium atom, or a substituent. The deuterium atom and substituent referred to herein may, for example, be selected from Group A described below, from Group B described below, from Group C described below, from Group D described below, from Group E described below, or from any multiple of Groups A through E. In some embodiments of the present invention, R 1 ~R 7 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In some aspects of the present invention, R 1 ~R 7Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted heteroaryl group bonded to a carbon atom, e.g., a substituted or unsubstituted heteroaryl group bonded to a nitrogen atom). In some aspects of the present invention, R 1 ~R 7 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group. In some embodiments of the present invention, R 1 ~R 7 The whole comprises at least one (e.g., one, e.g., two) cyano groups. In some aspects of the present invention, R 2 ga includes cyano, for example R 2 ga is a cyano. In some aspects of the present invention, R 3 This includes cyano, for example R 3 This is a cyano group. In some aspects of the present invention, R 5 ga includes cyano, for example R 5 ga is a cyano. In some aspects of the present invention, R 6 This includes cyano, for example R 6 This is a cyano group. In some aspects of the present invention, R 1 ~R 7 Each is independently a hydrogen atom or a deuterium atom.

[0044] Ar and R 1 , R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 11 , R 14 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7There are no cases where both and Ar combine to form a ring structure.

[0045] R 1 ~R 7 , R 11 ~R 14 The aryl group that can be employed may be a single ring or a condensed ring formed by the condensation of two or more rings. In the case of a condensed ring, the number of condensed rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the rings include a benzene ring, a naphthalene ring, anthracene ring, a phenanthrene ring, and a pyrene ring. Specific examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group. The number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected within the range of 6 to 14 or within the range of 6 to 10.

[0046] R 1 ~R 7 , R 11 ~R 14 The heteroaryl group that can be employed contributes to bonding to carbon atoms constituting the aromatic heterocyclic ring and contributes to bonding to nitrogen atoms. Pyridine rings, pyrimidine rings, and triazine rings can be exemplified as aromatic heterocyclic rings containing bonded carbon atoms. Pyrrole rings can be exemplified as aromatic heterocyclic rings containing bonded nitrogen atoms. These aromatic heterocyclic rings may be substituted, and other rings may be condensed thereto. Other rings may include aromatic hydrocarbon rings or aromatic heterocyclic rings, and rings formed by further condensation of these rings may be condensed thereto to the above-mentioned aromatic heterocyclic rings.

[0047] R 1 ~R 7 , R 11 ~R 14The alkyl group that can be employed may be a straight-chain, branched, or cyclic type. In addition, two or more types of straight-chain, cyclic, and branched portions may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. In addition, the number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decaneyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group.

[0048] R 1 ~R 7 , R 11 ~R 14 The aryl group, heteroaryl group, and alkyl group that can be employed may be substituted with a deuterium atom or a substituent. The deuterium atom and substituent mentioned herein may, for example, be selected from Group A described below, from Group B described below, from Group C described below, from Group D described below, from Group E described below, or from each of the multiple groups A to E.

[0049] R 1 ~R 7 , R 11 ~R 14 The aryl group, heteroaryl group, or alkyl group that can be employed may be substituted with at least one cyano group (e.g., 1 to 3 cyano groups, e.g., 1 cyano group, e.g., 2 cyano groups). In some embodiments of the present invention, R 1 ~R 7 , R 11 ~R 14At least one of them (preferably 1 to 3, for example 1, for example 2, for example 3) is an aryl group substituted with at least a cyano group, a heteroaryl group substituted with at least a cyano group, an alkyl group substituted with at least a cyano group, or a cyano group.

[0050] In the following, specific examples of the structure represented by the following general formula (2), which is a substructure of general formula (1), are shown. In general formula (2), * indicates a connection position. However, the structure represented by general formula (2) that can be adopted in the present invention is not limited to the following specific examples. Also, in the following specific examples, dashed lines indicate connection positions.

[0051] General formula (2)

[0052] [Chemical Formula 4]

[0053]

[0054] [Chemical Formula 5]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] Groups in which all hydrogen atoms present in D1 to D97 are substituted with deuterium atoms are exemplified here as D98 to D194 in order. In some embodiments of the present invention, the group represented by general formula (2) is selected from D1 to D194. In some embodiments of the present invention, the group represented by general formula (2) is selected from D1 to D12, D61 to D78, D97 to D109, D158 to D175, and D194. In some embodiments of the present invention, the group represented by general formula (2) is selected from D13 to D60, D79 to D96, D110 to D157, and D176 to D193. In some embodiments of the present invention, the group represented by general formula (2) is selected from the groups having a cyano group among D1 to D194. In some embodiments of the present invention, the group represented by general formula (2) is selected from among the groups D1 to D194 that do not have a cyano group.

[0061] In general formula (1), Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.

[0062] The arylene group that Ar can take may be a single ring or a condensed ring formed by the condensation of two or more rings. In the case of a condensed ring, it is preferable that the number of condensed rings be 2 to 6, and for example, can be selected from 2 to 4. Specific examples of rings include benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and pyrene rings. Specific examples of arylene groups include 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 2,3-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, 1,8-naphthylene, 2,6-naphthylene, and 2,7-naphthylene groups. The number of atoms constituting the ring backbone of the arylene group is preferably 6 to 40, more preferably 6 to 20, and may be selected within the range of 6 to 14 or within the range of 6 to 10.

[0063] The heteroarylene group that Ar can take is a contributing factor to bonding with carbon atoms constituting an aromatic heterocyclic ring and a contributing factor to bonding with nitrogen atoms. That is, for the 5-ring condensation group described above Ar in general formula (1), Ar is a contributing factor to bonding with carbon atoms constituting an aromatic heterocyclic ring and a contributing factor to bonding with nitrogen atoms. Also, for the condensation group containing A described below Ar in general formula (1), Ar is a contributing factor to bonding with carbon atoms constituting an aromatic heterocyclic ring and a contributing factor to bonding with nitrogen atoms. Also, for both the 5-ring condensation group described above Ar in general formula (1) and the condensation group containing A described below Ar, Ar is a contributing factor to bonding with carbon atoms constituting an aromatic heterocyclic ring and a contributing factor to bonding with nitrogen atoms. In addition, Ar contributes to bonding to the carbon atoms constituting the aromatic heterocyclic ring with respect to the condensation group of five rings described above Ar in general formula (1), and also contributes to bonding to the nitrogen atoms constituting the aromatic heterocyclic ring with respect to the condensation group containing A described below Ar in general formula (1). In addition, Ar contributes to bonding to the nitrogen atoms constituting the aromatic heterocyclic ring with respect to the condensation group of five rings described above Ar in general formula (1), and also contributes to bonding to the carbon atoms constituting the aromatic heterocyclic ring with respect to the condensation group containing A described below Ar in general formula (1). Pyridine rings, pyrimidine rings, and triazine rings can be exemplified as aromatic heterocyclic rings containing the bonding carbon atoms. Pyrrole rings can be exemplified as aromatic heterocyclic rings containing the bonding nitrogen atoms. These aromatic heterocyclic rings may be substituted, and other rings may be condensed. Other rings may include aromatic hydrocarbon rings or aromatic complex rings, and rings formed by further condensation of these rings may be condensed into the above-mentioned aromatic complex ring.

[0064] In some embodiments of the present invention, Ar is a substituted or unsubstituted arylene group, preferably a substituted or unsubstituted phenylene group, for example, a substituted or unsubstituted 1,3-phenylene group, for example, a substituted or unsubstituted 1,4-phenylene group. In some embodiments of the present invention, Ar is a substituted or unsubstituted heteroarylene group bonded to a carbon atom. In some embodiments of the present invention, Ar is a substituted or unsubstituted heteroarylene group bonded to a nitrogen atom.

[0065] In general formula (1), R 8 represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. For the description and preferred range of the alkyl group, aryl group, and heteroaryl group referred to herein, see the above R 1 ~R 7 , R 11 ~R 14 Refer to the description and preferred range of alkyl groups, aryl groups, and heteroaryl groups that can be employed. In some embodiments of the present invention, R 8 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In some aspects of the present invention, R 8 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted heteroaryl group bonded to a carbon atom, e.g., a substituted or unsubstituted heteroaryl group bonded to a nitrogen atom). In some aspects of the present invention, R 8 The substituted or unsubstituted heteroaryl group that can be employed is not the heteroaryl group represented by the general formula (2') described below. In some embodiments of the present invention, R 8 is a group that includes a cyano group. For example, R 8 is a cyano. For example, R 8 It is an aryl that can be replaced at least with a cyano-gi, and can also be replaced with something other than a cyano-gi.

[0066] In some preferred embodiments of the present invention, R 8 is a substituted or unsubstituted aryl group. Regarding the explanation of the aryl group mentioned here, the above R 1 ~R 7 , R 11 ~R 14 You may refer to the description of the aryl group that can be employed. In some embodiments of the present invention, R 8 It is an aryl group that may be substituted with a deuterium atom (e.g., a perdeuterated phenyl group, e.g., an unsubstituted phenyl group). In some embodiments of the present invention, R 8 It is a phenyl group that can be substituted with a cyano group, and may also be substituted with something other than a cyano group.

[0067] R below 8 Specific examples of are given. However, R that can be employed in the present invention 8 The following specific examples are not to be interpreted restrictively. In the following specific examples, the methyl group is omitted. For this reason, for example, Z7 represents a p-tholyl group, Z23 represents a methyl group, Z24 represents an isopropyl group, and Z25 represents a tert-butyl group. * indicates the bonding position.

[0068] [Chemical Formula 6]

[0069]

[0070]

[0071] Groups in which all hydrogen atoms present in Z1 to Z32 are substituted with deuterium atoms are exemplified herein as Z33 to Z64 in order. In some embodiments of the present invention, R 8 is selected from Z1 to Z64. In some embodiments of the present invention, R 8 is selected from Z1 to Z31 and Z33 to Z63. In some embodiments of the present invention, R 8is selected from Z1~Z22 and Z33~Z54. In some embodiments of the present invention, R 8 is selected from Z23~Z25 and Z55~Z57. In some embodiments of the present invention, R 8 is selected from Z26~Z31 and Z58~Z63. In some embodiments of the present invention, R 8 Z2~Z4, Z18~Z22, Z34~Z36, Z50~Z54 are selected. In some embodiments of the present invention, R 8 It is selected from Z1, Z5~Z17, Z23~Z33, Z37~Z49, Z55~Z63.

[0072] In general formula (1), A represents a ring structure. The ring structure referred to here includes a substituted ring structure. That is, A may take a structure in which a deuterium or a substituent is bonded to an atom of the atomic group forming the ring. The ring structure may be an aromatic ring or a non-aromatic ring. Preferably, A is a single aromatic ring or an aromatic ring formed by the condensation of 2 to 4 rings. The aromatic ring referred to here may be an aromatic ring in which the ring skeleton consists only of carbon atoms, or an aromatic ring in which the ring skeleton consists of carbon atoms and at least one heteroatom. That is, the aromatic ring that A can adopt may consist only of a ring in which the ring skeleton constituent atoms consist only of carbon atoms, or it may include a ring having at least one complex atom as a ring skeleton constituent atom. The number of rings constituting A is preferably one of 1 to 3, for example, 1, for example, 2, or for example, 3.

[0073] In the case where the ring skeleton is an aromatic ring composed solely of carbon atoms, each ring constituting A is a 4- to 7-membered ring in which the ring skeleton is composed solely of carbon atoms, preferably a 5- to 7-membered ring, and may be composed solely of, for example, a 6-membered ring (i.e., a benzene ring). In the case where A is composed of rings in which the ring skeleton constituent atoms are composed solely of carbon atoms, it is preferable that A contains at least one benzene ring. Examples of aromatic rings in which the ring skeleton is composed solely of carbon atoms that can be adopted by A include the benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, tetracene ring, chrysene ring, pyrene ring, and triphenylene ring. Additionally, examples include the pentarene ring, heptalene ring, biphenylene ring, as-indacene ring, s-indacene ring, acenaphtylene ring, fluoranthene ring, acephenanthrylene ring, aceanthrylene ring, and praiaden ring. In some embodiments of the present invention, A is selected from a benzene ring, a naphthalene ring, a phenanthrene ring, or an anthracene ring. In some embodiments of the present invention, A is a benzene ring. In some embodiments of the present invention, A is a naphthalene ring. In some embodiments of the present invention, A is a phenanthrene ring. As modes of condensation of A for the pyrimidine ring of general formula (1), benzo condensation, naphth[1,2] condensation, naphth[2,3] condensation, naphth[3,4] condensation, phenanth[1,2] condensation, phenanth[2,3] condensation, phenanth[3,4] condensation, phenanth[5,6] condensation, phenanth[6,7] condensation, phenanth[7,8] condensation, phenanth[9,10] condensation, anthraceno[1,2] condensation, anthraceno[2,3] condensation, and anthraceno[3,4] condensation may be used.

[0074] When A is an aromatic ring in which the ring skeleton consists of a carbon atom and at least one heteroatom, it is preferable that the heteroatom be one or more selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. In this case, one ring constituting A may include one heteroatom as a ring skeleton constituent atom, or it may include multiple heteroatoms. When multiple heteroatoms are included, those heteroatoms may be identical (e.g., all nitrogen atoms) or different (e.g., nitrogen atoms and oxygen atoms, e.g., nitrogen atoms and sulfur atoms). Also, when A is an aromatic ring formed by the condensation of 2 to 4 rings, heteroatoms may be included as ring skeleton constituent atoms in only some of the 2 to 4 rings, or heteroatoms may be included as ring skeleton constituent atoms in all rings. When heteroatoms are included as ring skeleton constituent atoms in multiple rings, each heteroatom may be identical or different. In some embodiments of the present invention, the heteroatoms constituting the ring skeleton of the aromatic ring of A are only oxygen atoms or sulfur atoms. In some embodiments of the present invention, the heteroatoms constituting the ring skeleton of the aromatic ring of A are only nitrogen atoms.

[0075] When A is an aromatic ring formed by the condensation of 2 to 4 rings, and the ring skeleton consists of a carbon atom and at least one heteroatom, it is preferable that A contains at least one benzene ring. An example can be given where A is an aromatic ring formed by the condensation of 3 rings, and 2 of the rings are benzene rings. An example can be given where A is an aromatic ring formed by the condensation of 4 rings, and 2 to 3 of the rings are benzene rings. In these cases, it is preferable that the ring at the position with the largest number of interposed rings between it and the pyrimidine ring of general formula (1) is a benzene ring. Among the rings constituting A, the ring condensed with the pyrimidine ring of general formula (1) may be a benzene ring, or it may be a ring containing a heteroatom as a ring skeleton constituent atom.

[0076] When A is an aromatic ring in which the ring skeleton consists of a carbon atom and at least one heteroatom, examples include a furan ring, a thiophene ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring. In some embodiments of the present invention, a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring may be adopted. In some embodiments of the present invention, A is a benzofuran ring, a benzothiophene ring, or an indole ring, for example, a benzofuran ring, or for example, a benzothiophene ring. It is preferable that the benzofuran ring, the benzothiophene ring, and the indole ring are each condensed into a furan ring, a thiophene ring, and a pyrrole ring, respectively, to the pyrimidine ring of general formula (1). In some embodiments of the present invention, A has a benzothienoid structure, a benzofuro structure, an indolo structure, a benzo structure, a naphthoid structure, or a phenantro structure. In some embodiments of the present invention, A is a benzothienoid structure, a benzofuro structure, or an indolo structure, for example, a benzothienoid structure or a benzofuro structure. In some embodiments of the present invention, A is a benzo structure, a naphthoid structure, or a phenantro structure, for example, a benzo structure or a naphthoid structure.

[0077] A hydrogen atom, a deuterium atom, or a substituent may be bonded to the constituent atom of the cyclic skeleton of the cyclic structure represented by A. The deuterium atom or substituent referred to herein may be selected from Group A, Group B, Group C, Group D, Group E, or any multiple of Groups A through E. In some embodiments of the present invention, a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group is bonded to the constituent atom of the cyclic skeleton of the cyclic structure represented by A. Regarding the substituted or unsubstituted alkyl group, the substituted or unsubstituted aryl group, or the substituted or unsubstituted heteroaryl group referred to herein, R 8 Refer to the corresponding description. In some embodiments of the present invention, at least one group represented by the following general formula (2') is bonded to the ring skeleton constituent atom of the ring structure represented by A. In some embodiments of the present invention, a hydrogen atom, a deuterium atom, or a group represented by the following general formula (2') is bonded to the ring skeleton constituent atom of the ring structure represented by A.

[0078] General formula (2')

[0079] [Chemical Formula 7]

[0080]

[0081] In general formula (2'), X 1 ' is N or CR 11 Represents ', X 2 ' is N or CR 12 Representing ', X 3 ' is N or CR 13 Represents ', X 4 ' is N or CR 14 Represents '. R 1 '~R 7Each represents independently a hydrogen atom, a deuterium atom, or a cyano group. * indicates a bonding position. X in general formula (2'). 1 '~X 4 ', R 11 '~R 14 ', R 1 '~R 7 Regarding the explanation and desirable range of ', X in the above general formula (2) 1 ~X 4 , R 11 ~R 14 , R 1 ~R 7 You can refer to the description and desirable range.

[0082] As examples of general formulas that specifically indicate the direction ring of A in general formula (1), general formulas (1a) to (1m) described later can be cited.

[0083] In this specification, "Group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., C1 to C40), an alkoxy group (e.g., C1 to C40), an alkylthio group (e.g., C6 to C30), an aryloxy group (e.g., C6 to C30), an arylthio group (e.g., C6 to C30), a heteroaryl group (e.g., C5 to C30), a heteroaryloxy group (e.g., C5 to C30), a heteroarylthio group (e.g., C5 to C30), an acyl group (e.g., C2 to C40), an alkenyl group (e.g., C2 to C40), an alkynyl group (e.g., C2 to C40), It is a group consisting of an alkoxycarbonyl group (e.g., 2 to 40 carbon atoms), an aryloxycarbonyl group (e.g., 7 to 40 carbon atoms), a heteroaryloxycarbonyl group (e.g., 4 to 40 carbon atoms), a silyl group (e.g., a trialkylsilyl group having 3 to 40 carbon atoms), and a nitro group. The alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, heteroaryl group, heteroaryloxy group, heteroarylthio group, acyl group, alkenyl group, alkyneyl group, alkoxycarbonyl group, aryloxycarbonyl group, heteroaryloxycarbonyl group, silyl group, and nitro group mentioned herein may be substituted with a substituent having a structure in which one or more of the above substituents are bonded to a deuterium atom constituting group A.

[0084] In this specification, "Group B" refers to a group consisting of a deuterium atom, an alkyl group (e.g., 1 to 40 carbon atoms), an alkoxy group (e.g., 1 to 40 carbon atoms), an aryl group (e.g., 6 to 30 carbon atoms), an aryloxy group (e.g., 6 to 30 carbon atoms), a heteroaryl group (e.g., 5 to 30 carbon atoms), a heteroaryloxy group (e.g., 5 to 30 carbon atoms), and a diarylamino group (e.g., 12 to 20 carbon atoms). The alkyl group, alkoxy group, aryl group, aryloxy group, heteroaryl group, heteroaryloxy group, and diarylamino group mentioned herein may be substituted with a substituent having a structure in which one or more of the above substituents are bonded to the deuterium atom constituting Group B.

[0085] In this specification, "Group C" refers to a group consisting of a deuterium atom, an alkyl group (e.g., 1 to 20 carbon atoms), an aryl group (e.g., 6 to 22 carbon atoms), a heteroaryl group (e.g., 5 to 20 atoms constituting a ring skeleton), and a diarylamino group (e.g., 12 to 20 carbon atoms). The alkyl group, aryl group, heteroaryl group, and diarylamino group mentioned herein may be substituted with a substituent having a structure in which one or more of the above substituents are bonded to the deuterium atom constituting Group C.

[0086] In this specification, "Group D" refers to a group consisting of a deuterium atom, an alkyl group (e.g., 1 to 20 carbon atoms), an aryl group (e.g., 6 to 22 carbon atoms), and a heteroaryl group (e.g., 5 to 20 atoms constituting a ring skeleton). The alkyl group, aryl group, and heteroaryl group mentioned herein may be substituted with a substituent having a structure in which one or more of the above substituents are bonded to the deuterium atom constituting Group D.

[0087] In this specification, "Group E" refers to a group consisting of a deuterium atom, an alkyl group (e.g., 1 to 20 carbon atoms), and an aryl group (e.g., 6 to 22 carbon atoms). The alkyl group and the aryl group referred to herein may be substituted with a substituent having a structure in which one or more of the deuterium atom constituting Group E and the above substituents are bonded.

[0088] In the present specification, the deuterium atom or substituent that is substituted when described as "substituted or unsubstituted" or "may be substituted" may be selected, for example, from Group A, from Group B, from Group C, from Group D, from Group E, or from each of the multiple groups A to E.

[0089] A compound represented by general formula (1) preferably has a structure represented by any one of the following general formulas (1a) to (1m).

[0090] [Chemical Formula 8]

[0091]

[0092] [Chemical Formula 9]

[0093]

[0094] R in general formulas (1a) to (1m) 21 ~R 25 Each independently represents a hydrogen atom, a deuterium atom, or a substituent, but R 21 ~R 25 At least one of them (e.g., one, e.g., two) is a group represented by the above general formula (2). For example, R 21 This is a group represented by the general formula (2). For example, R 22 is a group represented by the general formula (2). For example, R 23 This is a group represented by the general formula (2). In some embodiments of the present invention, R in general formulas (1a) to (1m)21 ~R 25 One of them is a group represented by general formula (2), and the others are each independently a hydrogen atom or a deuterium atom. R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 There are no cases where they all combine with each other to form a ring structure.

[0095] R in general formulas (1a) to (1m) 8 Regarding the definition and explanation of R in the above general formula (1), 8 You can refer to the definition and explanation of.

[0096] R in general formulas (1a) to (1m) a ~R m Each represents independently a hydrogen atom, a deuterium atom, or a substituent. The deuterium atom and substituent referred to herein may, for example, be selected from Group A described below, from Group B described below, from Group C described below, from Group D described below, from Group E described below, or from any multiple of Groups A through E. Adjacent R a ~R m They do not combine with each other to form a ring structure. In some embodiments of the present invention, R a ~R m Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In some aspects of the present invention, R a ~R mEach is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted heteroaryl group bonded to a carbon atom, e.g., a substituted or unsubstituted heteroaryl group bonded to a nitrogen atom). In some aspects of the present invention, R a ~R m Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group. In some embodiments of the present invention, R a ~R m It is a hydrogen atom, a deuterium atom, or a group represented by the general formula (2'), for example, R a ~R m At least one of them is a group represented by the general formula (2'). In some embodiments of the present invention, R a ~R m Each is independently a hydrogen atom or a deuterium atom.

[0097] In some embodiments of the present invention, a structure represented by general formula (1a) is adopted. In some embodiments of the present invention, a structure represented by any one of general formulas (1b) to (1e) is adopted, for example, a structure represented by general formula (1b), for example, a structure represented by general formula (1c), for example, a structure represented by general formula (1d), for example, a structure represented by general formula (1e). In some embodiments of the present invention, a structure represented by any one of general formulas (1f) to (1h) is adopted, for example, a structure represented by general formula (1f), for example, a structure represented by general formula (1g), for example, a structure represented by general formula (1h). In some embodiments of the present invention, a structure represented by any one of general formulas (1i) to (1k) is adopted, for example, a structure represented by general formula (1i), for example, a structure represented by general formula (1j), for example, a structure represented by general formula (1k). In some embodiments of the present invention, a structure represented by general formula (1m) is adopted. In addition, in some embodiments of the present invention, a structure represented by a general formula in which the upper N of general formulas (1a) to (1m) is substituted with CH is adopted. In addition, in some embodiments of the present invention, a structure represented by a general formula in which the lower N of general formulas (1a) to (1m) is substituted with CH is adopted.

[0098] In several embodiments of the present invention, R in each general formula of general formulas (1a) to (1m) 8 This is a substituted or unsubstituted aryl group (e.g., an aryl group having 6 to 40 carbon atoms that may be substituted with a deuterium atom or a cyano group), and R 23 This is a method represented by the general formula (2). In some embodiments of the present invention, R in each of the general formulas (1a) to (1m) 8 This is a substituted or unsubstituted aryl group (e.g., an aryl group having 6 to 40 carbon atoms that may be substituted with a deuterium atom or a cyano group), and R a ~R xEach is independently a hydrogen atom, a deuterium atom, or a group represented by general formula (2'). Here, x is d, f, f, f, h, d, d, i, h, h, m, g in order from general formula (1a) to general formula (1m). In some embodiments of the present invention, R in each of general formulas (1a) to (1m) 8 This is a substituted or unsubstituted aryl group (e.g., an aryl group having 6 to 40 carbon atoms that may be substituted with a deuterium atom or a cyano group), and R 23 This is a group represented by the general formula (2), and R a ~R x Each is a hydrogen atom, a deuterium atom, or a group represented by the general formula (2'), respectively. In this case, for example, R a ~R x One of them is a device represented by general formula (2'), and at that time, for example, the device represented by general formula (2) and the device represented by general formula (2') have the same structure.

[0099] In the table below, specific examples of compounds represented by general formula (1) are provided. The compounds represented by general formula (1) that can be employed in the present invention are not limited to the following specific examples.

[0100] Tables 1-1, 1-2, 2-1, 2-2, and 2-3 show specific examples of the compound represented by the general formula (1a). In Tables 1-1 and 1-2, R of the general formula (1a) 21 ~R 25 , R 8 , R a ~R d By specifying , the structures of compounds 1 to 194 are shown. For example, compound 1 is R 8 This is Z1, and R 23 This is D1, and R 21 , R 22 , R 24 , R 25 , R a ~Rd It is a compound having a structure in which all atoms are hydrogen atoms (H).

[0101] [Table 1-1]

[0102]

[0103] [Table 1-2]

[0104]

[0105] In Tables 2-1 through 2-3, R of general formula (1a) 8 , R 21 ~R 25 , R a ~R d By further specifying , the structures of compounds 1 to 24832 are shown. For example, in the first step of Table 2-1, R 23 It is written as "D1~D194". This is, R 8 Fix to Z1, and R 21 , R 22 , R 24 , R 25 , R a ~R d It fixes to a hydrogen atom (H), and R 23 The results obtained by changing D1 through D194 in order are collectively displayed as compounds 1 through 194. That is, the first column of Table 2-1 displays compounds 1 through 194 from Table 1 collectively in the first column. The second column of Table 2-1 is, R 8 Fix to Z2, and R 21 , R 22 , R 24 , R 25 , R a ~R d It fixes to a hydrogen atom (H), and R 23Compounds 195 through 388 are collectively represented by changing D1 through D194 in order. The structures from the third column onwards are specified in the same manner. In the following tables, the column labeled "FM" is the column specifying the general formula. In the column labeled "(1a)" in Tables 2-1 and 2-2, the structure of the compound represented by general formula (1a) is specified. Additionally, "D" in the following tables represents a deuterium atom.

[0106] [Table 2-1]

[0107]

[0108] [Table 2-2]

[0109]

[0110] [Table 2-3]

[0111]

[0112] Tables 3-1 through 3-4 show specific examples of compounds represented by general formula (1a) to general formula (1m). Here, each compound is identified by the “FM” column as to which general formula (1a) to general formula (1m) it is represented, and then R present in that general formula 8 , R 21 ~R 25 , R a ~R x The structures of compounds 1 to 943516 are shown by specifying (for general formulas (1a) to (1m), x is d, f, f, f, h, d, d, i, h, h, m, g, respectively). For example, in the first step of Table 3-1, R of the compound represented by general formula (1a) 21 , R 22 , R 24 , R 25 , R a ~R d Fix to a hydrogen atom (H), and R 8 Changing from Z1 to Z64, R 23Compounds 1 through 12416 are collectively represented as those modified from D1 to D194. Here, first, R 8 Fix it to Z1 and R 23 Compounds 1 through 194 are obtained by changing D1 through D194, and next, R 8 Fix it to Z2 and R 23 Compounds 195–388 are obtained by changing D1 through D194, and next, R 8 Fix it to Z3 and R 23 Compounds 1 to 12416 are identified by the method of changing D1 to D194 to form compounds 389 to 582. That is, the first column of Table 3-1 displays compounds 1 to 12416 from Tables 2-1 to 2-2 collectively in a single column. The structures of the compounds are identified collectively in the same manner in the second column and subsequent columns of Table 3-1. The second column of Table 3-1 is R of general formula (1a). 21 , R 22 , R 24 , R 25 , R a ~R d Fix to a deuterium atom (D), and R 8 Changing from Z1 to Z64, R 23 Compounds 12417–24832 are collectively represented as those modified from D1 to D194. The second column of Table 3-1 is a single column representing compounds 12417–24832 from Tables 2-2 through 2-3. The third column of Table 3-1 is R of general formula (1a). 21 , R 23 ~R 25 , R a ~R d Fix to a hydrogen atom (H), and R 8 Changing from Z1 to Z64, R 22Compounds 24833–37248 are collectively denoted as those modified from D1 to D194. Additionally, the rightmost column of Tables 3-1 through 3-4 indicates compounds with identical substituents. For example, in the group of compounds 99329–111744, R 22 and R 23 This indicates the same thing.

[0113] [Table 3-1]

[0114]

[0115] [Table 3-2]

[0116]

[0117] [Table 3-3]

[0118]

[0119] [Table 3-4]

[0120]

[0121] The compounds specified by the numbers above shall all be individually disclosed. Furthermore, among the specific examples of the compounds above, if rotational isomers exist, the mixture of rotational isomers and each separated rotational isomer shall also be disclosed in this specification.

[0122] In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 943516. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 74496. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 74497 to 148992. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 148993 to 223488. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 223489 to 297984. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 297985 to 372480. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 372481 to 446976 and compounds 893853 to 918684. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 446977 to 521472 and compounds 918685 to 943516. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 521473 to 595968. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 595969 to 670464. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 670465 to 744960. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 744961 to 819456. In some embodiments of the present invention, a compound is selected from the group of compounds consisting of compounds 819457 to 893952.

[0123] Specific examples of compounds represented by general formula (1) are given below.

[0124] [Chemical Formula 10]

[0125]

[0126] [Chemical Formula 11]

[0127]

[0128] [Chemical Formula 12]

[0129]

[0130] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, more preferably 1000 or less, and more preferably 800 or less, when the organic layer containing the compound represented by general formula (1) is intended to be formed and used by a deposition method. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1).

[0131] Compounds represented by general formula (1) can be formed into films by the coating method regardless of their molecular weight. By using the coating method, it is possible to form films even with compounds that have a relatively large molecular weight. Compounds represented by general formula (1) have the advantage of being easily soluble in organic solvents. For this reason, compounds represented by general formula (1) are easy to apply the coating method to and easy to purify to increase their purity.

[0132] In the present invention, it is also considered that a compound containing multiple structures represented by the general formula (1) within a molecule may be used as a light-emitting material or a delayed fluorescent material.

[0133] For example, it is conceived that a polymer is obtained by pre-preparing a polymerizable group within a structure represented by general formula (1) and polymerizing the polymerizable group, and that polymer is used as a light-emitting material. For example, it is conceived that a monomer containing a polymerizable functional group at any one part of general formula (1) is prepared, and that a polymer having repeating units is obtained by polymerizing it alone or copolymerizing it with another monomer, and that polymer is used as a light-emitting material. Alternatively, it is conceived that a dimer or a trimer is obtained by coupling compounds having a structure represented by general formula (1), and that they are used as light-emitting materials.

[0134] Examples of polymers having repeating units including a structure represented by general formula (1) include polymers including a structure represented by any one of the following two general formulas.

[0135] [Chemical Formula 13]

[0136]

[0137] In the above general formula, Q represents a group including a structure represented by general formula (1), and L 1 and L 2 represents a linker. The number of carbon atoms in the linker is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linker is -X 11 -L 11 It is desirable to have a structure that appears as -. Here, X 11 Silver represents an oxygen atom or a sulfur atom, and it is preferably an oxygen atom. L 11 The linker represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and is more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group.

[0138] In the above general formula, R 101 , R 102, R 103 and R 104 Each represents independently a hydrogen atom, a deuterium atom, or a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom; more preferably, it is an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom; and even more preferably, it is an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms.

[0139] L 1 and L 2 The connector shown can be connected to any part of the general formula (1) that constitutes Q. For one Q, two or more connectors may be connected to form a cross-linked structure or a mesh structure.

[0140] As a specific structural example of a repeating unit, a structure represented by the following formula can be cited.

[0141] [Chemical Formula 14]

[0142] A polymer having repeating units including these formulas can be synthesized by introducing a hydroxyl group at any one of the sites of general formula (1), reacting the following compound with the hydroxyl group as a linker to introduce a polymerizable group, and polymerizing the polymerizable group.

[0143] [Chemical Formula 15]

[0144]

[0145] A polymer containing a structure represented by general formula (1) within a molecule may be a polymer consisting only of repeating units having a structure represented by general formula (1), or a polymer containing repeating units having other structures. In addition, the repeating units having a structure represented by general formula (1) included in the polymer may be of a single type or two or more types. Examples of repeating units that do not have a structure represented by general formula (1) include those derived from monomers used in conventional copolymerization. For example, repeating units derived from monomers having ethylenically unsaturated bonds, such as ethylene and styrene, may be examples.

[0146] The compound represented by general formula (1) is a compound that can be used in various semiconductor devices. For example, it is thought to be used in organic light-emitting devices that emit light, organic light-receiving devices that receive light, or devices that generate energy transfer by light within the device. For example, an organic electroluminescent device can be fabricated using the compound represented by general formula (1). For example, a CMOS (complementary metal oxide semiconductor) can be fabricated using the compound represented by general formula (1). For example, a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using the compound represented by general formula (1).

[0147] Among the compounds represented by general formula (1), there are compounds capable of emitting delayed fluorescence. Among the compounds represented by general formula (1), there are compounds with a large proportion of delayed fluorescence components.

[0148] In one embodiment of the present disclosure, a compound represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, and red regions of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) or the near-infrared region when excited by thermal or electronic means.

[0149] In one embodiment of the present disclosure, the compound represented by general formula (1) can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means.

[0150] In one embodiment of the present disclosure, a compound represented by general formula (1) can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) when excited by thermal or electronic means.

[0151] In one embodiment of the present disclosure, a compound represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means.

[0152] In one embodiment of the present disclosure, a compound represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means.

[0153] In one embodiment of the present disclosure, a compound represented by general formula (1) can emit light in the ultraviolet spectral region (e.g., 280 to 400 nm) when excited by thermal or electronic means.

[0154] In one embodiment of the present disclosure, a compound represented by general formula (1) can emit light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by thermal or electronic means.

[0155] The electronic properties of a small molecule chemical library can be calculated using quantum chemical calculations based on known ab initio. For example, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) can be interpreted using time-dependent density functional theory with a group of functions known as Becke's three parameters, Lee-Yang-Parr hybrid functionals, as a basis, to screen for molecular fragments (parts) having HOMOs above a certain threshold and LUMOs below a certain threshold.

[0156] Thus, when there is a HOMO energy of -6.5 eV or higher (e.g., ionization potential), the donor portion ("D") can be selected. Also, when there is a LUMO energy of -0.5 eV or lower (e.g., electron affinity), the acceptor portion ("A") can be selected. The bridge portion ("B") is a strongly conjugated system that can strictly limit the acceptor and donor portions to a specific stereoconfiguration, for example, thereby preventing overlap between the π-conjugated systems of the donor and acceptor portions.

[0157] In one embodiment, the compound library is selected using one or more of the following characteristics.

[0158] 1. Luminescence near a specific wavelength

[0159] 2. Calculated triplet state above a specific energy level

[0160] 3. ΔE below a specific value ST value

[0161] 4. Quantum yield above a specific value

[0162] 5. HOMO level

[0163] 6. LUMO Level

[0164] In one embodiment, the difference (ΔE) between the lowest excited singlet state and the lowest excited triplet state at 77K ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, ΔE ST The value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV.

[0165] In one embodiment, the compound represented by general formula (1) exhibits a quantum yield of more than 25%, for example, 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.

[0166] [Method of synthesizing a compound represented by general formula (1)]

[0167] Compounds represented by general formula (1) include novel compounds.

[0168] The compound represented by general formula (1) can be synthesized by combining known reactions. For example, it can be synthesized by using a ring-closing reaction or a substitution reaction. For specific synthesis conditions, refer to the synthesis examples described below.

[0169] [Construction using a compound represented by general formula (1)]

[0170] In one embodiment, a solid film or layer is formed by combining a compound represented by general formula (1), dispersing the same compound, covalently bonding the same compound to the same compound, coating the same compound, supporting the same compound, or using one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that associate with the same compound. For example, a film can be formed by combining a compound represented by general formula (1) with an electroactive material. In some cases, a compound represented by general formula (1) may be combined with a hole transport polymer. In some cases, a compound represented by general formula (1) may be combined with an electron transport polymer. In some cases, a compound represented by general formula (1) may be combined with a hole transport polymer and an electron transport polymer. In some cases, a compound represented by general formula (1) may be combined with a copolymer having both a hole transport portion and an electron transport portion. By the above embodiments, electrons and / or holes formed within a solid film or layer can be interacted with a compound represented by general formula (1).

[0171] [Film Formation]

[0172] In one embodiment, a film containing a compound represented by general formula (1) can be formed in a wet process. In the wet process, a solution in which a composition containing a compound represented by general formula (1) is dissolved is applied to a surface, and a film is formed after the solvent is removed. Examples of wet processes include spin coating, slit coating, inkjet (spray) method, gravure printing, offset printing, and flexographic printing, but are not limited to these. In the wet process, a suitable organic solvent capable of dissolving a composition containing a compound represented by general formula (1) is selected and used. In one embodiment, a substituent (e.g., an alkyl group) that increases solubility in an organic solvent may be introduced into the compound included in the composition.

[0173] In one embodiment, a film containing a compound represented by general formula (1) can be formed in a dry process. In one embodiment, a vacuum deposition method may be adopted as the dry process, but it is not limited thereto. When a vacuum deposition method is adopted, the compounds constituting the film may be co-deposited from individual deposition sources, or they may be co-deposited from a single deposition source in which the compounds are mixed. When a single deposition source is used, a mixed powder in which the powders of the compounds are mixed may be used, a compressed molded body in which the mixed powder is compressed may be used, or a mixture in which each compound is heated, melted, and cooled may be used. In one embodiment, by performing co-depositing under conditions where the deposition rate (weight reduction rate) of a plurality of compounds included in a single deposition source is equal or approximately equal, a film with a composition ratio corresponding to the composition ratio of a plurality of compounds included in the deposition source can be formed. If a plurality of compounds are mixed in the same composition ratio as the composition ratio of the film to be formed and used as the deposition source, a film having a desired composition ratio can be easily formed. In one embodiment, a temperature at which each compound being co-deposited has the same weight loss rate can be specified and adopted as the temperature during co-depositing.

[0174] [Organic Light Emitting Diode]

[0175] An organic light-emitting device comprising a compound represented by general formula (1) is described. An organic light-emitting device using a compound represented by general formula (1) has excellent performance. For example, among organic light-emitting devices comprising a compound represented by general formula (1), there are those in which the device lifespan can be extended by using the compound represented by general formula (1). For example, among organic light-emitting devices comprising a compound represented by general formula (1), there are those in which the luminous efficiency is increased by using the compound represented by general formula (1). For example, among organic light-emitting devices comprising a compound represented by general formula (1), there are those in which the driving voltage is lowered by using the compound represented by general formula (1). For example, among organic light-emitting devices comprising a compound represented by general formula (1), there are those in which the ratio of the delayed fluorescence component during emission is increased by using the compound represented by general formula (1).

[0176] In some embodiments of the present invention, a compound represented by general formula (1) is used as a light-emitting material for an organic light-emitting device. For example, a compound represented by general formula (1) is used as a light-emitting material in a light-emitting layer. Among the compounds represented by general formula (1), there are compounds that contain a large amount of delayed fluorescence components. Therefore, in some embodiments of the present invention, a compound represented by general formula (1) is used as a delayed fluorescence material, and for example, delayed fluorescence is generated from the compound represented by general formula (1) to achieve high light emission efficiency. In some embodiments of the present invention, a compound represented by general formula (1) is used as a host material. In some embodiments of the present invention, a compound represented by general formula (1) is used together with one or more light-emitting materials. The light-emitting materials referred to herein may be fluorescent materials, phosphorescent materials, or delayed fluorescence materials. For example, a fluorescent material having a lower minimum excitation singlet energy than that of the compound represented by general formula (1) is used together with the compound represented by general formula (1). In some embodiments of the present invention, a compound represented by general formula (1) is used as a hole transport material. In some embodiments of the present invention, a compound represented by general formula (1) is used as an electron transport material.

[0177] In one embodiment, the light-emitting layer of the organic light-emitting device comprises a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by general formula (1) relative to the film-forming surface influences the direction of propagation of light emitted by the aligning compound, or determines the direction. In one embodiment, by aligning the direction of propagation of light emitted by the compound represented by general formula (1), the light extraction efficiency from the light-emitting layer is improved.

[0178] The organic light-emitting device of the present invention is preferably used as an organic light-emitting diode, etc. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of another light-emitting material included in the light-emitting layer (as a so-called assist dopant). In one embodiment, the lowest excitation singlet energy level of the compound represented by general formula (1) included in the light-emitting layer is between the lowest excitation singlet energy level of the host material included in the light-emitting layer and the lowest excitation singlet energy level of the other light-emitting material included in the light-emitting layer.

[0179] In one embodiment, the organic photoluminescence device comprises at least one light-emitting layer. In one embodiment, the organic electroluminescence device comprises at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer comprises at least a light-emitting layer. In one embodiment, the organic layer comprises only a light-emitting layer. In one embodiment, the organic layer comprises one or more organic layers in addition to the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer, and an exciton barrier layer. In one embodiment, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

[0180] Emissive layer:

[0181] In one embodiment, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In one embodiment, the layer emits light.

[0182] In one embodiment, only a light-emitting material is used as the light-emitting layer. In one embodiment, the light-emitting layer comprises a light-emitting material and a host material. In one embodiment, the light-emitting material is one or more compounds represented by general formula (1). In one embodiment, in order to improve the light emission efficiency of an organic electroluminescent device and an organic photoluminescent device, singlet excitons and triplet excitons generated in the light-emitting material are confined within the light-emitting material. In one embodiment, a host material is used in addition to the light-emitting material in the light-emitting layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has an excitation singlet energy and an excitation triplet energy, and at least one of them is higher than that of the light-emitting material of the present invention. In one embodiment, singlet excitons and triplet excitons generated in the light-emitting material of the present invention are confined within the molecules of the light-emitting material of the present invention. In one embodiment, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In one embodiment, although high light emission efficiency is still obtained, singlet excitons and triplet excitons are not sufficiently confined, that is, a host material capable of achieving high light emission efficiency is not particularly limited and can be used in the present invention. In one embodiment, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In one embodiment, the synchrotron includes both fluorescence and delayed fluorescence. In one embodiment, the synchrotron includes synchrotron from the host material. In one embodiment, the synchrotron consists of synchrotron from the host material. In one embodiment, the synchrotron includes synchrotron from the compound represented by general formula (1) and synchrotron from the host material. In one embodiment, a thermally activated delayed fluorescence material (TADF) and a host material are used.In one embodiment, TADF is an assist dopant, and has a lower excitation singlet energy than the host material in the light-emitting layer and a higher excitation singlet energy than the light-emitting material in the light-emitting layer.

[0183] In one embodiment, the organic electroluminescence device has a layer containing a compound represented by general formula (1). In one embodiment, the layer also includes a host material. In one embodiment, the layer containing the compound represented by general formula (1) and the host material also includes a delayed fluorescent material having a structure outside the range of general formula (1), and the lowest excitation singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound represented by general formula (1). In this case, in one embodiment, when the organic electroluminescence device is energized, the amount of light emitted from the compound represented by general formula (1) becomes maximum. In another embodiment, the organic electroluminescence device has a layer containing a compound represented by general formula (1) and a light-emitting material having a structure outside the range of general formula (1) (this layer may further include a host material). In one embodiment, the lowest excitation singlet energy of the light-emitting material having a structure outside the range of general formula (1) is lower than that of the compound represented by general formula (1). In one embodiment, when an organic electroluminescent element is energized, the amount of light emitted from a light-emitting material having a structure outside the range of general formula (1) becomes maximum.

[0184] When a compound represented by general formula (1) is used as an assist dopant, it is possible to use various compounds as a luminescent material (preferably a fluorescent material). As such luminescent materials, it is possible to use anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, zulolidine derivatives, thiazole derivatives, derivatives having a metal (Al, Zn), etc. These example frameworks may have substituents or may not have substituents. In addition, these example frameworks may be combined with each other.

[0185] In the following, examples of light-emitting materials that can be used in combination with an assist dopant having a structure represented by general formula (1) are provided.

[0186] [Chemical Formula 16]

[0187]

[0188]

[0189]

[0190]

[0191] In addition, compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 may also be particularly preferably employed as light-emitting materials used together with an assist dopant having a structure represented by general formula (1).

[0192] In addition, compounds represented by the following general formula (F1) can be cited as luminescent materials.

[0193] General formula (F1)

[0194] [Chemical Formula 17]

[0195]

[0196] In the general formula (F1), R 1 , R 3 ~R 16 Each represents a hydrogen atom, a deuterium atom, or a substituent independently. R 2 represents an acceptor genitalia, or R 1 and R 2 are combined with each other to form an acceptor, or R 2 and R 3 These combine with each other to form an acceptor genitalia. 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 They may combine with each other to form a ring structure. X 1 represents O or NR, and R represents a substituent. X 2 ~X 4 Middle, X 3 and X 4 At least one of them is O or NR, and the remainder may be O or NR or may not be connected. When not connected, both ends each independently represent a hydrogen atom, a deuterium atom, or a substituent. CR in general formula (F1) 1 , CR 3 , CR 4 , CR 5, CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 It may be replaced with N.

[0197] In some embodiments of the present invention, X 2 When is O or NR, R 7 This is an acceptor penis, or R 6 and R 7 These combine to form an acceptor genitalia, or R 7 and R 8 These combine with each other to form an acceptor genitalia. In some embodiments of the present invention, X 3 When this is O or NR, R 10 This is an acceptor penis, or R 9 and R 10 These combine to form an acceptor genitalia, or R 10 and R 11 These combine with each other to form an acceptor genitalia. In some embodiments of the present invention, X 4 When is O or NR, R 15 is an acceptor or R 14 and R 15 are combined with each other to form an acceptor, or R 15 and R 16 These combine with each other to form an acceptor genitalia. In some embodiments of the present invention, X 2 α is NR, R is a substituted or unsubstituted phenyl group, and R 8 When a carbazole ring is formed by directly bonding to the bonded carbon atom, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group. In some aspects of the present invention, X 3This is NR, where R is a substituted or unsubstituted phenyl group and R 9 When a carbazole ring is formed by directly bonding to a carbon atom to which it is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group. In some aspects of the present invention, X 4 α is NR, R is a substituted or unsubstituted phenyl group, and R 16 When a carbazole ring is formed by directly bonding to a carbon atom to which it is bonded, at least one of the 3rd and 6th positions of the carbazole ring is substituted with an acceptor group. In some aspects of the present invention, X 1 This is NR, where R is a substituted or unsubstituted phenyl group and R 1 When a carbazole ring is formed by directly bonding to the carbon atom, the third position of the carbazole ring is substituted with an acceptor group (wherein the third position is present on the phenyl group). In some embodiments of the present invention, the compound is represented by the following general formula (F2).

[0198] General formula (F2)

[0199] [Chemical Formula 18]

[0200]

[0201] In the general formula (F2), R 1 , R 3 , R 6 ~R 11 , R 14 ~R 16 Each represents a hydrogen atom, a deuterium atom, or a substituent independently. R 2 represents an acceptor genitalia, or R 1 and R 2 are combined with each other to form an acceptor, or R 2 and R 3 These combine to form an acceptor genitalia.

[0202] R 6 and R 7 , R 7and R 8 , R 9 and R 10 , R 10 and R 11 , R 14 and R 15 , R 15 and R 16 They may combine with each other to form a ring structure. X 1 represents O or NR, and R represents a substituent. X 2 ~X 4 Middle, X 3 and X 4 At least one of them is O or NR, and the remainder may be O or NR or may not be connected. When not connected, both ends each independently represent a hydrogen atom, a deuterium atom, or a substituent. Ar 1 and Ar 2 represents, respectively, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. CR in general formula (F2) 1 , CR 3 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 14 , CR 15 , CR 16 It may be replaced with N.

[0203] In addition, compounds represented by the following general formula (F3) can be cited as luminescent materials.

[0204] General formula (F3)

[0205] [Chemical Formula 19]

[0206]

[0207] In the general formula (F3), R 1 and R 2Each represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R 3 ~R 16 Each represents a hydrogen atom, a deuterium atom, or a substituent independently. R 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 2 , R 2 and 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 They may be combined to form a ring structure. CR in general formula (F3) 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 It may be replaced with N.

[0208] In some aspects of the present invention, R 1 and R 2 is a substituted or unsubstituted phenyl group to which another ring may be independently condensed. In some embodiments of the present invention, R 3 and R 10 Each is independently a substituted amino group. In some embodiments of the present invention, R 1 and R 3 , and, R 2 and R 10 At least one combination of these forms a ring structure. In some embodiments of the present invention, the ring structure comprises a benzoazaboline ring.

[0209] In addition, compounds represented by the following general formula (F4) can be cited as light-emitting materials.

[0210] General formula (F4)

[0211] [Chemical Formula 20]

[0212]

[0213] In the general formula (F4), Z 1 and Z 2 represents, respectively, a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted complex aromatic ring, and R 1 ~R 9 represents, respectively, 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 They may combine with each other to form a ring structure. However, Z 1 , Z 2 , R1 and R 2 A ring formed by combining with each other, R 2 and R 3 The ring formed by these combining, R 4 and R 5 A ring formed by combining with each other, and R 5 and R 6 At least one of the rings formed by combining these 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 also, R 1 ~R 9 At least one of them is a substituted or unsubstituted aryl group or an acceptor group, or, Z 1 and Z 2 At least one of them is a ring having an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton of the benzofuran ring, the benzothiophene ring, and the indole ring, the substitutable carbon atoms may be substituted with nitrogen atoms. CR in general formula (F4) 1 , CR 2 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 ...may be replaced with N.

[0214] In some embodiments of the present invention, Z 1 and Z 2 a, each independently a substituted or unsubstituted non-condensed benzene ring, a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, and a pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring. In some embodiments of the present invention, R 1 ~R 9 a, each independently a substituted or unsubstituted aryl group or an acceptor group, or, R 1 and R 2A ring formed by combining with each other, R 2 and R 3 The ring formed by these combining, R 4 and R 5 A ring formed by combining with each other, and R 5 and R 6 One or more rings selected from the group consisting of rings formed by combining these are a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or a pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring. In some aspects of the present invention, R 8 This is a substituted or unsubstituted aryl group or an acceptor group. In some embodiments of the present invention, two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring are included.

[0215] In addition, as a luminescent material, a compound having a condensed ring structure A (where hydrogen atoms in the structure may be replaced with deuterium atoms or substituents) in which a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring is condensed at the carbon-carbon bond a of the following structure α, or a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring, or a benzene ring constituting a substituted or unsubstituted dibenzodioxane ring is condensed at the carbon-carbon bond b.

[0216] Structure α

[0217] [Chemical Formula 21]

[0218]

[0219] In structure α, X 1 and X 2represents a nitrogen atom or an oxygen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is attached, respectively, Z represents a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted complex aromatic ring, and R 1 represents a hydrogen atom, a deuterium atom, or a substituent, and Z and X 2 They may combine with each other to form a circular structure.

[0220] In condensed ring structure A, the structure condensed at b and X 1 , structure condensed to b and Z, Z and X 2 They may combine with each other to form a circular structure.

[0221] In addition, compounds represented by the following general formula (F5) can be cited as light-emitting materials.

[0222] General formula (F5)

[0223] [Chemical Formula 22]

[0224]

[0225] In the general formula (F5), Z 1 Silver represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and Z 2 and Z 3 Each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 represents a hydrogen atom, a deuterium atom, or a substituent, and R 2 and R 3 Each represents an independently substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 , R 2 Wow Z 2 , Z 2 Wow Z 3 , Z3 and R 3 They may combine with each other to form a ring structure. However, R 2 Wow Z 2 , Z 2 Wow Z 3 , Z 3 and R 3 At least one set of them combines with each other to form a circular structure.

[0226] In addition, compounds represented by the following general formula (F6) can be cited as light-emitting materials.

[0227] General formula (F6)

[0228] [Chemical Formula 23]

[0229]

[0230] In the general formula (F6), X 3 Silver represents an oxygen or sulfur atom, and Z 2 and Z 3 Each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 and R 4 ~R 7 represents a hydrogen atom, a deuterium atom, or a substituent, and R 2 and R 3 Each represents an independently substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 Wow Z 2 , Z 2 Wow Z 3 , Z 3 and R 3 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 They may combine with each other to form a ring structure. However, R 2 Wow Z 2 , Z 2 Wow Z 3 , Z 3 and R3 At least one set of them combines with each other to form a circular structure.

[0231] In addition, compounds represented by the following general formula (F7) can be cited as light-emitting materials.

[0232] General formula (F7)

[0233] [Chemical Formula 24]

[0234]

[0235] In the general formula (F7), X 4 represents an oxygen atom or a sulfur atom, and Z 2 and Z 3 Each independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 and R 4a ~R 7a represents a hydrogen atom, a deuterium atom, or a substituent, and R 2 and R 3 Each represents an independently substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 Wow Z 2 , Z 2 Wow 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 They may combine with each other to form a ring structure. However, R 2 Wow Z 2 , Z 2 Wow Z 3 , Z 3 and R 3 At least one set of them combines with each other to form a circular structure.

[0236] In addition, compounds represented by the following general formula (F8) can be cited as luminescent materials.

[0237] General formula (F8)

[0238] [Chemical Formula 25]

[0239]

[0240] In the general formula (F8), Z 1 represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and Z 3 represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 and R 8 ~R 14 Each independently represents 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 , 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 Wow Z 3 , Z 3 and R 3 They may combine with each other to form a ring structure.

[0241] In addition, compounds represented by the following general formula (F9) can be cited as light-emitting materials.

[0242] General formula (F9)

[0243] [Chemical Formula 26]

[0244]

[0245] In the general formula (F9), Z 1 and Z 4 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and Z 3 represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 and R 15 ~R 17 Each independently represents 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 They may combine with each other to form a ring structure.

[0246] In addition, compounds represented by the following general formula (F10) can be cited as luminescent materials.

[0247] General formula (F10)

[0248] [Chemical Formula 27]

[0249]

[0250] In the general formula (F10), Z 1 and Z 5 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and Z 3represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 represents a hydrogen atom, a deuterium atom, or a substituent, and R 2 and R 3 Each represents an independently substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 , R 2 Wow Z 5 , Z 5 Wow Z 3 , Z 3 and R 3 They may combine with each other to form a ring structure. However, R 2 Wow Z 5 , Z 5 Wow Z 3 , Z 3 and R 3 At least one set of them combines with each other to form a circular structure.

[0251] In addition, compounds represented by the following general formula (F11) can be cited as luminescent materials.

[0252] General formula (F11)

[0253] [Chemical Formula 28]

[0254]

[0255] In the general formula (F11), Z 1 represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and Z 2 represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 and R 21 ~R 27 Each independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 2represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 , R 2 Wow Z 2 , Z 2 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 , R 26 and R 27 They may combine with each other to form a ring structure.

[0256] In addition, compounds represented by the following general formula (F12) can be cited as luminescent materials.

[0257] General formula (F12)

[0258] [Chemical Formula 29]

[0259]

[0260] In the general formula (F12), Z 1 and Z 6 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and Z 2 represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 and R 28 ~R 30 Each independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 , R 2 Wow Z 2 , Z 2and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and Z 6 They may combine with each other to form a ring structure.

[0261] In addition, compounds represented by the following general formula (F13) can be cited as luminescent materials.

[0262] General formula (F13)

[0263] [Chemical Formula 30]

[0264]

[0265] In the general formula (F13), Z 1 and Z 7 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and Z 2 represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted complex aromatic ring, and R 1 represents a hydrogen atom, a deuterium atom, or a substituent, and R 2 and R 3 Each represents an independently substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 Wow Z 2 , Z 2 Wow Z 7 , Z 7 and R 3 They may combine with each other to form a ring structure. However, R 2 Wow Z 2 , Z 2 Wow Z 7 , Z 7 and R 3 At least one set of them combines with each other to form a circular structure.

[0266] In addition, compounds represented by the following general formula (F14) can be cited as luminescent materials.

[0267] General formula (F14)

[0268] [Chemical Formula 31]

[0269]

[0270] In the general formula (F14), Z 1 represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and R 1 and R 31 ~R 44 Each represents an independently 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 R 36 , R 36 and R 37 , R 37 and R 38 , R 38 and R 39 , R 39 and R 40 , R 40 and R 41 , R 41 and R 42 , R 42 and R 43 , R 43 and R 44 They may combine with each other to form a circular structure.

[0271] In addition, compounds represented by the following general formula (F15) can be cited as luminescent materials.

[0272] General formula (F15)

[0273] [Chemical Formula 32]

[0274]

[0275] In the general formula (F15), Z 1 and Z 8 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and R 1 and R 51 ~R 60 Each represents a hydrogen atom, a deuterium atom, or a substituent independently. 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 They may combine with each other to form a ring structure.

[0276] In addition, compounds represented by the following general formula (F16) can be cited as luminescent materials.

[0277] General formula (F16)

[0278] [Chemical Formula 33]

[0279]

[0280] In the general formula (F16), Z 1 , Z 8 and Z 9Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and R 1 and R 61 ~R 66 Each represents a hydrogen atom, a deuterium atom, or a substituent independently. 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 They may combine with each other to form a ring structure.

[0281] In addition, compounds represented by the following general formula (F17) can be cited as luminescent materials.

[0282] General formula (F17)

[0283] [Chemical Formula 34]

[0284]

[0285] In the general formula (F17), Z 1 , Z 9 and Z 10 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and R 1 and R 67 ~R 69 Each independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 70 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z1 , Z 9 and R 67 , R 67 and R 68 , R 68 and R 69 , R 69 Wow Z 10 , Z 10 and R 70 They may combine with each other to form a ring structure.

[0286] In addition, compounds represented by the following general formula (F18) can be cited as luminescent materials.

[0287] General formula (F18)

[0288] [Chemical Formula 35]

[0289]

[0290] In the general formula (F18), Z 1 , Z 11 and Z 12 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and R 1 and R 72 ~R 74 Each independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 71 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 71 and Z 11 , Z 11 and R 72 , R 72 and R 73 , R 73 and R 74 , R 74 Wow Z 12 They may combine with each other to form a circular structure.

[0291] In addition, compounds represented by the following general formula (F19) can be cited as luminescent materials.

[0292] General formula (F19)

[0293] [Chemical Formula 36]

[0294]

[0295] In the general formula (F19), Z 1 and Z 11 Each independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, and R 1 and R 76 ~R 82 Each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R 75 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 , R 75 Wow 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 They may combine with each other to form a circular structure.

[0296] In addition, compounds represented by the following general formula (F20) can be cited as luminescent materials.

[0297] General formula (F20)

[0298] [Chemical Formula 37]

[0299]

[0300] In the general formula (F20), X 5represents an oxygen atom, a sulfur atom, or a nitrogen atom bonded to a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and R 101 ~R 130 Each independently represents a hydrogen atom, a deuterium atom, or a substituent, and R 101 and R 102 , R 102 and R 103 , R 103 and R 104 , R 104 and R 105 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 109 and R 110 , R 110 and R 111 , R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 114 and R 115 , R 115 and R 116 , R 116 and R 117 , R 117 and R 118 , R 118 and R 119 , R 119 and R 120 , R 120 and R 121 , R 121 and R 122 , R 122 and R 123 , R 123 and R 124 , R 124 and R 125 , R 125 and R 126 , R 126 and R 127 , R 127 and R128 , R 128 and R 129 , R 129 and R 130 , R 130 and R 101 They may combine with each other to form a ring structure.

[0301] In addition, compounds represented by the following general formula (F21) can be cited as luminescent materials.

[0302] General formula (F21)

[0303] [Chemical Formula 38]

[0304]

[0305] In the general formula (F21), R 1 and R 2 Each represents independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Z 1 and Z 2 represents, respectively, a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted complex aromatic ring, and R 3 ~R 9 represents, respectively, a hydrogen atom, a deuterium atom, or a substituent. provided that R 1 , R 2 , Z 1 and Z 2 At least one of them comprises 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 Wow Z 2 , Z 2 and R 2 , R 2 and R 6 , R 6 and R7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 They may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring backbone of the benzofuran ring, the benzothiophene ring, and the indole ring, the substitutable carbon atoms may be replaced with nitrogen atoms. CR in general formula (F21) 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 ...may be replaced with N.

[0306] In some aspects of the present invention, R 1 and R 2 a is a group comprising one or more ring structures selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophen ring, and a substituted or unsubstituted indole ring, each independently. In some aspects of the present invention, Z 1 and Z 2 a, each independently a substituted or unsubstituted non-condensed benzene ring, a furan ring condensed from a substituted or unsubstituted benzene ring, a thiophene ring condensed from a substituted or unsubstituted benzene ring, a pyrrole ring condensed from a substituted or unsubstituted benzene ring, a benzene ring condensed from a substituted or unsubstituted benzofuran ring, a benzene ring condensed from a substituted or unsubstituted benzothiophene ring, or a benzene ring condensed from a substituted or unsubstituted indole ring. In some embodiments of the present invention, R 1 and Z 1 These combine with each other to form a ring structure. In some embodiments of the present invention, R 1 and Z 1 These combine to form pyrrole rings.

[0307] In addition, compounds represented by the following general formula (F22) can be cited as luminescent materials.

[0308] General formula (F22)

[0309] [Chemical Formula 39]

[0310]

[0311] In the general formula (F22), X 1 and X 2 One side is a nitrogen atom, and the other side is a boron atom. R 1 ~R 26 , A 1 , A 2 represents, respectively, 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 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22, R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 Silver may combine with one another to form a ring structure. However, X 1 When this is a nitrogen atom, R 17 and R 18 They combine with each other to form single bonds, creating a pyrrole ring, and X 2 When is a nitrogen atom, R 21 and R 22 They combine with each other to form single bonds, creating a pyrrole ring. However, X 1 This is a nitrogen atom, and R 7 and R 8 and R 21 and R 22 G bonds via a nitrogen atom to form a six-membered ring, and R 17 and R 18 When these are combined to form a single bond, R 1 ~R 6 At least one of them is a substituted or unsubstituted aryl group, or 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 One of them combines with another to form an aromatic hydrocarbon ring or a complex aromatic ring.

[0312] For a detailed description of the compound represented by the general formula (F22) and preferred ranges and specific examples, refer to

[0010] through

[0119] of WO2022 / 270354A1, which is incorporated herein as part of this specification.

[0313] In addition, compounds represented by the following general formula (F23) can be cited as luminescent materials.

[0314] General formula (F23)

[0315] [Chemical Formula 40]

[0316]

[0317] In the general formula (F23), R 1 ~R 22 represents, respectively, 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, R and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R, R and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 ...may combine with each other to form a ring structure. X 1 and X 2Each represents O, S, or NR independently. R represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of compounds included in this general formula include the compound represented by the general formula

[0022] of WO2022 / 085714A1, which is cited herein as part of this specification, the compounds described in

[0040] to

[0043] and

[0221] , and BBCz-R (5) and BBCz-Y-II (6) of J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which is cited herein as part of this specification.

[0318] In addition, compounds represented by the following general formula (F24) can be cited as luminescent materials.

[0319] General formula (F24)

[0320] [Chemical Formula 41]

[0321]

[0322] In the general formula (F24), R 1 ~R 17 Each represents a hydrogen atom, a deuterium atom, or a substituent independently. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , 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 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15and R 16 , R 16 and R 17 , R 17 and R 1 The compounds may be combined to form a cyclic structure. Examples of compounds included in this general formula include BBCz-SB (2), BBCz-G (3), and BBCz-Y (4) of J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which are cited herein as part of this specification.

[0323] In addition, compounds represented by the following general formula (F25) can be cited as luminescent materials.

[0324] General formula (F25)

[0325] [Chemical Formula 42]

[0326]

[0327] In the general formula (F25), R 1 ~R 20 Each represents a hydrogen atom, a deuterium atom, or a substituent independently. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , 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 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 17 and R 18 , R 18 and R19 , R 19 and R 20 The compounds may be bonded together to form a cyclic structure. As a compound included in this general formula, BBCz-DB (1) of J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which is cited herein as part of this specification, may be cited.

[0328] In addition, compounds represented by the following general formula (F26) can be cited as light-emitting materials.

[0329] General formula (F26)

[0330] [Chemical Formula 43]

[0331]

[0332] In the general formula (F26), X 1 and X 2 Each independently represents O or S. Y 1 and Y 2 Each is independently a single bond, O, S, or C(R a )(R b Represents ). R 1 ~R 22 , R a , R b Each independently represents a hydrogen atom, a deuterium atom, or a substituent, but R 1 ~R 22 At least one of them is a substituent. R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and Y 1 , Y 1 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10and R 11 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and Y 2 , Y 2 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 They may combine with each other to form a ring structure. R 21 and R 1 , R 4 and R 5 , R 10 and R 12 , R 15 and R 16 They are not bonded to each other to form a ring structure. CR in general formula (F26) 1 , CR 2 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 , CR 17 , CR 18 , CR 19 , CR 20 , CR 21 , CR 22 ...may be replaced with N.

[0333] Specific examples of compounds represented by the general formula (F26) include the following compounds.

[0334] [Chemical Formula 44]

[0335]

[0336]

[0337] In addition, compounds containing the BODIPY(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) structure can be used as luminescent materials. For example, a compound represented by the following general formula (F27) is used.

[0338] General formula (F27)

[0339] [Chemical Formula 45]

[0340]

[0341] In the general formula (F27), R 1 ~R 9 are each independently a hydrogen atom, a deuterium atom, or a substituent. R 1 ~R 7 At least one of them is preferably represented by the following general formula (F28), and R 8 and R 9 It is preferable that it be a halogen atom.

[0342] General formula (F28)

[0343] [Chemical Formula 46]

[0344]

[0345] In the general formula (F28), R 11 ~R 15 Each represents a hydrogen atom, a deuterium atom, or a substituent independently, and * represents a bonding position.

[0346] Specific examples of luminescent materials are provided below. In the structural formulas below, t-Bu represents a tertiary butyl group. As derivatives of the following example compounds, compounds in which at least one hydrogen atom is substituted with a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, or a diarylamino group may be provided.

[0347] [Chemical Formula 47]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353] In one embodiment, when using a host material, the amount of the compound used in the present invention as a light-emitting material included in the light-emitting layer is 0.1 wt% or more. In one embodiment, when using a host material, the amount of the compound of general formula (1) as a light-emitting material included in the light-emitting layer is 1 wt% or more. In one embodiment, when using a host material, the amount of the compound of general formula (1) as a light-emitting material included in the light-emitting layer is 50 wt% or less. In one embodiment, when using a host material, the amount of the compound of general formula (1) as a light-emitting material included in the light-emitting layer is 20 wt% or less. In one embodiment, when using a host material, the amount of the compound of general formula (1) as a light-emitting material included in the light-emitting layer is 10 wt% or less.

[0354] In one embodiment, the host material of the emitting layer is an organic compound having hole transport and electron transport functions. In one embodiment, the host material of the emitting layer is an organic compound that prevents the wavelength of the synchrotron radiation from increasing. In one embodiment, the host material of the emitting layer is an organic compound having a high glass transition temperature.

[0355] In some embodiments, the host material is selected from the group consisting of the following:

[0356] [Chemical Formula 48]

[0357]

[0358]

[0359]

[0360] In one embodiment, the light-emitting layer comprises two or more types of TADF molecules with different structures. For example, the light-emitting layer may comprise three types of materials in which the excitation singlet energy levels are higher in the order of the host material, the first TADF molecule, and the second TADF molecule. In this case, the first TADF molecule and the second TADF molecule together have the difference ΔE between the lowest excitation singlet energy level and the lowest excitation triplet energy level of 77K. STIt is preferable that the value is 0.3 eV or less, more preferable that it is 0.25 eV or less, more preferable that it is 0.2 eV or less, more preferable that it is 0.15 eV or less, more preferable that it is 0.1 eV or less, more preferable that it is 0.07 eV or less, even more preferable that it is 0.05 eV or less, even more preferable that it is 0.03 eV or less, and particularly preferable that it is 0.01 eV or less. It is preferable that the concentration of the first TADF molecule in the light-emitting layer is greater than the concentration of the second TADF molecule. Also, it is preferable that the concentration of the host material in the light-emitting layer is 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, smaller than, or equal to the concentration of the host material. In one embodiment, the composition within the light-emitting layer may be 10 to 70 wt% of the host material, 10 to 80 wt% of the first TADF molecule, and 0.1 to 30 wt% of the second TADF molecule. In one embodiment, the composition within the light-emitting layer may be 20 to 45 wt% of the host material, 50 to 75 wt% of the first TADF molecule, and 5 to 20 wt% of the second TADF molecule. In one embodiment, the light emission quantum yield φPL1(A) by photo-excitation of the co-deposited film of the first TADF molecule and the host material (concentration of the first TADF molecule in this co-deposited film = A wt%) and the light emission quantum yield φPL2(A) by photo-excitation of the co-deposited film of the second TADF molecule and the host material (concentration of the second TADF molecule in this co-deposited film = A wt%) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the light emission quantum yield φPL2(B) by photo-excitation of a co-deposited film of the second TADF molecule and a host material (concentration of the second TADF molecule in this co-deposited film = B wt%) and the light emission quantum yield φPL2(100) by photo-excitation of a single film of the second TADF molecule satisfy the relationship φPL2(B) > φPL2(100).In one embodiment, the light-emitting layer may include three types of TADF molecules with different structures. The compound of general formula (1) may be any of the plurality of TADF compounds included in the light-emitting layer.

[0361] In one embodiment, the light-emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain a metal element. In one embodiment, the light-emitting layer may be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer may be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer may be composed of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

[0362] When the light-emitting layer includes a TADF material other than the compound of general formula (1), the TADF material may be a known delayed fluorescent material. As a preferred delayed fluorescence material, paragraphs 0008–0048 and 0095–0133 of WO2013 / 154064, paragraphs 0007–0047 and 0073–0085 of WO2013 / 011954, paragraphs 0007–0033 and 0059–0066 of WO2013 / 011955, paragraphs 0008–0071 and 0118–0133 of WO2013 / 081088, paragraphs 0009–0046 and 0093–0134 of Japanese Patent Publication No. 2013-256490, paragraphs 0008–0020 and 0038–0040 of Japanese Patent Publication No. 2013-116975, Paragraphs 0007–0032 and 0079–0084 of WO2013 / 133359, paragraphs 0008–0054 and 0101–0121 of WO2013 / 161437, paragraphs 0007–0041 and 0060–0069 of Japanese Published Patent Application No. 2014-9352, paragraphs 0008–0048 and 0067–0076 of Japanese Published Patent Application No. 2014-9224, paragraphs 0013–0025 of Japanese Published Patent Application No. 2017-119663, paragraphs 0013–0026 of Japanese Published Patent Application No. 2017-119664, and paragraph of Japanese Published Patent Application No. 2017-222623 Compounds included in the general formulas described in paragraphs 0012~0025, paragraphs 0010~0050 of Japanese Patent Publication No. 2017-226838, paragraphs 0012~0043 of Japanese Patent Publication No. 2018-100411, and paragraphs 0016~0044 of WO2018 / 047853, particularly exemplary compounds capable of emitting delayed fluorescence.Also, herein, Japanese Published Patent Application 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, The luminescent material described in WO2015 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, and Japanese Published Patent Application No. 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541 is preferably capable of emitting delayed fluorescence. It may be adopted. Additionally, the above publication described in this paragraph is incorporated herein by reference as part of this specification.

[0363] In the following, each component of the organic electroluminescence device and each layer other than the light-emitting layer will be described.

[0364] write:

[0365] In some embodiments, the organic electroluminescence element of the present invention is supported by a substrate, and said substrate is not particularly limited and any one of the materials formed by glass, transparent plastic, quartz and silicon, which are generally used in organic electroluminescence elements, may be used.

[0366] anode:

[0367] In some embodiments, the anode of the organic electroluminescence device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is fabricated by deposition or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not require high precision (e.g., about 100 μm or higher), the pattern may be formed using a mask of a shape suitable for deposition or sputtering on the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film forming method such as a printing method or a coating method is used. In some embodiments, when synchrotron radiation passes through the anode, the anode has a transmittance of more than 10%, and said anode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0368] cathode:

[0369] In some embodiments, the cathode is made of an electrode material having a low work function (4 eV or less) (referred to as an electron injection metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of the electron injection metal and a second metal, which is a stable metal having a higher work function than the electron injection metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection characteristics and resistance to oxidation. In some embodiments, the cathode is manufactured by forming a thin film of electrode material by deposition or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the cathode is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescence device is transparent or translucent in order to transmit synchrotron radiation. In some embodiments, the transparent or translucent electroluminescence device improves light emission brightness.

[0370] In some embodiments, the cathode is formed from a conductive transparent material as described above with respect to the anode, thereby forming a transparent or translucent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or translucent.

[0371] Injection layer:

[0372] The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage to increase the light emission brightness. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer may be disposed between the anode and the emitting layer or hole transport layer, and between the cathode and the emitting layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present.

[0373] Below are examples of desirable compounds that can be used as hole injection materials.

[0374] [Chemical Formula 49]

[0375]

[0376] Next, examples of desirable compounds that can be used as electron injection materials are provided.

[0377] [Chemical Formula 50]

[0378]

[0379] Barrier layer:

[0380] A barrier layer is a layer capable of preventing charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outward from the light-emitting layer. In some embodiments, an electron barrier layer exists between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to reach the hole transport layer. In some embodiments, a hole barrier layer exists between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to reach the electron transport layer. In some embodiments, the barrier layer prevents excitons from diffusing outward from the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. The terms "electron barrier layer" or "exciton barrier layer" as used herein include a layer having both the function of an electron barrier layer and the function of an exciton barrier layer.

[0381] Hole barrier layer:

[0382] The hole barrier layer functions as an electron transport layer. In some embodiments, during electron transport, the hole barrier layer prevents holes from reaching the electron transport layer. In some embodiments, the hole barrier layer increases the probability of electron-hole recombination in the emissive layer. The material used for the hole barrier layer may be the same material as described above for the electron transport layer.

[0383] Below are examples of preferred compounds that can be used in hole barrier layers.

[0384] [Chemical Formula 51]

[0385]

[0386] Electronic barrier layer:

[0387] The electron barrier layer transports holes. In some embodiments, during hole transport, the electron barrier layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron barrier layer increases the probability of electron and hole recombination in the light-emitting layer. The material used for the electron barrier layer may be the same material as described above for the hole transport layer.

[0388] Specific examples of desirable compounds that can be used as electronic barrier materials are given below.

[0389] [Chemical Formula 52]

[0390]

[0391]

[0392] Female Journalist Barrier Layer

[0393] The exciton barrier layer prevents excitons generated through the recombination of holes and electrons in the emitting layer from diffusing to the electron transport layer. In some embodiments, the exciton barrier layer enables effective confinement of excitons in the emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton barrier layer may be located adjacent to only one of the anode side or the cathode side of the emitting layer, or one exciton barrier layer may be located adjacent to the anode side of the emitting layer while another exciton barrier layer is located adjacent to the cathode side of the emitting layer. In some embodiments, when the exciton barrier layer is located on the anode side, the layer may be located between the hole transport layer and the emitting layer and adjacent to the emitting layer. In some embodiments, when the exciton barrier layer is located on the cathode side, the layer may be located between the emitting layer and the cathode and adjacent to the emitting layer. In some embodiments, the hole injection layer, the electron barrier layer, or the same layer exists between the anode and the exciton barrier layer adjacent to the emitting layer on the anode side. In some embodiments, the hole injection layer, the electron barrier layer, the hole barrier layer, or the same layer exists between the cathode and the exciton barrier layer adjacent to the emitting layer on the cathode side. In some embodiments, the exciton barrier layer includes an excitation singlet energy and an excitation triplet energy, and at least one of them is higher than the excitation singlet energy and excitation triplet energy of the emitting material, respectively.

[0394] Precision transport layer:

[0395] The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers.

[0396] In some embodiments, the hole transport material has one of the characteristics of hole injection or transport and electron barrier. 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, pyrazolin derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silasein derivatives, aniline copolymers, and conductive polymer oligomers (particularly thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are given below.

[0397] [Chemical Formula 53]

[0398]

[0399] Electron transport layer:

[0400] The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers.

[0401] In some embodiments, the electron transport material only needs to have the function of transporting electrons injected from the cathode to the emissive layer. In some embodiments, the electron transport material also functions as a hole barrier material. Examples of electron transport layers that can be used in the present invention are not limited but include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide, fluoreneylidenemethane derivatives, anthraquinodimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are given below.

[0402] [Chemical Formula 54]

[0403]

[0404] In addition, examples of desirable compounds that can be added to each organic layer are provided. For instance, they may be added as stabilizing materials.

[0405] [Chemical Formula 55]

[0406]

[0407] Although specific examples of preferred materials that can be used in organic electroluminescent devices have been provided, the materials that can be used in the present invention are not limited to the following exemplary compounds. Furthermore, even if a compound is exemplified as a material having a specific function, it is possible to repurpose it as a material having other functions.

[0408] Device:

[0409] In some embodiments, the light-emitting layer is included in the device. For example, the device includes, but is not limited to, OLED valves, OLED lamps, displays for televisions, monitors for computers, mobile phones, and tablets.

[0410] In some embodiments, the electronic device comprises an OLED having at least one organic layer comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode.

[0411] In some embodiments, the composition described herein may be included in various photosensitive or photoactive devices, such as OLEDs or optoelectronic devices. In some embodiments, the composition may be useful for promoting charge transfer or energy transfer within the device and / or as a hole transport material. Examples of such devices include organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenching devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0412] Valve or lamp:

[0413] In some embodiments, the electronic device comprises an OLED comprising at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.

[0414] In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are neither red, green, nor blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors.

[0415] In some embodiments, the device is,

[0416] A circuit board having a first surface having a mounting surface and a second surface opposite thereto, and defining at least one opening, and

[0417] At least one OLED on the above-mentioned mounting surface, and at least one OLED having a light-emitting configuration in which the at least one OLED comprises a positive electrode, a negative electrode, and at least one organic layer including a light-emitting layer between the positive electrode and the negative electrode, and

[0418] Housing for a circuit board and,

[0419] It is an OLED light having at least one connector disposed at the end of the housing, wherein the housing and the connector define a package suitable for mounting to a lighting fixture.

[0420] In some embodiments, the OLED light has a plurality of OLEDs mounted on a circuit board so as to emit light in a plurality of directions. In some embodiments, some of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0421] Display or screen:

[0422] In some embodiments, the light-emitting layer of the present invention may be used in a screen or display. In some embodiments, the compound according to the present invention is deposited onto a substrate using a process such as vacuum evaporation, deposition, deposition, or chemical vapor deposition (CVD), though not limited thereto. In some embodiments, the substrate is a photoplate structure useful for two-sided etching that provides pixels with a unique aspect ratio. The screen (also called a mask) is used in the manufacturing process of an OLED display. By designing a corresponding artwork pattern, it is possible to arrange very steep and narrow tie bars between pixels in the vertical direction, and large, wide oblique openings in the horizontal direction. This enables the fine pattern configuration of pixels required for high-resolution displays while optimizing chemical vapor deposition onto the TFT backplane.

[0423] By internal patterning of the pixels, it becomes possible to construct three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Additionally, the use of an imaged "stripe" or halftone circle within the pixel area protects etching in a specific area until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas are processed at the same etching rate, but the depth varies depending on the halftone pattern. By changing the size and spacing of the halftone pattern, different etchings with varying protection rates within the pixel become possible, enabling localized deep etching necessary to form steep vertical angles.

[0424] A preferred material for a deposition mask is invar. Invar is a metal alloy that is cold-rolled into long, thin sheets at 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 region within a deposition mask is by wet chemical etching.

[0425] In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is processed using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is processed using wet chemical etching. In one further embodiment, the screen or display pattern is processed using plasma etching.

[0426] Method of manufacturing the device:

[0427] OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panel units. Typically, each cell panel on the mother panel is formed by forming a thin-film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT to sequentially form a pixel electrode, an emitting layer, a counter electrode, and an encapsulation layer over time, and then cutting from the mother panel.

[0428] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, and said method,

[0429] A process of forming a barrier layer on a base substrate of a mother panel, and

[0430] A process of forming a plurality of display units in cell panel units on the above barrier layer, and

[0431] A process of forming an encapsulation layer on each of the display units of the cell panel above, and

[0432] The method includes a process of applying an organic film to the interface portion between the cell panels.

[0433] In some embodiments, the barrier layer is an inorganic film formed, for example, of SiNx, and the ends of the barrier layer are covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists in smoothly cutting the mother panel into cell panel units.

[0434] In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may have a thin-film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface portion is formed from the same material as the material of the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, a planarization film between them, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the above manufacturing method, the organic film is not connected to either the display unit or the encapsulation layer.

[0435] Each of the above organic film and planarization film may include either polyimide or acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may also include a process of mounting a carrier substrate formed of a glass material on another surface of the base substrate before forming a barrier layer on one surface of the base substrate formed of polyimide, and a process of separating the carrier substrate from the base substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display.

[0436] In some embodiments, the passivation layer is an organic film disposed on the TFT layer for coating the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylic, just like the organic film formed at the end of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed at the end of the barrier layer, so that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film surrounds the end of the barrier layer and contacts the barrier layer.

[0437] 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 / drain electrode of the TFT layer.

[0438] In some embodiments, when a voltage is applied to a pixel electrode through a TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, thereby causing the organic light-emitting layer to emit light and thereby form an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.

[0439] In some embodiments, the encapsulation layer covering the display unit to prevent the penetration of external moisture may be formed as 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 applied to the interface portion is arranged with a gap between each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film is in direct contact with the base substrate, while the remaining portion of the organic film surrounds the end of the barrier layer and contacts the barrier layer.

[0440] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide. In several embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.

[0441] In some embodiments, the barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming a groove in the interface portion between the barrier layers of the cell panels. Each cell panel can be cut along the groove.

[0442] In some embodiments, the above manufacturing method further includes a process of cutting along the interface portion, wherein a groove is formed in the barrier layer, and at least a portion of the organic film is formed in the groove so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer which is an inorganic film and a flattening film which is an organic film are disposed on the TFT layer to cover the TFT layer. For example, a flattening film made of polyimide or acrylic is formed, and at the same time, the groove of the interface portion is covered with an organic film made of polyimide or acrylic. This prevents cracking by absorbing the impact generated when each cell panel is cut along the groove at the interface portion into the organic film. That is, if all barrier layers are completely exposed without an organic film, the impact generated when each cell panel is cut along the groove at the interface portion is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the grooves of the interface portion between the barrier layers are covered with an organic film, and each cell panel may be softly cut to absorb the shock that would otherwise be transmitted to the barrier layer without the organic film, thereby preventing cracks from forming in the barrier layer. In one embodiment, the organic film covering the grooves of the interface portion and the flattening film are spaced apart from each other. For example, if the organic film and the flattening film are connected to each other as a single layer, there is a risk that external moisture may enter the display unit through the remaining portions of the flattening film and the organic film; therefore, the organic film and the flattening film are spaced apart from each other, such as the organic film being spaced apart from the display unit.

[0443] In some embodiments, the display unit is formed by the formation of a light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, when a laser beam is emitted onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in the coefficients of thermal expansion between the carrier substrate and the base substrate.

[0444] In some embodiments, the mother panel is cut into cell panel units. In some embodiments, the mother panel is cut along the interface between cell panels using a cutter. In some embodiments, the groove of the interface along which the mother panel is cut is covered with an organic film, so the organic film absorbs shock during cutting. In some embodiments, cracking in the barrier layer can be prevented during cutting.

[0445] In some embodiments, the above method reduces the defect rate of the product and stabilizes its quality.

[0446] Another aspect is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the end of the barrier layer.

[0447] Examples

[0448] Synthesis examples and embodiments of the compound of general formula (1) are described in detail below. The materials, processing details, processing procedures, etc. shown below may be appropriately modified as long as they do not deviate from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below. In addition, the evaluation of luminescence characteristics was performed using a source meter (Keithly, 2400 series), a semiconductor parameter analyzer (Agilent Technologies, E5273A), an optical power meter measuring device (Newport, 1930C), an optical spectrometer (Ocean Optics, USB2000), a spectroradiometer (Topcon, SR-3), and a streak camera (Hamamatsu Photonics, C4334 type).

[0449] The synthesis procedure for compounds A and B included in general formula (1) is shown below. During the synthesis of compounds A and B, intermediates a to h were synthesized.

[0450] (Synthesization Example 1) Synthesis of Compound A

[0451] [Chemical Formula 56]

[0452]

[0453] Intermediate b

[0454] Starting compound a (2.0 g, 7.77 mmol), 4-chlorophenylboronic acid (1.2 g, 7.84 mmol), tetrakis(triphenylphosphine)palladium (0) (0.448 g, 0.388 mmol), sodium carbonate (2.46 g, 23.3 mmol), tetrahydrofuran (THF, 78 mL), and water (39 mL) were added under a nitrogen stream and stirred at 80°C for 4 hours. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain intermediate b (2.08 g, 6.24 mmol, yield 81%), which is a pale yellow solid.

[0455] intermediate c

[0456] Intermediate b (2.41 g, 7.23 mmol), 4-cyanophenylboronic acid (1.06 g, 7.23 mmol), tetrakis(triphenylphosphine)palladium (0) (0.417 g, 0.361 mmol), sodium carbonate (2.28 g, 21.6 mmol), THF (72 mL), and water (36 mL) were added under a nitrogen stream and stirred overnight at 80°C. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain intermediate c (2.70 g, 6.75 mmol, yield 93%), which is a white solid.

[0457] [Chemical Formula 57]

[0458]

[0459] Intermediate e

[0460] Intermediate c (1.0 g, 2.51 mmol), reaction compound d (0.831 g, 2.76 mmol), palladium(II) acetate (0.056 g, 0.251 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.145 g, 0.502 mmol), potassium carbonate (0.693 g, 5.02 mmol), and toluene (125 mL) were added under a nitrogen stream and stirred overnight at 120°C. The reaction solution was returned to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain intermediate e (1.06 g, 1.59 mmol, yield 64%), which is a light green solid.

[0461] Compound A

[0462] Intermediate e (1.06 g, 1.59 mmol), sodium hydride (0.049 g, 2.06 mmol), and N,N-dimethylformamide (DMF, 15 mL) were added under a nitrogen stream and stirred at 150°C for 3 hours. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain orange solid compound A (0.86 g, 1.33 mmol, yield 84%).

[0463] 1 H NMR (400MHz, CDCl3, δ): 8.88-8.98(2H), 8.71-8.79(1H), 8.61-8.71(2H), 8.28-8.38(1H), 7.96-8.09(2H), 7.83-7.91(2H), 7.65-7.81(6H), 7.23-7.25(1H), 6.77-6.94(3H), 6.24-6.31(1H), 5.90-5.97(1H)

[0464] ASAP MS Spectrum Analysis: C 42 H 22 N6S: Theoretical value 642.16, Observed value 643.23

[0465] (Synthesization Example 2) Synthesis of Compound B

[0466] [Chemical Formula 58]

[0467]

[0468] Intermediate f

[0469] Intermediate b (2.0 g, 6.00 mmol) synthesized in Synthesis Example 1, phenylboronic acid (0.738 g, 6.06 mmol), tetrakis(triphenylphosphine)palladium (0) (0.346 g, 0.300 mmol), sodium carbonate (1.90 g, 18.0 mmol), THF (60 mL), and water (30 mL) were added under a nitrogen stream and stirred overnight at 80°C. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The obtained solid was purified by silica gel column chromatography to obtain a white solid intermediate f (2.13 g, 5.68 mmol, yield 95%).

[0470] intermediate h

[0471] Intermediate f (1.0 g, 2.68 mmol), reaction compound g (0.812 g, 2.94 mmol), palladium(II) acetate (0.060 g, 0.268 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.155 g, 0.536 mmol), potassium carbonate (0.740 g, 5.36 mmol), and toluene (134 mL) were added under a nitrogen stream and stirred at 120°C for 3 days. The reaction solution was returned to room temperature and filtered, and the filtrate was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain intermediate h (0.98 g, 1.59 mmol, yield 60%), which is a pale yellow solid.

[0472] [Chemical Formula 59]

[0473]

[0474] Compound B

[0475] Intermediate h (0.98 g, 1.59 mmol), sodium hydride (0.049 g, 2.06 mmol), and DMF (30 mL) were added under a nitrogen stream and stirred at 150°C for 3 hours. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain orange solid compound B (0.37 g, 0.62 mmol, yield 39%).

[0476] 1 H NMR (400 MHz, CDCl3, δ): 8.74-8.85 (3H), 8.65-8.71 (2H), 7.96-8.07 (3H), 7.63-7.78 (5H), 7.48-7.63 (4H), 7.29-7.35 (1H), 7.20-7.25(1H), 6.68-6.89(3H), 6.19-6.26(1H), 5.81-5.87(1H)

[0477] ASAP MS Spectrum Analysis: C 40 H 24 N4S: Theoretical value 592.17, Observed value 593.08

[0478] (Synthesization Example 3) Synthesis of Compound C

[0479] [Chemical Formula 60]

[0480]

[0481] Intermediate j

[0482] Starting material i (1.50 g, 5.18 mmol), 4-chlorophenylboronic acid (0.809 g, 5.18 mmol), tetrakis(triphenylphosphine)palladium (0) (0.299 g, 0.259 mmol), sodium carbonate (1.09 g, 10.3 mmol), THF (52 mL), and water (26 mL) were added under a nitrogen stream and stirred overnight at 80°C. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain a pale yellow solid intermediate j (1.08 g, 2.93 mmol, yield 57%).

[0483] Intermediate k

[0484] Intermediate j (1.08 g, 2.93 mmol), 4-cyanophenylboronic acid (0.430 g, 2.93 mmol), tetrakis(triphenylphosphine)palladium (0) (0.168 g, 0.146 mmol), sodium carbonate (0.931 g, 8.79 mmol), THF (29 mL), and water (15 mL) were added under a nitrogen stream and stirred overnight at 80°C. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain intermediate k (1.27 g, 2.92 mmol, yield 100%), which is a white solid.

[0485] [Chemical Formula 61]

[0486]

[0487] Intermediate l

[0488] Intermediate k (1.27 g, 2.93 mmol), compound d (1.94 g, 6.44 mmol), palladium(II) acetate (0.066 g, 0.293 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.170 g, 0.586 mmol), potassium carbonate (0.809 g, 5.86 mmol), and toluene (146 mL) were added under a nitrogen stream and stirred overnight at 120°C. The reaction solution was returned to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain intermediate l (1.76 g, 1.82 mmol, yield 63%), which is a yellow solid.

[0489] Compound C

[0490] Intermediate l (1.76 g, 1.59 mmol), sodium hydride (0.109 g, 4.55 mmol), and DMF (36 mL) were added under a nitrogen stream and stirred overnight at 150°C. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain orange solid compound C (0.64 g, 0.694 mmol, yield 38%).

[0491] 1 H NMR (400MHz, CDCl3, δ): 8.91-8.98(3H), 8.50-8.57(2H), 8.33-8.37(1H), 8.29-8.33(1H), 8.05-8.11(1H), 7.95-8.04(2H), 7.87-7.94(3H), 7.70-7.80(3H), 7.58-7.67(3H), 7.28-7.32(1H), 7.19-7.23(1H), 6.90-6.98(1H), 6.68-6.88(5H), 6.15-6.21(1H), 6.08-6.14(1H), 5.81-5.87(1H), 5.72-5.78(1H)

[0492] ASAP MS Spectrum Analysis: C 61 H 31 N9S: Theoretical value 921.24, Observed value 922.67

[0493] (Synthesization Example 4) Synthesis of Compound D

[0494] [Chemical Formula 62]

[0495]

[0496] Intermediate n

[0497] Starting material m (1.00 g, 2.92 mmol), compound d (0.967 g, 3.21 mmol), palladium(II) acetate (0.066 g, 0.292 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.169 g, 0.584 mmol), potassium carbonate (0.807 g, 5.84 mmol), and toluene (100 mL) were added under a nitrogen stream and stirred overnight at 120°C. The reaction solution was returned to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain an intermediate n (1.47 g, 2.42 mmol, yield 83%), which is a pale yellow solid.

[0498] Compound D

[0499] Intermediate n (1.47 g, 2.42 mmol), sodium hydride (0.125 g, 3.14 mmol), and DMF (24 mL) were added under a nitrogen stream and stirred at 150°C for 3 hours. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The resulting solid was purified by silica gel column chromatography to obtain yellow solid compound D (0.79 g, 1.34 mmol, yield 56%).

[0500] 1 H NMR (400MHz, CDCl3, δ): 8.83-8.91(2H), 8.17-8.28(4H), 7.99-8.07(2H), 7.90-7.95(1H), 7.83-7.89(2H), 7.64-7.78(4H), 7.55-7.63(1H), 7.35-7.43(1H), 7.27-7.31(1H), 6.96-7.02(1H), 6.77-6.85(1H), 6.13-6.19(1H), 5.83-5.88(1H)

[0501] ASAP MS Spectrum Analysis: C 40 H 22 N6: Theoretical value 586.19, Observed value 587.26

[0502] (Reference Synthesis Example)

[0503] The following Comparative Compound 1 and Comparative Compound 2 were synthesized by changing a portion of the compounds used in the procedure described in Synthesis Example 1 and Synthesis Example 2.

[0504] [Chemical Formula 63]

[0505]

[0506] Comparative Compound 1 Comparative Compound 2

[0507] (Example 1) Fabrication and Evaluation of Thin Films

[0508] By vacuum deposition on a quartz substrate, vacuum degree 1×10 -3 Compound A was deposited under conditions of less than Pa, and a knit thin film composed of Compound A was formed to a thickness of 100 nm. Separately, on a quartz substrate, by vacuum deposition at a vacuum degree of 1×10⁻⁶ -3 Compound A and H1 were deposited from different deposition sources under conditions of less than Pa, and a dope thin film with a concentration of compound A of 35 wt% was formed to a thickness of 100 nm.

[0509] Instead of compound A, compound B, comparative compound 1, and comparative compound 2 were used, respectively, to form knit thin films and dope thin films in the same manner.

[0510] The energies of HOMO and LUMO were measured using each formed knit thin film. The measurement results are shown in Table 4. When 300 nm excitation light was irradiated onto each formed dope thin film, delayed fluorescence was observed. When the delayed fluorescence lifetime (τ2) was measured, Compound A was about 54 μ seconds shorter than Comparative Compound 1, and Compound B was about 261 μ seconds shorter than Comparative Compound 2. In addition, the orientation degree (S value) of Compound A, Compound B, Comparative Compound 1, and Comparative Compound 2 was determined using each formed dope thin film by the method described in Scientific Reports 2017, 7, 8405. As a result, it was confirmed that Compound A had an S value about 0.71 lower than Comparative Compound 1, Compound B had an S value about 0.48 lower than Comparative Compound 2, and the compound represented by general formula (1) was closer to -0.5. An S value of -0.5 indicates the state of being most horizontally oriented. These results indicate that the compound represented by general formula (1) has a short delayed fluorescence lifetime and high orientation within the emitting layer.

[0511] (Example 2) Fabrication and Evaluation of Organic Electroluminescence Device

[0512] On a glass substrate on which an anode consisting of indium tin oxide (ITO) with a film thickness of 100 nm is formed, each thin film is deposited by vacuum deposition at a vacuum degree of 1×10 -6Pa was stacked. First, HATCN was formed on ITO with a thickness of 10 nm, and NPD was formed on top of it with a thickness of 30 nm. Subsequently, TrisPCz was formed on top of it with a thickness of 10 nm, and PTCz was formed on top of it with a thickness of 5 nm. Next, H1 and compound A were co-deposited from different deposition sources to form a emitting layer with a thickness of 40 nm. At this time, the concentration of the compound represented by general formula (1) was set to 35 wt%. On top of that, SF3TRZ was formed with a thickness of 10 nm, and additionally, SF3TRZ and Liq were co-deposited from different deposition sources to form a layer with a thickness of 30 nm. At this time, the SF3TRZ:Liq (weight ratio) was set to 7:3. Additionally, Liq was formed with a thickness of 2 nm, and then aluminum (Al) was deposited with a thickness of 100 nm to form a cathode. Following the above procedure, the organic electroluminescence device of Example 2 was fabricated.

[0513] An organic electroluminescent device was formed by using Compound B, Comparative Compound 1, and Comparative Compound 2, respectively, instead of Compound A.

[0514] As a result of energizing each fabricated organic electroluminescent device, it was confirmed that all devices operated at a low voltage of 4.3V or less. In addition, each organic electroluminescent device at 50mA / cm 2 As a result of continuously emitting light and measuring the time (LT95) until the light intensity decreased to 95% of the level at the start of operation, the results shown in Table 4 were obtained.

[0515] (Example 3) Fabrication and Evaluation of Organic Electroluminescence Device

[0516] An organic electroluminescence device of Example 3 was fabricated by the same procedure as in Example 2, except that the light-emitting layer of Example 2 was formed by co-depositing H1, compound A, and F38 from different deposition sources to form a light-emitting layer with a thickness of 30 nm. In the light-emitting layer of Example 3, the concentration of H1 was 64.5 wt%, the concentration of compound A was 35 wt%, and the concentration of F38 was 0.5 wt%.

[0517] An organic electroluminescent device was formed by using Compound B, Comparative Compound 1, and Comparative Compound 2, respectively, instead of Compound A.

[0518] As a result of energizing each fabricated organic electroluminescent device, it was confirmed that all devices operated at a low voltage of 4.3V or less. In addition, each organic electroluminescent device at 50mA / cm 2 As a result of continuously emitting light and measuring the time (LT95) until the light intensity decreased to 95% of the level at the start of operation, the results shown in Table 4 were obtained.

[0519] [Table 4]

[0520]

[0521] Compared to devices using Comparative Compound 1 or Comparative Compound 2, devices using Compound A and Compound B have an LT95 of more than four times longer. In this regard, it was confirmed that by using the compound represented by General Formula (1), the lifespan of the device can be significantly extended while maintaining a low driving voltage of the device.

[0522] [Chemical Formula 64]

[0523]

[0524]

[0525] Industrial applicability

[0526] By using a compound represented by general formula (1), an organic electroluminescent device with good characteristics can be provided. Therefore, the present invention has high industrial applicability.

Claims

Claim 1 Compounds represented by the following general formula (1). General formula (1) [Chemical formula 1] [In general formula (1), X 1 is N or CR 11 Represents, and X 2 is N or CR 12 Represents, X 3 is N or CR 13 Represents, and X 4 is N or CR 14 It represents. R 1 ~R 7 and R 11 ~R 14 represents, respectively, a hydrogen atom, a deuterium atom, or a substituent. R 8 It represents silver, a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar and R 1 , R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 Ar and Ar and A never combine to form a cyclic structure. Ar represents a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. A represents a cyclic structure. Claim 2 A compound according to claim 1, wherein Ar is a substituted or unsubstituted arylene group. Claim 3 A compound according to claim 2, wherein Ar is a substituted or unsubstituted phenylene group. Claim 4 In claim 1, R 8 A compound in which this is a substituted or unsubstituted aryl group. Claim 5 A compound according to claim 1, wherein A has a benzothieno structure, a benzofuro structure, an indolo structure, a benzo structure, a naphtho structure, or a phenantro structure. Claim 6 A compound of claim 1, wherein A is a cyclic structure that may be substituted with one or more atoms selected from the group consisting of deuterium atoms and general formula (2'). General formula (2') [Chemical formula 2] [In general formula (2'), X 1 ' is N or CR 11 Represents ', X 2 ' is N or CR 12 Representing ', X 3 ' is N or CR 13 Represents ', X 4 ' is N or CR 14 Represents '. R 1 '~R 7 Each represents a hydrogen atom, a deuterium atom, or a cyano group independently. * indicates a bonding position.] Claim 7 In claim 1, X 1 This CR 11 and X 2 Ga CR 12 is, X 3 This CR 13 and X 4 Ga CR 14 Phosphorus, compound. Claim 8 In claim 7, R 11 ~R 14 A compound in which at least one of the groups is a cyano group or an aryl group that may be substituted with a deuterium atom. Claim 9 In claim 7, R 11 ~R 14 A compound in which each is independently a hydrogen atom or a deuterium atom. Claim 10 In claim 1, Ar is a substituted or unsubstituted arylene group, and R 8 A compound in which this is a substituted or unsubstituted aryl group and A has a benzothieno structure. Claim 11 In claim 10, X 1 This CR 11 and X 2 Ga CR 12 is, X 3 This CR 13 and X 4 Ga CR 14 Phosphorus, compound. Claim 12 A luminescent material comprising a compound described in any one of claims 1 to 11. Claim 13 A delayed fluorescence material comprising a compound described in any one of claims 1 to 11. Claim 14 An organic electroluminescent device comprising a compound described in any one of claims 1 to 11. Claim 15 An organic electroluminescence device according to claim 14, wherein the organic electroluminescence device has a layer containing the compound, and the layer also contains a host material. Claim 16 An organic electroluminescence device according to claim 14, wherein the organic electroluminescence device has a layer containing the compound, and the layer also includes a light-emitting material having a structure outside the range of the general formula (1). Claim 17 An organic electroluminescence device according to claim 16, wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

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