Composition for organic optoelectric element, organic optoelectric element, and display device

Abstract

The present invention relates to a composition for an organic optoelectronic element, and an organic optoelectronic element and a display device including the same, the composition comprising a first compound, a second compound, and a third compound, wherein the first compound is represented by Chemical Formula I, the second compound is represented by Chemical Formula II, and the third compound is represented by Chemical Formula IIIA or Chemical Formula IIIB. Details of Chemical Formula I, Chemical Formula II, Chemical Formula IIIA, and Chemical Formula IIIB are the same as described in the specification.

Description

Technical Field

[0001] This invention discloses a composition for organic optoelectronic elements, an organic optoelectronic element, and a display device. Background Technology

[0002] Organic photoelectric elements (organic photodiodes) are devices that can convert electrical energy and light energy into each other.

[0003] Organic optoelectronic devices can be classified according to their driving principle as follows. One type is a photoelectronic device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other type is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to the electrodes.

[0004] Examples of organic optoelectronic components include organic optoelectronic components, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0005] Organic light-emitting diodes (OLEDs) have recently attracted attention due to the increasing demand for flat panel displays. OLEDs are devices that convert electrical energy into light, and their performance is greatly influenced by the organic materials between the electrodes. Summary of the Invention

[0006] [Technical Issues]

[0007] One embodiment provides a composition for organic optoelectronic devices that enables high efficiency and long lifespan.

[0008] Another embodiment provides an organic optoelectronic element comprising a composition for organic optoelectronic elements.

[0009] Another embodiment provides a display device including organic optoelectronic elements.

[0010] [Technical Solution]

[0011] According to one embodiment, the composition for an organic optoelectronic element comprises a first compound, a second compound, and a third compound, wherein the first compound is represented by chemical formula I, the second compound by chemical formula II, and the third compound by chemical formula IIIA or chemical formula IIIB.

[0012] [Chemical Formula I]

[0013]

[0014] In chemical formula I,

[0015] Z 1 To Z 3 Is it N or CL? a-R a ,

[0016] Z 1 To Z 3 At least two of them are N.

[0017] L a and L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0018] R 1 and R 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0019] R a R 3 and R 4 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0020] Ring A is represented by chemical formulas I-1 to I-7:

[0021]

[0022] Among them, in chemical formulas I-1 to I-7,

[0023] X 1 Is it O, S, or NR? b ,

[0024] R b and R 5 To R 12 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0025] * indicates a connection point;

[0026] [Chemical Formula II]

[0027]

[0028] In chemical formula II,

[0029] L 4It is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0030] Ar 1 It is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a combination thereof.

[0031] R 13 and R 14 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0032] Ring B can be represented by any one of the chemical formulas II-1 to II-4:

[0033]

[0034]

[0035] Among them, in chemical formulas II-1 to II-4,

[0036] L 5 and L 6 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0037] L 8 It is a single bond, or a substituted or unsubstituted C6 to C20 arylene.

[0038] Ar 2 and Ar 3 It is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a combination thereof.

[0039] R 15 To R 21 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0040] * indicates a connection point;

[0041] [Chemical Formula IIIA]

[0042]

[0043] [Chemical Formula IIIB]

[0044]

[0045] Among them, in chemical formula IIIA and chemical formula IIIB,

[0046] L 7 and L 8 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, and

[0047] R 22 To R 41 Each of these elements independently is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof.

[0048] According to another embodiment, the organic optoelectronic element includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer contains a composition for the organic optoelectronic element.

[0049] According to another embodiment, a display device including organic optoelectronic elements is provided.

[0050] [Beneficial Effects]

[0051] It can realize organic optoelectronic components with high efficiency and long life. Attached Figure Description

[0052] Figure 1 and Figure 2 Each of these shows a cross-sectional view of an organic light-emitting diode according to an embodiment.

[0053] <Explanation of Figure Markers>

[0054] 100, 200: Organic Light Emitting Diodes

[0055] 105: Organic layer

[0056] 110: Cathode

[0057] 120: Anode

[0058] 130: Emissive layer

[0059] 140: Hole auxiliary layer Detailed Implementation

[0060] Embodiments of the invention are described in detail below. However, these embodiments are exemplary, and the invention is not limited thereto; rather, the invention is defined by the scope of the claims.

[0061] In this specification, unless otherwise defined, “substitution” means that at least one hydrogen atom of a substituent or compound is replaced by a deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or combinations thereof.

[0062] In one embodiment of the invention, "substitution" means that at least one hydrogen atom in the substituent or compound is replaced by deuterium, cyano, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylamino, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. Furthermore, in a specific embodiment of the invention, "substitution" means that at least one hydrogen atom in the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 arylamino, C6 to C30 aryl, or C2 to C30 heteroaryl. Furthermore, in a specific embodiment of the invention, "substitution" means that at least one hydrogen atom in the substituent or compound is replaced by deuterium, cyano, C1 to C5 alkyl, C6 to C20 arylamino, C6 to C18 aryl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, or pyridyl. Furthermore, in specific examples of the present invention, "substitution" means that at least one hydrogen atom in the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, C6 to C20 aromatic amino, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, fluorenyl, dibenzofuranyl, dibenzothiophene, carbazoyl or pyridyl.

[0063] In this specification, unless otherwise defined, "heterogeneous" means a functional group containing one to three heteroatoms selected from N, O, S, P and Si, with the remainder being carbon.

[0064] In this specification, "aryl" means a group comprising at least one aromatic hydrocarbon moiety, and may include groups in which all elements of the aromatic hydrocarbon moiety have conjugated p-orbitals, such as phenyl, naphthyl, etc.; groups in which two or more aromatic hydrocarbon moiety portions can be linked by σ bonds, such as biphenyl, terphenyl, tetraphenyl, etc.; and groups in which two or more aromatic hydrocarbon moiety portions are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene, etc.

[0065] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0066] In this specification, "heterocyclic group" is a superordinate concept of a heteroaryl group and may include at least one heteroatom selected from N, O, S, P, and Si instead of carbon (C) in a cyclic compound, such as aryl, cycloalkyl, their fused rings, or combinations thereof. When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0067] For example, "heteroaryl" refers to an aryl group that includes at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by σ bonds, or when a heteroaryl group includes two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring can contain 1 to 3 heteroatoms.

[0068] More specifically, the substituted or unsubstituted C6 to C30 aryl group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted trefene, a substituted or unsubstituted triphenyl, a substituted or unsubstituted perylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is not limited thereto.

[0069] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted pyrroleyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, or a substituted or unsubstituted benzeneyl group. The following are not limited to: benzothioyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or combinations thereof.

[0070] In this specification, hole characteristics refer to the ability of holes that contribute electrons when an electric field is applied and that are formed in the anode due to the conductivity of the highest occupied molecular orbital (HOMO) energy level to be readily injected into and transported in the light-emitting layer.

[0071] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and the ability of electrons formed in the cathode due to the conductivity characteristics based on the lowest unoccupied molecular orbital (LUMO) energy level to be easily injected into and transported in the light-emitting layer.

[0072] The following describes a composition for an organic optoelectronic device according to one embodiment.

[0073] According to one embodiment, the composition for an organic optoelectronic device is a mixture comprising three types of compounds (specifically, a first compound having electronic properties, a second compound having hole properties, and a third compound having buffering properties).

[0074] The third compound is a compound with a wide HOMO-LUMO bandgap, which includes both the HOMO-LUMO bandgap of the first and second compounds, and has a lower hole mobility than the second compound with hole properties. This slows down the hole injection properties and can reduce hole trapping.

[0075] Furthermore, since the third compound has a lower electron mobility than the first compound, and the luminescent layer region moves relatively toward the hole transport auxiliary layer, exciton quenching and the resulting degradation at the interface with the electron transport auxiliary layer can be reduced, thus increasing the lifetime.

[0076] The first compound having the above electronic characteristics has a structure in which carbazole or carbazole derivatives are substituted with a nitrogen-containing six-membered ring, and is represented by chemical formula I.

[0077] [Chemical Formula I]

[0078]

[0079] In chemical formula I,

[0080] Z 1 To Z 3 Is it N or CL? a -R a ,

[0081] Z 1 To Z 3 At least two of them are N.

[0082] L a and L1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0083] R 1 and R 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0084] R a R 3 and R 4 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0085] Ring A is represented by chemical formulas I-1 to I-7:

[0086]

[0087] Among them, in chemical formulas I-1 to I-7,

[0088] X 1 Is it O, S, or NR? b ,

[0089] R b and R 5 To R 12 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0090] * indicates a connection point.

[0091] Specifically, in chemical formula I, Z 1 To Z 3 Each is independently N or CH, Z 1 To Z 3 At least two of them are N.

[0092] For example, Z 1 To Z 3 Each can be N.

[0093] For example, Z 1 and Z 3 It can be N, and Z 2 It can be CH.

[0094] For example, in chemical formula I, L 1 To L 3 Each of these can be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted pyridylene.

[0095] As a specific example, in chemical formula I, L 1 To L 3 Each can be a single bond, phenylene, biphenylene, carbazolyl, dibenzofuran, dibenzothiophene, or pyridylene independently.

[0096] For example, in chemical formula I, L 1 To L 3 Each can be a single bond, a meta-phenylene, or a para-phenylene independently.

[0097] For example, in chemical formula I, R 1 and R 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fused carbazolyl, substituted or unsubstituted fused dibenzofuranyl, substituted or unsubstituted fused dibenzothiophenyl, substituted or unsubstituted fused indolocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinel, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted benzoquinazolinyl.

[0098] As a specific example, in chemical formula I, R 1 and R 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolecarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0099] For example, in chemical formula I, R 1 and R 2Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0100] Depending on the specific structure of carbazole and its derivatives, chemical formula I can be represented by any of the following: chemical formulas, for example, chemical formula IA to chemical formula IJ.

[0101]

[0102]

[0103] In chemical formulas IA to IJ, Z 1 To Z 3 L 1 To L 3 R 1 To R 12 and X 1 The definition is the same as above.

[0104] Specifically, in chemical formula IA, R 3 To R 6 Each of these can be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolecarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenel.

[0105] For example, in chemical formula IA, R 3 To R 6 Each of them can be hydrogen, phenyl, biphenyl, carbazolyl, dibenzofuranyl, or dibenzothiophene.

[0106] Specifically, in chemical formulas IB to ID, R 3 R 4 and R 7 To R 9 Each of these can be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolecarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenel.

[0107] For example, in chemical formulas IB to ID, R 3 R 4 and R 7 To R 9 It can be hydrogen or phenyl independently.

[0108] Specifically, in chemical formulas IE to IJ, R 3 R 4 and R 10 To R 12 Each of these can be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolecarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenel.

[0109] For example, in chemical formulas IE to IJ, R 3 R 4 and R 10 To R 12 Each can be either hydrogen or phenyl. For example, chemical formula IA can be represented by any one of chemical formulas IA-1 to IA-7.

[0110]

[0111] [Chemical Formula IA-7]

[0112]

[0113] In chemical formulas IA-1 to IA-7, Z 1 To Z 3 L 1 To L 3 R 1 and R 2 The definition is the same as above, and R 3 To R 5 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0114] For example, chemical formula IB can be represented by chemical formula IB-1 or chemical formula IB-2.

[0115]

[0116] In chemical formulas IB-1 and IB-2, Z 1 To Z 3 L 1 To L 3 R 1 and R 2 The definition is the same as above, and R 8 It can be a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0117] For example, chemical formula IC can be represented by chemical formula IC-1 or chemical formula IC-2.

[0118]

[0119] In chemical formulas IC-1 and IC-2, Z 1 To Z 3 L 1 To L 3 R 1 and R 2 The definition is the same as above, and R 8 It can be a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0120] For example, chemical formula ID can be represented by chemical formula ID-1.

[0121] [Chemical Formula IDE-1]

[0122]

[0123] In chemical formula ID-1, Z 1 To Z 3 L 1 To L 3 R 1 and R 2 The definition is the same as above.

[0124] For example, chemical formula IE can be represented by any one of chemical formulas IE-1 to IE-5.

[0125]

[0126] [Chemical Formula ⅠE-5]

[0127]

[0128] In chemical formulas IE-1 to IE-5, Z 1 To Z 3 L 1 To L 3 R 1 R 2 and X 1 The definition is the same as above, and R 3 To R 11 It can be a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0129] For example, chemical formula IF can be represented by either chemical formula IF-1 or chemical formula IF-2.

[0130]

[0131] In chemical formulas IF-1 and IF-2, Z 1 To Z 3 L 1 To L 3 R 1 R 2 and X 1 The definition is the same as above, and R 3 It can be a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0132] For example, chemical formula IG can be represented by either chemical formula IG-1 or chemical formula IG-2.

[0133]

[0134] In chemical formulas IG-1 and IG-2, Z 1 To Z 3 L 1 To L 3 R 1 R 2 and X 1 The definition is the same as above, and R 3 It can be a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0135] For example, the chemical formula ⅠH can be represented by the chemical formula ⅠH-1.

[0136] [Chemical formula IH-1]

[0137]

[0138] In chemical formula ⅠH⁻¹, Z 1 To Z 3 L 1 To L 3 R 1 R 2 and X 1 The definition is the same as above.

[0139] For example, chemical formula Ⅰ can be represented by either chemical formula ⅠI-1 or chemical formula ⅠI-2.

[0140]

[0141] In chemical formulas II-1 and II-2, Z 1 To Z 3 L 1 To L 3 R 1R 2 and X 1 The definition is the same as above, and R 3 It can be a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0142] The second compound with cavitation properties has a structure in which the carbazole or carbazole derivative is substituted or unsubstituted with a C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group, and is represented by chemical formula II.

[0143] [Chemical Formula II]

[0144]

[0145] In chemical formula II,

[0146] L 4 It is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0147] Ar 1 It is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a combination thereof.

[0148] R 13 and R 14 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0149] Ring B can be represented by any one of the chemical formulas II-1 to II-4:

[0150]

[0151] Among them, in chemical formulas II-1 to II-4,

[0152] L 5 and L 6 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0153] L 8 It is a single bond, or a substituted or unsubstituted C6 to C20 arylene.

[0154] Ar 2 and Ar 3It is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a combination thereof.

[0155] R 15 To R 21 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0156] * indicates a connection point.

[0157] Specifically, in chemical formula II, L 4 It can be a single bond or a C6 to C12 arylene group.

[0158] For example, in chemical formula II, L 4 It can be a single bond or a substituted or unsubstituted phenyl group.

[0159] In chemical formula II, Ar 1 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0160] For example, in chemical formula II, Ar 1 It can be a substituted or unsubstituted meta-biphenyl or a substituted or unsubstituted para-biphenyl.

[0161] Depending on the specific structure of carbazole and its derivatives, chemical formula II can be represented by any of the following: chemical formulas, for example, IIA to IIF.

[0162] [Chemical Formula IIA]

[0163]

[0164] [Chemical Formula IIB]

[0165]

[0166] [Chemical Formula IIC]

[0167]

[0168] [Chemical Formula IID]

[0169]

[0170] [Chemical Formula IIE]

[0171]

[0172] [Chemical Formula IIF]

[0173]

[0174] In chemical formulas IIA to IIF, L 4 To L 6 L 8 Ar 1 To Ar 3 and R 13 To R 21 The definition is the same as above.

[0175] Specifically, in chemical formula IIA, R 13 To R 18 Each can be hydrogen, substituted or unsubstituted phenyl, or substituted or unsubstituted carbazolyl, independently.

[0176] For example, in chemical formula IIA, R 13 To R 18 Each can be hydrogen or a substituted or unsubstituted phenyl group, and each can be independent of the other.

[0177] Specifically, in chemical formula IIA, L 5 It can be a single bond or a substituted or unsubstituted C6 to C12 aryl group.

[0178] For example, in chemical formula IIA, L 5 It can be a single bond or a substituted or unsubstituted phenylene.

[0179] Specifically, in chemical formula IIA, L 8 It can be a single bond or a substituted or unsubstituted C6 to C12 aryl group.

[0180] For example, in chemical formula IIA, L 8 It can be a single bond or a substituted or unsubstituted phenylene.

[0181] Specifically, in chemical formula IIA, Ar 2 It can be a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0182] For example, in chemical formula IIA, Ar 2 It can be a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0183] Specifically, in chemical formulas IIB to IIF, R13 R 14 and R 19 To R 21 Each can be hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted triphenylene, or substituted or unsubstituted carbazolyl, independently.

[0184] For example, in chemical formulas IIB to IIF, R 13 R 14 and R 19 To R 21 Each can be hydrogen or a substituted or unsubstituted phenyl group, and each can be independent of the other.

[0185] Specifically, in chemical formulas IIB to IIF, L 6 It can be a single bond or a substituted or unsubstituted phenylene.

[0186] For example, in chemical formulas IIB to IIF, L 6 It can be a single bond or a substituted or unsubstituted phenylene.

[0187] Specifically, in chemical formulas IIB to IIF, Ar 3 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0188] For example, IIB to chemical formula IIF, Ar 3 It can be a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0189] For example, chemical formula IIA can be represented by any one of chemical formulas IIA-1 to IIA-3.

[0190] [Chemical Formula IIA-1]

[0191]

[0192] [Chemical Formula IIA-2]

[0193]

[0194] [Chemical Formula IIA-3]

[0195]

[0196] In chemical formulas IIA-1 to IIA-3, L 4 L 5 Ar 1 Ar 2 and R13 To R 18 The definition is the same as above.

[0197] The third compound with buffering properties can be represented by chemical formula IIIA, in which benzo[a]phenanthrene is replaced by spirofluorene, or by chemical formula IIIB, in which benzo[a]phenanthrene is replaced by dibenzofuranyl (or dibenzothiophene).

[0198] [Chemical Formula IIIA]

[0199]

[0200] [Chemical Formula IIIB]

[0201]

[0202] In chemical formulas IIIA and IIIB,

[0203] L 7 and L 8 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof.

[0204] R 22 To R 41 Each of these elements independently comprises hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and

[0205] X 2 It is O or S.

[0206] According to a first embodiment of the present invention, the third compound may be represented by the chemical formula IIIA.

[0207] In the first embodiment, the first compound may be represented by chemical formula IA or chemical formula IE.

[0208] For example, the first compound according to the first embodiment can be represented by the chemical formula IA.

[0209] In the first embodiment, the second compound may be represented by chemical formula IIA or chemical formula IIF.

[0210] For example, the second compound according to the first embodiment may be represented by chemical formula IIA-1 or chemical formula IIA-2.

[0211] As a specific example, the second compound according to the first embodiment can be represented by any one of the chemical formulas IIA-1, IIA-2, and IIF.

[0212] For example, the third compound according to the first embodiment can be represented by any one of the chemical formulas IIIA-1 to IIIA-4.

[0213] [Chemical Formula IIIA-1]

[0214]

[0215] [Chemical Formula IIIA-2]

[0216]

[0217] [Chemical Formula IIIA-3]

[0218]

[0219] [Chemical Formula IIIA-4]

[0220]

[0221] In chemical formulas IIIA-1 to IIIA-4, L 7 and R 22 To R 33 The definition is the same as above.

[0222] As a specific example, the third compound according to the first embodiment can be represented by chemical formula IIIA-4, and in chemical formula IIIA-4, L 7 It can be a single bond or a substituted or unsubstituted phenylene, and R 22 To R 33 It can be hydrogen, substituted or unsubstituted phenyl, or substituted or unsubstituted carbazolyl.

[0223] According to the most specific first embodiment, the first compound may be represented by chemical formula IA-1 or chemical formula IA-4, the second compound may be represented by any one of chemical formula IIA-1, chemical formula IIA-2 and chemical formula IIF, and the third compound may be represented by chemical formula IIIA-4.

[0224] In chemical formulas IA-1 and IA-4, Z 1 To Z 3 L 1 To L 3 R 1 and R 2 The definition is the same as above, and R 3 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted indolocarbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenel.

[0225] In chemical formulas IIA-1, IIA-2, and IIF, L 4 and L 5 Each can be a single bond or a substituted or unsubstituted phenylene group, Ar 1 and Ar 2 Each can be independently a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl, and R 13 To R 18 Each can be either hydrogen or a substituted or unsubstituted phenyl group.

[0226] In the chemical formula ⅢBA-4, L 7 It can be m-phenylene or p-phenylene, and R 22 To R 33 Each can be hydrogen.

[0227] According to a second embodiment of the present invention, the third compound may be represented by the chemical formula IIIB.

[0228] In the second embodiment, the first compound may be represented by any of the aforementioned chemical formulas IA and ID to IJ.

[0229] For example, the first compound according to the second embodiment may be represented by chemical formula IA or chemical formula IE.

[0230] In the second embodiment, the second compound may be represented by the aforementioned chemical formula IIA or chemical formula IIF.

[0231] For example, the second compound according to the second embodiment can be represented by any one of the chemical formulas IIA-1 to IIA-3.

[0232] As a specific example, the second compound according to the second embodiment can be represented by any one of the chemical formulas IIA-1, IIA-2, and IIF.

[0233] In chemical formulas IIA-1, IIA-2, and IIF, R 13 To R 21 They can each be hydrogen, L 4 To L 6 Each can be a single bond or a substituted or unsubstituted phenylene, and Ar 1 To Ar 3 Each can be a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl, on its own.

[0234] For example, the third compound according to the second embodiment can be represented by chemical formulas IIIB-1 to IIIB-4.

[0235] [Chemical Formula IIIB-1]

[0236]

[0237] [Chemical Formula IIIB-2]

[0238]

[0239] [Chemical Formula IIIB-3]

[0240]

[0241] [Chemical Formula IIIB-4]

[0242]

[0243] In chemical formulas IIIB-1 to IIIB-4, X 2 L 8 and R 34 To R 41 The definition is the same as above.

[0244] As a specific example, the third compound according to the second embodiment may be represented by chemical formula IIIB-1 or chemical formula IIIB-4.

[0245] According to the second most specific embodiment, the first compound may be represented by chemical formula IA-1, the second compound may be represented by chemical formula IIA-1, and the third compound may be represented by chemical formula IIIA-4.

[0246] In chemical formula IA-1, Z 1 To Z 3 They can each be N, L 1 To L 3 Each can be a single bond or an unsubstituted phenylene, and R 1 and R 2 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0247] In chemical formula IIIA-1, R 13 To R 18 Each of these can be independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted dibenzothiophene, L 4 and L 5 Each can be independently a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl, and Ar1 and Ar 2 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0248] In chemical formula III-4, X 2 It can be O or S, R 22 To R 29 Each can be independently hydrogen or a substituted or unsubstituted phenyl group, and L 7 It can be selected from the linking group of group I.

[0249] Group I

[0250]

[0251] According to another most specific second embodiment, the first compound may be represented by chemical formula IE-1, the second compound may be represented by chemical formula IIA-1, and the third compound may be represented by chemical formula IIIA-1 or chemical formula IIIA-4.

[0252] In chemical formula IE-1, X 1 It can be NR b Or O, R b It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted terphenyl, Z 1 To Z 3 They can each be N, L 1 To L 3 Each can be a single bond, or a substituted or unsubstituted phenylene, and R 1 and R 2 Each can be an independently substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0253] In chemical formula IIIA-1, R 13 To R 18 Each of these can be independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted dibenzothiophene, L 4 and L 5 Each can be independently a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl, and Ar 1 and Ar 2Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0254] In chemical formulas III-1 and III-4, X 2 It can be O or S, R 22 To R 29 Each can be independently hydrogen or a substituted or unsubstituted phenyl group, and L 7 It can be selected from the linking group of group I.

[0255] On the other hand, the above-mentioned composition for organic optoelectronic devices is a composition in which the first compound, the second compound, and the third compound are mixed, wherein the first compound may be included in an amount of 20 wt% to 50 wt% based on the total weight of the first compound, the second compound may be included in an amount of 40 wt% to 60 wt% based on the total weight of the first compound, the second compound, and the third compound may be included in an amount of 10 wt% to 30 wt% based on the total weight of the first compound, the second compound, and the third compound.

[0256] Within the aforementioned range, for example, based on the total weight of the first compound for the organic optoelectronic element, the second compound for the organic optoelectronic element, and the third compound for the organic optoelectronic element, the first compound for the organic optoelectronic element may be included in an amount of about 25 wt% to 45 wt%; based on the total weight of the first compound for the organic optoelectronic element, the second compound for the organic optoelectronic element, and the third compound for the organic optoelectronic element, the second compound for the organic optoelectronic element may be included in an amount of about 45 wt% to 60 wt%; and based on the total weight of the first compound for the organic optoelectronic element, the second compound for the organic optoelectronic element, and the third compound for the organic optoelectronic element, the third compound for the organic optoelectronic element may be included in an amount of about 10 wt% to 25 wt%.

[0257] Furthermore, as a specific example, the first compound may be included in an amount of about 30 wt% to 40 wt% based on the total weight of the first compound, the second compound, and the third compound; the second compound may be included in an amount of about 45 wt% to 55 wt% based on the total weight of the first compound, the second compound, and the third compound; and the third compound may be included in an amount of about 10 wt% to 20 wt% based on the total weight of the first compound, the second compound, and the third compound.

[0258] As a more specific example, the composition for organic optoelectronic devices comprises a first compound: a second compound: a third compound in a weight ratio of about 40:50:10, about 35:55:10, or about 32:48:20.

[0259] Within the aforementioned range, the electron transport capability of the first compound, the hole transport capability of the second compound, and the buffering capability of the third compound are appropriately coordinated to improve the efficiency and lifespan of the device.

[0260] The first compound can be, for example, one of the compounds selected from Group 1.

[0261] [Group 1]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] The second compound can be, for example, one of the compounds selected from group 2.

[0268] [Group 2]

[0269]

[0270]

[0271]

[0272] For example, the third compound may be one of the compounds selected from Group 3A and Group 3B.

[0273] [Group 3]

[0274]

[0275]

[0276] [Group 3B]

[0277]

[0278]

[0279] The first compound comprises a nitrogen-containing six-membered ring with high electron transport properties, and thus can stably and efficiently transport electrons to reduce driving voltage, improve current efficiency, and achieve long device life.

[0280] The second compound has a structure containing carbazole with high HOMO energy, and therefore can effectively inject and transport holes, thereby contributing to improved device characteristics.

[0281] The third compound has a wide HOMO-LUMO band gap, thereby controlling the migration rates of holes and electrons in the first and second compounds, and thus preventing hole trapping and exciton quenching by relative movement of the luminescent layer region, which helps to improve the lifetime characteristics of the device.

[0282] A three-body composition comprising a first compound, a second compound, and a third compound can achieve an optimal balance by finely tuning the electron / hole characteristics in the device stack compared to a composition, and can significantly improve device characteristics due to proper charge balance compared to a two-body composition (such as a composition comprising a first compound and a second compound or a composition comprising a first compound and a third compound).

[0283] The composition of the mixture of the first compound, the second compound and the third compound can, for example, be included as a phosphorescent host in the light-emitting layer of an organic light-emitting diode, which will be described later.

[0284] In addition to the first compound, the second compound, and the third compound, the composition for organic optoelectronic devices may also contain one or more compounds.

[0285] The composition for use in organic optoelectronic devices may also contain dopants. Dopants may be, for example, phosphorescent dopants, such as red, green, or blue phosphorescent dopants, and may be, for example, green phosphorescent dopants.

[0286] A dopant is a material that is mixed in small amounts with a first compound, a second compound, and a third compound to induce luminescence, and is typically a material such as a metal complex that emits light by being excited multiple times to a triplet or multiply state. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more of these types can be used.

[0287] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds comprising Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0288] [Chemical Formula Z]

[0289] L 9 MX 3

[0290] In the chemical formula Z, M is a metal, and L 9 and X 3 The same or different ligands that form coordination compounds with M.

[0291] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 9 and X 3 It could be, for example, a bidentate ligand.

[0292] By L 9 and X 3 Examples of ligands may be selected from the chemical formula of group D, but are not limited thereto.

[0293] [Group D]

[0294]

[0295] In group D,

[0296] R 300 To R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen, and

[0297] R 303 To R 324 Each of the following is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0298] For example, it can include dopants represented by chemical formula IV.

[0299] [Chemical Formula IV]

[0300]

[0301] In chemical formula IV,

[0302] R 101 To R 116Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,

[0303] R 132 To R 134 Each is independently a C1 to C6 alkyl group.

[0304] R 101 To R 116 At least one of them is a functional group represented by chemical formula IV-1.

[0305] L 100 It is a bidentate ligand for monovalent anions, and a ligand coordinated with iridium via lone pair electrons or heteroatoms.

[0306] n1 and n2 are each any integer from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0307] [Chemical Formula IV-1]

[0308]

[0309] In chemical formula IV-1,

[0310] R 135 To R 139 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,and

[0311] * indicates a portion connected to a carbon atom.

[0312] As an example, it may contain dopants represented by the chemical formula Z-1.

[0313] [Chemical Formula Z-1]

[0314]

[0315] In chemical formula Z-1, rings A, B, C, and D are each independently a five-membered carbon ring, a six-membered carbon ring, or a heterocycle;

[0316] R A R B R C and R D Each can be used independently to indicate mono-, di-, tri-, or tetra-substituted, or unsubstituted.

[0317] LB L C and L D Each is independently selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0318] When nA is 1, L E Selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E It does not exist; and

[0319] R A R B R C R D R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; any adjacent R A R B R C R D R and R' are optionally connected to each other to provide a loop; X B X C X D and X E Each is independently selected from carbon and nitrogen; and Q 1 Q 2 Q 3 and Q 4 Each represents oxygen or a direct bond.

[0320] According to one embodiment, the dopant may be a platinum complex and may be represented, for example, by chemical formula V.

[0321] [Chemical Formula V]

[0322]

[0323] In chemical formula V,

[0324] X 100 Selected from O, S and NR 131 ,

[0325] R 117 To R 131 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132R 133 R 134 ,

[0326] R 132 To R 134 Each is independently a C1 to C6 alkyl group, and

[0327] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 Or tert-butyl.

[0328] Compositions for organic optoelectronic devices can be formed by dry film formation methods such as chemical vapor deposition (CVD).

[0329] The following describes an organic optoelectronic element comprising the above-described composition for an organic optoelectronic element.

[0330] Without particular restrictions, an organic optoelectronic element can be any device that converts electrical energy into light energy and vice versa, and can be, for example, an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, and an organic photosensitive drum.

[0331] In this paper, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic element with reference to the accompanying drawings.

[0332] Figure 1 and Figure 2 This is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0333] refer to Figure 1 An organic light-emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110.

[0334] The anode 120 may be made of a conductor with a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal or an alloy thereof such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc.; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metals and oxides such as ZnO and Al or SnO2 and Sb; and conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but not limited thereto.

[0335] The cathode 110 may be made of a conductor with a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal or alloy thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0336] The organic layer 105 may contain the above-described composition for organic optoelectronic devices.

[0337] The organic layer 105 may include, for example, a light-emitting layer 130, and the light-emitting layer 130 may include, for example, the composition described above for organic optoelectronic devices.

[0338] The above-mentioned compositions for organic optoelectronic devices can be, for example, green light-emitting compositions.

[0339] The luminescent layer 130 may include, for example, the first compound, the second compound, and the third compound described above as the phosphorescent host.

[0340] refer to Figure 2 In addition to the light-emitting layer 130, the organic light-emitting diode 200 also includes a hole-assist layer 140. The hole-assist layer 140 further increases hole injection and / or hole mobility and blocks electrons between the anode 120 and the light-emitting layer 130. For example, the hole-assist layer 140 may be a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.

[0341] The hole assist layer 140 may include at least one of the compounds in group E, for example.

[0342] Specifically, the hole auxiliary layer 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds in group E may be included in the hole transport auxiliary layer.

[0343] [Group E]

[0344]

[0345]

[0346] In the hole transport auxiliary layer, in addition to compounds, known compounds and similar compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., may be used.

[0347] In one implementation, Figure 1 or Figure 2 In this process, the organic light-emitting diode may also include an electron transport layer, an electron injection layer, or a hole injection layer as an organic layer 105.

[0348] Organic light-emitting diodes 100 and 200 can be manufactured by forming an anode or cathode on a substrate, forming an organic layer by using dry film forming methods such as vacuum deposition (evaporation), sputtering, plasma electroplating and ion electroplating, and forming a cathode or anode thereon.

[0349] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0350] In the following description, implementation methods are illustrated in more detail with reference to embodiments. However, these embodiments are exemplary, and the scope of the claims is not limited thereto.

[0351] (Synthesis of the first compound)

[0352] Synthesis Example 1: Synthesis of intermediate Int-6

[0353] [Reaction Scheme 1]

[0354]

[0355] Step 1: Synthesis of intermediate Int-1

[0356] In a round-bottom flask, 11-bromo-4-chloro-2-fluorobenzene (61 g, 291 mmol), 2,6-dimethoxyphenylboronic acid (50.4 g, 277 mmol), K₂CO₃ (60.4 g, 437 mmol), and Pd(PPh₃)₄ (10.1 g, 8.7 mmol) were dissolved in THF (500 mL) and distilled water (200 mL), and then stirred under reflux at 60 °C for 12 hours. When the reaction was complete, after removing the aqueous layer, column chromatography (hexane:DCM (20%)) was performed to give 38 g (51%) of intermediate Int-1.

[0357] Step 2: Synthesis of intermediate Int-2

[0358] Intermediate Int-1 (38 g, 142 mmol) and pyridine hydrochloride (165 g, 1425 mmol) were placed in a round-bottom flask and stirred under reflux at 200 °C for 24 hours. When the reaction was complete, the product was cooled to room temperature and slowly poured into distilled water, followed by stirring for 1 hour. The solid was filtered off to obtain 23 g of intermediate Int-2 (68%).

[0359] Step 3: Synthesis of intermediate Int-3

[0360] In a round-bottom flask, intermediate Int-2 (23 g, 96 mmol) and K₂CO₃ (20 g, 144 mmol) were dissolved in NMP (100 mL), and the mixture was stirred under reflux at 180 °C for 12 h. When the reaction was complete, the mixture was poured into excess distilled water. The solid was then filtered off, dissolved in ethyl acetate, dried over MgSO₄, and the organic layer was removed under reduced pressure. Column chromatography (hexane:ethyl acetate 30%) was performed to give 16 g (76%) of intermediate Int-3.

[0361] Step 4: Synthesis of intermediate Int-4

[0362] In a round-bottom flask, intermediate Int-3 (16 g, 73 mmol) and pyridine (12 ml, 146 mmol) were dissolved in DCM (200 ml). After lowering the temperature to 0 °C, trifluoromethanesulfonic anhydride (14.7 ml, 88 mmol) was slowly added dropwise. After stirring the resulting mixture for 6 hours, when the reaction was complete, excess distilled water was added, followed by stirring for 30 minutes and extraction with DCM. After removing the organic solvent under reduced pressure, the remainder was dried under vacuum to give 22.5 g (88%) of intermediate Int-4.

[0363] Step 5: Synthesis of intermediate Int-5

[0364] In the same manner as in the first step, 21 g (83%) of intermediate Int-5 was synthesized using intermediate Int-4 (25 g, 71.29 mmol), 3-biphenylboronic acid (16.23 g, 81.78 mmol), K2CO3 (14.78 g, 106.93 mmol) and Pd(PPh3)4 (4.12 g, 3.56 mmol).

[0365] Step 6: Synthesis of intermediate Int-6

[0366] In a round-bottom flask, intermediate Int-5 (21 g, 59.18 mmol), bis(pinacol)diboron (19.54 g, 76.94 mmol), Pd(dppf)Cl2 (2.42 g, 2.96 mmol), tricyclohexylphosphine (3.32 g, 11.84 mmol), and potassium acetate (11.62 g, 118.37 mmol) were dissolved in DMF (320 mL). The mixture was stirred under reflux at 120 °C for 10 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered off and then dissolved in DCM. Water was removed with MgSO4, and the organic solvent was filtered through a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to give 18.49 g (70%) of intermediate Int-6.

[0367] Synthesis Example 2: Synthesis of intermediate Int-7

[0368] [Reaction Scheme 2]

[0369]

[0370] 30 g (132.7 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 17.75 g (106.2 mmol) of carbazole, and 14.03 g (146.0 mmol) of NaOtBu were placed in a round-bottom flask and dissolved in 650 mL of THF. The mixture was then stirred at room temperature for 12 hours. The resulting solid was filtered and stirred in an aqueous layer for 30 minutes. The solid was then filtered and dried to obtain 20 g (42%) of intermediate Int-7.

[0371] Synthesis Example 3: Synthesis of Compounds 1-27

[0372] [Reaction Scheme 3]

[0373]

[0374] 9.5 g (26.6 mmol) of intermediate Int-7, 14.25 g (31.9 mmol) of intermediate Int-6, 9.2 g (66.6 mmol) of K₂CO₃, and 1.5 g (1.3 mmol) of Pd(PPh₃)₄ were placed in a round-bottom flask and dissolved in 100 mL of THF and 40 mL of distilled water. The mixture was then stirred under reflux at 70 °C for 12 hours. When the reaction was complete, the mixture was added to 500 mL of methanol, and the crystalline solid was filtered off. The solid was dissolved in monochlorostyrene (MCB), filtered through silica gel, and recrystallized from methanol after removing appropriate amounts of organic solvent to obtain 13.1 g (77%) of compound 1-27.

[0375] (LC / MS theoretical value: 640.23 g / mol, measured value: M+ = 641.39 g / mol)

[0376] Synthesis Example 3: Synthesis of intermediate Int-14

[0377] [Reaction Scheme 3]

[0378]

[0379] 2,4-Dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol), carbazole (17.75 g, 106.17 mmol), and sodium tert-butoxide (14.03 g, 145.98 mmol) were placed in a round-bottom flask and stirred with THF (650 ml) at room temperature for 12 hours. The resulting solid was filtered and stirred in an aqueous layer for 30 minutes. After filtration, the product was dried to give 20 g (42%) of intermediate Int-14.

[0380] Synthesis Example 4: Synthesis of Compounds 1-27

[0381] [Reaction Scheme 4]

[0382]

[0383] Intermediates Int-14 (9.5 g, 26.62 mmol), Int-6 (14.26 g, 31.95 mmol), K₂CO₃ (9.20 g, 66.56 mmol), and Pd(PPh₃)₄ (1.54 g, 1.33 mmol) were placed in a round-bottom flask and dissolved in THF (100 mL) and distilled water (40 mL). The mixture was then stirred under reflux at 70 °C for 12 hours. When the reaction was complete, the mixture was added to 500 mL of methanol to crystallize the solid. The solid was filtered, dissolved in monochlorobenzene, filtered with silica gel / diatomaceous earth, and recrystallized from methanol after removing appropriate amounts of organic solvent to give 13.14 g (77%) of compound 1-27.

[0384] (LC / MS theoretical value: 640.23 g / mol, measured value: M+ = 641.39 g / mol)

[0385] Synthesis Example 5: Synthesis of Compounds 1-24

[0386] [Reaction Scheme 5]

[0387]

[0388] Step 1: Synthesis of intermediate Int-8

[0389] 23.4 g (87.3 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was added to 100 mL of THF, 100 mL of toluene, and 100 mL of distilled water. 0.9 equivalents of 4-chlorophenylboronic acid, 0.03 equivalents of Pd(PPh3)4, and 2 equivalents of K2CO3 were then added, followed by reflux and stirring under nitrogen atmosphere for 6 hours. After removing the aqueous layer, the organic layer was dried under reduced pressure. The resulting solid was washed with water and hexane, and then recrystallized from 200 mL of toluene to give 20 g (67%) of intermediate Int-8.

[0390] Step 2: Synthesis of intermediate Int-9

[0391] 35 g (142 mmol) of 3-bromo-9H-carbazole was dissolved in 500 mL of THF, and 17.3 g (142 mmol) of phenylboronic acid and 8.2 g (7.1 mmol) of Pd(PPh3)4 were added, followed by stirring. 49.1 g (356 mmol) of K2CO3 saturated in water was added, and the mixture was stirred under reflux at 80 °C for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with DCM, treated with MgSO4 to remove water, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by column chromatography (hexane:DCM (20%)) to obtain 22.0 g (64%) of intermediate Int-9.

[0392] Step 3: Synthesis of compounds 1-24

[0393] 22.0 g (90.4 mmol) of intermediate Int-9, 31.1 g (90.4 mmol) of intermediate Int-8, 13.1 g (135.6 mmol) of NaOtBu, 2.5 g (2.7 mmol) of Pd2(dba)3 and 5.5 g (50% in toluene) of P(t-Bu)3 were added to 300 mL of xylene, and the mixture was stirred under reflux for 12 hours under a nitrogen stream. After removing the xylene, 200 mL of methanol was added to the resulting mixture, and the crystallized solid was filtered off, dissolved in MCB and filtered through silica gel. The organic solvent was then concentrated to obtain 32 g (64%) of compound 1-24.

[0394] (LC / MS theoretical value: 550.22 g / mol, measured value: M+ = 551.23 g / mol)

[0395] Synthesis Example 6: Synthesis of Compounds 1-41

[0396] [Reaction Scheme 6]

[0397]

[0398] Step 1: Synthesis of intermediate Int-10

[0399] 15 g (58.5 mmol) of indo[2,3B-a]carbazole, 18.1 g (58.5 mmol) of 3-bromo-m-terphenyl, 1.6 g (1.8 mmol) of Pd2(dba)3, 2.8 mL (5.8 mmol) of P(t-Bu)3 and 8.4 g (87.8 mmol) of NaOtBu were suspended in 300 mL of xylene and stirred under reflux at 120 °C for 12 hours. When the reaction was complete, distilled water was added, and the mixture was stirred for 30 minutes and extracted. The organic layer was then purified separately by silica gel column chromatography (hexane:DCM (30%)) to obtain 16.2 g (57%) of intermediate Int-10.

[0400] Step 2: Synthesis of compounds 1-41

[0401] Using the same method as in the third step of Synthesis Example 4, 16.1 g (33.2 mmol) of intermediate Int-10 and 8.9 g (33.2 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine were used to obtain 11.4 g (48%) of compound 1-41.

[0402] (LC / MS theoretical value: 715.27 g / mol, measured value: M+ = 716.29 g / mol)

[0403] Synthesis Example 7: Synthesis of Compounds 1-25

[0404] [Reaction Scheme 7]

[0405]

[0406] Step 1: Synthesis of Intermediate A

[0407] 65.5 g (216.79 mmol) of 2-[1,1'-diphenyl]-4-yl-4,6-dichloro-1,3,5-triazine and 25 g (149.51 mmol) of carbazole were suspended in 800 mL of THF, and 15.09 g (156.99 mmol) of NaO (t-Bu) was slowly added to it. After stirring the mixture at room temperature for 12 hours, the resulting solid was filtered off and washed with distilled water, acetone, and hexane to obtain 40.15 g (62% yield) of intermediate A.

[0408] Step 2: Synthesis of compounds 1-25

[0409] 10 g (23.10 mmol) of intermediate A, 8.70 g (23.56 mmol) of 3-(9H-carbazole-9-yl)phenylboronic acid, 0.8 g (0.69 mmol) of Pd(PPh3)4, and 6.39 g (46.2 mmol) of K2CO3 were suspended in 100 mL of THF and 50 mL of distilled water, and then stirred under reflux for 12 hours. When the reaction was complete, the resulting solid was filtered after cooling to room temperature and washed with distilled water and acetone. The resulting solid was heated and dissolved in 200 mL of dichlorobenzene, filtered through silica gel, and recrystallized in 150 mL of dichlorobenzene to obtain 11 g (74% yield) of compound 1-25.

[0410] (LC / MS theoretical value: 639.75 g / mol, measured value: 640.40 g / mol)

[0411] Synthesis Example 8: Synthesis of Compounds 1-46

[0412] [Reaction Scheme 8]

[0413]

[0414] Step 1: Synthesis of intermediate Int-12

[0415] 12 g (46.8 mmol) of indo[2,3B-a]carbazole, 14.5 g (46.8 mmol) of 1-bromo-3,5-diphenylbenzene, 1.3 g (1.4 mmol) of Pd2(dba)3, 2.3 ml (4.7 mmol) of P(t-Bu)3, and 6.8 g (70.2 mmol) of NaOtBu were suspended in 220 ml of xylene and stirred under reflux at 120 °C for 12 hours. When the reaction was complete, distilled water was added, and the mixture was stirred for 30 minutes and extracted. The organic layer was then purified separately by silica gel column chromatography (hexane:DCM (30%)) to obtain 13.6 g (60%) of intermediate Int-12.

[0416] Step 2: Synthesis of compounds 1-46

[0417] 13 g (26.8 mmol) of intermediate Int-12 and 1.3 g (53.7 mmol) of NaH were suspended in 150 mL of anhydrous N,N-dimethylformamide (DMF) and stirred under a nitrogen stream. Subsequently, 11.1 g (32.2 mmol) of 2-chloro-4-phenyl-6-(4-biphenyl)-1,3,5-triazine was suspended in 70 mL of anhydrous DMF and slowly added dropwise to the mixture. After the dropwise addition was complete, the resulting mixture was stirred for 6 hours. When the reaction was complete, distilled water was added, and the precipitated crystals were filtered and dried. The crystals were recrystallized in 150 mL of DCB to obtain 8.3 g (39%) of compound 1-46.

[0418] (LC / MS theoretical value: 791.30 g / mol, measured value: 792.11 g / mol)

[0419] Synthesis Example 9: Synthesis of Compounds 1-73

[0420] [Reaction Scheme 9]

[0421]

[0422] Step 1: Synthesis of intermediate Int-13

[0423] 50 g (202.4 mmol) of 4-bromodibenzofuran, 38.7 g (303.53 mmol) of 2-chloroaniline, 9.3 g (10.2 mmol) of Pd2(dba)3, 7.4 ml (30.4 mmol) of P(t-bu)3, and 29.2 g (303.5 mmol) of NaOtBu were placed in a round-bottom flask and dissolved in 650 ml of toluene. The mixture was then stirred under reflux at 130 °C for 12 hours. When the reaction was complete, after removing the aqueous layer, the residue was treated by column chromatography (hexane:DCM (20%)) to obtain 38 g (64%) of intermediate Int-13.

[0424] Step 2: Synthesis of intermediate Int-14

[0425] 50 g (170.2 mmol) of intermediate Int-13, 7.8 g (8.5 mmol) of Pd2(dba)3, 110.9 g (340.4 mmol) of CS2CO3, and 6.3 g (17.0 mmol) of PCy3·HBF4 (tricyclohexylphosphine tetrafluoroborate) were placed in a round-bottom flask and dissolved in 550 mL of DMAc. The mixture was then stirred under reflux at 160 °C for 12 hours. When the reaction was complete, excess distilled water was added, and the mixture was stirred for 1 hour. The solid was filtered and dissolved in MCB at high temperature. The water was then removed with MgSO4, and the organic solvent was filtered through a silica gel sieve while stirring the filtrate. The obtained solid was filtered and dried under vacuum to obtain 26.9 g (62%) of intermediate Int-14.

[0426] Step 3: Synthesis of compounds 1-73

[0427] 11.5 g (44.7 mmol) of intermediate Int-14, 18.4 g (53.7 mmol) of 2-chloro-4-phenyl-6-(4-biphenyl)-1,3,5-triazine, and 2.2 g (89.5 mmol) of NaH were placed in a round-bottom flask and dissolved in 180 mL of anhydrous DMF. The mixture was then stirred under reflux at room temperature for 12 hours. When the reaction was complete, excess distilled water was added, and the mixture was stirred for 1 hour. The solid was filtered and dissolved in hot MCB. The water was removed with MgSO4, and the organic solvent was filtered through a silica gel pad, followed by stirring of the filtrate. The obtained solid was filtered and dried under vacuum to give 22.1 g (88%) of compound 1-73.

[0428] (LC / MS theoretical value: 561.21 g / mol, measured value: 562.62 g / mol)

[0429] (Synthesis of the second compound)

[0430] Synthesis Example 10: Synthesis of Compound 2-1

[0431] It was synthesized in the same manner as described in KR10-2017-0068927A.

[0432] Synthesis Example 11: Synthesis of Compound 2-2

[0433] It was synthesized in the same manner as described in KR10-2017-0037277A.

[0434] Synthetic Example 12: Synthesis of Compound 2-15

[0435] [Reaction Scheme 10]

[0436]

[0437] Step 1: Synthesis of intermediate Int2-15-1

[0438] In a round-bottom flask, 10.44 g (42.41 mmol) of 4-bromo-9H-carbazole, 11.88 g (42.41 mmol) of 4-iodo-1,1'-diphenyl (Aldrich), 0.388 g (0.424 mmol) of Pd2(dba)3, 0.206 g (0.848 mmol) of P(t-Bu)3, and 6.11 g (63.61 mmol) of NaO(t-Bu) were suspended in 420 mL of toluene and stirred at 60 °C for 12 hours. After the reaction was complete, distilled water was added, the mixture was stirred for 30 minutes, and extracted. The organic layer was then subjected to column chromatography on a silica gel column (hexane / dichloromethane = 9:1 (v / v)) to obtain 14.70 g (87% yield) of intermediate 2-15-1.

[0439] Step 2: Synthesis of intermediate Int2-15-2

[0440] In a round-bottom flask, 15.50 g (38.92 mmol) of synthetic intermediate 2-15-1, 7.15 g (42.81 mmol) of (2-nitrophenyl)boric acid, 16.14 g (116.75 mmol) of potassium carbonate, and 1.35 g (1.17 mmol) of tetrakis(triphenylphosphine)palladium(O)(Pd(PPh3)4) were suspended in 150 mL of toluene and 70 mL of distilled water, and then stirred under reflux for 12 hours. The mixture was then extracted with dichloromethane and distilled water, and the organic layer was filtered through silica gel. The organic solution was then removed, and the product solid was recrystallized from dichloromethane and n-hexane to obtain 13.72 g (80% yield) of intermediate 2-15-2.

[0441] Step 3: Synthesis of intermediate Int2-15-3

[0442] 22.46 g (51.00 mmol) of intermediate 2-15-2 and 52.8 mL of triethyl phosphite were placed in a round-bottom flask, purged with nitrogen, and stirred at 160 °C for 12 hours. When the reaction was complete, 3 L of MeOH was added, followed by filtration and evaporation of the filtrate. The product (hexane) was purified by column chromatography to give 10.42 g (yield: 50%) of intermediate 2-15-3.

[0443] Step 4: Synthesis of Compound 2-15

[0444] Compound 2-15 was synthesized in the same manner as the first step of Synthetic Example 12 (yield: 60%) by using intermediate 2-15-3 and 1-iodo-3-phenylbenzene.

[0445] (LC / MS theoretical value: 560.23 g / mol, measured value: 561.57 g / mol)

[0446] Synthetic Example 13: Synthesis of Compound 2-33

[0447] [Reaction Scheme 11]

[0448]

[0449] Step 1: Synthesis of intermediate Int-15

[0450] 10.4 g (42.4 mmol) of 4-bromo-9H-carbazole, 11.9 g (42.4 mmol) of 4-iodo-1,1'-biphenyl, 0.39 g (0.42 mmol) of Pd2(dba)3, 0.21 g (0.85 mmol) of P(t-Bu)3 and 6.1 g (63.6 mmol) of NaO were added. t- Bu was suspended in 420 ml of toluene and then stirred at 60 °C for 12 hours. When the reaction was complete, distilled water was added and then stirred for 30 minutes, extracted, and treated by column chromatography (hexane:DCM (10%)) to obtain 14.7 g (87%) of intermediate Int-15.

[0451] Step 2: Synthesis of intermediate Int-16

[0452] 15.5 g (38.9 mmol) of intermediate Int-15, 7.2 g (42.8 mmol) of 2-nitrophenylboronic acid, 16.1 g (116.7 mmol) of K₂CO₃, and 1.4 g (1.2 mmol) of Pd(PPh₃)₄ were suspended in 150 mL of toluene and 70 mL of distilled water, and then stirred under reflux for 12 hours. The product was treated with DCM and distilled water, and the organic layer therefrom was filtered through silica gel. Subsequently, after removing the organic solution, the solid produced therefrom was recrystallized with DCM and hexane to obtain 13.7 g (80%) of intermediate Int-16.

[0453] Step 3: Synthesis of intermediate Int-17

[0454] 22.5 g (51.0 mmol) of intermediate Int-16 and 52.8 mL of triethyl phosphite were added, and after purging with nitrogen, the mixture was stirred under reflux at 160 °C for 12 hours. When the reaction was complete, 3 L of methanol was added, followed by stirring and filtration, and the filtrate was distilled under reduced pressure. The product obtained by column chromatography (hexane:DCM (10%)) yielded 10.4 g (50%) of intermediate Int-17.

[0455] Step 4: Synthesis of Compounds 2-33

[0456] Compounds 2-33 were synthesized using the synthesized intermediate Int-17 and 3B-iodobiphenyl, in the same manner as in the first step of synthetic example 13.

[0457] (LC / MS theoretical value: 560.23 g / mol, measured value: 561.57 g / mol)

[0458] Synthetic Example 14: Synthesis of Compound 2-13

[0459] [Reaction Scheme 12]

[0460]

[0461] Step 1: Synthesis of intermediate Int2-13-1

[0462] In a round-bottom flask, 18.23 g (40.94 mmol) of 2-[9-([1,1'-biphenyl]-4-yl)-9H-carbazole-3-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentane, 11.08 g (45.03 mmol) of 2-bromo-9H-carbazole, 11.32 g (81.88 mmol) of potassium carbonate, and 1.42 g (1.23 mmol) of tetra(triphenylphosphine)palladium(0)(Pd(PPh3)4) were suspended in 180 mL of tetrahydrofuran (THF) and 75 mL of distilled water, and then stirred under reflux for 12 hours. After extraction with dichloromethane and distilled water, the organic layer was filtered through silica gel. Subsequently, after removing the organic solution, the product solid was recrystallized from it with dichloromethane and n-hexane to obtain 18.05 g (yield: 91%) of intermediate 2-13-1.

[0463] Step 2: Synthesis of compound 2-13

[0464] In a round-bottom flask, 13.29 g (27.42 mmol) of intermediate 2-13-1, 6.39 g (27.42 mmol) of 1-bromo-4-phenylbenzene, 0.25 g (0.274 mmol) of Pd2(dba)3, 0.133 g (0.274 mmol) of P(t-Bu)3, and 3.95 g (41.13 mmol) of NaO(t-Bu) were suspended in 300 mL of toluene and stirred at 60 °C for 12 h. When the reaction was complete, distilled water was added, and the mixture was stirred for 30 min and extracted. The organic layer was then columnarized separately through a silica gel column (hexane / dichloromethane = 9:1 (v / v)) to give 15.37 g (yield: 88%) of compound 2-13.

[0465] LC mass (theoretical value: 636.26 g / mol, measured value: M+ = 637.40 g / mol)

[0466] Synthesis Example 15: Synthesis of Compounds 2-8

[0467] [Reaction Scheme 13]

[0468]

[0469] Step 1: Synthesis of intermediate Int-19

[0470] Under a nitrogen atmosphere, 105 g (600 mmol) of 2-bromo-1-fluorobenzene, 87.8 g (720 mmol) of phenylboronic acid, 124.4 g (900 mmol) of K₂CO₃, and 20.8 g (18 mmol) of Pd(PPh₃)₄ were suspended in 1200 mL of THF and 450 mL of distilled water, and then stirred under reflux for 12 hours. When the reaction was complete, the reactants were extracted with DCM and treated by column chromatography (hexane:DCM (10%)) to obtain 77.5 g (75%) of intermediate Int-19.

[0471] Step 2: Synthesis of intermediate Int-20

[0472] Under a nitrogen atmosphere, 30 g (174.2 mmol) of intermediate Int-19, 55.7 g (226.5 mmol) of 3B-bromo-9H-carbazole, and 8.4 g (348.5 mmol) of NaH were suspended in 290 mL of N-methyl-2-pyrrolidone (NMP), and the mixture was stirred under reflux for 18 hours. The reaction mixture was then slowly poured into an excess of water, stirred, and the solids were filtered off to obtain 41.6 g (60%) of intermediate Int-20.

[0473] Step 3: Synthesis of compounds 2-8

[0474] Under a nitrogen atmosphere, 25.0 g (62.8 mmol) of intermediate Int-20, 27.9 g (62.8 mmol) of 9-(4-biphenyl)-3-(tetramethyl-1,3,2-dioxaborphane-2-yl)-9H-carbazole, 17.4 g (125.5 mmol) of K₂CO₃, and 2.2 g (1.9 mmol) of Pd(PPh₃)₄ were suspended in 120 mL of THF and 60 mL of distilled water, and then stirred under reflux for 12 hours. When the reaction was complete, the reactants were extracted with DCM and treated by column chromatography (hexane:DCM (30%)), and the solid obtained was recrystallized from 250 mL of toluene to give 31.9 g (80%) of compounds 2-8.

[0475] LC mass (theoretical value: 636.78 g / mol, measured value: M+ = 637.87 g / mol)

[0476] (Third compound)

[0477] Synthesis Example 16: Synthesis of Compound 3A-1

[0478] [Reaction Scheme 14]

[0479]

[0480] Step 1: Synthesis of intermediate Int3-1

[0481] Under a nitrogen atmosphere, 50.3 g (142.1 mmol) of 4,4,5,5-tetramethyl-2-(benzophenanthrene-2-yl)-1,3,2-dioxaborhecyclopentane, 40.2 g (142.1 mmol) of 1-bromo-3-iodobenzene, 29.5 g (213.2 mmol) of K₂CO₃, and 4.9 g (4.3 mmol) of Pd(PPh₃)₄ were suspended in 280 mL of THF and 110 mL of distilled water, and then stirred under reflux for 8 hours. When the reaction was complete, the reactants were extracted with DCM and treated by column chromatography (hexane:DCM (20%)) to obtain 39.3 g (78%) of intermediate Int3-1.

[0482] Step 2: Synthesis of intermediate Int3-2

[0483] 77 g (203.3 mmol) of intermediate Int3-1, 59.4 g (233.8 mmol) of bis(pinacol)diboron, 4.8 g (5.9 mmol) of Pd(dppf)Cl2, and 28.9 g (294.8 mmol) of potassium acetate were placed in a round-bottom flask and dissolved in 400 mL of DMF. The mixture was stirred under reflux at 120 °C for 12 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing water with MgSO4, the organic solvent was filtered through a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to give 41.8 g (70%) of intermediate Int3-2.

[0484] Step 3: Synthesis of compound 3A-1

[0485] 61.2 g (142.1 mmol) of intermediate Int-3-2, 56.2 g (142.1 mmol) of 4-bromo-9,9'-spirodi[9H-fluorene], 29.5 g (213.2 mmol) of K₂CO₃, and 4.9 g (4.3 mmol) of Pd(PPh₃)₄ were suspended in 280 mL of THF and 110 mL of distilled water, and then stirred under reflux for 8 hours under a nitrogen atmosphere. When the reaction was complete, the product was extracted with DCM and then treated by column chromatography (hexane:DCM (20%)) to give 39.3 g (78%) of compound 3A-1.

[0486] LC mass (theoretical value: 618.23 g / mol, measured value: M+ = 619.40 g / mol)

[0487] Synthesis Example 17: Synthesis of Compound 3A-2

[0488] [Reaction Scheme 15]

[0489]

[0490] Step 1: Synthesis of intermediate Int3-3

[0491] Under a nitrogen atmosphere, 50.3 g (142.1 mmol) of 4,4,5,5-tetramethyl-2-(benzophenanthrene-2-yl)-1,3,2-dioxaborhecyclopentane, 40.2 g (142.1 mmol) of 1-bromo-4-iodobenzene, 29.5 g (213.2 mmol) of K₂CO₃, and 4.9 g (4.3 mmol) of Pd(PPh₃)₄ were suspended in 280 mL of THF and 110 mL of distilled water, and then stirred under reflux for 8 hours. When the reaction was complete, the reactants were extracted with DCM and treated by column chromatography (hexane:DCM (20%)) to give 43.6 g (80%) of the intermediate Int3-3 as a solid.

[0492] Step 2: Synthesis of intermediate Int3-4

[0493] 77 g (203.3 mmol) of intermediate Int3-3, 59.4 g (233.8 mmol) of bis(pinacol)diboron, 4.8 g (5.9 mmol) of Pd(dppf)Cl2, and 28.9 g (294.8 mmol) of potassium acetate were placed in a round-bottom flask and dissolved in 400 mL of DMF. The mixture was stirred under reflux at 120 °C for 12 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered off and dissolved in DCM. After removing water with MgSO4, the organic solvent was filtered off using a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to give 65.6 g (75%) of intermediate Int3-4.

[0494] Step 3: Synthesis of compound 3A-2

[0495] Under a nitrogen atmosphere, 61.2 g (142.1 mmol) of intermediate Int3-4, 56.2 g (142.1 mmol) of 4-bromo-9,9'-spirodi[9H-fluorene], 29.5 g (213.2 mmol) of K2CO3, and 4.9 g (4.3 mmol) of Pd(PPh3)4 were suspended in 280 mL of THF and 110 mL of distilled water and stirred under reflux for 8 hours. When the reaction was complete, the reactants were extracted with DCM and treated by column chromatography (hexane:DCM (20%)) to give 39.3 g (78%) of compound 3A-2 as a solid.

[0496] LC mass (theoretical value: 618.23 g / mol, measured value: M+ = 619.39 g / mol)

[0497] Synthetic Example 18: Synthesis of Compound 3B-4

[0498] [Reaction Scheme 16]

[0499]

[0500] Step 1: Synthesis of intermediate Int-21

[0501] 50 g (203.3 mmol) of 1-bromodibenzofuran, 59.4 g (233.8 mmol) of bis(pinacol)diboron, 4.8 g (5.9 mmol) of Pd(dppf)Cl2, and 28.9 g (294.8 mmol) of potassium acetate were placed in a round-bottom flask and dissolved in 400 mL of DMF. The mixture was stirred under reflux at 120 °C for 12 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing the water with MgSO4, the organic solvent was filtered through a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to give 41.8 g (70%) of intermediate Int-21.

[0502] Step 2: Synthesis of intermediate Int-22

[0503] Under a nitrogen atmosphere, 37.9 g (142.1 mmol) of 4-bromo-3'-chloro-1,1'-biphenyl, 41.8 g (142.1 mmol) of intermediate Int-21, 29.5 g (213.2 mmol) of K₂CO₃, and 4.9 g (4.3 mmol) of Pd(PPh₃)₄ were suspended in 280 mL of THF and 110 mL of distilled water, and then stirred under reflux for 8 hours. When the reaction was complete, the reactants were extracted with DCM and treated by column chromatography (hexane:DCM (20%)) to give 39.3 g (78%) of intermediate Int-22 as a solid.

[0504] Step 3: Synthesis of compound 3B-4

[0505] Under a nitrogen atmosphere, 39.3 g (110.8 mmol) of intermediate Int-22, 39.2 g (110.8 mmol) of 4,4,5,5-tetramethyl-2-(benzophenanthrene-2-yl)-1,3,2-dioxaborane, 65.0 g (199.4 mmol) of Cs₂CO₃, 5.1 g (5.5 mmol) of Pd₂(dba)₃, and 8.9 g (22.2 mmol) of P(t-Bu)₃ were suspended in 440 mL of 1,4-dioxane and stirred under reflux for 8 hours. When the reaction was complete, after cooling to room temperature, excess methanol was added to form a solid, and the solid was filtered. The filtered solid was then washed with distilled water, methanol, and acetone, and recrystallized from 400 mL of MCB to give 29.1 g (48%) of compound 3B-4.

[0506] LC mass (theoretical value: 546.66 g / mol, measured value: M+ = 547.51 g / mol)

[0507] Synthetic Example 19: Synthesis of Compound 3B-7

[0508] [Reaction Scheme 17]

[0509]

[0510] Step 1: Synthesis of intermediate Int-23

[0511] Except that 4-bromodibenzothiophene was used instead of 1-bromodibenzofuran, 28 g (55%) of intermediate Int-23 was synthesized and purified in the same manner as in the first step of Synthetic Example 18.

[0512] Step 2: Synthesis of intermediate Int-24

[0513] Except that 3B-bromo-3'-chloro-1,1'-biphenyl was used instead of 4-bromo-3'-chloro-1,1'-biphenyl, 22 g (65%) of intermediate Int-24 was synthesized and purified in the same manner as in the second step of synthetic example 18.

[0514] Step 3: Synthesis of compound 3B-7

[0515] Except for the use of intermediate Int-24, 11.1 g (39%) of compound 3B-7 was synthesized and purified in the same manner as in the third step of synthetic example 18.

[0516] LC mass (theoretical value: 562.72 g / mol, measured value: M+ = 563.57 g / mol)

[0517] Synthesis Example 20: Synthesis of Compound 3B-2

[0518] [Reaction Scheme 18]

[0519]

[0520] Step 1: Synthesis of intermediate Int-21

[0521] Except for the use of intermediate Int-21, 19.1 g (45%) of compound 3B-7 was synthesized and purified in the same manner as in the first step of synthetic example 18.

[0522] Step 2: Synthesis of intermediate Int-25

[0523] Except that 3B-bromo-3'-chloro-1,1'-biphenyl was used instead of 4-bromo-3'-chloro-1,1'-biphenyl, 26.2 g (65%) of intermediate Int-25 was synthesized and purified in the same manner as in the second step of synthetic example 18.

[0524] Step 3: Synthesis of compound 3B-2

[0525] Except for the use of intermediate Int-25, 9.5 g (48%) of compound 3B-2 was synthesized and purified in the same manner as in the third step of synthesis example 18.

[0526] LC mass (theoretical value: 546.20 g / mol, measured value: M+ = 547.88 g / mol)

[0527] Synthetic Example 21: Synthesis of Compound 3B-13

[0528] [Reaction Scheme 19]

[0529]

[0530] Step 1: Synthesis of intermediate Int-26

[0531] Under a nitrogen atmosphere, 41.8 g (169.2 mmol) of 4-bromodibenzofuran, 24.8 g (203.3 mmol) of phenylboronic acid, 46.8 g (338.3 mmol) of K₂CO₃, and 5.9 g (5.1 mmol) of Pd(PPh₃)₄ were suspended in 340 mL of THF and 170 mL of distilled water, and then stirred under reflux for 8 hours. When the reaction was complete, the reactants were extracted with DCM and treated by column chromatography (hexane:DCM (20%)) to give 28.5 g (69%) of intermediate Int-26 as a solid.

[0532] Step 2: Synthesis of intermediate Int-27

[0533] Under a nitrogen atmosphere, 28.5 g (116.7 mmol) of the intermediate Int-26 was dissolved in 250 mL of THF in a round-bottom flask and stirred at -78 °C for 30 min. Subsequently, 51.3 mL (128.3 mmol) of n-butyllithium (2.5 M solution) was slowly added dropwise over 1 h, followed by stirring for another 4 h. A solution obtained by diluting 29.6 g (116.7 mmol) of iodine with THF was slowly added dropwise at -78 °C, followed by stirring at room temperature for 4 h. When the reaction was complete, a saturated aqueous solution of sodium bicarbonate and DCM were added, followed by stirring for 1 h. The organic layer was separated and filtered through a silica gel pad to remove the solvent under reduced pressure, yielding 34.6 g (80%) of the intermediate Int-27.

[0534] Step 3: Synthesis of compound 3B-13

[0535] Except for the use of intermediate Int-27, 29.2 g (81%) of compound 3B-13 was synthesized and purified in the same manner as in the third step of synthetic example 18.

[0536] LC mass (theoretical value: 546.66 g / mol, measured value: M+ = 547.64 g / mol)

[0537] Synthesis Example 22: Synthesis of Compound 3B-3

[0538] [Reaction Scheme 20]

[0539]

[0540] Step 1: Synthesis of intermediate Int-28

[0541] Except that 4-bromodibenzofuran was used instead of 1-bromodibenzofuran, 12.2 g (68%) of intermediate Int-28 was synthesized and purified in the same manner as in the first and second steps of Synthetic Example 18.

[0542] Step 2: Synthesis of compound 3B-3

[0543] Except for the use of intermediate Int-28, 9.1 g (56%) of compound 3B-3 was synthesized and purified in the same manner as in the third step of synthetic example 18.

[0544] LC mass (theoretical value: 546.20 g / mol, measured value: M+ = 547.82 g / mol)

[0545] (Synthesis of dopants)

[0546] Synthesis Example 23: Dopant Compound PtGD

[0547] [PtGD]

[0548]

[0549] It is synthesized in the same manner as described in KR1999337.

[0550] (Manufacturing of Organic Light Emitting Diodes)

[0551] Example 1

[0552] A glass substrate coated with ITO (indium tin oxide) was washed with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent (such as isopropanol, acetone, methanol, etc.) and dried. It was then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum depositor. Using the ITO transparent electrode thus obtained as the anode, compound A (available from Novalde) doped with 3% NDP-9 was vacuum deposited onto the ITO substrate to form... A thick hole transport layer is formed, and compound B is deposited on the hole transport layer to create... A thick hole transport assist layer was formed on the hole transport assist layer by simultaneously vacuum depositing compounds 1-27, 2-2, and 3A-2 as the main components and doping with 15 wt% PtGD as a dopant. A thick luminescent layer. In this document, compounds 1-27, 2-2, and 3A-2 are used in a weight ratio of 35:55:10, and the ratios are described separately for the following examples and comparative examples. Subsequently, compound C is deposited on the luminescent layer to form... A thick electron transport auxiliary layer was formed, and compounds D and Liq were simultaneously vacuum-deposited at a 1:1 weight ratio to form A thick electron transport layer. LiQ and Al are sequentially vacuum-deposited onto the electron transport layer. Thick and harmonious Thick, to manufacture organic light-emitting diodes with the following structure.

[0553] ITO / Compound A (3% NDP-9 doped) Compound B / EML{[85wt% of the main body (1-27:2-2:3A-2=35:55:10):15wt% [PtGD]}; / Compound C / Compound D:LiQ / LiQ / Al

[0554] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0555] Compound B: N,N-bis(9,9-dimethyl-9H-fluorene-4-yl)-9,9-spirodi(fluorene)-2-amine

[0556] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluorene-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0557] Compound D: 8-(4-(4,6-bis(naphthyl-2-yl)-1,3,5-triazin-2-yl)phenyl)quinolone

[0558] [PtGD]

[0559]

[0560] Examples 2 to 9 and Comparative Examples 1 to 13

[0561] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that the composition was changed to the main body shown in Tables 1 to 6.

[0562] Assessment I

[0563] The efficiency and lifetime of the organic light-emitting diodes according to Examples 1 to 3 and Comparative Examples 1 to 6 were measured.

[0564] The specific measurement methods are as follows, and the results are shown in Tables 1 to 3.

[0565] (1) Measurement of current density change based on voltage change

[0566] The obtained organic light-emitting diode was measured by increasing the voltage from 0V to 10V using a current-voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0567] (2) Measurement of brightness change based on voltage change

[0568] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a luminance meter (MinoltaCs-1000A).

[0569] (3-1) Measurement of luminous efficiency I

[0570] Using the luminance, current density, and voltage measured from (1) and (2), the current efficiency (cd / A) for the desired luminance of 9000 nits was calculated. The relative efficiency ratios are shown based on the luminous efficiency values ​​of Comparative Example 1, Comparative Example 3, and Comparative Example 5.

[0571] (4-1) Measurement of Lifetime I

[0572] By maintaining brightness (cd / m 2 ) is 24000 cd / m 2 The results were obtained by simultaneously measuring the time it took for the current efficiency (cd / A) to decrease to 95%. The relative lifetime ratios are shown based on the lifetime values ​​of Comparative Example 1, Comparative Example 3, and Comparative Example 5, respectively.

[0573] (Table 1)

[0574]

[0575] (Table 2)

[0576]

[0577] (Table 3)

[0578]

[0579] Referring to Tables 1 to 3, compared with the organic light-emitting diodes according to Comparative Examples 1 to 6, the organic light-emitting diodes according to Examples 1 to 3 have significantly improved lifetimes while maintaining the same or higher efficiency.

[0580] Assessment II

[0581] The efficiency and lifetime of the organic light-emitting diodes according to Examples 4 to 9 and Comparative Examples 7 to 13 were measured.

[0582] The specific measurement methods are as follows, and the results are shown in Tables 4 to 6.

[0583] (1) Measurement of current density change based on voltage change

[0584] The obtained organic light-emitting diode was measured by increasing the voltage from 0V to 10V using a current-voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0585] (2) Measurement of brightness change based on voltage change

[0586] The brightness was measured using a luminance meter (MinoltaCs-1000A) while the voltage of the organic light-emitting diode was increased from 0V to 10V.

[0587] (3-2) Measurement of luminous efficiency II

[0588] Using the brightness, current density, and voltage measured from (1) and (2), calculate the same current density (10 mA / cm²). 2 The current efficiency (cd / A) is shown. The relative efficiency ratios are shown based on the luminous efficiency values ​​of Comparative Example 7, Comparative Example 10, and Comparative Example 12.

[0589] (4-2) Measurement of Lifetime II

[0590] Through 9000cd / m 2 Initial brightness (cd / m²) 2 The T90 lifetime of the organic light-emitting diodes of Examples 4 to 9 and Comparative Examples 7 to 13 was measured by emitting light under light and measuring the decrease in brightness over time to obtain the T97 lifetime when the brightness decreased to 97% of the initial brightness. The relative efficiency ratios are shown based on the luminous efficiency values ​​of Comparative Examples 7, 10, and 12.

[0591] (Table 4)

[0592]

[0593] (Table 5)

[0594]

[0595]

[0596] (Table 6)

[0597]

[0598] Referring to Tables 4 to 6, compared with the organic light-emitting diodes according to Comparative Examples 7 to 13, the organic light-emitting diodes according to Examples 4 to 9 maintain a similar efficiency level while showing a significantly improved lifetime.

[0599] Although the invention has been described in conjunction with what is now considered a particular embodiment, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A composition for use in organic optoelectronic devices, comprising... First compound; Second compound; as well as The third compound, The first compound is represented by chemical formula IA or chemical formula IE. The second compound is represented by the chemical formula IIA, and The third compound is represented by the chemical formula ⅢB. The compound comprises, based on the total weight of the first compound, the second compound, and the third compound, in an amount of 30 wt% to 40 wt%, in an amount of 45 wt% to 55 wt%, and in an amount of 10 wt% to 20 wt%. [Chemical Formula IA] [Chemical Formula IE] Among them, in chemical formulas IA and IE, Z 1 To Z 3 Is it N or CL? a -R a , Z 1 To Z 3 At least two of them are N. L a and L 1 To L 3 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R 1 and R 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. X 1 Is it O, S, or NR? b ,and R a R b R 3 To R 6 and R 10 To R 12 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, or a combination thereof; [Chemical Formula IIA] In chemical formula IIA, L 4 L 5 and L 8 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a combination thereof, and R 13 To R 18 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl; [Chemical Formula IIIB] In chemical formula IIIB, L 8 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group. R 34 To R 41 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl, and X 2 It is O or S.

2. The composition for organic optoelectronic devices according to claim 1, wherein, The first compound is represented by any one of the chemical formulas IA.

3. The composition for organic optoelectronic devices according to claim 2, wherein, Chemical formula IA is represented by chemical formula IA-1 or chemical formula IA-4: [Chemical Formula IA-1] [Chemical Formula IA-4] Among them, in chemical formulas IA-1 and IA-4, Z 1 To Z 3 L 1 To L 3 R 1 and R 2 The definition is the same as in claim 1, and R 3 It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted indolocarbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenel.

4. The composition for organic optoelectronic devices according to claim 1, wherein, Chemical formula IIA can be represented by any one of the chemical formulas IIA-1 to IIA-3: [Chemical Formula IIA-1] [Chemical Formula IIA-2] [Chemical Formula IIA-3] Among them, in chemical formulas IIA-1 to IIA-3, L 4 L 5 Ar 1 Ar 2 and R 13 To R 18 The definition is the same as in claim 1.

5. The composition for organic optoelectronic devices according to claim 4, wherein, Chemical formula IIA is represented by chemical formula IIA-1 or chemical formula IIA-2, and Among them, in chemical formulas IIA-1 and IIA-2, R 13 To R 18 Each is either hydrogen or deuterium. L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted phenylene, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

6. The composition for organic optoelectronic devices according to claim 1, wherein, Chemical formula IIIB is represented by chemical formulas IIIB-1 to IIIB-4: [Chemical Formula IIIB-1] [Chemical Formula IIIB-2] [Chemical Formula IIIB-3] [Chemical Formula IIIB-4] Among them, in chemical formulas IIIB-1 to IIIB-4, X 2 L 8 and R 34 To R 41 The definition is the same as in claim 1.

7. The composition for organic optoelectronic devices according to claim 6, wherein, Chemical formula IIIB is represented by chemical formula IIIB-1 or chemical formula IIIB-4.

8. The composition for organic optoelectronic devices according to claim 1, wherein, The first compound is represented by the chemical formula IA-1. The second compound is represented by the chemical formula IIA-1, and The third compound is represented by the chemical formula ⅢB-4. [Chemical Formula IA-1] [Chemical Formula IIA-1] [Chemical Formula IIIB-4] In chemical formula IA-1, Z 1 To Z 3 Each is N, L 1 To L 3 Each is independently a single bond or a substituted or unsubstituted phenylene group, and R 1 and R 2 Each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene. In chemical formula IIA-1, R 13 To R 18 Each is independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group. L 4 and L 5 Each is independently a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene, and Ar 1 and Ar 2 Each of them is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. In the chemical formula IIIB-4, X 2 It is O or S, and L 8 Linking groups selected from Group I, Group I ， R 34 To R 41 Each is independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

9. The composition for organic optoelectronic devices according to claim 1, wherein, The first compound is represented by the chemical formula ICE-1. The second compound is represented by the chemical formula IIA-1, and The third compound is represented by chemical formula IIIB-1 or chemical formula IIIB-4: [Chemical Formula IE-1] [Chemical Formula IIA-1] In chemical formula IE-1, X 1 It is NR b Or O, R b It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted triphenyl. Z 1 To Z 3 Each is N, L 1 To L 3 Each is independently a single bond or a substituted or unsubstituted phenylene, and R 1 and R 2 Each is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl. In chemical formula IIA-1, R 13 To R 18 Each is independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group. L 4 and L 5 Each is independently a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene, and Ar 1 and Ar 2 Each of them is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. [Chemical Formula IIIB-1] [Chemical Formula IIIB-4] Among them, in chemical formulas IIIB-1 and IIIB-4, X 2 It is O or S, and L 8 Linking groups selected from Group I, Group I ， R 34 To R 41 Each is independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

10. An organic optoelectronic element comprising: The anode and cathode facing each other, and At least one organic layer between the anode and the cathode in, The organic layer comprises a composition for an organic optoelectronic element according to any one of claims 1 to 9.

11. A display device comprising the organic optoelectronic element according to claim 10.

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