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

Abstract

Disclosed are a composition for an organic optoelectric device, an organic optoelectric device, and a display device, the composition comprising a first compound for an organic optoelectric device represented by a combination of Chemical Formula 1 and Chemical Formula 2 and a second compound for an organic optoelectric device represented by Chemical Formula 3. In Chemical Formula 1 to Chemical Formula 3, each substituent is the same as described in the specification.

Description

[0001] This application is a divisional application of the invention patent application filed on October 8, 2019, with application number 201910950006.8 and invention title "Composition for Organic Optoelectronic Device, Organic Optoelectronic Device and Display Device".

[0002] Citations of relevant applications

[0003] This application claims priority and benefit to Korean Patent Application No. 10-2018-0118385, filed on October 4, 2018, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0004] Compositions, organic optoelectronic devices, and display devices for use in organic optoelectronic devices are disclosed. Background Technology

[0005] Organic photoelectric devices (organic photodiodes) are devices that convert electrical energy into light energy (and vice versa).

[0006] Based on their driving principle, organic optoelectronic devices can be classified as follows. One type is an optoelectronic device in which excitons generated by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy. The other type is a light-emitting device that generates light energy from electrical energy by providing voltage or current to the electrodes.

[0007] Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting diodes (OLEDs), organic solar cells, and organic photosensitive drums.

[0008] Organic light-emitting diodes (OLEDs) have recently attracted attention due to the increasing demand for flat panel displays. OLEDs convert electrical energy into light, and their performance is greatly influenced by the organic materials arranged between the electrodes. Summary of the Invention

[0009] One embodiment provides a composition for organic optoelectronic devices that enables high efficiency and long lifespan.

[0010] Another embodiment provides an organic optoelectronic device comprising a composition for an organic optoelectronic device.

[0011] Another embodiment provides a display device that includes an organic optoelectronic device.

[0012] According to one embodiment, the composition for an organic optoelectronic device includes a first compound for an organic optoelectronic device represented by a combination of chemical formula 1 and chemical formula 2, and a second compound for an organic optoelectronic device represented by chemical formula 3.

[0013]

[0014] In chemical formula 1 and chemical formula 2,

[0015] X is O or S.

[0016] Two adjacent pairs of a1* to a4* are connected to b1* and b2* respectively.

[0017] The remaining portions of a1* to a4* that are not connected to b1* and b2* are each independently CL. a -R a ,

[0018] L a and L 1 To L 4 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.

[0019] R a and R 1 To R 6 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, 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, and

[0020] R 1 To R 4 At least one of them is a group represented by the chemical formula a.

[0021] [Chemical formula a]

[0022]

[0023] In chemical formula a,

[0024] L b and L c 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.

[0025] R b and R c 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, and

[0026] *is related to L 1 To L 4 The connection point;

[0027] [Chemical Formula 3]

[0028]

[0029] In chemical formula 3,

[0030] L 5 To L 9 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.

[0031] Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0032] R 7 To R 10 Each of the following 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, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof.

[0033] R 7 To R 10 They exist independently, or their adjacent groups are connected to each other to form substituted or unsubstituted aliphatic monocyclic or substituted or unsubstituted aliphatic polycyclic, substituted or unsubstituted aromatic monocyclic or substituted or unsubstituted aromatic polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or substituted or unsubstituted heteroaromatic polycyclic.

[0034] Ar and R 7 To R 10 At least one of them is a group represented by chemical formula b.

[0035] [Chemical formula b]

[0036]

[0037] In chemical formula b,

[0038] Z 1 To Z 5 Each is independently N or CL d -R d ,

[0039] Z 1 To Z 5At least two of them are N.

[0040] Where L d 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.

[0041] R d Each of the following 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, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof.

[0042] R d Each exists independently, or its adjacent groups are connected to each other to form a substituted or unsubstituted aliphatic monocyclic or substituted or unsubstituted aliphatic polycyclic, a substituted or unsubstituted aromatic monocyclic or substituted or unsubstituted aromatic polycyclic, or a substituted or unsubstituted heteroaromatic monocyclic or substituted or unsubstituted heteroaromatic polycyclic, and

[0043] *is related to L 5 To L 9 The connection point.

[0044] According to another embodiment, the organic optoelectronic device includes an anode and a cathode facing each other and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the composition described above for the organic optoelectronic device.

[0045] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0046] It can realize organic optoelectronic devices with high efficiency and long life. Attached Figure Description

[0047] Figure 1 and Figure 2 This is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0048] <Symbol Explanation>

[0049] 100, 200: Organic Light Emitting Diodes

[0050] 105: Organic layer

[0051] 110: Cathode

[0052] 120: Anode

[0053] 130: Emissive layer

[0054] 140: Hole auxiliary layer Detailed Implementation

[0055] Embodiments of the present invention are described in detail below. However, these embodiments are exemplary, and the invention is not limited thereto and is defined by the scope of the claims.

[0056] As used herein, unless otherwise defined, “substituted” 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.

[0057] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, 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, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. Additionally, in a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, pyridyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophenyl, or carbazoleyl. Furthermore, in specific embodiments of the present invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, dibenzofuranyl, or dibenzothiopheneyl. Additionally, in specific embodiments of the present invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl, or dibenzothiopheneyl.

[0058] As used herein, unless otherwise defined, “heteroatom” means a group that contains one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon in a functional group.

[0059] 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 are connected by σ bonds, such as biphenyl, terphenyl, tetraphenyl, etc.; and groups in which two or more aromatic hydrocarbon moiety are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene, etc.

[0060] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0061] In this specification, "heterocyclic group" is a general concept of heteroaryl and may include at least one heteroatom selected from N, O, S, P, and Si to replace carbon (C) in cyclic compounds such as aryl, cycloalkyl, their fused rings, or combinations thereof. When the heterocyclic group is fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0062] For example, "heteroaryl" can represent an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly linked by σ bonds, or when a heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may comprise 1 to 3 heteroatoms.

[0063] 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 phenanthryl, a substituted or unsubstituted naphthacenyl, 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, or a substituted or unsubstituted terphenyl. The radical, substituted or unsubstituted triphenylene group (benzophenanthrene), substituted or unsubstituted dinaphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indene, or combinations thereof, but not limited thereto.

[0064] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole 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... Benzothiophene, 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 naphthidyl, 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 dibenzothiaophene, or combinations thereof, but not limited thereto.

[0065] As used herein, “adjacent groups are connected to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic, or a substituted or unsubstituted aromatic monocyclic or polycyclic heterocyclic” means that any two adjacent groups are directly connected by a single bond, without a connecting group, to replace the substituents of the aromatic ring or aromatic heterocyclic ring to form another ring.

[0066] For example, adjacent groups are connected to each other to form other rings of a substituted or unsubstituted aromatic monocyclic ring or other rings of a substituted or unsubstituted aromatic polycyclic ring, and examples may be other rings of a substituted or unsubstituted aromatic monocyclic ring.

[0067] For example, any two substituents of the benzene ring of carbazole can be linked together to form other rings, thereby forming substituted or unsubstituted benzocarbazole groups or substituted or unsubstituted dibenzocarbazole groups together with the benzene ring of carbazole.

[0068] For example, any two substituents that directly replace a nitrogen-containing hexagonal ring can be linked together to form other rings, thereby forming substituted or unsubstituted quinazoline groups or substituted or unsubstituted quinoxaline groups together with the nitrogen-containing hexagonal ring.

[0069] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and based on the highest occupied molecular orbital (HOMO) level, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductivity.

[0070] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and based on the minimum unoccupied molecular orbital (LUMO) level, due to conductivity properties, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0071] The following describes a composition for an organic optoelectronic device according to an embodiment.

[0072] The composition for an organic optoelectronic device includes a first compound having hole properties and a second compound having electronic properties.

[0073] The first compound used in organic optoelectronic devices is represented by a combination of chemical formula 1 and chemical formula 2.

[0074]

[0075] In chemical formula 1 and chemical formula 2,

[0076] X is O or S.

[0077] Two adjacent pairs of a1* to a4* are connected to b1* and b2* respectively.

[0078] The remaining portions of a1* to a4* that are not connected to b1* and b2* are each independently CL. a -R a ,

[0079] L a and L 1 To L 4 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.

[0080] R a and R 1 To R 6 Each group is independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, 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. For example, it may include -L thereon. 1 -R 1 -L 2 -R 2 -L 3 -R3 and -L 4 -R 4 The remaining carbon atoms in each ring can have hydrogen atoms bonded to them.

[0081] For example, R 1 To R 4 At least one of them is a substituted amino group represented by chemical formula a.

[0082] [Chemical formula a]

[0083]

[0084] In chemical formula a,

[0085] L b and L c 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.

[0086] R b and R c 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, and

[0087] *is related to L 1 To L 4 The connection point.

[0088] The first compound for use in organic optoelectronic devices has a structure in which an amine substituted with an aryl and / or heteroaryl group is attached to a fused heterocycle consisting of a 6-membered ring-5-6-membered ring-5-6-membered ring, and thus exhibits high HOMO energy due to the extension of the HOMO electron cloud from the amine to the fused heterocycle, and displays excellent hole injection and transport properties.

[0089] Furthermore, since the fused heterocycle of 6-membered ring-5-membered ring-6-membered ring-5-membered ring-6-membered ring has a relatively high HOMO energy compared with bicarbazole and indolocarbazole, devices with low driving voltages can be realized by applying structures that connect amines to fused heterocycles.

[0090] In addition, bicarbazole and indolocarbazole have high T1 energies and are therefore unsuitable as red hosts, but structures that link amines to fused heterocycles have suitable T1 energies as red hosts.

[0091] On the other hand, since the first compound includes fused heterocycles and exhibits reduced symmetry in the molecule and thus its crystallization from the compound is suppressed, black spots caused by compound crystallization during material deposition during the device manufacturing process can be suppressed, and thus the lifespan of the device can be improved.

[0092] Therefore, devices produced by applying the first compound for organic optoelectronic devices according to the present invention can achieve high efficiency / long lifespan characteristics.

[0093] On the other hand, including the first compound together with the second compound for organic optoelectronic devices and thus exhibiting satisfactory interfacial properties and hole and electron transport capabilities, and thus reducing the driving voltage of devices produced by applying the compound.

[0094] For example, L b and L c They can each be a single bond or a substituted or unsubstituted C6 to C12 aryl group.

[0095] For example, L b and L c Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0096] For example, R b and R c 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 anthraquinone, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a monovalent group of a fused ring represented by a combination of Formula 1 and Formula 2. For example, R b and / or R c It can be a monovalent group consisting of a fused combination of a substituted or unsubstituted C2-C30 heterocyclic group and a substituted or unsubstituted C6-C30 aryl group forming a compound represented by a combination of chemical formulas 1 and 2. For example, R b and / or R c It can be a monovalent group of a fused heterocycle consisting of a 6-membered ring, a 5-membered ring, a 6-membered ring, a 5-membered ring, and a 6-membered ring. For example, the hydrogen in the combination of chemical formula 1 and chemical formula 2 can be L... b L c The bonding sites of , and / or N are replaced to form R. b and / or R c Monovalent groups.

[0097] For specific examples, R b and R cEach of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, or a fused ring represented by a combination of Formula 1 and Formula 2.

[0098] For example, R b and R c Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted fluorenyl.

[0099] For example, L a and L 1 To L 4 They can each be a single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0100] For a specific example, L a and L 1 To L 4 Each can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.

[0101] For example, L a and L 1 To L 4 Each can be a single bond or a substituted or unsubstituted p-phenylene group.

[0102] For example, R a and R 1 To R 4 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C20 aryl.

[0103] For example, R a and R 1 To R 4 They can each be hydrogen independently, but are not limited to this.

[0104] For example, R 5 and R 6 Each can be independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C20 aryl.

[0105] For example, R 5 and R 6 Each can be independently a substituted or unsubstituted C1 to C4 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0106] For example, based on the combination point of chemical formula 1 and chemical formula 2, the first compound for organic optoelectronic devices can be represented by one of chemical formulas 1A to 1F.

[0107]

[0108] In chemical formulas 1A to 1F, X and L a and L 1 To L 4 and R a and R 1 To R 6 Same as above.

[0109] For example, depending on the direction of substitution of the group represented by chemical formula a, chemical formula 1A can be represented by chemical formula 1A-1 or chemical formula 1A-2.

[0110]

[0111] In chemical formulas 1A-1 and 1A-2, X and L a L b L c L 1 To L 4 R a R 1 To R 6 R b and R c Same as above.

[0112] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1A-1 can be represented by one of chemical formulas 1A-1-1 to 1A-1-4.

[0113]

[0114]

[0115] In chemical formulas 1A-1-1 to 1A-1-4, X and L a L b L c L 1 To L 4 R a R 1 To R 6 R b and R c Same as above.

[0116] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1A-2 can be represented by one of chemical formulas 1A-2-1 to 1A-2-4.

[0117]

[0118] In chemical formulas 1A-2-1 to 1A-2-4, X and L a L b L c and L 1 To L 4 and R 1 To R 6 and R b and R c Same as above.

[0119] In one embodiment, chemical formula 1A may be represented by one of chemical formula 1A-1-1, chemical formula 1A-2-2, and chemical formula 1A-2-3.

[0120] For example, depending on the direction of substitution of the group represented by chemical formula a, chemical formula 1B can be represented by chemical formula 1B-1 or chemical formula 1B-2.

[0121]

[0122] In chemical formulas 1B-1 and 1B-2, X and L a L b L c L 1 To L 4 R a R 1 To R 6 R b and R c Same as above.

[0123] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1B-1 can be represented by one of chemical formulas 1B-1-1 to 1B-1-4.

[0124]

[0125]

[0126] In chemical formulas 1B-1-1 to 1B-1-4, X and L a L b L c L 1 To L 4 R a R 1 To R 6 R b and R c Same as above.

[0127] For example, depending on the substitution position of the group represented by chemical formula a, chemical formula 1B-2 can be represented by one of chemical formulas 1B-2-1 to 1B-2-4.

[0128]

[0129] In chemical formulas 1B-2-1 to 1B-2-4, X and L a L b L c L 1 To L 4 R a R 1 To R 6 R b and R c Same as above.

[0130] In one embodiment, chemical formula 1B may be represented by one of chemical formula 1B-1-1, chemical formula 1B-2-2, and chemical formula 1B-2-3.

[0131] For example, depending on the substitution direction of the group represented by chemical formula a, chemical formula 1C can be represented by chemical formula 1C-1 or chemical formula 1C-2.

[0132]

[0133] In chemical formulas 1C-1 and 1C-2, X and L a L b L c L 1 To L 4 R a R 1 To R 6 R b and R c Same as above.

[0134] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1C-1 can be represented by one of chemical formulas 1C-1-1 to 1C-1-4.

[0135]

[0136]

[0137] In chemical formulas 1C-1-1 to 1C-1-4, X and L a L b L c L 1 To L 4 Ra R 1 To R 6 R b and R c Same as above.

[0138] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1C-2 can be represented by one of chemical formulas 1C-2-1 to 1C-2-4.

[0139]

[0140] In chemical formulas 1C-2-1 to 1C-2-4, X and L a L b L c L 1 To L 4 R a R 1 To R 6 R b and R c Same as above.

[0141] In one embodiment, chemical formula 1C may be represented by one of chemical formula 1C-1-1, chemical formula 1C-2-2, and chemical formula 1C-2-3.

[0142] For example, depending on the direction of substitution of the group represented by chemical formula a, chemical formula 1D can be represented by chemical formula 1D-1 or chemical formula 1D-2.

[0143]

[0144] In chemical formulas 1D-1 and 1D-2, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0145] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1D-1 can be represented by one of chemical formulas 1D-1-1 to 1D-1-4.

[0146]

[0147]

[0148] In chemical formulas 1D-1-1 to 1D-1-4, X and La L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0149] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1D-2 can be represented by one of chemical formulas 1D-2-1 to 1D-2-4.

[0150]

[0151] In chemical formulas 1D-2-1 to 1D-2-4, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0152] In one embodiment, chemical formula 1D may be represented by one of chemical formula 1D-1-1, chemical formula 1D-2-2, and chemical formula 1D-2-3.

[0153] For example, depending on the substitution direction of the group represented by chemical formula a, chemical formula 1E can be represented by either chemical formula 1E-1 or chemical formula 1E-2.

[0154]

[0155] In chemical formulas 1E-1 and 1E-2, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0156] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1E-1 can be represented by one of chemical formulas 1E-1-1 to 1E-1-4.

[0157]

[0158]

[0159] In chemical formulas 1E-1-1 to 1E-1-4, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0160] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1E-2 can be represented by one of chemical formulas 1E-2-1 to 1E-2-4.

[0161]

[0162]

[0163] In chemical formulas 1E-2-1 to 1E-2-4, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0164] In one embodiment, chemical formula 1E may be represented by one of chemical formulas 1E-1-1 to 1E-1-4 and chemical formulas 1E-2-1 to 1E-2-4.

[0165] For example, depending on the direction of substitution of the group represented by chemical formula a, chemical formula 1F can be represented by chemical formula 1F-1 or chemical formula 1F-2.

[0166]

[0167] In chemical formulas 1F-1 and 1F-2, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0168] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1F-1 can be represented by one of chemical formulas 1F-1-1 to 1F-1-4.

[0169]

[0170] In chemical formulas 1F-1-1 to 1F-1-4, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0171] For example, depending on the specific substitution position of the group represented by chemical formula a, chemical formula 1F-2 can be represented by one of chemical formulas 1F-2-1 to 1F-2-4.

[0172]

[0173]

[0174] In chemical formulas 1F-2-1 to 1F-2-4, X and L a L b L c L 1 To L 4 R 1 To R 6 R b and R c Same as above.

[0175] In one embodiment, chemical formula 1F can be represented by one of chemical formula 1F-1-1, chemical formula 1F-2-2, and chemical formula 1F-2-3.

[0176] In one embodiment of the invention, the first compound for an organic optoelectronic device may be represented by chemical formula 1E-1-1 or chemical formula 1E-2-2, and may be represented, for example, by chemical formula 1E-2-2.

[0177] The first compound used in an organic optoelectronic device may be, for example, one of the compounds in Group 1, but is not limited thereto.

[0178] [Group 1]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] The second compound used in organic optoelectronic devices is represented by chemical formula 3.

[0189] [Chemical Formula 3]

[0190]

[0191] In chemical formula 3,

[0192] L 5 To L 9 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.

[0193] Ar is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0194] R 7 To R 10 Each of the following 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, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof.

[0195] R 7 To R 10 Each exists independently, or its adjacent groups are connected to each other to form a substituted or unsubstituted aliphatic monocyclic or substituted or unsubstituted aliphatic polycyclic, a substituted or unsubstituted aromatic monocyclic or substituted or unsubstituted aromatic polycyclic, or a substituted or unsubstituted heteroaromatic monocyclic or substituted or unsubstituted heteroaromatic polycyclic, and

[0196] Ar and R 7 To R 10 At least one of them is a group represented by chemical formula b.

[0197] [Chemical formula b]

[0198]

[0199] In chemical formula b,

[0200] Z 1 To Z 5 Each is independently N or CL d -R d ,

[0201] Z 1 To Z 5 At least two of them are N.

[0202] Where L d 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.

[0203] R d Each of the following 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, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof.

[0204] R d Each exists independently, or its adjacent groups are connected to each other to form a substituted or unsubstituted aliphatic monocyclic or substituted or unsubstituted aliphatic polycyclic, a substituted or unsubstituted aromatic monocyclic or substituted or unsubstituted aromatic polycyclic, or a substituted or unsubstituted heteroaromatic monocyclic or substituted or unsubstituted heteroaromatic polycyclic, and

[0205] *is related to L 5 To L 9 The connection point.

[0206] The second compound for use in organic optoelectronic devices is a compound possessing the property of accepting both holes and electrons, i.e., bipolar properties. Specifically, it has a structure in which the carbazole core represented by chemical formula 3 is replaced by a ring comprising at least two nitrogen atoms, such as pyrimidine or triazine, thereby improving the glass transition temperature relative to molecular weight and thus ensuring heat resistance.

[0207] Furthermore, since the second compound for organic optoelectronic devices has fast and stable electron transport characteristics, it can be included together with the aforementioned first compound for organic optoelectronic devices, which has fast and stable hole transport characteristics, to balance holes and electrons in the device and thus reduce the driving voltage of the organic optoelectronic device containing them.

[0208] For example, L5 To L 9 Each can be a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0209] For example, L 5 To L 9 Each of these can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted fused dibenzofuranylene group, a substituted or unsubstituted fused dibenzothiophenylene group, or a combination thereof.

[0210] For example, L 5 To L 9 Each can be independently a single bond, a substituted or unsubstituted meta-phenylene, a substituted or unsubstituted p-phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene.

[0211] For example, Ar can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraceneyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluoreneyl, a group represented by chemical formula b, or a combination thereof.

[0212] For example, Ar can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, or a group represented by chemical formula b, but is not limited thereto.

[0213] For example, R 7 To R 10 Each of these groups can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, a group represented by chemical formula b, or a combination thereof.

[0214] For example, R7 To R 10 Each of these groups may be, independently, hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or a group represented by chemical formula b, but is not limited thereto.

[0215] For example, depending on the bonding position of the group represented by chemical formula b, a second compound for an organic optoelectronic device can be represented, for example, by one of chemical formulas 3A to 3R.

[0216]

[0217]

[0218]

[0219] In chemical formulas 3A to 3R, L 5 To L 9 Ar, R 7 To R 10 and Z 1 To Z 5 Same as above,

[0220] L 10 With the above L 1 To L 9 The definitions are the same.

[0221] R e R f R g R h R i and R j With the above R 7 To R 10 The definitions are the same, and

[0222] Z 1a To Z 5a and Z 1b To Z 5b With the above Z 1 To Z 5 The definitions are the same.

[0223] For example, L d Each can be 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

[0224] For example, L dEach can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0225] For example, L d Each can be a single bond, a substituted or unsubstituted meta-phenylene, or a substituted or unsubstituted p-phenylene, but is not limited thereto.

[0226] For example, R d Each of these can be independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heterocyclic, or a combination thereof.

[0227] For example, R d It can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0228] For example, R d It can be, independently, hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted meta-phenyl, substituted or unsubstituted para-phenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene, but is not limited thereto.

[0229] R d They can exist independently, or their adjacent groups can be connected to each other to form substituted or unsubstituted aliphatic monocyclic or substituted or unsubstituted aliphatic polycyclic, substituted or unsubstituted aromatic monocyclic or substituted or unsubstituted aromatic polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or substituted or unsubstituted heteroaromatic polycyclic.

[0230] For example, in groups represented by the chemical formula b, Z 1 To Z 5 At least two of them can be N, and R d They can exist independently.

[0231] For example, the group represented by chemical formula b can be a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazine group.

[0232] For example, Z 1 and Z 3 It can be N or Z 2 Z 4 and Z 5 Each can be independently designated as CL. d -R d Z 3 and Z 5 It can be N, and Z 1 Z 2 and Z 4 Each can be independently designated as CL. d -R d ; or Z 2 and Z 4 It can be N, and Z 1 Z 3 and Z 5 Each can be independently designated as CL. d -R d In this case, L d and R d Same as above.

[0233] For example, Z 1 Z 3 and Z 5 It can be N, and Z 2 and Z 4 Each can be independently designated as CL. d -R d In this case, L d and R d Same as above.

[0234] For example, in groups represented by the chemical formula b, Z 1 To Z 5 At least two of them can be N, and adjacent R d They connect to each other to form substituted or unsubstituted aromatic monocyclic rings or substituted or unsubstituted aromatic monocyclic heterocyclic rings.

[0235] In this case, the group represented by chemical formula b can be a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a substituted or unsubstituted naphthidyl group.

[0236] For example, Z 3 and Z 4 Each can be independently designated as a CR. d , where adjacent R d They connect to each other to form a benzene ring, and Z 1 Z 2 and Z 5 The two in can be N.

[0237] For example, Z 3 and Z 4 Each can be independently designated as a CR. d , where adjacent R d They connect to each other to form a benzene ring, and each Z 1 Z 2 and Z 5 It can be N.

[0238] For example, chemical formula b can be represented by one of chemical formulas b-1 to b-5, but is not limited to this.

[0239]

[0240]

[0241] In chemical formulas b-1 to b-5, L d2 To L d 5 and L e1 and L e2 With the above L d The definitions are the same, and R d1 To R d5 R k1 and R k2 With the above R d The definitions are the same.

[0242] For specific examples, the group represented by chemical formula b can be a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted naphthidyl group.

[0243] For a more specific instance, chemical formula b can be one of the substituents of group I.

[0244] [Group I]

[0245]

[0246] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3A can be represented by one of chemical formulas 3A-1 to 3A-4.

[0247]

[0248] In chemical formulas 3A-1 to 3A-4, L 5 To L 9 Ar, R 7 To R 10 and Z 1 To Z 5 Same as above.

[0249] For example, chemical formula 3A can be represented by chemical formula 3A-2 or chemical formula 3A-4.

[0250] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3C can be represented by one of chemical formulas 3C-1 to 3C-4.

[0251]

[0252]

[0253] In chemical formulas 3C-1 to 3C-4, L 5 To L 9 R 8 To R 10 Z 1a To Z 5a and Z 1b To Z 5b Same as above.

[0254] For example, chemical formula 3C can be represented by chemical formula 3C-1 or chemical formula 3C-4.

[0255] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3E can be represented by one of chemical formulas 3E-1 to 3E-4.

[0256]

[0257]

[0258] In chemical formulas 3E-1 to 3E-4, L 7 To L 10 R 9 R 10 Z 1 To Z 5 And Ar is the same as above.

[0259] For example, chemical formula 3E can be represented by chemical formula 3E-2.

[0260] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3F can be represented by one of chemical formulas 3F-1 to 3F-4.

[0261]

[0262]

[0263] In chemical formulas 3F-1 to 3F-4, L 7 To L 9 R10 R e R f R g Z 1 To Z 5 And Ar is the same as above.

[0264] For example, the chemical formula 3F can be represented by the chemical formula 3F-3 or the chemical formula 3F-4.

[0265] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3H can be represented by one of chemical formulas 3H-1 to 3H-4.

[0266]

[0267] In chemical formulas 3H⁻¹ to 3H⁻⁴, L 7 To L 10 R e R f R 9 R 10 Z 1 To Z 5 And Ar is the same as above.

[0268] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3I can be represented by one of chemical formulas 3I-1 to 3I-4.

[0269]

[0270] In chemical formulas 3I-1 to 3I-4, L 7 To L 9 R e R f R g R 10 Z 1 To Z 5 And Ar is the same as above.

[0271] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3K can be represented by one of chemical formulas 3K-1 to 3K-4.

[0272]

[0273]

[0274] In chemical formulas 3K-1 to 3K-4, L 7 To L 9 R 9 R 10 Re R f R g Z 1 To Z 5 And Ar is the same as above.

[0275] For example, depending on the specific bonding position of the group represented by chemical formula b, chemical formula 3L can be represented by one of chemical formulas 3L-1 to 3L-4.

[0276]

[0277]

[0278] In chemical formulas 3L⁻¹ to 3L⁻⁴, L 7 To L 9 R 10 R e R f R g Z 1 To Z 5 And Ar is the same as above.

[0279] For example, the chemical formula 3L can be represented by the chemical formula 3L-4.

[0280] In a specific embodiment of the present invention, the second compound for the organic optoelectronic device may be represented by one of chemical formulas 3A, 3B, 3E and 3J.

[0281] In a more specific embodiment of the invention, the second compound for the organic optoelectronic device may be represented by one of chemical formulas 3A-2, 3B, 3E-2, and 3J.

[0282] The second compound used in the organic optoelectronic device can be, for example, one of the compounds in group 2, but is not limited thereto.

[0283] [Group 2]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290] For example, a first compound and a second compound for an organic optoelectronic device may be included in a weight ratio of about 1:99 to about 99:1. Within this range, the hole transport capability of the first compound and the electron transport capability of the second compound can be used to adjust the desired weight ratio to achieve bipolar characteristics, and thus improve efficiency and lifetime. Within this range, they may be included, for example, in a weight ratio of about 10:90 to about 90:10, about 20:80 to about 80:20, about 30:70 to about 70:30, about 40:60 to about 60:40, or about 50:50. For example, they may be included in a weight ratio of about 50:50 to about 60:40, for example, about 50:50 or about 60:40.

[0291] For example, the composition according to an embodiment of the present invention includes a compound represented by chemical formula 1E-2-2 as a first compound for an organic optoelectronic device and a compound represented by one of chemical formulas 3A-2, 3B, 3E-2 and 3J as a second compound for an organic optoelectronic device.

[0292] For example, in chemical formula 1E-2-2, L a L b L c and L 1 To L 4 Each can independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted naphthylene, R a R 1 R 2 and R 4 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, R b and R c Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, or a fused ring represented by a combination of Formula 1 and Formula 2, and R 5 and R 6 Each can be independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0293] In chemical formulas 3A-2, 3B, 3E-2, and 3J, L 5 To L 10Each can independently be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted naphthylene; Ar can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthylene; and R 7 To R 10 R e R f and R g Each can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0294] In addition, Z 1 To Z 5 Each can be N or CL independently. d -R d Z 1 To Z 5 At least two of them can be N, L d Each can be an independent single bond or a substituted or unsubstituted C6 to C12 aryl group, and R d Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0295] In addition to the first compound and the second compound described above for organic optoelectronic devices, the composition may also include one or more compounds.

[0296] The composition may also include a dopant. The dopant may be, for example, a phosphorescent dopant, and may be, for example, a red, green, or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.

[0297] The dopant is mixed in small amounts with a first compound and a second compound for an organic optoelectronic device to cause luminescence, and the dopant is typically a material that emits light by being excited to a triplet state or more multiple times, such as a metal complex. The dopant can be, for example, an inorganic, organic, or organic / inorganic compound, and one or more of these types can be used.

[0298] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds, including 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.

[0299] [Chemical Formula Z]

[0300] L 11 MX

[0301] In the chemical formula Z, M is a metal, and L 11 X may be the same as or different from M, and it is a ligand that forms a complex with M.

[0302] 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 11 X can be, for example, a bidentate ligand.

[0303] Dry film-forming methods, such as chemical vapor deposition, can be used to form films from the composition.

[0304] The following describes an organic optoelectronic device in which the above composition is applied.

[0305] Organic optoelectronic devices can be any device that converts electrical energy into light energy (and vice versa), with no specific limitations, and can be, for example, organic optoelectronic devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0306] In this paper, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device, with reference to the accompanying drawings.

[0307] Figure 1 and Figure 2 This is a cross-sectional view of each organic light-emitting diode according to one embodiment.

[0308] 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.

[0309] 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 such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; 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; a conductive polymer such as, but not limited to, poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0310] The cathode 110 may be made of a conductor having 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 such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or alloys thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0311] The organic layer 105 may include a light-emitting layer 130, which includes the composition described above for organic optoelectronic devices.

[0312] The above-mentioned composition for organic optoelectronic devices may be, for example, a composition that emits red light.

[0313] The light-emitting layer 130 may include, for example, the first compound for organic optoelectronic devices described above and the second compound for organic optoelectronic devices described above, respectively, as phosphorescent hosts.

[0314] refer to Figure 2 The organic light-emitting diode 200 further includes a hole auxiliary layer 140 and a light-emitting layer 130. The hole auxiliary layer 140 can further improve the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons. The hole auxiliary layer 140 can be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and can include at least one layer.

[0315] The hole-assisted layer 140 may include at least one of the compounds in group E, for example.

[0316] Specifically, the hole auxiliary layer 140 may include a hole transport layer located between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer located between the light-emitting layer 130 and the hole transport layer, and may include at least one of the group E compounds in the hole transport auxiliary layer.

[0317] [Group E]

[0318]

[0319]

[0320] In the hole transport auxiliary layer, in addition to the compounds mentioned above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and similar compounds may be used.

[0321] 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 the organic layer 105.

[0322] Organic light-emitting diodes 100 and 200 can be produced by forming an organic layer on a substrate using dry film forming methods such as vacuum deposition (evaporation), sputtering, plasma electroplating, and ion electroplating, and then forming a cathode or anode thereon.

[0323] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0324] In the following description, embodiments are illustrated in more detail with reference to examples. However, these embodiments are exemplary, and the scope of the invention is not limited thereto.

[0325] Unless otherwise specified, the starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods.

[0326] The following synthetic intermediates were synthesized with reference to KR10-1423173B1, etc.

[0327]

[0328] (Preparation of the first compound for organic optoelectronic devices)

[0329] Synthesis Example 1: Synthesis of Compound A-51

[0330] [Reaction Scheme 1]

[0331]

[0332] 5.0 g (15.68 mmol) of intermediate M-3, 5.04 g (15.68 mmol) of intermediate A, 4.52 g (47.95 mmol) of sodium tert-butoxide, and 0.1 g (0.47 mmol) of tri-tert-butylphosphine were dissolved in 200 mL of toluene, and 0.27 g (0.47 mmol) of Pd(dba)₂ was added. The mixture was refluxed under nitrogen atmosphere and stirred for 12 hours. When the reaction was complete, the product was extracted with toluene and distilled water. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography using a 2:1 volume ratio of hexane / dichloromethane to give 7.8 g (yield: 82.3%) of the desired compound A-51 as a white solid.

[0333] Calculated values: C, 89.52; H, 5.51; N, 2.32; O, 2.65

[0334] Analytical values: C, 89.51; H, 5.52; N, 2.32; O, 2.65

[0335] Synthesis Example 2: Synthesis of Compound A-81

[0336] [Reaction Scheme 2]

[0337]

[0338] Except that intermediates M-3 and B were used in a 1:1 ratio, compound A-81 (7.8 g, yield: 80.5%) was synthesized according to the same method as in Synthesis Example 1.

[0339] Calculated values: C, 89.40; H, 5.41; N, 2.42; O, 2.77

[0340] Analytical values: C, 89.42; H, 5.39; N, 2.42; O, 2.77

[0341] Synthesis Example 3: Synthesis of Compound A-82

[0342] [Reaction Scheme 3]

[0343]

[0344] Except that intermediates M-3 and C were used in a 1:1 ratio, compound A-82 (9.2 g, yield: 86.2%) was synthesized according to the same method as in Synthesis Example 1.

[0345] Calculated values: C, 90.10; H, 5.49; N, 2.06; O, 2.35

[0346] Analytical values: C, 90.12; H, 5.47; N, 2.06; O, 2.35

[0347] Synthesis Example 4: Synthesis of Compound A-55

[0348] [Reaction Scheme 4]

[0349]

[0350] Except that intermediates M-3 and D were used in a 1:1 equivalent ratio, compound A-55 (8.6 g, yield: 85.1%) was synthesized according to the same method as in Synthesis Example 1.

[0351] Calculated values: C, 89.55; H, 5.79; N, 2.18; O, 2.49

[0352] Analytical values: C, 89.56; H, 5.78; N, 2.18; O, 2.49

[0353] Synthesis Example 5: Synthesis of Compound A-69

[0354] [Reaction Scheme 5]

[0355]

[0356] Except that intermediates M-3 and E were used in a 1:1 equivalent ratio, compound A-69 (10.5 g, yield: 87%) was synthesized according to the same method as in Synthesis Example 1.

[0357] Calculated values: C, 89.03; H, 5.24; N, 3.64; O, 2.08

[0358] Analytical values: C, 89.01; H, 5.26; N, 3.64; O, 2.08

[0359] Synthesis Example 6: Synthesis of Compound A-75

[0360] [Reaction Scheme 6]

[0361]

[0362] Except that intermediates M-3 and F were used in a 1:1 equivalent ratio, compound A-75 (10.7 g, yield: 87%) was synthesized according to the same method as in Synthesis Example 1.

[0363] Calculated values: C, 87.33; H, 4.76; N, 1.79; O, 6.12

[0364] Analytical values: C, 87.31; H, 4.78; N, 1.79; O, 6.12

[0365] Synthesis Example 7: Synthesis of Compound A-77

[0366] [Reaction Scheme 7]

[0367]

[0368] Except that intermediates M-3 and G were used in a 1:1 equivalent ratio, compound A-77 (10.4 g, yield: 81.2%) was synthesized according to the same method as in Synthesis Example 1.

[0369] Calculated values: C, 83.89; H, 4.57; N, 1.72; O, 1.96; S, 7.86

[0370] Analytical values: C, 83.86; H, 4.59; N, 1.72; O, 1.96; S, 7.86

[0371] Synthesis Example 8: Synthesis of Compound A-79

[0372] [Reaction Scheme 8]

[0373]

[0374] Except that intermediates M-3 and H were used in a 1:1 equivalent ratio, compound A-79 (10.8 g, yield: 86%) was synthesized according to the same method as in Synthesis Example 1.

[0375] Calculated values: C, 85.58; H, 4.66; N, 1.75; O, 4.00; S, 4.01

[0376] Analytical values: C, 85.59; H, 4.67; N, 1.75; O, 4.00; S, 4.01

[0377] Synthesis Example 9: Synthesis of Compound A-83

[0378] [Reaction Scheme 9]

[0379]

[0380] Except that intermediates M-3 and I were used in a 1:1 equivalent ratio, compound A-83 (9.4 g, yield: 81.6%) was synthesized according to the same method as in Synthesis Example 1.

[0381] Calculated values: C, 88.37; H, 5.36; N, 1.91; O, 4.36

[0382] Analytical values: C, 88.35; H, 5.38; N, 1.91; O, 4.36

[0383] Synthesis Example 10: Synthesis of Compound A-84

[0384] [Reaction Scheme 10]

[0385]

[0386] Except that intermediates M-3 and J were used in a 1:1 equivalent ratio, compound A-84 (10.4 g, yield: 76.7%) was synthesized according to the same method as in Synthesis Example 1.

[0387] Calculated values: C, 87.57; H, 5.25; N, 1.62; O, 5.56

[0388] Analytical values: C, 87.59; H, 5.23; N, 1.62; O, 5.56

[0389] Synthesis Example 11: Synthesis of Compound A-52

[0390] [Reaction Scheme 11]

[0391]

[0392] Except that intermediates M-40 and A were used in a 1:1 equivalent ratio, compound A-52 (7.3 g, yield: 88.8%) was synthesized according to the same method as in Synthesis Example 1.

[0393] Calculated values: C, 90.75; H, 5.12; N, 1.92; O, 2.20

[0394] Analytical values: C, 90.73; H, 5.14; N, 1.92; O, 2.20

[0395] Synthesis Example 12: Synthesis of Compound A-53

[0396] [Reaction Scheme 12]

[0397]

[0398] Except that intermediate M-6 and intermediate A were used in a 1:1 equivalent ratio, compound A-53 (7.5 g, yield: 81%) was synthesized according to the same method as in Synthesis Example 1.

[0399] Calculated values: C, 87.20; H, 5.37; N, 2.26; S, 5.17

[0400] Analytical values: C, 87.22; H, 5.35; N, 2.26; S, 5.17

[0401] Synthesis Example 13: Synthesis of Compound A-86

[0402] [Reaction Scheme 13]

[0403]

[0404] Except that intermediates M-6 and B were used in a 1:1 equivalent ratio, compound A-86 (7.6 g, yield: 85.7%) was synthesized according to the same method as in Synthesis Example 1.

[0405] Calculated values: C, 86.98; H, 5.26; N, 2.36; S, 5.40

[0406] Analytical values: C, 86.99; H, 5.25; N, 2.36; S, 5.40

[0407] Synthesis Example 14: Synthesis of Compound A-87

[0408] [Reaction Scheme 14]

[0409]

[0410] Except that intermediates M-6 and C were used in a 1:1 equivalent ratio, compound A-87 (8.2 g, yield: 78.9%) was synthesized according to the same method as in Synthesis Example 1.

[0411] Calculated values: C, 88.02; H, 5.36; N, 2.01; S, 4.61

[0412] Analytical values: C, 88.00; H, 5.38; N, 2.01; S, 4.61

[0413] Synthesis Example 15: Synthesis of Compound A-58

[0414] [Reaction Scheme 15]

[0415]

[0416] Except that intermediates M-6 and D were used in a 1:1 equivalent ratio, compound A-58 (8.4 g, yield: 85.2%) was synthesized according to the same method as in Synthesis Example 1.

[0417] Calculated values: C, 87.37; H, 5.65; N, 2.12; S, 4.86

[0418] Analytical values: C, 87.35; H, 5.67; N, 2.12; S, 4.86

[0419] Synthesis Example 16: Synthesis of Compound A-27

[0420] [Reaction Scheme 16]

[0421]

[0422] Except that intermediates M-11 and A were used in a 1:1 equivalent ratio, compound A-27 (7.3 g, yield: 84.8%) was synthesized according to the same method as in Synthesis Example 1.

[0423] Calculated values: C, 90.10; H, 5.49; N, 2.06; O, 2.35

[0424] Analytical values: C, 90.12; H, 5.47; N, 2.06; O, 2.35

[0425] Synthesis Example 17: Synthesis of Compound A-29

[0426] [Reaction Scheme 17]

[0427]

[0428] Except that intermediate M-16 and intermediate A were used in a 1:1 equivalent ratio, compound A-29 (7.1 g, yield: 83.8%) was synthesized according to the same method as in Synthesis Example 1.

[0429] Calculated values: C, 88.02; H, 5.36; N, 2.01; S, 4.61

[0430] Analytical values: C, 88.04; H, 5.34; N, 2.01; S, 4.61

[0431] Synthesis Example 18: Synthesis of Compound A-92

[0432] [Reaction Scheme 18]

[0433]

[0434] Compound A-92 was synthesized according to the same method as in Synthesis Example 1, except that intermediates M-3 and K were used in a 1:1 equivalent ratio.

[0435] The accurate mass of C43H31NO, calculated by LC / MS: 577.24; measured: 577.77 [M+H]

[0436] Synthesis Example 19: Synthesis of Compound A-93

[0437] [Reaction Scheme 19]

[0438]

[0439] Compound A-93 was synthesized according to the same method as in Synthesis Example 1, except that intermediates M-6 and K were used in a 1:1 equivalent ratio.

[0440] The accurate mass of C43H31NS, calculated by LC / MS: 593.22; measured: 593.78 [M+H]

[0441] Comparative Synthesis Example 1: Synthesis of Comparative Compound 1

[0442] [Reaction Scheme 20]

[0443]

[0444] Compound 3-bromo-9-phenylcarbazole (9.97 g, 30.95 mmol) was dissolved in 200 mL of toluene under nitrogen atmosphere. Biphenylcarbazole boric acid (12.37 g, 34.05 mmol) and tetrakis(triphenylphosphine)palladium (1.07 g, 0.93 mmol) were added, and the mixture was stirred. A saturated aqueous solution of potassium carbonate (12.83 g, 92.86 mmol) was added, and the mixture was heated to 90 °C and refluxed for 12 hours. When the reaction was complete, water was added to the reaction solution, and an extract was obtained using dichloromethane (DCM). After removing the water using anhydrous MgSO4, the extract was filtered and concentrated under reduced pressure. The residue obtained was separated and purified by rapid column chromatography to obtain comparative compound 1 (16 g, 92%).

[0445] The accurate mass of C42H28N2, calculated by LC / MS, is 560.69; the measured mass is 560.73 [M+H].

[0446] Comparative Synthesis Example 2: Synthesis of Comparative Compound 2

[0447] [Reaction Scheme 21]

[0448]

[0449] Comparative compound 2 was synthesized using the same method as in comparative synthesis example 3 of KR2018-0046910.

[0450] (Preparation of the second compound for organic optoelectronic devices)

[0451] Synthesis Example 20: Synthesis of Compound B-12

[0452] [Reaction Scheme 22]

[0453]

[0454] a) Synthesis of intermediate product B-12-1

[0455] Carbazole (35 g, 209.3 mmol), 1-bromo-4-chlorobenzene (60.11 g, 313.98 mmol), CuI (3.99 g, 20.9 mmol), K₂CO₃ (43.39 g, 313.98 mmol), and 1,10-phenanthroline (3.77 g, 20.9 mmol) were placed in a round-bottom flask and dissolved in DMF (700 mL). The solution was stirred at 180 °C for 18 hours. When the reaction was complete, the reaction solvent was removed under reduced pressure, and the obtained product was dissolved in dichloromethane and filtered through silica gel. After concentrating the dichloromethane, the product was recrystallized from hexane to obtain 40.0 g (68.8%) of intermediate B-12-1.

[0456] b) Synthesis of intermediate product B-12-2

[0457] Intermediate B-12-1 (40 g, 144 mmol), bis(pinacolato)diboron (54.86 g, 216 mmol), Pd(dppf)Cl2 (7.1 g, 8.64 mmol), tricyclohexylphosphine (8.08 g, 28.8 mmol), and potassium acetate (42.4 g, 432.04 mmol) were placed in a round-bottom flask and dissolved in DMF (720 mL). The mixture was refluxed at 120 °C and stirred for 12 hours. When the reaction was complete, the mixture was poured into excess distilled water and stirred for one 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 obtained was recrystallized from the solvent with EA and hexane to obtain 31.3 g (58.9%) of intermediate B-12-2.

[0458] c) Synthesis of compound B-12

[0459] Intermediate B-12-2 (31 g, 83.95 mmol) was dissolved in 0.3 L of tetrahydrofuran (THF) in a 1 L round-bottom flask, and intermediate B-8-2 (28.86 g, 83.95 mmol) and tetrakis(triphenylphosphine)palladium (4.85 g, 4.2 mmol) were added and stirred. Subsequently, a saturated aqueous solution of potassium carbonate (29.01 g, 209.9 mmol) was added, and the mixture was heated to 80 °C and refluxed for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was stirred for 30 minutes. The solid was dissolved in monochlorobenzene at 133 °C, and the solution was filtered through silica gel after removing the water with anhydrous magnesium sulfate. The resulting filtrate was cooled to room temperature and filtered. The obtained solid was purified repeatedly using monochlorobenzene to obtain 31.0 g (67.1%) of compound B-12.

[0460] Synthesis Example 21: Synthesis of Compound B-79

[0461] [Reaction Scheme 23]

[0462]

[0463] a) Synthesis of intermediate product B-79-1

[0464] Intermediate B-79-1 (18 g, 74%) was synthesized according to the same method as in synthesis example 20c) except that 2,4-chloro-6-phenyl-1,3,5-triazine (21 g, 93 mmol) and 4,4,5,5-tetramethyl-2-(4-naphth-2-yl-phenyl)-[1,3,2]dioxane-2-pentaborane (20.5 g, 62 mmol) were used.

[0465] b) Synthesis of compound B-79

[0466] Intermediate B-79-1 (22.5 g, 57.2 mmol) and carbazole (7.9 g, 47.6 mmol) were dissolved in 200 mL of DMF, and NaH was added. The reaction solution was stirred at room temperature for 4 hours, and then added to 500 mL of water to form a precipitate. The solid formed was filtered and washed with water and methanol. The solid was recrystallized from 500 mL of chlorobenzene to obtain 22.8 g (91%) of compound B-79.

[0467] Synthesis Example 22: Synthesis of Compound B-55

[0468] [Reaction Scheme 24]

[0469]

[0470] a) Synthesis of intermediate product B-55-1

[0471] Except for the use of 1-bromo-2-nitrobenzene (35 g, 173.2 mmol) and 1-naphthalene-boronic acid (32.78 g, 190.6 mmol), 28 g (64.8%) of intermediate B-55-1 was synthesized according to the same method as in c) of Synthesis Example 20.

[0472] b) Synthesis of intermediate product B-55-2

[0473] Intermediate B-55-1 (28.0 g, 112 mmol) and triphenylphosphine (88.4 g, 337 mmol) were placed in a round-bottom flask and dissolved in 1,2-dichlorobenzene (300 ml), and then stirred at 180 °C for 24 hours. When the reaction was complete, after removing the solvent, the product was obtained by column chromatography to give 17.7 g (72.5%) of intermediate B-55-2.

[0474] c) Synthesis of intermediate product B-55-3

[0475] Intermediate product B-55-3 was synthesized using the same method as in synthesis example 20c).

[0476] d) Synthesis of compound B-55

[0477] Intermediate product B-55-3 (22 g, 63.9 mmol), intermediate product B-55-2 (13.9 g, 63.9 mmol), sodium tert-butoxide (NaOtBu) (9.2 g, 95.9 mmol), Pd2(dba)3 (3.5 g, 3.8 mmol), and tri-tert-butylphosphine (P(tBu)3) (4.6 g, 50% toluene solution) were placed in xylene (300 mL) and then heated and refluxed under a nitrogen stream for 12 hours. After removing the xylene, 200 mL of methanol was added to the resulting mixture, the crystalline solid was filtered off, dissolved in toluene, and filtered using silica gel / diatomaceous earth. An appropriate amount of organic solvent was concentrated to obtain 21.0 g (62.6%) of compound B-55.

[0478] Synthesis Example 23: Synthesis of Compound B-31

[0479] [Reaction Scheme 25]

[0480]

[0481] a) Synthesis of intermediate product B-31-1

[0482] Except for the use of 22.6 g (100 mmol) of 2,4-dichloro-6-phenyltriazine and 0.9 equivalents of diphenylfuran-3-boronic acid, 21.4 g (60%) of intermediate B-31-1 was synthesized according to the same method as in c) of synthesis example 20.

[0483] b) Synthesis of compound B-31

[0484] Except for the use of intermediate B-31-1 (21.4 g, 59.8 mmol) and 1 equivalent of N-phenyl-carbazole-2-boronic acid, 25 g (74%) of compound B-31 was synthesized according to the same method as in c) of synthetic example 20.

[0485] Synthesis Example 24: Synthesis of Compound B-83

[0486] [Reaction Scheme 26]

[0487]

[0488] a) Synthesis of compound B-83

[0489] Except for the use of intermediate B-83-1 (20 g, 59.3 mmol) and 2-chloro-4-phenyl-6-(4-biphenyl)-1,3,5-triazine (20.39 g, 59.3 mmol), 24 g (67.4%) of compound B-83 was synthesized according to the same method as in c) of synthetic example 20.

[0490] Synthesis Example 25: Synthesis of Compound B-84

[0491] [Reaction Scheme 27]

[0492]

[0493] a) Synthesis of compound B-84

[0494] Except for the use of intermediates B-83-1 (20 g, 59.3 mmol) and B-31-1 (21.22 g, 59.3 mmol), 26 g (71.3%) of compound B-84 was synthesized according to the same method as in c) of synthetic example 20.

[0495] Synthesis Example 26: Synthesis of Compound B-85

[0496] [Reaction Scheme 28]

[0497]

[0498] a) Synthesis of compound B-85

[0499] Except for the use of intermediate B-83-1 (20 g, 59.3 mmol) and 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (20.4 g, 59.3 mmol), 23 g (64.6%) of compound B-85 was synthesized according to the same method as in c) of synthetic example 20.

[0500] (Manufacturing of Organic Light Emitting Diodes)

[0501] Example 1

[0502] Wash with distilled water as A thick film of ITO (indium tin oxide) coated glass substrate was prepared. After rinsing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a plasma cleaner for 10 minutes using oxygen plasma and then transferred to a vacuum depositor. The resulting ITO transparent electrode was used as the anode, and compound A was vacuum-deposited onto the ITO substrate to form... A thick hole injection layer was formed, and compound B was deposited on the injection layer. Thick, then compound C is deposited to A hole transport layer is formed by vacuum deposition of compound C-1. On top of this hole transport layer, a hole transport auxiliary layer is formed by vacuum deposition of compound C-1. A thick luminescent layer. On the hole transport auxiliary layer, 2 wt% [Ir(piq)2acac] was formed by simultaneously using compounds A-93 and B-12 as the host and vacuum-deposited doping as the dopant. A thick luminescent layer. In this paper, compounds A-93 and B-12 are used in a 6:4 weight ratio, and their proportions are provided separately in the following examples. Subsequently, on the luminescent layer, compounds D and Liq were simultaneously vacuum-deposited in a 1:1 ratio to form a thick luminescent layer. A thick electron transport layer, and on the electron transport layer, Liq and Al are sequentially vacuum deposited. Thick and harmonious Thickness, thus manufacturing organic light-emitting diodes.

[0503] Organic light-emitting diodes have five organic thin layers, and specifically, have the following structure.

[0504] ITO / Compound A / Compound B / Compound C / Compound C-1 / EML[Compound A-93:B-12:[Ir(piq)2acac](2wt%)] / Compound D:Liq / Liq / Al

[0505] Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazole-3-yl)biphenyl-4,4'-diamine

[0506] Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexanitrile (HAT-CN)

[0507] Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0508] Compound C-1: N,N-bis([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluorenzo[4,3-b]benzofuran-10-amine

[0509] Compound D: 8-(4-(4,6-bis(naphthyl-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0510] Examples 2 to 10, Comparative Examples 1 and 2

[0511] Except for the changes in composition shown in Table 1, each organic light-emitting diode was produced according to the same method as in Example 1.

[0512] evaluate

[0513] The luminous efficiency of the organic light-emitting diodes according to Examples 1 to 10 and Comparative Examples 1 and 2 was evaluated.

[0514] The specific measurement methods are as follows, and the results are shown in Table 1.

[0515] (1) Measuring current density change based on voltage change

[0516] Using a voltmeter (Keithley 2400), the current flowing into the unit device of the organic light-emitting diode was measured while the voltage was increased from 0V to 10V, and the measured current value was divided by the area to provide the result.

[0517] (2) Measuring brightness changes based on voltage changes

[0518] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a luminance meter (Minolta Cs-1000A).

[0519] (3) Measurement of luminous efficiency

[0520] The same current density (10 mA / cm²) was calculated using the brightness, current density, and voltage (V) from projects (1) and (2). 2 Luminous efficiency (cd / A) at )

[0521] (4) Measurement of lifespan

[0522] In terms of brightness (cd / m 2 Maintained at 9000 cd / m 2 Meanwhile, the results were obtained by measuring the time it took for the luminous efficiency (cd / A) to decrease to 97%.

[0523] (5) Measurement of driving voltage

[0524] Using a voltammeter (Keithley 2400), at 15 mA / cm 2 Measure the drive voltage of each diode.

[0525] [Table 1]

[0526]

[0527] Referring to Table 1, compared with the organic light-emitting diodes according to Comparative Examples 1 and 2, the organic light-emitting diodes according to Examples 1 to 10 show significantly improved driving voltage, efficiency and lifetime.

[0528] Although the invention has been described in conjunction with embodiments which are now considered practical embodiments, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover a variety of changes and equivalent arrangements contained within the spirit and scope of the appended claims.

Claims

1. A compound for use in organic optoelectronic devices, said compound being represented by one of chemical formulas 3A, 3B, 3E, and 3J: [Chemical Formula 3A] [Chemical Formula 3B] [Chemical Formula 3E] [Chemical Formula 3J] In chemical formulas 3A, 3B, 3E, and 3J, L 5 To L 8 All are single keys. L 9 and L 10 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group. Ar is a substituted or unsubstituted C6 to C30 aryl group. R 7 To R 10 R e R f and R g Each is independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group. Z 1 To Z 5 Each is independently N or CL d -R d , Z 1 To Z 5 At least two of them are N. in, L d 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. R d 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, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or combinations thereof, and R d They exist independently, or their adjacent groups are connected to each other to form substituted or unsubstituted aliphatic monocyclic or substituted or unsubstituted aliphatic polycyclic, substituted or unsubstituted aromatic monocyclic or substituted or unsubstituted aromatic polycyclic, or substituted or unsubstituted heteroaromatic monocyclic or substituted or unsubstituted heteroaromatic polycyclic.

2. The compound for organic optoelectronic devices according to claim 1, wherein... Chemical formula 3A is represented by chemical formula 3A-2 or chemical formula 3A-4, and Chemical formula 3E is represented by chemical formula 3E-2: [Chemical Formula 3A-2] [Chemical Formula 3A-4] [Chemical Formula 3E-2] in, In chemical formulas 3A-2, 3A-4, and 3E-2, L 5 To L 10 Ar, R 8 To R 10 R e R f and Z 1 To Z 5 Same as that defined in claim 1.

3. The compound for organic optoelectronic devices according to claim 1, wherein, Group It is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a substituted or unsubstituted naphthidyl group.

4. The compound for organic optoelectronic devices according to claim 1, wherein, Group Represented by one of the following: in, L d1 To L d5 L e1 and L e2 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. R d1 To R d5 R k1 and R k2 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted amino, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl. It is a connection point.

5. The compound for organic optoelectronic devices according to claim 1, wherein, Group It is one of the substituents in group I: [Group I] In group I, It is a connection point.

6. The compound for organic optoelectronic devices according to claim 1, wherein... The compound used in organic optoelectronic devices is represented by one of chemical formulas 3A-2, 3B, 3E-2, and 3J: [Chemical Formula 3A-2] [Chemical Formula 3B] [Chemical Formula 3E-2] [Chemical Formula 3J] in, In chemical formulas 3A-2, 3B, 3E-2, and 3J L 5 To L 8 All are single keys. L 9 and L 10 Each of these can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted naphthylene. Ar is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted fluorenyl. R 7 To R 10 R e R f and R g Each is independently either hydrogen or deuterium. Z 1 To Z 5 Each is independently N or CL d -R d , Z 1 To Z 5 At least two of them are N. Among them, L d Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group. R d Each of these is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. R d They exist independently, or their adjacent groups are connected to each other to form substituted or unsubstituted quinoxalinyl groups, or substituted or unsubstituted quinoxalinyl groups.

7. The compound for organic optoelectronic devices according to claim 1, wherein, The compound is selected from group 2: [Group 2] 。 8. An organic optoelectronic device, comprising: The anode and cathode facing each other, At least one organic layer disposed between the anode and the cathode. in, The organic layer comprises the compound for an organic optoelectronic device as described in any one of claims 1 to 7.

9. The organic optoelectronic device according to claim 8, wherein... The organic layer includes a light-emitting layer, and The light-emitting layer contains the compound used in the organic optoelectronic device.

10. The organic optoelectronic device according to claim 9, wherein, The compound used in organic optoelectronic devices is included as the phosphorescent host of the light-emitting layer.

11. A display device comprising the organic optoelectronic device of claim 8.

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