Compounds for use in organic optoelectronic devices, compositions for use in organic optoelectronic devices, organic optoelectronic devices, and display devices

Abstract

Disclosed are compounds for use in organic optoelectronic devices, compositions for use in organic optoelectronic devices, organic optoelectronic devices, and display devices, wherein the compounds are represented by Chemical Formula 1, and the compositions comprise the compounds. Detailed description of Chemical Formula 1 is as described in the specification.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0196243, filed on December 24, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices are disclosed. Background Technology

[0004] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy into light energy and vice versa.

[0005] Based on their working principles, organic optoelectronic devices can be broadly classified into two categories. One category consists of optoelectronic devices that generate electrical energy by separating excitons formed from light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other category consists of light-emitting devices that generate light energy from electrical energy by providing voltage or current to the electrodes.

[0006] Examples of organic optoelectronic devices include organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0007] Organic light-emitting diodes (OLEDs) have attracted considerable attention in recent years due to the increasing demand for flat panel display devices. 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

[0008] One embodiment provides a compound for organic optoelectronic devices that can reduce driving voltage and enable high-efficiency and long-life organic optoelectronic devices.

[0009] Another embodiment provides a composition for an organic optoelectronic device comprising a compound for an organic optoelectronic device.

[0010] Another embodiment provides an organic optoelectronic device comprising a compound for an organic optoelectronic device or 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, a compound for an organic optoelectronic device, represented by chemical formula 1, is provided.

[0013] [Chemical Formula 1]

[0014] In chemical formula 1, L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 3 and R 1 To R 9 Each of these elements is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted C6 to C30 arylsilyl, or substituted or unsubstituted C6 to C20 aryl. R 1 To R 8 At least one of them is deuterium. m1 is one of the integers from 1 to 3. When m1 is an integer greater than or equal to 2, each R 9 They are the same or different from each other, and Ar 1 To Ar 3 At least one of them is a group represented by chemical formula 2. [Chemical Formula 2]

[0015] In chemical formula 2, R 10 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted C6 to C30 arylsilyl, or substituted or unsubstituted C6 to C20 aryl. m2 is one of the integers from 1 to 4. When m2 is an integer greater than or equal to 2, each R 10 They are the same or different from each other, and It is a connection point.

[0016] According to another embodiment, a composition for an organic optoelectronic device comprising a first compound and a second compound is provided.

[0017] The first compound can be the compound described above for use in organic optoelectronic devices, and the second compound can be represented by chemical formula 3, a combination of chemical formula 4 and chemical formula 5, or chemical formula 6.

[0018] [Chemical Formula 3]

[0019] In chemical formula 3, R 11 To R 15 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. m3, m6, and m7 are each an independent integer from 1 to 4. m4 and m5 are each an independent integer from 1 to 3. When m3 to m7 are 2 or greater, R 11 To R 15 Each is the same as or different from the others, and n is one of the integers from 0 to 2; [Chemical Formula 4] [Chemical Formula 5]

[0020] In chemical formulas 4 and 5, a1 in chemical formula 4 up to a4 In the middle, the two adjacent ones are each connected to chemical formula 5. The carbon (C) that is attached to the carbon, and a1 in chemical formula 4 up to a4 In the formula, the other two not connected to chemical formula 5 are CL. a -R a , L a L 5 and L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a R 16 and R 17 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 6 and Ar 7 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m8 and m9 are each an independent integer from 1 to 4, and When m8 and m9 are 2 or greater, R 16 and R 17 Each is the same as or different from the other; [Chemical Formula 6]

[0021] In chemical formula 6, L 7 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group. R 18 To R 21 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 8 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m10, m12, and m13 are each an independent integer from 1 to 4. m11 is one of the integers from 1 to 3, and When m10 to m13 are 2 or greater, R 18 To R 21 They are the same as or different from each other.

[0022] According to another embodiment, the organic optoelectronic device includes an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, and the organic layer contains a compound for the organic optoelectronic device or a composition for the organic optoelectronic device.

[0023] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0024] It is possible to achieve high efficiency and long lifespan organic optoelectronic devices while reducing operating voltage. Attached Figure Description

[0025] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0026] <Explanation of Figure Markers>

[0027] 100: Organic Light Emitting Diode

[0028] 105: Organic layer

[0029] 110: Cathode

[0030] 120: Anode

[0031] 130: Emissive layer

[0032] 140: Hole transport region

[0033] 150: Electron transport region Detailed Implementation

[0034] Embodiments of the invention are described in detail below. However, these embodiments are exemplary and the present disclosure is not limited thereto.

[0035] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by one of the following: 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.

[0036] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: 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, C2 to C30 heteroaryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, C1 to C20 alkyl, C1 to C5 alkylsilyl, C6 to C20 aryl, C2 to C20 heteroaryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, C1 to C5 alkyl, C1 to C5 alkylsilyl, C6 to C18 aryl, C2 to C18 heteroaryl, or cyano. In specific examples of the present invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by one of the following: deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, phenyl, biphenyl, terphenyl or naphthyl.

[0037] As used in this article, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0038] As used herein, “hydrogen (-H) substituted” may include “deuterium (-D) substituted” or “tritium (-T) substituted”.

[0039] As used herein, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon.

[0040] As used herein, “aryl” means a group comprising at least one aromatic hydrocarbon moiety, and all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., two or more aromatic hydrocarbon moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more aromatic hydrocarbon moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0041] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0042] As used herein, "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 replacing carbon (C) in cyclic compounds 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.

[0043] For example, "heteroaryl" can refer to an aryl group comprising 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 comprises two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0044] 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 trefyl, a substituted or unsubstituted benzo[a]phenanthyl, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is not limited thereto.

[0045] 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, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indoleyl group, or a substituted or unsubstituted... The following are substituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, 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 carbazoyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuran fluorenyl, substituted or unsubstituted benzothiophene fluorenyl, or combinations thereof, but not limited thereto.

[0046] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and holes formed in the anode can be readily injected into and transported in the light-emitting layer due to the conductivity of the highest occupied molecular orbital (HOMO) energy level.

[0047] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into and transported in the light-emitting layer.

[0048] The following describes a compound for an organic optoelectronic device according to one embodiment.

[0049] According to one embodiment, a compound for an organic optoelectronic device is represented by chemical formula 1.

[0050] [Chemical Formula 1]

[0051] In chemical formula 1, L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene. Ar 1 and Ar2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 3 and R 1 To R 9 Each of these elements is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted C6 to C30 arylsilyl, or substituted or unsubstituted C6 to C20 aryl. R 1 To R 8 At least one of them is deuterium. m1 is one of the integers from 1 to 3. When m1 is an integer greater than or equal to 2, each R 9 They are the same or different from each other, and Ar 1 To Ar 3 At least one of them is a group represented by chemical formula 2. [Chemical Formula 2]

[0052] In chemical formula 2, R 10 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted C6 to C30 arylsilyl, or substituted or unsubstituted C6 to C20 aryl. m2 is one of the integers from 1 to 4. When m2 is an integer greater than or equal to 2, each R 10 They are the same or different from each other, and It is a connection point.

[0053] Compounds represented by Formula 1 can achieve high efficiency and long lifetime by substituting the phenylene group linked to the triazine at the ortho position with carbazole to introduce steric hindrance. This steric hindrance induces a small Est and prevents the exciton relaxation route, thereby achieving high efficiency and long lifetime. Furthermore, by substituting the triazine or phenylene group with a CN-substituted phenyl group to achieve fast electron mobility, the device can be operated quickly, and the electronic stability can be greatly improved while maintaining high efficiency, resulting in improved lifetime characteristics.

[0054] In addition, a long lifetime can be achieved by replacing hydrogen with deuterium in the carbazole moiety through the HD isotope effect.

[0055] For example, based on the substitution position of chemical formula 2, chemical formula 1 can be represented by chemical formula 1A or chemical formula 1B.

[0056] [Chemical Formula 1A]

[0057] [Chemical Formula 1B]

[0058] In chemical formula 1A and chemical formula 1B, L 1 L 2 R 1 To R 10 m1 and m2 are the same as above. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 3 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted C6 to C30 arylsilyl, or substituted or unsubstituted C6 to C20 aryl.

[0059] As a specific example, chemical formula 1A can be represented by any one of chemical formulas 1A-1 to 1A-3.

[0060] [Chemical Formula 1A-1]

[0061] [Chemical Formula 1A-2]

[0062] [Chemical Formula 1A-3]

[0063] In chemical formulas 1A-1 to 1A-3, Ar 2 Ar 3 L 1 L 2 R 1 To R 10 m1 and m2 are the same as above.

[0064] As a specific example, chemical formula 1B can be represented by any one of chemical formulas 1B-1 to 1B-3.

[0065] [Chemical Formula 1B-1]

[0066] [Chemical Formula 1B-2]

[0067] [Chemical Formula 1B-3]

[0068] In chemical formulas 1B-1 to 1B-3 Ar 1 Ar 2 L 1 L 2 R 1 To R 10 m1 and m2 are the same as above.

[0069] For example, chemical formula 1B-1 can be represented by any one of chemical formula 1B-1-(i), chemical formula 1B-1-(ii), chemical formula 1B-1-(iii), and chemical formula 1B-1-(iv).

[0070] For example, chemical formula 1B-2 can be represented by any one of chemical formula 1B-2-(i), chemical formula 1B-2-(ii), chemical formula 1B-2-(iii), and chemical formula 1B-2-(iv).

[0071] For example, chemical formula 1B-3 can be represented by any one of chemical formula 1B-3-(i), chemical formula 1B-3-(ii), chemical formula 1B-3-(iii), and chemical formula 1B-3-(iv).

[0072] [Chemical formula 1B-1-(i)]

[0073] [Chemical formula 1B-1-(ii)]

[0074] [Chemical formula 1B-1-(iii)]

[0075] [Chemical formula 1B-1-(iv)]

[0076] [Chemical formula 1B-2-(i)]

[0077] [Chemical formula 1B-2-(ii)]

[0078] [Chemical formula 1B-2-(iii)]

[0079] [Chemical formula 1B-2-(iv)]

[0080] [Chemical formula 1B-3-(i)]

[0081] [Chemical formula 1B-3-(ii)]

[0082] [Chemical formula 1B-3-(iii)]

[0083] [Chemical formula 1B-3-(iv)]

[0084] In the chemical formulas 1B-1-(i), 1B-1-(ii), 1B-1-(iii), 1B-1-(iv), 1B-2-(i), 1B-2-(ii), 1B-2-(iii), 1B-2-(iv), 1B-3-(i), 1B-3-(ii), 1B-3-(iii), and 1B-3-(iv), Ar 1 Ar 2 L 1 L 2 R 1 To R 10 m1 and m2 are the same as above.

[0085] In one embodiment, the compound used in the organic optoelectronic device may be represented by chemical formula 1A-1 or chemical formula 1B-1.

[0086] In specific embodiments, the compound used in organic optoelectronic devices may be represented by any one of the following chemical formulas: 1A-1, 1B-1-(ii), 1B-1-(iii), and 1B-1-(iv).

[0087] For example, Ar 1 and Ar 2 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0088] For example, Ar3 It can be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0089] For example, L 1 and L 2 Each can be a single bond or a substituted or unsubstituted phenylene group, and each can be independent of the others.

[0090] For example, R 1 To R 10 Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted tert-butyl, substituted or unsubstituted trimethylsilyl, or substituted or unsubstituted phenyl.

[0091] For example, R 1 To R 4 At least one of them can be deuterium.

[0092] As another example, R 5 To R 8 At least one of them can be deuterium.

[0093] As another example, R 1 To R 4 At least one of them and R 5 To R 8 At least one of them can be deuterium.

[0094] As another example, R 1 To R 4 At least two of them and R 5 To R 8 At least two of them can be deuterium.

[0095] As another example, R 1 To R 4 At least three of them and R 5 To R 8 At least three of them can be deuterium.

[0096] As another example, R 1 To R 8 Each can be deuterium.

[0097] In the most specific embodiment, the compound represented by chemical formula 1 may be selected from, but is not limited to, one of the compounds listed in group 1.

[0098] [Group 1]

[0099] According to another embodiment, the composition for an organic optoelectronic device comprises a first compound and a second compound, wherein the first compound is the compound described above for an organic optoelectronic device, and the second compound may be represented by chemical formula 3, a combination of chemical formula 4 and chemical formula 5, or chemical formula 6.

[0100] [Chemical Formula 3]

[0101] In chemical formula 3, R 11 To R 15 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. m3, m6, and m7 are each an independent integer from 1 to 4. m4 and m5 are each an independent integer from 1 to 3, and n is one of the integers from 0 to 2; [Chemical Formula 4] [Chemical Formula 5]

[0102] In chemical formulas 4 and 5, a1 in chemical formula 4 up to a4 In the middle, the two adjacent ones are each connected to chemical formula 5. The connecting carbon (C). a1 in chemical formula 4 up to a4 In the formula, the other two not connected to chemical formula 5 are CL. a -R a , L a L 5 and L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a R 16 and R 17Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 6 and Ar 7 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m8 and m9 are each an independent integer from 1 to 4; [Chemical Formula 6]

[0103] In chemical formula 6, L 7 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group. R 18 To R 21 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 8 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m10, m12, and m13 are each independently one of the integers from 1 to 4, and m11 is one of the integers from 1 to 3.

[0104] The second compound can be used together with the first compound in the luminescent layer to improve luminous efficiency and lifetime characteristics by increasing charge mobility and enhancing stability.

[0105] In chemical formula 3, when m3 is 2 or greater, each R 11 They can be the same or different from each other. In chemical formula 3, when m4 is 2 or greater, each R 12 They can be the same or different from each other. In chemical formula 3, when m5 is 2 or greater, each R 13 They can be the same or different from each other. In chemical formula 3, when m6 is 2 or greater, each R 14 They can be the same or different from each other. In chemical formula 3, when m7 is 2 or greater, each R 15 They can be the same or different from each other. In chemical formulas 4 and 5, when m8 is 2 or greater, each R 16 They can be the same as or different from each other.

[0106] In chemical formulas 4 and 5, when m9 is 2 or greater, each R 17 They can be the same or different from each other. In chemical formula 6, when m10 is 2 or greater, each R 18 They can be the same or different from each other. In chemical formula 6, when m11 is 2 or greater, each R 19 They can be the same or different from each other. In chemical formula 6, when m12 is 2 or greater, each R 20 They can be the same as or different from each other, and In chemical formula 6, when m13 is 2 or greater, each R 21 They can be the same as or different from each other.

[0107] For example, in chemical formula 3, Ar 4 and Ar 5 Each of these can be 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 anthraquinone, a substituted or unsubstituted triphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted fluorenyl. In chemical formula 3, L 3 and L 4 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene (biphenylene group). In chemical formula 3, R 11 To R 15 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and n can be 0 or 1.

[0108] For example, in Formula 3, "substituted" means that at least one hydrogen atom is substituted by a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0109] For example, in chemical formula 3, Ar 4 and Ar 5 Each can be independently a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted fluorenyl.

[0110] In a specific embodiment of the present invention, chemical formula 3 may be represented by one of chemical formulas 3-1 to 3-15.

[0111] [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3]

[0112] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6]

[0113] [Chemical Formula 3-7] [Chemical Formula 3-8] [Chemical Formula 3-9]

[0114] [Chemical Formula 3-10] [Chemical Formula 3-11] [Chemical Formula 3-12]

[0115] [Chemical Formula 3-13] [Chemical Formula 3-14] [Chemical Formula 3-15]

[0116] In chemical formulas 3-1 to 3-15, R 11 To R 15 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 3 -Ar 4 and L 4 -Ar 5 Each can be one of the substituents listed in Group I, independently.

[0117] [Group I]

[0118] In group I, R 21 To R 26 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m14 is one of the integers from 1 to 5. m15 is one of the integers from 1 to 4. m16 is one of the integers from 1 to 3. m17 is an integer of 1 or 2. m18 is one of the integers from 1 to 7. It is a connection point.

[0119] In group I, when m14 is 2 or greater, each R 22 They can be the same as or different from each other.

[0120] In group I, when m15 is 2 or greater, each R 23 They can be the same as or different from each other.

[0121] In group I, when m16 is 2 or greater, each R 24 They can be the same as or different from each other.

[0122] In group I, when m17 is 2, each R 25 They can be the same as or different from each other.

[0123] In group I, when m18 is 2 or greater, each R 26 They can be the same as or different from each other.

[0124] The combination of chemical formula 4 and chemical formula 5 can be represented, for example, by one of chemical formula 4A, chemical formula 4B, chemical formula 4C, chemical formula 4D, and chemical formula 4E.

[0125] [Chemical Formula 4A] [Chemical Formula 4B] [Chemical Formula 4C]

[0126] [Chemical Formula 4D] [Chemical Formula 4E]

[0127] In chemical formulas 4A to 4E, L 5 L 6 Ar 6 Ar 7 R 16 R 17 The same applies to m8 and m9. L a1 To L a4 As mentioned above, L 5 and L 6 Defined, and R a1 To R a4 As mentioned above, R 16 and R 17 Defined.

[0128] For example, in chemical formulas 4 and 5, Ar 6 and Ar 7 Each of these can be 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 anthraquinone, a substituted or unsubstituted triphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted fluorenyl. R a1 To R a4R 16 and R 17 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0129] In a specific embodiment of the present invention, in chemical formulas 4 and 5, L 5 -Ar 6 and L 6 -Ar 7 Each can be independently selected from the substituents listed in Group I.

[0130] In one implementation, R a1 To R a4 R 16 and R 17 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0131] For example, R a1 To R a4 R 16 and R 17 Each can be independently hydrogen, deuterium, cyano, or a substituted or unsubstituted phenyl group, and

[0132] In a specific implementation, R a1 To R a4 R 16 and R 17 Each can be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, independently.

[0133] Chemical formula 6 can be represented, for example, by any one of chemical formulas 6-1 to 6-4.

[0134] [Chemical Formula 6-1] [Chemical Formula 6-2]

[0135] [Chemical Formula 6-3] [Chemical Formula 6-4]

[0136] In chemical formulas 6-1 to 6-4, L 7 Ar 8 R 18 To R 21 The same applies to m10 to m13 as described above.

[0137] For example, in chemical formula 6, Ar 8 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted triphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted fluorene.

[0138] R 18 To R 21 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0139] In a specific embodiment of the present invention, in chemical formula 6, L 7 -Ar 8 Substituents can be selected from those listed in Group I.

[0140] For example, R 18 To R 21 Each can be an independent group of hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups.

[0141] Chemical formula 3 can be represented by chemical formula 3-8, and in chemical formula 3-8, Ar 4 and Ar 5 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene, L 3 and L 4 Each can be a single bond or a substituted or unsubstituted C6 to C20 aryl group, and R 11 To R 14 Each of these can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0142] For example, in chemical formula 3-8, R 11 To R 14 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 3 -Ar 4 and L 4 -Ar 5 Each can be one of the substituents listed in Group I, independently.

[0143] In another specific embodiment of the invention, the second compound may be represented by chemical formula 4C, and in chemical formula 4C, L a3 and L a4 It can be a single key, L 5 and L 6 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, R 16 R 17 R a3 and R a4 Each of them can be hydrogen, deuterium, or phenyl, Ar 6 and Ar 7 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0144] For example, in the chemical formula 4C, L a3 and L a4 It can be a single key, R 16 R 17 R a3 and R a4 Each can be independently hydrogen, deuterium, or C6 to C12 aryl, and L 5 -Ar 6 and L 6 -Ar 7 Each can be one of the substituents listed in Group I, independently.

[0145] For example, the second compound used in an organic optoelectronic device may be selected from, but is not limited to, one of the compounds listed in Group 2.

[0146] [Group 2]

[0147] [B-1] [B-2] [B-3] [B-4] [B-5]

[0148] [B-6] [B-7] [B-8] [B-9] [B-10]

[0149] [B-11] [B-12] [B-13] [B-14] [B-15]

[0150] [B-16] [B-17] [B-18] [B-19] [B-20]

[0151] [B-21] [B-22] [B-23] [B-24] [B-25]

[0152] [B-26] [B-27] [B-28] [B-29] [B-30]

[0153] [B-31] [B-32] [B-33] [B-34] [B-35]

[0154] [B-36] [B-37] [B-38] [B-39] [B-40]

[0155] [B-41] [B-42] [B-43] [B-44] [B-45]

[0156] [B-46] [B-47] [B-48] [B-49] [B-50]

[0157] [B-51] [B-52] [B-53] [B-54] [B-55]

[0158] [B-56] [B-57] [B-58] [B-59] [B-60]

[0159] [B-61] [B-62] [B-63] [B-64] [B-65]

[0160] [B-66] [B-67] [B-68] [B-69] [B-70]

[0161] [B-71] [B-72] [B-73] [B-74] [B-75]

[0162] [B-76] [B-77] [B-78] [B-79] [B-80]

[0163] [B-81] [B-82] [B-83] [B-84] [B-85]

[0164] [B-86] [B-87] [B-88] [B-89] [B-90]

[0165] [B-91] [B-92] [B-93] [B-94] [B-95]

[0166] [B-96] [B-97] [B-98] [B-99] [B-100]

[0167] [B-101] [B-102] [B-103] [B-104] [B-105]

[0168] [B-106] [B-107] [B-108] [B-109] [B-110]

[0169] [B-111] [B-112] [B-113] [B-114] [B-115]

[0170] [B-116] [B-117] [B-118] [B-119] [B-120]

[0171] [B-121] [B-122] [B-123] [B-124] [B-125]

[0172] [B-126] [B-127] [B-128] [B-129] [B-130]

[0173] [B-131] [B-132] [B-133] [B-134] [B-135]

[0174] [B-136] [B-137] [B-138]

[0175] [B-139] [B-140] [B-141] [B-142]

[0176] [B-143] [B-144] [B-145]

[0177] [B-146] [B-147] [B-148] [B-149]

[0178] [B-150]

[0179] Additionally, examples are shown below of at least one hydrogen atom in compounds B-1 to B-150 listed in Group 2 being replaced by deuterium, but this disclosure is not limited thereto.

[0180] [B-151] [B-152] [B-153] [B-154] [B-155]

[0181] [B-156] [B-157] [B-158] [B-159] [B-160]

[0182] [B-161] [B-162] [B-163] [B-164] [B-165]

[0183] [B-166] [B-167] [B-168] [B-169] [B-170]

[0184] [B-171] [B-172] [B-173] [B-174] [B-175]

[0185] [B-176] [B-177] [B-178] [B-179] [B-180]

[0186] [B-181] [B-182] [B-183] [B-184] [B-185]

[0187] [B-186] [B-187] [B-188] [B-189] [B-190]

[0188] [B-191] [B-192] [B-193] [B-194] [B-195]

[0189] (Dn refers to the number of deuterium atoms substituted and represents the structure substituted by one or more deuterium atoms.)

[0190] The most specific structures of compounds B-151 to B-195 of Group 2 are presented below as examples based on the position and degree of deuterium substitution, which does not limit the scope of the claims of the compounds not shown below.

[0191] When deuterium is substituted, it is not limited to the compounds in the examples below, and the position of the deuterium substitution and the degree of substitution can include all variable ranges from compound B-1 to compound B-195.

[0192] [B-196] [B-197] [B-198]

[0193] [B-199] [B-200] [B-201] [B-202]

[0194] [B-203] [B-204] [B-205] [B-206]

[0195] [B-207] [B-208] [B-209] [B-210]

[0196] [B-211] [B-212] [B-213] [B-214]

[0197] [B-215] [B-216] [B-217]

[0198] [B-218] [B-219] [B-220] [B-221]

[0199] [B-222] [B-223] [B-224] [B-225]

[0200] [B-226] [B-227] [B-228] [B-229]

[0201] [B-230] [B-231] [B-232] [B-233]

[0202] [B-234]

[0203] [C-1] [C-2] [C-3] [C-4]

[0204] [C-5] [C-6] [C-7] [C-8]

[0205] [C-9] [C-10] [C-11] [C-12]

[0206] [C-13] [C-14] [C-15] [C-16]

[0207] [C-17] [C-18] [C-19] [C-20]

[0208] [C-21] [C-22] [C-23] [C-24]

[0209] [C-25] [C-26] [C-27] [C-28]

[0210] [C-29] [C-30] [C-31] [C-32]

[0211] [C-33] [C-34] [C-35] [C-36]

[0212] [C-37] [C-38] [C-39] [C-40]

[0213] [C-41] [C-42] [C-43] [C-44]

[0214] [C-45] [C-46] [C-47] [C-48]

[0215] [C-49] [C-50] [C-51] [C-52]

[0216] [C-53] [C-54] [C-55] [C-56]

[0217] [C-57]

[0218] Additionally, examples are shown below of at least one hydrogen atom in compounds C-1 to C-57 listed in Group 2 being replaced by deuterium, but this disclosure is not limited thereto.

[0219] [C-58] [C-59] [C-60] [C-61] [C-62]

[0220] [C-63] [C-64] [C-65] [C-66] [C-67]

[0221] [C-68] [C-69] [C-70] [C-71] [C-72]

[0222] (Dn refers to the number of deuterium atoms substituted and represents the structure substituted by one or more deuterium atoms.)

[0223] The most specific structures of compounds C-58 to C-72 of Group 2 are presented below as examples based on the position and degree of deuterium substitution, which does not limit the scope of the claims of the compounds not shown below.

[0224] When deuterium is substituted, it is not limited to the compounds in the examples below, and the position of the deuterium substitution and the degree of substitution can include all variable ranges from compound C-1 to compound C-72.

[0225] [C-73] [C-74]

[0226] [C-75] [C-76] [C-77] [C-78]

[0227] [C-79] [C-80] [C-81] [C-82]

[0228] [C-83] [C-84] [C-85] [C-86]

[0229] [C-87] [C-88] [C-89] [C-90]

[0230] [C-91] [C-92] [C-93] [C-94]

[0231] [C-95] [C-96] [C-97] [C-98]

[0232] [C-99] [C-100] [C-101] [C-102]

[0233] [D-1] [D-2] [D-3] [D-4] [D-5]

[0234] [D-6] [D-7] [D-8] [D-9] [D-10]

[0235] [D-11] [D-12] [D-13] [D-14] [D-15]

[0236] [D-16] [D-17] [D-18] [D-19] [D-20]

[0237] [D-21] [D-22] [D-23] [D-24] [D-25]

[0238] [D-26] [D-27] [D-28] [D-29] [D-30]

[0239] [D-31] [D-32] [D-33] [D-34] [D-35]

[0240] [D-36] [D-37] [D-38] [D-39] [D-40]

[0241] [D-41] [D-24] [D-43] [D-44] [D-45]

[0242] [D-46] [D-47] [D-48] [D-49] [D-50]

[0243] [D-51] [D-52] [D-53] [D-54] [D-55]

[0244] [D-56] [D-57] [D-58] [D-59] [D-60]

[0245] Additionally, examples are shown below of at least one hydrogen atom in compounds D-1 to D-60 listed in Group 2 being replaced by deuterium, but this disclosure is not limited thereto.

[0246] [D-61] [D-62] [D-63] [D-64] [D-65]

[0247] [D-66] [D-67] [D-68] [D-69] [D-70]

[0248] [D-71] [D-72] [D-73] [D-74] [D-75]

[0249] [D-76] [D-77] [D-78] [D-79] [D-80]

[0250] [D-81] [D-82] [D-83] [D-84] [D-85]

[0251] [D-86] [D-87] [D-88] [D-89] [D-90]

[0252] [D-91] [D-92] [D-93] [D-94] [D-95]

[0253] [D-96] [D-97] [D-98] [D-99] [D-100]

[0254] [D-101] [D-102] [D-103] [D-104] [D-105]

[0255] [D-106] [D-107] [D-108] [D-109] [D-110]

[0256] [D-111] [D-112] [D-113] [D-114] [D-115]

[0257] [D-116] [D-117] [D-118] [D-119] [D-120]

[0258] (Dn refers to the number of deuterium atoms substituted and represents the structure substituted by one or more deuterium atoms.)

[0259] For example, the first compound and the second compound may be contained in a weight ratio of 1:99 to 99:1. Within this range, the electron transport capability of the first compound and the hole transport capability of the second compound can be used to adjust the desired weight ratio to achieve bipolar characteristics, thereby improving efficiency and lifetime. Within the aforementioned range, for example, they may be contained in weight ratios of about 10:90 to 90:10, about 20:80 to 80:20 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40). As specific examples, they may be contained in weight ratios of 40:60, 50:50, or 60:40.

[0260] The following describes an organic optoelectronic device comprising the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device.

[0261] Organic optoelectronic devices can be suitable devices that convert electrical energy into light energy and vice versa, such as organic photoelectric devices, organic light-emitting diodes, organic solar cells, or organic photosensitive drums.

[0262] 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.

[0263] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0264] 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.

[0265] 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 poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0266] 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 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, and BaF2 / Ca, but is not limited thereto.

[0267] The organic layer 105 may contain the above-described compounds for organic optoelectronic devices or compositions for organic optoelectronic devices.

[0268] The organic layer 105 may include a light-emitting layer 130, which may include a host and a dopant. The host may include the compounds or compositions described above for organic optoelectronic devices, and the dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant.

[0269] A dopant is a material that is mixed in small amounts with a compound or composition used in organic optoelectronic devices 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 more states. Dopants can be, for example, inorganic, organic, or organic-inorganic compounds, and one or more of these types can be used.

[0270] 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.

[0271] [Chemical Formula Z]

[0272] L 8 MX 1

[0273] In the chemical formula Z, M is a metal, and L 8 and X 1 The same or different ligands that form a complex with M.

[0274] 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 8 and X 1 It could be, for example, a bidentate ligand.

[0275] By L 8 and X 1 The ligand represented can be selected from one of the chemical formulas Z-1 to Z-8.

[0276] [Chemical Formula Z-1] [Chemical Formula Z-2] [Chemical Formula Z-3]

[0277] [Chemical Formula Z-4] [Chemical Formula Z-5]

[0278] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0279] [Chemical Formula Z-8]

[0280] In chemical formulas Z-1 to Z-8 X 14 Selected from carbon and nitrogen, Y 100 Is it O or S? R 101 To R 122 Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 133 R 134 R 135 Or -GeR 133 R 134 R 135Alternatively, it can be attached to an adjacent substituent to form a substituted or unsubstituted ring, and for example, together with pyridine to form a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuranopyridine, a substituted or unsubstituted benzothiophenopyridine, a substituted or unsubstituted indenepyridine, a substituted or unsubstituted benzofuranoquinoline, a substituted or unsubstituted benzothiophenoquinoline, or a substituted or unsubstituted indenequinoline; R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. m111 is an integer of 1 or 2. m18 is one of the integers from 1 to 4, and m19 is one of the integers from 1 to 5.

[0281] By L 8 and X 1 Examples of ligands may be selected from, but are not limited to, the chemical formulas listed in group A.

[0282] [Group A]

[0283] In group A, 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 R 303 To R 308 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. m25 is one of the integers from 1 to 5. m26 is one of the integers from 1 to 4. m27 is one of the integers from 1 to 3. m28 is an integer of 1 or 2. m29 is one of the integers from 1 to 6, and When m25 to m27 and m29 are 2 or greater and m28 is 2, R 303 To R 307 They are the same as or different from each other.

[0284] According to one embodiment, the dopant may be an iridium complex and may be represented, for example, by one of chemical formulas 7 to 9.

[0285] [Chemical Formula 7]

[0286] In chemical formula 7, Ring A is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused ring systems, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring. R 100 Indicates one to a maximum number of monovalent substituents. When R 100 When there are 2 or more, each R 100 Whether they are the same or different, R 101 To R 104 Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. X 10 and X 11 Each is independently selected from carbon and nitrogen. L 100 It is a ligand or bidentate ligand of a monovalent anion, which coordinates to iridium via a non-shared electron pair of carbon or heteroatom, and m21 is any integer from 0 to 3.

[0287] [Chemical Formula 8]

[0288] In chemical formula 8, Ring B is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused ring systems, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring. Y 100 Is it O or S? R 201Indicates one to a maximum number of monovalent substituents. When R 201 When there are 2 or more, each R 201 Whether they are the same or different, R 206 To R 213 Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. X 12 and X 13 Each is independently selected from carbon and nitrogen. L 100 It is a ligand or bidentate ligand of a monovalent anion, which coordinates to iridium via non-shared electron pairs of carbon or heteroatoms. m100 is one of the integers from 1 to 3. m101 is an integer of 1 or 2. n100 is an integer that is either 0 or 1, and m21 is any integer from 0 to 3.

[0289] [Chemical Formula 9]

[0290] In chemical formula 9, Y 100 Is it O or S? R 101 To R 111 Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a ligand or bidentate ligand of a monovalent anion, which coordinates to iridium via a non-shared electron pair of carbon or heteroatom, and m21 is any integer from 0 to 3.

[0291] As a more specific example, iridium complexes can be represented by one of chemical formulas 7-1 to 7-6.

[0292] [Chemical Formula 7-1]

[0293] In chemical formula 7-1, R 101 To R 116 Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 132 R 133 R 134 Or -GeR 132 R 133 R 134 , R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 101 To R 116 At least one of them is a functional group represented by the chemical formula V-1. L 100 It is a bidentate ligand for a monovalent anion, and is a ligand coordinated to iridium via a lone pair of electrons from a carbon or heteroatom. m21 and m22 are each independent integers from 0 to 3, and m21 + m22 is an integer from 1 to 3. [Chemical Formula V-1]

[0294] In chemical formula V-1, R 135 To R 139 Each of these elements 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 This indicates the portion that is attached to a carbon atom.

[0295] [Chemical Formula 7-2]

[0296] [Chemical Formula 7-3]

[0297] [Chemical Formula 7-4]

[0298] [Chemical Formula 7-5]

[0299] [Chemical Formula 7-6]

[0300] In chemical formulas 7-2 to 7-6 X 14 Selected from carbon and nitrogen, Y 100 Is it O or S? R 101 To R 122 Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 133 R 134 R 135 Or -GeR 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a bidentate ligand for monovalent anions, and is a ligand coordinated to iridium via a lone pair of electrons from a carbon or heteroatom. m111 is an integer of 1 or 2, and n1 and n2 are independent integers from 0 to 3, and n1 + n2 is an integer from 1 to 3. In another embodiment, the dopant may be a platinum complex, such as a platinum complex represented by the chemical formula Z-1.

[0301] [Chemical Formula Z-1]

[0302] In chemical formula Z-1, rings A, B, C, and D are each independently a 5- or 6-membered carbon ring or a heterocycle; R A R B R C and R D Each can be independently mono-, di-, tri-, or tetra-substituted or unsubstituted; nA is an integer that is either 0 or 1; L B L C and L DEach of these can be independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof. When nA is 1, L E It can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof; and when nA is 0, L E It does not exist; R A R B R C R D R and R' are each independently 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, or 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.

[0303] Platinum complexes can be represented, for example, by chemical formula 8-1 or chemical formula 8-2.

[0304] [Chemical Formula 8-1]

[0305] [Chemical Formula 8-2]

[0306] In chemical formulas 8-1 and 8-2, X 100 Selected from O, S and NR 132 , R 118 To R 132 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 , R133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 118 To R 132 At least one of them is -SiR 133 R 134 R 135 Or tert-butyl, and R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0307] In addition to the light-emitting layer, the organic layer may also include charge transport regions.

[0308] The charge transport region can be, for example, the hole transport region 140.

[0309] The hole transport region 140 can further improve hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0310] Specifically, the hole transport region 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 hole transport layer and the hole transport auxiliary layer may contain at least one of the compounds listed in Group B.

[0311] [Group B]

[0312] (Dn refers to the number of deuterium atoms substituted and represents the structure substituted by one or more deuterium atoms.)

[0313] In the hole transport region 140, in addition to the compounds mentioned above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and compounds with similar structures may also be used.

[0314] Alternatively, the charge transport region can be, for example, the electron transport region 150.

[0315] The electron transport region 150 can also improve electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0316] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light-emitting layer 130 and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the electron transport layer and the electron transport auxiliary layer may contain at least one compound of group C.

[0317] [Group C]

[0318] One implementation may be an organic light-emitting diode that includes a light-emitting layer as an organic layer.

[0319] Another implementation could be an organic light-emitting diode (OLED) that includes an emitting layer and a hole transport region as organic layers.

[0320] Another implementation could be an organic light-emitting diode (OLED) that includes an emitting layer and an electron transport region as organic layers.

[0321] In addition to the light-emitting layer 130, an organic light-emitting diode according to one embodiment also includes a hole transport region 140 and an electron transport region 150 as an organic layer 105, such as Figure 1 As shown.

[0322] On the other hand, in addition to the light-emitting layer, organic light-emitting diodes can also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as organic layers.

[0323] An organic light-emitting diode 100 can be manufactured by forming an anode or cathode on a substrate, then forming an organic layer by a dry film method (such as vacuum deposition, sputtering, plasma electroplating and ion electroplating), and forming a cathode or anode thereon.

[0324] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0325] 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.

[0326] In the following examples and synthesis examples, the starting materials and reactants used were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P & H Tech, or synthesized by known methods, unless otherwise specified.

[0327] (Synthesis of compounds for organic optoelectronic devices)

[0328] Synthesis Example 1: Synthesis of Compound A-1

[0329] [Reaction Formula 1]

[0330] Step 1: Synthesis of intermediate P-2

[0331] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (50 g / 1.0 eq.), (3-bromo-2-fluorophenyl)boronic acid (1.2 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 45 g of intermediate P-2.

[0332] Step 2: Synthesis of intermediate P-1

[0333] Intermediate P-2 (45 g / 1.0 eq.), (2-benzonitrile)boric acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 32 g of intermediate P-1.

[0334] Step 3: Synthesis of compound A-1

[0335] Intermediate P-1 (10 g / 1.0 eq.), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask along with DMF (200 mL), and the mixture was refluxed at 150°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 8 g of compound A-1.

[0336] Synthesis Example 2: Synthesis of Compound A-2

[0337] [Reaction 2]

[0338] Step 1: Synthesis of intermediate P-4

[0339] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (50 g / 1.0 eq.), (4-chloro-2-fluorophenyl)boronic acid (1.2 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 45 g of intermediate P-4.

[0340] Step 2: Synthesis of intermediate P-3

[0341] Intermediate P-4 (45 g / 1.0 eq.), (2-benzonitrile)boric acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 30 g of intermediate P-3.

[0342] Step 3: Synthesis of compound A-2

[0343] Intermediate P-3 (10 g / 1.0 eq.), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (200 mL), and the mixture was refluxed at 150°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 7 g of compound A-2.

[0344] Synthesis Example 3: Synthesis of Compound A-3

[0345] [Reaction 3]

[0346] Step 1: Synthesis of intermediate P-6

[0347] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (50 g / 1.0 eq.), (5-chloro-2-fluorophenyl)boronic acid (1.2 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 41 g of intermediate P-6.

[0348] Step 2: Synthesis of intermediate P-5

[0349] Intermediate P-6 (41 g / 1.0 eq.), (2-benzonitrile)boric acid (1.1 eq.), Pd(PPh3)4 (0.05 eq.), and K2CO3 (3.0 eq.) were added to a flask along with THF (750 mL) and distilled water (250 mL), and then refluxed at 80°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 25 g of intermediate P-5.

[0350] Step 3: Synthesis of compound A-3

[0351] Intermediate P-5 (10 g / 1.0 eq.), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask along with DMF (200 mL), and the mixture was refluxed at 150°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 6 g of compound A-3.

[0352] Synthesis Example 4: Synthesis of Compound R-1

[0353] [Reaction 4]

[0354] Intermediate P-1 (10 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (200 mL), and the mixture was refluxed at 150°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 7 g of compound R-1.

[0355] Synthesis Example 5: Synthesis of Compound R-2

[0356] [Reaction 5]

[0357] Intermediate P-3 (10 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (200 mL), and the mixture was refluxed at 150°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 7 g of compound R-2.

[0358] Synthesis Example 6: Synthesis of Compound R-3

[0359] [Reaction Formula 6]

[0360] Intermediate P-5 (10 g / 1.0 eq.), 9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (200 mL), and the mixture was refluxed at 150°C. After 12 hours, the reaction was terminated, and the resulting product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, column chromatography was performed to obtain 6 g of compound R-3.

[0361] Synthesis Example 7: Synthesis of Compound C-4

[0362] [Reaction Formula 7]

[0363] 10.0 g (24.5 mmol) of intermediate 9-1, 6.3 g (26.9 mmol) of intermediate 9-2, 1.1 g (1.2 mmol) of Pd2(dba)3, 3.5 g (36.7 mmol) of NaOtBu, and 0.7 g (3.7 mmol) of P(t-Bu)3 were added to a round-bottom flask, along with 122 mL of xylene. The mixture was then stirred and refluxed at 140°C for 12 hours. When the reaction was complete, distilled water was added, and the mixture was stirred. The resulting organic layer was removed by silica gel filtration and recrystallized to obtain 10.3 g (75%) of compound C-4.

[0364] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.54 g / mol)

[0365] Synthesis Example 8: Synthesis of Compound B-136

[0366] Compound B-136 was obtained by purchasing it from GemChem, Inc.

[0367] HRMS (70eV, EI+): Theoretical m / z value of C42H28N2: 560.2252, experimental value: 560.

[0368] Elemental analysis: C, 90%; H, 5%

[0369] Example 1: Fabrication of a green organic light-emitting diode (single substrate)

[0370] The ITO (indium tin oxide) coated glass substrate was cleaned with distilled water and ultrasonically. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then moved to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being moved to a vacuum depositor. Using the obtained ITO transparent electrode as the anode, compound A (available from Novaled) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer, and compound A was deposited on the hole injection layer to form a 1350 Å thick hole transport layer. Compound B was deposited on the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound A-1 was used as the host and doped with 7 wt% PhGD as a dopant to form a 400 Å thick light-emitting layer by vacuum deposition. Then, compound C was deposited on the light-emitting layer to form a 50 Å thick electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum-deposited in a 1:1 weight ratio to form a 300 Å thick electron transport layer. LiQ (15 Å) and Al (1200 Å) were then vacuum-deposited sequentially on the electron transport layer to form a cathode, thereby fabricating an organic light-emitting diode.

[0371] The organic light-emitting diode has the following structure: ITO / compound A (3% NDP-9 doped, 100 Å) / compound A (1350 Å) / compound B (350 Å) / EML [body (compound A-1): PhGD = 93 wt% : 7 wt%] (400 Å) / compound C (50 Å) / compound D: LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0372] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0373] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluorene-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0374] Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1'':3'',1''':3''',1'''-pentaphenyl]-3''''-yl)-1,3,5-triazine

[0375] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluorene-4-yl)-6-phenyl-1,3,5-triazine

[0376] [PhGD]

[0377] Examples 2 and 3 and Comparative Examples 1 to 3

[0378] Organic light-emitting diodes were manufactured in the same manner as in Example 1, except that the composition was changed to those shown in Table 1.

[0379] Example 4: Fabrication of Green Organic Light Emitting Diode (Hybrid Body)

[0380] The ITO (indium tin oxide) coated glass substrate was cleaned with distilled water and ultrasonically. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then moved to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being moved to a vacuum depositor. Using the obtained ITO transparent electrode as the anode, compound E (available from NovEled) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer, and compound E was deposited on the hole injection layer to form a 1350 Å thick hole transport layer. Compound F was deposited on the hole transport layer to a thickness of 320 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compounds A-1 and C-4 in a weight ratio of 4:6 were used as the host, and 10 wt% PhGD was doped as a dopant to form a 380 Å thick light-emitting layer by vacuum deposition. Next, compound G was deposited on the light-emitting layer to form a 50 Å thick electron transport auxiliary layer, and compounds H and LiQ were simultaneously vacuum-deposited in a 1:1 weight ratio to form a 300 Å thick electron transport layer. On the electron transport layer, LiQ and Al were sequentially vacuum-deposited to thicknesses of 15 Å and 1200 Å, respectively, to fabricate an organic light-emitting diode.

[0381] The organic light-emitting diode has the following structure: ITO / compound E (3% NDP-9 doped, (100 Å)) / compound E (1350 Å) / compound F (320 Å) / EML [body (compound A-1 : compound C-4 = 4 : 6 wt% / wt%) : PhGD = 90 wt% : 10 wt%] (380 Å) / compound G (50 Å) / compound H : LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å).

[0382] Compound E: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0383] Compound F: 9,9-Dimethyl-N-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluorene-2-amine

[0384] Compound G: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0385] Compound H: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthyl-2-yl}-4,6-diphenyl-1,3,5-triazine)

[0386] Examples 5 to 6 and Comparative Examples 4 to 6

[0387] Organic light-emitting diodes were manufactured in the same manner as in Example 4, except that the composition was changed to those shown in Table 2.

[0388] evaluate

[0389] The lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 6 and Comparative Examples 1 to 6 were evaluated.

[0390] The specific measurement methods are shown below, and the results are presented in Tables 1 and 2.

[0391] (1) Measure the change in current density based on the voltage change

[0392] While increasing the voltage from 0 V to 10 V, the current flowing through the unit diode in the obtained organic light-emitting diode was measured using a current-voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0393] (2) Measure the change in brightness based on voltage changes

[0394] The luminance was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0 V to 10 V.

[0395] (3) Measure the current efficiency

[0396] Using the luminance and current density and voltage measured by (1) and (2) above, calculate the same current density (10 mA / cm²). 2 Current efficiency (cd / A) at ).

[0397] (4) Measuring lifespan

[0398] In terms of brightness (cd / m 2 Maintain at 24000 cd / m 2At the same time, the time it takes for the current efficiency (cd / A) to drop to 97% is measured as the lifetime.

[0399] The lifetime measurements of Examples 1 to 3 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1.

[0400] The lifetime measurements of Examples 4 to 6 and Comparative Examples 4 to 6 were calculated based on the relative values ​​of Comparative Example 4 and are listed in Table 2.

[0401] (Table 1)

[0402] (Table 2)

[0403] Referring to Tables 1 and 2, it can be confirmed that, compared with the organic light-emitting diodes according to Comparative Examples 1 to 6, the lifetime of the organic light-emitting diodes according to Examples 1 to 6 is significantly improved in all cases where deuterium is substituted in carbazole. This is due to the thermal and chemical stability of deuterium towards holes and electrons compared to hydrogen, which is an isotope effect.

[0404] Although the invention has been described in conjunction with exemplary embodiments which are now considered to be practical, 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 compound for use in organic optoelectronic devices, said compound being represented by chemical formula 1: [Chemical Formula 1] In chemical formula 1, L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene. Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. Ar 3 and R 1 To R 9 Each of these elements is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted C6 to C30 arylsilyl, or substituted or unsubstituted C6 to C20 aryl. R 1 To R 8 At least one of them is deuterium. m1 is one of the integers from 1 to 3. When m1 is an integer greater than or equal to 2, each R 9 They are the same or different from each other, and Ar 1 To Ar 3 At least one of them is a group represented by chemical formula 2. [Chemical Formula 2] In chemical formula 2, R 10 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, substituted or unsubstituted C6 to C30 arylsilyl, or substituted or unsubstituted C6 to C20 aryl. m2 is one of the integers from 1 to 4. When m2 is an integer greater than or equal to 2, each R 10 They are the same or different from each other, and It is a connection point.

2. The compound for organic optoelectronic devices according to claim 1, wherein, Chemical formula 1 can be represented by either chemical formula 1A or chemical formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] In chemical formula 1A and chemical formula 1B, Ar 1 To Ar 3 L 1 L 2 R 1 To R 10 m1 and m2 are as defined in claim 1.

3. The compound for organic optoelectronic devices according to claim 2, wherein, Chemical formula 1A can be represented by any one of chemical formulas 1A-1 to 1A-3: [Chemical Formula 1A-1] [Chemical Formula 1A-2] [Chemical Formula 1A-3] In chemical formulas 1A-1 to 1A-3, Ar 2 Ar 3 L 1 L 2 R 1 To R 10 m1 and m2 are as defined in claim 2.

4. The compound for organic optoelectronic devices according to claim 2, wherein, Chemical formula 1B can be represented by any one of chemical formulas 1B-1 to 1B-3: [Chemical Formula 1B-1] [Chemical Formula 1B-2] [Chemical Formula 1B-3] In chemical formulas 1B-1 to 1B-3 Ar 1 Ar 2 L 1 L 2 R 1 To R 10 m1 and m2 are as defined in claim 2.

5. The compound for organic optoelectronic devices according to claim 4, wherein, Chemical formula 1B-1 is represented by any one of chemical formula 1B-1-(ii), chemical formula 1B-1-(iii), and chemical formula 1B-1-(iv): [Chemical formula 1B-1-(ii)] [Chemical formula 1B-1-(iii)] [Chemical formula 1B-1-(iv)] In chemical formulas 1B-1-(ii), 1B-1-(iii), and 1B-1-(iv), Ar 1 Ar 2 L 1 L 2 R 1 To R 10 m1 and m2 are as defined in claim 4.

6. A compound for use in an organic optoelectronic device, said compound being selected from the compounds listed in Group 1: [Group 1] 。 7. A composition for use in an organic optoelectronic device, comprising: First compound and second compound, in, The first compound is the compound for organic optoelectronic devices as described in claim 1, and The second compound is represented by chemical formula 3, a combination of chemical formulas 4 and 5, or chemical formula 6: [Chemical Formula 3] In chemical formula 3, R 11 To R 15 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 4 and Ar 5 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. m3, m6, and m7 are each an independent integer from 1 to 4. m4 and m5 are each an independent integer from 1 to 3. When m3 to m7 are 2 or greater, R 11 To R 15 Each is the same as or different from the others, and n is one of the integers from 0 to 2; [Chemical Formula 4][Chemical Formula 5] In chemical formulas 4 and 5, a1 in chemical formula 4 up to a4 In the middle, the two adjacent ones are each connected to chemical formula 5. The connecting carbon, a1 in chemical formula 4 up to a4 In the formula, the other two not connected to chemical formula 5 are CL. a -R a , L a L 5 and L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group. R a R 16 and R 17 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 6 and Ar 7 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m8 and m9 are each an independent integer from 1 to 4, and When m8 and m9 are 2 or greater, R 16 and R 17 Each is the same as or different from the other; [Chemical Formula 6] In chemical formula 6, L 7 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group. R 18 To R 21 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. Ar 8 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m10, m12, and m13 are each an independent integer from 1 to 4. m11 is one of the integers from 1 to 3. When m10 to m13 are 2 or greater, R 18 To R 21 They are the same as or different from each other.

8. The composition for an organic optoelectronic device according to claim 7, wherein, Chemical formula 3 is represented by chemical formula 3-8: [Chemical Formula 3-8] In chemical formula 3-8, R 11 To R 14 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m3 and m6 are each an independent integer from 1 to 4. m4 and m5 are each an independent integer from 1 to 3, and L 3 -Ar 4 and L 4 -Ar 5 Each is independently one of the substituents listed in Group I. [Group I] In group I, R 21 To R 26 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m14 is one of the integers from 1 to 5. m15 is one of the integers from 1 to 4. m16 is one of the integers from 1 to 3. m17 is an integer of 1 or 2. m18 is one of the integers from 1 to 7, and It is a connection point.

9. The composition for an organic optoelectronic device according to claim 7, wherein, The combination of chemical formulas 4 and 5 is represented by chemical formula 4C: [Chemical formula 4C] In the chemical formula 4C, L a3 and L a4 It's a single key. R 16 R 17 R a3 and R a4 Each is independently hydrogen, deuterium, or C6 to C12 aryl. m8 and m9 are each an independent integer from 1 to 4, and L 5 -Ar 6 and L 6 -Ar 7 Each is independently one of the substituents listed in Group I. [Group I] In group I, R 21 To R 26 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m14 is one of the integers from 1 to 5. m15 is one of the integers from 1 to 4. m16 is one of the integers from 1 to 3. m17 is an integer of 1 or 2. m18 is one of the integers from 1 to 7, and It is a connection point.

10. An organic optoelectronic device, comprising: The anode and cathode facing each other, and At least one organic layer between the anode and the cathode, Wherein, the organic layer comprises The compound for an organic optoelectronic device according to any one of claims 1 to 6; or The composition for an organic optoelectronic device according to any one of claims 7 to 9.

11. The organic optoelectronic device according to claim 10, wherein, The organic layer includes a light-emitting layer, and The light-emitting layer comprises either the compound for organic optoelectronic devices or the composition for organic optoelectronic devices.

12. A display device comprising the organic optoelectronic device of claim 10 or claim 11.

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