Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device

Abstract

Provided are a compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device including the compound, an organic optoelectronic device, and a display device. The chemical formula 1 is as defined in the specification.

Description

[0001] CITATION OF RELATED APPLICATION

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0106354, filed on August 8, 2024, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference. TECHNICAL FIELD

[0003] Disclosed are a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. BACKGROUND

[0004] An organic optoelectronic device (organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0005] Depending on the working principle, organic optoelectronic devices can be roughly classified into two categories. One is a photovoltaic device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, and the other is a light-emitting device that generates light energy from electrical energy by supplying a voltage or a current to an electrode.

[0006] Examples of the organic optoelectronic device include an organic photovoltaic device, an organic light-emitting diode, an organic solar cell, and an organic photosensitive drum.

[0007] Among them, an organic light-emitting diode (OLED) has attracted much attention in recent years due to an increasing demand for flat panel display devices. The organic light-emitting diode is a device that converts electrical energy into light, and the performance of the organic light-emitting diode is greatly influenced by an organic material between electrodes. SUMMARY

[0008] One embodiment provides a compound for an organic optoelectronic device, which can reduce a driving voltage and achieve an organic optoelectronic device with high efficiency and long lifespan.

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

[0010] Another embodiment provides an organic optoelectronic device including a compound for an organic optoelectronic device or a composition for an organic optoelectronic device.

[0011] Another embodiment provides a display device including 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]

[0015] In chemical formula 1,

[0016] R 1 To R 4 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C18 aryl.

[0017] 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.

[0018] m1, m3, and m4 are each an independent integer from 1 to 4.

[0019] m2 is one of the integers from 1 to 3, and

[0020] When m1 to m4 are each 2 or greater, R 1 To R 4 They are the same as or different from each other.

[0021] According to another embodiment, a composition for an organic optoelectronic device comprising a first compound and a second compound is provided.

[0022] 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 2, a combination of chemical formula 3 and chemical formula 4, or chemical formula 5.

[0023] [Chemical Formula 2]

[0024]

[0025] In chemical formula 2,

[0026] R 5 To R 9 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.

[0027] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0028] L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0029] m5, m8, and m9 are each an independent integer from 1 to 4.

[0030] m6 and m7 are each an independent integer from 1 to 3.

[0031] When m5 to m9 are 2 or greater, R 5 To R 9 Each is the same as or different from the others, and

[0032] n is one of the integers from 0 to 2;

[0033]

[0034] In chemical formulas 3 and 4,

[0035] In chemical formula 3, a1* to a4*, each of the two adjacent ones is a linking carbon (C) connected to * in chemical formula 4.

[0036] Of a1* to a4* in chemical formula 3, the other two not connected to chemical formula 4 are CL. a -R a L a L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0037] R a R 10 and R 11 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.

[0038] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0039] m10 and m11 are each an independent integer from 1 to 4, and

[0040] When m10 and m11 are 2 or greater, R 10 and R 11 Each is the same as or different from the other;

[0041] [Chemical Formula 5]

[0042]

[0043] In chemical formula 5,

[0044] L 5 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group.

[0045] R 12 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.

[0046] Ar 7 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0047] m12, m14, and m15 are each an independent integer from 1 to 4.

[0048] m13 is one of the integers from 1 to 3, and

[0049] When m12 to m15 are 2 or greater, R 12 To R 15 They are the same as or different from each other.

[0050] 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, wherein the organic layer contains the aforementioned compound for an organic optoelectronic device or composition for an organic optoelectronic device.

[0051] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0052] It is possible to achieve high efficiency and long lifespan organic optoelectronic devices while reducing operating voltage. Attached Figure Description

[0053] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0054] <Explanation of Figure Markers>

[0055] 100: Organic Light Emitting Diode

[0056] 105: Organic layer

[0057] 110: Cathode

[0058] 120: Anode

[0059] 130: Emissive layer

[0060] 140: Hole transport region

[0061] 150: Electron transport region Detailed Implementation

[0062] Embodiments of the invention are described in detail below. However, these embodiments are exemplary and the present disclosure is not limited thereto.

[0063] 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.

[0064] 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.

[0065] In this specification, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0066] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0067] In this specification, 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.

[0068] In this specification, "aryl" means a group comprising at least one aromatic hydrocarbon moiety, wherein all elements of the aromatic hydrocarbon moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., and 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.

[0069] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0070] 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 in place of 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.

[0071] 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.

[0072] 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.

[0073] 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 or substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthophenyl, substituted or unsubstituted benzofuran fluorenyl, substituted or unsubstituted benzothiophenenyl or combinations thereof, but not limited thereto.

[0074] As used herein, hole properties 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 emissive layer due to the conductivity of the highest occupied molecular orbital (HOMO) energy level.

[0075] 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.

[0076] The following describes a compound for an organic optoelectronic device according to one embodiment.

[0077] According to one embodiment, a compound for an organic optoelectronic device is represented by chemical formula 1.

[0078] [Chemical Formula 1]

[0079]

[0080] In chemical formula 1,

[0081] R 1 To R 4Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C18 aryl.

[0082] 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.

[0083] m1, m3, and m4 are each an independent integer from 1 to 4.

[0084] m2 is one of the integers from 1 to 3, and

[0085] When m1 to m4 are 2 or greater, R 1 To R 4 They are the same as or different from each other.

[0086] The compound represented by Formula 1 has a structure containing a CN-substituted phenyl group in addition to a carbazole substituted with a triazine, and improves the stability of the hole-containing portion to electrons, thereby enabling organic light-emitting diodes containing the compound to achieve significantly improved lifetime characteristics while maintaining high efficiency.

[0087] In chemical formula 1, when m1 is 2 or greater, each R 1 They can be the same or different from each other.

[0088] In chemical formula 1, when m2 is 2 or greater, each R 2 They can be the same or different from each other.

[0089] In chemical formula 1, when m3 is 2 or greater, each R 3 They can be the same as or different from each other, and

[0090] In chemical formula 1, when m4 is 2 or greater, each R 4 They can be the same as or different from each other.

[0091] For example, based on the linkage position of the phenylene-linked triazine and carbazole, chemical formula 1 can be derived from chemical...

[0092] Any one of Formula 1A to Formula 1C.

[0093]

[0094] [Chemical Formula 1C]

[0095]

[0096] In chemical formulas 1A to 1C

[0097] R 1To R 4 Ar 1 Ar 2 The definitions of m1 to m4 are as described above.

[0098] As a specific example, in which the substitution positions of CN are more specifically restricted, chemical formula 1 can be from chemical formula 1A-1 to chemical formula 1A-3, chemical formula 1B-1 to chemical formula 1B-3, and chemical formula 1A-1 to chemical formula 1B-3.

[0099] Any one of the following representations: Formula 1C-1 to Formula 1C-3.

[0100]

[0101] [Chemical Formula 1A-3]

[0102]

[0103] [Chemical Formula 1B-3]

[0104]

[0105] [Chemical formula 1C-3]

[0106]

[0107] In chemical formulas 1A-1 to 1A-3, 1B-1 to 1B-3, and 1C-1 to 1C-3

[0108] R 1 To R 4 Ar 1 Ar 2 The definitions of m1 to m4 are the same as those above.

[0109] As a more specific example, chemical formula 1 can be represented by chemical formula 1A-1 in which CN is substituted at the ortho position.

[0110] In one embodiment, chemical formula 1A-1 can be represented by any one of chemical formulas 1A-1-I to 1A-1-IV.

[0111]

[0112]

[0113] In chemical formulas 1A-1-I to 1A-1-IV

[0114] R 1 To R 4 Ar 1 Ar 2The definitions of m1 to m4 are the same as those above.

[0115] Specifically, when CN is substituted at the ortho position relative to the phenyl group substituted in carbazole, unlike at the meta and para positions, it does not significantly affect the HOMO and LUMO energy levels. This maintains a shallow LUMO energy level while preserving high efficiency and improves the electronic stability of the hole characteristic unit, thus enabling long-lifetime devices.

[0116] For example, Ar 1 and Ar 2 They can be substituted or unsubstituted C6 to C12 aryl groups, substituted or unsubstituted dibenzofuranyl groups, or substituted or unsubstituted dibenzothiophene groups, each independently.

[0117] As a specific example, Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0118] For example, R 1 To R 4 Each can be hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl or substituted or unsubstituted C6 to C12 aryl, independently.

[0119] As a specific example, R 1 To R 4 Each can be hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl, independently.

[0120] In a 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.

[0121] [Group 1]

[0122]

[0123]

[0124]

[0125] According to another embodiment, a composition for an organic optoelectronic device comprises a first compound and a second compound, wherein the first compound may be the compound described above for an organic optoelectronic device, and the second compound may be represented by chemical formula 2, a combination of chemical formula 3 and chemical formula 4, or chemical formula 5.

[0126] [Chemical Formula 2]

[0127]

[0128] In chemical formula 2,

[0129] R 5 To R 9 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.

[0130] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0131] L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0132] m5, m8, and m9 are each an independent integer from 1 to 4.

[0133] m6 and m7 are each an independent integer from 1 to 3.

[0134] When m5 to m9 are 2 or greater, R 5 To R 9 Each is the same as or different from the others, and

[0135] n is one of the integers from 0 to 2;

[0136]

[0137]

[0138] In chemical formulas 3 and 4

[0139] In chemical formula 3, a1* to a4*, each of the two adjacent ones is a linking carbon (C) connected to * in chemical formula 4.

[0140] Of a1* to a4* in chemical formula 3, the other two not connected to chemical formula 4 are CL. a -R a L a L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0141] R a R 10 and R 11Each 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.

[0142] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0143] m10 and m11 are each an independent integer from 1 to 4, and

[0144] When m10 and m11 are 2 or greater, R 10 and R 11 Each is the same as or different from the other;

[0145] [Chemical Formula 5]

[0146]

[0147] In chemical formula 5,

[0148] L 5 It is a single-bonded or substituted or unsubstituted C6 to C20 arylene group.

[0149] R 12 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.

[0150] Ar 7 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0151] m12, m14, and m15 are each an independent integer from 1 to 4.

[0152] m13 is one of the integers from 1 to 3, and

[0153] When m12 to m15 are 2 or greater, R 12 To R 15 They are the same as or different from each other.

[0154] 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 stability.

[0155] In chemical formula 2, when m5 is 2 or greater, each R 5 They can be the same or different from each other.

[0156] In chemical formula 2, when m6 is 2 or greater, each R 6 They can be the same or different from each other.

[0157] In chemical formula 2, when m7 is 2 or greater, each R 7 They can be the same or different from each other.

[0158] In chemical formula 2, when m8 is 2 or greater, each R 8 They can be the same or different from each other.

[0159] In chemical formula 2, when m9 is 2 or greater, each R 9 They can be the same or different from each other.

[0160] In chemical formulas 3 and 4, when m10 is 2 or greater, each R 10 Whether they are the same or different,

[0161] In chemical formulas 3 and 4, when m11 is 2 or greater, each R 11 Whether they are the same or different,

[0162] In chemical formula 5, when m12 is 2 or greater, each R 12 Whether they are the same or different,

[0163] In chemical formula 5, when m13 is 2 or greater, each R 13 Whether they are the same or different,

[0164] In chemical formula 5, when m14 is 2 or greater, each R 14 They are the same or different from each other, and

[0165] In chemical formula 5, when m15 is 2 or greater, each R 15 They are the same or different from each other.

[0166] For example, in chemical formula 2, Ar 3 and Ar 4 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.

[0167] In chemical formula 2, L 1 and L 2 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0168] In chemical formula 2, R 5 To R 9 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0169] n can be 0 or 1.

[0170] As an example, in Formula 2, "substituted" means that at least one hydrogen atom is replaced by a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0171] For example, in chemical formula 2, Ar 3 and Ar 4 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.

[0172] In a specific embodiment of the present invention, chemical formula 2 can be represented by any one of chemical formulas 2-1 to 2-15.

[0173]

[0174]

[0175] In chemical formulas 2-1 to 2-15, R 5 To R 9 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 1 -Ar 3 and L 2 -Ar 4 Each can be one of the substituents listed in Group I, independently.

[0176] [Group I]

[0177]

[0178] In group I,

[0179] R 19 To R 23 Each is independently hydrogen, deuterium, cyano, C1 to C10 alkyl, or C6 to C12 aryl.

[0180] m19 is one of the integers from 1 to 5.

[0181] m20 is one of the integers from 1 to 4.

[0182] m21 is one of the integers from 1 to 3.

[0183] m22 is an integer of 1 or 2.

[0184] m23 is one of the integers from 1 to 7, and

[0185] * indicates a connection point.

[0186] In group I, when m19 is 2 or greater, each R 19 They can be the same as or different from each other.

[0187] In group I, when m20 is 2 or greater, each R 20 They can be the same as or different from each other.

[0188] In group I, when m21 is 2 or greater, each R 21 They can be the same as or different from each other.

[0189] In group I, when m22 is 2, each R 22 They can be the same as or different from each other.

[0190] In group I, when m23 is 2 or greater, each R 23 They can be the same as or different from each other.

[0191] Combinations of chemical formulas 3 and 4 can be, for example, derived from chemical formulas 3A, 3B, and 4.

[0192] Any one of the following: Formula 3C, Formula 3D, and Formula 3E.

[0193]

[0194]

[0195] In chemical formulas 3A to 3E, L 3 L 4 Ar 5 Ar 6 R 10 R 11 m10 and m11 are the same as above.

[0196] L a1 To L a4 With L 3 and L 4 The definitions are the same, and

[0197] R a1 To R a4 With R 10 and R 11 The definitions are the same.

[0198] For example, in chemical formulas 3 and 4, Ar 5 and Ar 6Each 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.

[0199] R a1 To R a4 R 10 and R 11 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.

[0200] In a specific embodiment of the present invention, in chemical formulas 3 and 4, L 3 -Ar 5 and L 4 -Ar 6 Each can be independently selected from the substituents listed in Group I.

[0201] In one implementation, R a1 To R a4 R 10 and R 11 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.

[0202] For example, R a1 To R a4 R 10 and R 11 Each can be independently hydrogen, deuterium, cyano, or a substituted or unsubstituted phenyl group, and

[0203] In a specific implementation, R a1 To R a4 R 10 and R 11 Each is independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0204] Chemical formula 5 can be represented, for example, by any one of chemical formulas 5-1 to 5-4.

[0205]

[0206] In chemical formulas 5-1 to 5-4, L 5 Ar7 R 12 To R 15 The same applies to m12 to m15 as described above.

[0207] For example, in chemical formula 5, Ar 7 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.

[0208] R 12 To R 15 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.

[0209] In a specific embodiment of the present invention, in chemical formula 5, L 5 -Ar 7 It can be one of the substituents listed in group I.

[0210] For example, R 12 To R 15 Each can be an independent group of hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl groups.

[0211] The second compound can be represented by chemical formula 2-8, and in chemical formula 2-8, Ar 3 and Ar 4 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 1 and L 2 Each can be a single bond or a substituted or unsubstituted C6 to C20 aryl group, and R 5 To R 8 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.

[0212] For example, in chemical formula 2-8, R 5 To R 8 Each can be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 1-Ar 3 and L 2 -Ar 4 Each can be one of the substituents listed in Group I, independently.

[0213] In a specific embodiment of the present invention, the second compound may be represented by the chemical formula 3C, and in the chemical formula 3C, L a3 and L a4 It can be a single key, L 3 and L 4 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, R 10 R 11 R a3 and R a4 Each can be hydrogen, deuterium, or phenyl, and Ar 5 and Ar 6 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.

[0214] For example, in the chemical formula 3C, L a3 and L a4 It can be a single key, R 10 R 11 R a3 and R a4 Each can be independently hydrogen, deuterium, or C6 to C12 aryl, and L 3 -Ar 5 and L 4 -Ar 6 Each can be one of the substituents listed in Group I, independently.

[0215] 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.

[0216] [Group 2]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224] In addition, examples are given below of at least one hydrogen atom in compounds B-1 to B-150 listed in Group 2, but are not limited thereto.

[0225]

[0226]

[0227] (Dn refers to the number of deuterium substitutions and represents the structure substituted by one or more deuteriums)

[0228] The most specific structures of compounds B-151 to B-195 of Group 2 are presented below as examples based on the position and rate of deuterium substitution, and are not intended to limit the scope of claims for compounds not listed below.

[0229] When deuterium is substituted, the compounds are not limited to the examples below, and the deuterium substitution position, deuterium substitution rate, etc. can include all variable ranges from compound B-1 to compound B-195.

[0230]

[0231]

[0232]

[0233] [B-234]

[0234]

[0235]

[0236]

[0237]

[0238] [C-57]

[0239]

[0240] In addition, examples of compounds C-1 to C-57 listed in Group 2 in which at least one hydrogen atom is substituted with deuterium are given below, but not limited thereto.

[0241]

[0242]

[0243] (Dn refers to the number of deuterium substitutions and represents the structure substituted by one or more deuteriums)

[0244] The most specific structures of compounds C-58 to C-72 of Group 2 are presented below as examples based on the position and rate of deuterium substitution, and are not intended to limit the scope of rights of compounds not listed below.

[0245] When deuterium is substituted, it is not limited to the compounds in the examples below, and the deuterium substitution position, deuterium substitution rate, etc. can include all variable ranges from compound C-58 to compound C-72.

[0246]

[0247]

[0248]

[0249]

[0250]

[0251] In addition, examples of compounds D-1 to D-60 listed in Group 2 in which at least one hydrogen atom is substituted with deuterium are given below, but are not limited thereto.

[0252]

[0253]

[0254]

[0255] (Dn refers to the number of deuterium substitutions and represents the structure substituted by one or more deuteriums)

[0256] The first and second compounds can be contained in a weight ratio of, for example, 1:99 to 99:1. Within this range, bipolar characteristics can be achieved by adjusting the appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound, thereby improving efficiency and lifetime. Within this range, they can be contained in weight ratios of, for example, about 10:90 to 90:10, about 20:80 to 80:20, for example, 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 can be contained in weight ratios of 40:60, 50:50, or 60:40.

[0257] In the following text, an organic optoelectronic device comprising the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device will be described.

[0258] 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.

[0259] 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.

[0260] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0261] 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.

[0262] 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.

[0263] The cathode 110 may be made of a conductor with a small work function to aid electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; multilayer materials such as LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto.

[0264] The organic layer 105 may contain the compounds or compositions described above for organic optoelectronic devices.

[0265] The organic layer 105 includes a light-emitting layer 130, and the light-emitting layer 130 includes a host and a dopant. The host may contain the above-described compound for organic optoelectronic devices or composition for organic optoelectronic devices, and the dopant may be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0266] 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.

[0267] 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.

[0268] [Chemical Formula Z]

[0269] L 6 MX 1

[0270] In the chemical formula Z, M is a metal, and L 6 and X 1 The same or different ligands that form a complex with M.

[0271] 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 6 and X 1 It could be, for example, a bidentate ligand.

[0272] By L 6 and X 1 The ligand represented can be selected from one of the chemical formulas Z-1 to Z-2.

[0273] [Chemical Formula Z-1]

[0274]

[0275] [Chemical formula Z-2]

[0276]

[0277] In chemical formulas Z-1 and Z-2,

[0278] Ring A and ring B are each independently monocyclic or polycyclic fused rings.

[0279] In both monocyclic and polycyclic fused ring systems, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring.

[0280] R 200 and R 201 Each independently represents 1 to the maximum number of monovalent substituents.

[0281] When R 200 and R 201 When there are 2 or more, each R 200 and R 201 Same or different,

[0282] R 202 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 214 R 215 R 216 -GeR 214 R 215 R 216 Or a combination of them,

[0283] R 214 To R 216 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0284] X 10 X 11 X 12 and X 13 Each is independently selected from carbon and nitrogen.

[0285] Y 100 Is it O or S?

[0286] m100 is an integer from 1 to 2.

[0287] m101 is an integer from 1 to 2.

[0288] n100 is an integer that is either 0 or 1, and

[0289] * indicates a connection point.

[0290] When n100 is 0, a monovalent substituent is formed, and

[0291] When n100 is 1, a fused ring can be formed.

[0292] By L 6 and X 1 Examples of ligands may be selected from, but are not limited to, the chemical formulas listed in group A.

[0293] [Group A]

[0294]

[0295] In group A,

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

[0297] R 303 To R 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.

[0298] m25 is one of the integers from 1 to 5.

[0299] m26 is one of the integers from 1 to 4.

[0300] m27 is one of the integers from 1 to 3.

[0301] m28 is an integer of 1 or 2.

[0302] m29 is one of the integers from 1 to 6, and

[0303] 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.

[0304] In one embodiment, the dopant may be an iridium complex and may be represented by one of chemical formulas 6-1 to 6-5.

[0305] [Chemical Formula 6-1]

[0306]

[0307] In chemical formula 6-1,

[0308] 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 R134 ,

[0309] R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0310] R 101 To R 116 At least one of them is a functional group represented by the chemical formula V-1.

[0311] L 100 It is a bidentate ligand of a monovalent anion and a ligand coordinated to iridium via a lone pair of electrons from a carbon or heteroatom.

[0312] m21 and m22 are each independent integers from 0 to 3, and m21+m22 is an integer from 1 to 3.

[0313] [Chemical Formula V-1]

[0314]

[0315] In chemical formula V-1,

[0316] R 135 To R 139 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,and

[0317] * indicates a portion connected to a carbon atom.

[0318] [Chemical Formula 6-2]

[0319]

[0320] [Chemical Formula 6-3]

[0321]

[0322] [Chemical Formula 6-4]

[0323]

[0324] [Chemical Formula 6-5]

[0325]

[0326] In chemical formulas 6-2 to 6-5

[0327] X 14 Selected from carbon and nitrogen,

[0328] Y 100 Is it O or S?

[0329] 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.

[0330] L 100 It is a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through the lone pair of electrons of a carbon or heteroatom.

[0331] m111 is an integer from 1 to 2, and

[0332] n1 and n2 are each an integer from 0 to 3, and n1+n2 is an integer from 1 to 3.

[0333] In another embodiment, the dopant may be a platinum complex, such as a platinum complex represented by the chemical formula Z-1.

[0334] [Chemical Formula Z-1]

[0335]

[0336] In chemical formula Z-1, rings A, B, C, and D are each independently a 5- or 6-membered carbon ring or a heterocycle;

[0337] R A R B R C and R D Each can be independently mono-, di-, tri-, or tetra-substituted or unsubstituted;

[0338] nA is an integer that is either 0 or 1;

[0339] L B L C and L D Each 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.

[0340] When nA is 1, L EIt 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;

[0341] 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.

[0342] Platinum complexes can be represented, for example, by chemical formula 7-1 or chemical formula 7-2.

[0343] [Chemical Formula 7-1]

[0344]

[0345] [Chemical Formula 7-2]

[0346]

[0347] In chemical formulas 7-1 and 7-2,

[0348] X 100 Selected from O, S and NR 132 ,

[0349] R 118 To R 132 Each of these elements 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 ,

[0350] Among them, R 133 To R135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group, and

[0351] R 118 To R 132 At least one of them is -SiR 133 R 134 R 135 Or tert-butyl,

[0352] Among them, R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0353] In addition to the light-emitting layer, the organic layer may also include charge transport regions.

[0354] The charge transport region can be, for example, the hole transport region 140.

[0355] The hole transport region 140 can further increase hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0356] 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 of group B.

[0357] [Group B]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364] (Dn refers to the number of deuterium substitutions and represents the structure substituted by one or more deuteriums)

[0365] 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.

[0366] In addition, the charge transport region can be, for example, the electron transport region 150.

[0367] The electron transport region 150 can further increase electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0368] 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.

[0369] [Group C]

[0370]

[0371]

[0372]

[0373]

[0374] One implementation may be an organic light-emitting diode that includes a light-emitting layer as an organic layer.

[0375] Another implementation could be an organic light-emitting diode (OLED) that includes an emitting layer and a hole transport region as organic layers.

[0376] Another implementation could be an organic light-emitting diode (OLED) that includes an emitting layer and an electron transport region as organic layers.

[0377] Another embodiment of the present invention can provide an organic light-emitting diode that, in addition to the light-emitting layer 130, also includes a hole transport region 140 and an electron transport region 150 as an organic layer 105, such as... Figure 1 As shown.

[0378] On the other hand, in addition to the light-emitting layer, an organic light-emitting diode may also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as organic layers.

[0379] 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.

[0380] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0381] In the following description, implementation methods are illustrated in more detail with reference to embodiments. However, these embodiments are exemplary, and the scope of the invention is not limited thereto.

[0382] 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.

[0383] (Synthesis of compounds for organic optoelectronic devices)

[0384] Synthesis Example 1: Synthesis of Compound A-10

[0385] [Reaction Formula 1]

[0386]

[0387] Step 1: Synthesis of Intermediate P-1

[0388] 2-Bromo-9H-carbazole (50 g / 1.0 eq.), (2-cyanophenyl)boronic 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 refluxed at 80 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 41 g of intermediate P-1 was obtained by column chromatography.

[0389] Step 2: Synthesis of Compound A-10

[0390] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (20 g / 1.0 eq.), intermediate P-1 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL) and refluxed at 150 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. Subsequently, 12 g of compound A-10 was obtained by column chromatography.

[0391] Synthesis Example 2: Synthesis of Compound A-13

[0392] [Reaction 2]

[0393]

[0394] Step 1: Synthesis of Intermediate P-2

[0395] 3-Bromo-9H-carbazole (50 g / 1.0 eq.), (2-cyanophenyl)boronic 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. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 32 g of intermediate P-2 was obtained by column chromatography.

[0396] Step 2: Synthesis of Compound A-13

[0397] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (20 g / 1.0 eq.), intermediate P-2 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL) and refluxed at 150 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 10 g of compound A-13 was obtained by column chromatography.

[0398] Synthesis Example 3: Synthesis of Compound A-16

[0399] [Reaction 3]

[0400]

[0401] Step 1: Synthesis of Intermediate P-3

[0402] 4-Bromo-9H-carbazole (70 g / 1.0 eq.), (2-cyanophenyl)boronic 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 refluxed at 80 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 43 g of intermediate P-3 was obtained by column chromatography.

[0403] Step 2: Synthesis of Compound A-16

[0404] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (20 g / 1.0 eq.), intermediate P-3 (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL) and refluxed at 150 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 13 g of compound A-16 was obtained by column chromatography.

[0405] Synthesis Example 4: Synthesis of Compound C-4

[0406] [Reaction 4]

[0407]

[0408] 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 aqueous layer was removed by silica gel filtration, and the resulting organic layer was recrystallized to obtain 10.3 g (75%) of compound C-4.

[0409] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.54 g / mol)

[0410] Synthesis Example 5: Synthesis of Compound B-136

[0411]

[0412] Compound B-136 was obtained by purchasing it from Gemchem.

[0413] HRMS (70eV, EI+): Theoretical m / z value of C42H28N2: 560.2252, experimental value: 560.

[0414] Elemental analysis: C, 90%; H, 5%

[0415] Synthesis Example 6: Synthesis of Compound R-1

[0416] [Reaction 5]

[0417]

[0418] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (20 g / 1.0 eq.), 2-phenyl-9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL) and refluxed at 150 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 10 g of compound R-1 was obtained by column chromatography.

[0419] Synthesis Example 7: Synthesis of Compound R-2

[0420] [Reaction Formula 6]

[0421]

[0422] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (20 g / 1.0 eq.), 3-phenyl-9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL) and refluxed at 150 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 12 g of compound R-2 was obtained by column chromatography.

[0423] Synthesis Example 8: Synthesis of Compound R-3

[0424] [Reaction Formula 6]

[0425]

[0426] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (20 g / 1.0 eq.), 4-phenyl-9H-carbazole (1.5 eq.), and K3PO4 (3.0 eq.) were added to a flask with DMF (400 mL) and refluxed at 150 °C. The reaction was complete after 12 hours. The product was diluted with DCM, washed three times with brine, and dried over MgSO4. 11 g of compound R-3 was obtained by column chromatography.

[0427] Example 1: Fabrication of green organic light-emitting diode (single host)

[0428] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing 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 and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum depositor. Using this prepared ITO transparent electrode as the anode, compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited onto the ITO substrate to form... A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form A thick hole transport layer. Compound B is deposited on the hole transport layer to form... A thick hole transport assist layer. Compound A-10 was used as the host material and doped with 7 wt% PhGD as a dopant on the hole transport assist layer, formed by vacuum deposition. A thick luminescent layer. Subsequently, compound C is deposited on the luminescent layer to form... A thick electron transport auxiliary layer was formed, and compounds D and LiQ were simultaneously vacuum-deposited at a 1:1 weight ratio to form... A thick electron transport layer. The electron transport layer is then deposited sequentially via vacuum deposition. LiQ and Al is used to form the cathode, thereby manufacturing an organic light-emitting diode.

[0429] The manufactured organic light-emitting diode has the following structure: ITO / compound A (3% NDP-9 doped). Compound A / Compound B / EML[Body (Compound A-10): PhGD = 93wt% : 7wt%] / Compound C / Compound D:LiQ / LiQ / Al

[0430] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0431] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluorene-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0432] 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

[0433] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluorene-4-yl)-6-phenyl-1,3,5-triazine

[0434] [PhGD]

[0435]

[0436] Examples 2 to 3 and Comparative Examples 1 to 3

[0437] Each organic light-emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed as described in Table 1.

[0438] Example 4: Fabrication of green organic light-emitting diode (mixed host)

[0439] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing 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 and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum deposition unit. Using this prepared ITO transparent electrode as the anode, compound E doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited onto the ITO substrate to form... A thick hole injection layer, and compound E is deposited on the hole injection layer to... The thickness is increased to form a hole transport layer. Compound F is deposited on the hole transport layer to... The thickness was adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compounds A-10 and C-4 in a 4:6 weight ratio were used simultaneously as the host and doped with 10 wt% PhGD as a dopant, to form the layer by vacuum deposition. A thick luminescent layer. Subsequently, compound G is deposited on the luminescent layer until... The thickness is such that an electron transport auxiliary layer is formed, and compounds H and LiQ are simultaneously vacuum-deposited at a weight ratio of 1:1 to form... A thick electron transport layer. This is achieved by sequential vacuum deposition on the electron transport layer. LiQ and Al is used to form the cathode, thereby manufacturing an organic light-emitting diode.

[0440] The manufactured organic light-emitting diode has the following structure: ITO / compound E (3% NDP-9 doped). ) / Compound E / compound F / EML[body(compound A-10:compound C-4 = 4: 6wt% / wt%):PhGD = 90wt%:10wt%] / Compound G / Compound H:LiQ / LiQ / Al

[0441] Compound E: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0442] Compound F: 9,9-Dimethyl-N-[3-(9-phenyl-9H-fluorene-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluorene-2-amine

[0443] Compound G: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0444] Compound H: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthyl-2-yl}-4,6-diphenyl-1,3,5-triazine)

[0445] Examples 5 to 6 and Comparative Examples 4 to 6

[0446] Each organic light-emitting diode was manufactured in the same manner as in Example 4, except that the composition was changed to those shown in Table 2.

[0447] Evaluation

[0448] The driving voltage, luminous efficiency, and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 6 and Comparative Examples 1 to 6 were evaluated.

[0449] The specific measurement methods are shown below, and the results are presented in Table 2.

[0450] (1) Measure the change in current density based on voltage change.

[0451] While increasing the voltage from 0V to 10V, the current flowing through the unit device in the manufactured organic light-emitting diode is measured using a current-voltmeter (Keithley 2400), and the measured current value is divided by the area to provide the result.

[0452] (2) Measure the brightness change based on voltage changes

[0453] The brightness was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0V to 10V.

[0454] (3) Measure luminous efficiency

[0455] Using the brightness and current density from (1) and (2) above, the same current density (10 mA / cm²) was calculated. 2 Luminous efficiency (cd / A) at )

[0456] The luminous efficiency values ​​of Examples 1 to 3 and Comparative Examples 1 to 3 were calculated based on the relative values ​​of Comparative Example 1 and are shown in Table 1.

[0457] The luminous efficiency values ​​of Examples 4 to 6 and Comparative Examples 4 to 6 were calculated based on the relative values ​​of Comparative Example 4 and are shown in Table 2.

[0458] (4) Measuring lifespan

[0459] 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.

[0460] 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.

[0461] 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.

[0462] (Table 1)

[0463] No. Host Luminous efficiency (%) Lifetime (%) Example 1 A-10 102 125 Example 2 A-13 102 118 Example 3 A-16 103 132 Comparative Example 1 R-1 100 100 Comparative Example 2 R-2 99 94 Comparative Example 3 R-3 100 103

[0464] (Table 2)

[0465] No. Host Luminous efficiency (%) Lifetime (%) Example 4 A-10 / C-4 105 151 Example 5 A-13 / C-4 104 134 Example 6 A-16 / C-4 107 162 Comparative Example 4 R-1 / C-4 100 100 Comparative Example 5 R-2 / C-4 99 95 Comparative Example 6 R-3 / C-4 100 108

[0466] Referring to Tables 1 and 2, compared with the organic light-emitting diodes according to Comparative Examples 1 to 6, the organic light-emitting diodes according to Examples 1 to 6 have significantly improved luminous efficiency and lifetime characteristics.

[0467] Although the invention has been described in conjunction with exemplary embodiments now considered practical, it should be understood that the invention is not limited to the disclosed embodiments. Rather, it 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: In chemical formula 1, R 1 To R 4 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C18 aryl. 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. m1, m3, and m4 are each an independent integer from 1 to 4. m2 is one of the integers from 1 to 3, and When m1 to m4 are 2 or greater, R 1 To R 4 They are the same as or different from each other.

2. The compound for organic optoelectronic devices according to claim 1, wherein, Chemical formula 1 can be represented by any one of chemical formulas 1A to 1C: In chemical formulas 1A to 1C R 1 To R 4 Ar 1 Ar 2 m1 to m4 as defined in claim 1.

3. The compound for organic optoelectronic devices according to claim 1, wherein, Chemical formula 1 can be represented by any one of chemical formulas 1A-1 to 1A-3, 1B-1 to 1B-3, and 1C-1 to 1C-3: In chemical formulas 1A-1 to 1A-3, 1B-1 to 1B-3, and 1C-1 to 1C-3 R 1 To R 4 Ar 1 Ar 2 m1 to m4 as defined in claim 1.

4. The compound for organic optoelectronic devices according to claim 3, wherein, Chemical formula 1A-1 can be represented by any one of chemical formulas 1A-1-I to 1A-1-IV: In chemical formulas 1A-1-I to 1A-1-IV R 1 To R 4 Ar 1 Ar 2 m1 to m4 as defined in claim 1.

5. The compound for organic optoelectronic devices according to claim 1, wherein, Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

6. The compound for organic optoelectronic devices according to claim 1, wherein, R 1 To R 4 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl or substituted or unsubstituted C6 to C12 aryl.

7. The compound for organic optoelectronic devices according to claim 1, wherein, The compounds are selected from those listed in Group 1: [Group 1] 8. 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 2, a combination of chemical formulas 3 and 4, or chemical formula 5: In chemical formula 2, R 5 To R 9 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 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene group. m5, m8, and m9 are each an independent integer from 1 to 4. m6 and m7 are each an independent integer from 1 to 3. When m5 to m9 are 2 or greater, R 5 To R 9 Each is the same as or different from the others, and n is one of the integers from 0 to 2; In chemical formulas 3 and 4, In chemical formula 3, a1* to a4*, each of the two adjacent ones is a linking carbon (C) connected to * in chemical formula 4. Of a1* to a4* in chemical formula 3, the other two not connected to chemical formula 4 are CL. a -R a , L a L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene group. R a R 10 and R 11 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 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m10 and m11 are each an independent integer from 1 to 4, and When m10 and m11 are 2 or greater, R 10 and R 11 Each is the same as or different from the other; In chemical formula 5, L 5 It is a single bond or a substituted or unsubstituted C6 to C20 arylene. R 12 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 7 It is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. m12, m14, and m15 are each an independent integer from 1 to 4. m13 is one of the integers from 1 to 3, and When m12 to m15 are 2 or greater, R 12 To R 15 They are the same as or different from each other.

9. The composition for an organic optoelectronic device according to claim 8, wherein, Chemical formula 2 is represented by chemical formula 2-8: In chemical formula 2-8, R 5 To R 8 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. m5 and m8 are each an independent integer from 1 to 4. m6 and m7 are each an independent integer from 1 to 3, and L 1 -Ar 3 and L 2 -Ar 4 Each substituent is independently selected from those listed in Group I. [Group I] In group I, R 19 To R 23 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m19 is one of the integers from 1 to 5. m20 is one of the integers from 1 to 4. m21 is one of the integers from 1 to 3. m22 is an integer of 1 or 2. m23 is one of the integers from 1 to 7, and * indicates a connection point.

10. The composition for an organic optoelectronic device according to claim 8, wherein, The combination of chemical formulas 3 and 4 is represented by chemical formula 3C: In the chemical formula 3C, L a3 and L a4 It's a single key. R 10 R 11 R a3 and R a4 Each is independently hydrogen, deuterium, or C6 to C12 aryl, m10 and m11 are each independently an integer from 1 to 4, and L 3 -Ar 5 and L 4 -Ar 6 Each substituent is independently selected from those listed in Group I. [Group I] In group I, R 19 To R 23 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m19 is one of the integers from 1 to 5. m20 is one of the integers from 1 to 4. m21 is one of the integers from 1 to 3. m22 is an integer of 1 or 2. m23 is one of the integers from 1 to 7, and * indicates a connection point.

11. An organic optoelectronic device, comprising: The anode and cathode facing each other, and At least one organic layer between the anode and the cathode, The organic layer comprises: The compound for an organic optoelectronic device according to any one of claims 1 to 7; or The composition for an organic optoelectronic device according to any one of claims 8 to 10.

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

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

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