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

Abstract

The present invention relates to: a compound for organic optoelectronic diodes, represented by chemical formula 1; and a composition for organic optoelectronic diodes, an organic optoelectronic diode, and a display device, comprising the compound. The details of chemical formula 1 is as defined in the specification.

Description

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

[0001] This relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.

[0002] An organic optoelectronic diode is a device capable of converting electrical energy and light energy.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One is a photovoltaic device that generates electrical energy as excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0004] Examples of organic optoelectronic devices include organic photovoltaic devices, organic light-emitting diodes, organic solar cells, and organic photoconductor drums.

[0005] Among these, organic light-emitting diodes (OLEDs) have recently been receiving significant attention due to the increasing demand for flat panel display devices. As an organic light-emitting diode is a device that converts electrical energy into light, its performance is greatly influenced by the organic material located between the electrodes.

[0006] One embodiment provides a compound for organic optoelectronic devices that can lower the driving voltage and realize high-efficiency and long-life organic optoelectronic devices.

[0007] Another embodiment provides a composition for an organic optoelectronic device comprising the above-mentioned compound for the organic optoelectronic device.

[0008] Another embodiment provides an organic optoelectronic device comprising the above-mentioned compound for the organic optoelectronic device or composition for the organic optoelectronic device.

[0009] Another embodiment provides a display device including the above-mentioned organic optoelectronic element.

[0010] According to one embodiment, a compound for an organic optoelectronic device represented by the following chemical formula 1 is provided.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] R 1 to R 4 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and

[0015] Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, and

[0016] A1 and A2 are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuran or substituted or unsubstituted dibenzothiophene, and

[0017] m1 to m4 are each independently one of integers 1 to 4, and

[0018] When m1 to m4 is 2 or more, each R 1 to R 4 They are identical or different from each other.

[0019] According to another embodiment, a composition for an organic optoelectronic device comprising a first compound and a second compound is provided.

[0020] The first compound above is a compound for an organic optoelectronic device as described above, and the second compound can be represented by the following chemical formula 2; a combination of the following chemical formulas 3 and 4; or the following chemical formula 5.

[0021] [Chemical Formula 2]

[0022]

[0023] In the above chemical formula 2,

[0024] R 13 to R 17 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0025] Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0026] L 1 and L 2 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0027] m13, m16, and m17 are each independently one of integers 1 to 4, and

[0028] m14 and m15 are each independently one of integers 1 to 3, and

[0029] If m13 to m17 are 2 or more, each R 13 to R 17 are identical or different from each other,

[0030] n is one of integers from 0 to 2;

[0031] [Chemical Formula 3] [Chemical Formula 4]

[0032]

[0033] In the above chemical formulas 3 and 4,

[0034] Among a1* to a4* of Chemical Formula 3, two adjacent ones are each a connecting carbon (C) connected to * of Chemical Formula 4, and

[0035] The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to Chemical Formula 4 are CL a -R a And,

[0036] L a , L 3 and L 4 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0037] R a , R 18 and R 19 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0038] 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, and

[0039] m18 and m19 are each independently one of integers 1 to 4, and

[0040] If m18 and m19 are 2 or more, respectively R 18 and R 19 are identical or different from each other;

[0041] [Chemical Formula 5]

[0042]

[0043] In the above chemical formula 5,

[0044] L 5Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0045] R 20 to R 23 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0046] Ar 6 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0047] m20, m22, and m23 are each independently one of integers 1 to 4, and

[0048] m21 is one of integers from 1 to 3, and

[0049] If m20 to m23 are 2 or more, each R 20 to R 23 They are identical or different from each other.

[0050] According to another embodiment, an organic optoelectronic device is provided comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises a compound for the organic optoelectronic device.

[0051] According to another embodiment, a display device comprising the organic optoelectronic element is provided.

[0052] It is possible to realize high-efficiency, long-life organic optoelectronic devices while lowering the driving voltage.

[0053]

[0054] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0055] <Explanation of Symbols>

[0056] 100: Organic light-emitting diode

[0057] 105: Organic layer

[0058] 110: Cathode

[0059] 120: Anode

[0060] 130: Emissive layer

[0061] 140: Precision Transport Area

[0062] 150: Electronic transport area

[0063]

[0064] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention, and the present invention is defined only by the scope of the claims set forth below.

[0065] In this specification, "substitution" means that, unless otherwise defined, at least one hydrogen of a substituent or compound is substituted with a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0066] In one example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C20 aryl group, a C2 to C20 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C18 aryl group, a C2 to C18 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a trimethylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0067] In this specification, “non-substituted” means that a hydrogen atom remains a hydrogen atom without being substituted by another substituent.

[0068] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0069] In this specification, "hetero" means, unless otherwise defined, that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon.

[0070] In this specification, "aryl group" is a collective concept for a group having one or more hydrocarbon aromatic moietys, including a form in which all elements of the hydrocarbon aromatic moiety have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group, a naphthyl group, etc., and a form in which two or more hydrocarbon aromatic moietys are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moietys are directly or indirectly fused, such as a fluorenyl group, etc.

[0071] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0072] In this specification, "heterocyclic group" is a superordinate concept including heteroaryl groups, meaning that a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C). If the heterocyclic group is a fused ring, it may contain one or more heteroatoms in the entire heterocyclic group or in each ring.

[0073] For example, a "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si within the aryl group. Two or more heteroaryl groups may be directly connected through sigma bonds, or if the heteroaryl group comprises two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain one to three heteroatoms.

[0074] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0075] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic groups are a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazoleyl group, a substituted or unsubstituted triazoleyl group, a substituted or unsubstituted oxazoleyl group, a substituted or unsubstituted thiazoleyl group, a substituted or unsubstituted oxadiazoleyl group, a substituted or unsubstituted thiadiazoleyl 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 benzothiophenyl group, a substituted or unsubstituted benzimidazoleyl group, a substituted or unsubstituted indoleyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthiridinyl group, a substituted or unsubstituted benzoxazine dil group, a substituted or unsubstituted benzthiazine dil group, a substituted or unsubstituted acrridinyl group, a substituted or unsubstituted phenazine dil group, a substituted or unsubstituted phenothiazine dil group, a substituted or unsubstituted phenoxazine dil group, a substituted or unsubstituted carbazole dil group, a substituted or unsubstituted dibenzofuran dil group, a substituted or unsubstituted dibenzothiophen dil group, a substituted or unsubstituted benzonaphtufuran dil group, a substituted or unsubstituted benzonaphthiophen dil group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0076] In this specification, the term "hole characteristic" refers to a characteristic that can form holes by donating electrons when an electric field is applied, and means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and movement within the light-emitting layer by having a conduction characteristic along the HOMO level.

[0077] In addition, electronic properties refer to the ability to receive electrons when an electric field is applied, and they refer to properties that facilitate the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed at the light-emitting layer to the cathode, and the movement of electrons within the light-emitting layer by having conduction properties along the LUMO level.

[0078] A compound for an organic optoelectronic device according to one embodiment is described below.

[0079] A compound for an organic optoelectronic device according to one embodiment is represented by the following chemical formula 1.

[0080] [Chemical Formula 1]

[0081]

[0082] In the above chemical formula 1,

[0083] R 1 to R 4 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and

[0084] Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, and

[0085] A1 and A2 are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuran or substituted or unsubstituted dibenzothiophene, and

[0086] m1 to m4 are each independently one of integers 1 to 4, and

[0087] When m1 to m4 is 2 or more, each R 1 to R 4 They are identical or different from each other.

[0088] The present invention has the following improvements compared to the aforementioned prior art patents.

[0089] 1. The present invention is characterized by being designed so that two Carbazoles are connected to ortho-phenylene and meta or para-phenylene centered on a triazine, thereby having mutually organic HOMO energy.

[0090] Unlike the existing development direction of bipolar hosts with n-type characteristics, a bipolar host with strong p-type characteristics can be designed by introducing two carbazoles, connecting one via an ortho-phenylene linker to form a material with an overall shallow HOMO value, and connecting the other via a meta or para-phenylene linker to control the HOMO value so that it can be effectively transferred to the dopant. In other words, the first feature is the appropriate use of phenyl linkers to distribute energy between the two carbazoles (refer to items 3 and 5), and the second feature is the design to allow LUMO electron clouds to be delocalized at the three substituent sites connected to the triazine to compensate for the n-type characteristics that may be weakened by the inclusion of two carbazoles (refer to item 6).

[0091] In particular, the ortho-phenylene linker of the present invention greatly aids in the formation of exciplexes and can significantly lower the deposition temperature compared to other linkers, thereby greatly increasing thermal stability. In addition, by ensuring sufficient intermolecular distance, triplet-triplet annihilation (TTA) can be significantly weakened, allowing for high efficiency characteristics.

[0092] 2. As the T1 energy increases due to the effect of step 1, a low ΔEST is obtained, and a low ΔEST enables the realization of a high-efficiency device.

[0093] 3. In the present invention, two carbazole groups capable of significantly increasing molecular stability were used. Carbazole is a unit with strong cation durability and is a substituent having hole characteristics capable of transferring cation to other molecules. By including two carbazoles, the cation stability of triazine was increased, significantly improving the degradation problem and enhancing long-life characteristics.

[0094] 4. In addition, as the number of Carbazole groups increases to two, there are more deuterium substitution sites, and a long-life device can be realized by compensating for weak CN bonding with deuterium substitution.

[0095] 5. A phenyl linker has been introduced between Triazine and Carbazole, offering significant advantages compared to a structure directly connected without a linker. Specifically, when using a bipolar host composed of Carbazole as the electronic host, if Carbazole is directly connected to Triazine, the CN bonding characteristics can cancel out the π-π bond, potentially causing the HOMO / LUMO electron clouds to become compartmentalized. Conversely, since the n-type triazine is positioned at the 9-direction where the Carbazole electron cloud can expand, there is a disadvantage in that the HOMO energy becomes deep and the driving voltage increases significantly. This invention is designed to maintain long lifespan characteristics and achieve low driving / high efficiency by appropriately introducing phenyl linkers on both sides where Carbazole is connected to enhance driving characteristics.

[0096] 6. Recently mass-produced triazine derivative materials are designed with structures that either directly substitute Carbazole without a linker or include an ortho linker to increase the cation stability of triazine. However, such designs can weaken n-type characteristics by blocking the expansion of the ET electron cloud of triazine. To address this drawback, dibenzofuran (DBF), which possesses strong n-type characteristics, is sometimes used; however, DBF has lower stability than phenyl groups due to its molecular structure. To solve this problem, the present invention substitutes all three substituents connected to triazine with only aryl groups, such as phenyl groups, and additionally substitutes Carbazole to ensure the LUMO electron cloud expands well, thereby compensating for the potentially insufficient n-type characteristics. With this design, it has become possible to realize low-drive / high-efficiency devices.

[0097] For example, the above chemical formula 1 can be represented by the following chemical formula 1A or chemical formula 1B.

[0098] [Chemical Formula 1A]

[0099]

[0100] [Chemical Formula 1B]

[0101]

[0102] In the above chemical formulas 1A and 1B,

[0103] R 1 to R 4 , Ar 1 , A1, A2, and m1 to m4 are as described above.

[0104] As a specific example, the above chemical formula 1 can be expressed as any one of the following chemical formulas 1-1 to 1-19.

[0105] [Chemical Formula 1-1]

[0106]

[0107] [Chemical Formula 1-2]

[0108]

[0109] [Chemical Formula 1-3]

[0110]

[0111] [Chemical Formula 1-4]

[0112]

[0113] [Chemical Formula 1-5]

[0114]

[0115] [Chemical Formula 1-6]

[0116]

[0117] [Chemical Formula 1-7]

[0118]

[0119] [Chemical Formula 1-8]

[0120]

[0121] [Chemical Formula 1-9]

[0122]

[0123] [Chemical Formula 1-10]

[0124]

[0125] [Chemical Formula 1-11]

[0126]

[0127] [Chemical Formula 1-12]

[0128]

[0129] [Chemical Formula 1-13]

[0130]

[0131] [Chemical Formula 1-14]

[0132]

[0133] [Chemical Formula 1-15]

[0134]

[0135] [Chemical Formula 1-16]

[0136]

[0137] [Chemical Formula 1-17]

[0138]

[0139] [Chemical Formula 1-18]

[0140]

[0141] [Chemical Formula 1-19]

[0142]

[0143] In the above chemical formulas 1-1 to 1-19,

[0144] R 1 to R 4 , Ar 1 , m1 to m4 are as described above, and

[0145] X 1 and X 2 is independently O, S, or CR a R b And,

[0146] R a and R b Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and

[0147] R 5 to R 12 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and

[0148] m5, m6, m8, m9, and m12 are each independently one of integers 1 to 4, and

[0149] m7, m10, and m11 are each independently integers of 1 or 2.

[0150] In one embodiment, the compound for the organic optoelectronic device can be represented by the chemical formula 1-1.

[0151] For example, the above Ar 1 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group or a substituted or unsubstituted triphenylene group.

[0152] For example, the above R 1 to R 12 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted trimethylsilyl group or substituted or unsubstituted phenyl group.

[0153] In the most specific embodiment, the compound represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0154] [Group 1]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209] Dn represents the number of deuterium substitutions, and n is one of the integers from 1 to the maximum number of substitutions possible.

[0210] A composition for an organic optoelectronic device according to another embodiment comprises a first compound and a second compound, wherein the first compound is the aforementioned compound for an organic optoelectronic device, and the second compound may be represented by the following chemical formula 2; a combination of the following chemical formulas 3 and 4; or the following chemical formula 5.

[0211] [Chemical Formula 2]

[0212]

[0213] In the above chemical formula 2,

[0214] R 13 to R 17 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0215] Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0216] L 1 and L 2 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0217] m13, m16, and m17 are each independently one of integers 1 to 4, and

[0218] m14 and m15 are each independently one of integers 1 to 3, and

[0219] If m13 to m17 are 2 or more, each R 13 to R 17 are identical or different from each other,

[0220] n is one of integers from 0 to 2;

[0221] [Chemical Formula 3] [Chemical Formula 4]

[0222]

[0223] In the above chemical formulas 3 and 4,

[0224] Among a1* to a4* of Chemical Formula 3, two adjacent ones are each a connecting carbon (C) connected to * of Chemical Formula 4, and

[0225] The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to Chemical Formula 4 are CL a -R a And,

[0226] L a , L 3 and L 4 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0227] R a , R 18 and R 19 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0228] 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, and

[0229] m18 and m19 are each independently one of integers 1 to 4, and

[0230] If m18 and m19 are 2 or more, respectively R 18 and R 19 are identical or different from each other;

[0231] [Chemical Formula 5]

[0232]

[0233] In the above chemical formula 5,

[0234] L 5 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0235] R 20 to R 23 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0236] Ar 6 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0237] m20, m22, and m23 are each independently one of integers 1 to 4, and

[0238] m21 is one of integers from 1 to 3, and

[0239] If m20 to m23 are 2 or more, each R 20 to R 23 They are identical or different from each other.

[0240] The second compound mentioned above can be used in the light-emitting layer together with the first compound to increase charge mobility and stability, thereby improving luminous efficiency and lifespan characteristics.

[0241] In the above Chemical Formula 2, when m13 is 2 or more, each R 13 They may be identical or different from each other,

[0242] In the above Chemical Formula 2, when m14 is 2 or more, each R 14 They may be identical or different from each other,

[0243] In the above Chemical Formula 2, when m15 is 2 or more, each R 15 They may be identical or different from each other,

[0244] In the above Chemical Formula 2, when m16 is 2 or more, each R 16 They may be identical or different from each other,

[0245] In the above Chemical Formula 2, when m17 is 2 or more, each R 17 They may be identical or different from each other,

[0246] In the above Chemical Formulas 3 and 4, when m18 is 2 or more, each R 18 are identical or different from each other,

[0247] In the above Chemical Formulas 3 and 4, when m19 is 2 or more, each R 19 They are identical or different from each other,

[0248] In the above Chemical Formula 5, when m20 is 2 or more, each R 20 are identical or different from each other,

[0249] In the above Chemical Formula 5, when m21 is 2 or more, each R 21 are identical or different from each other,

[0250] In the above Chemical Formula 5, when m22 is 2 or more, each R 22 They are identical or different from each other,

[0251] In the above Chemical Formula 5, when m23 is 2 or more, each R 23 They are identical or different from each other.

[0252] As an example, Ar of the above chemical formula 2 2 and Ar 3 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0253] L of the above chemical formula 21 and L 2 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and

[0254] R of the above chemical formula 2 13 to R 17 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0255] n can be 0 or 1.

[0256] For example, the term "substitution" in the above chemical formula 2 means that at least one hydrogen is substituted with a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0257] For example, Ar of the above chemical formula 2 2 and Ar 3 Each may independently be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0258] In a specific embodiment of the present invention, the formula 2 may be represented by one of the following formulas 2-1 to 2-15.

[0259] [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3]

[0260]

[0261] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6]

[0262]

[0263] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9]

[0264]

[0265] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12]

[0266]

[0267] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15]

[0268]

[0269] In the above chemical formulas 2-1 to 2-15, R 13 to R 17 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 1 -Ar 2 and L 2 -Ar 3 Each can be independently one of the substituents listed in Group I below.

[0270] [Group I]

[0271]

[0272] In the above Group I,

[0273] R 24 to R 30 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[0274] m24 is one of integers from 1 to 5, and

[0275] m25 is one of integers from 1 to 4, and

[0276] m26 is one of integers from 1 to 3, and

[0277] m27 is an integer of 1 or 2, and

[0278] m28 is one of integers from 1 to 7, and

[0279] * is a connection point.

[0280] In the above Group I, if m24 is 2 or more, each R 24 They may be the same or different from each other.

[0281] In the above Group I, when m25 is 2 or greater, each R 25 They may be the same or different from each other.

[0282] In the above Group I, when m26 is 2 or greater, each R 26 It may be the same or different.

[0283] In the above Group I, when m27 is 2, each R 27 It may be the same or different.

[0284] In the above Group I, when m28 is 2 or more, each R 28 It may be the same or different.

[0285] The combination of the above chemical formulas 3 and 4 can be expressed, for example, as any one of the following chemical formulas 3A, 3B, 3C, 3D, and 3E.

[0286] [Chemical Formula 3A] [Chemical Formula 3B] [Chemical Formula 3C]

[0287]

[0288] [Chemical Formula 3D] [Chemical Formula 3E]

[0289]

[0290] In the above chemical formulas 3A to 3E, L 3 , L 4 , Ar 4 , Ar 5 , R 18 , R 19 , m18 and m19 are as previously stated, and

[0291] L a1 to L a4 is the aforementioned L 3 and L 4 It is the same as the definition of,

[0292] R a1 to R a4 is the aforementioned R 18 and R 19 It is the same as the definition of.

[0293] For example, Ar of the above Chemical Formulas 3 and 4 4 and Ar 5 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0294] R a1 to R a4 , R 18 and R 19 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0295] In a specific embodiment of the present invention, L of Formulas 3 and 4 3 -Ar 4 and L 4 -Ar 5 Each can be independently selected from the substituents listed in Group I above.

[0296] In one embodiment, the R a1 to R a4 , R 18 and R 19 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0297] For example, the above R a1 to R a4 , R 18 and R19 Each can independently be a hydrogen, deuterium, cyano group, or a substituted or unsubstituted phenyl group, and

[0298] In a specific embodiment, the R a1 to R a4 , R 18 and R 19 Each can independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0299] The above chemical formula 5 can be expressed, for example, by any one of the following chemical formulas 5-1 to 5-4.

[0300] [Chemical Formula 5-1] [Chemical Formula 5-2]

[0301]

[0302] [Chemical Formula 5-3] [Chemical Formula 5-4]

[0303]

[0304] In the above chemical formulas 5-1 to 5-4, L 5 , Ar 6 , R 20 to R 23 and m20 to m23 are as described above.

[0305] For example, Ar of the above chemical formula 5 6 ... is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0306] R 20 to R 23Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0307] In a specific embodiment of the present invention, L of Formula 5 5 -Ar 6 It can be selected from the substituents listed in Group I above.

[0308] For example, the above R 20 to R 23 Each can independently be a hydrogen, deuterium, cyano group, or a substituted or unsubstituted phenyl group.

[0309] It can be expressed by the above chemical formula 2-8, and the Ar of the above chemical formula 2-8 2 and Ar 3 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and L 1 and L 2 Each is independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and R 13 to R 16 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0310] For example, R of the above chemical formula 2-8 13 to R 16 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 1 -Ar 2and L 2 -Ar 3 Each may independently be one of the substituents listed in Group I above.

[0311] In another specific embodiment of the present invention, the second compound may be represented by the formula 4C, and L of the formula 3C a3 and L a4 is a single bond, and L 3 and L 4 Each is independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 18 , R 19 , R a3 and R a4 are hydrogen, deuterium, or a phenyl group, respectively, and Ar 4 and Ar 5 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0312] For example, L of the above chemical formula 3C a3 and L a4 is a single bond, and R 18 , R 19 , R a3 and R a4 Each is independently hydrogen, deuterium, or a C6 to C12 aryl group, and L 3 -Ar 4 and L 4 -Ar 5 Each may independently be one of the substituents listed in Group I above.

[0313] For example, the compound for the second organic optoelectronic device may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0314] [Group 2]

[0315] [B-1] [B-2] [B-3] [B-4] [B-5]

[0316]

[0317] [B-6] [B-7] [B-8] [B-9] [B-10]

[0318]

[0319] [B-11] [B-12] [B-13] [B-14] [B-15]

[0320]

[0321] [B-16] [B-17] [B-18] [B-19] [B-20]

[0322]

[0323] [B-21] [B-22] [B-23] [B-24] [B-25]

[0324]

[0325] [B-26] [B-27] [B-28] [B-29] [B-30]

[0326]

[0327] [B-31] [B-32] [B-33] [B-34] [B-35]

[0328]

[0329] [B-36] [B-37] [B-38] [B-39] [B-40]

[0330]

[0331] [B-41] [B-42] [B-43] [B-44] [B-45]

[0332]

[0333] [B-46] [B-47] [B-48] [B-49] [B-50]

[0334]

[0335] [B-51] [B-52] [B-53] [B-54] [B-55]

[0336]

[0337] [B-56] [B-57] [B-58] [B-59] [B-60]

[0338]

[0339] [B-61] [B-62] [B-63] [B-64] [B-65]

[0340]

[0341] [B-66] [B-67] [B-68] [B-69] [B-70]

[0342]

[0343] [B-71] [B-72] [B-73] [B-74] [B-75]

[0344]

[0345] [B-76] [B-77] [B-78] [B-79] [B-80]

[0346]

[0347] [B-81] [B-82] [B-83] [B-84] [B-85]

[0348]

[0349] [B-86] [B-87] [B-88] [B-89] [B-90]

[0350]

[0351] [B-91] [B-92] [B-93] [B-94] [B-95]

[0352]

[0353] [B-96] [B-97] [B-98] [B-99] [B-100]

[0354]

[0355] [B-101] [B-102] [B-103] [B-104] [B-105]

[0356]

[0357] [B-106] [B-107] [B-108] [B-109] [B-110]

[0358]

[0359] [B-111] [B-112] [B-113] [B-114] [B-115]

[0360]

[0361] [B-116] [B-117] [B-118] [B-119] [B-120]

[0362]

[0363] [B-121] [B-122] [B-123] [B-124] [B-125]

[0364]

[0365] [B-126] [B-127] [B-128] [B-129] [B-130]

[0366]

[0367] [B-131] [B-132] [B-133] [B-134] [B-135]

[0368]

[0369] [B-136] [B-137] [B-138]

[0370]

[0371] [B-139] [B-140] [B-141] [B-142]

[0372]

[0373] [B-143] [B-144] [B-145]

[0374]

[0375] [B-146] [B-147] [B-148] [B-149]

[0376]

[0377] [B-150]

[0378]

[0379] Additionally, an example of a form in which at least one hydrogen in compounds B-1 to B-150 listed in Group 2 above is substituted with deuterium is presented below, but is not limited thereto.

[0380] [B-151] [B-152] [B-153] [B-154] [B-155]

[0381]

[0382] [B-156] [B-157] [B-158] [B-159] [B-160]

[0383]

[0384] [B-161] [B-162] [B-163] [B-164] [B-165]

[0385]

[0386] [B-166] [B-167] [B-168] [B-169] [B-170]

[0387]

[0388] [B-171] [B-172] [B-173] [B-174] [B-175]

[0389]

[0390] [B-176] [B-177] [B-178] [B-179] [B-180]

[0391]

[0392] [B-181] [B-182] [B-183] [B-184] [B-185]

[0393]

[0394] [B-186] [B-187] [B-188] [B-189] [B-190]

[0395]

[0396] [B-191] [B-192] [B-193] [B-194] [B-195]

[0397]

[0398] (Dn represents the number of deuterium substitutions, where n is an integer between 1 and the maximum possible number of substitutions.)

[0399] The most specific structures of compounds B-151 to B-195 of Group 2 above are presented below as examples based on the deuterium substitution positions and substitution rates, and there is no intention to limit the scope of rights for compounds not presented below.

[0400] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the deuterium substitution position and deuterium substitution rate, etc., may include all ranges that can be changed within the range of compounds B-1 to B-195.

[0401] [B-196] [B-197] [B-198]

[0402]

[0403] [B-199] [B-200] [B-201] [B-202]

[0404]

[0405] [B-203] [B-204] [B-205] [B-206]

[0406]

[0407] [B-207] [B-208] [B-209] [B-210]

[0408]

[0409] [B-211] [B-212] [B-213] [B-214]

[0410]

[0411] [B-215] [B-216] [B-217]

[0412]

[0413] [B-218] [B-219] [B-220] [B-221]

[0414]

[0415] [B-222] [B-223] [B-224] [B-225]

[0416]

[0417] [B-226] [B-227] [B-228] [B-229]

[0418]

[0419] [B-230] [B-231] [B-232] [B-233]

[0420]

[0421] [B-234]

[0422]

[0423] [C-1] [C-2] [C-3] [C-4]

[0424]

[0425] [C-5] [C-6] [C-7] [C-8]

[0426]

[0427] [C-9] [C-10] [C-11] [C-12]

[0428]

[0429] [C-13] [C-14] [C-15] [C-16]

[0430]

[0431] [C-17] [C-18] [C-19] [C-20]

[0432]

[0433] [C-21] [C-22] [C-23] [C-24]

[0434]

[0435] [C-25] [C-26] [C-27] [C-28]

[0436]

[0437] [C-29] [C-30] [C-31] [C-32]

[0438]

[0439] [C-33] [C-34] [C-35] [C-36]

[0440]

[0441] [C-37] [C-38] [C-39] [C-40]

[0442]

[0443] [C-41] [C-42] [C-43] [C-44]

[0444]

[0445] [C-45] [C-46] [C-47] [C-48]

[0446]

[0447] [C-49] [C-50] [C-51] [C-52]

[0448]

[0449] [C-53] [C-54] [C-55] [C-56]

[0450]

[0451] [C-57]

[0452]

[0453] Additionally, an example of a form in which at least one hydrogen in compounds C-1 to C-57 listed in Group 2 above is substituted with deuterium is presented below, but is not limited thereto.

[0454] [C-58] [C-59] [C-60] [C-61] [C-62]

[0455]

[0456] [C-63] [C-64] [C-65] [C-66] [C-67]

[0457]

[0458] [C-68] [C-69] [C-70] [C-71] [C-72]

[0459]

[0460] (Dn represents the number of deuterium substitutions, where n is an integer between 1 and the maximum possible number of substitutions.)

[0461] The most specific structures of compounds C-58 to C-72 of Group 2 above are presented below as examples according to the deuterium substitution positions and substitution rates, and there is no intention to limit the scope of rights for compounds not presented below.

[0462] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the deuterium substitution position and deuterium substitution rate, etc., may include all ranges that can be changed within the range of compounds C-1 to C-72.

[0463] [C-73] [C-74]

[0464]

[0465] [C-75] [C-76] [C-77] [C-78]

[0466]

[0467] [C-79] [C-80] [C-81] [C-82]

[0468]

[0469] [C-83] [C-84] [C-85] [C-86]

[0470]

[0471] [C-87] [C-88] [C-89] [C-90]

[0472]

[0473] [C-91] [C-92] [C-93] [C-94]

[0474]

[0475] [C-95] [C-96] [C-97] [C-98]

[0476]

[0477] [C-99] [C-100] [C-101] [C-102]

[0478]

[0479] [D-1] [D-2] [D-3] [D-4] [D-5]

[0480]

[0481] [D-6] [D-7] [D-8] [D-9] [D-10]

[0482]

[0483] [D-11] [D-12] [D-13] [D-14] [D-15]

[0484]

[0485] [D-16] [D-17] [D-18] [D-19] [D-20]

[0486]

[0487] [D-21] [D-22] [D-23] [D-24] [D-25]

[0488]

[0489] [D-26] [D-27] [D-28] [D-29] [D-30]

[0490]

[0491] [D-31] [D-32] [D-33] [D-34] [D-35]

[0492]

[0493] [D-36] [D-37] [D-38] [D-39] [D-40]

[0494]

[0495] [D-41] [D-24] [D-43] [D-44] [D-45]

[0496]

[0497] [D-46] [D-47] [D-48] [D-49] [D-50]

[0498]

[0499] [D-51] [D-52] [D-53] [D-54] [D-55]

[0500]

[0501] [D-56] [D-57] [D-58] [D-59] [D-60]

[0502]

[0503] Additionally, an example of a form in which at least one hydrogen in compounds D-1 to D-60 listed in Group 2 above is substituted with deuterium is presented below, but is not limited thereto.

[0504] [D-61] [D-62] [D-63] [D-64] [D-65]

[0505]

[0506] [D-66] [D-67] [D-68] [D-69] [D-70]

[0507]

[0508] [D-71] [D-72] [D-73] [D-74] [D-75]

[0509]

[0510] [D-76] [D-77] [D-78] [D-79] [D-80]

[0511]

[0512] [D-81] [D-82] [D-83] [D-84] [D-85]

[0513]

[0514] [D-86] [D-87] [D-88] [D-89] [D-90]

[0515]

[0516] [D-91] [D-92] [D-93] [D-94] [D-95]

[0517]

[0518] [D-96] [D-97] [D-98] [D-99] [D-100]

[0519]

[0520] [D-101] [D-102] [D-103] [D-104] [D-105]

[0521]

[0522] [D-106] [D-107] [D-108] [D-109] [D-110]

[0523]

[0524] [D-111] [D-112] [D-113] [D-114] [D-115]

[0525]

[0526] [D-116] [D-117] [D-118] [D-119] [D-120]

[0527]

[0528] (Dn represents the number of deuterium substitutions, where n is an integer between 1 and the maximum possible number of substitutions.)

[0529] In the most specific embodiment of the present invention, the first compound may be represented by the formula 1-1, and the second compound may be represented by the formula 3C.

[0530] In one embodiment, R of Formula 1-1 1 to R 6 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0531] Ar 1 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and

[0532] m1 to m6 can each independently be one of integers 1 to 4.

[0533] In addition, L of the above chemical formula 3C a3 and L a4 is a single bond, and

[0534] L 3 and L 4 Each is independently a single bond or a substituted or unsubstituted phenylene group, and

[0535] R 18 , R 19 , R a3 and R a4 Each is independently hydrogen, deuterium, or a C6 to C12 aryl group, and

[0536] Ar 4 and Ar 5 Each is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and

[0537] m18 and m19 can each independently be one of integers from 1 to 4.

[0538] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By including them within the above range, bipolar characteristics can be realized by adjusting the weight ratio appropriately using the electron transport ability of the first compound and the hole transport ability of the second compound, thereby improving efficiency and lifespan. Within the above range, they may be included in a weight ratio of, for example, about 10:90 to 90:10 or about 20:80 to 80:20, and 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 a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0539] An organic optoelectronic device to which the compound for organic optoelectronic devices or the composition for organic optoelectronic devices described above is applied is described below.

[0540] Organic optoelectronic devices are not particularly limited as long as they are devices capable of mutually converting electrical energy and light energy, and examples include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0541] Here, an organic light-emitting diode, which is an example of an organic optoelectronic device, is described with reference to the drawing.

[0542] FIG. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0543] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) located between the anode (120) and the cathode (110).

[0544] The anode (120) may be made of a conductor with a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The anode (120) may be a metal or an alloy thereof, such as nickel, platinum, vanadium, chromium, copper, zinc, gold; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide 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) (polyethylenedioxythiophene: PEDOT), polypyrrole and polyaniline, but is not limited thereto.

[0545] The cathode (110) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The cathode (110) may be a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; or a multilayer structure material such as LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca, but is not limited thereto.

[0546] The organic layer (105) may include the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices.

[0547] The above organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) includes a host and a dopant, the host may include the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices, and the dopant may be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0548] A dopant is a substance that is mixed in trace amounts into a compound or composition for an organic optoelectronic device to produce light emission, and generally, a substance such as a metal complex that emits light through multiple excitation, which excites it to a triplet state or higher, may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or more types.

[0549] Phosphorescent dopants are an example of a dopant, and examples of phosphorescent dopants include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may include, for example, compounds represented by the following chemical formula Z, but are not limited thereto.

[0550] [Chemical Formula Z]

[0551] L 6 MX 3

[0552] In the above chemical formula Z, M is a metal, and L 6 and X 3 is a ligand that is the same or different from each other and forms a complex with M.

[0553] The above M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and the above L 6 and X 3It can be, for example, a bitentate ligand.

[0554] L 6 and X 3 The ligand represented by may be one selected from the following chemical formulas Z-1 to Z-8.

[0555] [Z-1] [Z-2] [Z-3]

[0556]

[0557] [Z-4] [Z-5]

[0558]

[0559] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0560]

[0561] [Z-8]

[0562]

[0563] In the above chemical formulas Z-1 to Z-8,

[0564] X 14 is selected from the group consisting of carbon and nitrogen, and

[0565] Y 100 is O or S,

[0566] R 101 to R 122 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135Or; or may be connected to adjacent substituents to form a substituted or unsubstituted ring, for example, together with pyridine, may form a substituted or unsubstituted quinoline, substituted or unsubstituted benzopropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopropynoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenopyridine;

[0567] m18 is an integer from 1 to 4, and

[0568] m19 is an integer from 1 to 5.

[0569] L 6 and X 3 Examples of ligands represented by may be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0570] [Group A]

[0571]

[0572]

[0573] In the above group A,

[0574] 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.

[0575] R 303 to R 308Each is independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0576] m29 is one of integers from 1 to 5, and

[0577] m30 is one of integers from 1 to 4, and

[0578] m31 is one of integers from 1 to 3, and

[0579] m32 is an integer of 1 or 2, and

[0580] m33 is one of integers 1 to 6, and

[0581] If m29 to m33 are 2 or more, each R 303 to R 307 They are identical or different from each other.

[0582] The dopant according to one embodiment may be an iridium complex and may be represented, for example, by one of the following chemical formulas 7 to 9.

[0583] [Chemical Formula 7]

[0584]

[0585] In the above chemical formula 7,

[0586] Ring A is a monocyclic ring or a polycyclic fused ring, and

[0587] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0588] R 100 ...represents one to a maximum number of monovalent substituents,

[0589] R 100 If there are 2 or more of these, each R 100 They are identical or different from each other,

[0590] R 101 to R 104 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0591] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0592] X 10 and X 11 Each is independently selected from the group consisting of carbon and nitrogen, and

[0593] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0594] m21 is any one of integers from 0 to 3.

[0595] [Chemical Formula 8]

[0596]

[0597] In the above chemical formula 8,

[0598] Ring B is a monocyclic ring or a polycyclic fused ring, and

[0599] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0600] Y 100 is O or S,

[0601] R 201 ...represents one to a maximum number of monovalent substituents,

[0602] R 201 If there are 2 or more of these, each R 201 They are identical or different from each other,

[0603] R 206 to R 213 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0604] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0605] X 12 and X 13 Each is independently selected from the group consisting of carbon and nitrogen, and

[0606] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0607] m21 is any one of integers from 0 to 3.

[0608] [Chemical Formula 9]

[0609]

[0610] In the above chemical formula 9,

[0611] Y100 is O or S,

[0612] R 101 to R 111 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0613] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0614] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0615] m21 is any one of integers from 0 to 3.

[0616] As a more specific example, the above iridium complex can be represented by one of the following chemical formulas 7-1 to 7-6.

[0617] [Chemical Formula 7-1]

[0618]

[0619] In the above chemical formula 7-1,

[0620] R 101 to R 116 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 132 R 133 R 134 or -GeR 132 R 133 R 134 And,

[0621] The above R 132 to R134 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0622] R 101 to R 116 At least one of them is a functional group represented by the following chemical formula V-1, and

[0623] L 100 It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0624] m21 and m22 are independently any one of integers from 0 to 3, and m21 + m22 is any one of integers from 1 to 3, and

[0625] [Chemical Formula V-1]

[0626]

[0627] In the above chemical formula V-1,

[0628] R 135 to R 139 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0629] * represents the part connected to the carbon atom.

[0630] [Chemical Formula 7-2]

[0631]

[0632] [Chemical Formula 7-3]

[0633]

[0634] [Chemical Formula 7-4]

[0635]

[0636] [Chemical Formula 7-5]

[0637]

[0638] [Chemical Formula 7-6]

[0639]

[0640] In the above chemical formulas 7-2 to 7-6,

[0641] X 14 is selected from the group consisting of carbon and nitrogen, and

[0642] Y 100 is O or S,

[0643] R 101 to R 122 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 And,

[0644] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0645] L 100 It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0646] m111 is an integer from 1 to 2, and

[0647] n1 and n2 are independently any one of integers from 0 to 3, and n1 + n2 is any one of integers from 1 to 3.

[0648] A dopant according to another embodiment may be a platinum complex, for example, represented by the chemical formula Z-10.

[0649] [Chemical Formula Z-10]

[0650]

[0651] In the above chemical formula Z-10, rings A, B, C, and D each independently represent a pentagonal or hexagonal carbocyclic or heterocyclic ring;

[0652] R A , R B , R C , and R D Each independently represents a uniform, bisubstitution, trisubstitution, or quadruple substitution, or no substitution;

[0653] nA is an integer of 0 or 1;

[0654] L B , L C , and L D Each is independently selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0655] If nA is 1, L E is selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; and when nA is 0, L E is not present;

[0656] R A , R B , R C , R D , R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D, R, and R' are arbitrarily connected to form a ring; X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 Each represents oxygen or direct bonding.

[0657] The above platinum complex can be represented, for example, by the following chemical formula 8-1 or chemical formula 8-2.

[0658] [Chemical Formula 8-1]

[0659]

[0660] [Chemical Formula 8-2]

[0661]

[0662] In the above chemical formulas 8-1 and 8-2,

[0663] X 100 It contains O, S, and NR 132 Selected from among,

[0664] R 118 to R 132 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 133 R 134 R 135 And,

[0665] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0666] R 118 to R 132 At least one of them is -SiR 133 R 134 R 135 or is a tert-butyl group, and

[0667] The above R133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group.

[0668] The organic layer may include additional charge transport regions in addition to the light-emitting layer.

[0669] The above charge transport region may be, for example, a hole transport region (140).

[0670] 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.

[0671] 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 compounds listed in Group B below may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0672] [Group B]

[0673]

[0674]

[0675]

[0676]

[0677]

[0678]

[0679]

[0680]

[0681]

[0682]

[0683]

[0684]

[0685]

[0686]

[0687]

[0688]

[0689]

[0690]

[0691]

[0692]

[0693]

[0694]

[0695]

[0696]

[0697]

[0698]

[0699]

[0700]

[0701]

[0702]

[0703]

[0704]

[0705]

[0706] (Dn represents the number of deuterium substitutions, where n is an integer between 1 and the maximum possible number of substitutions.)

[0707] In addition to the aforementioned compound, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. may also be used in the hole transport region (140).

[0708] In addition, the charge transport region may be, for example, an electron transport region (150).

[0709] The above 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.

[0710] 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 compounds listed in Group C below may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0711] [Group C]

[0712]

[0713]

[0714]

[0715]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723]

[0724]

[0725]

[0726]

[0727]

[0728]

[0729] One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

[0730] Another embodiment may be an organic light-emitting device including a light-emitting layer and a hole transport region as the organic layer.

[0731] Another embodiment may be an organic light-emitting device including a light-emitting layer and an electron transport region as organic layers.

[0732] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to the light-emitting layer (130) as an organic layer (105) as shown in FIG. 1.

[0733] Meanwhile, the organic light-emitting device may additionally include an electron injection layer (not shown), a hole injection layer (not shown), etc., in addition to the light-emitting layer as the aforementioned organic layer.

[0734] An organic light-emitting device (100) can be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer using a dry film deposition method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and then forming a cathode or an anode thereon.

[0735] The above-described organic light-emitting element can be applied to an organic light-emitting display device.

[0736] The above-described embodiment will be explained in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the claims.

[0737] Unless otherwise noted, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized using known methods.

[0738]

[0739] (Synthesis of compounds for organic optoelectronic devices)

[0740] Synthesis Example 1: Synthesis of Intermediate I-1

[0741] [Reaction Equation 1]

[0742]

[0743] Carbazole (36.4g, 218.0mmol) purchased from Uksung Chemical (http: / www.ukseung.co.kr / ) was dissolved in 0.5L of dimethylforamide under a nitrogen environment. Subsequently, 1-chloro-3-fluorobenzene (23.7g, 181.5 mmol) and potassium tert-butoxide (24.4g, 218.0mmol) purchased from Sigma Aldrich (http: / www.sigmaaldrich.com / ) were added, and the mixture was heated at 180°C for 24 hours under reflux. After the reaction was complete, water was added to the reaction solution, and the mixture was filtered. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-1 (44.2g, 88%).

[0744] HRMS (70eV, EI+): m / z calcd for C18H12ClN: 277.0658, found: 277.

[0745] Elemental Analysis: C, 78%; H, 4%

[0746]

[0747] Synthesis Example 2: Synthesis of Intermediate I-2

[0748] [Reaction Equation 2]

[0749]

[0750] Intermediate I-1 (44.2 g, 159.2 mmol) was dissolved in 0.5 L of Xylene under a nitrogen environment, then bis(pinacolato)diboron (60.6 g, 238.6 mmol) purchased from P&H tech (http: / www.phtech.co.kr / ), Tris(dibenzylideneacetone)dipalladium (0) (4.4 g, 4.8 mmol), Tricyclohexylphosphine (10.7 g, 38.2 mmol), and potassium acetate (46.9 g, 477.5 mmol) were added, and the mixture was heated at 170°C for 24 hours and refluxed. After the reaction was complete, water was added to the reaction solution and extracted with dichloromethane (MC), then water was removed with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The residue obtained in this way was separated and purified by flash column chromatography to obtain intermediate I-2 (40.0g, 68%).

[0751] HRMS (70eV, EI+): m / z calcd for C24H24BNO2: 369.1900, found: 369.

[0752] Elemental Analysis: C, 78%; H, 7%

[0753]

[0754] Synthesis Example 3: Synthesis of Intermediate I-3

[0755] [Reaction Equation 3]

[0756]

[0757] Intermediate I-2 (40.0 g, 108.4 mmol) was dissolved in 0.15 L of xylene under a nitrogen environment, to which 2,4-dichloro-6-phenyl-1,3,5-triazine (37.0 g, 163 mmol) and tetrakis(triphenylphosphine)palladium (1.30 g, 1.08 mmol) were added and stirred. Then, 0.15 L of water-saturated potassium carbonate (37.4 g, 271 mmol) and tetrahydrofuran (THF) were added, and the mixture was heated at 80°C for 16 hours under reflux. After the reaction was complete, water was added to the reaction mixture and extracted with dichloromethane (DCM). Subsequently, water was removed using magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-3 (26.5 g, 56%).

[0758] HRMS (70eV, EI+): m / z calcd for C27H17ClN4: 432.1142, found: 432.

[0759] Elemental Analysis: C, 75%; H, 4%

[0760]

[0761] Synthesis Example 4: Synthesis of Compound 1

[0762] [Reaction Equation 4]

[0763]

[0764] Under a nitrogen environment, intermediate I-3 (27 g, 62.3 mmol) was dissolved in 0.4 L of tetrahydrofuran (THF). Then, 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (27.6 g, 74.8 mmol) and tetrakis(triphenylphosphine)palladium (1.44 g, 1.24 mmol), purchased from Mascot (Asia) Company Limited, were added and stirred. Subsequently, potassium carbonate (21.5 g, 155.9 mmol) saturated with water was added, and the mixture was heated at 80°C for 12 hours under reflux. After the reaction was complete, water was added to the reaction mixture and extracted with dichloromethane (DCM). After removing moisture with magnesium sulfate anhydrous, the mixture was filtered and concentrated under reduced pressure. The residue obtained in this way was separated and purified by flash column chromatography to obtain compound 1 (32.5g, 81%).

[0765]

[0766] HRMS (70eV, EI+): m / z calcd for C45H29N5: 639.2423, found: 639.

[0767] Elemental Analysis: C, 84%; H, 5%

[0768]

[0769] Synthesis Example 5: Synthesis of Intermediate I-4

[0770] [Reaction Equation 5]

[0771]

[0772] Intermediate I-4 (12.89 g, 78%) was obtained using intermediate I-3 (14.61 g, 33.7 mmol) and 2-fluorophenylboronic acid (5.7 g, 40.5 mmol) purchased from Tokyo Chemical Industry (http: / www.tcichemicals.com / ) in the same manner as in Synthesis Example 4.

[0773] HRMS (70eV, EI+): m / z calcd for C33H21FN4: 492.1750, found: 492.

[0774] Elemental Analysis: C, 80%; H, 4%

[0775]

[0776] Synthesis Example 6: Synthesis of Compound 8

[0777] [Reaction Equation 6]

[0778]

[0779] Compound 8 (16.0 g, 85%) was obtained using intermediate I-4 (12.89 g, 26.2 mmol) and 4-phenyl-9H-carbazole (10.0 g, 39.3 mmol) purchased from gemchem (http: / www.ytgemchem.com) in the same manner as in Synthesis Example 1.

[0780] HRMS (70eV, EI+): m / z calcd for C51H33N5: 715.2736, found: 715.

[0781] Elemental Analysis: C, 86%; H, 5%

[0782]

[0783] Synthesis Example 7: Synthesis of Intermediate I-5

[0784] [Reaction Equation 7]

[0785]

[0786] Intermediate I-5 (45.49 g, 88%) was obtained using carbazole-d8 (38.2 g, 218.0 mmol) and 1-chloro-3-fluorobenzene (23.7 g, 181.5 mmol) in the same manner as in Synthesis Example 1.

[0787] HRMS (70eV, EI+): m / z calcd for C18H4D8ClN: 285.1160, found: 285.

[0788] Elemental Analysis: C, 76%; H, 7%

[0789]

[0790] Synthesis Example 8: Synthesis of Intermediate I-6

[0791] [Reaction Equation 8]

[0792]

[0793] Intermediate I-6 (40.9g, 68%) was obtained using intermediate I-5 (45.49g, 159.2mmol) in the same manner as in Synthesis Example 2.

[0794] HRMS (70eV, EI+): m / z calcd for C24H16D8BNO2: 377.2402, found: 377.

[0795] Elemental Analysis: C, 76%; H, 9%

[0796]

[0797] Synthesis Example 9: Synthesis of Intermediate I-7

[0798] [Reaction Equation 9]

[0799]

[0800] Intermediate I-7 (27.0g, 56%) was obtained using intermediate I-6 (40.9g, 108.4mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (37.0g, 163 mmol) in the same manner as in Synthesis Example 3.

[0801] HRMS (70eV, EI+): m / z calcd for C27H9D8ClN4: 440.1644, found: 440.

[0802] Elemental Analysis: C, 74%; H, 6%

[0803]

[0804] Synthesis Example 10: Synthesis of Compound 27

[0805] [Reaction Equation 10]

[0806]

[0807] Compound 27 (27.7 g, 68%) was obtained using intermediate I-7 (27.0 g, 62.3 mmol) and 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (27.6 g, 74.8 mmol) in the same manner as in Synthesis Example 4.

[0808] HRMS (70eV, EI+): m / z calcd for C45H13D16N5: 655.3427, found: 655.

[0809] Elemental Analysis: C, 82%; H, 7%

[0810]

[0811] Synthesis Example 11: Synthesis of Intermediate I-8

[0812] [Reaction Equation 11]

[0813]

[0814] Intermediate I-8 (46.9g, 74%) was obtained using carbazole (46.1g, 275.6mmol) and 1-chloro-4-fluorobenzene (30.0g, 229.8 mmol) in the same manner as in Synthesis Example 1.

[0815] HRMS (70eV, EI+): m / z calcd for C18H12ClN: 277.0658, found: 277.

[0816] Elemental Analysis: C, 78%; H, 4%

[0817]

[0818] Synthesis Example 12: Synthesis of Intermediate I-9

[0819] [Reaction Equation 12]

[0820]

[0821] Intermediate I-9 (35.7g, 57%) was obtained using intermediate I-8 (46.9g, 169.0mmol) in the same manner as in Synthesis Example 2.

[0822] HRMS (70eV, EI+): m / z calcd for C24H24BNO2: 369.1900, found: 369.

[0823] Elemental Analysis: C, 78%; H, 7%

[0824]

[0825] Synthesis Example 13: Synthesis of Intermediate I-10

[0826] [Reaction Equation 13]

[0827]

[0828] Intermediate I-10 (13.48.0 g, 51%) was obtained using intermediate I-9 (22.6 g, 61.1 mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (20.7 g, 91.7 mmol) in the same manner as in Synthesis Example 3.

[0829] HRMS (70eV, EI+): m / z calcd for C27H17ClN4: 432.1142, found: 432.

[0830] Elemental Analysis: C, 75%; H, 4%

[0831]

[0832] Synthesis Example 14: Synthesis of Compound 33

[0833] [Reaction Equation 14]

[0834]

[0835] Compound 33 (12.3g, 89%) was obtained using intermediate I-10 (9.36g, 21.6mmol) and 9-(2-(4,4,5,5-tetramethyl1-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (9.57g, 25.9 mmol) in the same manner as in Synthesis Example 4.

[0836] HRMS (70eV, EI+): m / z calcd for C45H29N5: 639.2423, found: 639.

[0837] Elemental Analysis: C, 84%; H, 5%

[0838]

[0839] Synthesis Example 15: Synthesis of Intermediate I-11

[0840] [Reaction Equation 15]

[0841]

[0842] Intermediate I-11 (8.7g, 77%) was obtained using intermediate I-10 (10.0g, 23.1mmol) and 2-fluorophenylboronic acid (3.88, 27.7mmol) in the same manner as in Synthesis Example 4.

[0843] HRMS (70eV, EI+): m / z calcd for C33H21FN4: 492.1750, found: 492.

[0844] Elemental Analysis: C, 80%; H, 4%

[0845]

[0846] Synthesis Example 16: Synthesis of Compound 40

[0847] [Reaction Equation 16]

[0848]

[0849] Compound 40 (9.78 g, 77%) was obtained using intermediate I-11 (8.7 g, 17.7 mmol) and 4-phenyl-9H-carbazole (5.16 g, 21.2 mmol) in the same manner as in Synthesis Example 1.

[0850] HRMS (70eV, EI+): m / z calcd for C51H33N5: 715.2736, found: 715.

[0851] Elemental Analysis: C, 86%; H, 5%

[0852]

[0853] Synthesis Example 17: Synthesis of Intermediate I-12

[0854] [Reaction Equation 17]

[0855]

[0856] Intermediate I-12 (89.56 g, 66%) was obtained using 4-Phenyl-9H-carbazole (112.82 g, 45.9 mmol) and 1-chloro-4-fluorobenzene (50.0 g, 383.0 mmol) in the same manner as in Synthesis Example 1.

[0857] HRMS (70eV, EI+): m / z calcd for C24H16ClN: 353.0971, found: 353.

[0858] Elemental Analysis: C, 81%; H, 5%

[0859]

[0860] Synthesis Example 18: Synthesis of Intermediate I-13

[0861] [Reaction Equation 18]

[0862]

[0863] Intermediate I-13 (57.63g, 57%) was obtained using intermediate I-12 (80.0g, 226.1mmol) in the same manner as in Synthesis Example 2.

[0864] HRMS (70eV, EI+): m / z calcd for C24H24BNO2: 445.2213, found: 445.

[0865] Elemental Analysis: C, 81%; H, 6%

[0866]

[0867] Synthesis Example 19: Synthesis of Intermediate I-14

[0868] [Reaction Equation 19]

[0869]

[0870] Intermediate I-14 (43.7g, 66%) was obtained using intermediate I-13 (57.63g, 129.4mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (43.9g, 194.1 mmol) in the same manner as in Synthesis Example 3.

[0871] HRMS (70eV, EI+): m / z calcd for C27H17ClN4: 508.1455, found: 508.

[0872] Elemental Analysis: C, 78%; H, 4%

[0873]

[0874] Synthesis Example 20: Synthesis of Compound 44

[0875] [Reaction Equation 20]

[0876]

[0877] Compound 44 (24 g, 88%) was obtained using intermediate I-14 (20.0 g, 39.3 mmol) and 9-(2-(4,4,5,5-tetramethyl1-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (17.4 g, 47.2 mmol) in the same manner as in Synthesis Example 4.

[0878] HRMS (70eV, EI+): m / z calcd for C45H29N5: 715.2736, found: 715.

[0879] Elemental Analysis: C, 86%; H, 5%

[0880]

[0881] Synthesis Example 21: Synthesis of Compound C-4

[0882] [Reaction Equation 21]

[0883]

[0884] 10.0 g (24.5 mmol) of intermediate 9-1, 6.3 g (26.9 mmol) of intermediate 9-2, 31.1 g (1.2 mmol) of Pd2(dba), 3.5 g (36.7 mmol) of NaOtBu, and 30.7 g (3.7 mmol) of P(t-Bu) were placed in a round-bottom flask, 122 ml of Xylene was added, and the mixture was refluxed and stirred at 140 °C for 12 hours. After the reaction was finished, distilled water was added and stirred, the aqueous layer was removed, the organic layer was filtered through silica gel, and recrystallized to obtain 10.3 g (75%) of compound C-4.

[0885] (LC / MS Theoretical value: 560.23 g / mol, Measured value: M+= 561.54 g / mol)

[0886]

[0887] Synthesis Example 22: Synthesis of Compound B-136

[0888]

[0889] Compound B-136 was obtained by purchasing it from Gemchem.

[0890] HRMS (70eV, EI+): m / z calcd for C42H28N2: 560.2252, found: 560.

[0891] Elemental Analysis: C, 90%; H, 5%

[0892]

[0893] Synthesis Example 23: Synthesis of Compound R-1

[0894]

[0895] Compound R-1 was synthesized by referring to the synthesis method of patent WO2016159479.

[0896] HRMS (70eV, EI+): m / z calcd for C45H29N5: 639.2423, found: 639.

[0897] Elemental Analysis: C, 84%; H, 5%

[0898]

[0899] Synthesis Example 24: Synthesis of Compound R-2

[0900]

[0901] Compound R-2 was synthesized by referring to the synthesis method of patent WO2012108879.

[0902] HRMS (70eV, EI+): m / z calcd for C45H29N5: 639.2423, found: 639.

[0903] Elemental Analysis: C, 84%; H, 5%

[0904]

[0905] Synthesis Example 25: Synthesis of Compound R-3

[0906]

[0907] Compound R-3 was synthesized by referring to the synthesis method of Patent KR 2019-0004517 A.

[0908] HRMS (70eV, EI+): m / z calcd for C45H29N5: 791.3049, found: 791.

[0909] Elemental Analysis: C, 86%; H, 5%

[0910]

[0911] Synthesis Example 24: Synthesis of Compound R-4

[0912]

[0913] Compound R-4 was synthesized by referring to the synthesis method of patent KR 10-2023-0047925.

[0914] HRMS (70eV, EI+): m / z calcd for C51H23D8N5O: 737.3031, found: 737.

[0915] Elemental Analysis: C, 83%; H, 5%

[0916]

[0917] Example 1: Fabrication of a green organic light-emitting diode (single host)

[0918] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned using ultrasonic distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, a hole injection layer with a thickness of 100 Å was formed on the ITO substrate by vacuum deposition of Compound A doped with 3% NDP-9 (commercially available from Novaled), and a hole transport layer was formed by depositing Compound A with a thickness of 1350 Å on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing Compound B with a thickness of 350 Å on top of the hole transport layer. On top of the hole transport auxiliary layer, a 400 Å thick emissive layer was formed by vacuum deposition using Compound 1 as the host and doping with 7 wt% PhGD as the dopant. Next, compound C was deposited to a thickness of 50 Å on the upper surface of the light-emitting layer to form an electron transport assist layer, and compound D and Liq were vacuum-deposited simultaneously in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light-emitting diode was fabricated by sequentially vacuum-depositing LiQ 15 Å and Al 1200 Å on the upper surface of the electron transport layer to form a cathode.

[0919] It was fabricated with the structure ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound B (350Å) / EML[Host(Compound 1) : PhGD = 93wt% : 7wt%](400Å) / Compound C(50Å) / Compound D:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0920] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0921] Compound B: N-[4-(4-Dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0922] Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1'':3'',1''':3''',1''''-quinquephenyl]-3''''-yl)-1,3,5-triazine

[0923] Compound D: 2-(1,1'-Biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0924] [PhGD]

[0925]

[0926]

[0927] Examples 2 to 6, and Comparative Examples 1 to 4

[0928] An organic light-emitting diode was fabricated using the same method as in Example 1, except that the composition was changed to the one listed in Table 1 below.

[0929]

[0930] Example 7: Fabrication of a Green Organic Light Emitting Diode (Mixed Host)

[0931] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound E doped with 3% NDP-9 (commercially available from Novaled) on the ITO substrate, and a hole transport layer was formed by depositing compound E to a thickness of 1350 Å on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing compound F to a thickness of 320 Å on top of the hole transport layer. On the above hole transport assist layer, compound 1 and compound C-4 were simultaneously used as hosts in a weight ratio of 35:65 and doped with PhGD at 10 wt% as a dopant to form an emissive layer with a thickness of 380 Å by vacuum deposition. Subsequently, compound G was deposited to a thickness of 50 Å on the emissive layer to form an electron transport assist layer, and compound H and Liq were simultaneously vacuum deposited in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light-emitting diode was fabricated by sequentially vacuum depositing LiQ 15 Å and Al 1200 Å on the electron transport layer to form a cathode.

[0932] It was fabricated with the structure ITO / compound E (3% NDP-9 doping, 100Å) / compound E (1350Å) / compound F (320Å) / EML[Host(compound 1 : compound C-4 = 35 : 65 wt% / wt%) : PhGD = 90wt% : 10wt%](380Å) / compound G(50Å) / compound H:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0933] Compound E: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0934] Compound F: 9,9-dimethyl-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluoren-2-amine

[0935] Compound G: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0936] Compound H: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalene-2-yl}-4,6-diphenyl-1,3,5-triazine

[0937]

[0938] Examples 8 to 18, and Comparative Examples 5 to 10

[0939] An organic light-emitting diode was fabricated using the same method as in Example 7, except that the composition was changed to the one listed in Table 2 below.

[0940]

[0941] evaluation

[0942] The driving voltage and luminous efficiency of organic light-emitting diodes according to Examples 1 to 18 and Comparative Examples 1 to 10 were evaluated.

[0943] The specific measurement method is as follows, and the results are as shown in Tables 1 and 2.

[0944] (1) Measurement of change in current density according to voltage change

[0945] For the fabricated organic light-emitting diode, the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the result was obtained by dividing the measured current value by the area.

[0946] (2) Measurement of change in brightness according to voltage change

[0947] For the fabricated organic light-emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the results were obtained.

[0948] (3) Measurement of luminous efficiency

[0949] Using the luminance, current density, and voltage measured from (1) and (2) above, the same current density (10 mA / cm²) 2 The luminous efficiency (cd / A) of ) was calculated.

[0950] The luminous efficiency values ​​of Examples 1 to 6 and Comparative Examples 1 to 4 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0951] The luminous efficiency values ​​of Examples 7 to 18 and Comparative Examples 5 to 10 were calculated as relative values ​​based on Comparative Example 5 and are listed in Table 2 below.

[0952] (4) Driving voltage measurement

[0953] Using a current-voltage meter (Keithley 2400) at 15 mA / cm 2 The driving voltage of each component was measured to obtain the results.

[0954] The driving voltages of Examples 1 to 6 and Comparative Examples 1 to 4 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0955] The driving voltages of Examples 7 to 18 and Comparative Examples 5 to 10 were calculated as relative values ​​based on Comparative Example 5 and are listed in Table 2 below.

[0956] No. Compound (Wet%) Driving Voltage Luminous Efficiency (%) (%) Example 11 (10)91115 Example 28 (10)94117 Example 327 (10)91115 Example 433 (10)90111 Example 540 (10)92114 Example 644 (10)99112 Comparative Example 1 R-1 (10)100100 Comparative Example 2 R-2 (10)9690 Comparative Example 3 R-3 (10)9795 Comparative Example 4 R-4 (10)9588

[0957] No. Compound (Wt%) Driving Voltage Luminous Efficiency (%) (%) Example 7 1 / C-4 (35:65) 91 120 Example 8 8 / C-4 (35:65) 94 123 Example 9 8 / C-4 (4:6) 93 123 Example 10 8 / C-4 (45:55) 92 123 Example 11 27 / C-4 (35:65) 91 120 Example 12 33 / C-4 (35:65) 89 123 Example 13 33 / C-4 (4:6) 87 127 Example 14 33 / C-4 (45:55) 85 126 Example 15 40 / C-4 (35:65) 91 114 1640 / C-4(4:6)89116 Example 1740 / C-4(45:55)88119 Example 1844 / C-4(35:65)89118 Comparative Example 5 R-1 / C-4(35:65)100100 Comparative Example 6 R-1 / C-4(4:6)98105 Comparative Example 7 R-1 / C-4(45:55)97111 Comparative Example 8 R-2 / C-4(35:65)9784 Comparative Example 9 R-3 / C-4(35:65)9687 Comparative Example 10 R-4 / C-4(35:65)9581

[0958] Referring to Tables 1 and 2, it can be seen that the organic light-emitting diodes according to Examples 1 to 18 have improved driving voltage and luminous efficiency compared to the organic light-emitting diodes according to Comparative Examples 1 to 10.

[0959]

[0960] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention as defined in the following claims also fall within the scope of the present invention.

Claims

1. A compound for organic optoelectronic devices represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R 1 to R 4 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, and A1 and A2 are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuran or substituted or unsubstituted dibenzothiophene, and m1 to m4 are each independently one of integers 1 to 4, and When m1 to m4 is 2 or more, each R 1 to R 4 They are identical or different from each other.

2. In Paragraph 1, A compound for an organic optoelectronic device, wherein the above chemical formula 1 is represented by either the following chemical formula 1A or chemical formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] In the above chemical formulas 1A and 1B, R 1 to R 4 , Ar 1 , A1, A2, and m1 to m4 are as defined in Paragraph 1.

3. In Paragraph 1, A compound for an organic optoelectronic device, wherein the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-19: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] [Chemical Formula 1-17] [Chemical Formula 1-18] [Chemical Formula 1-19] In the above chemical formulas 1-1 to 1-19, R 1 to R 4 , Ar 1 , m1 to m4 are as defined in Paragraph 1, and X 1 and X 2 is independently O, S, or CR a R b And, R a and R b Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and R 5 to R 12 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and m5, m6, m8, m9, and m12 are each independently one of integers 1 to 4, and m7, m10, and m11 are each independently integers of 1 or 2.

4. In Paragraph 3, A compound for an organic optoelectronic device, wherein the above chemical formula 1 is represented by the above chemical formula 1-1.

5. In Paragraph 1, The above Ar 1 A compound for organic optoelectronic devices, wherein the compound is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

6. In Paragraph 1, A compound for organic optoelectronic devices selected from the compounds listed in Group 1 below: [Group 1] Dn represents the number of deuterium substitutions, and n is one of the integers from 1 to the maximum number of substitutions possible.

7. Comprising the first compound and the second compound, The above-mentioned first compound is a compound for an organic optoelectronic device according to claim 1, and The second compound is a composition for an organic optoelectronic device represented by the following chemical formula 2; a combination of the following chemical formulas 3 and 4; or the following chemical formula 5: [Chemical Formula 2] In the above chemical formula 2, R 13 to R 17 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 1 and L 2 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and m13, m16, and m17 are each independently one of integers 1 to 4, and m14 and m15 are each independently one of integers 1 to 3, and If m13 to m17 are 2 or more, each R 13 to R 17 are identical or different from each other, n is one of integers from 0 to 2; [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 3 and 4, Among a1* to a4* of Chemical Formula 3, two adjacent ones are each a connecting carbon (C) connected to * of Chemical Formula 4, and The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to Chemical Formula 4 are CL a -R a And, L a , L 3 and L 4 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and R a , R 18 and R 19 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and 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, and m18 and m19 are each independently one of integers 1 to 4, and If m18 and m19 are 2 or more, respectively R 18 and R 19 are identical or different from each other; [Chemical Formula 5] In the above chemical formula 5, L 5 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 20 to R 23 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and Ar 6 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m20, m22, and m23 are each independently one of integers 1 to 4, and m21 is one of integers from 1 to 3, and If m20 to m23 are 2 or more, each R 20 to R 23 They are identical or different from each other.

8. In Paragraph 7, The above chemical formula 2 is a composition for an organic optoelectronic device represented by the following chemical formula 2-8: [Chemical Formula 2-8] In the above chemical formula 2-8, R 13 to R 16 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and m13 and m16 are each independently one of integers 1 to 4, and m14 and m15 are each independently one of integers 1 to 3, and L 1 -Ar 2 and L 2 -Ar 3 Each is independently one of the substituents listed in Group I below, and [Group I] In the above Group I, R 24 to R 30 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and m24 is one of integers from 1 to 5, and m25 is one of integers from 1 to 4, and m26 is one of integers from 1 to 3, and m27 is an integer of 1 or 2, and m28 is one of integers from 1 to 7, and * is a connection point.

9. In Paragraph 7, The combination of the above chemical formulas 3 and 4 is a composition for an organic optoelectronic device represented by the following chemical formula 3C: [Chemical Formula 3C] In the above chemical formula 3C, L a3 and L a4 is a single bond, and R 18 , R 19 , R a3 and R a4 Each is independently hydrogen, deuterium, or a C6 to C12 aryl group, and m18 and m19 are each independently one of integers 1 to 4, and L 3 -Ar 4 and L 4 -Ar 5 Each is independently one of the substituents listed in Group I below, and [Group I] In the above Group I, R 24 to R 30 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and m24 is one of integers from 1 to 5, and m25 is one of integers from 1 to 4, and m26 is one of integers from 1 to 3, and m27 is an integer of 1 or 2, and m28 is one of integers from 1 to 7, and * is a connection point.

10. In Paragraph 7, The above first compound is represented by the following chemical formula 1-1, and A composition for an organic optoelectronic device, wherein the second compound is represented by the following chemical formula 3C: [Chemical Formula 1-1] In the above chemical formula 1-1, R 1 to R 6 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and Ar 1 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and m1 to m6 are each independently one of integers 1 to 4, and When m1 to m6 are 2 or more, each R 1 to R 6 They are identical or different from each other; [Chemical Formula 3C] In the above chemical formula 3C, L a3 and L a4 is a single bond, and L 3 and L 4 Each is independently a single bond or a substituted or unsubstituted phenylene group, and R 18 , R 19 , R a3 and R a4 Each is independently hydrogen, deuterium, or a C6 to C12 aryl group, and Ar 4 and Ar 5 Each is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and m18 and m19 are each independently one of integers 1 to 4, and When m18 and m19 are 2 or more, respectively R 18 to R 19 They are identical or different from each other.

11. Positive and negative poles facing each other, It includes at least one organic layer located between the anode and the cathode, and The above organic layer is a compound for an organic optoelectronic device according to any one of claims 1 to 6; or An organic optoelectronic device comprising a composition for an organic optoelectronic device according to any one of claims 7 to 10.

12. In Paragraph 11, The above organic layer includes a light-emitting layer, and The above-mentioned light-emitting layer is an organic optoelectronic device comprising the compound for the organic optoelectronic device or the composition for the organic optoelectronic device.

13. A display device comprising an organic optoelectronic element according to paragraph 11.

Images