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

Abstract

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

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0074707 filed in the Korean Intellectual Property Office on June 12, 2023, the entire contents of which are incorporated herein by reference. Technical Field

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

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

[0005] Organic optoelectronic devices can be roughly divided into two categories based on their working principles: one is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively; the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

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

[0007] Among them, organic light emitting diodes (OLEDs) have attracted attention in recent years due to the increasing demand for flat panel displays. Organic light emitting diodes convert electrical energy into light by applying current to organic light emitting materials, and the performance of organic light emitting diodes may be affected by organic materials disposed between electrodes. Summary of the invention

[0008] Some embodiments provide a compound for an organic optoelectronic device that can reduce driving voltage and achieve high efficiency and long lifespan.

[0009] Some embodiments provide an organic optoelectronic device including the compound for an organic optoelectronic device.

[0010] Some embodiments provide a display device including an organic optoelectronic device.

[0011] According to some embodiments, a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] X 1 is O, S or NL2 -Ar 2 ,

[0016] Among a1* to a4*, the adjacent two are connecting carbon atoms connected to *.

[0017] Among a1* to a4*, the remaining two not connected to * are each independently CL a -R a ,

[0018] L a and L 1 To L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0019] R a and R 1 To R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group,

[0020] Ar 1 To Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0021] m1 is an integer from 1 to 3,

[0022] D n represents the number of hydrogen substituted with deuterium, and n is an integer of 1 or more.

[0023] According to some embodiments, an organic optoelectronic device includes an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the organic layer includes a compound for an organic optoelectronic device.

[0024] According to some embodiments, a display device including an organic optoelectronic device is provided.

[0025] An organic optoelectronic device with high efficiency and long lifetime can be realized while reducing the driving voltage. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments.

[0027] <Description of Reference Numerals>

[0028] 100: Organic Light Emitting Diode

[0029] 105: Organic layer

[0030] 110: cathode

[0031] 120: Anode

[0032] 130: Luminous layer

[0033] 140: Hole transport region

[0034] 150: Electron transport region DETAILED DESCRIPTION

[0035] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0036] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0037] In one example of the present invention, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by: deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl or cyano. In addition, in a specific example of the present invention, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by: deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In addition, in a specific example of the present invention, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by: deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. Furthermore, in specific examples of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0038] As used herein, "unsubstituted" means that a hydrogen atom is not replaced with another substituent and that a hydrogen atom remains.

[0039] As used herein, "deuterium substitution (-D)" may include "tritium substitution (-T)".

[0040] As used herein, when a definition is not otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbons in one functional group.

[0041] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and may include a group in which all elements of the hydrocarbon aromatic portion have p orbitals forming a conjugation, such as phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic portions may be linked by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc., and a group in which two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl, etc.

[0042] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0043] As used herein, "heterocyclic group" has a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as an aryl, a cycloalkyl, a condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0044] For example, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings can be fused. When the heteroaryl is a fused ring, each ring can include one to three heteroatoms.

[0045] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be 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 tetraphenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-terphenyl group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0046] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted The invention may include, but is not limited to, a substituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzofuranofluorenyl, a substituted or unsubstituted benzothienofluorenyl, or a combination thereof, but is not limited thereto.

[0047] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0048] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level.

[0049] Hereinafter, a compound for an organic optoelectronic device according to some embodiments will be described.

[0050] The compound for an organic optoelectronic device according to some embodiments is represented by Chemical Formula 1.

[0051] [Chemical formula 1]

[0052]

[0053] In Chemical Formula 1,

[0054] X 1 is O, S or NL 2 -Ar 2 ,

[0055] Among a1* to a4*, the adjacent two are connecting carbon atoms connected to *.

[0056] Among a1* to a4*, the remaining two not connected to * are each independently CL a -R a ,

[0057] L a and L 1 To L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0058] R a and R 1 To R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0059] Ar 1 To Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0060] m1 is an integer from 1 to 3, and

[0061] D n represents the number of hydrogen substituted with deuterium, and n is an integer of 1 or more.

[0062] The compound represented by Chemical Formula 1 includes an indolecarbazole (or indole dibenzofuran or indole dibenzothiophene) skeleton and has a structure in which triazine is substituted by an indole ring. Compounds with this structure have bipolar properties, meaning that they can receive both holes and electrons when an electric field is applied. In particular, the electron cloud is widely diffused so that it has fast and stable electron transfer characteristics. In addition, due to steric hindrance, the molecular structure has a large reorganization energy (reorganization energy). Reorganization energy refers to the energy lost due to changes in molecular structure arrangement when moving charges, and the smaller the reorganization energy, the faster the charge mobility. Therefore, holes and electrons can move quickly, thereby improving driving voltage, efficiency and life characteristics. In addition, it has a high glass transition temperature and can be deposited at a relatively low temperature, so that it has excellent thermal stability.

[0063] In addition, the lifespan improvement effect can be maximized by a structure in which at least one deuterium is substituted. Upon deuterium substitution, the ground state energy can be reduced due to lower zero-point energy and lower vibration energy compared to hydrogen-bonded compounds, intermolecular interactions can be reduced, and a thin film can be prepared in an amorphous state, thereby more effectively improving the heat resistance and lifespan of an organic light-emitting diode using it. Therefore, the lifespan can be significantly improved by deuterium substitution.

[0064] In D n In , 'D' refers to deuterium, and 'n' refers to the number of substitutions.

[0065] More specifically, D n It refers to the number of hydrogens included in the compound represented by Chemical Formula 1 replaced by deuterium. As an example, 'D 15 ' means that 15 hydrogen atoms in the compound represented by Chemical Formula 1 are replaced by 15 deuterium atoms, 'D 16 ' means that 16 hydrogen atoms in the compound represented by Chemical Formula 1 are replaced by 16 deuterium atoms, and 'D 18 ' means that 18 hydrogens among hydrogens included in the compound represented by Chemical Formula 1 are replaced by 18 deuteriums.

[0066] Some of hydrogen included in the compound represented by Chemical Formula 1 may be substituted with deuterium, and all of hydrogen included in the compound represented by Chemical Formula 1 may be substituted with deuterium.

[0067] The hydrogen contained in the compound represented by Chemical Formula 1 refers to 'Ar 1 To Ar 4 ','L 1 To L 4 ','R 1 To R 5 ','L a ' and 'R a 'All the hydrogen present in.

[0068] When m1 is 2 or greater, each R 1 May be the same as or different from each other.

[0069] In some embodiments, the compound for an organic optoelectronic device may be represented by one of Chemical Formula 1A to Chemical Formula 1F.

[0070]

[0071]

[0072] In Chemical Formulae 1A to 1F,

[0073] X 1 , L 1, L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 and m1 is the same as above,

[0074] L a1 To L a4 Each independently of the above L a The definition is the same as

[0075] R a1 To R a4 Each independently of the above R a The definition is the same.

[0076] In some embodiments, Chemical Formula 1A may be represented by any one of Chemical Formula 1A-1 to Chemical Formula 1A-4.

[0077]

[0078]

[0079] In Chemical Formula 1A-1 to Chemical Formula 1A-4,

[0080] X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 、m1、L a1 , L a4 , R a1 and R a4 As mentioned above.

[0081] In some embodiments, Chemical Formula 1B may be represented by any one of Chemical Formula 1B-1 to Chemical Formula 1B-4.

[0082]

[0083]

[0084] In Chemical Formula 1B-1 to Chemical Formula 1B-4,

[0085] X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar3 ,Ar 4 , R 1 To R 5 、m1、L a1 , L a2 , R a1 and R a2 As mentioned above.

[0086] In some embodiments, Chemical Formula 1C may be represented by any one of Chemical Formula 1C-1 to Chemical Formula 1C-4.

[0087]

[0088]

[0089] In Chemical Formula 1C-1 to Chemical Formula 1C-4,

[0090] X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 、m1、L a3 , L a4 , R a3 and R a4 As mentioned above.

[0091] In some embodiments, Chemical Formula 1D may be represented by any one of Chemical Formula 1D-1 to Chemical Formula 1D-4.

[0092]

[0093] In Chemical Formula 1D-1 to Chemical Formula 1D-4,

[0094] X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 、m1、L a1 , L a4 , R a1 and R a4 As mentioned above.

[0095] In some embodiments, Chemical Formula 1E may be represented by any one of Chemical Formula 1E-1 to Chemical Formula 1E-4.

[0096]

[0097] In Chemical Formula 1E-1 to Chemical Formula 1E-4,

[0098] X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 、m1、L a3 , L a4 , R a3 and R a4 As mentioned above.

[0099] In some embodiments, Chemical Formula 1F may be represented by any one of Chemical Formula 1F-1 to Chemical Formula 1F-4.

[0100]

[0101]

[0102] In Chemical Formula 1F-1 to Chemical Formula 1F-4,

[0103] X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 、m1、L a1 , L a2 , R a1 and R a2 As mentioned above.

[0104] For example, the compound for an organic optoelectronic device may be represented by any one of Chemical Formula 1B-1, Chemical Formula 1B-4, Chemical Formula 1C-1, and Chemical Formula 1C-4.

[0105] For example, the compound for an organic optoelectronic device may be represented by Chemical Formula 1B-1 or Chemical Formula 1B-4.

[0106] For example, L 1 and L 2 Each independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0107] For example, Ar1 and Ar 2 Each of them may independently 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, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilyl group.

[0108] For example, L 1 -Ar 1 and L 2 -Ar 2 The substituents listed in Group I may be each independently selected.

[0109] [Group I]

[0110]

[0111] In Group I,

[0112] R 23 To R 25 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl,

[0113] m23 is an integer from 1 to 5,

[0114] m24 is an integer from 1 to 4,

[0115] m25 is an integer from 1 to 3, and

[0116] * is the connection point.

[0117] When m23 is 2 or greater, each R 23 May be the same as or different from each other.

[0118] When m24 is 2 or greater, each R 24 May be the same as or different from each other.

[0119] When m25 is 2 or more, each R 25 May be the same as or different from each other.

[0120] For example, L a1 To L a4 , L 3 and L 4 Each independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0121] For example, Ar 3 and Ar 4Each of them may independently 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 phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted carbazolyl group.

[0122] For example, L 3 -Ar 3 and L 4 -Ar 4 The substituents listed in Group II may be each independently selected.

[0123] [Group II]

[0124]

[0125] In Group II,

[0126] R 26 To R 28 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl,

[0127] m26 is an integer from 1 to 5,

[0128] m27 is an integer from 1 to 4,

[0129] m28 is an integer from 1 to 3, and

[0130] * is the connection point.

[0131] When m26 is 2 or greater, each R 26 May be the same as or different from each other.

[0132] When m27 is 2 or greater, each R 27 May be the same as or different from each other.

[0133] When m28 is 2 or greater, each R 28 May be the same as or different from each other.

[0134] For example, R a1 To R a4 and R 1 To R 5 Each may independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C2 to C18 heterocyclic group, or a combination thereof.

[0135] For example, R a1To R a4 and R 1 To R 5 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted carbazolyl.

[0136] In some embodiments of the present invention, the deuterium substitution rate may be greater than or equal to 30%.

[0137] More specifically, the deuterium substitution rate may be greater than or equal to 40%, greater than or equal to 50%, greater than or equal to 60%, greater than or equal to 70%, greater than or equal to 80%, or greater than or equal to 90%.

[0138] In this specification, the deuterium substitution rate refers to the ratio of deuterium to hydrogen when the total number of positions in a compound where hydrogen can be replaced by deuterium is 100%. The deuterium substitution rate can be determined by calculating the ratio of the deuterium substitution rate before and after the deuterium substitution. H The molecular weight can be calculated by the integrated value of the NMR peak or by confirmation of the molecular weight by LC / MS.

[0139] For example, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1, but is not limited thereto.

[0140] [Group 1]

[0141]

[0142]

[0143]

[0144]

[0145] (D n refers to the number of hydrogens replaced by deuterium and represents structures having one or more deuterium substitutions).

[0146] The compound for an organic optoelectronic device may be a composition further including a dopant.

[0147] The dopant may be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0148] A dopant is a material mixed in a small amount with a compound used for an organic optoelectronic device to cause light emission, and is generally a material such as a metal complex that emits light by multiple excitations to a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0149] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0150] [Chemical formula Z]

[0151] L 5 MX 2

[0152] In the chemical formula Z, M is a metal, L is 5 and X 2 are the same or different and are ligands that form a complex with M.

[0153] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 5 and X 2 This may be, for example, a bidentate ligand.

[0154] By L 5 and X 2 Examples of the ligand represented by may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0155] [Group A]

[0156]

[0157] In Group A,

[0158] R 300 To R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen, C6 to C30 aryl which may be substituted by C1 to C30 alkyl, or halogen, and

[0159] R 303 To R 324Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, 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.

[0160] For example, it may include a dopant represented by Chemical Formula V.

[0161] [Chemical Formula V]

[0162]

[0163] In chemical formula V,

[0164] R 101 To R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0165] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0166] R 101 To R 116 At least one of them is a functional group represented by the chemical formula V-1,

[0167] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of a carbon or heteroatom, and

[0168] m21 and m22 are each independently any one of integers from 0 to 3 and m21+m22 is any one of integers from 1 to 3,

[0169] [Chemical formula V-1]

[0170]

[0171] In chemical formula V-1,

[0172] R 135 To R 139are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,and

[0173] * indicates a moiety attached to a carbon atom.

[0174] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0175] [Chemical formula Z-1]

[0176]

[0177] In the chemical formula Z-1, rings A, B, C and D are independently 5-membered or 6-membered carbocyclic or heterocyclic rings;

[0178] R A , R B , R C and R D are independently mono-, di-, tri- or tetra-substituted or unsubstituted;

[0179] L B , L C and L D Each is independently selected from direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0180] nA is 0 or 1;

[0181] When nA is 1, L E is selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof; when nA is 0, L E does not exist; and

[0182] R A , R B , R C , R D R, R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino and combinations thereof; any adjacent R A , R B , R C , R D, R and R' are optionally linked to each other to provide a ring; X B , X C , X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a direct bond.

[0183] The dopant according to some embodiments may be a platinum complex, and may be represented, for example, by Chemical Formula VI.

[0184] [Chemical Formula VI]

[0185]

[0186] In Chemical Formula VI,

[0187] X 100 Selected from O, S and NR 131 ,

[0188] R 117 To R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0189] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0190] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl, and

[0191] R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0192] Hereinafter, an organic optoelectronic device using the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device will be described.

[0193] The organic optoelectronic device may be any device that converts electrical energy into optical energy, or vice versa, without particular limitation, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, an organic photosensitive drum, and the like.

[0194] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0195] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments.

[0196] Reference Figure 1 , an organic light emitting diode 100 according to some embodiments includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0197] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; 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) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0198] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0199] The organic layer 105 may include the above-described compound for an organic optoelectronic device.

[0200] The organic layer 105 includes a light emitting layer 130, and the light emitting layer 130 may include the above-mentioned compound for an organic optoelectronic device. For example, the compound for an organic optoelectronic device may be a phosphorescent host.

[0201] The composition further comprising a dopant may be, for example, a green light emitting composition.

[0202] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0203] The charge transport region may be, for example, a hole transport region 140 .

[0204] The hole transport region 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0205] 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 of group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0206] [Group B]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] (Dn refers to the number of hydrogens replaced by deuterium and denotes structures having one or more deuterium substitutions).

[0214] In the hole transporting region 140, in addition to these compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds similar thereto can be used.

[0215] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0216] The electron transport region 150 may further increase electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0217] 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 of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0218] [Group C]

[0219]

[0220]

[0221]

[0222]

[0223] Some embodiments may be an organic light emitting diode including a light emitting layer as an organic layer.

[0224] Some embodiments may be an organic light emitting diode including a light emitting layer and a hole transporting region as organic layers.

[0225] Some embodiments may be an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0226] like Figure 1 As shown, the organic light emitting diode according to some embodiments may further include a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130 .

[0227] On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as the above-mentioned organic layer in addition to the light emitting layer.

[0228] The organic light emitting diode 100 may be produced by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0229] The organic light emitting diode may be applied to an organic light emitting display device.

[0230] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0231] Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry or P&H Tech or synthesized by known methods unless otherwise specified.

[0232] (Preparation of Compounds for Organic Optoelectronic Devices)

[0233] Synthesis Example 1: Synthesis of Intermediate I-1

[0234] [Reaction 1]

[0235]

[0236] In a nitrogen environment, 20 g (73.2 mmol) of 12H-benzo [4,5] thieno [2,3-a] carbazole compound, 32.3 ml (365.8 mmol) of trifluoromethanesulfonic acid, and 700 ml (7316.6 mmol) of D6-benzene were heated at 80° C. for 24 hours and stirred under reflux. When the reaction was completed, after adding pure water thereto, the organic layer obtained therefrom was neutralized with a saturated potassium phosphate solution, concentrated, and column purified to obtain intermediate I-1 (14 g, 70%).

[0237] HRMS (70 eV, EI+): m / z calculated for C18HD10NS: 283.1240, measured: 283.

[0238] Synthesis Example 2: Synthesis of Compound R-1

[0239] [Reaction 2]

[0240]

[0241] In a nitrogen environment, 14g (49.4mmol) of intermediate I-1 was dissolved in 500ml of N, N-dimethylformamide. Subsequently, 1.8g (74.1mmol) of sodium hydride was added thereto, and then stirred for 30 minutes. Then, 19.8g (74.1mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was added thereto, and then stirred at room temperature for 12 hours. When the reaction was completed, after adding pure water thereto, the solid produced therein was filtered under reduced pressure and separated. The solid was dissolved in toluene and recrystallized to obtain compound R-1 (18g, 71%).

[0242] HRMS (70 eV, EI+): m / z calculated for C33H10D10N4S: 514.2036, measured: 514.

[0243] Synthesis Example 3: Synthesis of Intermediate I-2

[0244] [Reaction 3]

[0245]

[0246] In a nitrogen environment, 50g (135.4mmol) of 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole was dissolved in 600ml of tetrahydrofuran, and 38.4g (162.5mmol) of 1-bromo-3-chloro-2-nitrobenzene and 7.8g (6.8mmol) of tetrakis (triphenylphosphine) palladium were added thereto, and then stirred. Subsequently, 46.8g (338.5mmol) of a saturated aqueous solution of potassium carbonate was added thereto, and then heated at 80°C for 12 hours and stirred under reflux. When the reaction was completed, after water was added to the reaction solution, the mixture was extracted with dichloromethane, treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-2 (40g, 74%).

[0247] HRMS (70 eV, EI+): m / z calculated for C24H15ClN2O2: 398.0822, measured: 398.

[0248] Synthesis Example 4: Synthesis of Intermediate I-3

[0249] [Reaction 4]

[0250]

[0251] In a nitrogen environment, 40g (100.3mmol) of intermediate I-2 and 78.9g (300.9mmol) of triphenylphosphine were dissolved in 500ml of 1,2-dichlorobenzene and then heated at 200°C for 12 hours. When the reaction was complete, after water was added to the reaction solution, the mixture was extracted with dichloromethane, treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-3 (30g, 82%).

[0252] HRMS (70 eV, EI+): m / z calculated for C24H15ClN2: 366.0924, measured: 366.

[0253] Synthesis Example 5: Synthesis of Intermediate I-4

[0254] [Reaction 5]

[0255]

[0256] In a nitrogen environment, 30g (81.8mmol) of intermediate I-3, 24.9g (98.1mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 2.3g (2.5mmol) of tris(dibenzylideneacetone)dipalladium, 5.5g (19.6mmol) of tricyclohexylphosphine and 12.0g (122.7mmol) of potassium acetate were dissolved in 800ml of toluene, then heated at 120°C for 12 hours and stirred under reflux. When the reaction was complete, after water was added to the reaction solution, the organic layer was extracted therefrom, treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-4 (30g, 80%).

[0257] HRMS (70 eV, EI+): m / z calculated for C30H27BN2O2: 458.2166, measured: 458.

[0258] Synthesis Example 6: Synthesis of Intermediate I-5

[0259] [Reaction 6]

[0260]

[0261] In the same manner as in Synthesis Example 3, by using 30 g (65.5 mmol) of Intermediate I-4 and 27 g (78.5 mmol) of 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine, Intermediate I-5 (35 g, 84%) was obtained.

[0262] HRMS (70 eV, EI+): m / z calculated for C45H29N5: 639.2423, measured: 639.

[0263] Synthesis Example 7: Synthesis of Intermediate I-6

[0264] [Reaction 7]

[0265]

[0266] In a nitrogen environment, 35g (54.7mmol) of intermediate I-5, 33.5g (164.1mmol) of iodobenzene, 2.1g (10.9mmol) of copper iodide, 11.3g (82.1mmol) of potassium carbonate and 20.5g (82.1mmol) of 3,5-di-tert-butyl salicylic acid were dissolved in 550ml of dodecylbenzene, then heated at 180°C for 12 hours and stirred at reflux. When the reaction was complete, after water was added to the reaction solution, the organic layer was extracted therefrom, treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-6 (20g, 51%).

[0267] HRMS (70 eV, EI+): m / z calculated for C51H33N5: 715.2736, measured: 715.

[0268] Synthesis Example 8: Synthesis of Compound A-1

[0269] [Reaction formula 8]

[0270]

[0271] In the same manner as in Synthesis Example 1, Compound A-1 (15 g, 75%) was obtained by using 20 g (27.9 mmol) of Intermediate I-6.

[0272] HRMS (70 eV, EI+): m / z calculated for C51H15D18N5: 733.39, measured: 733.

[0273] Synthesis Example 9: Synthesis of Intermediate I-7

[0274] [Reaction formula 9]

[0275]

[0276] In the same manner as in Synthesis Example 3, by using 50 g (135.4 mmol) of 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole) and 38.4 g (162.5 mmol) of 2-bromo-1-chloro-3-nitrobenzene, intermediate I-7 (41 g, 76%) was obtained.

[0277] HRMS (70 eV, EI+): m / z calculated for C24H15ClN2O2: 398.0822, measured: 398.

[0278] Synthesis Example 10: Synthesis of Intermediate I-8

[0279] [Reaction formula 10]

[0280]

[0281] In the same manner as in Synthesis Example 4, Intermediate I-8 (30 g, 80%) was obtained by using 41 g (102.8 mmol) of Intermediate I-7.

[0282] HRMS (70 eV, EI+): m / z calculated for C24H15ClN2: 366.0924, measured: 366.

[0283] Synthesis Example 11: Synthesis of Intermediate I-9

[0284] [Reaction formula 11]

[0285]

[0286] In the same manner as in Synthesis Example 5, Intermediate I-9 (20 g, 53%) was obtained by using 30 g (81.8 mmol) of Intermediate I-8.

[0287] HRMS (70 eV, EI+): m / z calculated for C30H27BN2O2: 458.2166, measured: 458.

[0288] Synthesis Example 12: Synthesis of Intermediate I-10

[0289] [Reaction 12]

[0290]

[0291] In the same manner as in Synthesis Example 3, Intermediate I-10 (25 g, 90%) was obtained by using 20 g (43.6 mmol) of Intermediate I-9 and 22.5 g (65.5 mmol) of 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0292] HRMS (70 eV, EI+): m / z calculated for C45H29N5: 639.2423, measured: 639.

[0293] Synthesis Example 13: Synthesis of Intermediate I-11

[0294] [Reaction 13]

[0295]

[0296] In a nitrogen environment, 25g (39.1mmol) of intermediate I-10, 9.2g (58.6mmol) of bromobenzene, 1.8g (2.0mmol) of tri (dibenzylideneacetone) dipalladium, 4.8ml (9.8mmol) of tri-tert-butylphosphine and 4.51g (46.9mmol) of sodium tert-butoxide were dissolved in 400ml of toluene, then heated at 120°C for 12 hours and stirred at reflux. When the reaction was complete, after water was added to the reaction solution, an organic layer was extracted therefrom, treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-11 (25g, 89%).

[0297] HRMS (70 eV, EI+): m / z calculated for C51H33N5: 715.2736, measured: 715.

[0298] Synthesis Example 14: Synthesis of Compound A-30

[0299] [Reaction 14]

[0300]

[0301] In the same manner as in Synthesis Example 1, compound A-30 (20 g, 80%) was obtained by using 25 g (34.9 mmol) of intermediate I-11.

[0302] HRMS (70 eV, EI+): m / z calculated for C51H15D18N5: 733.39, measured: 733.

[0303] Synthesis Example 15: Synthesis of Intermediate I-12

[0304] [Reaction 15]

[0305]

[0306] In the same manner as in Synthesis Example 3, Intermediate I-12 (30 g, 75%) was obtained by using 30 g (121.4 mmol) of 4-bromodibenzo[b,d]furan and 23.6 g (145.7 mmol) of 2,6-dichloroaniline.

[0307] HRMS (70 eV, EI+): m / z calculated for C18H11Cl2NO: 327.0218, found: 327.

[0308] Synthesis Example 16: Synthesis of Intermediate I-13

[0309] [Reaction 16]

[0310]

[0311] In a nitrogen environment, 30g (91.4mmol) of intermediate I-12 was dissolved in 900ml of N, N-dimethylacetamide (DMAc), and 1.0g (4.6mmol) of palladium acetate, 25.3g (182.8mmol) of potassium carbonate and 3.37g (9.1mmol) of tricyclohexylphosphine tetrafluoroborate were added thereto, and then heated at 200°C for 12 hours and stirred at reflux. When the reaction was completed, after water was added to the reaction solution, the organic layer was extracted therefrom, treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-13 (15g, 56%).

[0312] HRMS (70 eV, EI+): m / z calculated for C18H10ClNO: 291.0451, found: 291.

[0313] Synthesis Example 17: Synthesis of Intermediate I-14

[0314] [Reaction 17]

[0315]

[0316] In the same manner as in Synthesis Example 5, Intermediate I-14 (10 g, 51%) was obtained by using 15 g (51.4 mmol) of Intermediate I-13.

[0317] HRMS (70 eV, EI+): m / z calculated for C24H22BNO3: 383.1693, measured: 383.

[0318] Synthesis Example 18: Synthesis of Intermediate I-15

[0319] [Reaction 18]

[0320]

[0321] In the same manner as in Synthesis Example 3, Intermediate I-15 (12 g, 81%) was obtained by using 10 g (26.1 mmol) of Intermediate I-14 and 13.5 g (39.1 mmol) of 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0322] HRMS (70 eV, EI+): m / z calculated for C39H24N4O: 564.1950, found: 564.

[0323] Synthesis Example 19: Synthesis of Intermediate I-16

[0324] [Reaction 19]

[0325]

[0326] In the same manner as in Synthesis Example 7, Intermediate I-16 (7 g, 51%) was obtained by using 12 g (21.3 mmol) of Intermediate I-15.

[0327] HRMS (70 eV, EI+): m / z calculated for C45H28N4O: 640.2236, measured: 640.

[0328] Synthesis Example 20: Synthesis of Compound A-68

[0329] [Reaction 20]

[0330]

[0331] In the same manner as in Synthesis Example 1, compound A-68 (5 g, 71%) was obtained by using 7 g (10.9 mmol) of intermediate I-16.

[0332] HRMS (70 eV, EI+): m / z calculated for C45H13D15N4O: 655.32, found: 655.

[0333] Synthesis Example 21: Synthesis of Intermediate I-17

[0334] [Reaction 21]

[0335]

[0336] In the same manner as in Synthesis Example 3, Intermediate I-17 (25 g, 63%) was obtained by using 30 g (121.4 mmol) of 4-bromodibenzo[b,d]furan and 23.6 g (145.7 mmol) of 2,3-dichloroaniline.

[0337] HRMS (70 eV, EI+): m / z calculated for C18H11Cl2NO: 327.0218, found: 327.

[0338] Synthesis Example 22: Synthesis of Intermediate I-18

[0339] [Reaction 22]

[0340]

[0341] In the same manner as in Synthesis Example 16, Intermediate I-18 (10 g, 45%) was obtained by using 25 g (76.2 mmol) of Intermediate I-17.

[0342] HRMS (70 eV, EI+): m / z calculated for C18H10ClNO2: 291.0451, measured: 291.

[0343] Synthesis Example 23: Synthesis of Intermediate I-19

[0344] [Reaction 23]

[0345]

[0346] In the same manner as in Synthesis Example 5, Intermediate I-19 (8 g, 61%) was obtained by using 10 g (34.3 mmol) of Intermediate I-18.

[0347] HRMS (70 eV, EI+): m / z calculated for C24H22BNO3: 383.1693, measured: 383.

[0348] Synthesis Example 24: Synthesis of Intermediate I-20

[0349] [Reaction 24]

[0350]

[0351] In the same manner as in Synthesis Example 3, Intermediate I-20 (9 g, 76%) was obtained by using 8 g (20.9 mmol) of Intermediate I-19 and 10.8 g (31.3 mmol) of 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0352] HRMS (70 eV, EI+): m / z calculated for C39H24N4O: 564.1950, found: 564.

[0353] Synthesis Example 25: Synthesis of Intermediate I-21

[0354] [Reaction 25]

[0355]

[0356] In the same manner as in Synthesis Example 13, Intermediate I-21 (9.5 g, 93%) was obtained by using 9 g (15.9 mmol) of Intermediate I-20.

[0357] HRMS (70 eV, EI+): m / z calculated for C45H28N4O: 640.2236, measured: 640.

[0358] Synthesis Example 26: Synthesis of Compound A-71

[0359] [Reaction 26]

[0360]

[0361] In the same manner as in Synthesis Example 1, compound A-71 (8 g, 84%) was obtained by using 9.5 g (14.8 mmol) of intermediate I-21.

[0362] HRMS (70 eV, EI+): m / z calculated for C45H13D15N4O: 655.32, found: 655.

[0363] Synthesis Example 27: Synthesis of Intermediate I-22

[0364] [Reaction 27]

[0365]

[0366] In the same manner as in Synthesis Example 3, Intermediate I-22 (23 g, 87%) was obtained by using 20 g (80.9 mmol) of 2-bromodibenzo[b,d]furan and 15.7 g (97.13 mmol) of 2,6-dichloroaniline.

[0367] HRMS (70 eV, EI+): m / z calculated for C18H11Cl2NO: 327.0218, found: 327.

[0368] Synthesis Example 28: Synthesis of Intermediate I-23

[0369] [Reaction 28]

[0370]

[0371] In the same manner as in Synthesis Example 16, Intermediate I-23 (15 g, 73%) was obtained by using 23 g (70.1 mmol) of Intermediate I-22.

[0372] HRMS (70 eV, EI+): m / z calculated for C18H10ClNO: 291.0451, found: 291.

[0373] Synthesis Example 29: Synthesis of Intermediate I-24

[0374] [Reaction 29]

[0375]

[0376] In the same manner as in Synthesis Example 5, Intermediate I-24 (13 g, 66%) was obtained by using 15 g (51.4 mmol) of Intermediate I-23.

[0377] HRMS (70 eV, EI+): m / z calculated for C24H22BNO3: 383.1693, measured: 383.

[0378] Synthesis Example 30: Synthesis of Intermediate I-25

[0379] [Reaction formula 30]

[0380]

[0381] In the same manner as in Synthesis Example 3, Intermediate I-25 (15 g, 78%) was obtained by using 13 g (33.9 mmol) of Intermediate I-24 and 17.5 g (50.9 mmol) of 2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0382] HRMS (70 eV, EI+): m / z calculated for C39H24N4O: 564.1950, found: 564.

[0383] Synthesis Example 31: Synthesis of Intermediate I-26

[0384] [Reaction 31]

[0385]

[0386] In the same manner as in Synthesis Example 7, 15 g (26.6 mmol) of Intermediate I-25 was used to obtain Intermediate I-26 (13 g, 76%).

[0387] HRMS (70 eV, EI+): m / z calculated for C45H28N4O: 640.2263, measured: 640.

[0388] Synthesis Example 32: Synthesis of Compound A-72

[0389] [Reaction 32]

[0390]

[0391] In the same manner as in Synthesis Example 1, 13 g (20.3 mmol) of Intermediate I-26 was used to obtain Compound A-72 (10 g, 77%).

[0392] HRMS (70 eV, EI+): m / z calculated for C45H12D16N4O: 656.33, measured: 656.

[0393] Manufacturing of organic light-emitting diodes

[0394] Example 1

[0395] A glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form A hole injection layer is formed on the hole injection layer to a thickness of Compound B is deposited on the hole transport layer to a thickness of The hole transport auxiliary layer was formed by using the compound A-1 synthesized in Synthesis Example 8 as a host on the hole transport auxiliary layer and doped with 9 wt % of PhGD as a dopant by vacuum deposition to form In the following examples and comparative examples, the ratios are described separately. Subsequently, compound C is deposited to form a light-emitting layer on the light-emitting layer. A thick electron transport auxiliary layer is formed, and compound D and LiQ are simultaneously vacuum deposited at a weight ratio of 1:1 to form On the electron transport layer, LiQ and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0396] The structure is ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[Compound A-1 (91 wt%):PhGD (9 wt%)] / Compound C / Compound D:LiQ / LiQ / Al

[0397] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0398] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0399] Compound C: 2,4-diphenyl-6-(4',5',6'-triphenyl[1,1':2',1":3",1"':3"',1""-pentaphenyl]-3""-yl)-1,3,5-triazine

[0400] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0401] [PhGD]

[0402]

[0403] Example 2 and Comparative Examples 1 to 3

[0404] Organic light emitting diodes were manufactured in the same manner as in Example 1, except that the compositions were changed to those shown in Tables 1 to 3.

[0405] evaluate

[0406] The luminous efficiency and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 2 and Comparative Examples 1 to 3 were evaluated.

[0407] The specific measurement method is as follows, and the results are shown in Tables 1 to 3.

[0408] (1) Measuring the change in current density due to voltage change

[0409] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit diode in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0410] (2) Measuring the change in brightness due to voltage changes

[0411] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0412] (3) Measurement of luminous efficiency

[0413] Using the luminance and current density measured according to (1) and (2) above, calculate the same current density (10 mA / cm 2 ) under current efficiency (cd / A).

[0414] Based on Comparative Example 1, the luminous efficiency values ​​of Examples 1 to 2 and Comparative Example 1 were calculated as relative values ​​and are listed in Table 1.

[0415] (4) Measurement life

[0416] By converting the brightness (cd / m 2 ) maintained at 24000cd / m 2 The results were obtained by measuring the time it takes for the current efficiency (cd / A) to drop to 90%.

[0417] Based on Comparative Examples 2 and 3, the life measurement values ​​of Examples 1 to 2 and Comparative Examples 2 to 3 were calculated as relative values ​​and are listed in Tables 2 and 3.

[0418] (Table 1)

[0419] serial number main body efficiency(%) Example 1 Compound A-1 107％ Example 2 Compound A-68 108％ Comparative Example 1 Compound R-1 100％

[0420] (Table 2)

[0421] serial number main body Lifespan T90(%) Example 1 Compound A-1 113％ Comparative Example 2 Intermediate I-6 100％

[0422] (Table 3)

[0423] serial number main body Lifespan T90(%) Example 2 Compound A-68 111％ Comparative Example 3 Intermediate I-16 100％

[0424] Referring to Table 1, the luminous efficiency of the organic light-emitting diodes according to Examples 1 to 2 is significantly improved compared to the organic light-emitting diode according to Comparative Example 1. The triazine and fused carbazole according to Comparative Example 1 are connected in the N direction, allowing free rotation. Compared with the structure of the present invention, the molecular structure has a higher reorganization energy value. Reorganization energy refers to the energy lost due to changes in the molecular structure arrangement when moving charges, and the smaller the reorganization energy, the faster the charge mobility. Due to these characteristics, Examples 1 and 2 exhibit higher efficiency characteristics compared to Comparative Example 1. In addition, referring to Tables 2 and 3, the lifespan of the organic light-emitting diodes according to Examples 1 and 2 is significantly improved compared to the organic light-emitting diodes according to Comparative Examples 2 and 3. This increases the bond dissociation energy caused by deuterium substitution, thereby increasing the stability of the compound, and the lifespan characteristics can be improved when the compound is used in an organic light-emitting diode.

[0425] While the present invention has been described in conjunction with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical formula 1] In Chemical Formula 1, X 1 is O, S or NL 2 -Ar 2 , In a 1 * to a 4 In *, the two adjacent carbon atoms are connected to *. In a 1 * to a 4 *, the other two not connected to * are CL a -R a , L a and L 1 To L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a and R 1 To R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 1 To Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 is an integer from 1 to 3, and D n represents the number of hydrogen substituted with deuterium, and n is an integer of 1 or more.

2. The compound for an organic optoelectronic device according to claim 1, in, The compound is represented by any one of Chemical Formula 1A to Chemical Formula 1F: In Chemical Formulae 1A to 1F, X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 and m1 is defined in claim 1, L a1 To L a4 Each independently of L defined in claim 1 a The definition of is the same as R a1 To R a4 Each independently of R defined in claim 1 a The definition is the same.

3. The compound for an organic optoelectronic device according to claim 1, in, The compound is represented by any one of Chemical Formula 1B-1, Chemical Formula 1B-4, Chemical Formula 1C-1 and Chemical Formula 1C-4: In Chemical Formula 1B-1, Chemical Formula 1B-4, Chemical Formula 1C-1 and Chemical Formula 1C-4, X 1 , L 1 , L 3 , L 4 ,Ar 1 ,Ar 3 ,Ar 4 , R 1 To R 5 and m1 is defined in claim 1, L a1 To L a4 Each independently of L defined in claim 1 a The definition of is the same as R a1 To R a4 Each independently of R defined in claim 1 a The definition is the same.

4. The compound for an organic optoelectronic device according to claim 3, wherein The compound is represented by Chemical Formula 1B-1 or Chemical Formula 1B-4.

5. The compound for an organic optoelectronic device according to claim 1, in, Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl or a substituted or unsubstituted dibenzosilyl.

6. The compound for an organic optoelectronic device according to claim 1, in, L 1 -Ar 1 and L 2 -Ar 2 Each is independently selected from the substituents listed in Group I: [Group I] In Group I, R 23 To R 25 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m23 is an integer from 1 to 5, m24 is an integer from 1 to 4, m25 is an integer from 1 to 3, and * is the connection point.

7. The compound for an organic optoelectronic device according to claim 1, in, Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl or a substituted or unsubstituted carbazolyl.

8. The compound for an organic optoelectronic device according to claim 1, in, L 3 -Ar 3 and L 4 -Ar 4 Each is independently selected from the substituents listed in Group II: [Group II] In Group II, R 26 To R 28 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m26 is an integer from 1 to 5, m27 is an integer from 1 to 4, m28 is an integer from 1 to 3, and * is the connection point.

9. The compound for an organic optoelectronic device according to claim 1, in, The deuterium substitution rate is greater than or equal to 30%.

10. The compound for an organic optoelectronic device according to claim 1, in, The compound is one selected from the compounds listed in Group 1: [Group 1] 11. An organic optoelectronic device, include: an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, The organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 10.

12. The organic optoelectronic device according to claim 11, in, The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic optoelectronic device. 13 . A display device comprising the organic optoelectronic device according to claim 11 or 12.

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