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

Abstract

The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. The compound is represented by the following Chemical Formula 1. [Chemical Formula 1] # imgabs0 #

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0151077 filed in the Korean Intellectual Property Office on November 3, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments of the present invention relate to 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 basically divided into two categories according to 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, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

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

[0007] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by organic materials between electrodes. Summary of the invention

[0008] The embodiment may be implemented by providing a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1:

[0009] [Chemical formula 1]

[0010]

[0011] In chemical formula 1, X 1 O or S, R 1 and R 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, R 3 To R 6 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, L 1is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, Ar 1 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 is an integer of 1 or 2, m2 and m3 are each independently an integer of 1 to 3, and m4 is an integer of 1 to 4.

[0012] The embodiments may be implemented by providing an organic optoelectronic device including an anode and a cathode facing each other; and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes a compound for an organic optoelectronic device.

[0013] Embodiments may be implemented by providing a display device including an organic optoelectronic device. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Features will become apparent to those skilled in the art by describing in detail exemplary embodiments with reference to the accompanying drawings, in which:

[0015] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments. DETAILED DESCRIPTION

[0016] Example embodiments will now be described more fully below with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments described herein. Rather, these embodiments are provided so that the present disclosure will be thorough and complete for those skilled in the art and will fully convey exemplary implementations.

[0017] In the accompanying drawings, the sizes of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it may be directly on the other layer or substrate, or there may also be an intermediate layer. In addition, it will be understood that when a layer is referred to as being "under" another layer, it may be directly below, and there may also be one or more intermediate layers. In addition, it will be understood that when a layer is referred to as being "between" two layers, it may be the only layer between the two layers, or there may also be one or more intermediate layers. The same reference numerals always represent the same elements. As used herein, the term "or" is not necessarily an exclusive term, for example, "A or B" will include A, B, or A and B.

[0018] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with 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.

[0019] In one example, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound 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 a specific example, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific example, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific example, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0020] "Unsubstituted" means that a hydrogen atom is not replaced with another substituent and that a hydrogen atom remains.

[0021] In the present specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)". For example, any hydrogen in any compound described herein may be protium, deuterium or tritium (e.g., based on natural or artificial substitution).

[0022] As used herein, when a definition is not otherwise provided, "hetero" refers to a group including 1 to 3 heteroatoms selected from N, O, S, P and Si in one functional group and the remainder being carbon.

[0023] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and all elements of the hydrocarbon aromatic portion have p-orbitals forming conjugation, such as phenyl, naphthyl, etc., two or more hydrocarbon aromatic portions may be connected by a σ bond and the hydrocarbon aromatic portion may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic portions may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0024] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0025] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si to replace carbon (C) in cyclic compounds, such as aryl, cycloalkyl, condensed rings thereof or combinations thereof. In one embodiment, the heterocyclic group may be a condensed ring, and all or each ring of the heterocyclic group may include one or more heteroatoms.

[0026] For example, "heteroaryl" may represent an aryl group comprising 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 may be fused. In one embodiment, the heteroaryl group may be a fused ring, and each ring may include 1 to 3 heteroatoms.

[0027] For example, 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 naphthyl 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 substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, substituted or unsubstituted furanyl, or a combination thereof.

[0028] For example, the substituted or unsubstituted C2 to C30 heterocyclic group may be 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 benzothiophenyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted substituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzopropanoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted benzothiophenopyrimidinyl, or a combination thereof.

[0029] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) level.

[0030] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) level, electrons formed in the cathode can be easily injected into the light-emitting layer due to the conductive property and transported in the light-emitting layer.

[0031] Hereinafter, a compound for an organic optoelectronic device according to some embodiments is described.

[0032] The compound for an organic optoelectronic device according to some embodiments may be represented by Chemical Formula 1.

[0033]

[0034] In chemical formula 1, X 1 Can be O or S.

[0035] R 1 and R 2 Each independently may be or include, for example, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

[0036] R 3 To R 6 Each independently may be or include, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.

[0037] L 1 It may be or include, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0038] Ar 1 It may be or include, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0039] m1 may be an integer such as 1 or 2.

[0040] m2 and m3 may each independently be an integer of 1 to 3, for example.

[0041] m4 can be an integer from 1 to 4.

[0042] The compound represented by Chemical Formula 1 may have a structure in which dibenzofuran (or dibenzothiophene) is substituted with two tert-butyl groups and fluorene is substituted with amine, and has fast hole migration to improve charge balance, and thus may reduce a driving voltage of an organic light emitting diode applied thereto and may achieve a longer lifespan.

[0043] The compound in which one benzene ring of dibenzofuran (or dibenzothiophene) is simultaneously substituted by two tert-butyl groups can be a low refractive index material to improve the efficiency of an organic light emitting diode.

[0044] In one embodiment, Chemical Formula 1 may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-6.

[0045]

[0046] In Chemical Formulae 1-1 to 1-6, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0047] In one embodiment, Chemical Formula 1-1 may be represented by one of Chemical Formula 1-1A, Chemical Formula 1-1B, Chemical Formula 1-1C, or Chemical Formula 1-1D.

[0048]

[0049]

[0050] In Chemical Formula 1-1A, Chemical Formula 1-1B, Chemical Formula 1-1C and Chemical Formula 1-1D, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0051] In one embodiment, Chemical Formula 1-2 may be represented by one of Chemical Formula 1-2A, Chemical Formula 1-2B, Chemical Formula 1-2C, or Chemical Formula 1-2D.

[0052]

[0053]

[0054] In Chemical Formula 1-2A, Chemical Formula 1-2B, Chemical Formula 1-2C and Chemical Formula 1-2D, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0055] Chemical Formula 1-3 may be represented by one of Chemical Formula 1-3A, Chemical Formula 1-3B, Chemical Formula 1-3C, or Chemical Formula 1-3D.

[0056]

[0057] In Formula 1-3A, Formula 1-3B, Formula 1-3CC and Formula 1-3D, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1. Chemical Formula 1-4 may be represented by one of Chemical Formula 1-4A, Chemical Formula 1-4B, Chemical Formula 1-4C, or Chemical Formula 1-4D.

[0058]

[0059] In Chemical Formula 1-4A, Chemical Formula 1-4B, Chemical Formula 1-4C and Chemical Formula 1-4D, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0060] Chemical Formula 1-5 may be represented by one of Chemical Formula 1-5A, Chemical Formula 1-5B, Chemical Formula 1-5C, or Chemical Formula 1-5D.

[0061]

[0062]

[0063] In Chemical Formula 1-5A, Chemical Formula 1-5B, Chemical Formula 1-5C and Chemical Formula 1-5D, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0064] Chemical Formula 1-6 may be represented by one of Chemical Formula 1-6A, Chemical Formula 1-6B, Chemical Formula 1-6C, or Chemical Formula 1-6D.

[0065]

[0066] In Chemical Formula 1-6A, Chemical Formula 1-6B, Chemical Formula 1-6C and Chemical Formula 1-6D, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0067] In one embodiment, Chemical Formula 1 may be represented by one of Chemical Formula 1-1A, Chemical Formula 1-2A, Chemical Formula 1-3A, Chemical Formula 1-4A, Chemical Formula 1-5A, or Chemical Formula 1-6A.

[0068] In one embodiment, Chemical Formula 1-1A may be represented by one of Chemical Formula 1-1A-1 to Chemical Formula 1-1A-4.

[0069]

[0070] In Chemical Formulae 1-1A-1 to 1-1A-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0071] In one embodiment, Chemical Formula 1-2A may be represented by one of Chemical Formula 1-2A-1 to Chemical Formula 1-2A-4.

[0072]

[0073]

[0074] In Chemical Formulas 1-2A-1 to 1-2A-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0075] In one embodiment, Chemical Formula 1-3A may be represented by one of Chemical Formula 1-3A-1 to Chemical Formula 1-3A-4.

[0076]

[0077] In Chemical Formulas 1-3A-1 to 1-3A-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0078] In one embodiment, Chemical Formula 1-4A may be represented by one of Chemical Formula 1-4A-1 to Chemical Formula 1-4A-4.

[0079]

[0080]

[0081] In Chemical Formula 1-4A-1 to Chemical Formula 1-4A-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0082] In one embodiment, Chemical Formula 1-5A may be represented by one of Chemical Formula 1-5A-1 to Chemical Formula 1-5A-4.

[0083]

[0084]

[0085] In Chemical Formulas 1-5A-1 to 1-5A-4, X 1 、R1 1 To R 6 , L 1,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0086] In one embodiment, Chemical Formula 1-6A may be represented by one of Chemical Formula 1-6A-1 to Chemical Formula 1-6A-4.

[0087]

[0088] In Chemical Formulas 1-6A-1 to 1-6A-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0089] In one embodiment, Chemical Formula 1-1B may be represented by one of Chemical Formula 1-1B-1 to Chemical Formula 1-1B-4.

[0090]

[0091]

[0092] In Chemical Formulas 1-1B-11 to 1-1B-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0093] In one embodiment, Chemical Formula 1-2B may be represented by one of Chemical Formula 1-2B-1 to Chemical Formula 1-2B-4.

[0094]

[0095]

[0096] In Chemical Formulas 1-2B-1 to 1-2B-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0097] In one embodiment, Chemical Formula 1-3B may be represented by one of Chemical Formula 1-3B-1 to Chemical Formula 1-3B-4.

[0098]

[0099] In Chemical Formula 1-3B-1 to Chemical Formula 1-3B-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0100] In one embodiment, Chemical Formula 1-4B may be represented by one of Chemical Formula 1-4B-1 to Chemical Formula 1-4B-4.

[0101]

[0102]

[0103] In Chemical Formula 1-4B-1 to Chemical Formula 1-4B-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0104] In one embodiment, Chemical Formula 1-5B may be represented by one of Chemical Formula 1-5B-1 to Chemical Formula 1-5B-4.

[0105]

[0106]

[0107] In Chemical Formula 1-5B-1 to Chemical Formula 1-5B-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0108] In one embodiment, Chemical Formula 1-6B may be represented by one of Chemical Formula 1-6B-1 to Chemical Formula 1-6B-4.

[0109]

[0110] In Chemical Formulas 1-6B-1 to 1-6B-4, X 1 、R1 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0111] In one embodiment, Chemical Formula 1-1C may be represented by one of Chemical Formula 1-1C-1 to Chemical Formula 1-1C-4.

[0112]

[0113]

[0114] In Chemical Formulae 1-1C-1 to 1-1C-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0115] In one embodiment, Chemical Formula 1-2C may be represented by one of Chemical Formulas 1-2C-1 to 1-2C-4,

[0116]

[0117]

[0118] In Chemical Formulae 1-2C-1 to 1-2C-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0119] In one embodiment, Chemical Formula 1-3C may be represented by one of Chemical Formula 1-3C-1 to Chemical Formula 1-3C-4.

[0120]

[0121] In Chemical Formulae 1-3C-1 to 1-3C-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0122] In one embodiment, Chemical Formula 1-4C may be represented by one of Chemical Formula 1-4C-1 to Chemical Formula 1-4C-4.

[0123]

[0124]

[0125] In Chemical Formula 1-4C-1 to Chemical Formula 1-4C-4, X1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0126] In one embodiment, Chemical Formula 1-5C may be represented by any one of Chemical Formula 1-5C-1 to Chemical Formula 1-5C-4.

[0127]

[0128]

[0129] In Chemical Formulae 1-5C-1 to 1-5C-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0130] In one embodiment, Chemical Formula 1-6C may be represented by one of Chemical Formula 1-6C-1 to Chemical Formula 1-6C-4.

[0131]

[0132] In Chemical Formulae 1-6C-1 to 1-6C-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0133] In one embodiment, Chemical Formula 1-1D may be represented by one of Chemical Formula 1-1D-1 to Chemical Formula 1-1D-4.

[0134]

[0135]

[0136] In Chemical Formulae 1-1D-1 to 1-1D-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0137] In one embodiment, Chemical Formula 1-2D may be represented by one of Chemical Formula 1-2D-1 to Chemical Formula 1-2D-4.

[0138]

[0139]

[0140] In Chemical Formula 1-2D-1 to Chemical Formula 1-2D-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0141] In one embodiment, Chemical Formula 1-3D may be represented by one of Chemical Formula 1-3D-1 to Chemical Formula 1-3D-4.

[0142]

[0143] In Chemical Formula 1-3D-1 to Chemical Formula 1-3D-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0144] In one embodiment, Chemical Formula 1-4D may be represented by one of Chemical Formula 1-4D-1 to Chemical Formula 1-4D-4.

[0145]

[0146] In Chemical Formula 1-4D-1 to Chemical Formula 1-4D-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0147] In one embodiment, Chemical Formula 1-5D may be represented by one of Chemical Formula 1-5D-1 to Chemical Formula 1-5D-4.

[0148]

[0149]

[0150] In Chemical Formula 1-5D-1 to Chemical Formula 1-5D-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0151] In one embodiment, Chemical Formula 1-6D may be represented by one of Chemical Formula 1-6D-1 to Chemical Formula 1-6D-4.

[0152]

[0153] In Chemical Formulae 1-6C-1 to 1-6C-4, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 may be the same as defined in Chemical Formula 1.

[0154] In one embodiment, Chemical Formula 1 may be represented by, for example, Chemical Formula 1-2A, Chemical Formula 1-2B, Chemical Formula 1-2C, Chemical Formula 1-5A, Chemical Formula 1-5B, or Chemical Formula 1-5C.

[0155] In one embodiment, Chemical Formula 1 may be represented by, for example, Chemical Formula 1-2A-2, Chemical Formula 1-2A-3, Chemical Formula 1-2B-2, Chemical Formula 1-2C-2, Chemical Formula 1-5A-2, or Chemical Formula 1-5C-2.

[0156] In one embodiment, 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, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiorol group, a substituted or unsubstituted benzonaphthofuranyl group or a substituted or unsubstituted benzonaphthothiophenyl group.

[0157] In one embodiment, L 1 It may be or include, for example, a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0158] In one embodiment, the moiety -L 1 -Ar 1 Can be part of group I for example.

[0159] [Group I]

[0160]

[0161] In Group I, R 9 To R 12Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0162] R 13 and R 14 Each independently may be, for example, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.

[0163] m5 may be an integer from 1 to 5, for example.

[0164] m6 can be an integer from 1 to 4, for example.

[0165] m7 may be an integer from 1 to 3, for example.

[0166] m8 can be an integer such as 1 or 2,

[0167] * is the connection point.

[0168] In one embodiment, m5 can be 2, 3, 4 or 5, and each R 9 Can be the same as or different from each other.

[0169] In one embodiment, m6 can be 2, 3 or 4, and each R 10 Can be the same as or different from each other.

[0170] In one embodiment, m7 can be 2 or 3, and each R 11 May be the same as or different from each other.

[0171] In one embodiment, m8 may be 2, and each R 12 May be the same as or different from each other.

[0172] In one embodiment, R 1 and R 2 Each of them independently may be, for example, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a combination thereof.

[0173] In one embodiment, R 3 To R 6 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0174] In one embodiment, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be, for example, a compound of Group 1.

[0175] [Group 1]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185] In the compounds of Group 1, Dn (eg, D26) indicates the number of deuterium atoms contained, and indicates a structure in which hydrogen (protium) is substituted with one or more deuterium atoms.

[0186] In addition to the above compounds for organic optoelectronic devices, one or more compounds may be included. In one embodiment, a dopant may be further included. 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.

[0187] The dopant may be a substance that emits light when mixed in a small amount in a compound or composition for an organic optoelectronic device, and may generally be a material that emits light by being excited multiple times to a triplet state or more, such as a metal complex. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and may be included in one or two or more types.

[0188] In one embodiment, the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may include an organic metal compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may use, for example, a compound represented by the chemical formula Z.

[0189] [Chemical formula Z]

[0190] L 2 MX 2

[0191] In the chemical formula Z, M may be a metal, and L 2 and X 2Each may independently be a ligand that forms a complex with M.

[0192] 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 9 and X may be, for example, a bidentate ligand.

[0193] By L 2 and X 2 Examples of the ligands represented may include group A ligands.

[0194] [Group A]

[0195]

[0196] In group A, R 300 To R 302 Each independently may be, for example, hydrogen, deuterium, a C1 to C30 alkyl group which may be substituted or unsubstituted by a halogen, a C6 to C30 aryl group which may be substituted or unsubstituted by a C1 to C30 alkyl group, or a halogen.

[0197] R 303 To R 324 Each of them may independently be, for example, 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.

[0198] n1 may be an integer from 1 to 5, for example.

[0199] n2 may be an integer from 1 to 4, for example.

[0200] n3 may be an integer from 1 to 3, for example.

[0201] n4 may be an integer such as 1 or 2.

[0202] n5 may be an integer of 1 to 6, for example.

[0203] In one embodiment, n1 may be 2, 3, 4 or 5, and each substituent may be the same as or different from each other.

[0204] In one embodiment, n2 may be 2, 3 or 4, and each substituent may be the same or different from each other.

[0205] In one embodiment, n3 may be 2 or 3, and each substituent may be the same or different from each other.

[0206] In one embodiment, n4 may be 2, and each substituent may be the same or different from each other.

[0207] In one embodiment, n5 can be 2, 3, 4, 5, 6, and each substituent can be the same or different from each other.

[0208] The dopant according to some embodiments may be an iridium complex, and may be represented by, for example, Chemical Formula 6-1 or Chemical Formula 6-2.

[0209] [Chemical formula 6-1]

[0210]

[0211] In Chemical Formula 6-1, R 101 To R 116 may be 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 .

[0212] R 132 To R 134 Each independently may be a substituted or unsubstituted C1 to C6 alkyl group.

[0213] In one embodiment, R 101 To R 116 At least one of them may be a functional group represented by Chemical Formula V-1.

[0214] L 100 The bidentate ligand may be a monovalent anion and may be a ligand coordinated to iridium via a lone electron pair of carbon or a heteroatom.

[0215] m19 and m20 may each independently be an integer from 0 to 3, and m19+m20 may be an integer from 1 to 3.

[0216] [Chemical formula V-1]

[0217]

[0218] In chemical formula V-1, R 135 To R 139may be 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 .

[0219] * indicates a moiety attached to a carbon atom.

[0220] [Chemical formula 6-2]

[0221]

[0222] In chemical formula 6-2, R 101 To R 117 may be each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -Si R 133 R 134 R 135 .

[0223] R 133 To R 135 Each independently may be a substituted or unsubstituted C1 to C6 alkyl group.

[0224] L 100 The bidentate ligand may be a monovalent anion and may be a ligand coordinated to iridium via a lone electron pair of carbon or a heteroatom.

[0225] n1 and n2 may each independently be an integer from 0 to 3, and n1+n2 may be an integer from 1 to 3.

[0226] In one embodiment, it may include a dopant represented by Chemical Formula Z-1.

[0227] [Chemical formula Z-1]

[0228]

[0229] In the chemical formula Z-1, the rings A, B, C and D may each independently be a 5-membered or 6-membered carbocyclic ring or a heterocyclic ring.

[0230] R A , R B , R C and R D Each may independently be mono-, di-, tri- or tetra-substituted or unsubstituted.

[0231] L B , L C and L DEach may independently be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0232] In one embodiment, nA is 1, L E It can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof. In one embodiment, nA is 0, and L E Does not exist.

[0233] R A , R B , R C , R D , R and R' can each independently be hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, cyano, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino or a combination thereof. In one embodiment, adjacent R A , R B , R C , R D , R and R' may be separated or may be linked to each other to provide a ring; X B , X C , X D and X E can each independently be carbon or nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Can each independently be oxygen or a direct bond.

[0234] The platinum complex may be represented, for example, by Chemical Formula 7-1 or Chemical Formula 7-2.

[0235] [Chemical formula 7-1]

[0236]

[0237] [Chemical formula 7-2]

[0238]

[0239] In Chemical Formula 7-1 and Chemical Formula 7-2, X 100 Can be O, S or NR 132 .

[0240] R 118 To R 132may be each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0241] R 133 To R 135 Each independently may be a substituted or unsubstituted C1 to C6 alkyl group.

[0242] In one embodiment, R 118 To R 132 At least one of them may be -SiR 133 R 134 R 135 or tert-butyl.

[0243] R 133 To R 135 Each independently may be a substituted or unsubstituted C1 to C6 alkyl group.

[0244] Hereinafter, an organic optoelectronic device to which the above-mentioned compound for an organic optoelectronic device may be applied will be described.

[0245] The organic optoelectronic device may be any suitable device that converts electrical energy into light energy (or vice versa), and it may be, for example, an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photoconductor.

[0246] Herein, an organic light emitting diode is described as one example of an organic optoelectronic device with reference to the accompanying drawings.

[0247] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments.

[0248] 1 , an organic light emitting diode 100 according to some embodiments may include an anode 120 and a cathode 110 facing each other, and an organic layer 105 between the anode 120 and the cathode 110 .

[0249] 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, etc., or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; 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.

[0250] 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, or BaF2 / Ca.

[0251] The organic layer 105 may include the above-mentioned compound for an organic optoelectronic device. The organic layer 105 may include a light-emitting layer 130, and the light-emitting layer 130 may include the above-mentioned compound for an organic optoelectronic device.

[0252] The light emitting layer 130 may include a composition for an organic optoelectronic device, the composition further including a dopant. The composition for an organic optoelectronic device may be, for example, a green light emitting composition.

[0253] The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host. In addition to the light emitting layer, the organic layer may further include a charge transport region.

[0254] The charge transport region may be, for example, a hole transport region 140. The hole transport region 140 may help to further improve hole injection or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0255] In one embodiment, 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, wherein the hole transport auxiliary layer may include the above-mentioned compound for an organic optoelectronic device. In one embodiment, the light emitting layer may include a host and a dopant, and the host may be, for example, a phosphorescent host.

[0256] The phosphorescent host can promote the injection and transmission of holes and electrons in the light-emitting layer, and finally make holes and electrons meet to form excitons, and will be able to transfer the formed exciton energy to the dopant. The example of the phosphorescent host can include organic compounds, which include, for example, carbazole, indolecarbazole, dibenzofuran, dibenzothiophene, indole dibenzopyran, indole dibenzothiophene, fluorene, indenyl carbazole, triphenylene, pyrimidine, triazine or a combination thereof. The phosphorescent host can be any suitable material. In one embodiment, it can be a single host or a mixed host.

[0257] In one embodiment, the above compound for an organic optoelectronic device may be included in the light emitting layer, and the compound of group C may be included in at least one layer of a hole transport layer and a hole transport auxiliary layer.

[0258] [Group C]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265] (Dn represents the number of deuterium substituted, and represents a structure substituted with one or more deuteriums)

[0266] In the hole transport region 140 , other suitable compounds may be included in addition to the above-mentioned compounds.

[0267] In one embodiment, the charge transport region may be, for example, an electron transport region 150. The electron transport region 150 may also help improve electron injection or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0268] In one embodiment, 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 located between the light emitting layer 130 and the electron transport layer, and the compound of group D may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0269] [Group D]

[0270]

[0271]

[0272]

[0273] Some embodiments may provide an organic light emitting diode including a light emitting layer as an organic layer.

[0274] Some embodiments may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.

[0275] Some embodiments may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.

[0276] In addition to the light emitting layer 130, the organic light emitting diode according to some embodiments may include a hole transport region 140 and an electron transport region 150 as the organic layer 105, such as Figure 1 shown.

[0277] In one embodiment, in addition to the light-emitting layer, the organic light-emitting diode according to some embodiments may further include an electron injection layer, a hole injection layer, etc. as the above-mentioned organic layer.

[0278] The organic light emitting diode 100 can be produced by forming an anode or 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 anode thereon. The above-mentioned organic light emitting diode can be applied to an organic light emitting diode display device.

[0279] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it will be understood that the examples and comparative examples should not be considered as limiting the scope of the embodiments, nor should the comparative examples be considered outside the scope of the embodiments. In addition, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0280] Hereinafter, unless otherwise specified, the starting materials and reactants used in the Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry or P&H tech, or were synthesized by a suitable method.

[0281] (Preparation of Compounds for Organic Optoelectronic Devices)

[0282] Synthesis Example 1: Synthesis of Compound 1-7

[0283]

[0284] 10.0 g (31.76 mmol) of the intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b, d]furan, 13.78 g (38.11 mmol) of the intermediate of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, 6.01 g (63.52 mmol) of sodium tert-butylate and 0.771 g (1.9 mmol) of tri-tert-butylphosphine were dissolved in 317 ml of toluene, and 0.87 g (0.95 mmol) of Pd2(dba)3 was added thereto, and then refluxed and stirred for 12 hours under a nitrogen atmosphere. After the reaction was completed, the organic layer extracted therefrom with ethyl acetate and distilled water was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product thus obtained was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio 3:1) to obtain the target compound, 16.8 g (yield: 83%) of Compound 1-7 as a white solid.

[0285] Theoretical value: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0286] Analytical values: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0287] Synthesis Example 2: Synthesis of Compound 1-11

[0288]

[0289] Compound 1-11 (13.2 g, yield: 81%) was synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of the intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 11.02 g of the intermediate of N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0290] Theoretical value: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0291] Analytical values: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0292] Synthesis Example 3: Synthesis of Compound 1-22

[0293]

[0294] Compound 1-22 (16.7 g, yield: 79%) was synthesized in the same manner as in Synthesis Example 1, except that 9.0 g of the intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 15.9 g of the intermediate of 9,9-dimethyl-N-(3-(9-methyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0295] Theoretical value: C, 89.03; H, 6.93; N, 1.89; O, 2.16

[0296] Analytical values: C, 89.03; H, 6.93; N, 1.89; O, 2.16

[0297] Synthesis Example 4: Synthesis of Compound 1-29

[0298]

[0299] Compound 1-29 (12.4 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 7.0 g of the intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 10.71 g of the intermediate of bis(9,9-dimethyl-9H-fluoren-2-yl)amine were used in an equivalent ratio of 1:1.2.

[0300] Theoretical values: C, 88.32; H, 7.26; N, 2.06; O, 2.35

[0301] Analytical values: C, 88.32; H, 7.26; N, 2.06; O, 2.35

[0302] Synthesis Example 5: Synthesis of Compound 1-37

[0303]

[0304] Compound 1-37 (16.7 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate of 2,4-di-tert-butyl-8-chlorodibenzo[b,d]furan and 13.78 g of the intermediate of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0305] Theoretical value: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0306] Analytical values: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0307] Synthesis Example 6: Synthesis of Compound 1-54

[0308]

[0309] Compound 1-54 (19.9 g, yield: 78%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate of 2,4-di-tert-butyl-8-chlorodibenzo[b,d]furan and 20.04 g of the intermediate of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0310] Theoretical value: C, 89.62; H, 6.64; N, 1.74; O, 1.99

[0311] Analytical values: C, 89.62; H, 6.64; N, 1.74; O, 1.99

[0312] Synthesis Example 7: Synthesis of Compound 1-80

[0313]

[0314] Compound 1-80 (14.5 g, yield: 81%) was synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of the intermediate of 2,4-di-tert-butyl-7-chlorodibenzo[b,d]furan and 12.98 g of the intermediate of N-(9,9-dimethyl-9H-fluoren-2-yl)naphtho[1,2-b]benzofuran-7-amine were used in an equivalent ratio of 1:1.2.

[0315] Theoretical value: C, 87.02; H, 6.44; N, 1.99; O, 4.55

[0316] Analytical values: C, 87.02; H, 6.44; N, 1.99; O, 4.55

[0317] Synthesis Example 8: Synthesis of Compound 1-129

[0318]

[0319] Compound 1-129 (12.3 g, yield: 76%) was synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of the intermediate of 6,8-di-tert-butyl-1-chlorodibenzo[b,d]furan and 11.02 g of the intermediate of N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-3-amine were used in an equivalent ratio of 1:1.2.

[0320] Theoretical value: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0321] Analytical values: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0322] Synthesis Example 9: Synthesis of Compound 1-205

[0323]

[0324] Compound 1-205 (18.4 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate of 1,3-di-tert-butyl-9-chlorodibenzo[b,d]furan and 15.16 g of the intermediate of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0325] Theoretical value: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0326] Analytical values: C, 88.22; H, 7.09; N, 2.19; O, 2.50

[0327] Synthesis Example 10: Synthesis of Compound 1-223

[0328]

[0329] Compound 1-223 (17.0 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate of 1,3-di-tert-butyl-9-chlorodibenzo[b,d]furan and 14.31 g of the intermediate of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:1.2.

[0330] Theoretical value: C, 86.34; H, 6.63; N, 2.14; O, 4.89

[0331] Analytical values: C, 86.34; H, 6.62; N, 2.14; O, 4.89

[0332] Synthesis Example 11: Synthesis of Compound 1-269

[0333]

[0334] Compound 1-269 (14.9 g, yield: 80%) was synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of the intermediate of 1,3-di-tert-butyl-7-chlorodibenzo[b,d]furan and 13.77 g of the intermediate of N-(9,9-dimethyl-9H-fluoren-2-yl)-4-phenyldibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:1.2.

[0335] Theoretical values: C, 87.21; H, 6.49; N, 1.92; O, 4.38

[0336] Analytical values: C, 87.21; H, 6.49; N, 1.92; O, 4.38

[0337] Comparative Synthesis Example 1: Synthesis of Compound R-1

[0338]

[0339] Compound R-1 (27.6 g, yield: 76%) was synthesized in the same manner as in Synthesis Example 1, except that 15.0 g of the intermediate of 7-(tert-butyl)-1-chlorodibenzo[b,d]furan and 27.93 g of the intermediate of bis(9,9-dimethyl-9H-fluoren-2-yl)amine were used in an equivalent ratio of 1:1.2.

[0340] Theoretical values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0341] Analytical values: C, 88.57; H, 6.62; N, 2.25; O, 2.56

[0342] Comparative Synthesis Example 2: Synthesis of Compound R-2

[0343]

[0344] Compound R-2 (13.4 g, yield: 72%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of the intermediate of 1,3-di-tert-butyl-6-(3-chlorophenyl)dibenzo[b,d]furan and 11.4 g of the intermediate of N-([1,1'-biphenyl]-4-yl)-8,10-dihydropyrene-4-amine were used in an equivalent ratio of 1:1.2.

[0345] Theoretical value: C, 89.34; H, 6.53; N, 1.93; O, 2.20

[0346] Analytical values: C, 89.34; H, 6.53; N, 1.93; O, 2.20

[0347] (Production of organic light-emitting diodes)

[0348] Example 1

[0349] The glass substrate coated with ITO / Ag / ITO was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with acetone or isopropyl alcohol and dried, then moved to a plasma cleaner, cleaned for 10 minutes by using oxygen plasma, and moved to a vacuum depositor. The prepared ITO / Ag / ITO (reflective electrode) was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO / Ag / ITO substrate to form - a thick hole injection layer, and depositing compound A on the hole injection layer to The compound 1-7 obtained in Synthesis Example 1 was deposited on the hole transport layer to a thickness of 100 to 1000 nm. On the hole transport auxiliary layer, 85 wt % of the host H1 (40%) and the host H2 (60%) were used as the host, and 15 wt % of PtGD was doped as a dopant by vacuum deposition to form a hole transport auxiliary layer. Subsequently, compound C is deposited to form a light-emitting layer on the light-emitting layer. -thick electron transport auxiliary layer, and compound D and Liq are simultaneously vacuum deposited in a ratio of 1:1 to form -Thick electron transport layer. On the electron transport layer, Yb and AgMg are sequentially vacuum deposited to produce an organic light-emitting diode.

[0350] The structure is ITO / Ag / ITO / compound A (3% NDP-9 doping, ) / Compound A / Hole transport auxiliary layer / Emitting layer [host (host H1, host H2): GD = 85wt%: 15wt%] / Compound C / Compound D: Liq / Yb / AgMg.

[0351] Compound A: N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine

[0352] Compound C: 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0353] Compound D: 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)

[0354] Host H1: 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(triphenylene-2-yl)phenyl)-1,3,5-triazine

[0355] Host H2: 9,9"-diphenyl-9H,9"H-3,3':9',3"-tricarbazole

[0356]

[0357] Examples 2 to 11 and Comparative Examples 1 to 2

[0358] Diodes of Examples 2 to 11 and Comparative Examples 1 to 2 were produced in the same manner as in Example 1, except that the composition of the hole transport auxiliary layer was changed as shown in Table 1.

[0359] evaluate

[0360] (1) Measuring the change in current density due to voltage change

[0361] The resulting organic light emitting diode was measured for a current value flowing into the unit device while increasing the voltage from 0 V to 10 V using a voltammeter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0362] (2) Measuring the change in brightness due to voltage changes

[0363] While the voltage of the organic light emitting diode was increased from 0 V to 10 V, the luminance was measured using a photometer (Minolta Cs-1000A).

[0364] (3) Measurement of luminous efficiency

[0365] Using the luminance and current density measured according to (1) and (2) above, at the same current density (10 mA / cm 2 )Calculate the luminous efficiency (cd / A).

[0366] Table 1 shows relative values ​​of luminous efficiency based on Comparative Example 1.

[0367] (4) Lifespan measurement

[0368] By converting the brightness (cd / m 2 ) maintained at 24,000cd / m 2 The results were obtained by measuring the time it takes for the current efficiency (cd / A) to drop to 97%.

[0369] Table 1 shows the relative values ​​based on the lifetime measurement of Comparative Example 1.

[0370] (Table 1)

[0371]

[0372] Referring to Table 1, the efficiency characteristics and lifespan characteristics of the organic light emitting diode to which the compound according to the embodiment was applied were significantly improved compared with the organic light emitting diode according to the comparative example.

[0373] Some embodiments may provide a compound for an organic optoelectronic device that can realize an organic optoelectronic device with low driving, high efficiency, and long lifetime.

[0374] Some embodiments may provide an organic optoelectronic device including the compound for an organic optoelectronic device.

[0375] Some embodiments may provide a display device including an organic optoelectronic device.

[0376] An organic optoelectronic device having high efficiency and long lifetime can be realized.

[0377] Example embodiments have been disclosed herein, and although specific terms are used, these terms will be used and understood only in a general and descriptive sense, and not for purposes of limitation. In some cases, it will be apparent to those skilled in the art from the time of filing this application that, unless otherwise specifically indicated, the features, characteristics, and / or elements described in conjunction with a particular embodiment may be used alone or in combination with the features, characteristics, and / or elements described in conjunction with other embodiments. Therefore, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the invention as described in 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 or S, R 1 and R 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group, R 3 To R 6 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, L 1 is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, Ar 1 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 is 1 or 2, m2 and m3 are each independently an integer from 1 to 3, and m4 is an integer of 1 to 4.

2. The compound for an organic optoelectronic device according to claim 1, wherein: Chemical Formula 1 is represented by one of Chemical Formulas 1-1 to 1-6: In Chemical Formulae 1-1 to 1-6, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 are the same as defined in Chemical Formula 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein: Chemical Formula 1 is represented by one of Chemical Formula 1-2A, Chemical Formula 1-2B, Chemical Formula 1-2C, Chemical Formula 1-5A, Chemical Formula 1-5B, or Chemical Formula 1-5C: In Formula 1-2A, Formula 1-2B, Formula 1-2C, Formula 1-5A, Formula 1-5B, and Formula 1-5C, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 are the same as defined in Chemical Formula 1.

4. The compound for an organic optoelectronic device according to claim 1, wherein: Chemical formula 1 is represented by one of Chemical formula 1-2A-2, Chemical formula 1-2A-3, Chemical formula 1-2B-2, Chemical formula 1-2C-2, Chemical formula 1-5A-2, or Chemical formula 1-5C-2: In Formula 1-2A-2, Formula 1-2A-3, Formula 1-2B-2, Formula 1-2C-2, Formula 1-5A-2, and Formula 1-5C-2, X 1 , R 1 To R 6 , L 1 ,Ar 1 and m1 to m4 are the same as defined in Chemical Formula 1.

5. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiorolyl, substituted or unsubstituted benzonaphthofuranyl or substituted or unsubstituted benzonaphthothiophenyl.

6. The compound for an organic optoelectronic device according to claim 1, wherein: Part-L 1 -Ar 1 Part of Group I: [Group I] In Group I, R 9 To R 12 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, R 13 and R 14 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, m5 is an integer from 1 to 5, m6 is an integer from 1 to 4, m7 is an integer from 1 to 3, m8 is 1 or 2, and * is the connection point.

7. A compound for an organic optoelectronic device, the compound being a compound of Group 1: [Group 1] 8. An organic optoelectronic device, comprising: an anode and a cathode opposite each other; and at least one organic layer located between the anode and the cathode, The at least one organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 7.

9. The organic optoelectronic device according to claim 8, wherein: The at least one organic layer includes a light emitting layer, and The light-emitting layer includes the compound.

10. The organic optoelectronic device according to claim 8, wherein: The at least one organic layer comprises: Luminescent layer, a hole transport layer located between the anode and the light-emitting layer, A hole transport auxiliary layer is located between the light emitting layer and the hole transport layer, and the hole transport auxiliary layer includes the compound. 11 . A display device comprising the organic optoelectronic device according to claim 8 .

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