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

Abstract

The present invention relates to: a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1; and an organic optoelectronic device and a display device, each of which contains the compound. Details of the chemical formula 1 are defined in the specification.

Description

Technical Field

[0001] Disclosed are a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0002] An organic optoelectronic device (organic optoelectronic diode) is a device that can convert electrical energy into light energy and vice versa.

[0003] Organic optoelectronic devices can be broadly divided into two categories based on their operating principles: photovoltaic devices that generate electrical energy by separating excitons formed from light energy into electrons and holes and transferring these electrons and holes to different electrodes; and light-emitting devices that generate light energy from electrical energy by applying voltage or current to electrodes.

[0004] 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.

[0005] 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 the organic material between electrodes. Summary of the Invention

[0006] Technical issues

[0007] One embodiment provides a compound for an organic optoelectronic device capable of realizing a low-driving, high-efficiency, and long-life organic optoelectronic device.

[0008] Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device.

[0009] Another embodiment provides a display device including an organic optoelectronic device.

[0010] Technical Solution

[0011] According to one embodiment, 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 It is O or S,

[0016] R 1 and R 2are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof,

[0017] Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzosilyl group, a substituted or unsubstituted spirocyclopentane-1,9'-fluorenyl group, a substituted or unsubstituted spirocyclohexane-1,9'-fluorenyl group or a substituted or unsubstituted spirofluorene-9,9'-xanthenyl group,

[0018] Ar 3 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0019] L 1 and L 2 are each independently 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,

[0020] m1 and m2 are each independently an integer from 1 to 3, and

[0021] "Substituted" means that at least one hydrogen is replaced by deuterium, C1 to C5 alkyl, C6 to C12 aryl, or cyano.

[0022] According to another embodiment, 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.

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

[0024] Beneficial effects

[0025] An organic optoelectronic device with high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

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

[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 zone

[0034] 150: Electron transport region DETAILED DESCRIPTION

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

[0036] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, halogen, hydroxy, 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 embodiment of the present invention, "substituted" means 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 a specific embodiment of the present invention, "substituted" means 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 a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0038] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0039] In the present specification, "deuterium substitution (—D)" may include "tritium substitution (—T)".

[0040] In the present specification, "t-Bu" or "tBu" represents a tert-butyl group.

[0041] As used herein, when no definition is otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0042] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals forming conjugation, such as phenyl, naphthyl, etc.; two or more hydrocarbon aromatic moieties may be linked by a σ bond, and may be, for example, biphenyl, terphenyl, quaterphenyl, etc.; and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0043] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

[0044] As used herein, "heterocyclyl" is 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 fused ring thereof or a combination thereof. When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl may include one or more heteroatoms.

[0045] As an example, "heteroaryl" may refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups may be directly linked by a sigma bond, or when the heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0046] 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 p-terphenyl group, a substituted or unsubstituted m-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 triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0047] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted The present invention may include, but is not limited to, quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, 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 or substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuranofluorenyl, substituted or unsubstituted benzothiophenefluorenyl, or a combination thereof, but is not limited thereto.

[0048] 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 properties 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.

[0049] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0050] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0051] The compound for an organic optoelectronic device according to one embodiment is represented by Chemical Formula 1.

[0052] [Chemical Formula 1]

[0053]

[0054] In Chemical Formula 1,

[0055] X 1 It is O or S,

[0056] R 1and R 2 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof,

[0057] Ar 1 and Ar 2 are each 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 triphenylene, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted 9,9′-spirobifluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted dibenzosilyl, a substituted or unsubstituted spirocyclopentane-1,9′-fluorenyl, a substituted or unsubstituted spirocyclohexane-1,9′-fluorenyl or a substituted or unsubstituted spirofluorene-9,9′-xanthenyl,

[0058] Ar 3 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0059] L 1 and L 2 are each independently 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,

[0060] m1 and m2 are each independently an integer from 1 to 3, and

[0061] "Substituted" means that at least one hydrogen is replaced by deuterium, C1 to C5 alkyl, C6 to C12 aryl, or cyano.

[0062] The compound represented by Chemical Formula 1 has a structure in which an amine group is substituted at the 1-position of dibenzofuran (or dibenzothiophene) and an aryl group is substituted at the 9-position. Due to the stabilization of the interaction between the 1-position substituent (amine group) and the 9-position substituent (aryl group), the driving voltage of an organic light-emitting diode to which it is applied can be reduced and the lifespan can be improved.

[0063] 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.

[0064] For example, Ar 1 and Ar 2Each of the groups 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 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzosilyl group.

[0065] As a specific example, L 1 -Ar 1 and L 2 -Ar 2 The substituents listed in Group I may be each independently selected.

[0066] [Group I]

[0067]

[0068] In Group I,

[0069] R 3 to R 7 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, or substituted or unsubstituted C6 to C12 aryl,

[0070] R 8 and R 9 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

[0071] m3 is an integer from 1 to 5,

[0072] m4 is an integer from 1 to 4,

[0073] m5 is an integer from 1 to 3,

[0074] m6 is an integer from 1 to 8,

[0075] m7 is one of integers from 1 to 10, and

[0076] * is the connection point.

[0077] When m3 is 2 or greater, each R 3 They may be the same as or different from each other.

[0078] When m4 is 2 or greater, each R 4 They may be the same as or different from each other.

[0079] When m5 is 2 or greater, each R 5 They may be the same as or different from each other.

[0080] When m6 is 2 or greater, each R 6 They may be the same as or different from each other.

[0081] When m7 is 2 or greater, each R 7 They may be the same as or different from each other.

[0082] For example, Ar 3 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.

[0083] 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.

[0084] [Group 1]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] In addition to the above-mentioned compounds for an organic optoelectronic device, one or more other compounds may be included.

[0093] For example, a dopant may be further contained.

[0094] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0095] A dopant is a material mixed in a small amount with a compound used in an organic optoelectronic device to induce light emission, and is generally a material such as a metal complex that emits light by being excited multiple times 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.

[0096] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organometallic 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 be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0097] [Chemical formula Z]

[0098] L 3 MX 2

[0099] In the chemical formula Z, M is a metal, and L 3 and X 2 The same or different ligands that form a complex with M.

[0100] 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 3 and X 2 This can be, for example, a bidentate ligand.

[0101] By L 3 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.

[0102] [Group A]

[0103]

[0104] In Group A,

[0105] 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

[0106] R 303 to R 324and each independently represents 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,

[0107] n1 is an integer from 1 to 5,

[0108] n2 is an integer from 1 to 4,

[0109] n3 is an integer from 1 to 3,

[0110] n4 is an integer of 1 or 2, and

[0111] n5 is an integer from 1 to 6.

[0112] When n1 is 2 or greater, each substituent may be the same as or different from each other.

[0113] When n2 is 2 or greater, each substituent may be the same as or different from each other.

[0114] When n3 is 2 or greater, each substituent may be the same as or different from each other.

[0115] When n4 is 2 or greater, each substituent may be the same as or different from each other.

[0116] When n5 is 2 or greater, each substituent may be the same as or different from each other.

[0117] The dopant according to one embodiment may be an iridium complex, for example, an iridium complex represented by Chemical Formula 4-1 or Chemical Formula 4-2.

[0118] [Chemical Formula 4-1]

[0119]

[0120] In Chemical Formula 4-1,

[0121] 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 R134 ,

[0122] R 132 to R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0123] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula V-1,

[0124] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of carbon or a heteroatom, and

[0125] 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,

[0126] [Chemical Formula V-1]

[0127]

[0128] In Chemical Formula V-1,

[0129] R 135 to R 139 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 ,and

[0130] * indicates a moiety attached to a carbon atom.

[0131] [Chemical Formula 4-2]

[0132]

[0133] In Chemical Formula 4-2,

[0134] R 101 to R 117 are 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 ,

[0135] R 133 to R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0136] L 100is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of carbon or a heteroatom, and

[0137] n1 and n2 are each independently any integer from 0 to 3, and n1+n2 is any integer from 1 to 3.

[0138] In another embodiment, the dopant may be a platinum complex, such as a platinum complex represented by Chemical Formula Z-1.

[0139] [Chemical Formula Z-1]

[0140]

[0141] In formula Z-1, rings A, B, C, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0142] R A 、R B 、R C and R D each independently mono-, di-, tri- or tetra-substituted or unsubstituted;

[0143] L B , L C and L D are each independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof,

[0144] When nA is 1, L E It can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof; and when nA is 0, L E does not exist;

[0145] R A 、R B 、R C 、R D R and R' are each independently hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, or a combination 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 XE 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.

[0146] The platinum complex can be represented by, for example, Chemical Formula 5-1 or Chemical Formula 5-2.

[0147] [Chemical Formula 5-1]

[0148]

[0149] [Chemical Formula 5-2]

[0150]

[0151] In Chemical Formula 5-1 and Chemical Formula 5-2,

[0152] X 100 Selected from O, S and NR 132 ,

[0153] R 118 to R 132 are 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 ,

[0154] R 133 to R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0155] R 118 to R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl, and

[0156] R 133 to R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0157] An organic optoelectronic device using the compound for an organic optoelectronic device is described.

[0158] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa, such as an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0159] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0160] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0161] refer to Figure 1 , the organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0162] 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 an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or 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.

[0163] 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, or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0164] The organic layer 105 may include the above-described compound for an organic optoelectronic device.

[0165] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described compound for an organic optoelectronic device.

[0166] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light emitting composition.

[0167] The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host.

[0168] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0169] The charge transport region may be, for example, a hole transport region 140 .

[0170] The hole transport region 140 may further improve hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0171] 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 the hole transport auxiliary layer may include the compound for an organic optoelectronic device.

[0172] Meanwhile, the light emitting layer includes a host and a dopant, and the host may be, for example, a phosphorescent host.

[0173] The phosphorescent host should facilitate the injection and transport of holes and electrons within the light-emitting layer, and ultimately the holes and electrons should meet to smoothly form excitons, and the energy of the formed excitons should be smoothly transferred to the dopant. Examples of the phosphorescent host may include organic compounds including carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzopyran, indolodibenzothiophene, fluorene, indenocarbazole, triphenylene, pyrimidine, triazine, or a combination thereof.

[0174] The phosphorescent host may be used without limitation as long as it is a known material, and may be, for example, a single host or a mixed host.

[0175] In addition, the above compound for an organic optoelectronic device may be included in the light emitting layer, and at least one of the compounds listed in Group C may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0176] [Group C]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] (Dn refers to the number of hydrogens replaced by deuterium and represents a structure substituted with one or more deuteriums)

[0184] In the hole transport region, in addition to the above-mentioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having similar structures can also be used.

[0185] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0186] The electron transport region 150 may further improve electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0187] 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 D may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0188] [Group D]

[0189]

[0190]

[0191]

[0192]

[0193] One embodiment may be an organic light emitting diode including a light emitting layer as an organic layer.

[0194] Another embodiment may be an organic light emitting diode including a light emitting layer and a hole transport region as organic layers.

[0195] Another embodiment may be an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0196] In addition to the light emitting layer 130, the organic light emitting diode of one embodiment further includes a hole transport region 140 and an electron transport region 150 as the organic layer 105. Figure 1 shown.

[0197] 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 organic layers in addition to the light emitting layer.

[0198] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0199] Organic light emitting diodes can be applied to organic light emitting display devices.

[0200] Invention Mode

[0201] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the claims is not limited thereto.

[0202] 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.

[0203] (Preparation of Compounds for Organic Optoelectronic Devices)

[0204] Synthesis Example 1: Synthesis of Compound 1-1

[0205]

[0206] IM-1 (15.0 g, 53.8 mmol) was dissolved in toluene (180 mL), and sub-1 (21.6 g, 53.8 mmol), NaOtBu (6.98 g, 72.6 mmol), Pd2(dba)3 (2.96 g, 3.23 mmol) and P(t-Bu)3 (4.61 mL, 9.7 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 14.5 g (yield: 42%) of compound 1-1.

[0207] Synthesis Example 2: Synthesis of Compound 1-4

[0208]

[0209] IM-1 (15.0 g, 53.8 mmol) was dissolved in toluene (180 mL), and sub-2 (19.4 g, 53.8 mmol), NaOtBu (6.98 g, 72.6 mmol), Pd2(dba)3 (2.96 g, 3.23 mmol) and P(t-Bu)3 (4.61 mL, 9.7 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 15.6 g (yield: 48%) of compound 1-4.

[0210] Synthesis Example 3: Synthesis of Compound 1-10

[0211]

[0212] IM-1 (15.0 g, 53.8 mmol) was dissolved in toluene (180 mL), and sub-3 (17.3 g, 53.8 mmol), NaOtBu (6.98 g, 72.6 mmol), Pd2(dba)3 (2.96 g, 3.23 mmol) and P(t-Bu)3 (4.61 mL, 9.7 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 13.4 g (yield: 44%) of compound 1-10.

[0213] Synthesis Example 4: Synthesis of Compound 1-26

[0214]

[0215] IM-1 (15.0 g, 53.8 mmol) was dissolved in toluene (180 mL), and sub-4 (22.5 g, 53.8 mmol), NaOtBu (6.98 g, 72.6 mmol), Pd2(dba)3 (2.96 g, 3.23 mmol) and P(t-Bu)3 (4.61 mL, 9.7 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 15.1 g (yield: 42%) of compound 1-26.

[0216] Synthesis Example 5: Synthesis of Compound 1-27

[0217]

[0218] IM-2 (15.0 g, 40.8 mmol) was dissolved in toluene (135 mL), and sub-2 (14.7 g, 40.8 mmol), NaOtBu (5.29 g, 55.1 mmol), Pd2(dba)3 (2.24 g, 2.45 mmol) and P(t-Bu)3 (3.50 mL, 7.3 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 12.4 g (yield: 44%) of compound 1-27.

[0219] Synthesis Example 6: Synthesis of Compound 1-28

[0220]

[0221] IM-2 (15.0 g, 40.8 mmol) was dissolved in toluene (135 mL), and sub-1 (16.4 g, 40.8 mmol), NaOtBu (5.29 g, 55.1 mmol), Pd2(dba)3 (2.24 g, 2.45 mmol) and P(t-Bu)3 (3.50 mL, 7.3 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 11.8 g (yield: 40%) of compound 1-28.

[0222] Comparative Synthesis Example 1: Synthesis of Compound F-1

[0223]

[0224] IM-1 (15.0 g, 53.8 mmol) was dissolved in toluene (180 mL), and sub-5 (24.9 g, 53.8 mmol), NaOtBu (6.98 g, 72.6 mmol), Pd2(dba)3 (2.96 g, 3.23 mmol) and P(t-Bu)3 (4.61 mL, 9.7 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 16.1 g (yield: 41%) of compound F-1.

[0225] Comparative Synthesis Example 2: Synthesis of Compound F-2

[0226]

[0227] IM-1 (15.0 g, 53.8 mmol) was dissolved in toluene (180 mL), and sub-5 (24.9 g, 53.8 mmol), NaOtBu (6.98 g, 72.6 mmol), Pd2(dba)3 (2.96 g, 3.23 mmol) and P(t-Bu)3 (4.61 mL, 9.7 mmol) were added thereto, and then refluxed for 3 hours. When the reaction was completed, the organic layer extracted with CH2Cl2 and water was dried over MgSO4, concentrated, separated by silica gel column and recrystallized to obtain 17.2 g (yield: 49%) of compound F-2.

[0228] (Manufacturing of organic light-emitting diodes)

[0229] Example 1

[0230] A glass substrate coated with an ITO / Ag / ITO thin film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as acetone, isopropyl alcohol, etc. and dried, then moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The prepared ITO / Ag / ITO (reflective electrode) was used as an anode, and Compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO / Ag / ITO substrate to form a A thick hole injection layer is formed, and compound A is deposited on the hole injection layer. The hole transport layer was formed by depositing the compound 1-1 obtained in Synthesis Example 1 on the hole transport layer. On the hole transport auxiliary layer, 90 wt% of the host H1 (40%) and the host H2 (60%) were used as hosts and 10 wt% of GD was doped as a dopant to form a hole transport auxiliary layer by vacuum deposition. Then, compound C is deposited on the light emitting layer. Thick to form an electron transport auxiliary layer, and compound D and Liq are vacuum deposited at a weight ratio of 1:1 to form The organic light-emitting diode is manufactured by sequentially vacuum-depositing Yb and AgMg on the electron transport layer to form a cathode.

[0231] An organic light emitting diode was manufactured to have the following structure: ITO / Ag / ITO / Compound A (3% NDP-9 doping, ) / Compound A( ) / Hole transport auxiliary layer( ) / Emitting layer [Host (Host H1:Host H2=40wt%:60wt%):GD=90wt%:10wt%]( ) / Compound C( ) / Compound D:Liq( ) / Yb / AgMg.

[0232] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0233] Compound C: 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0234] Compound D: 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)

[0235] Host H1: 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(triphenyl-2-yl)phenyl)-1,3,5-triazine

[0236] Host H2: 9,9"-diphenyl-9H,9"H-3,3':9',3"-tricarbazole

[0237] GD:

[0238]

[0239] Examples 2 to 6 and Comparative Examples 1 and 2

[0240] The diodes of Examples 2 to 6 and Comparative Examples 1 and 2 were manufactured 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.

[0241] evaluate

[0242] (1) Measuring the change in current density according to voltage change

[0243] 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.

[0244] (2) Measuring the brightness change according to the voltage change

[0245] 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).

[0246] (3) Measure the driving voltage

[0247] The current was measured at 15 mA / cm using a current-voltage meter (Keithley 2400). 2 The driving voltage of each diode is shown below.

[0248] The relative values ​​based on the driving voltage of Comparative Example 1 are shown in Table 1.

[0249] (4) Measurement life

[0250] In the case of brightness (cd / m 2 ) maintained at 24000cd / m 2 At the same time, the time required for each current efficiency (cd / A) to decrease to 97% was measured as the lifespan.

[0251] Relative values ​​based on the lifetime measurement values ​​of Comparative Example 1 are shown in Table 1.

[0252] [Table 1]

[0253]

[0254] Referring to Table 1, the organic light emitting diode to which the compound according to the embodiment of the present invention is applied has significantly improved driving voltage and lifespan characteristics compared to the organic light emitting diode according to the comparative example.

[0255] 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 It is O or S, R 1 and R 2 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, Ar 1 and Ar 2 are each 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 triphenylene, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted 9,9′-spirobifluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted dibenzosilyl, a substituted or unsubstituted spirocyclopentane-1,9′-fluorenyl, a substituted or unsubstituted spirocyclohexane-1,9′-fluorenyl or a substituted or unsubstituted spirofluorene-9,9′-xanthenyl, Ar 3 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, L 1 and L 2 are each independently 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, m1 and m2 are each independently an integer from 1 to 3, and "Substituted" means that at least one hydrogen is replaced by deuterium, C1 to C5 alkyl, C6 to C12 aryl, or cyano.

2. The compound for an organic optoelectronic device according to claim 1, wherein L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

3. The compound for an organic optoelectronic device according to claim 1, wherein 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 3 to R 7 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, or substituted or unsubstituted C6 to C12 aryl, R 8 and R 9 are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, m3 is an integer from 1 to 5, m4 is an integer from 1 to 4, m5 is an integer from 1 to 3, m6 is an integer from 1 to 8, m7 is one of integers from 1 to 10, and * is the connection point.

4. The compound for an organic optoelectronic device according to claim 1, wherein Ar 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothienyl group.

5. The compound for an organic optoelectronic device according to claim 1, wherein The compound is selected from the compounds listed in Group 1: [Group 1] 6. An organic optoelectronic device comprising: 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 5.

7. The organic optoelectronic device according to claim 6, wherein: The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic optoelectronic device.

8. The organic optoelectronic device according to claim 6, wherein The organic layer includes luminescent layer, a hole transport layer between the anode and the light-emitting layer, and a hole transport auxiliary layer between the light emitting layer and the hole transport layer, Wherein, the hole transport auxiliary layer comprises the compound for an organic optoelectronic device. 9 . A display device comprising the organic optoelectronic device according to claim 6 .

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