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

Abstract

The present invention discloses a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. The compound for an organic optoelectronic device is represented by Chemical Formula 1. The definitions of Chemical Formula 1 are the same as those in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0115527, filed on September 19, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present invention discloses a compound for an organic photoelectric device, a composition for an organic photoelectric device, an organic photoelectric device and a display device. Background Art

[0004] An organic photovoltaic device (organic photodiode) is a device that converts electrical energy into light energy (or vice versa).

[0005] Organic photoelectric devices can be classified into the following categories based on their driving principles: one is a photoelectric device in which excitons generated from light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, respectively, to generate electric energy; and the other is a light-emitting device in which electric energy is generated from light energy by supplying voltage or current to electrodes.

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

[0007] Among them, organic light emitting diodes (OLEDs) have recently attracted attention due to the increasing demand for flat panel displays. Organic light emitting diodes convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by organic materials arranged between electrodes. Summary of the Invention

[0008] One embodiment provides a compound for an organic photoelectric device, which can realize an organic photoelectric device having high efficiency and a long lifespan.

[0009] Another embodiment provides a composition for an organic optoelectronic device, comprising the compound.

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

[0011] Another embodiment provides a display device including an organic optoelectronic device.

[0012] According to an embodiment, a compound for an organic photoelectric device represented by Chemical Formula 1 is provided.

[0013] [Chemical formula]

[0014]

[0015] In Chemical Formula 1,

[0016] R 1 and R 2 are independently hydrogen, unsubstituted phenyl or unsubstituted biphenyl,

[0017] R 1 and R 2 At least one of them is an unsubstituted phenyl group or an unsubstituted biphenyl group,

[0018] R 3 and R 4 are independently unsubstituted phenyl or unsubstituted biphenyl, and

[0019] R 5 to R 9 and R and R are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0020] According to another embodiment, a composition for an organic photoelectric device includes a first compound for an organic photoelectric device and a second compound for an organic photoelectric device.

[0021] The first compound for an organic photoelectric device includes the above-mentioned compound for an organic photoelectric device, and the second compound for an organic photoelectric device includes the compound for an organic photoelectric device represented by Chemical Formula 2.

[0022] [Chemical Formula 2]

[0023]

[0024] In Chemical Formula 2,

[0025] Y 1 and Y 2 are independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0026] Ar 1 and Ar 2 are independently substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0027] R 10 to R 15 and independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, cyano, or a combination thereof.

[0028] According to another embodiment, an organic photoelectric device includes an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes a compound for an organic photoelectric device or a composition for an organic photoelectric device.

[0029] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0030] Organic photoelectric devices with high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 and Figure 2 Each is a cross-sectional view of an organic light emitting diode according to an embodiment. DETAILED DESCRIPTION

[0032] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary and the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0033] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or 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.

[0034] In one embodiment of the present invention, "substituted" refers to the replacement of at least one hydrogen atom of a substituent or compound with 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. Furthermore, in specific embodiments of the present invention, "substituted" refers to the replacement of at least one hydrogen atom of a substituent or compound with deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. Furthermore, in specific embodiments of the present invention, "substituted" refers to the replacement of at least one hydrogen atom of a substituent or compound with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. Furthermore, in specific embodiments of the present invention, "substituted" refers to the replacement of at least one hydrogen atom of a substituent or compound with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0035] 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.

[0036] As used herein, “aryl” refers to a group including at least one hydrocarbon aromatic moiety, and may include a group in which all elements of the hydrocarbon aromatic moiety have p-orbitals forming a conjugation, such as phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic moieties may be linked by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc., and a group in which two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl, etc.

[0037] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

[0038] As used herein, "heterocyclic group" is a general concept of heteroaryl groups and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a ring (such as an aryl group, a cycloalkyl group, a condensed ring thereof or a combination thereof). When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0039] For example, "heteroaryl" refers to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are 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 from one to three heteroatoms.

[0040] 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 naphthphenyl 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 triphenylenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof, but is not limited thereto.

[0041] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted phenylthio 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 benzothiophenyl group, a substituted or unsubstituted The compounds include, but are not limited to, substituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, 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 phenoxazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but are not limited thereto.

[0042] In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, based on the highest occupied molecular orbital (HOMO) energy level, and the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductive properties.

[0043] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductive properties, according to the lowest unoccupied molecular orbital (LUMO) energy level.

[0044] Hereinafter, a compound for an organic photoelectric device according to an embodiment is described.

[0045] The compound for an organic photoelectric device according to an embodiment is represented by Chemical Formula 1.

[0046] [Chemical Formula 1]

[0047]

[0048] In Chemical Formula 1,

[0049] R 1 and R 2 are independently hydrogen, unsubstituted phenyl or unsubstituted biphenyl,

[0050] R 1 and R 2 At least one of them is an unsubstituted phenyl group or an unsubstituted biphenyl group,

[0051] R 3 and R 4 are independently unsubstituted phenyl or unsubstituted biphenyl, and

[0052] R 5 to R 9 and R and R are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0053] For the compound represented by Chemical Formula 1, a kinked terphenyl group is introduced into the indolecarbazole to increase the stability of the material. At the same time, the kinked terphenyl group is additionally substituted with a C6 to C12 aryl group to improve electron mobility, thereby having the effect of improving the deposited film and ultimately achieving low-drive, high-efficiency, and long-life device characteristics.

[0054] The compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by one of Chemical Formulas 1A to 1C according to the aryl group further substituted with the terphenyl group.

[0055] [Chemical Formula 1A] [Chemical Formula 1B]

[0056]

[0057] [Chemical Formula 1C]

[0058]

[0059] In Chemical Formulas 1A to 1C, R 3 to R 9 Same as above.

[0060] More specifically, Chemical Formula 1A may be represented by one of Chemical Formula 1A-1 to Chemical Formula 1A-3.

[0061] [Chemical Formula 1A-1] [Chemical Formula 1A-2]

[0062]

[0063] [Chemical Formula 1A-3]

[0064]

[0065] In Chemical Formulas 1A-1 to 1A-3, R 3 to R 9 Same as above.

[0066] More specifically, Chemical Formula 1B may be represented by one of Chemical Formula 1B-1 to Chemical Formula 1B-6.

[0067] [Chemical Formula 1B-1] [Chemical Formula 1B-2] [Chemical Formula 1B-3]

[0068]

[0069] [Chemical Formula 1B-4] [Chemical Formula 1B-5] [Chemical Formula 1B-6]

[0070]

[0071] In Chemical Formulas 1B-1 to 1B-6, R 3 to R 9 Same as above.

[0072] More specifically, Chemical Formula 1C may be represented by one of Chemical Formula 1C-1 to Chemical Formula 1C-9.

[0073] [Chemical Formula 1C-1] [Chemical Formula 1C-2]

[0074]

[0075] [Chemical Formula 1C-3] [Chemical Formula 1C-4]

[0076]

[0077] [Chemical Formula 1C-5] [Chemical Formula 1C-6]

[0078]

[0079] [Chemical Formula 1C-7] [Chemical Formula 1C-8] [Chemical Formula 1C-9]

[0080]

[0081] In Chemical Formulas 1C-1 to 1C-9, R 3 to R 9 Same as above.

[0082] The compound for an organic photoelectric device according to an embodiment of the present invention may be represented by Chemical Formula 1A-2.

[0083] For example, the compound for an organic photoelectric device represented by Chemical Formula 1 may be selected from one of the compounds of Group 1, but is not limited thereto.

[0084] [Group 1]

[0085] [A-1][A-2][A-3][A-4][A-5]

[0086]

[0087] [A-6][A-7][A-8][A-9][A-10]

[0088]

[0089] [A-11][A-12][A-13][A-14][A-15]

[0090]

[0091] [A-16][A-17][A-18][A-19][A-20]

[0092]

[0093] [A-21][A-22][A-23][A-24][A-25]

[0094]

[0095] [A-26][A-27][A-28][A-29][A-30]

[0096]

[0097] [A-31][A-32][A-33][A-34][A-35]

[0098]

[0099] [A-36][A-37][A-38][A-39][A-40]

[0100]

[0101] [A-41][A-42][A-43][A-44][A-45]

[0102]

[0103] [A-46][A-47][A-48][A-49]

[0104]

[0105] [A-50][A-51][A-52][A-53][A-54]

[0106]

[0107] [A-55][A-56][A-57][A-58][A-59]

[0108]

[0109] [A-60][A-61][A-62][A-63][A-64]

[0110]

[0111] [A-65][A-66][A-67][A-68][A-69]

[0112]

[0113] A composition for an organic optoelectronic device according to another embodiment includes the above-described compound (hereinafter referred to as the "first compound for an organic optoelectronic device") and a second compound for an organic optoelectronic device. In one embodiment, the composition may include a mixture of the first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device. The second compound for an organic optoelectronic device may be represented by Chemical Formula 2.

[0114] [Chemical Formula 2]

[0115]

[0116] In Chemical Formula 2,

[0117] Y 1 and Y 2 are independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0118] Ar 1 and Ar 2 are independently substituted or unsubstituted C 6 to C 20 an alkaryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group;

[0119] R 10 to R 15 and independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, cyano, or a combination thereof.

[0120] The second compound for an organic optoelectronic device (which is a material having fast and stable hole transfer characteristics) can be used in the light-emitting layer together with the first compound for an organic optoelectronic device (which has fast and stable electron transfer characteristics) to provide charge balance, thereby having a glass transition temperature relative to the molecular weight to provide low drive and long life characteristics.

[0121] In an exemplary embodiment of the present invention, Ar of Chemical Formula 2 1and Ar 2 Y may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted pyridyl group, 1 and Y 2 may independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and R 10 to R 15 and may independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

[0122] The “substituted” of Chemical Formula 2 may mean that at least one hydrogen is replaced by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0123] For example, the chemical formula 2 * -Y 1 -Ar 1 and *-Y 2 -Ar 2 It may be one of the substituents in Group I.

[0124] [Group I]

[0125]

[0126] In group I, * is the connection point.

[0127] For example, the compound for an organic photoelectric device represented by Chemical Formula 2 may be one selected from the compounds of Group 2, but is not limited thereto.

[0128] [Group 2]

[0129] [B-1][B-2][B-3][B-4][B-5]

[0130]

[0131] [B-6][B-7][B-8][B-9][B-10]

[0132]

[0133] [B-11][B-12][B-13][B-14][B-15]

[0134]

[0135] [B-16][B-17][B-18][B-19][B-20]

[0136]

[0137] [B-21][B-22][B-23][B-24][B-25]

[0138]

[0139] [B-26][B-27][B-28][B-29][B-30]

[0140]

[0141] [B-31][B-32][B-33][B-34][B-35]

[0142]

[0143] [B-36][B-37][B-38][B-39][B-40]

[0144]

[0145] [B-41][B-42][B-43][B-44][B-45]

[0146]

[0147] [B-46][B-47][B-48][B-49][B-50]

[0148]

[0149] [B-51][B-52][B-53][B-54][B-55]

[0150]

[0151] [B-56][B-57][B-58][B-59][B-60]

[0152]

[0153] [B-61][B-62][B-63][B-64][B-65]

[0154]

[0155] [B-66][B-67][B-68][B-69][B-70]

[0156]

[0157] [B-71][B-72][B-73]

[0158]

[0159] The first compound for an organic photoelectric device and the second compound for an organic photoelectric device may be used in the form of a composition (eg, a mixture).

[0160] For example, the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device may be a host.

[0161] The first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device can be included in a weight ratio of about 1:99 to about 99:1. Within this range, the electron transport ability of the first compound for an organic optoelectronic device and the hole transport ability of the second compound for an organic optoelectronic device can be used to adjust the desired weight ratio to achieve bipolar characteristics, thereby improving efficiency and lifespan. Within this range, for example, they can be included in a weight ratio of about 90:10 to about 10:90, about 80:20 to about 20:80, for example, about 80:20 to about 30:70, or about 70:30 to about 30:70. For example, they can be included in a weight ratio of about 60:40 to about 30:70, and specifically, a weight ratio of about 40:60.

[0162] The compound for an organic optoelectronic device or the composition for an organic optoelectronic device may further include a dopant. For example, the dopant may be a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0163] A dopant is a material mixed in a small amount to induce light emission, and is generally a material such as a metal complex that emits light by multiple excitation to a triplet state or a multiplet state. For example, the dopant may be an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0164] 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. For example, the phosphorescent dopant may be a compound represented by the chemical formula Z, but is not limited thereto.

[0165] [Chemical formula Z]

[0166] L 3 MX A

[0167] In the chemical formula Z, M is a metal, and L 3 and X A are the same or different and are ligands that form a coordination compound with M.

[0168] For example, M can be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and for example, L 4 and X may be a bidentate ligand.

[0169] The (first) compound for an organic photoelectric device or the composition for an organic photoelectric device may be formed by a dry film formation method such as chemical vapor deposition.

[0170] Hereinafter, an organic photoelectric device to which the above-mentioned (first) compound for an organic photoelectric device or the composition for an organic photoelectric device is applied is described.

[0171] Without particular limitation, the organic photoelectric device may be any device that converts electrical energy into light energy and vice versa, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0172] Herein, an organic light emitting diode as one embodiment of an organic photoelectric device is described with reference to the accompanying drawings.

[0173] Figure 1 and Figure 2 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0174] refer to Figure 1 , the organic light emitting diode 100 according to the 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 .

[0175] 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. For example, the anode 120 may be: a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0176] 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. For example, the cathode 110 may be 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, but not limited to, LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0177] The organic layer 105 includes a light-emitting layer 130 , which includes the above-described (first) compound or composition for an organic optoelectronic device.

[0178] For example, the light emitting layer 130 may include the above-mentioned compound or composition.

[0179] refer to Figure 2 In addition to the light-emitting layer 130, the organic light-emitting device 200 further includes a hole auxiliary layer 140. The hole auxiliary layer 140 further increases hole injection and / or hole mobility and blocks electrons between the anode 120 and the light-emitting layer 130. For example, the hole auxiliary layer 140 may be a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.

[0180] For example, the hole assist layer 140 may include at least one of the group A compounds.

[0181] Specifically, the hole auxiliary layer 140 may include a hole transport layer between the anode 120 and the light emitting layer 130 and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, and at least one of the compounds of group A may be included in the hole transport auxiliary layer.

[0182] [Group A]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] In the hole transport auxiliary layer, in addition to the compounds described above, known compounds disclosed in US Pat. No. 5,061,569 A, JP 1993-009471 A, WO 1995-009147 A1, JP 1995-126615 A, JP 1998-095972 A, etc., and compounds similar thereto can be used.

[0189] In an embodiment, Figure 1 or Figure 2 In the embodiment, the organic light emitting diode may further include an electron transport layer, an electron injection layer or a hole injection layer as the organic layer 105 .

[0190] The organic light emitting diodes 100 and 200 may be manufactured 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 the cathode or anode thereon.

[0191] Organic light emitting diodes can be applied to organic light emitting display devices.

[0192] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0193] Hereinafter, raw materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry, or P&Htech unless specifically commented or synthesized by a known method.

[0194] (Preparation of Compounds for Organic Photoelectric Devices)

[0195] The compound as a specific example of the present invention was synthesized by the following steps.

[0196] (Preparation of the First Compound for Organic Photoelectric Device)

[0197] Synthesis Example 1: Synthesis of Intermediate 1

[0198] [Reaction Scheme 1]

[0199]

[0200] 3-Bromo-5-chloro-1,1'-biphenyl (30 g, 112.8 mmol), 3-phenylphenylboronic acid (22.3 g, 112.8 mmol), KCO (34.2 g, 248 mmol) and Pd(PPh) (6.5 g, 5.6 mmol) were placed in a round-bottom flask, and then dissolved in 300 ml of THF and 150 ml of distilled water, and then stirred at 80° C. under reflux for 20 hours. When the reaction was complete, after removing the aqueous layer, the residue was treated by column chromatography (hexane:DCM (20%)) to obtain 35 g (81%) of Intermediate 1.

[0201] Synthesis Example 2: Synthesis of Intermediate 2

[0202] [Reaction Scheme 2]

[0203]

[0204] Intermediate 1 (25 g, 73.5 mmol) was placed in a round-bottom flask with 11,12-dihydroindole [2,3-a] carbazole (20.7 g, 80.8 mmol), Pd (dba) (2 g, 2.2 mmol), P (t-Bu) (1.4 g, 7.4 mmol) and sodium tert-butoxide (7.7 g, 80.8 mmol) and then stirred at 140° C. in 220 ml of xylene under reflux for 20 hours. When the reaction was complete, the product was cooled to room temperature and then slowly poured into distilled water and stirred for 1 hour. The solid was filtered, dissolved in ethyl acetate and dried over MgSO. After removing the organic solvent under reduced pressure, the residue was vacuum dried to obtain 32 g (78%) of intermediate 2.

[0205] Synthesis Example 3: Synthesis of Compound A-1

[0206] [Reaction Scheme 3]

[0207]

[0208] Intermediate 2 (18.6 g, 33.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (11.5 g, 43.1 mmol) and sodium hydride (1.2 g, 49.8 mmol) were placed in a round-bottom flask and then stirred in 130 ml of DMF at room temperature for 12 hours. The resulting solid was filtered and then stirred in the aqueous layer for 30 minutes. The solid was filtered and dried to obtain 22 g (83%) of compound A-1.

[0209] (Preparation of the Second Compound for Organic Photoelectric Device)

[0210] Synthesis Example 4: Synthesis of Compound B-71

[0211] Compound B-71 was synthesized by a known method.

[0212] (Comparative Synthesis Example)

[0213] The following comparative compounds were synthesized by known methods.

[0214] (Comparative Compound 1) (Comparative Compound 2)

[0215]

[0216] (Comparative Compound 3) (Comparative Compound 4) (Comparative Compound 5)

[0217]

[0218] (Comparative Compound 6)

[0219]

[0220] (Manufacturing of organic light-emitting diodes)

[0221] Example 1

[0222] Will be coated with A glass substrate of ITO (indium tin oxide) with a thickness of 1000 nm was washed with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent (such as isopropyl alcohol, acetone, methanol, etc.) and dried, and then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus obtained was used as an anode, and compound A was vacuum-deposited on the ITO substrate to form Thick hole injection layer, and compound B is deposited on the injection layer to Thick, and then, compound C is deposited as On the hole transport layer, a hole transport layer was formed by using the compound A-1 obtained in Synthesis Example 3 as a host and doping 7 wt % of PhGD as a dopant by vacuum deposition. Subsequently, on the light-emitting layer, a film was formed by simultaneously vacuum-depositing compound D and Liq in a weight ratio of 1:1. Thick electron transport layer, and on the electron transport layer, Liq and Al are vacuum deposited in sequence to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0223] The organic light emitting diode has five organic thin layers and specifically has the following structure.

[0224] ITO / Compound A / Compound B Compound C / EML[Compound A-1: ​​PhGD (7 wt%)] / Compound D: Liq / Liq / Al

[0225] Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamine

[0226] Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN)

[0227] Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0228] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0229]

[0230] Example 2 and Comparative Examples 1 to 12

[0231] Except that the compositions were changed as shown in Table 1 and Table 2, an organic light emitting diode was manufactured in the same manner as in Example 1.

[0232] Evaluate

[0233] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 and 2 and Comparative Examples 1 to 12 were evaluated.

[0234] The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

[0235] (1) Measurement of current density changes according to voltage changes

[0236] The obtained organic light emitting diode was measured with respect to a current value flowing in a unit device while increasing a voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), and the measured current value was divided by an area to provide a result.

[0237] (2) Measurement of brightness changes according to voltage changes

[0238] 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).

[0239] (3) Measurement of luminous efficiency

[0240] By using the luminance and current density from items (1) and (2), the luminance at the same current density (10 mA / cm 2 ) under luminous efficiency (cd / A).

[0241] (4) Lifespan measurement

[0242] The brightness (cd / m 2 ) maintained at 24,000cd / m 2At the same time, the results were obtained by measuring the time it takes for the luminous efficiency (cd / A) to drop to 95%.

[0243] (5) Measurement of driving voltage

[0244] An ampere-voltmeter (Keithley 2400) was used at 15 mA / cm 2 Measure the driving voltage of each diode.

[0245] (6) Calculation of T95 lifespan ratio (%)

[0246] When a single host or a mixed host including the same second host is used, T95(h) ratios of Examples (first compound as the first host) and Comparative Examples (comparative compounds respectively applied as the first host) are presented.

[0247] T95 life ratio (%) = {[T95 (h) of Examples and Comparative Examples (the first compound alone or as a main component of a mixture)] / [T95 (h) of Reference Data (the comparative compound alone or as a main component of a mixture)]} × 100

[0248] (7) Calculation of driving voltage ratio (%)

[0249] When a single host or a mixed host including the same second host is used, the driving voltage ratios of Examples (the first compound as the first host) and Comparative Examples (comparative compounds respectively applied as the first host) are shown.

[0250] Driving voltage ratio (%) = {[driving voltage (V) of the embodiment or comparative example (the first compound alone or as a main component of the mixture)] / [reference data (the comparative compound alone or as a main component of the mixture)]} × 100

[0251] (8) Calculation of power efficiency ratio (%)

[0252] When a single host or a mixed host including the same second host is used, power efficiency ratios of Examples (the first compound as the first host) and Comparative Examples (comparative compounds respectively applied as the first host) are shown.

[0253] Power efficiency ratio (%) = {[power efficiency (Cd / A) of the embodiment and comparative example (the first compound alone or as a mixed host)] / [reference data (the comparative compound alone or as a mixed host)]} × 100

[0254] [Table 1]

[0255]

[0256] Table 2

[0257]

[0258]

[0259] Referring to Tables 1 and 2, compared with materials that do not include a kinked terphenyl structure or do not include additional substituents in addition to the kinked terphenyl structure, the materials of the present invention, including additional phenyl or biphenyl groups in addition to the kinked terphenyl structure, exhibit equal or higher driving voltage and power efficiency, and at the same time, exhibit greatly increased lifespan.

[0260] While the invention has been described in connection with what are presently considered to be practical embodiments, it should be understood that the invention is not limited to the disclosed embodiments, but on the contrary is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0261] <symbol description>

[0262] 100, 200: Organic light-emitting diodes

[0263] 105: Organic layer

[0264] 110: cathode

[0265] 120: Anode

[0266] 130: Luminous layer

[0267] 140: Hole assisting layer.

Claims

1. A compound for an organic optoelectronic device, represented by Chemical Formula 1A-2: [Chemical Formula 1A-2] in, In Chemical Formula 1A-2, R 3 and R 4 are independently unsubstituted phenyl or unsubstituted biphenyl, R 5 to R 9 is independently hydrogen or deuterium.

2. The compound according to claim 1, wherein The compound is one selected from the following group 1: [Group 1] [A-6] 3. A composition for an organic optoelectronic device, comprising a first compound for an organic photoelectric device and a second compound for an organic photoelectric device, in, The first compound for an organic photoelectric device comprises the compound for an organic photoelectric device according to claim 1, and The second compound for an organic photoelectric device includes a compound for an organic photoelectric device represented by Chemical Formula 2: [Chemical Formula 2] Wherein, in Chemical Formula 2, Y 1 and Y 2 are independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, Ar 1 and Ar 2 are independently substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and R 10 to R 15 and independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, cyano, or a combination thereof.

4. The composition according to claim 3, wherein *-Y 1 -Ar 1 and *-Y 2 -Ar 2 is one of the substituents of Group I: [Group I] Where, in group I, * is the connection point.

5. An organic optoelectronic device comprising The anode and cathode face each other, at least one organic layer, the at least one organic layer being arranged between the anode and the cathode, in, The organic layer comprises the compound for an organic optoelectronic device according to claim 1 or claim 2 or the composition for an organic optoelectronic device according to claim 3 or claim 4. The organic photoelectric device according to claim 5 , wherein: The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic photoelectric device. A display device comprising the organic optoelectronic device according to claim 5 .

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