Composition for organic optoelectronic device, organic optoelectronic device and display device

Abstract

Provided are a composition for an organic photoelectric device, an organic photoelectric device, and a display device, wherein the composition for an organic photoelectric device comprises a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2, and the organic photoelectric device comprises the composition. The details of Chemical Formula 1 and Chemical Formula 2 are as defined in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0066668 filed in the Korean Intellectual Property Office on June 02, 2020, the entire contents of which are incorporated herein by reference. Technical Field

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

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

[0005] Organic photoelectric devices can be roughly divided into two types according to the operating principle. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively; the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0006] Examples of organic optoelectronic devices include organic optoelectronic 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 largely affected by organic materials between electrodes. Summary of the invention

[0008] One embodiment provides a composition for an organic photoelectric device having high efficiency and long lifespan.

[0009] Another embodiment provides an organic photoelectric device including the composition for an organic photoelectric device.

[0010] Another embodiment provides a display device including an organic photoelectric device.

[0011] According to one embodiment, a composition for an organic photoelectric device includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

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

[0016] L 1 -L 3 Each is independently a single bond, or a substituted or unsubstituted C6-C30 arylene group,

[0017] R 1 -R 4 are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, and

[0018] R 5 -R 10 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic group;

[0019] [Chemical formula 2]

[0020]

[0021] Wherein, in Chemical Formula 2,

[0022] X 1 O, S, NL a -R a , CR b R c or SiR d R e ,

[0023] L a is a single bond, or a substituted or unsubstituted C6-C12 arylene group,

[0024] R a is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group,

[0025] R b , R c , R d and R e are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group,

[0026] R 11 and R 12are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclyl, and

[0027] A is any one of the rings selected from Group I,

[0028] [Group I]

[0029]

[0030] Among them, in group I,

[0031] * is linking carbon,

[0032] X 2 is O or S,

[0033] R 13 -R 24 are each independently hydrogen, deuterium, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0034] R a and R 11 -R 24 At least one of them is a group represented by chemical formula a,

[0035] [Chemical formula a]

[0036]

[0037] Among them, in chemical formula a,

[0038] Z 1 -Z 3 Each independently is N or CR f ,

[0039] Z 1 -Z 3 At least two of them are N,

[0040] R f is hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, or substituted or unsubstituted C6-C30 aryl,

[0041] L 4 -L 6 Each is independently a single bond, or a substituted or unsubstituted C6-C30 arylene group,

[0042] Ar 2 and Ar 3are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group, and

[0043] * indicates the connection point.

[0044] According to another embodiment, an organic photoelectric 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 light emitting layer, and the light emitting layer includes the composition for an organic photoelectric device.

[0045] According to another embodiment, a display device including an organic photoelectric device is provided.

[0046] Organic optoelectronic devices with high efficiency and long lifetime can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] Figure 1 and Figure 2 are cross-sectional views each showing an organic light emitting diode according to one embodiment.

[0048] <Description of symbols>

[0049] 100, 200: Organic light-emitting diodes

[0050] 105: Organic layer

[0051] 110: cathode

[0052] 120: Anode

[0053] 130: Luminous layer

[0054] 140: Hole auxiliary layer DETAILED DESCRIPTION

[0055] Hereinafter, embodiments of the present disclosure are described in detail. However, these embodiments are exemplary, the present disclosure is not limited thereto, and the present invention is defined by the scope of the claims.

[0056] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1-C30 amine, nitro, substituted or unsubstituted C1-C40 silyl (silyl), C1-C30 alkyl, C1-C10 alkylsilyl (alkylsilyl), C6-C30 arylsilyl (arylsilyl), C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C20 alkoxy, C1-C10 trifluoroalkyl, cyano, or a combination thereof.

[0057] In one example of the present disclosure, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1-C30 alkyl, C1-C10 alkylsilyl, C6-C30 arylsilyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, or cyano. In a specific example of the present disclosure, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1-C20 alkyl, C6-C30 aryl, or cyano. In a specific example of the present disclosure, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1-C5 alkyl, C6-C18 aryl, or cyano. In a specific example of the present disclosure, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0058] As used herein, when no definition is otherwise provided, "hetero" means containing 1 to 3 heteroatoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0059] 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 may be, for example, biphenyl, terphenyl, quarterphenyl, etc., and two or more hydrocarbon aromatic portions may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0060] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0061] 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 to replace carbon (C) in a cyclic compound (e.g., aryl, cycloalkyl, fused rings thereof or a combination thereof). When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0062] For example, "heteroaryl" may refer to an aryl group containing at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls may be directly connected by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0063] More specifically, the substituted or unsubstituted C6-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 naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted The invention may be substituted or unsubstituted triphenylene (triphenylene), substituted or unsubstituted peryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenyl, substituted or unsubstituted furanyl, or a combination thereof, but is not limited thereto.

[0064] More specifically, the substituted or unsubstituted C2-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, or a substituted or unsubstituted benzothiophenyl group. , 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 phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but are not limited thereto.

[0065] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0066] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and due to the conductive property 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.

[0067] Hereinafter, a composition for an organic photoelectric device according to one embodiment is described.

[0068] A composition for an organic photoelectric device according to one embodiment includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2 (eg, a mixture of the first compound and the second compound).

[0069] [Chemical formula 1]

[0070]

[0071] In Chemical Formula 1,

[0072] Ar 1 is a substituted or unsubstituted C6-C30 aryl group,

[0073] L 1 -L 3 Each is independently a single bond, or a substituted or unsubstituted C6-C30 arylene group,

[0074] R 1 -R 4 are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group, and

[0075] R 5 -R 10 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclyl;

[0076] [Chemical formula 2]

[0077]

[0078] Wherein, in Chemical Formula 2,

[0079] X 1 O, S, NL a -R a , CR b R c or SiR d R e ,

[0080] L a is a single bond, or a substituted or unsubstituted C6-C12 arylene group,

[0081] R a is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group,

[0082] R b , R c , R d and Re are each independently a substituted or unsubstituted C1-C30 alkyl group, or a substituted or unsubstituted C6-C30 aryl group,

[0083] R 11 and R 12 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclyl, and

[0084] A is any one of the rings selected from Group I,

[0085] [Group I]

[0086]

[0087] Among them, in group I,

[0088] * is a connecting carbon. As used herein, a connecting carbon is a carbon having an X-containing residue in Formula 2. 1 The carbon of A shared by the rings, for example, the shared carbon of the fused ring,

[0089] X 2 is O or S,

[0090] R 13 -R 24 are each independently hydrogen, deuterium, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0091] R a and R 11 -R 24 At least one of them is a group represented by chemical formula a,

[0092] [Chemical formula a]

[0093]

[0094] Among them, in chemical formula a,

[0095] Z 1 -Z 3 Each independently is N or CR f ,

[0096] Z 1 -Z 3 At least two of them are N,

[0097] R f is hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, or substituted or unsubstituted C6-C30 aryl,

[0098] L 4 -L 6 Each is independently a single bond, or a substituted or unsubstituted C6-C30 arylene group,

[0099] Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group, and

[0100] * indicates the connection point.

[0101] The first compound represented by Chemical Formula 1 has a structure including two dibenzosilole groups at the center of amine.

[0102] Since the two dibenzosilole groups can further improve the hole transport properties, low driving and high efficiency performance of the organic optoelectronic device including the same can be achieved.

[0103] Meanwhile, the second compound has a structure substituted with a nitrogen-containing 6-membered ring.

[0104] Since the second compound effectively expands the LUMO energy band by being substituted with a nitrogen-containing 6-membered ring, when used in the light-emitting layer together with the above-mentioned first compound, the mobility and stability of the charge can be increased, thereby increasing the balance between holes and electrons and improving the luminous efficiency and life characteristics of the device and reducing the driving voltage.

[0105] The first compound may be represented by one of Chemical Formulae 1A to 1D depending on a substitution position of one of the two dibenzosilyl groups.

[0106]

[0107]

[0108] In Chemical Formulae 1A to 1D, Ar 1 , L 1 -L 3 and R 1 -R 10 Same as above.

[0109] The first compound according to one embodiment may be represented by one of Chemical Formula 1A-1, Chemical Formula 1A-2, Chemical Formula 1A-3, Chemical Formula 1A-4, Chemical Formula 1B-1 to Chemical Formula 1B-3, Chemical Formula 1C-1, Chemical Formula 1C-2, and Chemical Formula 1D-1.

[0110]

[0111]

[0112]

[0113] In Formula 1A-1, Formula 1A-2, Formula 1A-3, Formula 1A-4, Formula 1B-1 to Formula 1B-3, Formula 1C-1, Formula 1C-2, and Formula 1D-1, Ar 1 , L 1 -L 3 and R 1 -R 10 Same as above.

[0114] The first compound according to one specific embodiment may be represented by one of Chemical Formula 1A-2a, Chemical Formula 1B-1a, Chemical Formula 1B-2a, and Chemical Formula 1B-3a.

[0115]

[0116]

[0117] In Formula 1A-2a and Formula 1B-1a to Formula 1B-3a, Ar 1 , L 1 -L 3 and R 1 -R 10 Same as above.

[0118] For example, Ar 1 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0119] For example, Ar 1 It may be substituted by a C6-C12 aryl group.

[0120] That is, Ar 1 It may be an unsubstituted phenyl group, a phenyl group substituted by a C6-C12 aryl group, an unsubstituted biphenyl group, a biphenyl group substituted by a C6-C12 aryl group, an unsubstituted naphthyl group, or a naphthyl group substituted by a C6-C12 aryl group.

[0121] As a specific example, L 3 may be a single bond or a substituted or unsubstituted phenylene group, and Ar 1 It may be one of the substituents selected from Group II.

[0122] [Group II]

[0123]

[0124] In Group II, * is the connection point.

[0125] For example, R 1 -R 4 Each independently may be a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C20 aryl group.

[0126] As a specific example, R 1 -R 4 Each independently may be a methyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0127] For example, R 5 -R 10 They may each independently be hydrogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C2-C18 heterocyclic group.

[0128] As a specific example, R 5 -R 10 They may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl.

[0129] For example, L 1 -L 3 Each independently may be a single bond, or a substituted or unsubstituted phenylene group.

[0130] For example, the first compound may be one of the compounds selected from Group 1.

[0131] [Group 1]

[0132]

[0133]

[0134]

[0135]

[0136] Meanwhile, A of the second compound may be selected from the rings of Group I, and may be represented, for example, by one of Chemical Formulae 2A to 2J.

[0137]

[0138]

[0139] In Chemical Formulae 2A to 2J, X 1 , X 2 , Z 1 -Z 3 , R 11 -R 24 , L 4 -L6 ,Ar 2 and Ar 3 Same as above.

[0140] The second compound according to one embodiment may be represented by one of Chemical Formula 2A, Chemical Formula 2C, and Chemical Formula 2F.

[0141] The second compound according to one specific embodiment may be represented by one of Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3.

[0142]

[0143]

[0144] In Formula 2A-3, Formula 2C-1, Formula 2F-1 and Formula 2F-3, X 1 , Z 1 -Z 3 , R 11 -R 17 , L 4 -L 6 ,Ar 2 and Ar 3 Same as above.

[0145] For example, Ar 2 and Ar 3 Each of them may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group.

[0146] As a specific example, Ar 2 and Ar 3 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0147] For example, L 4 -L 6 Each independently may be a single bond, or a substituted or unsubstituted phenylene group.

[0148] For example, R 11 -R 16 They may each independently be hydrogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C2-C18 heterocyclic group.

[0149] As a specific example, R 11 -R 16 They may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl.

[0150] For example, X 1 Can be O, S, CR b R c or SiR d R e , where R b , R c , R d and R e Each may independently be a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C20 aryl group.

[0151] As a specific example, R b , R c , R d and R e Each independently may be a methyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0152] For example, the second compound may be one selected from Group 2 compounds.

[0153] [Group 2]

[0154]

[0155]

[0156]

[0157]

[0158] A composition for an organic photoelectric device according to a more specific embodiment of the present disclosure may include a first compound represented by one of Chemical Formula 1A-2a and Chemical Formula 1B-1a to Chemical Formula 1B-3a and a second compound represented by one of Chemical Formula 2A-3a, Chemical Formula 2C-1a, and Chemical Formula 2F-1a.

[0159] Ar of Chemical Formula 1A-2a and Chemical Formula 1B-1a to Chemical Formula 1B-3a 1 It can be unsubstituted phenyl, phenyl substituted by C6-C12 aryl, unsubstituted biphenyl, biphenyl substituted by C6-C12 aryl, unsubstituted naphthyl or naphthyl substituted by C6-C12 aryl, L 1 -L 3 may be independently a single bond, or a substituted or unsubstituted phenylene group, R 1 -R 4may be independently substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C12 aryl, and R 5 -R 10 They may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl.

[0160] Chemical Formula 2A-3a, Chemical Formula 2C-1a, and Chemical Formula 2F-1a can be expressed as follows.

[0161]

[0162] [Chemical formula 2F-1a]

[0163]

[0164] In Chemical Formula 2A-3a, Chemical Formula 2C-1a and Chemical Formula 2F-1a,

[0165] X 1 O, S, CR b R c or SiR d R e ,

[0166] Z 1 -Z 3 Each is N,

[0167] R b , R c , R d and R e are each independently a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group,

[0168] R 13 is hydrogen, deuterium or phenyl,

[0169] L 4 -L 6 are each independently a single bond, or a substituted or unsubstituted phenylene group, and

[0170] Ar 2 and Ar 3 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0171] The composition for an organic photoelectric device according to a more specific embodiment of the present disclosure may include a first compound selected from Group 1-1 and a second compound selected from Group 2-1.

[0172] [Group 1-1]

[0173]

[0174]

[0175] [Group 2-1]

[0176]

[0177] The first compound and the second compound may be included (e.g., mixed) in a weight ratio of, for example, about 1:99 to about 99:1. When they are included in the above range, the hole transport ability of the first compound and the electron transport ability of the second compound may be used to adjust a suitable weight ratio to achieve bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, for example, they may be included in a weight ratio of about 90:10 to about 10:90, about 80:20 to about 10:90, about 70:30 to about 10:90, or about 60:40 to about 10:90. For example, they may be included in a weight ratio of about 60:40 to about 20:80, for example, about 60:40 to about 30:70.

[0178] According to a more specific embodiment, they may be included in a weight ratio of about 60:40 to about 40:60.

[0179] In one embodiment of the present disclosure, the first compound and the second compound may each be included as a host of the light-emitting layer, for example, a phosphorescent host.

[0180] Hereinafter, an organic photoelectric device including the above-mentioned composition for an organic photoelectric device is described.

[0181] The organic photoelectric device may be any device that converts electrical energy into light energy, or vice versa, without particular limitation, and may be, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photoconductor.

[0182] Herein, an organic light emitting diode as one example of an organic photoelectric device is described with reference to the accompanying drawings.

[0183] Figure 1 and Figure 2 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0184] Reference Figure 1 , an 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 .

[0185] 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 an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); a combination of metals and oxides 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.

[0186] 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; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0187] The organic layer 105 may include the above-mentioned composition for an organic photoelectric device.

[0188] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-mentioned composition for an organic photoelectric device.

[0189] The light emitting layer 130 may include, for example, the above-mentioned composition for an organic photoelectric device as a phosphorescent host.

[0190] The light emitting layer may further include one or more compounds in addition to the above-mentioned host.

[0191] The light emitting layer may further include a dopant. 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.

[0192] The composition for an organic photoelectric device further including a dopant may be, for example, a composition that emits red light.

[0193] The dopant may be a material mixed in a small amount with the compound for an organic photoelectric device or the composition for an organic photoelectric device to cause light emission, and may generally be a material such as a metal complex that emits light by multiple excitations to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0194] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0195] [Chemical formula Z]

[0196] L 7 MX 3

[0197] In the chemical formula Z, M is a metal, L is 7 and X 3 The same or different and is a ligand that forms a complex with M.

[0198] 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 7 and X 3 This may be, for example, a bidentate ligand.

[0199] The organic layer may further include an auxiliary layer in addition to the light emitting layer.

[0200] The auxiliary layer may be, for example, Figure 2 A hole assist layer 140 is shown.

[0201] Reference Figure 2 In addition to the light emitting layer 130 , the organic light emitting diode 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 .

[0202] The hole auxiliary layer 140 may include, for example, at least one of the compounds of group A.

[0203] 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.

[0204] [Group A]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] In the hole transport auxiliary layer, in addition to the compounds described above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and the like can be used.

[0211] In one 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 .

[0212] The organic light emitting diodes 100 and 200 may be manufactured by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0213] Organic light emitting diodes can be applied to organic light emitting display devices.

[0214] Hereinafter, the embodiments are described in more detail with reference to examples. However, these examples are exemplary, and the scope of claims is not limited thereto.

[0215] Hereinafter, unless otherwise specified, raw materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry Co., Ltd., or P&H Technologies, Inc., or were synthesized by known methods.

[0216] (Preparation of compounds for organic optoelectronic devices)

[0217] The compounds provided as more specific examples of the compounds disclosed herein were synthesized by the following steps.

[0218] Synthesis of the first compound

[0219] Synthesis Example 1: Synthesis of Compound 2

[0220] [Reaction Scheme 1]

[0221]

[0222] Step 1: Synthesis of Int-3

[0223] Int-1 (100 g, 315.11 mmol) was dissolved in 1.0 L tetrahydrofuran (THF), and Int-2 (63.28 g, 315.11 mmol) and tetrakis (triphenylphosphine) palladium (10.92 g, 9.45 mmol) were added thereto, and then stirred. Subsequently, potassium carbonate (108.88 g, 787.77 mmol) saturated in 500 ml of water was added thereto, and then heated to reflux at 80° C. for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain 86.24 g (79%) of Int-3.

[0224] Step 2: Synthesis of Int-4

[0225] Int-3 (86.24 g, 248.92 mmol) was dissolved in 600 mL of tetrahydrofuran (THF), and its internal temperature was lowered to -78° C. n-BuLi (288.75 ml, 721.88 mmol) was slowly added thereto in a dropwise manner while maintaining the internal temperature of -78° C., and then stirred at that temperature for 1 hour.

[0226] Subsequently, dichlorodimethylsilane (104.31 ml, 871.24 mmol) was slowly added thereto in a dropwise manner while maintaining a temperature of -78°C, and then stirred at room temperature for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain 43.12 g (71%) of Int-4.

[0227] Step 3: Synthesis of compound 2

[0228] 1.21g (5.5mmol) Int-5, 2.69g (11.01mmol) Int-4, 1.32g (13.76mmol) sodium tert-butoxide and 0.22g (0.55mmol) tri-tert-butylphosphine were dissolved in 55ml dimethylbenzene, and 0.25g (0.28mmol) Pd2 (dba) 3 was added thereto, and then stirred and refluxed for 12 hours under a nitrogen atmosphere. When the reaction was complete, the organic layer was extracted with dimethylbenzene and distilled water, treated with anhydrous magnesium sulfate to remove moisture, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 2: 1) to obtain 2.8g (yield: 80%) compound 2.

[0229] Calculated value for C44H37NSi2: C, 83.10; H, 5.86; N, 2.20; Si, 8.83; Found: C, 83.10; H, 5.86; N, 2.20; Si, 8.83

[0230] Synthesis Example 2: Synthesis of Compound 4

[0231] [Reaction Scheme 2]

[0232]

[0233] Step 1: Synthesis of Int-8

[0234] Int-6 (150 g, 530.2 mmol) was dissolved in 1.8 L tetrahydrofuran (THF), and Int-7 (82.91 g, 530.02 mmol) and tetrakis (triphenylphosphine) palladium (18.38 g, 15.91 mmol) were added thereto, and then stirred. Subsequently, potassium carbonate (183.20 g, 1325.51 mmol) saturated in 900 ml of water was added thereto, and then heated and refluxed at 80 ° C for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain 89.37 g (63%) of Int-8.

[0235] Step 2: Synthesis of Int-9

[0236] Int-8 (89 g, 332.65 mmol) was dissolved in 1 L of tetrahydrofuran (THF), and its internal temperature was lowered to -78° C. n-BuLi (160 ml, 399.18 mmol) was slowly added thereto in a dropwise manner while maintaining the internal temperature of -78° C., and then stirred at this temperature for 1 hour.

[0237] Subsequently, dichlorodimethylsilane (47.66 ml, 415.81 mmol) was slowly added dropwise while maintaining a temperature of -78°C and then stirred at room temperature for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to give 53.37 g (65%) of Int-9.

[0238] Step 3: Synthesis of Int-10

[0239] Int-9 (53.0 g, 214.74 mmol) was dissolved in 850 mL trifluorotoluene, and di-tert-butyl peroxide (120 ml, 644.22 mmol) was slowly added thereto in a dropwise manner. The resulting mixture was heated and refluxed at an internal temperature of 120° C. for 48 hours. When the reaction was complete, the reaction solution was cooled to room temperature, and 400 ml of water was added thereto, followed by stirring for 1 hour. The mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain 56.52 g (75%) of Int-10.

[0240] Step 4: Synthesis of Int-11

[0241] 5.72g (23.4mmol) of Int-10, 6.67g (30.40mmol) of Int-5, 5.62g (58.46mmol) of sodium tert-butoxide and 0.95g (2.34mmol) of tri-tert-butylphosphine were dissolved in 230ml of xylene, and 1.07g (1.17mmol) of Pd2(dba)3 was added thereto, and then refluxed and stirred for 12 hours under a nitrogen atmosphere. When the reaction was complete, the organic layer was extracted with xylene and distilled water, treated with anhydrous magnesium sulfate to remove moisture, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 2:1) to obtain 6.40g (64%) of Int-11.

[0242] Step 5: Synthesis of compound 4

[0243] 6.30g (14.73mmol) Int-11, 3.61g (14.73mmol) Int-4, 3.54g (36.83mmol) sodium tert-butoxide and 0.60g (1.47mmol) tri-tert-butylphosphine were dissolved in 120ml dimethylbenzene, and 0.68g (0.74mmol) Pd2(dba)3 was added thereto, and then refluxed and stirred for 12 hours under a nitrogen atmosphere. When the reaction was complete, the organic layer was extracted with dimethylbenzene and distilled water, treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 2: 1) to obtain 6.6g (yield: 70%) compound 4.

[0244] Calculated for C44H37NSi2: C, 83.10; H, 5.86; N, 2.20; Si, 8.83; Found: C, 83.11; H, 5.86; N, 2.20; Si, 8.82

[0245] Synthesis example 3-18

[0246] Each compound was synthesized according to the same method as Synthesis Example 1 or 2, except that IntA shown in Table 1 was used instead of Int-4 in Synthesis Example 1 or 2, and Int B shown in Table 1 was used instead of Int-6 in Synthesis Example 1 or Int-11 in Synthesis Example 2.

[0247] (Table 1)

[0248]

[0249]

[0250]

[0251] Comparative Synthesis Examples 1-4

[0252] Each comparative compound was synthesized according to the same method as Synthesis Example 1 or 2, except that Int A shown in Table 2 was used instead of Int-4 in Synthesis Example 1 or 2, and Int B shown in Table 2 was used instead of Int-11.

[0253] (Table 2)

[0254]

[0255]

[0256]

[0257] Synthesis of the second compound

[0258] Synthesis Example 19: Synthesis of Compound A-3

[0259] [Reaction Scheme 3]

[0260]

[0261] Step 1: Synthesis of Int-29

[0262] 22.6 g (100 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine was added to 200 mL of tetrahydrofuran and 100 mL of distilled water in a round-bottom flask, and 0.9 equivalents of dibenzofuran-3-boric acid (CAS No.: 395087-89-5) were added, 0.03 equivalents of tetrakis (triphenylphosphine) palladium and 2 equivalents of potassium carbonate were added thereto, and then heated and refluxed under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and the organic layer obtained after removing the water layer therefrom was dried under reduced pressure. The obtained solid was washed with water and hexane, and recrystallized with 200 mL of toluene to obtain 21.4 g (yield: 60%) of Int-29.

[0263] Step 2: Synthesis of Int-30

[0264] 50.0 g (261.16 mmol) of 1-bromo-4-chlorobenzene, 44.9 g (261.16 mmol) of 2-naphthaleneboric acid, 9.1 g (7.83 mmol) of tetrakis(triphenylphosphine)palladium and 71.2 g (522.33 mmol) of potassium carbonate were dissolved in 1000 mL of tetrahydrofuran and 500 mL of distilled water in a round-bottom flask, and then heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and the organic layer obtained after removing the water layer therefrom was dried under reduced pressure. The obtained solid was washed with water and hexane, and then recrystallized from 200 mL of toluene to obtain 55.0 g (yield: 88%) of Int-30.

[0265] Step 3: Synthesis of Int-31

[0266] 100.0g (418.92mmol) of the synthesized Int-30 is added to the 1000mL DMF in a round-bottomed flask, and 17.1g (20.95mmol) of dichlorodiphenylphosphinoferrocene palladium, 127.7g (502.70mmol) of bispinacolato diboron and 123.3g (1256.76mmol) of potassium acetate are added thereto, and then heated to reflux for 12 hours under a nitrogen atmosphere. The reaction solution is cooled and added to 2L water in a dropwise manner to obtain a solid. The resulting solid is dissolved in boiling toluene and filtered in silica gel, and the filtrate thus obtained is concentrated. The concentrated solid is stirred with a small amount of hexane, then filtered, and 28.5g (yield: 70%) of Int-31 is obtained.

[0267] Step 4: Synthesis of Compound A-3

[0268] 10.0 g (27.95 mmol) of Int-31, 11.1 g (33.54 mmol) of Int-29, 1.0 g (0.84 mmol) of tetrakis (triphenylphosphine) palladium and 7.7 g (55.90 mmol) of potassium carbonate were dissolved in 150 mL of tetrahydrofuran and 75 mL of distilled water in a round-bottom flask, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, and the organic layer obtained after removing the water layer therefrom was dried under reduced pressure. The obtained solid was washed with water and methanol, and then recrystallized from 200 mL of toluene to obtain 13.4 g (yield: 91%) of compound A-3.

[0269] Calculated value for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Found: C, 84.55; H, 4.41; N, 8.00; O, 3.03.

[0270] Synthesis Example 20: Synthesis of Compound A-71

[0271] [Reaction Scheme 4]

[0272]

[0273] Step 1: Synthesis of Int-32

[0274] Int-32 was synthesized according to the same method as Int-29 of Synthesis Example 19, except that 2,4-dichloro-6-phenyl-1,3,5-triazine and 1-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-dibenzofuran were each used in 1.0 equivalent.

[0275] Step 2: Synthesis of Compound A-71

[0276] Compound A-71 was synthesized according to the same method as step 4 of Synthesis Example 19, except that Int-32 and Int-31 were each used in 1.0 equivalent.

[0277] Calculated value for C43H27N3O: C, 85.83; H, 4.52; N, 6.98; O, 2.66; Found: C, 85.83; H, 4.52; N, 6.98; O, 2.66.

[0278] Synthesis Example 21: Synthesis of Compound A-61

[0279] [Reaction Scheme 5]

[0280]

[0281] Step 1: Synthesis of Int-33

[0282] 21.95 g (135.53 mmol) of 2-benzofuran boronic acid, 26.77 g (121.98 mmol) of 2-bromo-5-chlorobenzaldehyde, 2.74 g (12.20 mmol) of Pd(OAc) and 25.86 g (243.96 mmol) of NaCO were suspended in 200 ml of acetone / 220 ml of distilled water in a round-bottom flask and then stirred at room temperature for 12 hours. When the reaction was complete, the product was concentrated and extracted with dichloromethane, and the organic layer obtained therefrom was subjected to silica gel column chromatography to obtain 21.4 g (yield: 68%) of Int-33.

[0283] Step 2: Synthesis of Int-34

[0284] 20.4g (79.47mmol) Int-33 and 29.97g (87.42mmol) (methoxymethyl) triphenylphosphonium chloride are suspended in 400ml THF, and 10.70g (95.37mmol) potassium tert-butoxide is added thereto, and then at room temperature stirred 12 hours. When the reaction is complete, 400ml distilled water is added thereto, then extraction, the organic layer obtained by it is concentrated and extracted again with methylene dichloride, then magnesium sulfate is added thereto, then stirred 30 minutes and filtered, and the filtrate obtained by it is concentrated. Subsequently, 100ml methylene dichloride is added in the concentrated filtrate, and 10ml methylsulfonic acid is added thereto, then stirred 1 hour.

[0285] When the reaction was completed, the solid produced therein was filtered and washed with distilled water and methanol to obtain 21.4 g (yield: 65%) of Int-34.

[0286] Step 3: Synthesis of Int-35

[0287] 12.55 g (49.66 mmol) of Int-34, 2.43 g (2.98 mmol) of Pd(dppf)Cl2, 15.13 g (59.60 mmol) of bis(pinacolato)diboron, 14.62 g (148.99 mmol) of KOAc and 3.34 g (11.92 mmol) of P(Cy)3 were suspended in 200 ml of DMF, and then refluxed and stirred for 12 hours. When the reaction was completed, 200 ml of distilled water was added thereto, and the solid produced therein was filtered and extracted with dichloromethane, and the organic layer therein was subjected to column chromatography with hexane:EA=4:1 (v / v) to obtain 13 g (yield: 76%) of Int-35.

[0288] Step 4: Synthesis of Compound A-61

[0289] Compound A-61 was synthesized according to the same method as step 4 of Synthesis Example 19, except that Int-35 and Int-36 were each used in 1.0 equivalent.

[0290] Calculated value for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Found: C, 84.55; H, 4.41; N, 7.99; O, 3.04.

[0291] Synthesis Example 22: Synthesis of Compound A-17

[0292] [Reaction Scheme 6]

[0293]

[0294] Compound A-17 was synthesized according to the same method as step 4 of Synthesis Example 19, except that Int-37 and Int-38 were each used in 1.0 equivalent.

[0295] Calculated value for C41H25N3O: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Found: C, 85.53; H, 4.38; N, 7.30; O, 2.77.

[0296] Synthesis Example 23: Synthesis of Compound A-37

[0297] [Reaction Scheme 7]

[0298]

[0299] Compound A-37 was synthesized according to the same method as step 4 of Synthesis Example 19, except that Int-37 and Int-36 were each used in 1.0 equivalent.

[0300] Calculated value for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Found: C, 84.57; H, 4.40; N, 7.99; O, 3.03.

[0301] Synthesis of Synthesis Examples 24-26

[0302] Each compound was synthesized according to the same method as step 4 of Synthesis Example 19, except that IntC of Table 3 was used instead of Int-31 in Synthesis Example 19, and Int D of Table 3 was used instead of Int-29.

[0303] (Table 3)

[0304]

[0305] (Preparation of Organic Light Emitting Diodes)

[0306] Example 1

[0307] The glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The resulting ITO transparent electrode was used as an anode, and Compound A (available from Novaled) doped with 1% NDP-9 was vacuum deposited on the ITO substrate to form A thick hole transport layer is formed, and compound B is deposited on the hole transport layer to form On the hole transport auxiliary layer, the compound 2 obtained in Synthesis Example 1 and the compound A-17 obtained in Synthesis Example 19 were simultaneously vacuum deposited as the main body, and 2 wt % of [Ir(piq)2acac] was doped as a dopant to form Herein, compound 2 and compound A-17 are used in a weight ratio of 5:5. Subsequently, compound C is deposited on the light-emitting layer to form A thick electron transport auxiliary layer is formed, and compound D and LiQ are simultaneously vacuum deposited in a weight ratio of 1:1 to form On the electron transport layer, Liq and Al are vacuum deposited sequentially to Thick and harmonious thick, and an organic light emitting diode having the following structure was prepared.

[0308] ITO / Compound A (1% NDP-9 doping, ) / Compound B / EML[98wt% Host(Compound 2:Compound A-17=50:50(wt%):2wt%[Ir(piq)2acac] / Compound C / Compound D:Liq / LiQ / Al

[0309] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0310] Compound B: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran-10-amine

[0311] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0312] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0313] Examples 2-27 and Comparative Examples 1-4

[0314] Diodes of Examples 2-27 and Comparative Examples 1-4 were prepared in the same manner as in Example 1, except that the host was changed as described in Table 4.

[0315] Evaluation: Impact of lifespan synergy

[0316] (1) Measurement of current density changes depending on voltage changes

[0317] The resulting organic light emitting diode was measured for a current value flowing in a unit diode using a current-voltage meter (Keithley 2400) while increasing a voltage from 0 V to 10 V, and the measured current value was divided by an area to provide a result.

[0318] (2) Measurement of brightness changes depending on voltage changes

[0319] A brightness meter (Minolta C S -1000A) to measure the brightness while increasing the voltage of the OLED from 0V to 10V.

[0320] (3) Measurement of luminous efficiency

[0321] The luminance and current density measured by (1) and (2) were used to calculate the current density (10 mA / cm 2 )'s luminous efficiency (cd / A).

[0322] (4) Lifespan measurement

[0323] In the case of brightness (cd / m 2 ) maintained at 5,000cd / m 2 At the same time, the time for the luminous efficiency (cd / A) to decrease to 90% was measured to obtain the results.

[0324] (5) Measurement of driving voltage

[0325] The current-voltage meter (Keithley 2400) was used to measure the current of each diode at 15 mA / cm 2 of driving voltage to obtain the result.

[0326] (6) T90 lifespan ratio (%)

[0327] The relative value of each T90(h) was calculated using T90(h) of Comparative Example 4 in Table 4 as a reference value, and the results are shown in Table 4.

[0328] (7) Driving voltage ratio (%)

[0329] The relative value of each driving voltage was calculated using the driving voltage of Comparative Example 4 in Table 4 as a reference value, and the results are shown in Table 4.

[0330] (8) Luminous efficiency ratio (%)

[0331] The relative value of each luminous efficiency (cd / A) was calculated using the luminous efficiency (cd / A) of Comparative Example 4 in Table 4 as a reference value, and the results are shown in Table 4.

[0332] (Table 4)

[0333]

[0334] Referring to Table 4, the compounds according to the present disclosure exhibit greatly improved driving voltage, efficiency and lifespan compared to the comparative compounds.

[0335] While the disclosure 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 on the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A composition for an organic optoelectronic device, comprising A first compound represented by Chemical Formula 1B and a second compound represented by Chemical Formula 2A, Chemical Formula 2C or Chemical Formula 2F: in, In Chemical Formula 1B, Ar 1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted naphthyl, L 1 -L 3 are each independently a single bond, or a substituted or unsubstituted phenylene group, R 1 -R 4 are each independently a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C20 aryl group, and R 5 -R 10 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C12 aryl; Wherein, in Chemical Formula 2A, Chemical Formula 2C and Chemical Formula 2F, X 1 is O or S, Z 1 -Z 3 Each independently is N or CR f , R f , R 11 To R 17 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C12 aryl, and L 4 -L 6 are each independently a single bond, or a substituted or unsubstituted phenylene group, Ar 2 and Ar 3 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and Here, "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, C1-C20 alkyl, C6-C30 aryl or cyano.

2. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by one of Chemical Formula 1B-1 to Chemical Formula 1B-3: Among them, in Chemical Formula 1B-1 to Chemical Formula 1B-3, Ar 1 , L 1 -L 3 and R 1 -R 10 As defined in claim 1.

3. The composition for an organic optoelectronic device according to claim 2, wherein The first compound is represented by one of Chemical Formula 1B-1a to Chemical Formula 1B-3a: Among them, in Chemical Formula 1B-1a to Chemical Formula 1B-3a, Ar 1 , L 1 -L 3 and R 1 -R 10 As defined in claim 2.

4. The composition for an organic optoelectronic device according to claim 1, wherein Ar 1 The "substituted" is C6-C12 aryl.

5. The composition for an organic optoelectronic device according to claim 1, wherein Ar 1 is one of the substituents selected from Group II: [Group II] in, In Group II, * is the connection point.

6. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is one of the compounds selected from Group 1: [Group 1] 7. The composition for an organic optoelectronic device according to claim 1, wherein The second compound is represented by one of Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1 and Chemical Formula 2F-3: Among them, in Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3, X 1 , Z 1 -Z 3 , R 11 -R 17 , L 4 -L 6 ,Ar 2 and Ar 3 Same as defined in Chemical Formula 2A, Chemical Formula 2C and Chemical Formula 2F.

8. The composition for an organic optoelectronic device according to claim 1, wherein The second compound is one of the compounds selected from Group 2: [Group 2] 9. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by one of Chemical Formula 1B-1a to Chemical Formula 1B-3a, and The second compound is represented by one of Chemical Formula 2A-3a, Chemical Formula 2C-1a and Chemical Formula 2F-1a: in, In Chemical Formula 1B-1a to Chemical Formula 1B-3a, Ar 1 is unsubstituted phenyl, phenyl substituted by a C6-C12 aryl group, unsubstituted biphenyl group, biphenyl group substituted by a C6-C12 aryl group, unsubstituted naphthyl group, or naphthyl group substituted by a C6-C12 aryl group, L 1 -L 3 are each independently a single bond, or a substituted or unsubstituted phenylene group, R 1 -R 4 are each independently a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group, and R 5 -R 10 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl; Among them, in Chemical Formula 2A-3a, Chemical Formula 2C-1a and Chemical Formula 2F-1a, X 1 is O or S, Z 1 -Z 3 Each is N, R 13 is hydrogen, deuterium, or substituted or unsubstituted phenyl, L 4 -L 6 are each independently a single bond, or a substituted or unsubstituted phenylene group, and Ar 2 and Ar 3 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

10. The composition for an organic optoelectronic device according to claim 9, wherein The first compound is selected from Group 1-1, and The second compound is selected from Group 2-1: [Group 1-1] [Group 2-1] 11. 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, Wherein, the organic layer includes a light-emitting layer, and The light-emitting layer comprises the composition for an organic photoelectric device according to any one of claims 1 to 10.

12. The organic optoelectronic device according to claim 11, wherein: The composition for an organic photoelectric device is included as a host of the light-emitting layer.

13. The organic optoelectronic device according to claim 12, wherein: The composition for an organic photoelectric device includes the first compound and the second compound in a weight ratio of 60:40 to 30:

70.

14. A display device comprising the organic photoelectric device according to claim 11.

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