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

Abstract

The present invention relates to a composition for an organic optoelectronic device, and an organic optoelectronic device and a display device comprising the same, the composition comprising a first compound represented by Chemical Formula 1, a second compound represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and a third compound, and the third compound is represented by Chemical Formula 5. Details of the chemical formula 1 to the chemical formula 5 are as described in the specification.

Description

Technical Field

[0001] The invention discloses a composition for an organic optoelectronic device, an organic optoelectronic device and a display device. Background Art

[0002] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy and light energy into one another.

[0003] Organic optoelectronic devices can be mainly divided into two types according to the working 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, while the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0004] Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting diodes, organic solar cells, and organic photoconductors.

[0005] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by organic materials between electrodes. Summary of the invention

[0006] [Technical issues]

[0007] One embodiment provides a composition for an organic optoelectronic device capable of realizing an organic optoelectronic device with high efficiency and long lifetime.

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

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

[0010]

Technical solution

[0011] According to one embodiment, the composition for an organic optoelectronic device includes a first compound, a second compound and a third compound, wherein the first compound is represented by Chemical Formula 1, the second compound is represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and the third compound is represented by Chemical Formula 5.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] Z 1 To Z3 N or CL a -R a ,

[0016] Z 1 To Z 3 At least two of them are N,

[0017] L a and L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0018] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0019] R a and R 1 To R 3 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof,

[0020] R a Each exists independently or is connected to Ar 1 or Ar 2 To form a substituted or unsubstituted heteroaromatic polycyclic ring,

[0021] R 1 To R 3 Each exists independently or adjacent groups therein are linked to form a substituted or unsubstituted heteroaromatic polycyclic ring,

[0022] m1 is an integer from 1 to 3, and

[0023] m2 and m3 are each independently an integer from 1 to 4;

[0024] [Chemical formula 2]

[0025]

[0026] Wherein, in Chemical Formula 2,

[0027] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0028] L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0029] R 4 To R 8 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0030] m5 and m6 are each independently an integer from 1 to 3,

[0031] m4, m7 and m8 are each independently one of integers from 1 to 4, and

[0032] n is an integer from 0 to 2;

[0033]

[0034] Wherein, in chemical formulas 3 and 4,

[0035] Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0036] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL b -R b ,

[0037] Among a1* to a4* in Chemical Formula 3, adjacent two are connected to * in Chemical Formula 4,

[0038] L b , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0039] R b , R 9 and R 10 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0040] m9 and m10 are each independently an integer from 1 to 4;

[0041] [Chemical formula 5]

[0042]

[0043] Among them, in chemical formula 5,

[0044] R 11 To R 15 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof, L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0045] m11, m12, m14 and m15 are each independently one of integers from 1 to 4, and m13 is one of integers from 1 to 3.

[0046] According to another embodiment, an organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer includes the above-mentioned compound for an organic optoelectronic device.

[0047] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0048]

Beneficial Effects

[0049] An organic optoelectronic device having high efficiency and long lifetime can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0051] Description of Reference Numerals

[0052] 100: Organic light-emitting diode

[0053] 105: Organic layer

[0054] 110: cathode

[0055] 120: Anode

[0056] 130: Luminous layer

[0057] 140: Hole transport zone

[0058] 150: Electron transport region DETAILED DESCRIPTION

[0059] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0060] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0061] In one embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylamine, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl or C2 to C30 heteroaryl. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, C1 to C20 alkyl, C6 to C30 arylamine, C6 to C30 aryl or C2 to C30 heteroaryl. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, C1 to C5 alkyl, C6 to C20 arylamine, C6 to C18 aryl, dibenzofuranyl, dibenzothienyl, carbazolyl or pyridyl. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, C6 to C20 arylamine, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or pyridyl.

[0062] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0063] In the present specification, "hydrogen substitution (—H)" may include "deuterium substitution (—D)" or "tritium substitution (—T)".

[0064] In the present specification, when a definition is not otherwise provided, "hetero" means including one to three hetero atoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0065] In the present specification, "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, quaterphenyl, etc., and two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0066] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0067] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound 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 contain one or more heteroatoms.

[0068] For example, "heteroaryl" may refer to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings may be fused. When the heteroaryl is a fused ring, each ring may include 1 to 3 heteroatoms.

[0069] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetraphenyl group, a substituted or unsubstituted 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 include, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0070] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl, 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 benzophenone, or a substituted or unsubstituted benzophenone. The invention may include, but is not limited to, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.

[0071] In this specification, hole characteristics refer to the ability to contribute 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.

[0072] 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.

[0073] Hereinafter, a composition for an organic optoelectronic device according to one embodiment is described.

[0074] The composition for an organic optoelectronic device according to one embodiment is a mixture including three types of compounds, specifically, a first compound having electron characteristics, a second compound having hole characteristics, and a third compound having buffer characteristics.

[0075] The third compound is a compound having a wide HOMO-LUMO band gap including both the HOMO-LUMO band gaps of the first compound and the second compound, and having a hole mobility lower than that of the second compound having hole characteristics, which slows down the hole injection characteristics and can bring about the effect of reducing hole traps.

[0076] In addition, since the third compound has lower electron mobility than the first compound and the light-emitting layer region is relatively moved toward the hole transport auxiliary layer, exciton quenching and resulting degradation at the interface with the electron transport auxiliary layer can be reduced, and thus the lifespan can be increased.

[0077] The first compound having electronic characteristics has a structure in which a triphenylene group or a triphenylene group derivative is substituted with a nitrogen-containing 6-membered ring and is represented by Chemical Formula 1.

[0078] [Chemical formula 1]

[0079]

[0080] In Chemical Formula 1,

[0081] Z 1 To Z 3 N or CL a -R a ,

[0082] Z 1 To Z 3 At least two of them are N,

[0083] L a and L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0084] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0085] R a and R 1 To R 3 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof,

[0086] R a Each exists independently or is connected to Ar 1 or Ar 2 To form a substituted or unsubstituted heteroaromatic polycyclic ring,

[0087] R 1 To R 3Each exists independently or adjacent groups therein are linked to form a substituted or unsubstituted heteroaromatic polycyclic ring,

[0088] m1 is an integer from 1 to 3, and

[0089] m2 and m3 are each independently one of integers from 1 to 4.

[0090] When m1 is 2 or greater, each R 1 Can be the same or different.

[0091] When m2 is 2 or greater, each R 2 Can be the same or different.

[0092] When m3 is 2 or greater, each R 3 Can be the same or different.

[0093] For example, Z in Formula 1 1 To Z 3 They can each be N.

[0094] For example, Z 1 and Z 2 Can be N and Z 3 Can be CL a -R a , where L a can be a single bond and R a Can be connected to the adjacent R 2 A substituted or unsubstituted heteroaromatic polycyclic ring is formed, for example, a substituted or unsubstituted benzothiophene pyrimidine.

[0095] For example, Z 1 and Z 3 Can be N and Z 2 Can be CL a -R a , where L a can be a single bond, and R a Can be connected to the adjacent R 1 A substituted or unsubstituted heteroaromatic polycyclic ring is formed, for example, a substituted or unsubstituted benzothiophene pyrimidine.

[0096] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-1 to Chemical Formula 1-3.

[0097] [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3]

[0098]

[0099] In Chemical Formulae 1-1 to 1-3, R 1 To R 3, L 1 To L 3 ,Ar 1 ,Ar 2 and m1 to m3 are defined the same as above,

[0100] R 16 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or a combination thereof, and

[0101] m16 is an integer between 1 and 4.

[0102] When m16 is 2 or greater, each R 16 Can be the same or different.

[0103] In one embodiment, each R 16 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0104] Specifically, L in Chemical Formula 1 1 To L 3 Each independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0105] Specifically, Ar in Chemical Formula 1 1 and Ar 2 Each of them may independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted indolocarbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted fused carbazolyl, a substituted or unsubstituted fused dibenzofuranyl, a substituted or unsubstituted fused dibenzothienyl, a substituted or unsubstituted fused indolocarbazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, or a substituted or unsubstituted benzoquinazolinyl.

[0106] For example, Ar in Formula 1 1 and Ar 2 Each of them may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

[0107] Specifically, R in Chemical Formula 1 1 To R 3 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0108] For example, R in Formula 1 1 To R 3 and may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0109] For example, R 1 To R 3 It can be linked to adjacent groups to form a substituted or unsubstituted heteroaromatic polycyclic ring, such as a substituted or unsubstituted benzofuran pyrimidine or a substituted or unsubstituted benzothiophene pyrimidine.

[0110] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-4 to Chemical Formula 1-6.

[0111]

[0112] In Chemical Formulae 1-4 to 1-6, Z 1 To Z 3 , R 1 To R 3 , L 1 To L 3 ,Ar 1 ,Ar 2 and m1 to m3 are defined the same as above,

[0113] X 1 is O or S,

[0114] R 17 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof,

[0115] m17 is an integer from 1 to 4,

[0116] m1' is 1, and

[0117] m3' is an integer of 1 or 2.

[0118] When m3' is 2 or greater, each R 3 Can be the same or different.

[0119] When m17 is 2 or greater, each R 17Can be the same or different.

[0120] In one embodiment, each R 17 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0121] According to the inclusion of Z 1 To Z 3 The substitution position of the 6-membered ring of Chemical Formula 1 can be represented by, for example, Chemical Formula 1-A or Chemical Formula 1-B.

[0122]

[0123] In Chemical Formula 1-A and Chemical Formula 1-B, Z 1 To Z 3 , L 1 To L 3 , R 1 To R 3 , L 1 To L 3 ,Ar 1 ,Ar 2 The definitions of and m1 to m3 are the same as above.

[0124] In a specific embodiment of the present invention, the first compound may be represented by Chemical Formula 1-A.

[0125] The first compound may be, for example, one selected from the compounds listed in Group 1.

[0126] [Group 1]

[0127]

[0128]

[0129]

[0130]

[0131] The second compound having a vacancy characteristic has a structure in which carbazole or indolocarbazole is substituted with a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, and is represented by, for example, Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4.

[0132] [Chemical formula 2]

[0133]

[0134] In chemical formula 2,

[0135] Ar 3and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0136] L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0137] R 4 To R 8 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0138] m5 and m6 are each independently an integer from 1 to 3,

[0139] m4, m7 and m8 are each independently one of integers from 1 to 4, and

[0140] n is an integer from 0 to 2;

[0141]

[0142] Wherein, in chemical formulas 3 and 4,

[0143] Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0144] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL b -R b ,

[0145] Among a1* to a4* in Chemical Formula 3, adjacent two are connected to * in Chemical Formula 4,

[0146] L b , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0147] R b , R 9 and R 10 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and

[0148] m9 and m10 are each independently one of integers from 1 to 4.

[0149] When m4 is 2 or greater, each R 4 Can be the same or different.

[0150] When m5 is 2 or greater, each R 5 Can be the same or different.

[0151] When m6 is 2 or greater, each R 6 Can be the same or different.

[0152] When m7 is 2 or greater, each R 6 Can be the same or different.

[0153] When m8 is 2 or greater, each R 8 Can be the same or different.

[0154] When m9 is 2 or greater, each R 9 Can be the same or different.

[0155] When m10 is 2 or greater, each R 10 Can be the same or different.

[0156] For example, in Formula 2, Ar 3 and Ar 4 Each may independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0157] For example, in Formula 2, Ar 3 and Ar 4 may be each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, and Ar 3 and Ar 4 At least one of may be a C6 to C20 aryl group which may be substituted or unsubstituted by one or more deuteriums or a C2 to C20 heterocyclic group which may be substituted or unsubstituted by one or more deuteriums.

[0158] For example, in Formula 2, R 4 To R 8 Each may independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic group.

[0159] For example, in Formula 2, R 4 To R 8may each independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic group, and R 4 To R 8 At least one of may be deuterium, a C1-C10 alkyl group substituted or unsubstituted by one or more deuterium, a C6-C20 aryl group substituted or unsubstituted by one or more deuterium, or a C2-C20 heterocyclyl group substituted or unsubstituted by one or more deuterium.

[0160] For example, in Formula 2, Ar 3 and Ar 4 At least one of may be a C6 to C20 aryl group which may be substituted by one or more deuteriums or a C2 to C20 heterocyclic group which may be substituted by one or more deuteriums, and R 4 To R 8 At least one of may be deuterium, a C1 to C10 alkyl group which may be substituted or not substituted by one or more deuteriums, a C6 to C20 aryl group which may be substituted or not substituted by one or more deuteriums, or a C2 to C20 heterocyclic group which may be substituted or not substituted by one or more deuteriums.

[0161] As a specific example, in Chemical Formula 2, Ar 3 and Ar 4 Each may independently be a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0162] As a specific example, in Chemical Formula 2, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group, and Ar 3 and Ar 4 At least one of them may be a C6 to C20 aryl group substituted or unsubstituted by one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted by one or more deuteriums, a dibenzothiophenyl group substituted or unsubstituted by one or more deuteriums, or a carbazolyl group substituted or unsubstituted by one or more deuteriums.

[0163] As a specific example, in Chemical Formula 2, Ar 3 and Ar 4 At least one of may be a C6 to C20 aryl group substituted or unsubstituted by one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted by one or more deuteriums, a dibenzothiophenyl group substituted or unsubstituted by one or more deuteriums, or a carbazolyl group substituted or unsubstituted by one or more deuteriums, and R4 To R 8 At least one of may be deuterium, a C1-C10 alkyl group which may be substituted or not substituted by one or more deuteriums, a C6-C20 aryl group which may be substituted or not substituted by one or more deuteriums, or a C2 to C20 heterocyclic group which may be substituted or not substituted by one or more deuteriums.

[0164] For example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 Each may independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0165] For example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 may be each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, and Ar 5 and Ar 6 At least one of may be a C6 to C20 aryl group which may be substituted or unsubstituted by one or more deuteriums or a C2 to C20 heterocyclic group which may be substituted or unsubstituted by one or more deuteriums.

[0166] For example, in Chemical Formula 3 and Chemical Formula 4, R b , R 9 and R 10 Each may independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic group.

[0167] For example, in Chemical Formula 3 and Chemical Formula 4, R b , R 9 and R 10 may each independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic group, and R b , R 9 and R 10 At least one of may be deuterium, a C1-C10 alkyl group which may be substituted or not substituted by one or more deuteriums, a C6-C20 aryl group which may be substituted or not substituted by one or more deuteriums, or a C2 to C20 heterocyclic group which may be substituted or not substituted by one or more deuteriums.

[0168] For example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6At least one of may be a C6 to C20 aryl group which may be substituted by one or more deuteriums or a C2 to C20 heterocyclic group which may be substituted by one or more deuteriums, and R b , R 9 and R 10 At least one of may be deuterium, a C1 to C10 alkyl group which may be substituted or not substituted by one or more deuteriums, a C6 to C20 aryl group which may be substituted or not substituted by one or more deuteriums, or a C2 to C20 heterocyclic group which may be substituted or not substituted by one or more deuteriums.

[0169] As a specific example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 Each may independently be a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0170] As a specific example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 may each independently be a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group, and Ar 5 and Ar 6 At least one of them may be a C6 to C20 aryl group substituted or unsubstituted by one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted by one or more deuteriums, a dibenzothiophenyl group substituted or unsubstituted by one or more deuteriums, or a carbazolyl group substituted or unsubstituted by one or more deuteriums.

[0171] As a specific example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 At least one of may be a C6 to C20 aryl group substituted or unsubstituted by one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted by one or more deuteriums, a dibenzothiophenyl group substituted or unsubstituted by one or more deuteriums, or a carbazolyl group substituted or unsubstituted by one or more deuteriums, and R b , R 9 and R 10 At least one of may be deuterium, a C1-C10 alkyl group which may be substituted or not substituted by one or more deuteriums, a C6-C20 aryl group which may be substituted or not substituted by one or more deuteriums, or a C2 to C20 heterocyclic group which may be substituted or not substituted by one or more deuteriums.

[0172] As a more specific example, in Chemical Formula 2, Ar 3 and Ar 4may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted fluorenyl group,

[0173] In chemical formula 2, L 3 and L 4 may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group,

[0174] In chemical formula 2, R 4 To R 8 may each independently be hydrogen, deuterium, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0175] n can be 0 or 1.

[0176] For example, in Formula 2, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0177] Ar 3 and Ar 4 At least one of the may be a phenyl group substituted or unsubstituted by one or more deuteriums, a biphenyl group substituted or unsubstituted by one or more deuteriums, a terphenyl group substituted or unsubstituted by one or more deuteriums, a naphthyl group substituted or unsubstituted by one or more deuteriums, an anthracenyl group substituted or unsubstituted by one or more deuteriums, a phenanthryl group substituted or unsubstituted by one or more deuteriums, a triphenylene group substituted or unsubstituted by one or more deuteriums, a carbazolyl group substituted or unsubstituted by one or more deuteriums, a dibenzothiophenyl group substituted or unsubstituted by one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted by one or more deuteriums, or a fluorenyl group substituted or unsubstituted by one or more deuteriums.

[0178] For example, in Formula 2, R 4 To R 8may each independently be hydrogen, deuterium, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0179] R 4 To R 8 At least one of them may be deuterium, a C6 to C12 aryl group substituted or unsubstituted by one or more deuteriums, a carbazole group substituted or unsubstituted by one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted by one or more deuteriums, or a dibenzothiophenyl group substituted or unsubstituted by one or more deuteriums.

[0180] For example, in Formula 2, Ar 3 and Ar 4 At least one of the following may be phenyl substituted or unsubstituted by one or more deuterium groups, biphenyl substituted or unsubstituted by one or more deuterium groups, terphenyl substituted or unsubstituted by one or more deuterium groups, naphthyl substituted or unsubstituted by one or more deuterium groups, anthracenyl substituted or unsubstituted by one or more deuterium groups, phenanthryl substituted or unsubstituted by one or more deuterium groups, triphenylene substituted or unsubstituted by one or more deuterium groups, carbazolyl substituted or unsubstituted by one or more deuterium groups, dibenzothiophenyl substituted or unsubstituted by one or more deuterium groups, dibenzofuranyl substituted or unsubstituted by one or more deuterium groups, or fluorenyl substituted or unsubstituted by one or more deuterium groups, and

[0181] In chemical formula 2, R 4 To R 8 At least one of them may be deuterium, a C6 to C12 aryl group substituted or unsubstituted by one or more deuteriums, a carbazole group substituted or unsubstituted by one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted by one or more deuteriums, or a dibenzothiophenyl group substituted or unsubstituted by one or more deuteriums.

[0182] As an example, in Chemical Formula 2, “substituted” means 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.

[0183] In a specific embodiment of the present invention, Chemical Formula 2 may be represented by one of Chemical Formula 2-1 to Chemical Formula 2-15.

[0184]

[0185]

[0186] In Chemical Formulae 2-1 to 2-15, R 4 To R 8may each independently be hydrogen, deuterium, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and L 3 -Ar 3 and L 4 -Ar 4 may each independently be one of the substituents listed in Group I.

[0187] [Group I]

[0188]

[0189] In Group I,

[0190] R 59 To R 62 are each independently hydrogen, deuterium, C1 to C4 alkyl, C6 to C18 aryl or C2 to C30 heteroaryl,

[0191] m19 is an integer from 1 to 5,

[0192] m20 is an integer from 1 to 4,

[0193] m21 is an integer from 1 to 3,

[0194] m12 is an integer of 1 or 2, and

[0195] * is the connection point.

[0196] When m19 is 2 or greater, each R 59 Can be the same or different.

[0197] When m20 is 2 or more, each R 60 Can be the same or different.

[0198] When m21 is 2 or greater, each R 61 Can be the same or different.

[0199] When m22 is 2 or greater, each R 62 Can be the same or different.

[0200] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0201] In addition, in Chemical Formula 2-8, L 3 -Ar 3 and L 4 -Ar 4 may be each independently selected from Group I, and may be, for example, any one of C-1, C-2, C-3, C-4, C-7, C-8, and C-9.

[0202] For example, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0203]

[0204] In Chemical Formulae 3A to 3E, Ar 5 ,Ar 6 , L 5 , L 6 , R 9 and R 10 Same as above,

[0205] L bl To L b4 Definition and above L 5 and L 6 The same, and

[0206] R b1 To R b4 Definition and above R 9 and R 10 same.

[0207] For example, in Formulas 3 and 4, Ar 5 and Ar 6 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0208] R b1 To R b4 , R 9 and R 10 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0209] In a specific embodiment of the present invention, in Chemical Formulae 3 and 4, L 5 -Ar 5 and L 6 -Ar 6 The substituents listed in Group I may be each independently selected.

[0210] In one embodiment, R b1 To R b4 , R 9 and R 10Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0211] For example, R b1 To R b4 , R 9 and R 10 may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and

[0212] In a specific embodiment, R b1 To R b4 , R 9 and R 10 Each may independently be hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.

[0213] For example, in Formulas 3 and 4, Ar 5 and Ar 6 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0214] Ar 5 and Ar 6 At least one of the may be a phenyl group substituted or unsubstituted by one or more deuterium groups, a biphenyl group substituted or unsubstituted by one or more deuterium groups, a naphthyl group substituted or unsubstituted by one or more deuterium groups, a triphenylene group substituted or unsubstituted by one or more deuterium groups, a carbazolyl group substituted or unsubstituted by one or more deuterium groups, a dibenzofuranyl group substituted or unsubstituted by one or more deuterium groups, or a dibenzothiophenyl group substituted or unsubstituted by one or more deuterium groups.

[0215] For example, in Formulas 3 and 4, R b1 To R b4 , R 9 and R 10 may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and

[0216] R b1 To R b4 , R 9 and R10 At least one of them may be deuterium, phenyl substituted or unsubstituted by one or more deuterium, biphenyl substituted or unsubstituted by one or more deuterium, carbazolyl substituted or unsubstituted by one or more deuterium, dibenzofuranyl substituted or unsubstituted by one or more deuterium, or dibenzothiophenyl substituted or unsubstituted by one or more deuterium.

[0217] For example, in Formulas 3 and 4, Ar 5 and Ar 6 At least one of the following may be a phenyl group substituted or unsubstituted by one or more deuterium groups, a biphenyl group substituted or unsubstituted by one or more deuterium groups, a naphthyl group substituted or unsubstituted by one or more deuterium groups, a triphenylene group substituted or unsubstituted by one or more deuterium groups, a carbazolyl group substituted or unsubstituted by one or more deuterium groups, a dibenzofuranyl group substituted or unsubstituted by one or more deuterium groups, or a dibenzothiophenyl group substituted or unsubstituted by one or more deuterium groups, and

[0218] R b1 To R b4 , R 9 and R 10 At least one of them may be deuterium, phenyl substituted or unsubstituted by one or more deuterium, biphenyl substituted or unsubstituted by one or more deuterium, carbazolyl substituted or unsubstituted by one or more deuterium, dibenzofuranyl substituted or unsubstituted by one or more deuterium, or dibenzothiophenyl substituted or unsubstituted by one or more deuterium.

[0219] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 2-8, wherein in Chemical Formula 2-8, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted fluorenyl group, and L 3 and L 4 may be each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 4 To R 8 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0220] In one embodiment of the present invention, the second compound can be represented by Chemical Formula 3C, wherein in Chemical Formula 3C, L b1 and Lb2 Can be a single bond, L 5 and L 6 may be each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R b1 , R b2 , R 9 and R 10 may each independently be hydrogen, deuterium, phenyl, triphenylene, carbazolyl, dibenzofuranyl or dibenzothiophenyl, and Ar 5 and Ar 6 Each of them independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0221] For example, the second compound may be one selected from the compounds listed in Group 2, but is not limited thereto.

[0222] [Group 2]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] The third compound having buffer properties has a structure in which a triphenylene group is substituted with 9-carbazole and is represented by Chemical Formula 5.

[0237] [Chemical formula 5]

[0238]

[0239] In Chemical Formula 5,

[0240] R 11 To R 15 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof, L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0241] m11, m12, m14 and m15 are each independently one of integers from 1 to 4, and m13 is one of integers from 1 to 3.

[0242] When m11 is 2 or greater, each R 11 Can be the same or different.

[0243] When m12 is 2 or greater, each R 12 Can be the same or different.

[0244] When m13 is 2 or greater, each R 13 Can be the same or different.

[0245] When m14 is 2 or greater, each R 14 Can be the same or different.

[0246] When m15 is 2 or greater, each R 15 Can be the same or different.

[0247] Specifically, L 7 It may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0248] More specifically, L 7 It may be a single bond, a substituted or unsubstituted phenylene (including at least one of m-phenylene and p-phenylene), a substituted or unsubstituted biphenylene (including at least one of m-phenylene and p-phenylene), or a triphenylene (including at least one of m-phenylene and p-phenylene).

[0249] For example, L 7 It may be a single bond or may be selected from the linking groups listed in Group II.

[0250] [Group II]

[0251]

[0252] In Group II,

[0253] R 55 To R 66 are each independently hydrogen, deuterium, C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, halogen, cyano or a combination thereof, and

[0254] * is the connection point.

[0255] For example, it may be represented by any one of Chemical Formula 5-I to Chemical Formula 5-III.

[0256]

[0257]

[0258] [Chemical Formula 5-III]

[0259]

[0260] In Chemical Formulae 5-I to 5-III, R 11 To R 15 , R 18 and m11 to m15 are the same as above, and

[0261] m18 is an integer between 1 and 4.

[0262] When m18 is 2 or greater, each R 18 Can be the same or different.

[0263] For example, the third compound may be represented by Chemical Formula 5-II.

[0264] Specifically, in Chemical Formula 5, R 11 To R 13 and may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0265] Specifically, in Chemical Formula 5, R 14 and R 15 Each of them may independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0266] The third compound may be, for example, one selected from the compounds listed in Group 3.

[0267] [Group 3]

[0268]

[0269]

[0270]

[0271] The first compound includes a nitrogen-containing 6-membered ring having high electron transport characteristics, and thus can stably and efficiently transport electrons to reduce driving voltage, improve current efficiency, and achieve long life characteristics of the device.

[0272] The second compound has a structure including carbazole having a high HOMO energy, and thus can efficiently inject and transport holes, thereby contributing to improving device characteristics.

[0273] The third compound has a wide HOMO-LUMO band gap, thereby controlling the movement rates of holes and electrons of the first compound and the second compound, and thus can prevent hole capture and exciton quenching by relative movement of the light-emitting layer region, which helps to improve the life characteristics of the device.

[0274] Compared with this composition, a triple-host composition comprising a first compound, a second compound, and a third compound can achieve an optimal balance by more finely adjusting the electron / hole characteristics of the device stack, and compared with a dual-host composition, such as a composition comprising a first compound and a second compound or a composition comprising a first compound and a third compound, the device characteristics can be greatly improved due to the proper balance of charges.

[0275] Furthermore, the triple-host composition can further improve lifespan characteristics and efficiency characteristics by optimally adjusting the balance of electron / hole characteristics compared to other triple-host compositions having different combinations obtained therefrom.

[0276] In the most specific embodiment of the present invention, the first compound may be represented by Chemical Formula 1-A, the second compound may be represented by any one of Chemical Formulas 2-6, 2-8 and 3C, and the third compound may be represented by Chemical Formula 5-II.

[0277] Such a mixed composition of the first compound, the second compound, and the third compound may be included, for example, as a phosphorescent host in a light-emitting layer of an organic light-emitting diode to be described later.

[0278] In the composition for an organic optoelectronic device, the first compound may be included in an amount of about 20 wt % to 50 wt % based on the total weight of the first compound, the second compound may be included in an amount of about 40 wt % to 60 wt % based on the total weight of the first compound and the second compound, and the second compound may be included in an amount of about 10 wt % to 30 wt % based on the total weight of the first compound, the second compound and the third compound.

[0279] Within the above range, for example, the first compound for an organic optoelectronic device may be included in an amount of about 25 wt % to 45 wt % based on the total weight of the first compound for an organic optoelectronic device, the second compound for an organic optoelectronic device, and the third compound for an organic optoelectronic device, the second compound for an organic optoelectronic device may be included in an amount of about 45 wt % to 60 wt % based on the total weight of the first compound for an organic optoelectronic device, the second compound for an organic optoelectronic device, and the third compound for an organic optoelectronic device, and the third compound for an organic optoelectronic device may be included in an amount of about 10 wt % to 25 wt % based on the total weight of the first compound for an organic optoelectronic device, the second compound for an organic optoelectronic device, and the third compound for an organic optoelectronic device.

[0280] In addition, as a specific example, the first compound can be included in an amount of about 30wt% to 40wt% based on the total weight of the first compound, the second compound, and the third compound, the second compound can be included in an amount of about 45wt% to 55wt% based on the total weight of the first compound, the second compound, and the third compound, and the third compound can be included in an amount of about 10wt% to 20wt% based on the total weight of the first compound, the second compound, and the third compound.

[0281] As a more specific example, the composition for an organic optoelectronic device may include a weight ratio of the first compound: the second compound: the third compound of about 35:55:10 or about 32:48:20. Within the above range, the electron transport ability of the first compound, the hole transport ability of the second compound, and the buffering ability of the third compound are appropriately coordinated to improve the efficiency and life of the device.

[0282] The composition for an organic optoelectronic device may further include one or more compounds in addition to the first compound, the second compound, and the third compound.

[0283] The composition for an organic optoelectronic device may further include a dopant. The dopant may be, for example, a phosphorescent dopant such as a red, green, or blue phosphorescent dopant, and may be, for example, a green phosphorescent dopant.

[0284] The dopant is a material mixed with the first compound, the second compound, and the third compound in a trace amount to cause luminescence, and generally can be a material that emits light by multiple excitations to a triplet state or more, such as a metal complex. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof can be used.

[0285] An embodiment of the dopant may be a phosphorescent dopant, and an embodiment 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.

[0286] [Chemical formula Z]

[0287] L 9 MX 2

[0288] In the chemical formula Z, M is a metal and L 9 and X 2 are the same or different and are ligands that form a complex with M.

[0289] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 9 and X 2 This may be, for example, a bidentate ligand.

[0290] By L 9 and X 2 Examples of the ligands represented may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0291] [Group A]

[0292]

[0293]

[0294] In Group A,

[0295] R 300 To R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen, C6 to C30 aryl which may be substituted by C1 to C30 alkyl, or halogen, and

[0296] R 303 To R 324Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amine, substituted or unsubstituted C6 to C30 arylamine, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0297] For example, a dopant represented by Chemical Formula IV may be further included.

[0298] [Chemical Formula IV]

[0299]

[0300] In chemical formula IV,

[0301] R 101 To R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0302] R 132 To R 134 are each independently C1 to C6 alkyl,

[0303] R 101 To R 116 At least one of them is a functional group represented by Chemical Formula IV-1,

[0304] L 100 is a bidentate ligand coordinated to a single anion by an unshared carbon or heteroatom electron pair.

[0305] n1 and n2 are each independently any one of integers from 0 to 3, and n1+n2 is any one of integers from 1 to 3,

[0306] [Chemical Formula IV-1]

[0307]

[0308] In Chemical Formula IV-1,

[0309] R 135 To R 139are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,and

[0310] * indicates a moiety attached to a carbon atom.

[0311] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0312] [Chemical formula Z-1]

[0313]

[0314] In the chemical formula Z-1, rings A, B, C and D independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0315] R A , R B , R C and R D independently represents mono-, di-, tri- or tetra-substituted, or unsubstituted;

[0316] L B , L C and L D Each is independently selected from a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0317] When nA is 1, L E is selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof; when nA is 0, L E does not exist; and

[0318] R A , R B , R C , R D R, R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amine, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfhydryl, sulfinyl, sulfonyl, phosphino and combinations thereof; any adjacent R A , R B , R C , R D , R and R' are optionally linked to each other to provide a ring; X B , X C, X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a direct bond.

[0319] In one embodiment, the dopant may be a platinum complex and may be represented by Formula V, for example.

[0320] [Chemical Formula V]

[0321]

[0322] In chemical formula V,

[0323] X 100 Selected from O, S and NR 131 ,

[0324] R 117 To R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0325] R 132 To R 134 are each independently C1 to C6 alkyl, and

[0326] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl.

[0327] The composition for an organic optoelectronic device may be formed by a dry film deposition method such as chemical vapor deposition.

[0328] Hereinafter, an organic optoelectronic device using the above-mentioned composition for an organic optoelectronic device is described.

[0329] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa, for example, an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photoconductor.

[0330] Herein, an organic light emitting diode as one embodiment of an organic optoelectronic device is described with reference to the accompanying drawings.

[0331] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0332] refer to 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 .

[0333] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0334] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may include 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.

[0335] The organic layer 105 may include the above-described composition for an organic optoelectronic device.

[0336] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described composition for an organic optoelectronic device.

[0337] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light emitting composition.

[0338] The light emitting layer 130 may include, for example, the above-described composition for an organic optoelectronic device as a phosphorescent host.

[0339] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0340] The charge transport region may be, for example, a hole transport region 140 .

[0341] The hole transport region 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 , and block electrons.

[0342] Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130 and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, and at least one of the group B compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0343] [Group B]

[0344]

[0345]

[0346]

[0347]

[0348] In the hole transport region, in addition to the above-mentioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having similar structures can be used.

[0349] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0350] The electron transport region 150 may further increase electron injection and / or electron mobility and block holes between the cathode 110 and the light emitting layer 130 .

[0351] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer, and at least one of the group C compounds may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0352] [Group C]

[0353]

[0354]

[0355]

[0356]

[0357] One embodiment may be an organic light emitting diode including a light emitting layer as an organic layer.

[0358] Another embodiment may be an organic light emitting diode including a light emitting layer and a hole transporting region as organic layers.

[0359] Another embodiment may be an organic light emitting diode including a light emitting layer and an electron transporting region as organic layers.

[0360] Another embodiment of the present invention may provide an organic light emitting diode including a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130, such as Figure 1 as shown in .

[0361] On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as an organic layer in addition to the light emitting layer.

[0362] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, and then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming the cathode or anode thereon.

[0363] The organic light emitting diode may be applied to an organic light emitting display device.

[0364] [Specific implementation plan]

[0365] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the claims is not limited thereto.

[0366] (Synthesis of the First Compound)

[0367] Synthesis Example 1: Synthesis of Compound 1-2

[0368] [Reaction 1]

[0369]

[0370] In a round-bottom flask, under a nitrogen stream, 20.00 g (48.16 mmol) of 4,4,5,5-tetramethyl-2-(3-(triphenylene-2-yl)phenyl)-1,3,2-dioxaborolane, 17.38 g (50.56 mmol) of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, 16.6 g (120.39 mmol) of K2CO3 and 1.67 g (1.67 mmol) of Pd(PPh3)4 were suspended in 140 ml of THF and 60 ml of distilled water, and then stirred and refluxed for 8 hours. When the reaction was complete, after separating the layers, the THF layer obtained therefrom was concentrated. The concentrated THF layer was dissolved in DCB (dichlorobenzene), and then recrystallized to obtain a solid, which was 23 g of compound 1-2 (78%).

[0371] Synthesis Example 2: Synthesis of Compound 1-3

[0372] [Reaction 2]

[0373]

[0374] Step 1: Synthesis of intermediate 1-3-1

[0375] 40g (92.95mmol) of 4,4,5,5-tetramethyl-2-(3-(triphenylene-2-yl)phenyl)-1,3,2-dioxaborolane, 18.68g (97.56mmol) of 1-bromo-3-chlorobenzene, 32.12g (232.37mmol) of K2CO3 and 3.22g (2.79mmol) of Pd(PPh3)4 were suspended in 240ml of THF and 120ml of distilled water under a nitrogen stream, and then stirred and refluxed for 8 hours. When the reaction was completed, the THF layer obtained therefrom was concentrated to obtain a solid, which was dissolved in xylene, and then recrystallized to obtain 23g (60%) of intermediate 1-3-1.

[0376] Step 2: Synthesis of intermediate 1-3-2

[0377] 23g (55.43mmol) of intermediate 1-3-1, 21.11g (83.15mmol) of bis (pinacolato) diboron, 2.26g (2.77mmol) of Pd (dppf) Cl 2 and 10.88g (110.86mmol) of potassium acetate were added to a round-bottomed flask and then dissolved in 250ml of DMF (dimethylformamide). The mixture was stirred and refluxed at 120°C for 12 hours. When the reaction was complete, the mixture was poured into excessive distilled water and then stirred for 1 hour. Solids were filtered therefrom and then dissolved in xylene. After removing moisture with MgSO 4, organic solvents were also filtered and removed under reduced pressure by using a silica gel pad. Solids were recrystallized therefrom with xylene to obtain 26.5g (89%) of intermediate 1-3-2.

[0378] Step 3: Synthesis of Compound 1-3

[0379] Under nitrogen flow, 26.5g (52.33mmol) of intermediate 1-3-2, 18.89g (54.94mmol) of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, 18.08g (130.82mmol) of K2CO3 and 1.81g (1.57mmol) of Pd (PPh3)4 were suspended in 140ml of THF and 70ml of distilled water, and then stirred and refluxed for 8 hours. When the reaction was complete, MeOH was added thereto to obtain a solid, which was filtered. Subsequently, the solid was dissolved in MCB and then filtered using a silica gel pad to remove the organic solvent under reduced pressure. The solid was recrystallized from it with MCB to obtain 26.6g of compound 1-3 (74%).

[0380] (Synthesis of the Second Compound)

[0381] Synthesis Example 3: Synthesis of Compound B-31

[0382] It was synthesized using the same method described in KR10-2017-0037277A.

[0383] Synthesis Example 4: Synthesis of Compound C-5

[0384] [Reaction 3]

[0385]

[0386] Step 1: Synthesis of intermediate 2-15-1

[0387] In a round-bottom flask, 10.44 g (42.41 mmol) of 4-bromo-9H-carbazole, 11.88 g (42.41 mmol) of 4-iodo-1,1'-biphenyl (Sigma Aldrich Co., Ltd.), 0.388 g (0.424 mmol) of Pd2(dba)3, 0.206 g (0.848 mmol) of P(t-Bu)3 and 6.11 g (63.61 mmol) of NaO(t-Bu) were suspended in 420 ml of toluene, and then stirred at 60°C for 12 hours. When the reaction was completed, distilled water was added thereto, and then stirred for 30 minutes to extract the organic layer, which was subjected to a silica gel column treatment (hexane / dichloromethane=9:1 (v / v)) to obtain 14.70 g (yield: 87%) of intermediate 2-15-1.

[0388] Step 2: Synthesis of intermediate 2-15-2

[0389] In a round-bottom flask, 15.50 g (38.92 mmol) of the synthetic intermediate 2-15-1, 7.15 g (42.81 mmol) (2-nitrophenyl) -boric acid, 16.14 g (116.75 mmol) potassium carbonate, 1.35 g (1.17 mmmol) tetrakis - (triphenylphosphine) palladium (0) (Pd (PPh3) 4) were suspended in 150 ml of toluene and 70 ml of distilled water, and then stirred and refluxed for 12 hours. Subsequently, the organic layer was extracted therefrom with dichloromethane and distilled water, and then filtered through silica gel. After removing the organic solution therefrom, the solid produced therein was recrystallized with dichloromethane and n-hexane to obtain 13.72 g (yield: 80%) of the intermediate 2-15-2.

[0390] Step 3: Synthesis of intermediate 2-15-3

[0391] 22.46g (51.00mmol) of synthetic intermediate 2-15-2 and 52.8ml of triethyl phosphite were added to a round-bottomed flask, and after internal substitution with nitrogen, stirred at 160°C for 12 hours. When the reaction was complete, 3L of MeOH was added thereto, and then filtered to volatilize its filtrate. Then, 10.42g (yield: 50%) of intermediate 2-15-3 was obtained by purification by column chromatography (hexane).

[0392] Step 4: Synthesis of compound C-5

[0393] Compound C-5 was synthesized in the same manner as in the first step of Synthesis Example 4 (yield: 60%), except that Intermediate 2-15-3 and 3-iodo-1,1′-biphenyl were used.

[0394] (LC / MS: theoretical value 560.23 g / mol, measured value: 561.57 g / mol)

[0395] Synthesis Example 5: Synthesis of Compound B-186

[0396] [Reaction 4]

[0397]

[0398] Step 1: Synthesis of intermediate 2-13-1

[0399] In a round-bottom flask, 18.23 g (40.94 mmol) of 2-[9-([1,1'-biphenyl]-4-yl)-9H-carbazole-3-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 11.08 g (45.03 mmol) of 2-bromo-9H-carbazole, 11.32 g (81.88 mmol) of potassium carbonate and 1.42 g (1.23 mmmol) of tetrakis-(triphenylphosphine)palladium (0) (Pd(PPh3)4) were suspended in 180 ml of tetrahydrofuran (THF) and 75 ml of distilled water, and then stirred and refluxed. Subsequently, an organic layer was extracted therefrom with dichloromethane and distilled water, and then silica gel filtered. After removing the organic solution, the solid obtained therefrom was recrystallized with dichloromethane and n-hexane to obtain 18.05 g (yield: 91%) of Intermediate 2-13-1.

[0400] Step 2: Synthesis of Compound B-186

[0401] In a round-bottom flask, 13.29 g (27.42 mmol) of intermediate 2-13-1, 6.39 g (27.42 mmol) of 4-bromobiphenyl, 0.25 g (0.274 mmol) of Pd2(dba)3, 0.133 g (0.274 mmol) of P(t-Bu)3 and 3.95 g (41.13 mmol) of NaO(t-Bu) were suspended in 300 ml of toluene, and then stirred at 60°C for 12 hours. When the reaction was completed, distilled water was added thereto, and then stirred for 30 minutes to extract an organic layer, which was subjected to a silica gel column treatment (hexane / dichloromethane = 9:1 (v / v)) to obtain 15.37 g (yield: 88%) of compound B-186.

[0402] LC-Mass (theoretical value: 636.26 g / mol, measured value: M+=637.40 g / mol)

[0403] (Synthesis of the Third Compound)

[0404] Synthesis Example 6: Synthesis of Compound 3-6

[0405] [Reaction 5]

[0406]

[0407] Step 1: Synthesis of intermediate 3-6-1

[0408] Intermediate 3-6-1 was synthesized in the same manner as described in KR2014135532, except that 2,7-dibromotriphenylene (888041-37-0) was used.

[0409] Step 2: Synthesis of intermediate 3-6

[0410] 1 equivalent of intermediate 3-6-1 (65.23mmol), 1.1 equivalents of intermediate (3-(9H-carbazole-9-yl) phenyl) boronic acid (cas: 864377-33-3) (71.75mmol), 2.26g (1.96mmol) Pd (PPh3) 4 and 22.54g (163.07mmol) K2CO3 were suspended in 200ml THF and 100ml distilled water, and then stirred and refluxed for 12 hours. When the reaction was completed, after the resultant was cooled to room temperature, the solid produced therefrom was filtered, and then washed with distilled water and acetone. The solid was dissolved in 200ml dichlorobenzene by heating, filtered with silica gel, and then recrystallized in 500ml dichlorobenzene to synthesize compound 3-6 with a yield of 80%.

[0411] LC-Mass (theoretical value: 545.21 g / mol, measured value: M+=546.27 g / mol)

[0412] Synthesis Example 7: Synthesis of Compound 3-7

[0413] [Reaction 6]

[0414]

[0415] Step 1: Synthesis of 3-7

[0416] Compound 3-7 was synthesized in the same manner as the second step of Synthesis Example 5 with a yield of 85%, except that 1 equivalent of 2-(3-chlorophenyl)-triphenylene (cas: 1384206-44-3) and 1.05 equivalents of 2-phenyl-9H-carbazole (cas: 88590-00-5) were used.

[0417] LC-Mass (theoretical value: 545.21 g / mol, measured value: M+ = 546.24 g / mol)

[0418] Compound C1

[0419]

[0420] (Synthesis of dopant)

[0421] Synthesis Example 8: Synthesis of dopant compound PtGD

[0422] [PtGD]

[0423]

[0424] It was synthesized using the same method described in KR1999337.

[0425] (Manufacturing of organic light-emitting diodes)

[0426] Example 1

[0427] A glass substrate coated with an ITO (indium tin oxide) thin film 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 by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This prepared ITO transparent electrode was used as an anode, and Compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form A hole injection layer is formed on the hole injection layer to a thickness of Compound B is deposited on the hole transport layer to a thickness of Compound 1-3, compound 2-2 and compound 3-7 were simultaneously used as the host on the hole transport auxiliary layer, and 15 wt % of PtGD was doped as a dopant to form a hole transport auxiliary layer by vacuum deposition. Here, Compound 1-3, Compound 2-2, and Compound 3-7 were used in a weight ratio of 30:55:15, and the ratios are described separately for the following Examples and Comparative Examples. Then, Compound C was deposited on the light emitting layer to The electron transport auxiliary layer is formed by vacuum depositing compound D and LiQ at a weight ratio of 1:1 to form an electron transport layer. By sequentially vacuum depositing LiQ and Al forms the cathode to make organic light-emitting diodes.

[0428] ITO / Compound A (3% NDP-9 doping, ) / Compound A( ) / Compound B( ) / EML[1-3:2-2:3-7[PtGD](15wt%)]( ) / Compound C( ) / Compound D: LiQ( ) / LiQ( ) / Al( ).

[0429] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0430] Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0431] Compound C: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0432] Compound D: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0433] Examples 2 and 3

[0434] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to the host shown in Tables 1 to 3.

[0435] Comparative Examples 1 to 7

[0436] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to the host shown in Tables 1 to 3.

[0437] evaluate

[0438] The efficiency and lifetime of the organic light emitting diodes according to Examples 1 to 3 and Comparative Examples 1 to 7 were measured.

[0439] The measurement was performed in the following method, and the results are shown in Tables 1 to 3.

[0440] (1) Life measurement

[0441] In the case of brightness (cd / m 2 ) maintained at 24,000cd / m 2 At the same time, the lifespan was obtained by measuring the time until the current efficiency (cd / A) dropped to 95%. The results are shown as a relative lifespan ratio based on the lifespans of Comparative Examples 1, 4, and 6.

[0442] (2) Measuring the change in current density due to voltage change

[0443] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit device in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0444] (3) Measuring the change in brightness due to voltage changes

[0445] 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).

[0446] (4) Measurement of current efficiency

[0447] By using the luminance, current density and voltage measured in (1) and (2), the current efficiency (cd / A) at a desired luminance of 9000 nit is calculated. The current efficiency (cd / A) is shown as a relative efficiency ratio based on the current efficiencies of Comparative Examples 1, 4 and 6.

[0448] (Table 1)

[0449]

[0450] (Table 2)

[0451]

[0452] (Table 3)

[0453]

[0454] Referring to Tables 1 to 3, it is confirmed that the organic light emitting diodes of Examples 1 to 3 exhibit significantly improved lifespans while maintaining equivalent or higher efficiencies, compared to the organic light emitting diodes of Comparative Examples 1 to 7.

[0455] While the invention has been described in conjunction with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but 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 first compound; a second compound; and The third compound, in, The first compound is represented by Chemical Formula 1, The second compound is represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4, and The third compound is represented by Chemical Formula 5: [Chemical formula 1] Wherein, in Chemical Formula 1, Z 1 To Z 3 N or CL a -R a , Z 1 To Z 3 At least two of them are N, L a and L 1 To L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R a and R 1 To R 3 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof, R a Each exists independently or is connected to Ar 1 or Ar 2 To form a substituted or unsubstituted heteroaromatic polycyclic ring, R 1 To R 3 Each exists independently or adjacent groups therein are linked to form a substituted or unsubstituted heteroaromatic polycyclic ring, m1 is an integer from 1 to 3, and m2 and m3 are each independently an integer from 1 to 4; [Chemical formula 2] Wherein, in Chemical Formula 2, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 4 To R 8 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, m5 and m6 are each independently an integer from 1 to 3, m4, m7 and m8 are each independently one of integers from 1 to 4, and n is one of integers from 0 to 2; Wherein, in Chemical Formulas 3 and 4, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL b -R b , among a1* to a4* in Chemical Formula 3, two adjacent ones are connected to * in Chemical Formula 4, L b , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R b , R 9 and R 10 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m9 and m10 are each independently an integer from 1 to 4; [Chemical formula 5] Among them, in chemical formula 5, R 11 To R 15 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof, L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m11, m12, m14 and m15 are each independently one of integers from 1 to 4, and m13 is one of integers from 1 to 3.

2. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by any one of Chemical Formula 1-1 to Chemical Formula 1-3: In Chemical Formula 1-1 and Chemical Formula 1-3, R 1 To R 3 , L 1 To L 3 ,Ar 1 ,Ar 2 and m1 to m3 are the same as those in claim 1, R 16 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or a combination thereof, and m16 is an integer from 1 to 4.

3. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by any one of Chemical Formula 1-4 to Chemical Formula 1-6: Among them, in Chemical Formula 1-4 and Chemical Formula 1-6, Z 1 To Z 3 , R 1 To R 3 , L 1 To L 3 ,Ar 1 ,Ar 2 and m1 to m3 are the same as in claim 1, X 1 is O or S, R 17 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano or a combination thereof, m17 is an integer from 1 to 4, m1' is 1, and m3' is an integer of 1 or 2.

4. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by chemical formula 1-A: [Chemical Formula 1-A] Wherein, in Chemical Formula 1-A, Z 1 To Z 3 , L 1 To L 3 , R 1 To R 3 , L 1 To L 3 ,Ar 1 ,Ar 2 and m1 to m3 are the same as those in claim 1.

5. The composition for an organic optoelectronic device according to claim 1, wherein The second compound is represented by any one of Chemical Formula 2-6, Chemical Formula 2-8 and Chemical Formula 3C: Among them, in Chemical Formula 2-6, Chemical Formula 2-8 and Chemical Formula 3C, L 3 To L 6 ,Ar 3 To Ar 6 , R 4 To R 7 , R 9 , R 10 and m4 to m7, m8 and m9 are the same as those in claim 1, L b1 and L b2 The same as L in claim 1 b The definition of is the same as R bl and R b2 The same as in claim 1 b The definition is the same.

6. The composition for an organic optoelectronic device according to claim 1, wherein In Chemical Formula 5, L 7 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

7. The composition for an organic optoelectronic device according to claim 1, wherein In Chemical Formula 5, L 7 is a single bond or is one of the linking groups listed in Group II: [Group II] Among them, in Group II, R 55 To R 66 Each is independently hydrogen, deuterium, C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, halogen, cyano or a combination thereof, and * is a point of attachment.

8. The composition for an organic optoelectronic device according to claim 1, wherein The third compound is represented by any one of Chemical Formula 5-I to Chemical Formula 5-III: Wherein, in Chemical Formulae 5-I to 5-III, R 11 To R 15 , R 18 and m11 to m15 are the same as in claim 1.

9. The composition for an organic optoelectronic device according to claim 1, wherein In Chemical Formula 5, R 11 To R 13 and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

10. The composition for an organic optoelectronic device according to claim 1, wherein In Chemical Formula 5, R 14 and R 15 Each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

11. The composition for an organic optoelectronic device according to claim 1, wherein The first compound is represented by chemical formula 1-A, The second compound is represented by any one of Chemical Formula 2-6, Chemical Formula 2-8 and Chemical Formula 3C, and The third compound is represented by chemical formula 5-II: [Chemical Formula 1-A] Wherein, in Chemical Formula 1-A, Z 1 To Z 3 , L 1 To L 3 , R 1 To R 3 , L 1 To L 3 ,Ar 1 ,Ar 2 and m1 to m3 are the same as in claim 1; In Formula 2-6, Formula 2-8 and Formula 3C, R 4 To R 7 , R 9 , R 10 , m4 to m7, m9 and m10 are defined as in claim 1; [Chemical Formula 5-II] Wherein, in Chemical Formula 5-II, R 11 To R 15 , R 18 and m11 to m15 are as defined in claim 1, and m18 is one of integers from 1 to 4.

12. 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, in, The organic layer includes the composition for an organic optoelectronic device according to any one of claims 1 to 11 .

13. The organic optoelectronic device according to claim 12, wherein: The organic layer includes a light-emitting layer, and The light-emitting layer includes the composition for an organic optoelectronic device.

14. The organic optoelectronic device according to claim 13, wherein: Each of the first compound, the second compound, and the third compound is included as a phosphorescent host of the light emitting layer.

15. The organic optoelectronic device according to claim 14, wherein: The first compound is included in an amount of about 20 wt % to about 50 wt % based on the total weight of the first compound, the second compound and the third compound, The second compound is included in an amount of about 40 wt % to about 60 wt % based on the total weight of the first compound, the second compound and the third compound, and the third compound is included in an amount of about 10 wt % to about 30 wt % based on the total weight of the first compound, the second compound and the third compound.

16. The organic optoelectronic device according to claim 13, wherein: The composition for an organic optoelectronic device further includes a dopant.

17. The organic optoelectronic device according to claim 16, wherein: The composition for an organic optoelectronic device is a green light-emitting composition.

18. A display device comprising the organic optoelectronic device according to claim 12.

Images