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

Abstract

The present invention relates to a composition for an organic optoelectronic diode, and an organic optoelectronic diode 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] Compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices are disclosed. Background Art

[0002] An organic optoelectronic device (organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0003] According to the working principle, organic optoelectronic devices can be roughly divided into two categories. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, and the other is a light-emitting device that generates light energy from electrical energy by applying a voltage or current to an electrode.

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

[0005] Among them, due to the increasing demand for flat panel display devices, organic light-emitting diodes (OLEDs) have attracted much attention in recent years. An organic light-emitting diode is a device that converts electrical energy into light, and the performance of an organic light-emitting diode is greatly affected by the organic material between the electrodes. Summary of the Invention

[0006] Technical Problem

[0007] One embodiment provides a composition for an organic optoelectronic device that realizes high efficiency and long life for an organic optoelectronic device.

[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, a 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 Z 3 is N or C-La -R a ,

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

[0017] X 1 is O or S,

[0018] L a and L 1 to L 3 each independently is a single bond, a substituted or unsubstituted C6 - C20 arylene, a substituted or unsubstituted C2 - C20 heterocyclic group, or a combination thereof,

[0019] Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C2 - C30 heterocyclic group, or a combination thereof,

[0020] R a and R 1 each independently is hydrogen, deuterium, a substituted or unsubstituted C1 - C30 alkyl, a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C2 - C30 heterocyclic group, a substituted or unsubstituted silyl, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof,

[0021] m1 is one of the integers from 1 to 3,

[0022] Ring A is any one of Chemical Formulas I - 1 to Chemical Formula I - 14,

[0023]

[0024]

[0025] In Chemical Formulas I - 1 to Chemical Formula I - 14, X 2 is O or S,

[0026] R 2 to R 14 each independently is hydrogen, deuterium, a substituted or unsubstituted C1 - C30 alkyl, a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C2 - C30 heterocyclic group, a substituted or unsubstituted silyl, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof,

[0027] m2, m4, m7, m8, m9, m11, m12 and m14 each independently is one of the integers from 1 to 4,

[0028] m3, m5, m6, m10, and m13 are each independently an integer of 1 or 2, and

[0029] * is a connecting point;

[0030] [Chemical Formula 2]

[0031]

[0032] In Chemical Formula 2,

[0033] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heterocyclic group,

[0034] L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 - C20 arylene group,

[0035] R 15 to R 19 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 - C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 - C30 aryl group, or a substituted or unsubstituted C2 - C30 heterocyclic group,

[0036] m15, m18, and m19 are each independently one of the integers from 1 to 4,

[0037] m16 and m17 are each independently one of the integers from 1 to 3, and

[0038] n is one of the integers from 0 to 2;

[0039]

[0040]

[0041] In Chemical Formulas 3 and 4,

[0042] Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heterocyclic group,

[0043] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or C - L b -R b ,

[0044] In a1* to a4* of Chemical Formula 3, two adjacent ones are connected to the * in Chemical Formula 4,

[0045] L b , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0046] R b , R 20 and R 21 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

[0047] m20 and m21 are each independently an integer from 1 to 4;

[0048] [Chemical formula 5]

[0049]

[0050] In Chemical Formula 5,

[0051] R 22 To R 26 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,

[0052] L 7 is a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0053] m22, m23, m25 and m26 are each independently one of integers from 1 to 4, and

[0054] m24 is an integer between 1 and 3.

[0055] 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 composition for an organic optoelectronic device.

[0056] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0057] Beneficial Effects

[0058] An organic optoelectronic device having high efficiency and long lifetime can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0059] Figure 1It is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0060] <Description of Reference Numerals>

[0061] 100: Organic light-emitting diode

[0062] 105: Organic layer

[0063] 110: Cathode

[0064] 120: Anode

[0065] 130: Light-emitting layer

[0066] 140: Hole transport region

[0067] 150: Electron transport region Detailed Embodiments

[0068] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0069] In this specification, when no other definition is provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, halogen, hydroxyl group, amino group, substituted or unsubstituted C1 to C30 amino group, nitro group, substituted or unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, C1 to C10 trifluoroalkyl group, cyano group, or a combination thereof.

[0070] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, cyano group, C1-C30 alkyl group, C1-C10 alkylsilyl group, C6-C30 arylamino group, C6-C30 arylsilyl group, C3-C30 cycloalkyl group, C3-C30 heteroalkyl group, C6-C30 aryl group or C2-C30 heteroaryl group. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, cyano group, C1-C20 alkyl group, C6-C30 arylamino group, C6-C30 aryl group or C2-C30 heteroaryl group. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, cyano group, C1-C5 alkyl group, C6-C20 arylamino group, C6-C18 aryl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group or pyridyl group. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, C6-C20 arylamino group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, fluorenyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group or pyridyl group.

[0071] In this specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0072] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0073] In this specification, when no other definition is provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si in a functional group and the remaining carbon.

[0074] In this specification, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals that form conjugation, such as phenyl group, naphthyl group, etc. Two or more hydrocarbon aromatic moieties can be connected by a σ bond and can be, for example, biphenyl group, terphenyl group, quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl group.

[0075] Aryl may include monocyclic, polycyclic or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0076] In this specification, "heterocyclic group" is a superordinate 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 fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0077] 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 heteroaryl groups are directly connected by a σ bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

[0078] 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed 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 chrysenyl group, 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, but is not limited thereto.

[0079] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl 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 benzothiazinyl 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 dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, or a combination thereof, but is not limited thereto.

[0080] In this specification, the hole property refers to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive property 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.

[0081] In addition, the electron 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, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0082] Hereinafter, a composition for an organic optoelectronic device according to an embodiment is described.

[0083] The composition for an organic optoelectronic device according to an embodiment is a mixture including three types of compounds, specifically, a first compound having an electron property, a second compound having a hole property, and a third compound having buffer characteristics.

[0084] 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 has a hole mobility lower than that of the second compound having a hole property, which reduces the hole injection property and can produce an effect of reducing hole traps.

[0085] In addition, since the electron mobility of the third compound is lower than that of the first compound, and the light-emitting layer region relatively moves toward the hole transport auxiliary layer, exciton quenching at the interface with the electron transport auxiliary layer can be reduced and thus deterioration can be reduced, and accordingly, the lifetime can be increased.

[0086] The first compound having an electron property has a structure in which dibenzofuran (or dibenzothiophene) and derivatives of dibenzofuran (or dibenzothiophene) are substituted by a nitrogen-containing 6-membered ring and represented by Chemical Formula 1.

[0087] [Chemical Formula 1]

[0088]

[0089] In Chemical Formula 1,

[0090] Z 1 to Z 3 is N or C-L a -R a ,

[0091] Z 1 to Z 3At least two of them are N,

[0092] X 1 is O or S,

[0093] L a and L 1 to L 3 each independently is a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof,

[0094] Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof,

[0095] R a and R 1 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof,

[0096] m1 is one of the integers from 1 to 3, and

[0097] Ring A is any one of Chemical Formula I-1 to Chemical Formula I-14,

[0098]

[0099]

[0100] In Chemical Formula I-1 to Chemical Formula I-14,

[0101] X 2 is O or S,

[0102] R 2 to R 14 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof,

[0103] m2, m4, m7, m8, m9, m11, m12 and m14 each independently is one of the integers from 1 to 4,

[0104] m3, m5, m6, m10 and m13 each independently is an integer of 1 or 2, and

[0105] * is a connection point.

[0106] In Chemical Formula 1, when m1 is 2 or greater, R 1 may each be the same as or different from one another.

[0107] In Chemical Formula I-1, when m2 is 2 or greater, R 2 may each be the same as or different from one another.

[0108] In Chemical Formulas I-2 and I-3, when m3 is 2 or greater, R 3 may each be the same as or different from one another.

[0109] In Chemical Formulas I-2 and I-3, when m4 is 2 or greater, R 4 may each be the same as or different from one another.

[0110] In Chemical Formulas I-4 to I-8, when m5 is 2 or greater, R 5 may each be the same as or different from one another.

[0111] In Chemical Formulas I-4 to I-8, when m6 is 2 or greater, R 6 may each be the same as or different from one another.

[0112] In Chemical Formulas I-4 to I-8, when m7 is 2 or greater, R 7 may each be the same as or different from one another.

[0113] In Chemical Formula I-9, when m8 is 2 or greater, R 8 may each be the same as or different from one another.

[0114] In Chemical Formula I-9, when m9 is 2 or greater, R 9 may each be the same as or different from one another.

[0115] In Chemical Formulas I-10 and I-11, when m10 is 2 or greater, R 10 may each be the same as or different from one another.

[0116] In Chemical Formulas I-10 and I-11, when m11 is 2 or greater, R 11 may each be the same as or different from one another.

[0117] In Chemical Formulas I-10 and I-11, when m12 is 2 or greater, R 12 may each be the same as or different from one another.

[0118] In Chemical Formulas I-12 to I-14, when m13 is 2 or greater, R 13 may each be the same as or different from one another.

[0119] In Chemical Formulas I-12 to I-14, when m14 is 2 or greater, R 14 may each be the same as or different from one another.

[0120] For example, in Chemical Formula 1, Z 1 and Z 2 may be N.

[0121] For example, in Chemical Formula 1, Z 1 and Z 3 may be N.

[0122] For example, in Chemical Formula 1, Z 1 to Z 3 may each be N.

[0123] For example, Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-3.

[0124]

[0125]

[0126] In Chemical Formulas 1-1 to 1-3, X 1 , Ar 1 , Ar 2 , R a , R 1 , L a , L 1 to L 3 and m1 are the same as described above.

[0127] In one embodiment, R a may be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0128] In Chemical Formula 1, L 1 to L 3 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0129] In Chemical Formula 1, Ar 1 and Ar 2Each may independently be a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fused carbazolyl group, substituted or unsubstituted fused dibenzofuranyl, substituted or unsubstituted fused dibenzothiophenyl, substituted or unsubstituted fused indolocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl or substituted or unsubstituted benzquinazolinyl.

[0130] For example, in Chemical Formula 1, Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0131] Depending on the specific structures of the dibenzofuran (or dibenzothiophene) and dibenzofuran (or dibenzothiophene) derivatives, Chemical Formula 1 may be represented by any one of, for example, Chemical Formula 1-A to Chemical Formula 1-W.

[0132]

[0133]

[0134]

[0135]

[0136] In Chemical Formula 1-A to Chemical Formula 1-W, Z 1 to Z 3 , Ar 1 , Ar 2 , L 1 to L 3 , R 1 to R 14 , X 1 , X 2 and m1 to m14 are the same as described above.

[0137] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-A, Chemical Formula 1-E, Chemical Formula 1-O and Chemical Formula 1-U.

[0138] For example, Chemical Formula 1-A can be represented by any one of Chemical Formulas 1-A-1 to 1-A-4.

[0139]

[0140]

[0141] In Chemical Formulas 1-A-1 to 1-A-4, Z 1 to Z 3 、Ar 1 、Ar 2 、L 1 to L 3 、R 1 、R 2 、X 1 、m1 and m2 are the same as those above.

[0142] For example, Chemical Formula 1-E can be represented by any one of Chemical Formulas 1-E-1 to 1-E-4.

[0143]

[0144]

[0145] In Chemical Formulas 1-E-1 to 1-E-4, Z 1 to Z 3 、Ar 1 、Ar 2 、L 1 to L 3 、R 1 、R 5 to R 7 、X 1 、m1 and m5 to m7 are the same as those above.

[0146] For example, Chemical Formula 1-O can be represented by any one of Chemical Formulas 1-O-1 to 1-O-4.

[0147]

[0148]

[0149] In Chemical Formulas 1-O-1 to 1-O-4, Z 1 to Z 3 、Ar 1 、Ar 2 、L 1 to L 3 、R 1 、R 10 to R 12 、X 1, m1 and m10 to m12 are the same as described above.

[0150] For example, Chemical Formula 1-U can be represented by any one of Chemical Formulas 1-U-1 to 1-U-4.

[0151]

[0152]

[0153] In Chemical Formulas 1-U-1 to 1-U-4, Z 1 to Z 3 , Ar 1 , Ar 2 , L 1 to L 3 , R 1 , R 13 , R 14 , X 1 , X 2 , m1, m13 and m14 are the same as described above.

[0154] In a specific embodiment of the present invention, the first compound can be represented by any one of the above Chemical Formulas 1-A-3, 1-E-4, 1-O-4 and 1-U-3, and the definition of each substituent is as described above.

[0155] The first compound can be, for example, one selected from the compounds listed in Group 1.

[0156] [Group 1]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162] The second compound having hole properties has a structure in which a C6 to C30 aryl group or a C2 to C30 heterocyclic group in which carbazole or indolocarbazole is substituted or unsubstituted is substituted and is represented, for example, by Chemical Formula 2 or by a combination of Chemical Formulas 3 and 4.

[0163] [Chemical Formula 2]

[0164]

[0165] In Chemical Formula 2,

[0166] Ar 3 and Ar 4 each independently is a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heterocyclic group,

[0167] L 3 and L 4 each independently is a single bond or a substituted or unsubstituted C6 - C20 arylene group,

[0168] R 15 to R 19 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 - C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heterocyclic group,

[0169] m15, m18 and m19 are each independently one of the integers from 1 to 4,

[0170] m16 and m17 are each independently one of the integers from 1 to 3, and

[0171] n is one of the integers from 0 to 2;

[0172]

[0173] In Chemical Formula 3 and Chemical Formula 4,

[0174] Ar 5 and Ar 6 each independently is a substituted or unsubstituted C6 - C30 aryl group or a substituted or unsubstituted C2 - C30 heterocyclic group,

[0175] a1* to a4* in Chemical Formula 3 each independently is a connecting carbon (C) or C - L b -R b ,

[0176] In a1* to a4* of Chemical Formula 3, two adjacent ones are connected to * in Chemical Formula 4,

[0177] L b 、L 5 and L 6 each independently is a single bond or a substituted or unsubstituted C6 - C20 arylene group,

[0178] R b 、R 20 and R 21Each is independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0179] m20 and m21 are each independently one of the integers from 1 to 4.

[0180] In Chemical Formula 2, when m15 is 2 or greater, R 15 may each be the same as or different from one another.

[0181] In Chemical Formula 2, when m16 is 2 or greater, R 16 may each be the same as or different from one another.

[0182] In Chemical Formula 2, when m17 is 2 or greater, R 17 may each be the same as or different from one another.

[0183] In Chemical Formula 2, when m18 is 2 or greater, R 18 may each be the same as or different from one another.

[0184] In Chemical Formula 2, when m19 is 2 or greater, R 19 may each be the same as or different from one another.

[0185] For example, in Chemical Formula 2, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group.

[0186] For example, in Chemical Formula 2, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group, and at least one of Ar 3 and Ar 4 may be a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums or a C2-C20 heterocyclic group substituted or unsubstituted with one or more deuteriums.

[0187] For example, in Chemical Formula 2, R 15 to R 19 may each independently be hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.

[0188] For example, in Chemical Formula 2, R 15 to R19 may each independently be hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group, and R 15 to R 19 at least one of which may be deuterium, a C1-C10 alkyl group substituted or unsubstituted with one or more deuteriums, a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums, or a C2-C20 heterocyclic group substituted or unsubstituted with one or more deuteriums.

[0189] For example, in Chemical Formula 2, Ar 3 and Ar 4 at least one of which may be a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums or a C2-C20 heterocyclic group substituted or unsubstituted with one or more deuteriums, and R 15 to R 19 at least one of which may be deuterium, a C1-C10 alkyl group substituted or unsubstituted with one or more deuteriums, a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums, or a C2-C20 heterocyclic group substituted or unsubstituted with one or more deuteriums.

[0190] As a specific example, in Chemical Formula 2, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0191] As a specific example, in Chemical Formula 2, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, and Ar 3 and Ar 4 at least one of which may be a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted with one or more deuteriums, a dibenzothiophenyl group substituted or unsubstituted with one or more deuteriums, or a carbazolyl group substituted or unsubstituted with one or more deuteriums.

[0192] As a specific example, in Chemical Formula 2, Ar 3 and Ar 4At least one of them may be a C6-C20 aryl group which is substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group which is substituted or unsubstituted with one or more deuteriums, a dibenzothiophenyl group which is substituted or unsubstituted with one or more deuteriums, or a carbazolyl group which is substituted or unsubstituted with one or more deuteriums, and R 15 to R 19 At least one of them may be deuterium, a C1-C10 alkyl group which is substituted or unsubstituted with one or more deuteriums, a C6-C20 aryl group which is substituted or unsubstituted with one or more deuteriums, or a C2-C20 heterocyclic group which is substituted or unsubstituted with one or more deuteriums.

[0193] In Chemical Formulas 3 and 4, when m20 is 2 or greater, R 20 may each be the same as or different from one another.

[0194] In Chemical Formulas 3 and 4, when m21 is 2 or greater, R 21 may each be the same as or different from one another.

[0195] For example, in Chemical Formulas 3 and 4, Ar 5 and Ar 6 may each independently be a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group.

[0196] For example, in Chemical Formulas 3 and 4, Ar 5 and Ar 6 may each independently be a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group, and at least one of Ar 5 and Ar 6 may be a C6-C20 aryl group which is substituted or unsubstituted with one or more deuteriums or a C2-C20 heterocyclic group which is substituted or unsubstituted with one or more deuteriums.

[0197] For example, in Chemical Formulas 3 and 4, R b , R 20 and R 21 may each independently be hydrogen, deuterium, a cyano group, a halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.

[0198] For example, in Chemical Formulas 3 and 4, R b , R 20 and R 21may each independently be hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group, and R b 、R 20 and R 21 at least one of which may be deuterium, a C1-C10 alkyl group substituted or unsubstituted with one or more deuteriums, a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums, or a C2-C20 heterocyclic group substituted or unsubstituted with one or more deuteriums.

[0199] For example, in Chemical Formula 3 and Chemical Formula 4, at least one of Ar 5 and Ar 6 may be a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums or a C2-C20 heterocyclic group substituted or unsubstituted with one or more deuteriums, and at least one of R b 、R 20 and R 21 may be deuterium, a C1-C10 alkyl group substituted or unsubstituted with one or more deuteriums, a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums, or a C2-C20 heterocyclic group substituted or unsubstituted with one or more deuteriums.

[0200] 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-C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0201] 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-C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, and at least one of Ar 5 and Ar 6 may be a C6-C20 aryl group substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group substituted or unsubstituted with one or more deuteriums, a dibenzothiophenyl group substituted or unsubstituted with one or more deuteriums, or a carbazolyl group substituted or unsubstituted with one or more deuteriums.

[0202] As a specific example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6At least one of them can be a C6-C20 aryl group which is substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group which is substituted or unsubstituted with one or more deuteriums, a dibenzothiophenyl group which is substituted or unsubstituted with one or more deuteriums, or a carbazolyl group which is substituted or unsubstituted with one or more deuteriums, and R b 、R 20 and R 21 At least one of them can be deuterium, a C1-C10 alkyl group which is substituted or unsubstituted with one or more deuteriums, a C6-C20 aryl group which is substituted or unsubstituted with one or more deuteriums, or a C2-C20 heterocyclic group which is substituted or unsubstituted with one or more deuteriums.

[0203] As a more specific example, in Chemical Formula 2, Ar 3 and Ar 4 can 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group,

[0204] In Chemical Formula 2, L 3 and L 4 can 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,

[0205] In Chemical Formula 2, R 15 to R 19 can each independently be hydrogen, deuterium, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0206] n can be 0 or 1.

[0207] For example, in Chemical Formula 2, Ar 3 and Ar 4 can 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0208] Ar 3 and Ar 4At least one of them may be a phenyl group which is unsubstituted or substituted with one or more deuteriums, a biphenyl group which is unsubstituted or substituted with one or more deuteriums, a terphenyl group which is unsubstituted or substituted with one or more deuteriums, a naphthyl group which is unsubstituted or substituted with one or more deuteriums, an anthryl group which is unsubstituted or substituted with one or more deuteriums, a phenanthryl group which is unsubstituted or substituted with one or more deuteriums, a terphenylene group which is unsubstituted or substituted with one or more deuteriums, a carbazolyl group which is unsubstituted or substituted with one or more deuteriums, a dibenzothiophenyl group which is unsubstituted or substituted with one or more deuteriums, a dibenzofuranyl group which is unsubstituted or substituted with one or more deuteriums, or a fluorenyl group which is unsubstituted or substituted with one or more deuteriums.

[0209] For example, in Chemical Formula 2, R 15 to R 19 may each independently be hydrogen, deuterium, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0210] R 15 to R 19 at least one of them may be deuterium, a C6-C12 aryl group which is unsubstituted or substituted with one or more deuteriums, a carbazolyl group which is unsubstituted or substituted with one or more deuteriums, a dibenzofuranyl group which is unsubstituted or substituted with one or more deuteriums, or a dibenzothiophenyl group which is unsubstituted or substituted with one or more deuteriums.

[0211] For example, in Chemical Formula 2, at least one of Ar 3 and Ar 4 may be a phenyl group which is unsubstituted or substituted with one or more deuteriums, a biphenyl group which is unsubstituted or substituted with one or more deuteriums, a terphenyl group which is unsubstituted or substituted with one or more deuteriums, a naphthyl group which is unsubstituted or substituted with one or more deuteriums, an anthryl group which is unsubstituted or substituted with one or more deuteriums, a phenanthryl group which is unsubstituted or substituted with one or more deuteriums, a terphenylene group which is unsubstituted or substituted with one or more deuteriums, a carbazolyl group which is unsubstituted or substituted with one or more deuteriums, a dibenzothiophenyl group which is unsubstituted or substituted with one or more deuteriums, a dibenzofuranyl group which is unsubstituted or substituted with one or more deuteriums, or a fluorenyl group which is unsubstituted or substituted with one or more deuteriums, and

[0212] in Chemical Formula 2, at least one of R 15 to R 19 may be deuterium, a C6-C12 aryl group which is unsubstituted or substituted with one or more deuteriums, a carbazolyl group which is unsubstituted or substituted with one or more deuteriums, a dibenzofuranyl group which is unsubstituted or substituted with one or more deuteriums, or a dibenzothiophenyl group which is unsubstituted or substituted with one or more deuteriums.

[0213] As an example, in Chemical Formula 2, "substituted" means that at least one hydrogen is replaced by deuterium, a C1-C4 alkyl group, a C6-C18 aryl group, or a C2-C30 heteroaryl group.

[0214] In a specific embodiment of the present invention, Chemical Formula 2 can be represented by any one of Chemical Formulas 2-1 to 2-15.

[0215]

[0216]

[0217] In Chemical Formulas 2-1 to 2-15, R 15 to R 19 can each independently be hydrogen, deuterium, a substituted or unsubstituted C6-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 can each independently be one of the substituents listed in Group I.

[0218] [Group I]

[0219]

[0220] In Group I,

[0221] R 59 to R 62 each independently are hydrogen, deuterium, a C1-C4 alkyl group, a C6-C18 aryl group, or a C2-C30 heteroaryl group,

[0222] m28 is one of the integers from 1 to 5,

[0223] m29 is one of the integers from 1 to 4,

[0224] m30 is one of the integers from 1 to 3,

[0225] m31 is an integer of 1 or 2, and

[0226] * is a connection point.

[0227] In Group I, when m28 is 2 or greater, R 59 can each be the same as or different from each other.

[0228] In Group I, when m29 is 2 or greater, R 60 can each be the same as or different from each other.

[0229] In Group I, when m30 is 2 or greater, R61 Each may be the same as or different from each other.

[0230] In Group I, when m31 is 2 or greater, R 62 Each may be the same as or different from each other.

[0231] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0232] In addition, in Chemical Formula 2-8, *-L 3 -Ar 3 and *-L 4 -Ar 4 may each independently be selected from Group I and may be any one of, for example, C-1, C-2, C-3, C-4, C-7, C-8, and C-9.

[0233] 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.

[0234]

[0235] In Chemical Formulas 3A to 3E, Ar 5 、Ar 6 、L 5 、L 6 、R 20 and R 21 are the same as those described above,

[0236] L b1 to L b4 are as defined for L 5 and L 6 above, and

[0237] R b1 to R b4 are as defined for R 20 and R 21 above.

[0238] For example, in Chemical 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 terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

[0239] R b1 to R b4 、R 20 and R 21may each 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.

[0240] In a specific embodiment of the present invention, in Chemical Formula 3 and Chemical Formula 4, *-L 5 -Ar 5 and *-L 6 -Ar 6 may each independently be selected from the substituents listed in Group I.

[0241] In one embodiment, R b1 to R b4 , R 20 and R 21 may each independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0242] For example, R b1 to R b4 , R 20 and R 21 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

[0243] In a specific embodiment, R b1 to R b4 , R 20 and R 21 may each independently be hydrogen, deuterium, phenyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl.

[0244] For example, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, and

[0245] Ar 5 and Ar 6At least one of them may be a phenyl group which is substituted or unsubstituted with one or more deuteriums, a biphenyl group which is substituted or unsubstituted with one or more deuteriums, a naphthyl group which is substituted or unsubstituted with one or more deuteriums, a terphenyl group which is substituted or unsubstituted with one or more deuteriums, a carbazolyl group which is substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group which is substituted or unsubstituted with one or more deuteriums, or a dibenzothiophenyl group which is substituted or unsubstituted with one or more deuteriums.

[0246] For example, in Chemical Formulas 3 and 4, R b1 to R b4 , R 20 and R 21 may each independently be hydrogen, deuterium, 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, and

[0247] R b1 to R b4 , R 20 and R 21 at least one of them may be deuterium, a phenyl group which is substituted or unsubstituted with one or more deuteriums, a biphenyl group which is substituted or unsubstituted with one or more deuteriums, a carbazolyl group which is substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group which is substituted or unsubstituted with one or more deuteriums, or a dibenzothiophenyl group which is substituted or unsubstituted with one or more deuteriums.

[0248] For example, in Chemical Formulas 3 and 4, at least one of Ar 5 and Ar 6 may be a phenyl group which is substituted or unsubstituted with one or more deuteriums, a biphenyl group which is substituted or unsubstituted with one or more deuteriums, a naphthyl group which is substituted or unsubstituted with one or more deuteriums, a terphenyl group which is substituted or unsubstituted with one or more deuteriums, a carbazolyl group which is substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group which is substituted or unsubstituted with one or more deuteriums, or a dibenzothiophenyl group which is substituted or unsubstituted with one or more deuteriums, and

[0249] R b1 to R b4 , R 20 and R 21 at least one of them may be deuterium, a phenyl group which is substituted or unsubstituted with one or more deuteriums, a biphenyl group which is substituted or unsubstituted with one or more deuteriums, a carbazolyl group which is substituted or unsubstituted with one or more deuteriums, a dibenzofuranyl group which is substituted or unsubstituted with one or more deuteriums, or a dibenzothiophenyl group which is substituted or unsubstituted with one or more deuteriums.

[0250] In a specific embodiment of the present invention, the second compound may be represented by Chemical Formula 2-8. In Chemical Formula 2-8, Ar 3and Ar 4 may each 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 anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted terphenylene, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted fluorenyl, L 3 and L 4 may each independently be a single bond or a substituted or unsubstituted C6 - C20 arylene, and R 15 to R 19 may each independently be hydrogen, deuterium, cyano, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl.

[0251] In a specific embodiment of the present invention, the second compound may be represented by Chemical Formula 3C, in which L b1 and L b2 may be a single bond, L 5 and L 6 may each independently be a single bond or a substituted or unsubstituted C6 - C12 arylene, R b1 , R b2 , R 20 and R 21 may each independently be hydrogen, deuterium, phenyl, terphenylene, carbazolyl, dibenzofuranyl or dibenzothiophenyl, and Ar 5 and Ar 6 may each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl.

[0252] For example, the second compound may be one of the compounds listed in Group 2, but is not limited thereto.

[0253] [Group 2]

[0254]

[0255]

[0256]

[0257] The third compound having a buffering property has a structure in which terphenylene is substituted by 9 - carbazole and is represented by Chemical Formula 5.

[0258] [Chemical Formula 5]

[0259]

[0260] In Chemical Formula 5,

[0261] R 22 to R 26 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof,

[0262] L 7 is a single bond or a substituted or unsubstituted C6-C20 arylene group,

[0263] m22, m23, m25, and m26 are each independently one of the integers from 1 to 4, and

[0264] m24 is one of the integers from 1 to 3.

[0265] In Chemical Formula 5, when m22 is 2 or greater, R 22 may each be the same as or different from one another.

[0266] In Chemical Formula 5, when m23 is 2 or greater, R 23 may each be the same as or different from one another.

[0267] In Chemical Formula 5, when m24 is 2 or greater, R 24 may each be the same as or different from one another.

[0268] In Chemical Formula 5, when m25 is 2 or greater, R 25 may each be the same as or different from one another.

[0269] In Chemical Formula 5, when m26 is 2 or greater, R 26 may each be the same as or different from one another.

[0270] Specifically, L 7 may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0271] More specifically, L 7 may be a single bond; a substituted or unsubstituted phenylene group, including at least one of meta-phenylene and para-phenylene; a substituted or unsubstituted biphenylene group, including at least one of meta-phenylene and para-phenylene; or a terphenylene group, including at least one of meta-phenylene and para-phenylene.

[0272] For example, L 7 may be a single bond or may be selected from the linking groups listed in Group II.

[0273] [Group II]

[0274]

[0275] In Group II,

[0276] R 55 to R 66 are each independently hydrogen, deuterium, a C1-C10 alkyl group, a substituted or unsubstituted C6-C12 aryl group, a halogen, a cyano group, or a combination thereof, and

[0277] * is a point of attachment.

[0278] For example, it can be represented by any one of Chemical Formulas 5-I to 5-III.

[0279]

[0280] [Chemical Formula 5-III]

[0281]

[0282] In Chemical Formulas 5-I to 5-III, R 22 to R 26 , R 28 and m22 to m26 are the same as above, and

[0283] m32 is one of the integers from 1 to 4.

[0284] For example, the third compound can be represented by Chemical Formula 5-II.

[0285] Specifically, in Chemical Formula 5, R 22 to R 24 can each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0286] Specifically, in Chemical Formula 5, R 25 and R 26 can each independently be hydrogen, deuterium, 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.

[0287] The third compound can be, for example, one selected from the compounds listed in Group 3.

[0288] [Group 3]

[0289]

[0290]

[0291] The first compound includes a nitrogen-containing six-membered ring, which has high electron-transporting properties and can thus stably and efficiently transport electrons to reduce the driving voltage of the device, improve the current efficiency, and achieve long-life characteristics.

[0292] The second compound has a structure including carbazole having a high HOMO energy level and can thus effectively inject and transport holes, thereby contributing to the improvement of device characteristics.

[0293] The third compound has a wide HOMO-LUMO bandgap, thereby controlling the hole and electron mobility ratios of the first and second compounds, and can thus prevent hole trapping and exciton quenching through the relative movement of the light-emitting layer region, which contributes to the improvement of the device's life characteristics.

[0294] Compared with two-host compositions (such as a composition containing the first and second compounds or a composition containing the first and third compounds), the three-host composition containing the first, second, and third compounds can achieve an optimal balance by more finely adjusting the electron / hole characteristics in the device stack, and can greatly improve the device characteristics due to the proper balance of charges.

[0295] Furthermore, compared with other three-host compositions having different combinations, this three-host composition can further improve the life and efficiency characteristics by optimally adjusting the balance of electron / hole characteristics.

[0296] 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.

[0297] Such a mixed composition of the first, second, and third compounds may be included, for example, as a phosphorescent host in the light-emitting layer of an organic light-emitting diode, which will be described later.

[0298] In the composition for an organic optoelectronic device, based on the total weight of the first, second, and third compounds, the first compound may be included in an amount of about 20 wt% to 50 wt%; based on the total weight of the first, second, and third compounds, the second compound may be included in an amount of about 40 wt% to 60 wt%; and based on the total weight of the first, second, and third compounds, the third compound may be included in an amount of about 10 wt% to 30 wt%.

[0299] Within the above ranges, for example, 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 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%; and 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 third compound for an organic optoelectronic device may be included in an amount of about 10 wt% to 25 wt%.

[0300] In addition, as a specific example, based on the total weight of the first compound, the second compound, and the third compound, the first compound may be included in an amount of about 30 wt% to 40 wt%; based on the total weight of the first compound, the second compound, and the third compound, the second compound may be included in an amount of about 45 wt% to 55 wt%; and based on the total weight of the first compound, the second compound, and the third compound, the third compound may be included in an amount of about 10 wt% to 20 wt%.

[0301] As a more specific example, the composition for an organic optoelectronic device may include the first compound:the second compound:the third compound in a weight ratio of about 35:55:10 or about 32:48:20. Within the above ranges, 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 lifespan of the device.

[0302] In addition to the first compound, the second compound, and the third compound, the composition for an organic optoelectronic device may further include one or more compounds.

[0303] 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.

[0304] The dopant is a material that is mixed in a small amount with the composition containing the first compound, the second compound, and the third compound to cause luminescence, and may generally be a material such as a metal complex that emits light by being excited to a triplet state or more states multiple times. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0305] Examples of the dopant may be phosphorescent dopants, and examples of the phosphorescent dopants may be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[0306] [Chemical Formula Z]

[0307] L 9 MX 3

[0308] In Chemical Formula Z, M is a metal, and L 9 and X 3 are the same or different and are ligands that form a complex with M.

[0309] M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 9 and X 3 may be, for example, bidentate ligands.

[0310] Examples of the ligands represented by L 9 and X 3 may be selected from the chemical formulas listed in Group A, but are not limited thereto.

[0311] [Group A]

[0312]

[0313]

[0314] In Group A,

[0315] R 300 to R 302 are each independently hydrogen, deuterium, a C1-C30 alkyl group that is substituted or unsubstituted with a halogen, a C6-C30 aryl group that is substituted or unsubstituted with a C1-C30 alkyl group, or a halogen, and

[0316] R 303 to R 324Each independently is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 heteroaryl group, a substituted or unsubstituted C1-C30 amino group, a substituted or unsubstituted C6-C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.

[0317] In one embodiment, the dopant may be an iridium complex and may be represented by Chemical Formula 6-1 or Chemical Formula 6-2.

[0318] [Chemical Formula 6-1]

[0319]

[0320] In Chemical Formula 6-1,

[0321] R 101 to R 116 Each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 ,

[0322] R 132 to R 134 Each independently is a substituted or unsubstituted C1-C6 alkyl group,

[0323] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula V-1,

[0324] L 100 is a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through a lone pair of electrons of a carbon or heteroatom, and

[0325] m21 and m22 each independently is any one of integers from 0 to 3, and m21 + m22 is any one of integers from 1 to 3,

[0326] [Chemical Formula V-1]

[0327]

[0328] In Chemical Formula V-1,

[0329] R135 to R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 , and

[0330] * represents the moiety attached to the carbon atom.

[0331] [Chemical Formula 6-2]

[0332]

[0333] In Chemical Formula 6-2,

[0334] R 101 to R 117 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 133 R 134 R 135 ,

[0335] R 133 to R 135 are each independently a substituted or unsubstituted C1-C6 alkyl group,

[0336] L 100 is a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through a lone pair of electrons of a carbon or heteroatom, and

[0337] n1 and n2 are each independently any one of the integers from 0 to 3, and n1 + n2 is any one of the integers from 1 to 3.

[0338] In another embodiment, the dopant may be a platinum complex, for example, a platinum complex represented by Chemical Formula Z-1.

[0339] [Chemical Formula Z-1]

[0340]

[0341] In Chemical Formula Z-1, rings A, B, C, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0342] R A 、R B 、R C and R D are each independently monosubstituted, disubstituted, trisubstituted, tetrasubstituted, or unsubstituted;

[0343] L B 、L C and LD each independently is a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR', SiRR', GeRR', or a combination thereof,

[0344] when nA is 1, L E can be a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR', SiRR', GeRR', or a combination thereof; and when nA is 0, L E does not exist;

[0345] R A 、R B 、R C 、R D 、R and R' each independently is hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphino, or a combination thereof; any adjacent R A 、R B 、R C 、R D 、R and R' are optionally connected to each other to provide a ring; X B 、X C 、X D and X E each independently is selected from carbon and nitrogen; and Q 1 、Q 2 、Q 3 and Q 4 each represents oxygen or a direct bond.

[0346] The platinum complex can be represented, for example, by Chemical Formula 7-1 or Chemical Formula 7-2.

[0347] [Chemical Formula 7-1]

[0348]

[0349] [Chemical Formula 7-2]

[0350]

[0351] In Chemical Formula 7-1 and Chemical Formula 7-2,

[0352] X 100 is selected from O, S, and NR 132 ,

[0353] R 118 to R 132Each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 133 R 134 R 135 ,

[0354] R 133 to R 135 Each independently is a substituted or unsubstituted C1-C6 alkyl group,

[0355] R 118 to R 132 At least one of 133 R 134 R 135 or tert-butyl, and

[0356] R 133 to R 135 Each independently is a substituted or unsubstituted C1-C6 alkyl group.

[0357] A composition for an organic optoelectronic device can be formed by a dry film deposition method (such as chemical vapor deposition).

[0358] Hereinafter, an organic optoelectronic device using the above composition for an organic optoelectronic device is described.

[0359] An organic optoelectronic device can be a suitable device that converts electrical energy into light energy and vice versa, for example, an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, or an organic photoreceptor drum.

[0360] Herein, an organic light-emitting diode as an example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0361] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to one embodiment.

[0362] Referring 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.

[0363] The anode 120 can be made of a conductor having a large work function to assist hole injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 can be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc. or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylenedioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but not limited thereto.

[0364] The cathode 110 can be made of a conductor having a small work function to assist electron injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 can 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 not limited thereto.

[0365] The organic layer 105 can contain the above compounds for organic optoelectronic devices or compositions for organic optoelectronic devices.

[0366] The organic layer 105 can include a light-emitting layer 130, and the light-emitting layer 130 can contain the above compounds for organic optoelectronic devices or compositions for organic optoelectronic devices.

[0367] The composition for organic optoelectronic devices further containing a dopant can be, for example, a greenlight emitting composition.

[0368] The light-emitting layer 130 can contain, for example, the above compounds for organic optoelectronic devices or compositions for organic optoelectronic devices as a phosphorescent host.

[0369] In addition to the light-emitting layer, the organic layer can further include a charge transport region.

[0370] The charge transport region can be, for example, a hole transport region 140.

[0371] The hole transport region 140 can further increase the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0372] 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 hole transport layer and the hole transport auxiliary layer may include at least one of the compounds in Group B.

[0373] [Group B]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380] (Dn refers to the number of deuterium substitutions and represents a structure substituted with one or more deuteriums).

[0381] In the hole transport region 140, in addition to the above compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having similar structures can also be used.

[0382] In addition, the charge transport region may be, for example, the electron transport region 150.

[0383] The electron transport region 150 can further increase the electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0384] 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 electron transport layer and the electron transport auxiliary layer may include at least one of the compounds in Group C.

[0385] [Group C]

[0386]

[0387]

[0388]

[0389]

[0390] One embodiment may be an organic light-emitting diode including a light-emitting layer as an organic layer.

[0391] Another embodiment may be an organic light-emitting diode including a light-emitting layer and a hole transport region as organic layers.

[0392] Another embodiment may be an organic light-emitting diode including a light-emitting layer and an electron transport region as organic layers.

[0393] As Figure 1 shown, 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 organic layers 105 in addition to a light-emitting layer 130.

[0394] On the other hand, in addition to the light-emitting layer, the organic light-emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as organic layers.

[0395] The organic light-emitting diode 100 can be manufactured by forming an anode or a cathode on a substrate, then forming the organic layers by a dry film method (such as vacuum deposition, sputtering, plasma electroplating, and ion electroplating), and forming a cathode or an anode thereon.

[0396] The above organic light-emitting diode can be applied to an organic light-emitting display device.

[0397] Mode of the Invention

[0398] Hereinafter, the embodiments will be described in more detail with reference to examples. However, these examples are exemplary, and the scope of the claims is not limited thereto.

[0399] (Synthesis of the First Compound)

[0400] Synthesis Example 1: Synthesis of Compound 1-1

[0401] [Reaction Scheme 1]

[0402]

[0403] Under a nitrogen stream, in a round-bottom flask, 26.50 g (96.67 mmol) of 3-p-terphenylboronic acid, 36.32 g (101.51 mmol) of 2-chloro-4-(3-dibenzofuranyl)-6-phenyl-1,3,5-triazine, 33.40 g (241.68 mmol) of K2CO3 and 3.35 g (2.9 mmol) of Pd(PPh3)4 were suspended in 260 ml of THF and 130 ml of distilled water, and then stirred under reflux for 8 hours. After the reaction was completed, the resulting mixture was concentrated and dissolved in toluene. The organic solvent was filtered through a silica gel pad and then removed under reduced pressure. The solid was recrystallized from toluene to obtain 44.5 g (83%) of Compound 1-1.

[0404] (Synthesis of the second compound)

[0405] Synthesis Example 2: Synthesis of Compound 2-2

[0406] The compound was synthesized in the same manner as described in KR10-2017-0037277A.

[0407] Synthesis Example 3: Synthesis of Compound 2-15

[0408] [Reaction Scheme 2]

[0409]

[0410] Step 1: Synthesis of Intermediate 2-15-1

[0411] 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. The organic layer was purified by a silica gel column (hexane / dichloromethane = 9:1 (v / v)) to obtain 14.70 g (yield: 87%) of Intermediate 2-15-1.

[0412] Step 2: Synthesis of Intermediate 2-15-2

[0413] In a round-bottom flask, 15.50 g (38.92 mmol) of synthetic intermediate 2-15-1, 7.15 g (42.81 mmol) of (2-nitrophenyl)-boronic acid, 16.14 g (116.75 mmol) of potassium carbonate and 1.35 g (1.17 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) were suspended in 150 ml of toluene and 70 ml of distilled water, and then stirred under reflux for 12 hours. Subsequently, the organic layer thus obtained was extracted with dichloromethane and distilled water, and then filtered through silica gel. After removing the organic solution thus obtained, the solid produced therein was recrystallized with dichloromethane and n-hexane to obtain 13.72 g (yield: 80%) of intermediate 2-15-2.

[0414] Step 3: Synthesis of Intermediate 2-15-3

[0415] 22.46 g (51.00 mmol) of synthetic intermediate 2-15-2 and 52.8 ml of triethyl phosphite were added to a round-bottom flask, and after replacing the inside with nitrogen, it was stirred at 160 °C for 12 hours. When the reaction was completed, 3 L of MeOH was added thereto, and then filtered to evaporate the filtrate. Then, it was purified by column chromatography (hexane) to obtain 10.42 g (yield: 50%) of intermediate 2-15-3.

[0416] Step 4: Synthesis of Compound 2-15

[0417] Compound 2-15 (yield: 60%) was synthesized in the same manner as in Step 1 of Synthesis Example 3, except that intermediate 2-15-3 and 3-iodo-1,1'-biphenyl were used.

[0418] (LC / MS theoretical value: 560.23 g / mol, measured value: 561.57 g / mol)

[0419] Synthesis Example 4: Synthesis of Compound 2-13

[0420] [Reaction Formula 3]

[0421]

[0422] Step 1: Synthesis of Intermediate 2-13-1

[0423] In a round-bottom flask, 18.23 g (40.94 mmol) of 2-[9-([1,1'-biphenyl]-4-yl)-9H-carbazol-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 mmol) 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 under reflux. Subsequently, the resulting organic layer was extracted with dichloromethane and distilled water, and then filtered through silica gel. After removing the organic solution, the resulting solid was recrystallized with dichloromethane and n-hexane to obtain 18.05 g (yield: 91%) of intermediate 2-13-1.

[0424] Step 2: Synthesis of Compound 2-13

[0425] In a round-bottom flask, 13.29 g (27.42 mmol) of intermediate 2-13-1, 6.39 g (27.42 mmol) of 4-bromo-biphenyl, 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 the organic layer. The organic layer was purified by a silica gel column (hexane / dichloromethane = 9:1 (v / v)) to obtain 15.37 g (yield: 88%) of compound 2-13.

[0426] LC-Mass (LC-MS) (theoretical value: 636.26 g / mol, measured value: M+ = 637.40 g / mol)

[0427] (Synthesis of the third compound)

[0428] Synthesis Example 5: Synthesis of Compound 3-6

[0429] [Reaction formula 4]

[0430]

[0431] Step 1: Synthesis of Intermediate 3-6-1

[0432] Intermediate 3-6-1 was synthesized in the same manner as described in KR2014135532, except that 2,7-dibromoterphenyl (888041-37-0) was used.

[0433] Step 2: Synthesis of Compound 3-6

[0434] 8.85 g (23.10 mmol) of 1 equivalent of Intermediate 3-6-1, 7.44 g (23.56 mmol) of 1.1 equivalents of (3-(9H-carbazol-9-yl)phenyl)boronic acid (cas: 864377-33-3), 0.8 g (0.69 mmol) of Pd(PPh3)4 and 6.39 g (46.2 mmol) of K2CO3 were suspended in 100 ml of THF and 50 ml of distilled water, and then stirred under reflux for 12 hours. When the reaction was completed, after cooling the resulting product to room temperature, the solid thus formed was filtered and then washed with distilled water and acetone. The solid was dissolved by heating in 200 ml of dichlorobenzene, filtered through silica gel, and then recrystallized in 150 ml of dichlorobenzene to synthesize Compound 3-6 (10.1 g, white powder) with a yield of 80%.

[0435] LC-MS (theoretical value: 545.21 g / mol, measured value: M+ = 546.27 g / mol)

[0436] Synthesis Example 6: Synthesis of Compound 3-7

[0437] [Reaction Scheme 5]

[0438]

[0439] Using the same method as in Step 2 of Synthesis Example 4, using 1 equivalent of 2-(3-chlorophenyl)-terphenyl (cas: 1384206-44-3) and 2-phenyl-9H-carbazole (cas: 88590-00-5), Compound 3-7 was synthesized with a yield of 85%.

[0440] LC-MS (theoretical value: 545.21 g / mol, measured value: M+ = 546.24 g / mol)

[0441] Compound C1

[0442]

[0443] (Synthesis of Dopant)

[0444] Synthesis Example 7: Synthesis of Dopant Compound PtGD

[0445] [PtGD]

[0446]

[0447] It was synthesized using the same method described in KR1999337.

[0448] (Fabrication of Organic Light-Emitting Diode)

[0449] Example 1

[0450] Wash the glass substrate coated with an ITO (indium tin oxide) film with distilled water. After washing with distilled water, ultrasonically wash the glass substrate with a solvent such as isopropanol, acetone, methanol, etc. and dry it, then transfer it to a plasma cleaner, clean it with oxygen plasma for 10 minutes, and transfer it to a vacuum depositor. Use this prepared ITO transparent electrode as the anode, and vacuum deposit Compound A doped with 3% NDP-9 (Novaled GmbH) on the ITO substrate to form a thick hole injection layer, and deposit Compound A on the hole injection layer to a thickness to form a hole transport layer. Deposit Compound B on the hole transport layer to a thickness to form a hole transport auxiliary layer. On the hole transport auxiliary layer, use Compound 1-1, Compound 2-2, and Compound 3-7 as hosts simultaneously, and dope 15 wt% of PtGD as a dopant, and form a thick light-emitting layer by vacuum deposition. Here, Compound 1-1, Compound 2-2, and Compound 3-7 are used in a weight ratio of 30:55:15, and the ratios are described separately for the following examples and comparative examples. Then, deposit Compound C on the light-emitting layer to a thickness to form an electron transport auxiliary layer, and simultaneously vacuum deposit Compound D and LiQ in a weight ratio of 1:1 to form a thickness of the electron transport layer. Manufacture an organic light-emitting diode by sequentially vacuum depositing LiQ of and

[0451] ITO / Compound A (doped with 3% NDP-9, ) / Compound A / Compound B / EML [host (Compound 1-1:Compound 2-2:Compound 3-7 = 30:55:15, 85 wt%), PtGD (15 wt%)] / Compound C / Compound D:LiQ / LiQ / Al

[0452] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0453] Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0454] Compound C: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0455] Compound D: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0456] Examples 2 and 3

[0457] Each organic light-emitting diode was fabricated in the same manner as in Example 1, except that the composition was changed to the hosts shown in Tables 1 to 3.

[0458] Comparative Examples 1 to 7

[0459] Each organic light-emitting diode was fabricated in the same manner as in Example 1, except that the composition was changed to the hosts shown in Tables 1 to 3.

[0460] Evaluation

[0461] The organic light-emitting diodes according to Examples 1 to 3 and Comparative Examples 1 to 7 were measured for efficiency and lifetime.

[0462] The measurements were performed by the following methods, and the results are shown in Tables 1 to 3.

[0463] (1) Lifetime measurement

[0464] The lifetime was obtained by measuring the time when the current efficiency (cd / A) decreased to 95% while maintaining a brightness (cd / m 2 ) of 24,000 cd / m 2 . The results are shown as relative lifetime ratios based on the lifetimes of Comparative Examples 1, 4, and 6.

[0465] (2) Measurement of the change in current density according to voltage change

[0466] 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 the result.

[0467] (3) Measurement of the change in brightness according to voltage change

[0468] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, the luminance was measured by using a luminance meter (Minolta Cs-1000A).

[0469] (4) Measure the current efficiency

[0470] Calculate the current efficiency (cd / A) for the required luminance of 9000 nit by using the luminance, current density, and voltage measured in (1) and (2). The current efficiency (cd / A) is shown as the relative efficiency ratio based on the current efficiencies of Comparative Examples 1, 4, and 6.

[0471] [Table 1]

[0472]

[0473] [Table 2]

[0474]

[0475] [Table 3]

[0476]

[0477] Referring to Tables 1 to 3, it was confirmed that the organic light-emitting diodes of Examples 1 to 3 exhibited significantly improved lifetimes and maintained comparable or higher efficiencies compared to the organic light-emitting diodes of Comparative Examples 1 to 7.

[0478] Although the present invention has been described in connection with exemplary embodiments that are presently considered to be practical, it is to be understood that the invention is not limited to the disclosed embodiments. 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; a second compound; and a third compound, Among them, 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: [Chemical Formula 1] In Chemical Formula 1, Z 1 from Z to 3 is N or C-L a -R a , Z 1 to Z 3 at least two of which are N, X 1 is O or S, L a and L 1 to L 3 each independently is a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C20 heterocyclic group, or a combination thereof Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof, R a and R 1 each independently is hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heterocyclic group, substituted or unsubstituted silyl, substituted or unsubstituted amino group, halogen, cyano or a combination thereof, m1 is one of the integers from 1 to 3, and ring A is any one of Chemical Formulas I-1 to I-14, in Chemical Formulas I-1 to I-14, X 2 is O or S, R 2 to R 14 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof m2, m4, m7, m8, m9, m11, m12 and m14 are each independently one of the integers from 1 to 4, m3, m5, m6, m10 and m13 are each independently an integer of 1 or 2, and * is a connection point; [Chemical Formula 2] In Chemical Formula 2, Ar 3 and Ar 4 each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, L 3 and L 4 each independently is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 15 to R 19 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, m15, m18 and m19 are each independently one of the integers from 1 to 4, m16 and m17 are each independently one of the integers from 1 to 3, and n is one of the integers from 0 to 2; in Chemical Formulas 3 and 4, Ar 5 and Ar 6 each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, Each of a1* to a4* in Chemical Formula 3 is independently a linking carbon (C) or C-L b -R b In a1* to a4* of Chemical Formula 3, two adjacent ones are linked to * in Chemical Formula 4, L b 、L 5 and L 6 Each of L and L is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R b , R 20 and R 21 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 m20 and m21 are each independently one of the integers from 1 to 4; [Chemical Formula 5] In Chemical Formula 5, R 22 to R 26 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof, L 7 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, m22, m23, m25 and m26 are each independently one of the integers from 1 to 4, and m24 is one of the 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 Formulas 1-A, 1-E, 1-O and 1-U: in Chemical Formulas 1-A, 1-E, 1-O and 1-U, Z 1 to Z 3 、Ar 1 、Ar 2 、L 1 to L 3 、R 1 、R 2 、R 5 to R 7 、R 10 to R 14 、X 1 、X 2 The definitions of m1, m2, m5 to m7 and m10 to m14 are the same as those in claim 1.

3. The composition for an organic optoelectronic device according to claim 1, wherein the first compound is represented by any one of Chemical Formulas 1-A-3, 1-E-4, 1-O-4 and 1-U-3: in Chemical Formulas 1-A-3, 1-E-4, 1-O-4 and 1-U-3, Z 1 to Z 3 、Ar 1 、Ar 2 、L 1 to L 3 、R 1 、R 2 、R 5 to R 7 、R 10 to R 14 、X 1 、X 2 、m1, m2, m5 to m7, and m10 to m14 are the same as those in claim 1.

4. The composition for an organic optoelectronic device according to claim 1, wherein the second compound is represented by any one of Chemical Formulas 2-6, 2-8 and 3C: [Chemical Formula 3C] in Chemical Formulas 2-6, 2-8 and 3C, L 3 to L 6 、Ar 3 to Ar 6 、R 15 to R 18 、R 20 、R 21 and m15 to m18, m20 and m21 are the same as those in claim 1, L b1 and L b2 is the same as the definition of L in claim 1, and b is identical, and R b1 and R b2 is the same as the definition of R in claim 1 b .

5. 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, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene.

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

7. The composition for an organic optoelectronic device according to claim 1, wherein the third compound is represented by any one of Chemical Formulas 5-I to 5-III: [Chemical Formula 5-III] In Chemical Formulas 5-I to 5-III, R 22 to R 26 and m22 to m26 are the same as those in Claim 1, R 28 is the same as the definition of R in claim 1, and 22 to R 26 and m32 is one of the integers from 1 to 4.

8. The composition for an organic optoelectronic device according to claim 1, wherein In Chemical Formula 5, R 22 to R 24 are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

9. The composition for an organic optoelectronic device according to claim 1, wherein In Chemical Formula 5, R 25 and R 26 are each independently hydrogen, deuterium, 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.

10. The composition for an organic optoelectronic device according to claim 1, wherein the first compound is represented by Chemical Formula 1-A, and 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] In Chemical Formula 1-A, Z 1 to Z 3 、Ar 1 、Ar 2 、L 1 to L 3 、R 1 、R 2 、X 1 、m1 and m2 are the same as those in Claim 1; [Chemical Formula 3C] In Chemical Formulas 2-6, 2-8, and 3C, L 3 to L 6 , Ar 3 to Ar 6 , R 15 to R 18 , R 20 , R 21 , the definitions of m15 to m18, m20, and m21 are the same as those in Claim 1; [Chemical Formula 5-II] In Chemical Formula 5-II, R 22 to R 26 and m22 to m26 are the same as those in claim 1, R 28 is the same as the definition of R in claim 1, and 22 to R 26 and m32 is one of the integers from 1 to 4.

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, Among them, wherein the organic layer contains the composition for an organic optoelectronic device according to any one of Claims 1 to 10.

12. The organic optoelectronic device according to Claim 11, wherein the organic layer includes a light-emitting layer, and the light-emitting layer contains the composition for an organic optoelectronic device.

13. The organic optoelectronic device according to Claim 12, wherein each of the first compound, the second compound, and the third compound is included as a phosphorescent host of the light-emitting layer.

14. The organic optoelectronic device according to Claim 13, wherein the first compound is included in an amount of 20 wt% to 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 40 wt% to 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 10 wt% to 30 wt% based on the total weight of the first compound, the second compound, and the third compound.

15. The organic optoelectronic device according to Claim 12, wherein the composition for an organic optoelectronic device further contains a dopant.

16. The organic optoelectronic device according to Claim 15, wherein the composition for an organic optoelectronic device is a green light-emitting composition.

17. A display device, comprising the organic optoelectronic device according to Claim 11.

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