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

Abstract

The present application relates to a composition for an organic optoelectronic device, and an organic optoelectronic device and a display device each comprising the same, the composition for an organic optoelectronic device comprising a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2. Details of Chemical Formula 1 and Chemical Formula 2 are the same as those described in the specification.

Description

Technical Field

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

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

[0003] According to the operating principle, organic optoelectronic devices can be roughly divided into two types. 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 supplying voltage or current to the electrodes.

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

[0005] Among these examples, due to the increasing demand for flat panel displays, organic light-emitting diodes (OLEDs) have been attracting 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 materials between the electrodes. Summary of the Invention

[0006] Technical Challenges

[0007] One embodiment provides a composition for an organic optoelectronic device, and the composition can achieve an organic optoelectronic device with high efficiency and long life.

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

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

[0010] Means for Solving the Problems

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

[0012] [Chemical Formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] Z 1 to Z 3 each independently is N or C-R a ,

[0016] Z 1 to Z 3 at least two of which are N,

[0017] L 1 and L 2 each independently is a single bond or a substituted or unsubstituted C6-C20 arylene group,

[0018] Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group,

[0019] Ar 3 is a substituted or unsubstituted C6-C20 aryl group,

[0020] R 1 and R 2 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group or a combination thereof,

[0021] m1 is an integer from 1 to 3,

[0022] m2 is an integer from 1 to 4, and

[0023] R a and R 3 to R 10 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group or a combination thereof;

[0024] [Chemical Formula 2]

[0025]

[0026] wherein, in Chemical Formula 2,

[0027] X 1 is O or S,

[0028] Ar 4 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group or a combination thereof,

[0029] R 11 to R 14Each 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.

[0030] R 15 to R 17 Each independently is hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0031] m4, m5, m7, and m8 are each independently an integer from 1 to 3, and

[0032] m3, m6, and m9 are each independently an integer from 1 to 4.

[0033] According to another embodiment, an organic optoelectronic device includes an anode and a cathode facing each other and at least one organic layer located between the anode and the cathode, wherein the organic layer contains the composition for the organic optoelectronic device.

[0034] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0035] Advantages of the Invention

[0036] An organic optoelectronic device with high efficiency, long lifespan, and low drive voltage can be implemented. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0038] <Description of the Reference Numerals>

[0039] 100: Organic light-emitting diode

[0040] 105: Organic layer

[0041] 110: Cathode

[0042] 120: Anode

[0043] 130: Light-emitting layer

[0044] 140: Hole transport region

[0045] 150: Electron transport region DETAILED DESCRIPTION

[0046] Hereinafter, embodiments of the present invention will be described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0047] In this specification, unless otherwise defined, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a halogen, a hydroxyl group, an amino group, a substituted or unsubstituted C1-C30 amino group, a nitro group, a substituted or unsubstituted C1-C40 silyl group, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, a C1-C20 alkoxy group, a C1-C10 trifluoroalkyl group, or a combination thereof.

[0048] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, a cyano group, a C1-C30 alkyl group, a C1-C10 alkylsilyl group, a C6-C30 arylamino group, a C6-C30 arylsilyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C6-C30 aryl group, or a 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 deuterium, a cyano group, a C1-C20 alkyl group, a C6-C30 arylamino group, a C6-C3 aryl group, or a 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 deuterium, a cyano group, a C1-C5 alkyl group, a C6-C20 arylamino group, a C6-C18 aryl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, or a 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 deuterium, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, a C6-C20 arylamino group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a triphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, or a pyridyl group.

[0049] In this specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0050] In this specification, "deuterium substitution (-D)" may include "tritium substitution (-T)".

[0051] In this specification, unless otherwise defined, "hetero" means that a functional group includes one to three heteroatoms selected from N, O, S, P, and Si and the rest are carbon.

[0052] As used herein, "aryl" refers to a group that includes at least one hydrocarbon aromatic moiety, and may include groups in which all elements of the hydrocarbon aromatic moiety have p-orbitals that form a conjugate (e.g., phenyl, naphthyl, and the like), groups in which two or more hydrocarbon aromatic moieties may be linked by a σ bond (e.g., biphenyl, terphenyl, quaterphenyl, and the like), and groups in which two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring (e.g., fluorenyl, and the like).

[0053] An aryl may include monocyclic, polycyclic, or fused polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0054] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P, and Si to replace carbon (C) in a cyclic compound, such as an aryl, cycloalkyl, its fused ring, 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.

[0055] For example, "heteroaryl" may refer to an aryl that includes at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryls are directly linked by a σ bond, or when a heteroaryl includes two or more rings, the two or more rings may be fused. When the heteroaryl is a fused ring, each ring may include one to three heteroatoms.

[0056] More specifically, the substituted or unsubstituted C6-C30 aryl may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted fused tetraphenyl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted group, a substituted or unsubstituted benzotriphenylenyl, a substituted or unsubstituted perylenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indenyl, or a combination thereof, but is not limited thereto.

[0057] 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 or a substituted or unsubstituted dibenzothienyl group or a combination thereof, but not limited thereto.

[0058] In this specification, the hole property refers to the ability to donate electrons to form holes when an electric field is applied, and due to the conductive property according to the energy level of the highest occupied molecular orbital (HOMO), the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0059] 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 energy level of the lowest unoccupied molecular orbital (LUMO), the electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0060] Hereinafter, a composition for an organic optoelectronic device according to an embodiment will be described.

[0061] The composition for an organic optoelectronic device according to an embodiment includes a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2.

[0062] The first compound may be represented by Chemical Formula 1.

[0063] [Chemical Formula 1]

[0064]

[0065] In Chemical Formula 1,

[0066] Z 1 to Z 3 are each independently N or C-R a ,

[0067] Z 1 to Z 3 at least two of which are N,

[0068] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6-C20 arylene group,

[0069] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group,

[0070] Ar 3 is a substituted or unsubstituted C6-C20 aryl group,

[0071] R 1 and R 2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a combination thereof,

[0072] m1 is an integer from 1 to 3,

[0073] m2 is an integer from 1 to 4, and

[0074] R a and R 3 to R 10 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof.

[0075] The first compound represented by Chemical Formula 1 has a structure in which carbazole is a basic skeleton and at least one nitrogen-containing ring (a 6-membered nitrogen-containing ring) and 9-carbazole is substituted at the 1st to 8th positions of carbazole.

[0076] The compound contains at least one nitrogen-containing ring, and thus, when an electric field is applied to the compound, the compound may have a structure that easily accepts electrons, and thus the driving voltage of an organic optoelectronic device manufactured using the compound is reduced.

[0077] In addition, the first compound can form a bipolar structure by including carbazole which is prone to receiving holes, so as to properly balance the flow of holes and electrons, thereby improving the efficiency of the organic optoelectronic device containing the compound.

[0078] Specifically, by connecting to a nitrogen-containing six-membered ring in the 1st to 8th directions of carbazole, the LUMO electron cloud expands from the nitrogen-containing six-membered ring to the carbazole linker, thereby enhancing the electron transport ability, and the additional carbazole substitution in the 9th direction (N direction) can separate the HOMO electron cloud and enhance the hole characteristics. Therefore, by separating the electron cloud between HOMO and LUMO into a hole transport part and an electron transport part, the efficiency and lifespan of the organic light-emitting diode containing it can be further improved.

[0079] In Chemical Formula 1, when m1 is greater than or equal to 2, each R 1 can be the same as or different from each other.

[0080] In Chemical Formula 1, when m2 is greater than or equal to 2, each R 2 can be the same as or different from each other.

[0081] For example, Chemical Formula 1 can be represented by Chemical Formula 1A or Chemical Formula 1B.

[0082] [Chemical Formula 1A]

[0083]

[0084] [Chemical Formula 1B]

[0085]

[0086] In Chemical Formula 1A and Chemical Formula 1B,

[0087] Z 1 to Z 3 、L 1 、L 2 、Ar 1 to Ar 3 、R 1 to R 10 、m1 and m2 are the same as those above,

[0088] m1' is an integer of 1 or 2, and

[0089] m2' is an integer from 1 to 3.

[0090] As a specific example, Chemical Formula 1A can be represented by Chemical Formulas 1A-1 to 1A-4.

[0091] [Chemical Formula 1A-1]

[0092]

[0093] [Chemical Formula 1A-2]

[0094]

[0095] [Chemical Formula 1A-3]

[0096]

[0097] [Chemical Formula 1A-4]

[0098]

[0099] In Chemical Formulas 1A-1 to 1A-4,

[0100] Z 1 to Z 3 、L 1 、L 2 、Ar 1 to Ar 3 、R 1 to R 10 、m1 and m2' are the same as those above.

[0101] As a specific example, Chemical Formula 1B can be represented by any one of Chemical Formulas 1B-1 to 1B-4.

[0102] [Chemical Formula 1B-1]

[0103]

[0104] [Chemical Formula 1B-2]

[0105]

[0106] [Chemical Formula 1B-3]

[0107]

[0108] [Chemical Formula 1B-4]

[0109]

[0110] In Chemical Formulas 1B-1 to 1B-4,

[0111] Z 1 to Z 3 、L 1 、L 2 、Ar 1 to Ar 3 、R 1 to R10 、 m1' and m2 are the same as those above.

[0112] For example, Chemical Formula 1A-1 can be represented by any one of Chemical Formulas 1A-1-1 to 1A-1-4.

[0113] [Chemical Formula 1A-1-1]

[0114]

[0115] [Chemical Formula 1A-1-2]

[0116]

[0117] [Chemical Formula 1A-1-3]

[0118]

[0119] [Chemical Formula 1A-1-4]

[0120]

[0121] In Chemical Formulas 1A-1-1 to 1A-1-4,

[0122] Z 1 to Z 3 、 L 1 、 L 2 、 Ar 1 to Ar 3 、 R 1 to R 10 、 m1 and m2' are the same as those above. For example, Chemical Formula 1A-2 can be represented by Chemical Formulas 1A-2-1 to 1A-2-4.

[0123] [Chemical Formula 1A-2-1]

[0124]

[0125] [Chemical Formula 1A-2-2]

[0126]

[0127] [Chemical Formula 1A-2-3]

[0128]

[0129] [Chemical Formula 1A-2-4]

[0130]

[0131] In Chemical Formulas 1A-2-1 to 1A-2-4, Z1 from Z 3 to L 1 to L 2 to Ar 1 from to Ar 3 to R 1 from to R 10 m1 and m2' are the same as those described above.

[0132] For example, Chemical Formula 1A-3 can be represented by any one of Chemical Formulas 1A-3-1 to 1A-3-4.

[0133] [Chemical Formula 1A-3-1]

[0134]

[0135] [Chemical Formula 1A-3-2]

[0136]

[0137] [Chemical Formula 1A-3-3]

[0138]

[0139] [Chemical Formula 1A-3-4]

[0140]

[0141] In Chemical Formulas 1A-3-1 to 1A-3-4, Z 1 to Z 3 to L 1 to L 2 to Ar 1 from to Ar 3 to R 1 from to R 10 m1 and m2' are the same as those described above.

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

[0143] [Chemical Formula 1A-4-1]

[0144]

[0145] [Chemical Formula 1A-4-2]

[0146]

[0147] [Chemical Formula 1A-4-3]

[0148]

[0149] [Chemical Formula 1A-4-4]

[0150]

[0151] In Chemical Formulas 1A-4-1 to 1A-4-4, Z 1 to Z 3 , L 1 , L 2 , Ar 1 to Ar 3 , R 1 to R 10 , m1 and m2' are the same as those above.

[0152] For example, Chemical Formula 1B-1 can be represented by any one of Chemical Formulas 1B-1-2 to 1B-1-4.

[0153] [Chemical Formula 1B-1-2]

[0154]

[0155] [Chemical Formula 1B-1-3]

[0156]

[0157] [Chemical Formula 1B-1-4]

[0158]

[0159] In Chemical Formulas 1B-1-2 to 1B-1-4, Z 1 to Z 3 , L 1 , L 2 , Ar 1 to Ar 3 , R 1 to R 10 , m1' and m2 are the same as those above.

[0160] For example, Chemical Formula 1B-2 can be represented by any one of Chemical Formulas 1B-2-1, 1B-2-3, and 1B-2-4.

[0161] [Chemical Formula 1B-2-1]

[0162]

[0163] [Chemical Formula 1B-2-3]

[0164]

[0165] [Chemical Formula 1B-2-4]

[0166]

[0167] In Chemical Formulas 1B-2-1, 1B-2-3, and 1B-2-4, Z 1 to Z 3 , L 1 , L 2 , Ar 1 to Ar 3 , R 1 to R 10 , m1' and m2 are the same as those above.

[0168] For example, Chemical Formula 1B-3 can be represented by any one of Chemical Formulas 1B-3-1, 1B-3-2, and 1B-3-4.

[0169] [Chemical Formula 1B-3-1]

[0170]

[0171] [Chemical Formula 1B-3-2]

[0172]

[0173] [Chemical Formula 1B-3-4]

[0174]

[0175] In Chemical Formulas 1B-3-1, 1B-3-2, and 1B-3-4, Z 1 to Z 3 , L 1 , L 2 , Ar 1 to Ar 3 , R 1 to R 10 , m1' and m2 are the same as those above.

[0176] For example, Chemical Formula 1B-4 can be represented by any one of Chemical Formulas 1B-4-1 to 1B-4-3.

[0177] [Chemical Formula 1B-4-1]

[0178]

[0179] [Chemical Formula 1B-4-2]

[0180]

[0181] [Chemical Formula 1B-4-3]

[0182]

[0183] In Chemical Formulas 1B-4-1 to 1B-4-3, Z 1 to Z 3 , L 1 , L 2 , Ar 1 to Ar 3 , R 1 to R 10 , m1' and m2 are the same as those described above.

[0184] In the examples, the first compound can be represented by any one of Chemical Formulas 1A-1-2, 1A-2-2, 1A-3-2, 1A-4-2, 1B-1-2, 1B-2-2, 1B-3-2, and 1B-4-2.

[0185] In a specific embodiment, the first compound can be represented by any one of Chemical Formulas 1A-1-2, 1A-4-2, 1B-1-2, and 1B-4-2.

[0186] For example, in Chemical Formula 1, Ar 1 and Ar 2 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 anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terrylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

[0187] As a specific example, in Chemical Formula 1, Ar 1 and Ar 2 can each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0188] For example, in Chemical Formula 1, L 1 and L 2 can each independently be a single bond or a substituted or unsubstituted phenylene group.

[0189] For example, L 1 -Ar 1 and L 2 -Ar 2 in Chemical Formula 1 can each independently be selected from the substituents listed in Group I.

[0190] [Group I]

[0191]

[0192] In Group I,

[0193] R 18 to R 20 are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, or a substituted or unsubstituted C6-C12 aryl group,

[0194] Ar 5 is a substituted or unsubstituted C6-C12 aryl group,

[0195] m10 is an integer from 1 to 5,

[0196] m11 is an integer from 1 to 4,

[0197] m12 is an integer from 1 to 3, and

[0198] * is the connecting point.

[0199] For example, in Chemical Formula 1, Ar 3 can be a substituted or unsubstituted C6-C12 aryl group.

[0200] As a specific example, in Chemical Formula 1, Ar 3 can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0201] For example, in Chemical Formula 1, R 1 and R 2 can each independently be hydrogen, deuterium, or a substituted or unsubstituted C6-C12 aryl group.

[0202] For example, in Chemical Formula 1, R 3 to R 8 can each independently be hydrogen, deuterium, or a substituted or unsubstituted C6-C20 aryl group.

[0203] As a specific example, in Chemical Formula 1, R 1 to R 8 can each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0204] The first compound can be, for example, one selected from the compounds listed in Group 1.

[0205] [Group 1]

[0206]

[0207]

[0208]

[0209] The second compound can be represented by Chemical Formula 2.

[0210] [Chemical Formula 2]

[0211]

[0212] In Chemical Formula 2,

[0213] X 1 is O or S,

[0214] Ar 4 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof,

[0215] R 11 to R 14 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,

[0216] R 15 to R 17 are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group,

[0217] m4, m5, m7, and m8 are each independently an integer from 1 to 3, and

[0218] m3, m6, and m9 are each independently an integer from 1 to 4.

[0219] The bi-carbazole having a phenyl-substituted dibenzofuran (or dibenzothiophene) at the 9th position has the property of shortening the distance between the molecules of the hole property compound and the molecules of the electron property compound. In particular, the LUMO of the hole property compound and the LUMO of the electron property compound are closely arranged such that the LUMO of the electron property compound extends to the LUMO of the hole property compound and are deposited in an arrangement favorable for electron transfer. Due to the above structural arrangement, the low drive / high efficiency characteristics of the organic light-emitting diode using the above structural arrangement can be achieved.

[0220] In particular, when used together with the above first compound, charge balance is suitably maintained and exciton generation is favorable, thereby enabling the implementation of high-efficiency device characteristics.

[0221] In Chemical Formula 2, when m3 is greater than or equal to 2, each R 11 can be the same as or different from each other.

[0222] In Chemical Formula 2, when m4 is greater than or equal to 2, each R 12 may be the same as or different from each other.

[0223] In Chemical Formula 2, when m5 is greater than or equal to 2, each R 13 may be the same as or different from each other.

[0224] In Chemical Formula 2, when m6 is greater than or equal to 2, each R 14 may be the same as or different from each other.

[0225] In Chemical Formula 2, when m7 is greater than or equal to 2, each R 15 may be the same as or different from each other.

[0226] In Chemical Formula 2, when m8 is greater than or equal to 2, each R 16 may be the same as or different from each other.

[0227] In Chemical Formula 2, when m9 is greater than or equal to 2, each R 17 may be the same as or different from each other.

[0228] For example, the second compound may be represented by any one of Chemical Formulas 2-1 to 2-4.

[0229]

[0230]

[0231] In Chemical Formulas 2-1 to 2-4, X 1 , Ar 4 , R 11 to R 17 and m3 to m9 are the same as those described above.

[0232] As a specific example, Chemical Formula 2-1 may be represented by any one of Chemical Formulas 2-1-1 to 2-1-16.

[0233]

[0234]

[0235] In Chemical Formulas 2-1-1 to 2-1-16, X 1 , Ar 4 , R 11 to R 17 and m3 to m9 are the same as those described above.

[0236] As a specific example, Chemical Formula 2-1 may be represented by any one of Chemical Formulas 2-2-1 to 2-2-16.

[0237]

[0238]

[0239] In Chemical Formulas 2-2-1 to 2-2-16, X 1 , Ar 4 , R 11 to R 17 and m3 to m9 are the same as those above. As a specific example, Chemical Formula 2-3 can be represented by any one of Chemical Formulas 2-3-1 to 2-3-16.

[0240] [Chemical Formula 2-3-1][Chemical Formula 2-3-2][Chemical Formula 2-3-3]

[0241]

[0242]

[0243] In Chemical Formulas 2-3-1 to 2-3-16, X 1 , Ar 4 , R 11 to R 17 and m3 to m9 are the same as those above.

[0244] As a specific example, Chemical Formula 2-4 can be represented by any one of Chemical Formulas 2-4-1 to 2-4-10.

[0245]

[0246]

[0247] In Chemical Formulas 2-4-1 to 2-4-16, X 1 , Ar 4 , R 11 to R 17 and m3 to m9 are the same as those above.

[0248] For example, the second compound can be represented by any one of Chemical Formulas 2-1-11, 2-2-12, 2-3-13, and 2-4-8.

[0249] For example, in Chemical Formula 2, Ar 4 can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenyl group.

[0250] As a specific example, in Chemical Formula 2, Ar 4 may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0251] For example, in Chemical Formula 2, R 11 to R 14 may each independently be hydrogen, deuterium, 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.

[0252] As a specific example, in Chemical Formula 2, R 11 to R 14 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.

[0253] As a more specific example, in Chemical Formula 2, R 11 to R 14 may each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0254] For example, the second compound may be one selected from the compounds listed in Group 2, but is not limited thereto.

[0255] [Group 2]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264] The first compound and the second compound may be included at a weight ratio of, for example, 1:99 to 99:1. Within this range, the desired weight ratio can be adjusted using the electron-transporting ability of the first compound and the hole-transporting ability of the second compound to achieve bipolar characteristics and thus improve efficiency and lifespan. Within this range, the first compound and the second compound may be included at a weight ratio of, for example, 10:90 to 90:10, 20:80 to 80:20 (e.g., 20:80 to 70:30, 20:80 to 60:40, or 30:70 to 60:40). As a specific example, the first compound and the second compound may be included at a weight ratio of 40:60, 50:50, or 60:40.

[0265] In addition to the above-mentioned first compound and second compound, one or more compounds may also be included.

[0266] For example, the composition for the aforementioned organic optoelectronic device may also include a dopant.

[0267] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.

[0268] A dopant is a material that is mixed in a small amount with the composition for an organic optoelectronic device to cause luminescence, and may generally be a material that emits light through multiple excitations to a triplet state or a higher state, such as a metal complex. The dopant may be, for example, an inorganic compound, an organic compound, or an organic-inorganic compound, and may include one or two or more types.

[0269] Examples of the dopant may be phosphorescent dopants, and examples of the phosphorescent dopants may include organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[0270] [Chemical Formula Z]

[0271] LX 2

[0272] In Chemical Formula Z, M is a metal, and L and X 2 are the same or different and are ligands that form a complex compound with M.

[0273] M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L and X 2 may be, for example, bidentate ligands.

[0274] L and X 2 Examples of ligands represented by 2 may be selected from the chemical formulas of Group A, but are not limited thereto.

[0275] [Group A]

[0276]

[0277]

[0278] In Group A,

[0279] R 300 to R 302 are each independently hydrogen, deuterium, a C1-C30 alkyl group which may or may not be halogen-substituted, a C6-C30 aryl group which may or may not be substituted with a C1-C30 alkyl group, or a halogen, and

[0280] R 303 to R 324 are each independently 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.

[0281] For example, it may contain a dopant represented by Chemical Formula IV.

[0282] [Chemical Formula IV]

[0283]

[0284] In Chemical Formula IV,

[0285] R 101 to R 116 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 ,

[0286] R 132 to R 134Each independently is a C1-C6 alkyl group,

[0287] R 101 to R 116 at least one of which is a functional group represented by Chemical Formula IV-1,

[0288] L 100 is a bidentate ligand of a monovalent anion and is a ligand coordinated with iridium through a lone pair carbon or heteroatom, and

[0289] n1 and n2 each independently are any one of integers from 0 to 3, and n1 + n2 is any one of integers from 1 to 3,

[0290] [Chemical Formula IV-1]

[0291]

[0292] wherein, in Chemical Formula IV-1,

[0293] R 135 to R 139 each independently are 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

[0294] * means a part connected to a carbon atom.

[0295] For example, a dopant represented by Chemical Formula Z-1 may be included.

[0296] [Chemical Formula Z-1]

[0297]

[0298] In Chemical Formula Z-1, rings A, B, C and D may each independently be a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0299] R A , R B , R C and R D may each independently be mono-substituted, di-substituted, tri-substituted or tetra-substituted, or unsubstituted;

[0300] L B , L C and L D may each independently be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof. When nA is 1, L Emay 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 is absent;

[0301] R A 、R B 、R C 、R D 、R and R' may each independently be hydrogen, deuterium, a halogen, an alkyl group, a cycloalkyl group, a heteroalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, a silyl group, an alkenyl group, a cycloalkenyl group, a heteroalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an acyl group, a carbonyl group, a carboxyl group, an ester group, a nitrile group, an isonitrile group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, or a combination thereof; any adjacent R A 、R B 、R C 、R D 、R and R' may optionally be linked 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.

[0302] The dopant according to the embodiment may be a platinum complex and may be represented by Chemical Formula V.

[0303] [Chemical Formula V]

[0304]

[0305] In Chemical Formula V,

[0306] X 100 may be O, S, or NR 131 ,

[0307] R 117 to R 131 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 ,

[0308] R 132 to R 134 may each independently be a C1 to C6 alkyl group, and

[0309] R 117 to R 131At least one of them may be -SiR 132 R 133 R 134 or tert-butyl.

[0310] Hereinafter, an organic optoelectronic device including the aforementioned composition for an organic optoelectronic device will be described.

[0311] The organic optoelectronic device may be a suitable device for converting electrical energy into light energy, such as an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, or an organic photoreceptor drum, and vice versa.

[0312] In this document, an organic light-emitting diode as an example of an organic optoelectronic device will be described with reference to the accompanying drawings.

[0313] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0314] Referring to Figure 1 , an organic light-emitting diode (100) according to an embodiment may include an anode (120) and a cathode (110) facing each other, and an organic layer (105) located between the anode (120) and the cathode (110).

[0315] The anode (120) may be made of a conductor having a large work function to facilitate hole injection, and may be a metal, a metal oxide, or a conductive polymer. The anode (120) may be: a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, and similar metals or their alloys; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and similar metal oxides; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0316] The cathode (110) may be made of a conductor having a small work function to facilitate electron injection, and may be a metal, a metal oxide, or a conductive polymer. The cathode (110) may be: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, and similar metals or their alloys; or a multi-layer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, or BaF2 / Ca.

[0317] The organic layer (105) may contain the aforementioned composition for an organic optoelectronic device.

[0318] The organic layer (105) may include a light-emitting layer (130), and the light-emitting layer (130) may contain the aforementioned composition for an organic optoelectronic device.

[0319] The composition for an organic optoelectronic device that further contains a dopant may be a green light-emitting composition.

[0320] The light-emitting layer (130) may contain the aforementioned composition for an organic optoelectronic device as a phosphorescent host.

[0321] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0322] The charge transport region may be a hole transport region (140).

[0323] The hole transport region (140) may help to further improve the hole injection and / or hole mobility between the anode (120) and the light-emitting layer (130), and may block electrons.

[0324] In an embodiment, the hole transport region (140) may include a hole transport layer located between the anode (120) and the light-emitting layer (130) and a hole transport auxiliary layer located 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 contain at least one of the compounds in Group B.

[0325] [Group B]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332] (Dn refers to the number of deuterium substitutions and represents a structure having one or more deuterium substitutions)

[0333] In the hole transport region, 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.

[0334] In addition, the charge transport region can be, for example, an electron transport region (150).

[0335] The electron transport region (150) can further improve electron injection and / or electron mobility, and can block holes between the cathode (110) and the light - emitting layer (130).

[0336] Specifically, the electron transport region (150) can include an electron transport layer located between the cathode (110) and the light - emitting layer (130) and an electron transport auxiliary layer located 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 can contain at least one of the compounds in Group C.

[0337] [Group C]

[0338]

[0339]

[0340]

[0341] Embodiments of the present invention can provide an organic light - emitting diode including a light - emitting layer as an organic layer.

[0342] Another embodiment of the present invention can provide an organic light - emitting diode including a hole transport region and a light - emitting layer as organic layers.

[0343] Another embodiment of the present invention can provide an organic light - emitting diode including an electron transport region and a light - emitting layer as organic layers.

[0344] As Figure 1 shown, embodiments of the present invention can provide an organic light - emitting diode that also includes a hole transport region (140) and an electron transport region (150) as organic layers (105) in addition to the light - emitting layer (130).

[0345] In another embodiment of the present invention, the organic light - emitting diode can further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as organic layers in addition to the light - emitting layer.

[0346] An organic light-emitting diode can be manufactured by forming an anode or a cathode on a substrate and then forming an organic layer by dry film methods such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming a cathode or an anode on the organic layer.

[0347] The organic light-emitting diode can be applied to an organic light-emitting display device.

[0348] Forms of implementing the present invention

[0349] Hereinafter, embodiments will be described in more detail with reference to examples. However, these examples are merely exemplary, and the scope of the present invention is not limited thereto.

[0350] (Synthesis of the first compound)

[0351] Synthesis Example 1: Synthesis of Compound A-17

[0352] [Reaction Scheme 1]

[0353]

[0354] Step 1: Synthesis of Intermediate A-17-1

[0355] Intermediate 4-bromo-1-chloro-2-fluorobenzene (75 g, 358.1 mmol), bis(pinacolato)diboron (109.1 g, 429.7 mmol), potassium acetate (105.4 g, 1074.3 mmol), and Pd(dppf)Cl2 (14.6 g, 17.9 mmol) were placed in a round-bottom flask and dissolved in 900 mL of toluene. The mixture was refluxed and stirred at 125 °C for 8 hours. When the reaction was completed, the resulting product was cooled to room temperature, and after removing the salt by filtration, an excess of dichloromethane (DCM) and distilled water were added thereto for extraction. The product obtained therefrom was treated by column chromatography (hexane:DCM (40%)) to obtain 70.0 g (76%) of intermediate A-17-1.

[0356] Step 2: Synthesis of Intermediate A-17-2

[0357] Intermediate A-17-1 (67.7 g, 263.8 mmol), 1-bromo-2-nitrobenzene (41.0 g, 202.9 mmol), K2CO3 (56.1 g, 405.9 mmol), and Pd(PPh3)4 (7.0 g, 6.1 mmol) were placed in a round-bottom flask and then dissolved in tetrahydrofuran (THF) (700 mL) and distilled water (350 mL), and then stirred at 80 °C for 6 hours. When the reaction was complete, after separating the aqueous layer using a separatory funnel, the organic layer obtained therefrom was subjected to vacuum distillation. The product obtained therefrom was treated by column chromatography (hexane:DCM (40%)) to obtain 37.0 g (72%) of Intermediate A-17-2.

[0358] Step 3: Synthesis of Intermediate A-17-3

[0359] Intermediate A-17-2 (37.0 g, 148.5 mmol) and PPh3 (116.8 g, 445.5 mmol) were placed in a round-bottom flask and dissolved in 500 mL of dichlorobenzene (DCB), and then stirred at 200 °C for 6 hours. When the reaction was complete, the organic layer obtained therefrom was subjected to vacuum distillation. The product obtained therefrom was treated by column chromatography (hexane:DCM (20%)) to obtain 15.0 g (46%) of Intermediate A-17-3.

[0360] Step 4: Synthesis of Intermediate A-17-4

[0361] Intermediate A-17-3 (11.6 g, 53.0 mmol), iodobenzene (37.9 g, 186.0 mmol), CuI (2.0 g, 11.0 mmol), 1,10-phenanthroline (1.9 g, 11.0 mmol), and K2CO3 (11.0 g, 80.0 mmol) were placed in a round-bottom flask and dissolved in 180 mL of dimethyl formamide (DMF), and then stirred at 180 °C for 3 hours. When the reaction was complete, the organic layer obtained therefrom was subjected to vacuum distillation, and then extracted with excess DCM and distilled water. The product obtained therefrom was treated by column chromatography (hexane:DCM (10%)) to obtain 13.0 g (83%) of Intermediate A-17-4.

[0362] Step 5: Synthesis of Intermediate A-17-5

[0363] Intermediate A-17-4 (13.0 g, 43.9 mmol), bis(pinacolato)diboron (14.5 g, 57.1 mmol), tricyclohexylphosphine (2.9 g, 10.5 mmol), potassium acetate (12.9 g, 131.8 mmol), and Pd2(dba)3 (2.9 g, 10.5 mmol) were placed in a round-bottom flask and dissolved in 150 mL of xylene. The mixture was refluxed and stirred at 150 °C for 8 hours. When the reaction was complete, the resulting mixture was cooled to room temperature and filtered, and the organic layer obtained therefrom was subjected to distillation under reduced pressure. The product obtained therefrom was treated by column chromatography (hexane:DCM (40%)) to obtain 15.0 g (88%) of Intermediate A-17-5.

[0364] Step 6: Synthesis of Intermediate A-17-6

[0365] Intermediate A-17-5 (12.4 g, 30.5 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (10.5 g, 30.5 mmol), K2CO3 (12.6 g, 91.6 mmol), and Pd(PPh3)4 (1.1 g, 0.9 mmol) were placed in a round-bottom flask and dissolved in THF (200 mL) and distilled water (100 mL), and then stirred at 90 °C for 6 hours. When the reaction was complete, after separating the aqueous layer using a separatory funnel, the organic layer obtained therefrom was subjected to distillation under reduced pressure. The product obtained therefrom was heated and dissolved in toluene, filtered through silica gel, and recrystallized to obtain 16.8 g (97%) of Intermediate A-17-6.

[0366] Step 7: Synthesis of Compound A-17

[0367] Intermediate A-17-6 (17.0 g, 30.0 mmol), 9H-carbazole (5.5 g, 33.0 mmol), and K3PO4 (9.5 g, 45.0 mmol) were placed in a round-bottom flask and dissolved in 150 mL of methylpyrrolidone (NMP), and then stirred at 200 °C for 6 hours. When the reaction was complete, the resulting mixture was subjected to distillation under reduced pressure and extracted with excess DCM and distilled water. The product obtained therefrom was treated by column chromatography (hexane:ethyl acetate (EA) (10%)) to obtain 19.4 g (91%) of Compound A-17.

[0368] Synthesis Example 2: Synthesis of Compound A-14

[0369] [Reaction Scheme 2]

[0370]

[0371] Step 1: Synthesis of Intermediate A-14-1

[0372] The intermediate 1,4-dichloro-2-nitrobenzene (37.5 g, 195.3 mmol), (2-fluorophenyl)boronic acid (28.7 g, 205.1 mmol), K2CO3 (53.9 g, 390.6 mmol) and Pd(PPh3)4 (6.7 g, 5.8 mmol) were placed in a round-bottom flask and dissolved in 700 mL of THF and 350 mL of distilled water, and then stirred at 80 °C for 6 hours. When the reaction was completed, after separating the aqueous layer using a separatory funnel, the organic layer obtained therefrom was subjected to vacuum distillation. The product obtained therefrom was treated by column chromatography (hexane:DCM (40%)) to obtain 42.7 g (97%) of intermediate A-14-1.

[0373] Step 2: Synthesis of Intermediate A-14-2

[0374] The intermediate A-14-1 (42.7 g, 169.9 mmol) and PPh3 (133.7 g, 509.7 mmol) were placed in a round-bottom flask and dissolved in DCB (500 mL), and then stirred at 200 °C for 6 hours. When the reaction was completed, the organic layer obtained therefrom was subjected to vacuum distillation. The product obtained therefrom was treated by column chromatography (hexane:DCM (50%)) to obtain 27.1 g (73%) of intermediate A-14-2.

[0375] Step 3: Synthesis of Intermediate A-14-3

[0376] The intermediate A-14-2 (27.1 g, 123.0 mmol), iodobenzene (88.0 g, 432.0 mmol), CuI (4.7 g, 25.0 mmol), 1,10-phenanthroline (4.4 g, 25.0 mmol), K2CO3 (25.6 g, 185.0 mmol) were placed in a round-bottom flask and dissolved in DMF (180 mL), and then stirred at 180 °C for 3 hours. When the reaction was completed, the organic layer obtained therefrom was subjected to vacuum distillation, and then extracted with excess DCM and distilled water. The product obtained therefrom was treated by column chromatography (hexane:DCM (10%)) to obtain 34.1 g (94%) of intermediate A-14-3.

[0377] Step 4: Synthesis of Intermediate A-14-4

[0378] Intermediate A-14-3 (34.2 g, 115.6 mmol), 9H-carbazole (21.3 g, 127.2 mmol), and K3PO4 (36.8 g, 173.4 mmol) were placed in a round-bottom flask and dissolved in NMP (150 mL), and then stirred at 200 °C for 6 hours. When the reaction was complete, the resulting product was subjected to distillation under reduced pressure, and then extracted with excess DCM and distilled water. The product obtained therefrom was treated by column chromatography (hexane: methylene chloride (MC) (30%)) to obtain 40.3 g (79%) of Intermediate A-14-4.

[0379] Step 5: Synthesis of Intermediate A-14-5

[0380] Intermediate A-14-4 (40.3 g, 90.9 mmol), bis(pinacolato)diboron (30.0 g, 118.2 mmol), tricyclohexylphosphine (6.1 g, 21.8 mmol), potassium acetate (26.8 g, 272.7 mmol), and Pd2(dba)3 (5.0 g, 5.4 mmol) were placed in a round-bottom flask and dissolved in 150 mL of xylene. The mixture was refluxed and stirred at 150 °C for 8 hours. When the reaction was complete, the resulting product was cooled to room temperature, and filtered to remove salts, and the organic layer obtained therefrom was subjected to distillation under reduced pressure. The product obtained therefrom was treated by column chromatography (hexane: DCM (40%)) to obtain 45.1 g (93%) of Intermediate A-14-5.

[0381] Step 6: Synthesis of Compound A-14

[0382] Intermediate A-14-5 (11.7 g, 19.8 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (6.8 g, 19.8 mmol), K2CO3 (8.2 g, 59.3 mmol), and Pd(PPh3)4 (0.7 g, 0.6 mmol) were placed in a round-bottom flask and dissolved in THF (130 mL) and distilled water (65 mL), and then stirred at 90 °C for 6 hours. When the reaction was complete, after separating the aqueous layer using a separatory funnel, the organic layer obtained therefrom was subjected to distillation under reduced pressure. The product obtained therefrom was heated and dissolved in toluene, and then filtered through silica and recrystallized to obtain 12.0 g (85%) of Compound A-14.

[0383] Synthesis Example 3: Synthesis of Compound A-27

[0384] [Reaction Scheme 3]

[0385]

[0386] Compound A-27 was synthesized in the same manner as in Steps 1 to 6 of Synthesis Example 2, except that 1-bromo-2-nitrobenzene was used instead of 1,4-dichloro-nitrobenzene in Step 1 of Synthesis Example 2 and (4-chloro-2-fluorophenyl)boronic acid was used instead of (2-fluorophenyl)boronic acid.

[0387] Synthesis Example 4: Synthesis of Compound A-2

[0388] [Reaction Scheme 4]

[0389]

[0390] Compound A-2 was synthesized in the same manner as in Steps 1 to 6 of Synthesis Example 2, except that 1-bromo-3-fluoro-2-nitrobenzene was used instead of 1,4-dichloro-nitrobenzene in Step 1 of Synthesis Example 2 and (4-chlorophenyl)boronic acid was used instead of (2-fluorophenyl)boronic acid.

[0391] Synthesis Example 5: Synthesis of Compound B-1

[0392] [Reaction Scheme 5]

[0393]

[0394] Step 1: Synthesis of Intermediate int-01

[0395] 1-Bromo-2,6-difluorobenzene (100 g, 518.2 mmol), 2,6-dimethoxyphenylboronic acid (99.0 g, 544.1 mmol), K2CO3 (179 g, 1295.4 mmol) and Pd(PPh3)4 (29.9 g, 25.9 mmol) were placed in a round-bottom flask and dissolved in THF (1000 mL) and distilled water (500 mL), and then refluxed with stirring at 70 °C for 12 hours. When the reaction was completed, after removing the aqueous layer therefrom, the residue was treated by column chromatography (hexane:DCM (20%)) to obtain 78 g (60%) of intermediate int-01.

[0396] Step 2: Synthesis of Intermediate int-02

[0397] The intermediate int-01 (72 g, 287.7 mmol) and pyridine hydrochloride (166.3 g, 1438.6 mmol) were placed in a round-bottom flask and refluxed with stirring at 200 °C for 24 hours. When the reaction was completed, the resulting product was cooled to room temperature and slowly poured into distilled water, and then stirred for 1 hour. The solid obtained therefrom was filtered to obtain 60 g (94%) of intermediate int-02.

[0398] Step 3: Synthesis of Intermediate int-03

[0399] The intermediate int-02 (64 g, 287.7 mmol) and K2CO3 (47.7 g, 345.3 mmol) were placed in a round-bottom flask and dissolved in NMP (200 mL), and then refluxed and stirred at 180 °C for 12 hours. When the reaction was completed, the mixture was poured into excess distilled water. The solid obtained therefrom was filtered, dissolved in ethyl acetate, and dried over MgSO4, and the organic layer was removed under reduced pressure. The product obtained therefrom was treated by column chromatography (hexane:ethyl acetate (30%)) to obtain 51 g (88%) of the intermediate int-03.

[0400] Step 4: Synthesis of Intermediate int-04

[0401] The intermediate int-03 (14 g, 69.2 mmol) and pyridine (8.4 mL, 103.9 mmol) were placed in a round-bottom flask and dissolved in DCM (150 mL). After cooling to 0 °C, trifluoromethanesulfonic anhydride (13.9 mL, 83.1 mmol) was slowly added dropwise thereto. After 6 hours, when the reaction was completed, excess distilled water was added thereto, and then stirred for 30 minutes and extracted with DCM. After removing the organic solvent under reduced pressure therefrom, 22 g (95%) of the intermediate int-04 was obtained by vacuum drying.

[0402] Step 5: Synthesis of Intermediate int-05

[0403] Except for using the intermediate int-04 (21 g, 62.8 mmol), phenylboronic acid (8.4 g, 69.1 mmol), K2CO3 (13 g, 94.2 mmol) and Pd(PPh3)4 (3.6 g, 3.1 mmol), 12.5 g (76%) of the intermediate int-05 was synthesized in the same manner as in the first step of Synthesis Example 1.

[0404] Step 6: Synthesis of Compound B-1

[0405] The intermediate int-05 (12 g, 45.8 mmol), 9-phenyl-3,3'-bicarbazole (22.4 g, 54.9 mmol) and K3PO4 (19.4 g, 91.5 mmol) were placed in a round-bottom flask and dissolved in DMF (130 mL). The solution was refluxed and stirred at 160 °C for 6 hours. When the reaction was completed, after filtering the salt, the filtrate obtained therefrom was adsorbed. 19.4 g (65%) of Compound B-1 was obtained using column chromatography (hexane:DCM (35%)).

[0406] Synthesis Example 6: Synthesis of Compound B-36

[0407] [Reaction Scheme 6]

[0408]

[0409] Step 1: Synthesis of Intermediate int-06

[0410] 1-Bromo-3-fluoro-2-iodobenzene (80 g, 265.9 mmol), 5-chloro-2-methoxyphenylboronic acid (54.5 g, 292.5 mmol), K2CO3 (73.5 g, 531.8 mmol) and Pd(PPh3)4 (15.4 g, 13.3 mmol) were placed in a round-bottom flask and dissolved in THF (550 mL) and distilled water (250 mL), and then refluxed with stirring at 70 °C for 12 hours. When the reaction was complete, after removing the aqueous layer therefrom, 71.3 g (85%) of intermediate int-06 was obtained by column chromatography (hexane:DCM (20%)).

[0411] Step 2: Synthesis of Intermediate int-07

[0412] Except for using intermediate int-06 (70 g, 287.7 mmol) and pyridine hydrochloride (128.2 g, 1109.1 mmol), 61.5 g (92%) of intermediate int-07 was obtained in the same manner as in the second step of Synthesis Example 5.

[0413] Step 3: Synthesis of Intermediate int-08

[0414] Except for using intermediate int-07 (61 g, 202.3 mmol) and K2CO3 (41.9 g, 303.4 mmol), 48.4 g (85%) of intermediate int-08 was obtained in the same manner as in the third step of Synthesis Example 5.

[0415] Step 4: Synthesis of Intermediate int-09

[0416] Intermediate int-08 (48 g, 170.5 mmol), phenylboronic acid (22.9 g, 187.6 mmol), K2CO3 (47.3 g, 341.0 mmol) and Pd(PPh3)4 (9.9 g, 8.5 mmol) were placed in a round-bottom flask and dissolved in THF (560 mL) and distilled water (170 mL), and then refluxed with stirring at 70 °C for 12 hours. When the reaction was complete, after removing the aqueous layer therefrom, 35.2 g (74%) of intermediate int-09 was obtained by column chromatography (hexane:DCM (20%)).

[0417] Step 5: Synthesis of Compound B-36

[0418] The intermediate int-09 (30 g, 107.6 mmol), 9-phenyl-3,3'-bicarbazole (44 g, 107.6 mmol), sodium tert-butoxide (20.7 g, 215.3 mmol), tri-tert-butylphosphine (2.2 g, 10.8 mmol), and Pd2(dba)3 (4.9 g, 5.4 mmol) were placed in a round-bottom flask and dissolved in xylene (360 mL), and then refluxed and stirred at 150 °C for 6 hours. When the reaction was complete, after removing the salt by filtration, the filtrate obtained therefrom was adsorbed using silica gel. 39.9 g (57%) of compound B-36 was obtained by column chromatography (hexane:DCM 35%).

[0419] Synthesis Example 7: Synthesis of Compound B-71

[0420] [Reaction Scheme 7]

[0421]

[0422] Step 1: Synthesis of Intermediate int-10

[0423] The intermediate int-10 was synthesized in the same manner as in the first step of Synthesis Example 6, except that 4-chloro-2-methoxyphenylboronic acid was used instead of 5-chloro-2-methoxyphenylboronic acid.

[0424] Step 2: Synthesis of Intermediate int-11

[0425] The intermediate int-11 was synthesized in the same manner as in the second step of Synthesis Example 6.

[0426] Step 3: Synthesis of Intermediate int-12

[0427] The intermediate int-12 was synthesized in the same manner as in the third step of Synthesis Example 6.

[0428] Step 4: Synthesis of Intermediate int-13

[0429] The intermediate int-13 was synthesized in the same manner as in the fourth step of Synthesis Example 6.

[0430] Step 5: Synthesis of Compound B-71

[0431] Compound B-71 was synthesized in the same manner as in the fifth step of Synthesis Example 6.

[0432] Synthesis Example 8: Synthesis of Compound B-106

[0433] [Reaction Scheme 8]

[0434]

[0435] Step 1: Synthesis of Intermediate int-14

[0436] The intermediate int-14 was synthesized in the same manner as in the first step of Synthesis Example 5, except that 1-bromo-2,3-difluorobenzene was used instead of 1-bromo-2,6-difluorobenzene.

[0437] Step 2: Synthesis of Intermediate int-15

[0438] The intermediate int-15 was synthesized in the same manner as in the second step of Synthesis Example 5.

[0439] Step 3: Synthesis of Intermediate int-16

[0440] The intermediate int-16 was synthesized in the same manner as in the third step of Synthesis Example 5.

[0441] Step 4: Synthesis of Intermediate int-17

[0442] The intermediate int-17 was synthesized in the same manner as in the fourth step of Synthesis Example 5.

[0443] Step 5: Synthesis of Intermediate int-18

[0444] The intermediate int-18 was synthesized in the same manner as in the fifth step of Synthesis Example 5.

[0445] Step 6: Synthesis of Compound B-106

[0446] The intermediate int-106 was synthesized in the same manner as in the sixth step of Synthesis Example 5.

[0447] Comparative Synthesis Example 1: Synthesis of Compound C-1

[0448]

[0449] Compound C-1 was synthesized with reference to the known synthesis method in the registered patent KR 1849747 B1.

[0450] Comparative Synthesis Example 2: Synthesis of Compound C-2

[0451] [Reaction Scheme 9]

[0452]

[0453] Step 1: Synthesis of Intermediate int-23

[0454] 1,3 - Dibromo - 5 - chlorobenzene (45 g, 166.5 mmol), phenylboronic acid (19.3 g, 158.1 mmol), K2CO3 (41.4 g, 299.6 mmol) and Pd(PPh3)4 (9.6 g, 8.3 mmol) were placed in a round - bottom flask and dissolved in THF (600 mL) and distilled water (150 mL), and then refluxed and stirred at 70 °C for 8 hours. When the reaction was completed, after removing the aqueous layer, 25 g (59%) of intermediate int - 23 was obtained by column chromatography (hexane:DCM (15%)).

[0455] Step 2: Synthesis of Intermediate int-24

[0456] Intermediate int - 23 (25 g, 93.4 mmol), 3 - dibenzofuranylboronic acid (21.8 g, 102.8 mmol), K2CO3 (25.8 g, 186.9 mmol) and Pd(PPh3)4 (5.4 g, 4.7 mmol) were placed in a round - bottom flask and dissolved in THF (400 mL) and distilled water (100 mL), and then refluxed and stirred at 70 °C for 8 hours. When the reaction was completed, after removing the aqueous layer therefrom, 24.4 g (67%) of intermediate int - 24 was obtained using column chromatography (hexane:DCM 30%).

[0457] Step 3: Synthesis of Intermediate int-25

[0458] Intermediate int - 24 (24 g, 67.6 mmol), bis(pinacolato)diboron (20.6 g, 81.2 mmol), tricyclohexylphosphine (3.3 g, 13.5 mmol), potassium acetate (13.3 g, 135.3 mmol) and Pd(dppf)Cl2 (1.7 g, 2.0 mmol) were placed in a round - bottom flask and dissolved in xylene (250 mL). The mixture was refluxed and stirred at 150 °C for 8 hours. When the reaction was completed, the resulting product was cooled to room temperature, filtered to remove salts, and extracted with excess DCM and distilled water. 23.6 g (78%) of intermediate int - 25 was obtained by column chromatography (hexane:DCM (40%)).

[0459] Step 4: Synthesis of Intermediate int-26

[0460] 2,4 - Dichloro - 6 - phenyl - 1,3,5 - triazine (20 g, 88.5 mmol), 3 - dibenzofuranylboronic acid (17.8 g, 84.1 mmol), K2CO3 (24.5 g, 176.9 mmol), and Pd(dppf)Cl2 (3.6 g, 4.4 mmol) were placed in a round - bottom flask and dissolved in toluene (250 mL) and distilled water (90 mL), and then stirred at 60 °C for 6 hours. When the reaction was complete, after removing the aqueous layer using a separatory funnel, the organic layer obtained therefrom was subjected to distillation under reduced pressure. The product obtained therefrom was heated and dissolved in monochlorobenzene, subjected to silica filtration, and recrystallized to obtain 14.4 g (48%) of intermediate int - 26.

[0461] Step 5: Synthesis of Compound C-2

[0462] Intermediate int - 26 (14.1 g, 39.4 mmol), intermediate int - 25 (18.5 g, 14.4 mmol), K2CO3 (10.9 g, 78.8 mmol), and Pd(PPh3)4 (2.3 g, 2.0 mmol) were placed in a round - bottom flask and dissolved in THF (200 mL) and distilled water (40 mL), and then refluxed and stirred at 70 °C for 8 hours. When the reaction was complete, after removing the aqueous layer, the solid precipitated therein was filtered. The product obtained therefrom was heated and dissolved in monochlorobenzene, and then subjected to silica filtration and recrystallized to obtain 18.2 g (72%) of compound C - 2.

[0463] Comparative Synthesis Example 3: Synthesis of Compound C-3

[0464] [Reaction Scheme 10]

[0465]

[0466] Step 1: Synthesis of Intermediate int-27

[0467] 2 - Bromo - 4 - chlorodibenzofuran (30.3 g, 107.6 mmol), 9H - carbazole (18.0 g, 107.6 mmol), sodium tert - butoxide (20.7 g, 215.3 mmol), tri - tert - butylphosphine (2.2 g, 10.8 mmol), and Pd2(dba)3 (4.9 g, 5.4 mmol) were placed in a round - bottom flask and dissolved in xylene (550 mL), and then refluxed and stirred at 150 °C for 8 hours. When the reaction was complete, after removing the salt by filtration, the filtrate obtained therefrom was adsorbed. 21.4 g (54%) of intermediate int - 27 was obtained by column chromatography (hexane:DCM (40%)).

[0468] Step 2: Synthesis of Intermediate int-28

[0469] The intermediate int-27 (21.2 g, 57.6 mmol), bis(pinacolato)diboron (17.6 g, 69.2 mmol), tricyclohexylphosphine (2.8 g, 11.5 mmol), potassium acetate (11.3 g, 115.3 mmol) and Pd2(dba)3 (1.6 g, 1.7 mmol) were placed in a round-bottom flask and dissolved in xylene (200 mL). The mixture was refluxed with stirring at 160 °C for 8 hours. When the reaction was completed, the resulting product was cooled to room temperature, filtered to remove salts, and extracted with excess DCM and distilled water. 23.3 g (88%) of the intermediate int-28 was obtained by column chromatography (hexane:DCM (40%)).

[0470] Step 3: Synthesis of Compound C-3

[0471] 2-Chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (13.5 g, 39.3 mmol), intermediate int-28 (18.9 g, 41.2 mmol), K2CO3 (10.9 g, 78.5 mmol) and Pd(PPh3)4 (2.3 g, 2.0 mmol) were placed in a round-bottom flask and dissolved in THF (150 mL) and distilled water (40 mL), and then refluxed with stirring at 70 °C for 12 hours. When the reaction was completed, the solid was separated from it by filtration and recrystallized from monochlorobenzene to obtain 18.1 g (72%) of compound C-3.

[0472] Comparative Synthesis Example 4: Synthesis of Compound C-4

[0473]

[0474] Compound C-4 was synthesized by referring to the synthesis method known in the published patent CN 114075204 A.

[0475] Comparative Synthesis Example 5: Synthesis of Compound C-5

[0476]

[0477] Compound C-5 was synthesized by referring to the synthesis method known in the registered patent KR 2290362 B1.

[0478] Comparative Synthesis Example 6: Synthesis of Compound C-6

[0479]

[0480] Compound C-6 was synthesized by referring to the synthesis method known from the publicly disclosed patent KR 2022-0087827.

[0481] (Manufacture of Organic Light-Emitting Diode)

[0482] Example 1

[0483] A glass substrate coated with indium tin oxide (ITO) was washed using distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent (such as isopropyl alcohol, acetone, methanol, and similar solvents) and dried. Then, the glass substrate was moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and the glass substrate was moved to a vacuum depositor. The obtained ITO transparent electrode was used as the anode, and compound A doped with 3% 2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)-malononitrile (2-(7-dicyanomethylene-1,3,4,5,6,8,9,10-octafluoro-7H-pyrene-2-ylidene)-malononitrile, NDP-9) (obtainable from Novaled) was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer, and compound A was deposited on the hole injection layer to form a 1350 Å thick hole transport layer. On the hole transport layer, compound B with a thickness of 350 Å was deposited to form a hole transport auxiliary layer. On the hole transport auxiliary layer, a 330 Å thick light-emitting layer was formed by simultaneously using compound A-17 obtained in Synthesis Example 1 and compound B-1 obtained in Synthesis Example 5 as the host at a weight ratio of 4:6 and by vacuum depositing 7 wt% of PhGD as the dopant. Subsequently, on the light-emitting layer, compound C with a thickness of 50 Å was deposited to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1:1 to form a 300 Å thick electron transport layer. On the electron transport layer, 15 Å thick LiQ and 1200 Å thick Al were sequentially vacuum deposited to manufacture an organic light-emitting diode.

[0484] ITO / Compound A (3% NDP-9 doped, 100 Å) / Compound A (1350 Å) / Compound B (350 Å) / EML [93 wt% of host (Compound A-17:Compound B-1 = 4:6 weight / weight (w / w)):7 wt% of PhGD] (330 Å) / Compound C (50 Å) / Compound D:LiQ (300 Å) / LiQ (15 Å) / Al (1200 Å)

[0485] Compound A: N-(Biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0486] Compound B: N,N-Bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0487] Compound C: 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0488] Compound D: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0489] [PhGD]

[0490]

[0491] Examples 2 to 8 and Comparative Examples 1 to 6

[0492] Diodes of Examples 2 to 8 and Comparative Examples 1 to 6 were fabricated in the same manner as in Example 1 except that the host was changed as shown in Table 1.

[0493] Evaluation

[0494] (1) Measurement of current density change dependent on voltage change

[0495] While increasing the voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), the current value flowing in the unit device of the obtained organic light-emitting diode was measured, and the measured current value was divided by the area to provide the result.

[0496] (2) Measurement of luminance change dependent on voltage change

[0497] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0498] (3) Measurement of luminous efficiency

[0499] The luminous efficiency (candela per area (cd / A)) at the same current density (10 milliamperes per square centimeter (mA / cm 2 )) was calculated using the luminance and current density measured in (1) and (2) above.

[0500] The luminous efficiencies of Examples 1 to 8 and Comparative Examples 1 to 6 were calculated as relative values based on Comparative Example 1 and are listed in Table 1.

[0501] (4) Measurement of driving voltage

[0502] The results were obtained by measuring the driving voltage of each diode at 15 mA / cm² using a current-voltage meter (Keithley 2400).

[0503] The driving voltages of Examples 1 to 8 and Comparative Examples 1 to 6 were calculated as relative values based on Comparative Example 1 and are listed in Table 1.

[0504] (Table 1)

[0505] First Subject Second Subject Drive Voltage Ratio (%) Efficiency Ratio (%) Example 1 A-17 B-1 94 110 Example 2 A-17 B-36 92 109 Example 3 A-17 B-71 96 107 Example 4 A-17 B-106 93 105 Example 5 A-14 B-1 96 109 Example 6 A-14 B-36 94 108 Example 7 A-27 B-36 93 104 Example 8 A-2 B-36 92 107 Comparative Example 1 C-1 B-36 100 100 Comparative Example 2 C-2 B-71 104 97 Comparative Example 3 C-3 B-106 107 95 Comparative Example 4 C-4 B-106 109 91 Comparative Example 5 A-17 C-5 102 97 Comparative Example 6 A-17 C-6 99 100

[0506] Referring to Table 1, compared to the organic light-emitting diodes according to Comparative Examples 1 to 6, the organic light-emitting diodes according to Examples 1 to 8 have significantly improved efficiencies while maintaining a low driving voltage.

[0507] Although the present invention has been described in connection with exemplary embodiments presently regarded as 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 represented by Chemical Formula 1; And A second compound represented by Chemical Formula 2: [Chemical Formula 1] Wherein, in Chemical Formula 1, Z 1 to Z 3 each independently is N or C-R a , Z 1 to Z 3 at least two of them are N, L 1 and L 2 each independently is a single bond or a substituted or unsubstituted C6-C20 arylene group, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, Ar 3 is a substituted or unsubstituted C6-C20 aryl group, R 1 and R 2 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a combination thereof, m1 is an integer from 1 to 3, m2 is an integer from 1 to 4, and R a and R 3 to R 10 each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof; [Chemical Formula 2] Wherein, in Chemical Formula 2, X 1 is O or S, Ar 4 is a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof, R 11 to R 14 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, R 15 to R 17 each independently is hydrogen, deuterium, or a substituted or unsubstituted phenyl group, m4, m5, m7 and m8 are each independently an integer from 1 to 3, and m3, m6 and m9 are each independently an integer from 1 to 4.

2. The composition for the organic optoelectronic device according to claim 1, wherein Chemical Formula 1 is represented by Chemical Formula 1A or Chemical Formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] Among them, In Chemical Formula 1A and Chemical Formula 1B, Z 1 to Z 3 , L 1 , L 2 , Ar 1 to Ar 3 , R 1 to R 10 , m1 and m2 are as defined in claim 1, m1' is an integer of 1 or 2, and m2' is an integer from 1 to 3.

3. The composition for the organic optoelectronic device according to claim 2, wherein Chemical Formula 1A is represented by Chemical Formulas 1A-1 to 1A-4: [Chemical Formula 1A-1] [Chemical Formula 1A-2] [Chemical Formula 1A-3] [Chemical Formula 1A-4] In Chemical Formulas 1A-1 to 1A-4, Z 1 to Z 3 、L 1 、L 2 、Ar 1 to Ar 3 、R 1 to R 10 、m1 and m2' are the same as defined in claim 2.

4. The composition for the organic optoelectronic device according to claim 2, wherein Chemical Formula 1B is represented by any one of Chemical Formulas 1B-1 to 1B-4: [Chemical Formula 1B-1] [Chemical Formula 1B-2] [Chemical Formula 1B-3] [Chemical Formula 1B-4] Among them, In Chemical Formulas 1B-1 to 1B-4, Z 1 to Z 3 、L 1 、L 2 、Ar 1 to Ar 3 、R 1 to R 10 、m1' and m2 are the same as defined in claim 2.

5. The composition for the organic optoelectronic device according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1A-1-2, 1A-2-2, 1A-3-2, 1A-4-2, 1B-1-2, 1B-2-2, 1B-3-2 and 1B-4-2: [Chemical Formula 1A-1-2] [Chemical Formula 1A-2-2] [Chemical Formula 1A-3-2] [Chemical Formula 1A-4-2] [Chemical Formula 1B-1-2] [Chemical Formula 1B-3-2] [Chemical Formula 1B-4-2] Among them, In Chemical Formulas 1A-1-2, 1A-2-2, 1A-3-2, 1A-4-2, 1B-1-2, 1B-2-2, 1B-3-2, 1B-4-2, Z 1 to Z 3 、L 1 、L 2 、Ar 1 to Ar 3 、R 1 to R 10 、m1 and m2 are the same as defined in claim 1, m1' is an integer of 1 or 2, and m2' is an integer from 1 to 3.

6. The composition for the organic optoelectronic device according to claim 1, wherein Ar in Chemical Formula 1 1 and Ar 2 each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted terrylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

7. The composition for the organic optoelectronic device according to claim 1, wherein R in Chemical Formula 1 3 to R 8 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6-C20 aryl group.

8. The composition for the organic optoelectronic device according to claim 1, wherein The second compound is represented by any one of Chemical Formulas 2-1 to 2-4: Among them, In Chemical Formulas 2-1 to 2-4, X 1 , Ar 4 , R 11 to R 17 and m3 to m9 are the same as defined in claim 1.

9. The composition for the organic optoelectronic device according to claim 8, wherein The second compound is represented by Chemical Formulas 2-1-11, 2-2-11, 2-3-11 and 2-4-11: Among them, In Chemical Formula 2-1-11, Chemical Formula 2-2-11, Chemical Formula 2-3-11, and Chemical Formula 2-4-11, X 1 , Ar 4 , R 11 to R 17 and m3 to m9 are the same as those defined in Claim 1.

10. The composition for the organic optoelectronic device according to claim 1, wherein Ar in Chemical Formula 2 4 is 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 triphenylene group, or a substituted or unsubstituted fluorenyl group.

11. The composition for an organic optoelectronic device according to claim 1, wherein the first compound is one selected from the compounds listed in Group 1, and the second compound is one selected from the compounds listed in Group 2: [Group 1] [Group 2] 12. An organic optoelectronic device, comprising: an anode and a cathode facing each other, at least one organic layer located between the anode and the cathode, wherein the organic layer contains the composition for an organic optoelectronic device according to any one of claims 1 to 11.

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

14. The organic optoelectronic device according to claim 12, wherein the composition for an organic optoelectronic device further contains a phosphorescent dopant.

15. The organic optoelectronic device according to claim 13, wherein the composition for an organic optoelectronic device is a green light-emitting composition.

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

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