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

Abstract

The present invention relates to: a composition for an organic optoelectronic device, the composition comprising a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2; and an organic optoelectronic device and a display device comprising the same. Details of the chemical formula 1 and the chemical formula 2 are shown 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 the electrodes.

[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 materials between the electrodes. Summary of the Invention

[0006] Technical Problem

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

[0010] Technical Solution

[0011] According to one embodiment, the 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 are each independently N or C-R a ,

[0016] Z1 from Z to 3 at least two of them are N,

[0017] L 1 is a single bond or a substituted or unsubstituted C6 - C20 arylene,

[0018] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 - C30 aryl, and

[0019] R a and R 1 to R 8 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 - C10 alkyl, a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C2 - C30 heterocyclic group, or a combination thereof;

[0020] [Chemical formula 2]

[0021]

[0022] In Chemical formula 2,

[0023] X 1 is O or S,

[0024] Ar 3 is a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C2 - C30 heterocyclic group, or a combination thereof,

[0025] R 9 to R 12 are each independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 - C30 alkyl, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 - C30 aryl, or a substituted or unsubstituted C2 - C30 heterocyclic group,

[0026] R 13 to R 15 are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl,

[0027] m2, m3, m5, and m6 are each independently one of the integers from 1 to 3,

[0028] m1 and m4 are each independently one of the integers from 1 to 4, and

[0029] m7 is one of the integers from 1 to 5.

[0030] 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 a composition for the organic optoelectronic device.

[0031] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0032] Advantages

[0033] An organic optoelectronic device with high efficiency, long lifespan, and low drive can be achieved. Description of the Drawings

[0034] Figure 1 It is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0035] <Description of Reference Numerals>

[0036] 100: Organic light-emitting diode

[0037] 105: Organic layer

[0038] 110: Cathode

[0039] 120: Anode

[0040] 130: Light-emitting layer

[0041] 140: Hole transport region

[0042] 150: Electron transport region Detailed Description of the Embodiments

[0043] Hereinafter, embodiments of the present invention will be described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0044] 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-C30 amino group, nitro group, substituted or unsubstituted C1-C40 silyl group, C1-C30 alkyl group, C1-C10 alkylsilyl group, C6-C30 arylsilyl group, C3-C30 cycloalkyl group, C3-C30 heterocycloalkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, C1-C20 alkoxy group, C1-C10 trifluoroalkyl group, cyano group, or a combination thereof.

[0045] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, cyano, C1-C30 alkyl, C1-C10 alkylsilyl, C6-C30 arylamino, C6-C30 arylsilyl, C3-C30 cycloalkyl, C3-C30 heteroalkyl, C6-C30 aryl or C2-C30 heteroaryl. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, cyano, C1-C20 alkyl, C6-C30 arylamino, C6-C30 aryl or C2-C30 heteroaryl. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, cyano, C1-C5 alkyl, C6-C20 arylamino, C6-C18 aryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl or pyridyl. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, cyano, methyl, ethyl, propyl, butyl, C6-C20 arylamino, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl or pyridyl.

[0046] In this specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0047] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0048] In this specification, when no other definition is provided, "hetero" means that a functional group contains one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon.

[0049] In this specification, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p-orbitals, such as phenyl, naphthyl, etc.; two or more hydrocarbon aromatic moieties may be connected by a σ-bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc.; and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl, etc.

[0050] Aryl may include monocyclic, polycyclic or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0051] In this specification, "heterocyclic group" is a superordinate concept of heteroaryl group, 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.

[0052] For example, "heteroaryl group" 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, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

[0053] 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.

[0054] 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 dibenzothiophenyl group, or a combination thereof, but is not limited thereto.

[0055] 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.

[0056] 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.

[0057] Hereinafter, a composition for an organic optoelectronic device according to an embodiment is described.

[0058] 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.

[0059] The first compound may be represented by Chemical Formula 1.

[0060] [Chemical Formula 1]

[0061]

[0062] In Chemical Formula 1,

[0063] Z 1 to Z 3 are each independently N or C-R a ,

[0064] Z 1 to Z 3 at least two of which are N,

[0065] L 1 is a single bond or a substituted or unsubstituted C6 to C20 arylene,

[0066] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl, and

[0067] R a and R 1 to R 8 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0068] The first compound represented by Chemical Formula 1 has a structure in which carbazole is used as a basic skeleton and the carbazole at the 9-position is substituted with a ring containing at least one nitrogen (a nitrogen-containing 6-membered ring).

[0069] The first compound may have a structure that is prone to receiving electrons when an electric field is applied by including a ring containing at least one nitrogen, and thus can reduce the driving voltage of an organic optoelectronic device to which the compound is applied.

[0070] In addition, the first compound forms a bipolar structure by including carbazole that is prone to accepting holes, so that the flow of holes and electrons can be appropriately balanced, thereby improving the efficiency of the organic optoelectronic device to which the compound is applied.

[0071] Specifically, by connecting to a nitrogen-containing 6-membered ring in the 9-direction (N-direction) of carbazole, through the π-bond cleavage of the C-N bond, the electron cloud between HOMO and LUMO is significantly localized to the hole transport part and the electron transport part, thereby widening the HOMO-LUMO band gap, and thus the efficiency of the organic light-emitting diode to which it is applied can be further improved.

[0072] For example, in Chemical Formula 1, Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terrylene group, or a substituted or unsubstituted fluorenyl group.

[0073] As a specific example, in Chemical Formula 1, Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terrylene group.

[0074] For example, in Chemical Formula 1, R 1 to R 8 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.

[0075] As a specific example, in Chemical Formula 1, R 1 to R 8 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenylcarbazolyl group, a substituted or unsubstituted phenyldibenzofuranyl group, or a substituted or unsubstituted phenyldibenzothiophenyl group.

[0076] For example, in Chemical Formula 1, L 1It can be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted triphenylene group.

[0077] For example, in Chemical Formula 1, L 1 can be a substituted or unsubstituted phenylene group.

[0078] The first compound can be, for example, one selected from the compounds listed in Group 1.

[0079] [Group 1]

[0080]

[0081]

[0082]

[0083] The second compound can be represented by Chemical Formula 2.

[0084] [Chemical Formula 2]

[0085]

[0086] In Chemical Formula 2,

[0087] X 1 is O or S,

[0088] Ar 3 is a substituted or unsubstituted C6 - C30 aryl group, a substituted or unsubstituted C2 - C30 heterocyclic group, or a combination thereof,

[0089] R 9 to R 12 are each independently hydrogen, deuterium, cyano group, 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,

[0090] R 13 to R 15 are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group,

[0091] m2, m3, m5, and m6 are each independently one of the integers from 1 to 3,

[0092] m1 and m4 are each independently one of the integers from 1 to 4, and

[0093] m7 is one of the integers from 1 to 5.

[0094] The second compound has hole characteristics, and at least one substituent in the N-direction of the bi-carbazole is dibenzofuran (or dibenzothiophene), and the dibenzofuran (or dibenzothiophene) has a structure in which the 9-position is substituted with a phenyl group.

[0095] The bi-carbazole having dibenzofuran (or dibenzothiophene) substituted with a phenyl group at the 7-position has the property of bringing the molecular spacing between the hole characteristic compound and the electron characteristic compound closer. Specifically, the LUMO of the hole characteristic compound and the LUMO of the electron characteristic compound are closely arranged, so that the LUMO of the electron characteristic compound extends to the LUMO of the hole characteristic compound, and it can be advantageously deposited for electron transport. Due to the above structural arrangement, the low drive / high efficiency characteristics of the organic light-emitting diode applied thereto can be achieved.

[0096] In addition, when dibenzofuran (or dibenzothiophene) is substituted with a phenyl group at the 7-position, compared with substituting a phenyl group at other positions, it has the highest energy in terms of the bond dissociation energy (BDE) of the C-N bond, thus generating the most stable bonding structure. Therefore, due to its high structural stability, it has high heat resistance and can exhibit long-life characteristics.

[0097] Specifically, by using it together with the above-mentioned first compound, the charge balance is appropriately maintained, which is beneficial to exciton formation and thus enables the achievement of high-efficiency device characteristics.

[0098] In Chemical Formula 2, when m1 is 2 or greater, each R 9 may be the same as or different from each other.

[0099] In Chemical Formula 2, when m2 is 2 or greater, each R 10 may be the same as or different from each other.

[0100] In Chemical Formula 2, when m3 is 2 or greater, each R 11 may be the same as or different from each other.

[0101] In Chemical Formula 2, when m4 is 2 or greater, each R 12 may be the same as or different from each other.

[0102] In Chemical Formula 2, when m5 is 2 or greater, each R 13 may be the same as or different from each other.

[0103] In Chemical Formula 2, when m6 is 2 or greater, each R 14 may be the same as or different from each other.

[0104] In Chemical Formula 2, when m7 is 2 or greater, each R 15They may be the same as or different from each other.

[0105] For example, the second compound may be represented by any one of Chemical Formulas 2-1 to 2-4.

[0106]

[0107]

[0108] In Chemical Formulas 2-1 to 2-4, X 1 , Ar 3 , R 9 to R 15 and the definitions of m1 to m7 are the same as those described above.

[0109] As a specific example, Chemical Formula 2-1 may be represented by any one of Chemical Formulas 2-1-1 to 2-1-16.

[0110]

[0111]

[0112]

[0113] In Chemical Formulas 2-1-1 to 2-1-16, X 1 , Ar 3 , R 9 to R 15 and the definitions of m1 to m7 are the same as those described above.

[0114] As a specific example, Chemical Formula 2-2 may be represented by any one of Chemical Formulas 2-2-1 to 2-2-16.

[0115]

[0116]

[0117] In Chemical Formulas 2-2-1 to 2-2-16, X 1 , Ar 3 , R 9 to R 15 and the definitions of m1 to m7 are the same as those described above.

[0118] As a specific example, the above Chemical Formula 2-3 may be represented by any one of Chemical Formulas 2-3-1 to 2-3-16.

[0119]

[0120]

[0121] In Chemical Formulas 2-3-1 to 2-3-16, X 1 , Ar 3 , R 9 to R 15 and m1 to m7 are defined as above.

[0122] As a specific example, Chemical Formula 2-4 can be represented by any one of Chemical Formulas 2-4-1 to 2-4-16.

[0123]

[0124] [[ID=…]]

[0125] In Chemical Formulas 2-4-1 to 2-4-16, X 1 , Ar 3 , R 9 to R 15 and m1 to m7 are defined as above.

[0126] For example, the second compound can be represented by any one of Chemical Formulas 2-1-11, 2-2-11, 2-3-11, and 2-4-11.

[0127] For example, in Chemical Formula 2, Ar 3 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 terphenylene group, or a substituted or unsubstituted fluorenyl group.

[0128] As a specific example, in Chemical Formula 2, Ar 3 can be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0129] For example, in Chemical Formula 2, R 9 to R 12 can each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0130] As a specific example, in Chemical Formula 2, R 9 to R 12 can each independently be hydrogen, deuterium, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0131] As a more specific example, in Chemical Formula 2, R 9 to R12 Each independently may 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.

[0132] For example, in Chemical Formula 2, R 9 to R 12 Each independently may be hydrogen or deuterium.

[0133] For example, the second compound may be one selected from the compounds listed in Group 2, but is not limited thereto.

[0134] [Group 2]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] The first compound and the second compound may be included, for example, in a weight ratio of 1:99 to 99:1. Within the above range, the desired weight ratio can be adjusted using the electron transport ability of the first compound and the hole transport ability of the second compound to achieve bipolar characteristics, and thus improve efficiency and lifetime. Within the above range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20 (for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40). As a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0144] In addition to the above first compound and second compound, one or more compounds may also be included.

[0145] The composition for an organic optoelectronic device described above may also include a dopant.

[0146] The dopant can be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, and can be, for example, a red or green phosphorescent dopant.

[0147] A dopant is a material that is mixed in a small amount with a composition for an organic optoelectronic device to cause luminescence, and can 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 can be, for example, an inorganic, organic or organo-inorganic compound, and one or more types thereof can be used.

[0148] Examples of the dopant can be phosphorescent dopants, and examples of the phosphorescent dopants can 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 can be, for example, a compound represented by Chemical Formula Z, but is not limited thereto. [[ID=X]]

[0149] [Chemical Formula Z]

[0150] L 2 MX 2

[0151] In Chemical Formula Z, M is a metal, and L 2 and X 2 are the same or different and are ligands that form a complex with M.

[0152] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, and L 2 and X 2 can be, for example, bidentate ligands.

[0153] Examples of the ligands represented by L 2 and X 2 can be selected from the chemical formulas listed in Group A, but are not limited thereto.

[0154] [Group A]

[0155]

[0156]

[0157] In Group A,

[0158] R 300 to R 302 are each independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, or a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen, and

[0159] R 303To R 324 Each 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.

[0160] The dopant according to one embodiment may be an iridium complex and may be represented, for example, by Chemical Formula IV-1 or Chemical Formula IV-2.

[0161] [Chemical Formula IV-1]

[0162]

[0163] In Chemical Formula IV-1,

[0164] 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 ,

[0165] R 132 To R 134 Each independently is a substituted or unsubstituted C1-C6 alkyl group,

[0166] R 101 To R 116 At least one of them is a functional group represented by Chemical Formula IV,

[0167] 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

[0168] n1 and n2 each independently is any one of integers from 0 to 3, and n1 + n2 is any one of integers from 1 to 3,

[0169] [Chemical Formula IV]

[0170]

[0171] In Chemical Formula IV,

[0172] R 135 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

[0173] * refers to the moiety attached to the carbon atom.

[0174] [Chemical Formula IV-2]

[0175]

[0176] In Chemical Formula IV-2,

[0177] 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 ,

[0178] R 133 to R 135 are each independently a substituted or unsubstituted C1-C6 alkyl group,

[0179] 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

[0180] 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.

[0181] The dopant according to another embodiment may be a platinum complex and may be represented, for example, by Chemical Formula Z-1.

[0182] [Chemical Formula Z-1]

[0183]

[0184] In Chemical Formula Z-1, rings A, B, C, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0185] R A 、R B 、R C and R D are each independently mono-, di-, tri- or tetra-substituted or unsubstituted;

[0186] L B 、L Cand L D each independently is a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, or a combination thereof,

[0187] 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;

[0188] R A 、R B 、R C 、R D 、R and R′ each independently is hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, 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.

[0189] The dopant according to one embodiment can be a platinum complex and can be represented, for example, by Chemical Formula V-1 or Chemical Formula V-2.

[0190]

[0191]

[0192] In Chemical Formula V-1 and Chemical Formula V-2,

[0193] X 100 is selected from O, S, and NR 131 ,

[0194] R 117 to R 131 each independently is hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C20 aryl, or -SiR 132 R133 R 134 ,

[0195] R 132 to R 134 each independently is a substituted or unsubstituted C1 to C6 alkyl group, and

[0196] R 117 to R 131 at least one of 132 R 133 R 134 or tert-butyl group.

[0197] Hereinafter, an organic optoelectronic device including the above-described composition for an organic optoelectronic device is described.

[0198] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy (and vice versa), such as an organic optoelectronic device, an organic light-emitting diode, an organic solar cell, or an organic photosensitive drum.

[0199] In this document, an organic light-emitting diode as an example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0200] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0201] Referring to Figure 1 , an organic light-emitting diode 100 according to an 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.

[0202] The anode 120 may be made of a conductor having a large work function to assist hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, 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 is not limited thereto.

[0203] 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 be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc. or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but not limited thereto.

[0204] The organic layer 105 can contain the above-described composition for an organic optoelectronic device.

[0205] The organic layer 105 can include a light-emitting layer 130, and the light-emitting layer 130 can contain the above-described composition for an organic optoelectronic device.

[0206] The composition for an organic optoelectronic device further containing a dopant can be, for example, a green light emitting composition.

[0207] The light-emitting layer 130 can contain, for example, the above-described composition for an organic optoelectronic device as a phosphorescent host.

[0208] In addition to the light-emitting layer, the organic layer can further include a charge transport region.

[0209] The charge transport region can be, for example, a hole transport region 140.

[0210] 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.

[0211] Specifically, the hole transport region 140 can include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport assisting 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 assisting layer can contain at least one of the compounds listed in Group B.

[0212] [Group B]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218] (Dn represents the number of deuterium atom substitutions and indicates a structure substituted with one or more deuterium atoms.)

[0219] 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.

[0220] In addition, the charge transport region may be, for example, the electron transport region 150.

[0221] 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.

[0222] 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 compound in Group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0223] [Group C]

[0224]

[0225]

[0226]

[0227]

[0228] One embodiment may be an organic light - emitting diode including a light - emitting layer as an organic layer.

[0229] Another embodiment may be an organic light - emitting diode including a light - emitting layer and a hole transport region as organic layers.

[0230] Another embodiment may be an organic light - emitting diode including a light - emitting layer and an electron transport region as organic layers.

[0231] In addition to the light - emitting layer 130, the organic light - emitting diode according to one embodiment further includes a hole transport region 140 and an electron transport region 150 as organic layers 105, as Figure 1 shown.

[0232] 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.

[0233] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0234] Organic light emitting diodes can be applied to organic light emitting display devices.

[0235] While the invention has been described in connection with what are presently considered to be practical embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0236] Invention Mode

[0237] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0238] (Synthesis of the First Compound)

[0239] Synthesis Example 1: Synthesis of Compound A-1

[0240] [Reaction formula 1]

[0241]

[0242] Step 1: Synthesis of Intermediate int-19

[0243] 3-phenyl-9H-carbazole (30g, 123.3mmol), 1-bromo-4-chlorobenzene (23.6g, 123.3mmol), sodium tert-butoxide (23.7g, 246.6mmol), tri-tert-butylphosphine (2.5g, 12.3mmol) and Pd2(dba)3(5.6g, 6.2mmol) are added in a round-bottom flask, dissolved in xylene (600ml), and stirred at reflux for 8 hours at 150°C. When the reaction is complete, after removing salt by filtration, the filtrate thus obtained is adsorbed. Column chromatography (hexane:DCM (25%)) is used to obtain 28.4g (65%) of intermediate int-19.

[0244] Step 2: Synthesis of Intermediate int-20

[0245] The intermediate int-19 (28 g, 79.1 mmol), bis(pinacolato)diboron (24.1 g, 94.9 mmol), tricyclohexylphosphine (3.8 g, 15.8 mmol), potassium acetate (15.5 g, 158.3 mmol), and Pd(dppf)Cl2 (1.9 g, 2.4 mmol) were added to a round-bottom flask and dissolved in 250 ml of xylene. The mixture was stirred and refluxed at 120 °C for 8 hours. When the reaction was completed, it was cooled to room temperature, and after removing the salts by filtration, an excess of DCM and distilled water were added thereto for extraction. 20.4 g (82%) of the intermediate int-20 was obtained using column chromatography (hexane:DCM (30%)).

[0246] Step 3: Synthesis of Compound A-1

[0247] 2-Chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (14.1 g, 41.0 mmol), intermediate int-20 (20.1 g, 45.1 mmol), K2CO3 (11.3 g, 82.0 mmol), and Pd(PPh3)4 (2.4 g, 2.1 mmol) were added to a round-bottom flask, dissolved in THF (200 ml) and distilled water (40 ml), and stirred and refluxed at 70 °C for 12 hours. After the reaction was completed, the solid was separated by filtration and recrystallized with monochlorobenzene to obtain 18.5 g (72%) of compound A-1.

[0248] Synthesis Example 2: Synthesis of Compound A-27

[0249] [Reaction Formula 2]

[0250]

[0251] Step 1: Synthesis of Intermediate int-21

[0252] 2,4-Bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (40 g, 95.3 mmol), 4-chloro-2-fluorobenzeneboronic acid (15.8 g, 90.5 mmol), K2CO3 (26.3 g, 190.5 mmol), and Pd(PPh3)4 (5.5 g, 4.8 mmol) were added to a round-bottom flask, dissolved in THF (320 ml) and distilled water (100 ml), and stirred and refluxed at 70 °C for 12 hours. After the reaction was completed, the precipitated solid was filtered, and then silica hot filtration was carried out using monochlorobenzene. The filtrate was distilled under reduced pressure and recrystallized with monochlorobenzene to obtain 38.6 g (83%) of the intermediate int-21.

[0253] Step 2: Synthesis of Intermediate int-22

[0254] The intermediate int-21 (21.7g, 42.2mmol), phenylboronic acid (15.4g, 126.7mmol), Cs2CO3 (27.5g, 84.4mmol), tri-tert-butylphosphine (1.7g, 8.4mmol) and Pd2(dba)3 (1.9g, 2.1mmol) are added to a round-bottom flask, dissolved in 1,4-dioxane (200ml), and stirred at reflux for 8 hours at 120°C. When the reaction is complete, excess distilled water is added to the reactant, followed by stirring for 30 minutes, and the solid precipitated therein is filtered. After hot silica filtration using monochlorobenzene, the filtrate is distilled under reduced pressure and recrystallized with monochlorobenzene to obtain 22.1g (94%) of the intermediate int-22.

[0255] Step 3: Synthesis of Compound A-27

[0256] Intermediate int-22 (22.1 g, 39.8 mmol), 9H-carbazole (8.0 g, 47.7 mmol) and K 3 PO 4 (16.9 g, 79.6 mmol) were added to a round-bottom flask, dissolved in DMF (120 ml), and stirred at reflux for 4 hours at 150 ° C. When the reaction was complete, the reactant was slowly added to excess water in a dropwise manner to precipitate a solid, and the solid was filtered. Column chromatography (hexane: DCM (30%)) was used to obtain 24.6 g (88%) of compound A-27.

[0257] (Synthesis of the Second Compound)

[0258] Synthesis Example 3: Synthesis of Compound B-106

[0259] [Reaction formula 3]

[0260]

[0261] Step 1: Synthesis of Intermediate int-01

[0262] 4-Bromo-3-fluoro-1,1'-biphenyl (20g, 79.7mmol), (3-chloro-2-methoxyphenyl) boronic acid (16.3g, 87.6mmol), K2CO3 (22.1g, 159.3mmol) and Pd(PPh3)4 (4.6g, 4.0mmol) were added to a round-bottom flask, dissolved in 320ml THF and 80ml distilled water, and then stirred at 70°C for 8 hours. When the reaction was complete, the resultant was cooled to room temperature, filtered to remove salts, and then extracted by adding excess DCM and distilled water thereto. 24.7g (99%) of intermediate int-01 were obtained by column chromatography (hexane: DCM 30%).

[0263] Step 2: Synthesis of Intermediate int-02

[0264] The intermediate int-01 (23.7 g, 75.8 mmol) and pyridine hydrochloride (52.5 g, 454.6 mmol) were added to a round-bottom flask, and then stirred and refluxed at 200 °C for 24 hours. When the reaction was completed, the resulting product was cooled to room temperature, slowly poured into distilled water, and then stirred for 1 hour. The solid was filtered therefrom to obtain 22.6 g (100%) of the intermediate int-02.

[0265] Step 3: Synthesis of Intermediate int-03

[0266] The intermediate int-02 (21 g, 70.3 mmol) and K2CO3 (19.4 g, 140.6 mmol) were added to a round-bottom flask, dissolved in 100 ml of NMP, and then stirred and refluxed at 180 °C for 12 hours. When the reaction was completed, the mixture was poured into an excess of distilled water. The solid was filtered therefrom, dissolved in ethyl acetate, and dried over MgSO4, and then the organic layer was removed under reduced pressure therefrom. 13.8 g (70%) of the intermediate int-03 was obtained thereby by column chromatography (hexane:DCM (20%)).

[0267] Step 4: Synthesis of Compound B-106

[0268] The intermediate int-03 (13 g, 46.6 mmol), 9-phenyl-3,3'-bicarbazole (19.1 g, 46.6 mmol), sodium tert-butoxide (8.9 g, 93.2 mmol), SPhos (1.9 g, 4.7 mmol), and Pd2(dba)3 (2.1 g, 2.3 mmol) were added to a round-bottom flask, dissolved in 150 ml of xylene, and then stirred and refluxed at 150 °C for 6 hours. When the reaction was completed, the resulting product was filtered to remove salts, and the filtrate thus obtained was adsorbed on silica gel. 22.8 g (75%) of the compound B-106 was obtained by using column chromatography (hexane:DCM (30%)).

[0269] Synthesis Example 4: Synthesis of Compound B-36

[0270] [Reaction Scheme 4]

[0271]

[0272] Step 1: Synthesis of Intermediate int-04

[0273] 4-Bromo-3-fluoro-1,1'-biphenyl (20 g, 79.7 mmol), (5-chloro-2-methoxyphenyl)boronic acid (16.3 g, 87.6 mmol), K2CO3 (22.1 g, 159.3 mmol) and Pd(PPh3)4 (4.6 g, 4.0 mmol) were added to a round-bottom flask, dissolved in 320 ml of THF and 80 ml of distilled water, and then stirred under reflux at 70 °C for 8 hours. When the reaction was completed, the resulting mixture was cooled to room temperature and filtered to remove salts, and excess DCM and distilled water were added thereto for extraction. 20.8 g (85%) of intermediate int-04 was obtained by column chromatography (hexane:DCM (30%)).

[0274] Step 2: Synthesis of Intermediate int-05

[0275] Intermediate int-04 (20.8 g, 66.5 mmol) and pyridine hydrochloride (46.1 g, 399.0 mmol) were added to a round-bottom flask, and then stirred under reflux at 200 °C for 24 hours. When the reaction was completed, the resulting mixture was cooled to room temperature, slowly poured into distilled water, and then stirred for 1 hour. The solid was filtered therefrom to obtain 18.1 g (91%) of intermediate int-05.

[0276] Step 3: Synthesis of Intermediate int-06

[0277] Intermediate int-05 (18.1 g, 60.6 mmol) and K2CO3 (16.8 g, 121.2 mmol) were added to a round-bottom flask, dissolved in 80 ml of NMP, and then stirred under reflux at 180 °C for 12 hours. When the reaction was completed, the mixture was poured into excess distilled water. The solid was filtered therefrom, dissolved in ethyl acetate, and dried over MgSO4, and then the organic layer was removed under reduced pressure. 16.1 g (95%) of intermediate int-06 was obtained by column chromatography (hexane:DCM (20%)).

[0278] Step 4: Synthesis of Compound B-36

[0279] Intermediate int-06 (16.1 g, 57.8 mmol), 9-phenyl-3,3'-bicarbazole (23.6 g, 57.8 mmol), sodium tert-butoxide (11.1 g, 115.5 mmol), SPhos (2.4 g, 5.8 mmol) and Pd2(dba)3 (2.6 g, 2.9 mmol) were added to a round-bottom flask and dissolved in 200 ml of xylene, and then stirred under reflux at 150 °C for 6 hours. When the reaction was completed, the resulting mixture was filtered to remove salts, and then the filtrate thus obtained was adsorbed on silica gel. 25.6 g (68%) of compound B-36 was obtained by column chromatography (hexane:DCM (30%)).

[0280] Comparative Synthesis Example 1: Synthesis of Compound C-1

[0281]

[0282] Compound C-1 was synthesized by referring to the synthesis method known from the registered patent number KR 1849747 B1.

[0283] Comparative Synthesis Example 2: Synthesis of Compound C-2

[0284] [Reaction Scheme 5]

[0285]

[0286] Step 1: Synthesis of Intermediate int-23

[0287] 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 added to a round-bottom flask, dissolved in 600 ml of THF and 150 ml of distilled water, and then stirred under reflux 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 using column chromatography (hexane:DCM (15%)).

[0288] Step 2: Synthesis of Intermediate int-24

[0289] 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 added to a round-bottom flask, dissolved in 400 ml of THF and 100 ml of distilled water, and then stirred under reflux at 70 °C for 8 hours. When the reaction was completed, after removing the aqueous layer, 24.4 g (67%) of intermediate int-24 was obtained thereby by using column chromatography (hexane:DCM (30%)).

[0290] Step 3: Synthesis of Intermediate int-25

[0291] The 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 added to a round-bottom flask and dissolved in 250 ml of xylene. The mixture was stirred and refluxed at 150 °C for 8 hours. When the reaction was completed, the resulting product was cooled to room temperature, filtered to remove salts, and then extracted by adding an excess of DCM and distilled water thereto. 23.6 g (78%) of the intermediate int-25 was obtained by using column chromatography (hexane:DCM (40%)).

[0292] Step 4: Synthesis of Intermediate int-26

[0293] 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 added to a round-bottom flask, dissolved in 250 ml of toluene and 90 ml of distilled water, and then stirred at 60 °C for 6 hours. When the reaction was completed, after separating the aqueous layer by using a separatory funnel, the resulting organic layer was distilled under reduced pressure. The resulting product was dissolved by heating with monochlorobenzene, filtered through silica, and recrystallized to obtain 14.4 g (48%) of the intermediate int-26.

[0294] Step 5: Synthesis of Compound C-2

[0295] The intermediate int-26 (14.1 g, 39.4 mmol), the 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 added to a round-bottom flask, dissolved in 200 ml of THF and 40 ml of distilled water, and then stirred and refluxed at 70 °C for 8 hours. When the reaction was completed, after removing the aqueous layer, the solid extracted therein was filtered. The solid was dissolved by heating with monochlorobenzene, filtered through silica, and then recrystallized to obtain 18.2 g (72%) of compound C-2.

[0296] Comparative Synthesis Example 3: Synthesis of Compound C-3

[0297] [Reaction Scheme 6]

[0298]

[0299] Step 1: Synthesis of Intermediate int-27

[0300] 2-bromo-4-chlorodibenzofuran (30.3g, 107.6mmol), 9H-carbazole (18.0g, 107.6mmol), sodium tert-butoxide (20.7g, 215.3mmol), tri-tert-butylphosphine (2.2g, 10.8mmol) and Pd2(dba)3(4.9g, 5.4mmol) are added in a round-bottom flask, dissolved in 550ml of dimethylbenzene, then stirred at 150°C for 8 hours. When the reaction is complete, after removing salt by filtration, the filtrate thus obtained is adsorbed. By using column chromatography (hexane:DCM (40%)), 21.4g (54%) of intermediate int-27 are obtained.

[0301] Step 2: Synthesis of Intermediate int-28

[0302] By intermediate int-27 (21.2g, 57.6mmol), bis-boronic acid pinacol ester (17.6g, 69.2mmol), tricyclohexylphosphine (2.8g, 11.5mmol), potassium acetate (11.3g, 115.3mmol) and Pd2(dba)3(1.6g, 1.7mmol) are added in a round-bottom flask and dissolved in 200ml of dimethylbenzene.The mixture is stirred and refluxed at 160 DEG C for 8 hours.When the reaction is complete, gained is cooled to room temperature, filtered to remove salt, then extracted by adding excessive DCM and distilled water thereto.By using column chromatography (hexane:DCM (40%)) obtain 23.3g (88%) of intermediate int-28.

[0303] Step 3: Synthesis of Compound C-3

[0304] 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 added to a round-bottom flask, dissolved in 150 ml of THF and 40 ml of distilled water, and then stirred and refluxed at 70°C for 12 hours. When the reaction was completed, the solid was separated therefrom by filtration and recrystallization with monochlorobenzene to obtain 18.1 g (72%) of compound C-3.

[0305] Comparative Synthesis Example 4: Synthesis of Compound C-4

[0306]

[0307] Compound C-4 was synthesized by referring to the known synthesis method in Patent Publication No. CN 114075204 A.

[0308] Comparative Synthesis Example 5: Synthesis of Compound C-5

[0309]

[0310] Compound C-5 was synthesized by referring to the synthesis method known from the registered patent number KR 2322795 B1.

[0311] Comparative Synthesis Example 6: Synthesis of Compound C-6

[0312] [Reaction Scheme 7]

[0313]

[0314] Step 1: Synthesis of Intermediate int-29

[0315] The intermediate int-29 was synthesized by referring to the synthesis method disclosed in the registered patent number KR 1862881 B1.

[0316] Step 2: Synthesis of Compound C-6

[0317] Compound C-6 was synthesized using the same method as in Step 4 of Synthesis Example 4.

[0318] Comparative Synthesis Example 7: Synthesis of Compound C-7

[0319] [Reaction Scheme 8]

[0320]

[0321] Step 1: Synthesis of Intermediate int-30

[0322] The intermediate int-30 was synthesized by referring to the synthesis method disclosed in the published patent application WO 2017-100967 A1.

[0323] Step 2: Synthesis of Compound C-7

[0324] Compound C-7 was synthesized using the same method as in Step 4 of Synthesis Example 4.

[0325] Comparative Synthesis Example 8: Synthesis of Compound C-8

[0326]

[0327] Compound C-8 was synthesized by referring to the synthesis method known from the registered patent number KR 2290362 B1.

[0328] Comparative Synthesis Example 9: Synthesis of Compound C-9

[0329]

[0330] Compound C-9 was synthesized by referring to the synthesis method known from the registered patent number KR 2247294 B1.

[0331] Comparative Synthesis Example 10: Synthesis of Compound C-10

[0332]

[0333] Compound C-10 was synthesized by referring to the synthesis method known from the published patent application KR 2021-0152819.

[0334] (Manufacture of Organic Light-Emitting Diodes)

[0335] Example 1

[0336] A glass substrate coated with ITO (indium tin oxide) was cleaned with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with solvents such as isopropyl alcohol, acetone, methanol, etc. and dried, then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred to a vacuum depositor. The obtained ITO transparent electrode was used as the anode, and Compound A doped with 3% NDP-9 (obtainable from Novaled) was vacuum-deposited on the ITO substrate to form a thick hole injection layer, and Compound A was deposited on the hole injection layer to form a thick hole transport layer. Compound B was deposited on the hole transport layer to a thickness of to form a hole transport auxiliary layer. On the hole transport auxiliary layer, Compound A-1 synthesized in Synthesis Example 1 and Compound B-36 synthesized in Synthesis Example 4 with a weight ratio of 3:7 were used as hosts simultaneously, and 10 wt% of PhGD was doped as a dopant to form a thick light-emitting layer by vacuum deposition. Then, Compound C was deposited on the light-emitting layer to form a thick electron transport auxiliary layer, and Compound D and LiQ were vacuum-deposited simultaneously with a weight ratio of 1:1 to form a thick electron transport layer. LiQ and Al were vacuum-deposited sequentially on the electron transport layer to form a cathode, thereby manufacturing an organic light-emitting diode.

[0337] The organic light-emitting diode has the following structure: ITO / Compound A (doped with 3% NDP-9, ) / Compound A / Compound B / EML [90 wt% host (Compound A-1:Compound B-36 = 3:7 w / w):10 wt% PhGD] / Compound C / Compound D: LiQ / LiQ / Al

[0338] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0339] Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0340] Compound C: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0341] Compound D: 2-(biphenyl-4-yl)-4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine

[0342] [PhGD]

[0343]

[0344] Examples 2 to 4 and Comparative Examples 1 to 10

[0345] The diodes of Examples 2 to 4 and Comparative Examples 1 to 10 were fabricated in the same manner as in Example 1, except that the host was changed as described in Table 1.

[0346] Evaluation

[0347] (1) Measure the change in current density according to the voltage change

[0348] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit diode 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.

[0349] (2) Measure the change in luminance according to the voltage change

[0350] 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).

[0351] (3) Measure the luminous efficiency

[0352] The luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated using the luminance and current density measured according to (1) and (2) above.

[0353] The luminous efficiency ratios of Examples 1 to 4 and Comparative Examples 1 to 10 were calculated as relative values based on Comparative Example 1 and are shown in Table 1.

[0354] (4) Measuring the driving voltage

[0355] The driving voltage of each diode at 15 mA / cm² was measured using a current-voltage meter (Keithley 2400) to obtain the results. 2 to obtain the results.

[0356] The driving voltage ratios of Examples 1 to 4 and Comparative Examples 1 to 10 were calculated as relative values based on Comparative Example 1 and are shown in Table 1.

[0357] [Table 1]

[0358]

[0359]

[0360] Referring to Table 1, compared with the organic light-emitting diodes according to Comparative Examples 1 to 10, the organic light-emitting diodes according to Examples 1 to 4 have significantly improved luminous efficiency while maintaining comparable or lower driving voltages.

[0361] Although the present invention has been described in connection with presently considered practical embodiments, it should be understood that the present invention is not limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

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] In Chemical Formula 1, Z 1 to Z 3 each independently is N or C-R a , Z 1 from Z 3 at least two of which are N, L 1 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6 - C30 aryl, and R a and R 1 to R 8 each independently is hydrogen, deuterium, a substituted or unsubstituted C1 - C10 alkyl, a substituted or unsubstituted C6 - C30 aryl, a substituted or unsubstituted C2 - C30 heterocyclic group, or a combination thereof; [Chemical Formula 2] In Chemical Formula 2, X 1 is O or S, Ar 3 is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof, R 9 to R 12 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R 13 to R 15 each independently is hydrogen, deuterium or a substituted or unsubstituted phenyl group, m2, m3, m5, and m6 are each independently one of the integers from 1 to 3, m1 and m4 are each independently one of the integers from 1 to 4, and m7 is one of the integers from 1 to 5.

2. The composition for an organic optoelectronic device according to claim 1, In Chemical Formula 1, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted fluorenyl group.

3. The composition for an organic optoelectronic device according to claim 1, In Chemical Formula 1, R 1 to R 8 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heterocyclic group.

4. The composition for an organic optoelectronic device according to claim 1, wherein the second compound is represented by any one of Chemical Formulas 2-1 to 2-4: In Chemical Formulas 2-1 to 2-4, X 1 , Ar 3 , R 9 to R 15 and m1 to m7 are as defined in claim 1.

5. The composition for an organic optoelectronic device according to claim 4, wherein the second compound is represented by any one of Chemical Formulas 2-1-11, 2-2-11, 2-3-11, and 2-4-11: 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 3 , R 9 to R 15 and m1 to m7 are as defined in claim 1.

6. The composition for an organic optoelectronic device according to claim 1, In Chemical Formula 2, Ar 3 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 terrylene group, or a substituted or unsubstituted fluorenyl group.

7. The composition for an organic optoelectronic device according to claim 1, wherein the first compound is selected from the compounds listed in Group 1, and the second compound is selected from the compounds listed in Group 2: [Group 1] 8. An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer contains the composition for an organic optoelectronic device according to any one of claims 1 to 7.

9. The organic optoelectronic device according to claim 8, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the composition for an organic optoelectronic device.

10. The organic optoelectronic device according to claim 9, wherein the composition for an organic optoelectronic device further comprises a phosphorescent dopant.

11. The organic optoelectronic device according to claim 10, wherein the composition for an organic optoelectronic device is a green light-emitting composition.

12. A display device, comprising the organic optoelectronic device according to claim 9.

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