An organometallic complex and an organic optoelectronic device containing the same

Abstract

The present invention provides an organometallic complex and an organic optoelectronic device comprising the same, particularly an organic light-emitting diode, wherein the structure of the organometallic complex is shown in Formula I: M is selected from platinum (Pt) or palladium (Pd); detailed information about the organometallic complex and the organic optoelectronic device can be understood through the specific description provided herein. The organometallic compound provided by the present invention can obtain high-efficiency and long-life blue or blue-green light-emitting OLED devices, demonstrating the potential application of such organometallic complexes in blue or blue-green light-emitting OLEDs. Platinum and palladium metals are abundant in the earth's crust, and can replace the rare metal iridium to form sustainable organometallic complexes, having good commercial application prospects.

Description

Technical Field

[0001] The present invention belongs to the field of organic optoelectronics, and particularly relates to an organometallic complex and an organic optoelectronic device comprising the same, especially an organic light-emitting diode. Background Art

[0002] As a new type of display technology, organic light-emitting diodes (OLEDs) have unique advantages such as self-luminescence, wide viewing angle, low power consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, and can be used to fabricate flexible, bendable and transparent display panels as well as being environmentally friendly. They can be applied in flat panel displays and new generation lighting, and can also be used as the backlight of LCDs.

[0003] OLED emission is divided into two modes: fluorescence emission and phosphorescence emission. According to theoretical speculation, the ratio of singlet excited state to triplet excited state caused by the combination of charges is 1:3. In 1998, Professors Baldo and Forrest et al. found that triplet phosphorescence can be utilized at room temperature, and the upper limit of the original internal quantum efficiency was increased to 100%. Triplet phosphors are often heavy metal atoms that form complexes. Utilizing the heavy atom effect, strong spin-orbit coupling causes the energy levels of the singlet excited state and the triplet excited state to mix with each other, enabling the originally forbidden triplet energy to be released in the form of phosphorescence, and the quantum efficiency is also greatly improved.

[0004] Currently, almost all of the light-emitting layers in OLED components use the host-guest light-emitting system structure, that is, a guest light-emitting material is doped in a host material. Generally speaking, the energy system of the organic host material is larger than that of the guest material, that is, energy is transferred from the host to the guest, causing the guest material to be excited and emit light. Commonly used phosphorescent organic host materials such as CBP (4,4'-bis(carbazol-9-yl)biphenyl) have high efficiency and high triplet energy levels. When used as an organic material, the triplet energy can effectively transfer from the light-emitting organic material to the guest phosphorescent material. Commonly used organic guest materials are iridium metal compounds. Currently, the application of iridium metal compounds in commercial OLED materials has become the mainstream. However, iridium metal is very expensive and scarce in the earth's crust, and it is necessary to study an organometallic complex to replace the expensive iridium metal complex, expand the alternative options for OLED light-emitting materials, and provide the possibility for sustainable development.

[0005] The present invention discovers an organometallic compound (Pt or Pd). Introducing specific cyclic structures, substituents, etc. can improve the luminescence efficiency of the organometallic compound, ensuring that the organometallic compound has high luminescence characteristics. When applied to organic optoelectronic devices, especially in organic light-emitting devices, high current efficiency and reduced operating voltage of the components can be obtained. Summary of the Invention

[0006] The object of the present invention is to provide an organometallic complex and an optoelectronic device comprising the same, in particular an organic light-emitting diode.

[0007] An organometallic complex provided by the present invention has a structure as shown in formula (I):

[0008]

[0009] wherein M is Pt or Pd, X1 to X13 are CR5 or N; Y is N, CR5, SiR5 or B; L2 is independently selected from one of O, S, NR1, CR1R2, SiR1R2, O=P-R1 or B-R1; L1 and L3 do not exist, or are independently selected from one of a single bond, O, S, NR1, CR1R2, SiR1R2, O=P-R1 or B-R1; R1 to R5 are independently selected from hydrogen, deuterium, CN, halogen, C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylsilyl-containing, C1-C60 alkoxysilyl-containing, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C1-C60 heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted arylamino group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted aryloxysilyl group, substituted or unsubstituted arylacyl group, substituted or unsubstituted heteroarylacyl group, substituted or unsubstituted phosphoryl group; heteroaryl means containing at least one heteroatom of B, N, O, S, P(=O), Si, P; wherein X1 to X14 can form a ring with adjacent groups; when R1 to R5 are two or more, they can be the same or different, and all groups can be partially deuterated or fully deuterated, and can be partially fluorinated or fully fluorinated.

[0010] Preferably, for the organometallic complex of the present invention, two atoms connected to the metal M form covalent bonds, and two form coordination bonds, so that the organometallic complex is in a neutral state.

[0011] Preferably, for the organometallic complex of the present invention, formula I is selected from one of the following structures:

[0012]

[0013]

[0014] wherein, X1 to X14, Y, M, L3, R1 to R5 are the same as above.

[0015] Preferably, for the organometallic complex of the present invention, formula I is selected from one of the following structures:

[0016]

[0017] Among them, X1 to X14, Y, M, L3, R1 to R6 are the same as above. When there are two or more of R1 to R6, they can be the same or different, and n is 0, 1, 2, 3, or 4.

[0018] Preferably, for the organometallic complex of the present invention, in formula (I), The parts independently selected from one of the following representative groups, but not limited thereto:

[0019]

[0020] Among them, X15 to X18 are defined the same as X1 in claim 1, and R1 to R7 are defined the same as the definition in claim 1.

[0021] Preferably, for the organometallic complex of the present invention, any two in formula (I) are bonded together to form a fused ring system, and the fused ring system is benzimidazole, benzoxazole, benzothiazole, indazole, quinoline, isoquinoline, imidazo[1,5-a]pyridine, etc.

[0022] Preferably, for the organometallic complex of the present invention, R1 to R7 in formula (I) are selected from one of the following structures, but not limited thereto:

[0023]

[0024] In the above structures, they can be partially deuterated or fully deuterated, and can be partially fluorinated or fully fluorinated.

[0025] Preferably, for the organometallic complex of the present invention, formula (I) is selected from one of the following representative structures, but not limited thereto:

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[0072] Preferably, for the organometallic complex of the present invention, when M is Pd in Formula I, Pt in the above structure can be replaced by Pd, but this is not meant to be limiting.

[0073] The present invention relates to an organometallic complex comprising the compound of formula (I) and one or more formulations formed with a solvent. The solvent used is not particularly limited, and unsaturated hydrocarbon solvents well-known to those skilled in the art such as toluene, xylene, mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc., halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc., halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc., ether solvents such as tetrahydrofuran, tetrahydropyran, etc., and ester solvents such as alkyl benzoates can be used.

[0074] The present invention also relates to an organic optoelectronic device,

[0075] comprising: a first electrode; a second electrode facing the first electrode; and an organic functional layer interposed between the first electrode and the second electrode;

[0076] wherein the organic functional layer contains the organometallic complex.

[0077] The organic optoelectronic device described in the present invention is any one of an organic photovoltaic device, an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC), an organic thin-film transistor (OTFT), an organic memory device (Organic Memory Element), a lighting device, and a display device.

[0078] The present invention also relates to an organic electroluminescent device, comprising a cathode layer, an anode layer, and an organic layer, where the organic layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron injection layer, and an electron transport layer, and the light-emitting layer of the device contains the organic metal complex described above.

[0079] The light-emitting layer of the organic electroluminescent device described in the present invention contains the organic metal complex and a corresponding host material, where the mass percentage of the organic metal complex is 0.1% - 50%.

[0080] In the present invention, for an organic optoelectronic device, an anode can be formed by sputtering coating, electron beam evaporation, vacuum evaporation, or other methods to deposit a metal or a conductive oxide and their alloys on a substrate; then, a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron transport layer are sequentially deposited on the surface of the prepared anode, and finally, a cathode is deposited. An organic electroluminescent device can also be fabricated by depositing a cathode, an organic layer, and an anode on a substrate in this order. The organic layer can also include a multi-layer structure such as a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, and an electron transport layer. In the present invention, the organic layer can be prepared by using a polymer material according to solvent engineering (such as spin-coating, tape-casting, doctor-blading, screen-printing, inkjet printing, or thermal-imaging), which can reduce the number of device layers.

[0081] The materials used in the organic electroluminescent device according to the present invention can be divided into top emission, bottom emission, or double-sided emission. The compounds of the organic electroluminescent device according to the embodiments of the present invention can be applied to organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic thin-film transistors, and other electroluminescent devices based on a principle similar to that of organic light-emitting devices.

[0082] Advantages of the present invention:

[0083] The organometallic complex involved in the present invention has high luminous efficiency. A suitable ligand structure can enhance the energy transfer between the host and the guest. Specifically, when the organometallic complex of the present invention is used as a functional layer, especially as a light-emitting layer, the fabricated organic electroluminescent device has high current efficiency and reduced turn-on voltage. This indicates that after most electrons and holes recombine, the energy is effectively transferred to the organometallic complex for luminescence, providing a novel organometallic complex with excellent luminescent properties. BRIEF DESCRIPTION OF THE DRAWINGS

[0084] Figure 1 It is a structural layer diagram of the organic optoelectronic device of the present invention.

[0085] Among them, 110 represents the substrate, 120 represents the anode, 130 represents the hole injection layer, 140 represents the hole transport layer, 150 represents the light-emitting layer or the active layer, 160 represents the hole blocking layer, 170 represents the electron transport layer, 180 represents the electron injection layer, and 190 represents the cathode. DETAILED DESCRIPTION OF THE INVENTION

[0086] In order to make the objectives, technical solutions and advantages of the present invention clearer, the following further describes the present invention in detail with reference to specific embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0087] In a preferred embodiment of the present invention, the OLED device of the present invention contains a hole transport layer, and the hole transport material can preferably be selected from known or unknown materials, particularly preferably selected from the following structures, but this does not mean that the present invention is limited to the following structures:

[0088]

[0089] In a preferred embodiment of the present invention, the hole transport layer contained in the OLED device of the present invention contains one or more p-type dopants. The preferred p-type dopants of the present invention are the following structures, but this does not mean that the present invention is limited to the following structures:

[0090]

[0091] In a preferred embodiment of the present invention, the electron transport layer can be selected from at least one of compounds ET-1 to ET-13, but this does not mean that the present invention is limited to the following structures:

[0092]

[0093] The electron transport layer can be formed by an organic material and one or more n-type dopants (such as LiQ).

[0094] The present invention also provides a formulation comprising the organometallic complex and a solvent. The solvent used is not particularly limited, and unsaturated hydrocarbon solvents well-known to those skilled in the art such as toluene, xylene, mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc., halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc., halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc., ether solvents such as tetrahydrofuran, tetrahydropyran, etc., and ester solvents such as alkyl benzoate can be used. The said formulation is directly used for preparing optoelectronic devices.

[0095] Hereinafter, according to the existing literature and the inventor's relevant technical reserves, the synthesis steps of the organometallic complex involved in formula (I) are as follows:

[0096] Example 1: Synthesis of Compound 1

[0097]

[0098] (1) Under a nitrogen atmosphere, in a round-bottom flask, after completely dissolving S-1 (10 mmol) and S-2 (11 mmol) in xylene (80 mL), potassium tert-butoxide (5 g), palladium acetate (0.1 g), and tri-tert-butylphosphine (0.2 g) were added thereto. The mixture was heated under reflux for 5 - 10 hours. After cooling to room temperature, the salts were removed by filtration through diatomaceous earth. After vacuum concentrating the solvent, purification and separation were carried out on a silica gel column using petroleum ether:dichloromethane (20:1 - 2:1) as the eluent to obtain S-3 (5.8 g, yield 85%). LC-MS, 684.3, 686.3.

[0099] (2) In a round-bottom flask, S-3 (10 mmol), imidazole (15 mmol), cuprous oxide (1.4 g), cis-2-pyridine oxime (2.4 g), and acetonitrile (200 mL) were fully mixed. After bubbling to remove oxygen, the reaction was refluxed under a nitrogen atmosphere for 48 hours. After the reaction ended, it was cooled to room temperature, the inorganic salts were removed by filtration through diatomaceous earth, and washed with dichloromethane. After adding water to the filtrate, extraction was carried out with dichloromethane. The dichloromethane layers were combined, dried, and purification and separation were carried out on a silica gel column using petroleum ether:ethyl acetate (20:1 - 2:1) as the eluent to obtain S-4 with a yield of 73%. LC-MS, 672.3.

[0100] (3) Under a nitrogen atmosphere, in a round-bottom flask, S-4 (10 mmol) was dissolved in toluene (60 mL), and then iodomethane (30 mmol) was added. The mixture was stirred at room temperature for 48 hours. After filtration, the solid was washed successively with cold toluene (20 mL) and ether (20 mL), and dried to obtain a light yellow solid S-5 with a yield of 88%. LC-MS, 687.4.

[0101] (4) Under a nitrogen atmosphere, react S-5 (5 mmol) and silver oxide (2.52 mmol) in a round-bottom flask in dichloromethane (50 mL) for 24 hours. After removing dichloromethane under reduced pressure, add Pt(COD)Cl 2 (5.1 mmol) and o-dichlorobenzene (80 mL), heat under reflux for 72 hours. After cooling to room temperature, concentrate and dry to obtain a light yellow solid. Purify and separate it on a silica gel column using petroleum ether:dichloromethane (20:1 to 2:1) as the eluent to obtain Compound 1 (yield 87%). Further purify it by vacuum sublimation. LC-MS: theoretical 879.35, measured: 879.4; elemental analysis C: 64.15; H: 5.50; N: 6.37; measured: C: 64.20; H: 5.60; N: 6.30.

[0102] Example 2: Synthesis of Compound 2

[0103]

[0104] The synthesis procedure of Compound 2 is similar to that of Compound 1. Finally, the yield of Compound 2 formed is 82%. LC-MS: theoretical 1060.47, measured: 1060.5; elemental analysis C: 69.04; H: 5.98; N: 6.60; measured: C: 69.10; H: 6.03; N: 6.51.

[0105] Example 3: Synthesis of Compound 3

[0106]

[0107] The synthesis procedure of Compound 3 is similar to that of Compound 1. Finally, the yield of Compound 3 formed is 78%. LC-MS: theoretical 1027.45, measured: 1027.4; elemental analysis C: 66.58; H: 6.27; N: 5.45; measured: C: 66.62; H: 6.33; N: 5.46.

[0108] Example 4: Synthesis of Compound 4

[0109]

[0110] The synthesis procedure of Compound 4 is similar to that of Compound 1. Finally, the yield of Compound 4 formed is 80%. LC-MS: theoretical 1011.48, measured: 1011.5; elemental analysis C: 68.82; H: 6.37; N: 5.53; measured: C: 68.78; H: 6.43; N: 5.55.

[0111] Example 5: Synthesis of Compound 5

[0112]

[0113] The synthesis procedure of Compound 5 is similar to that of Compound 1. The yield of the finally formed nickel complex is 81%. LC-MS: theoretical 998.45, measured: 998.4; Elemental analysis C: 67.31; H: 6.15; N: 7.01; measured: C: 67.36; H: 6.21; N: 6.94.

[0114] Example 6: Synthesis of Compound 6

[0115]

[0116] The synthesis procedure of Compound 6 is similar to that of Compound 1. The yield of the finally formed Compound 6 is 73%. LC-MS: theoretical 879.35, measured: 879.3; Elemental analysis C: 64.15; H: 5.50; N: 6.37; measured: C: 64.20; H: 5.60; N: 6.33.

[0117] Example 7: Synthesis of Compound 7

[0118]

[0119]

[0120] (1) Under a nitrogen atmosphere, dissolve Compound S-1 (10 mmol) in tetrahydrofuran (60 mL) in round-bottom flask 1, and cool it to -77 °C with an acetone-dry ice bath; dissolve Compound S-2 (10 mmol) in tetrahydrofuran (20 mL) in round-bottom flask 2, cool it to -77 °C with an acetone-dry ice bath, and add n-butyllithium (2.5 M solution) (4 mL), and react for 5 hours. Add the mixture in round-bottom flask 2 dropwise to round-bottom flask 1, keep the reaction temperature at -77 °C, and react for 1 hour. Slowly warm up the mixture in round-bottom flask 1 to room temperature, and continue to react for 6 hours. Quench the reaction with saturated aqueous ammonium chloride solution, and separate the organic phase. Extract the aqueous phase with ethyl acetate, combine the organic phases, concentrate, and purify and separate on a silica gel column using petroleum ether: ethyl acetate (20:1 to 2:1) as the eluent to obtain Compound S-2A (yield 76%); LC-MS: 715.3, 717.3.

[0121] (2) Dissolve compound S-2A (10 mmol) in acetic acid (100 mL), add dropwise 2 mL of concentrated sulfuric acid, and reflux the mixture for 12 hours. After concentration and cooling, pour it into ice water and extract with dichloromethane (50 mL × 2). The dichloromethane layer is washed with saturated brine and aqueous sodium bicarbonate solution, then concentrated to dryness. The crude product is purified and separated on a silica gel column using petroleum ether:dichloromethane (20:1 - 2:1) as the eluent to obtain compound S-3 (yield 73%); LC-MS: 697.3, 699.3.

[0122] (3) The remaining synthetic steps are similar to those of compound 1. Finally, the yield of compound 7 formed is 76%, LC-MS: theoretical 998.45, measured: 998.4; elemental analysis C: 68.52; H: 6.15; N: 4.21; measured: C: 68.58; H: 6.20; N: 4.24.

[0123] Example 8: Synthesis of Compound 8

[0124]

[0125] The synthetic steps of compound 8 are similar to those of compound 7. Finally, the yield of compound 8 formed is 75%, LC-MS: theoretical 1027.45, measured: 1027.5; elemental analysis C: 66.58; H: 6.27; N: 5.45; measured: C: 66.67; H: 6.37; N: 5.51.

[0126] Example 9: Synthesis of Compound 9

[0127]

[0128] The synthetic steps of compound 9 are similar to those of compound 1. Finally, the yield of compound 9 formed is 84%, LC-MS: theoretical 790.29, measured: 790.3; elemental analysis C: 71.34; H: 6.11; N: 7.08; measured: C: 71.30; H: 6.23; N: 7.00.

[0129] Example 10: Synthesis of Compound 10

[0130]

[0131] The synthetic steps of compound 10 are similar to those of compound 1. Finally, the yield of compound 10 formed is 79%, LC-MS: theoretical 971.41, measured: 971.41; elemental analysis C: 75.33; H: 6.53; N: 7.20; measured: C: 75.38; H: 6.65; N: 7.10.

[0132] Example 11: Synthesis of Compound 11

[0133]

[0134] The synthesis procedure of Compound 11 is similar to that of Compound 8. The final yield of Compound 11 is 74%. LC-MS: theoretical 938.39, measured: 938.4; elemental analysis C: 72.86; H: 6.87; N: 5.96; measured: C: 73.01; H: 6.76; N: 6.00.

[0135] General preparation method of OLED:

[0136] Evaporate p-doping materials P-1 to P-5 on the surface or anode of ITO glass with a light-emitting area of 2 mm × 2 mm, or co-evaporate this p-doping material with the compounds described in the table at a concentration of 1% to 50% to form a hole injection layer (HIL) of 5 - 100 nm and a hole transport layer (HTL) of 5 - 200 nm. Subsequently, form a light-emitting layer (EML) of 10 - 100 nm (which may contain the compounds) on the hole transport layer. Finally, sequentially form an electron transport layer (ETL) of 20 - 200 nm and a cathode of 50 - 200 nm with the compounds. If necessary, add an electron blocking layer (EBL) between the HTL and EML layers and an electron injection layer (EIL) between the ETL and the cathode to fabricate an organic light-emitting device.

[0137] OLED device examples:

[0138] The structure of the specific bottom-emitting OLED device is as follows: on the glass containing ITO, the HIL is HT-1:P-3 (95:5 v / v%), with a thickness of 10 nm; the HTL is HT-1, with a thickness of 90 nm; the EBL is HT-10, with a thickness of 10 nm, the EML is BH-1: organometallic compound (95:5 v / v%), with a thickness of 35 nm, the ETL is ET-13:LiQ (50:50 v / v%), with a thickness of 35 nm, and then the cathode Al is evaporated to 70 nm.

[0139]

[0140] According to the above device examples, the characteristics of the OLED device such as external quantum efficiency (EQE), turn-on voltage, emission peak, etc. are shown in Table 1 below.

[0141] Table 1

[0142]

[0143]

[0144] Introducing a ligand structure with a shorter conjugated chain is the main means to achieve blue light emission. In this invention, novel ligands blocked by carbon, silicon, boron, nitrogen, etc. are used to obtain novel organometallic complexes. The substituted imidazole aryl forms a complex with the metal, which determines the HOMO, LUMO, and the lowest triplet energy level of the organometallic complex in this invention, and further determines the spectral position of its excited state radiation. The organometallic compound of this invention has good luminescence properties. When used as a guest material doped into the host material BH-1, an OLED device with an external quantum efficiency of 18.4% to 23.2% is obtained. In a bottom-emitting OLED device without any light extraction means, the external quantum efficiency exceeds 20%, indicating that the organometallic complex of this invention has an internal quantum efficiency of 100% in the OLED device. At the same time, the lifetime LT90 of the device reaches up to 110 hours at most, indicating that using the compound of this invention can obtain a long-life blue phosphorescent OLED device, showing the potential application of this type of organometallic complex in blue OLEDs. Compared with the comparative compound Pt-1, the new compound obtained by incorporating cyclic structures such as carbon, silicon, boron, nitrogen, etc. into the imidazole aryl in this invention has better luminescence efficiency and spectral characteristics. For example, Device Example 1 has higher efficiency and operating lifetime than the comparative device. At the same time, the spectrum of the device is between 455 - 465 nm, and the energy transfer with the host is more effective. Especially for Compound 7 used in Device Example 7, the emission peak is at 460 nm, with an efficiency 28% higher than that of Pt-1 and the lifetime increased to 3.1 times, indicating that the organometallic compound of this invention has better commercial application prospects.

[0145] As described above, the above are only the preferred specific embodiments of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art within the technical scope disclosed by the present invention, according to the technical solution of the present invention and its inventive concept, makes equivalent substitutions or changes, and all should be covered within the protection scope of the present invention.

Claims

1. An organometallic complex, characterized in that the structural formula of the organometallic complex is as shown in Compound 1-11:

2. A preparation, characterized in that it contains the organometallic complex according to Claim 1 and at least one solvent.

3. A preparation according to Claim 2, characterized in that the solvent is selected from unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, chlorobenzene, dichlorobenzene, trichlorobenzene, tetrahydrofuran, tetrahydropyran or alkyl benzoate.

4. An organic optoelectronic device, characterized in that it includes: a first electrode; a second electrode facing the first electrode; an organic functional layer sandwiched between the first electrode and the second electrode; wherein the organic functional layer contains the organometallic complex according to Claim 1.

5. An organic optoelectronic device, characterized in that: it includes a cathode layer, an anode layer and an organic layer, and the organic layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting layer or an active layer, an electron injection layer, and an electron transport layer; any layer of the device contains the organometallic complex according to Claim 1.

6. An organic optoelectronic device according to Claim 5, characterized in that the organic optoelectronic device is an organic photovoltaic device, an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC), an organic thin-film transistor (OTFT) or an organic memory device (Organic Memory Element).

7. An organic optoelectronic device according to any one of Claims 4 to 6, characterized in that the organic optoelectronic device is an organic electroluminescent device, and the light-emitting layer contains the organometallic complex and a corresponding host material, wherein the mass percentage of the organic complex is 1% to 50%.

8. A display or lighting device, characterized in that the display or lighting device contains the organic optoelectronic device according to any one of Claims 4 to 7.

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