Binuclear platinum complex luminescent materials and their applications
By using binuclear platinum complexes as luminescent materials in OLEDs, the problems of low luminous efficiency and short lifespan are solved, and the development of efficient solution-processed devices is achieved, which has good industrialization prospects.
Patent Information
- Application Number
- CN202211510555.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-12-22
- Filing Date
- 2022-11-29
- Publication Date
- 2025-09-26
- Estimated Expiration
- 2042-11-29
AI Technical Summary
Existing OLED devices have problems with low luminous efficiency and short lifespan, especially the lagging development of high-performance metal complexes in solution-processed devices, which limits their development.
Provided is a binuclear platinum complex luminescent material, which is applied to the light-emitting layer or electron transport layer of an organic light-emitting diode. It is prepared by a solution method to improve the luminescence efficiency and device life.
It achieves high luminous efficiency and device life, has good industrialization potential, and is significantly superior to traditional materials.
Smart Images

Figure CN116041397B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the field of luminescent materials, and in particular to a class of binuclear platinum complexes and applications thereof in organic light-emitting diodes. Background Art
[0002] Organic optoelectronic devices include, but are not limited to, the following categories: organic light-emitting diodes (OLEDs), organic thin-film transistors (OTFTs), organic photovoltaics (OPVs), light-emitting electrochemical cells (LCEs), and chemical sensors.
[0003] In recent years, OLEDs, a promising lighting and display technology, have garnered widespread attention from both academia and industry. OLED devices, with their self-luminescence, wide viewing angles, fast response times, and the ability to be made flexible, have become a strong contender for next-generation display and lighting technology. However, OLEDs still face challenges such as low efficiency and a short lifespan, requiring further research.
[0004] Early fluorescent OLEDs typically only utilized singlet-state emission. The triplet excitons generated in the device could not be effectively utilized and returned to the ground state non-radiatively, limiting their widespread use. In 1998, Zhi Zhiming et al. from the University of Hong Kong first reported the phenomenon of electrophosphorescence. That same year, Thompson et al. fabricated phosphorescent OLEDs using transition metal complexes as luminescent materials. Phosphorescent OLEDs efficiently utilize both singlet and triplet excitons for emission, theoretically achieving 100% internal quantum efficiency, significantly accelerating the commercialization of OLEDs. The color of OLED emission can be manipulated through the structural design of the luminescent material. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Currently, green, yellow, and red phosphorescent materials have been commercialized. Commercial OLED displays typically utilize a combination of blue fluorescence and yellow, or green and red phosphorescence, to achieve full-color display. However, the industry urgently needs luminescent materials with higher efficiency and longer lifetimes. Metal complex luminescent materials are already widely used in the organic light-emitting display industry, but their performance, such as luminescence efficiency and excited-state lifetime, still needs to be further improved. At present, compared with vapor-deposited luminescent materials, the development of high-performance metal complexes suitable for solution-processed devices is relatively lagging, which has become an important factor restricting the development of solution-processed devices. Summary of the Invention
[0005] In view of the above problems existing in the prior art, the present invention provides a type of binuclear platinum complex luminescent material, which has good luminous efficiency and device life when applied to organic light-emitting diodes.
[0006] The present invention also provides an organic light emitting diode containing the binuclear platinum complex.
[0007] The binuclear platinum complex material is a compound having the structure of formula (I):
[0008]
[0009] in:
[0010] X1 to X 12 are each independently selected from N or CR;
[0011] A is selected from CR 1 R 2 ,NR 3 ,O,S or Se;
[0012] R, R 1 , R 2 , R 3 are each independently selected from the following groups: hydrogen, deuterium, halogen, amino, C1-C20 alkylcarbonyl, carboxyl, aldehyde, C1-C20 sulfanyl, cyano, sulfonyl, phosphino, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or any two adjacent R, R 1 , R 2 , R 3 Connected to form a ring;
[0013] The heteroatoms in the heteroaryl group are one or more of N, S, and O;
[0014] The substitution is substitution by halogen, amino, cyano, C6-C12 aryl or C1-C4 alkyl.
[0015] Preferably, R, R 1 , R 2 , R 3 Each is independently selected from the group consisting of hydrogen, deuterium, halogen, amino, C1-C6 sulfanyl, cyano, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 6 carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, and substituted or unsubstituted heteroaryl having 3 to 6 carbon atoms.
[0016] Preferably, R, R 1 , R 2 , R 3Each is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C1-C4 alkyl, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, and substituted or unsubstituted heteroaryl having 3-6 carbon atoms;
[0017] The substitution is substituted by a phenyl group or a C1-C4 alkyl group.
[0018] Preferably: A is selected from NR 3 ,O,S.
[0019] Preferably, R, R 1 , R 2 , R 3 Each is independently selected from the group consisting of hydrogen, deuterium, cyano, methyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, and substituted or unsubstituted pyrimidinyl.
[0020] Preferably, the general formula (I) is the following structure:
[0021]
[0022] R, R 3 Independently selected from the group consisting of hydrogen, deuterium, methyl, tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl.
[0023] More preferably, the general formula (I) is the following structure:
[0024]
[0025] R is selected from the group consisting of hydrogen, deuterium, methyl, tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl.
[0026] Preferably: at most one of X1 to X4 is N, and the rest are CR;
[0027] At most one of X5-X7 is N, and the rest are CR.
[0028] At most one of X8-X10 is N, and the rest are CR, X12 is CH, and X11 is N or CH.
[0029] Preferably, X1, X3, and X9 are CR, and X2, X4-X8, and X10 are CH.
[0030] Preferably: wherein R is hydrogen, deuterium, methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, pyridyl.
[0031] The following are examples of platinum metal complexes according to the present invention, but are not limited to the structures listed:
[0032]
[0033]
[0034]
[0035]
[0036] The precursor of the above metal complex, i.e. the ligand, has the following structural formula:
[0037]
[0038] Where X1 to X 12 , A is defined as above.
[0039] The present invention also provides a use of the above-mentioned platinum complex in an organic optoelectronic device, which includes, but is not limited to, an organic light emitting diode, an organic thin film transistor, an organic photovoltaic device, a light emitting electrochemical cell and a chemical sensor, preferably an organic light emitting diode.
[0040] An organic light emitting diode comprising the platinum complex, wherein the platinum complex is a luminescent material in a light emitting device.
[0041] The organic light-emitting diode of the present invention comprises a cathode, an anode and an organic layer, wherein the organic layer is one or more layers selected from the group consisting 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 not all of these organic layers need to be present; at least one of the hole injection layer, the hole transport layer, the hole blocking layer, the electron injection layer, the light-emitting layer and the electron transport layer contains the binuclear platinum complex described in formula (I).
[0042] Preferably, the layer where the platinum complex of formula (I) is located is a light-emitting layer or an electron transport layer.
[0043] The total thickness of the organic layer of the device of the present invention is 1-1000 nm, preferably 1-500 nm, more preferably 5-300 nm.
[0044] The organic layer can be formed into a thin film by evaporation or solution method.
[0045] The series of platinum complex luminescent materials disclosed in the present invention have good luminescence properties, can be used as luminescent materials in organic light-emitting diodes, have good luminescence efficiency and device life, and have potential application in the field of organic electroluminescent devices. BRIEF DESCRIPTION OF THE DRAWINGS
[0046] Figure 1 is a structural diagram of an organic light emitting diode device according to the present invention,
[0047] 10 represents a glass substrate, 20 represents an anode, 30 represents a hole injection layer, 40 represents a hole transport layer, 50 represents a light emitting layer, 60 represents an electron transport layer, 70 represents an electron injection layer, and 80 represents a cathode. DETAILED DESCRIPTION
[0048] The present invention is further described in detail below with reference to the embodiments.
[0049] Example 1:
[0050] Synthesis of complex 4
[0051]
[0052] Synthesis of compound 4c:
[0053] Under nitrogen, compound 4a (2.0 g, 8.4 mmol), compound 4b (4.53 g, 17.6 mmol), Pd(PPh3)4 (0.49 g, 0.42 mmol), NaOH (0.71 g, 17.6 mmol), toluene (40 ml), and water (10 mL) were added to a three-necked flask. The temperature was raised to 70°C and the mixture was stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water (120 ml) was added, and the mixture was extracted with ethyl acetate. The organic phase was collected and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.50 g of an off-white solid in a 59% yield. ESI-MS (m / z): 503.2 (M+1).
[0054] Synthesis of compound 4d:
[0055] Under nitrogen, compound 4c (2 g, 3.98 mmol), pinacol borate (5.04 g, 19.8 mmol), Pd(OAc)2 (88 mg, 0.4 mmol), X-phos (380 mg, 0.8 mmol), triethylamine (2.76 mL, 19.8 mmol), and toluene (40 mL) were added to a three-necked flask and heated to 80°C for 16 hours. After completion of the reaction, the reaction solution was cooled to room temperature. The insoluble solids in the reaction solution were filtered off, and ethyl acetate (200 mL) and water (200 mL) were added to the filtrate for extraction. The organic phase was collected and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.2 g of an off-white solid, with a yield of 50.5%. ESI-MS (m / z): 597.5.2 (M+1).
[0056] Synthesis of compound 4f:
[0057] Under argon, methylamine hydrochloride (1.2 g, 18.1 mmol) was dissolved in THF (20 ml). Lithium diisopropylamide (LDA) (15 ml; 2 mol / L) was added dropwise at 0°C and allowed to react for 0.5 h. 4e (4.0 g, 18.1 mmol) was dissolved in THF (10 ml) and added dropwise to the reaction mixture. The mixture was allowed to react at 0°C for 0.5 h. After the addition was complete, the temperature was raised to 45°C and allowed to react for 16 h. After the reaction, water (50 ml) was added, the mixture was extracted with ethyl acetate, the organic phase was collected, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to afford 1.9 g of a brown solid as an off-white solid, with a yield of 45%. ESI-MS (m / z): 231.2 (M+1).
[0058] Synthesis of compound 4g:
[0059] Under nitrogen, 4f (4.1 g, 17.8 mmol) and iron powder (4.13 g, 74.01 mmol) were added to acetic acid (50 ml) and reacted at 80°C for 1 hour. After completion of the reaction, the solid was filtered and rinsed with dichloromethane. Water (250 ml) was added and extracted with dichloromethane. The organic phase was collected and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.2 g of an off-white solid, a reddish-brown solid, with a yield of 62%. ESI-MS (m / z): 201.2 (M+1).
[0060] Synthesis of compound 4i:
[0061] Under nitrogen, 4g (2.0g, 10.0mmol), 4h (3.2g, 12.9mmol), and Na2S2O5 (5.6g, 29.8mmol) were dissolved in DMF (10ml) and reacted at 90°C for 24 hours. After completion of the reaction, water (100ml) was added, and the mixture was extracted with dichloromethane. The organic phase was collected and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 3.1g of an off-white solid (75% yield). ESI-MS (m / z): 415.2 (M+1).
[0062] Synthesis of compound 4j:
[0063] Under nitrogen, 4d (1.5 g, 2.5 mmol), 4i (2.3 g, 5.5 mmol), Pd(dba) (54 mg, 0.0585 mmol), X-phos (56 mg, 0.117 mmol), KCO (0.71 g, 5.2 mmol), and toluene / ethanol / water (14 mL / 3.5 mL / 3.5 mL) were added to a three-necked flask and reacted at 80°C for 16 hours. The reaction solution was cooled to room temperature, and ethyl acetate (100 mL) and water (100 mL) were added to extract the solution. The organic phase was collected and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.1 g of a yellow foamy solid in 82% yield. ESI-MS (m / z): 1013.7 (M+1).
[0064] Synthesis of complex 4:
[0065] Under nitrogen, compound 4j (0.5 g, 0.49 mmol), Pt(PhCN)2Cl2 (0.70 g, 1.48 mmol), and acetic acid (100 ml) were added to a three-necked flask and reacted at 130°C for 48 hours. After completion of the reaction, the reaction solution was cooled to room temperature and 800 ml of water was added to precipitate a solid. The solid was filtered, washed with water, dissolved in dichloromethane, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain an off-white solid (0.41 g of a red solid, with a yield of 59%). ESI-MS (m / z): 1399.5 (M+1).
[0066] Example 2:
[0067] Synthesis of complex 16
[0068]
[0069] Synthesis of compound 16a:
[0070] Compound 16a was prepared by replacing methylamine hydrochloride with 3-aminopyridine, following the synthetic method of compound 4f, to obtain 6.3 g of a brownish-red solid with a yield of 47%. ESI-MS (m / z): 294.1 (M+1).
[0071] Synthesis of compound 16b:
[0072] Compound 16b was prepared by replacing compound 4f with compound 16a according to the synthetic method of compound 4g to obtain 1.7 g of a brown-red solid with a yield of 60%. ESI-MS (m / z): 264.2 (M+1).
[0073] Synthesis of compound 16c:
[0074] Compound 16c was prepared by replacing compound 4g with compound 16b according to the synthetic method of compound 4f to obtain 2.1 g of off-white solid with a yield of 68%. ESI-MS (m / z): 478.2 (M+1).
[0075] Synthesis of compound 16d:
[0076] Compound 16d was prepared by replacing compound 4i with compound 16c according to the synthetic method of compound 4j to obtain 3.6 g of a light yellow solid with a yield of 75%. ESI-MS (m / z): 1139.8 (M+1).
[0077] Synthesis of complex 16:
[0078] Compound 16d was used to replace compound 4j, and complex 16 was prepared according to the synthesis method of complex 4 to obtain 0.9 g of a red solid with a yield of 39%. ESI-MS (m / z): 1526.7 (M+1).
[0079] Example 3:
[0080] Synthesis of complex 20
[0081]
[0082] Synthesis of compound 20a:
[0083] Compound 20a was prepared by replacing methylamine hydrochloride with 3,5-di-tert-butylaniline and referring to the synthesis method of compound 4f to obtain 7.0 g of a brown-red solid with a yield of 50%. ESI-MS (m / z): 405.2 (M+1).
[0084] Synthesis of compound 20b:
[0085] Compound 20b was prepared by replacing compound 4f with compound 20a according to the synthetic method of compound 4g to obtain 1.3 g of a brown-red solid with a yield of 68%. ESI-MS (m / z): 375.2 (M+1).
[0086] Synthesis of compound 20c:
[0087] Compound 20c was prepared by replacing compound 4g with compound 20b according to the synthetic method of compound 4f to obtain 1.2 g of a light yellow solid with a yield of 76%. ESI-MS (m / z): 589.3 (M+1).
[0088] Synthesis of compound 20d:
[0089] Compound 20d was prepared by replacing compound 4i with compound 20c according to the synthetic method of compound 4j to obtain 2.6 g of a light yellow solid with a yield of 68%. ESI-MS (m / z): 1363.0 (M+1).
[0090] Synthesis of complex 20:
[0091] Compound 20d was used to replace compound 4j, and complex 20 was prepared according to the synthesis method of complex 4 to obtain 1.3 g of a red solid with a yield of 52%. ESI-MS (m / z): 1748.9 (M+1).
[0092] Example 4:
[0093] Synthesis of complex 77
[0094]
[0095] Synthesis of compound 77b:
[0096] Compound 77b was prepared by replacing compound 4i with compound 77a (synthesized in J. Mater. Chem. C, 2015, 3, 8212-8218) and following the synthesis of compound 4j to obtain 1.5 g of a pale yellow solid in a 53% yield. ESI-MS (m / z): 760.3 (M+1). Synthesis of complex 77:
[0097] Compound 77 was prepared by replacing compound 4j with compound 77b, and referring to the synthesis method of complex 4, to obtain 0.90 g of a red solid with a yield of 65%. ESI-MS (m / z): 1149.3 (M+1).
[0098] Example 5:
[0099] Synthesis of complex 78
[0100]
[0101] Synthesis of compound 78b:
[0102] Compound 78b was prepared by replacing compound 4i with compound 78a (synthesized by reference to Tetrahedron, 2020, 76, 130982) and following the synthesis of compound 4j to obtain 1.7 g of a light yellow solid in a 60% yield. ESI-MS (m / z): 795.4 (M+1). Synthesis of complex 78:
[0103] Compound 78b was substituted for compound 4j, and complex 78 was prepared according to the synthetic method of complex 4 to obtain 0.98 g of a red solid with a yield of 67%. ESI-MS (m / z): 1181.2 (M+1).
[0104] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.
[0105] Examples 6-10:
[0106] The organic light emitting diode is prepared by using the complex luminescent material of the present invention. The device structure is shown in FIG. Figure 1 .
[0107] First, the transparent conductive ITO glass substrate 10 (with the anode 20 thereon) is cleaned in sequence with a detergent solution and deionized water, ethanol, acetone, and deionized water, and then treated with oxygen plasma for 30 seconds.
[0108] Then, a PEDOT:PSS solution (poly(3,4-ethylenedioxythiophene)-polystyrenesulfonic acid) was spin-coated on the ITO to prepare the hole injection layer 30 .
[0109] Then, PVKH solution was spin-coated on the hole injection layer to form a hole transport layer 40 with a thickness of 10 nm.
[0110] Then, a 20 nm thick light-emitting layer 50 was prepared on the hole transport layer by spin-coating a toluene mixed solution of a platinum complex and a host material. The toluene mixed solution consisted of platinum complex: TPD: PBD = 6%: 47%: 47% (the platinum complexes corresponding to Examples 6-10 were: complexes 4, 16, 20, 77, 78, respectively).
[0111] Then, TPBI was evaporated to a thickness of 40 nm on the light-emitting layer as the electron transport layer 60 .
[0112] Finally, 1 nm LiF was evaporated to form the electron injection layer 70 and 100 nm Al was evaporated to form the device cathode 80 .
[0113] Comparative Example 1:
[0114] The same preparation method was adopted to prepare the device of Comparative Example 1, except that compound Ref-1 (Chem. Sci., 2021, 12, 6172-6180) was used to replace the platinum complex in the above embodiment.
[0115] The structural formulas of PVKH, TBD, PBD, TPBI, and Ref-1 in the device are as follows:
[0116]
[0117] The organic electroluminescent devices of Examples 6-10 were 2 The device performance at the current density is listed in the table below:
[0118]
[0119]
[0120] As shown in Table 1, under the same conditions, the platinum complex material of the present invention, when applied to organic light-emitting diodes (OLEDs), emits deep red light with a lower driving voltage and higher luminous efficiency than the comparative molecule ref-1. Notably, the device lifespan of OLEDs based on the complex of the present invention significantly outperforms the complex material in the comparative example, demonstrating promising potential for industrialization.
[0121] The various embodiments described above are intended to be illustrative only and are not intended to limit the scope of the present invention. Without departing from the spirit of the present invention, the various materials and structures described herein may be replaced with other materials and structures. It should be understood that those skilled in the art can make numerous modifications and variations based on the principles of the present invention without requiring creative effort. Therefore, any technical solution that can be derived through analysis, reasoning, or partial research based on the prior art should fall within the scope of protection defined by the claims.
Claims
1. A binuclear platinum complex having the structure of formula (I): in: X1 to X 12 Each independently selected from CR; A is selected from NR 3 , O, S or Se; R is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 6 carbon atoms; R 3 is selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms; The heteroatoms in the heteroaryl group are one or more of N, S, and O; The substitution is substitution by halogen, cyano, C6-C12 aryl or C1-C4 alkyl.
2. The binuclear platinum complex according to claim 1, wherein R is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted alkoxy having 1 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 6 carbon atoms; R 3 independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 6 carbon atoms.
3. The binuclear platinum complex according to claim 2, wherein R is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C1-C4 alkyl, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, or substituted or unsubstituted heteroaryl having 3-6 carbon atoms; R 3 independently selected from hydrogen, deuterium, C1-C4 alkyl, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, or substituted or unsubstituted heteroaryl having 3-6 carbon atoms; A is selected from NR 3 , O or S; The substitution is substituted by a phenyl group or a C1-C4 alkyl group.
4. The binuclear platinum complex according to claim 3, wherein R is selected from the group consisting of hydrogen, deuterium, cyano, methyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, or substituted or unsubstituted pyrimidinyl; R 3 are independently selected from hydrogen, deuterium, methyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl or substituted or unsubstituted pyrimidinyl.
5. The binuclear platinum complex according to claim 3 has the following structure:
6. The binuclear platinum complex according to claim 5, wherein R, R 3 are independently selected from hydrogen, deuterium, methyl, tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, or substituted or unsubstituted pyridyl.
7. The binuclear platinum complex according to claim 6, wherein the general formula (I) is the following structure:
8. The binuclear platinum complex according to claim 7, wherein X1, X3, and X9 are CR, X2, X4-X8, and X10 are CH, and R is hydrogen, deuterium, methyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, or pyridyl.
9. The binuclear platinum complex according to claim 1, which is one of the following compounds:
10. A precursor of a binuclear platinum complex, i.e., a ligand, has the following structural formula: Where X1 to X 12 , A is defined as described in any one of claims 1-9.
11. Use of the binuclear platinum complex according to any one of claims 1 to 9 in an organic light emitting diode, an organic thin film transistor, an organic photovoltaic device, a light emitting electrochemical cell or a chemical sensor.
12. An organic light-emitting diode comprising a cathode, an anode, and an organic layer, wherein the organic layer is one or more 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 organic layer contains the binuclear platinum complex according to any one of claims 1 to 9. 13 . The organic light emitting diode according to claim 12 , wherein the layer where the binuclear platinum complex is located is a light emitting layer.
Citation Information
Patent Citations
Double-nuclear ring metal platinum complex near-infrared light-emitting material and application thereof
CN101619045A
Cyclometalated transition metal complex and organic electroluminescence device using the same
CN102344465A