WO2022088873A1 - 一种金属络合物及其应用 - Google Patents
一种金属络合物及其应用 Download PDFInfo
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- WO2022088873A1 WO2022088873A1 PCT/CN2021/113932 CN2021113932W WO2022088873A1 WO 2022088873 A1 WO2022088873 A1 WO 2022088873A1 CN 2021113932 W CN2021113932 W CN 2021113932W WO 2022088873 A1 WO2022088873 A1 WO 2022088873A1
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- compound
- metal complex
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 25
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- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 14
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
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- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- the present invention relates to the technical field of organic electroluminescence, in particular to the technical field of organic electroluminescence devices, and in particular to a metal complex and its application in organic electroluminescence devices.
- OLEDs organic electroluminescent devices
- OLED devices the basic structure of OLED devices is that various organic functional material films with different functions are mixed between metal electrodes, like a sandwich structure. Driven by current, holes and electrons are injected from the cathode and anode, and holes and electrons are respectively injected. After moving a certain distance, the light-emitting layer is recombined and released in the form of light or heat, thereby producing the luminescence of the OLED.
- organic functional materials are the core components of organic electroluminescent devices, and the thermal stability, photochemical stability, electrochemical stability, quantum yield, film formation stability, crystallinity, color saturation, etc. A major factor in device performance.
- organic functional materials include fluorescent materials and phosphorescent materials.
- the fluorescent material is usually an organic small molecule material, and generally can only use 25% of the singlet state to emit light, so the luminous efficiency is relatively low.
- the phosphorescent material can utilize the energy of 75% triplet excitons in addition to the 25% singlet state due to the spin-orbit coupling effect caused by the heavy atom effect, so the luminous efficiency can be improved.
- phosphorescent materials started late, and the thermal stability, lifespan, and color saturation of the materials need to be improved, which is a challenging topic.
- various organometallic compounds have been developed as such phosphorescent materials.
- the market still expects the development of novel materials that can further improve the performance of organic electroluminescent devices.
- the present invention provides high-performance organic electroluminescent devices and novel materials capable of realizing such organic electroluminescent devices.
- the present inventors have repeatedly conducted intensive studies in order to achieve the aforementioned object, and found that a high-performance organic electroluminescence device can be obtained by using a metal complex including a structure represented by the following formula (1) as a ligand.
- One of the objectives of the present invention is to provide a metal complex, which has the advantages of low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, long device life and the like, Can be used in organic electroluminescent devices. Especially as a green light-emitting dopant, it has the possibility of being applied to the OLED industry.
- R1-R18 is the structure shown in formula (2);
- M is independent of Pt, Pd;
- X independently represents O, S, Se, CRaRb;
- L1-L3 are each independently selected from direct bonding single bond, O, S, Se, NRc, CRdRe, SO, SO2, PO(Rf)(Rg);
- L4 is a single bond, O, substituted or unsubstituted C1-C20 alkylene, substituted or unsubstituted C3-C30 cycloalkylene, substituted or unsubstituted C1-C20 heteroalkylene, substituted or unsubstituted C7-C30 aralkylene, substituted or unsubstituted C2-C20 alkenylene, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 alkene
- Aryl substituted or unsubstituted C3-C30 heteroarylene, substituted or unsubstituted C3-C30 arylenesilyl, substituted or unsubstituted C0-C20 imino;
- R1-R18, R101-R102 and Ra-Rg are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or Unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, Substituted or unsubstituted C3-C30 arylsilyl group, substituted or unsubstituted
- substitution numbers of R101 and R102 independently represent no substitution to the maximum substitution number.
- R1-R18 is the structure shown in formula (2);
- X independently represents O, S, Se, CRaRb;
- L4 is a single bond, O, substituted or unsubstituted C1-C10 alkylene, substituted or unsubstituted C3-C10 cycloalkylene, substituted or unsubstituted C2-C10 heteroalkylene, substituted or unsubstituted C7-C20 aralkylene, substituted or unsubstituted C2-C20 alkenylene, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 alkene Aryl, substituted or unsubstituted C3-C30 heteroarylene, substituted or unsubstituted C3-C30 arylenesilyl, substituted or unsubstituted C0-C20 imino;
- R1, R2, R7, R8, R10, R11, R18, R101, R102, Ra and Rb are as defined above.
- L4 is a single bond, O and one of the following structures:
- Rx represents no substitution to the maximum number of substitutions.
- Rx is multi-substituted, two adjacent substituents can be connected to each other to form a cyclic or combined ring structure;
- Rx and Ry are independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, Substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl , substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 aryl Silyl group, substituted or unsubstituted C0-C20 amine group, cyano group,
- R1, R2, R7, R8, R10, R11, R18, R101, R102, Ra, Rb, Rx and Ry are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, Substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C2-C20 alkenyl , substituted or unsubstituted C3-C8 alkylsilyl, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl, substituted or unsubstituted C3-C10 aryl Silyl group, substituted or unsubstituted C0-C6 amine group, cyano group.
- R1, R2, R7, R8, R10, R11, R18, R101, R102, Ra, Rb, Rx and Ry are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, Substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted phenylalkyl, substituted or unsubstituted C6-C10 aryl, substituted substituted or unsubstituted C3-C10 heteroaryl.
- R18 is deuterium, substituted or unsubstituted straight-chain carbon atom C1-C4 alkyl, substituted or unsubstituted C1-C6 cycloalkyl, and the substitution is substituted by deuterium and halogen.
- the precursor of the metal complex has the following structure:
- R1-R18 is the structure shown in formula (2);
- R1-R18, R101, and R102 are the same as those described above.
- Another object of the present invention is to provide an electroluminescent device comprising: a cathode, an anode and an organic layer disposed between the cathode and the anode, at least one layer of the organic layer contains a metal complex.
- Another object of the present invention is to provide an electroluminescent device, wherein the organic layer comprises a light-emitting layer, and the metal complex is used as a material in the light-emitting layer, especially as a green light-emitting material;
- Another object of the present invention is to provide an electroluminescent device, wherein the organic layer includes a hole injection layer, and the metal complex is used as a material in the hole injection layer.
- the device results show that the compound of the present invention has the advantages of high optical and electrochemical stability, high color saturation, high luminous efficiency, long device life and the like, and can be used in organic electroluminescent devices. Especially as a green phosphorescent material, it has the possibility of being applied to the OLED industry.
- A1-3 (96g, 0.63mol, 1.0eq), benzaldehyde (74.6g, 0.7mol, 1.1eq), potassium hydroxide (179.3g, 3.2mol, 4.0eq), deionized water were sequentially added to a 3L three-necked flask (195ml), methanol (670ml), replaced by vacuum and nitrogen three times, heated to 50°C and reacted overnight. A large amount of solid was precipitated in the reaction, cooled to room temperature, filtered, collected and added to ethyl acetate (500 ml), stirred to dissolve, and washed twice with 200 ml of deionized water each time.
- A1-4 (80g, 0.33mol, 1.0eq), A1-2 (135.6g, 0.33mol, 1.0eq), ammonium acetate (155.2g, 2.0mol, 6.0eq), acetic acid (350ml) were sequentially added to a 1L three-necked flask ), replaced by vacuum and nitrogen three times, heated to reflux and reacted overnight. The mixture was cooled to room temperature, concentrated to remove acetic acid, and the spin-dried solid was added with dichloromethane (1.0 L), stirred to dissolve, and deionized water was added for washing twice with 300 ml each.
- reaction solution was added to a beaker containing deionized water (650 ml), stirred to precipitate a solid, and the solid was collected by filtration.
- Sublimation pure A 1 (3.64 g, yield 69.5%) was obtained after sublimation purification of 5.23 g of A 1 crude product, mass spectrum: 774.2 (M+H).
- the orange-yellow compound A 82 (3.97 g, yield 63.7%) can be obtained only by changing the corresponding raw materials.
- Sublimation pure A 82 (2.58 g, yield 64.9%) was obtained after sublimation purification of 3.97 g of crude A 82.
- the orange-yellow compound A 89 (3.57 g, yield 56.7%) can be obtained only by changing the corresponding raw materials.
- Sublimation pure A 89 (2.16 g, yield 60.5%) was obtained after sublimation purification of 3.57 g of crude A89.
- the orange-yellow compound A 100 (4.12 g, yield 58.8%) can be obtained only by changing the corresponding raw materials.
- Sublimation pure A 100 (2.59 g, yield 62.86%) was obtained after sublimation purification of 4.12 g of crude A 100.
- the orange-yellow compound A 125 (3.93 g, yield 59.3%) can be obtained only by changing the corresponding raw materials.
- Sublimation pure A 125 (2.28 g, yield 58.0%) was obtained after sublimation purification of 3.93 g of crude A 125.
- the orange-yellow compound A 197 (3.67 g, yield 55.8%) can be obtained only by changing the corresponding raw materials.
- Sublimation pure A 197 (2.08 g, yield 56.6%) was obtained after sublimation purification of 3.67 g of crude A 197. Mass spectrum: 903.9 (M+H).
- a 50mm*50mm*1.0mm glass substrate with ITO (100nm) transparent electrodes was ultrasonically cleaned in ethanol for 10 minutes, dried at 150 degrees, and then treated with N2Plasma for 30 minutes.
- the washed glass substrate was mounted on the substrate holder of the vacuum evaporation device, and the compound HATCN was evaporated on the surface of the transparent electrode line side in a manner to cover the transparent electrode to form a thin film with a thickness of 5 nm, and then evaporated.
- ETL film layer (25nm) LiQ film layer (1nm) was evaporated on the light-emitting layer in turn, and finally a layer of metal Al (100nm) was evaporated as an electrode.
- Example 12 A 197 4.69 54 534 191 Comparative Example 1 Contrast 1 4.84 31 510 115 Comparative Example 2 Contrast 2 4.86 38 517 136
- the organic electroluminescence device using the compound of the present invention as the green light dopant shows more superior performance in driving voltage, luminous efficiency and device life compared with the comparative compound.
- the compound of the present invention has the advantages of high light and electrochemical stability, high color saturation, high luminous efficiency, long device life and the like, and can be used in organic electroluminescent devices. Especially as a green phosphorescent material, it has the possibility of being applied to the OLED industry.
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- Crystallography & Structural Chemistry (AREA)
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Abstract
Description
掺杂材料 | 启动电压V | 电流效率Cd/A | 峰值波长nm | LT90@3000nits | |
实施例1 | A1 | 4.77 | 41 | 523 | 140 |
实施例2 | A 3 | 4.73 | 44 | 525 | 143 |
实施例3 | A 28 | 4.71 | 46 | 528 | 149 |
实施例4 | A 39 | 4.68 | 51 | 527 | 177 |
实施例5 | A 71 | 4.69 | 48 | 525 | 172 |
实施例6 | A 82 | 4.68 | 53 | 523 | 189 |
实施例7 | A 89 | 4.73 | 45 | 529 | 158 |
实施例8 | A 100 | 4.78 | 51 | 531 | 186 |
实施例9 | A 111 | 4.81 | 49 | 529 | 176 |
实施例10 | A 125 | 4.67 | 51 | 533 | 169 |
实施例11 | A 168 | 4.73 | 47 | 535 | 181 |
实施例12 | A 197 | 4.69 | 54 | 534 | 191 |
对比例1 | 对比1 | 4.84 | 31 | 510 | 115 |
对比例2 | 对比2 | 4.86 | 38 | 517 | 136 |
Claims (12)
- 一种金属络合物,其具有式(1)所示的结构;其中R1-R18至少之一为式(2)所示的结构;其中:*表示与式(1)连接的位置;M独立的为Pt、Pd;X独立的表示O,S,Se,CRaRb;L1-L3各自独立的选自直接键合单键,O,S,Se,NRc,CRdRe,SO,SO2,PO(Rf)(Rg);L4为单键,O,取代的或未取代的C1-C20亚烷基、取代的或未取代的C3-C30亚环烷基、取代的或未取代的C1-C20亚杂烷基、取代的或未取代的C7-C30亚芳烷基,取代或未取代的C2-C20的亚烯基、取代的或未取代的C3-C30亚烷基硅基、取代的或未取代的C6-C30亚芳基、取代的或未取代的C3-C30亚杂芳基、取代的或未取代的C3-C30亚芳基硅基、取代或未取代的C0-C20的亚胺基;其余R1-R18、R101-R102和Ra-Rg独立地选自氢、氘、卤素、取代的或未取代的C1-C20烷基、取代的或未取代的C3-C30环烷基、取代的或未取代的C1-C20杂烷基、取代的或未取代的C7-C30芳烷基、取代的或未取代的C1-C20烷氧基、取代的或未取代的C6-C30芳氧基、取代或未取代的C2-C20的烯基、取代的或未取代的C3-C30烷基硅基、取代的或未取代的C6-C30芳基、取代的或未取代的C3-C30杂芳基、取代的或未取代的C3-C30芳基硅基、取代或未取代的C0-C20的胺基、氰基、腈、异腈、膦基;或者任意两个相邻的基团之间相互连接以形成环状结构或者并环结构;所述取代为被氘、卤素、C1-C4烷基、氰基所取代;R101、R102的取代个数独立的表示无取代到最大取代个数。
- 根据权利要求1-3任一所述的金属络合物,其中L4为单键、O及以下结构之一:其中:*表示与式(1)及式(2)连接的位置;Rx的个数表示无取代到最大取代个数,当Rx为多取代时,相邻的两个取代基可以互相连接以形成环状或并环结构;Rx和Ry独立地为氢、氘、卤素、取代的或未取代的C1-C20烷基、取代的或未取代的C3-C30环烷基、取代的或未取代的C1-C20杂烷基、取代的或未取代的C7-C30芳烷基、取代的或未取代的C1-C20烷氧基、取代的或未取代的C6-C30芳氧基、取代或未取代的C2-C20的烯基、取代的或未取代的C3-C30烷基硅基、取代的或未取代的C6-C30芳基、取代的或未取代的C3-C30杂芳基、取代的或未取代的C3-C30芳基硅基、取代或未取代的C0-C20的胺基、氰基、腈、异腈、膦基。
- 根据权利要求4所述的金属络合物,其中R1、R2、R7、R8、R10、R11、R18、R101、R102、Ra、Rb、Rx和Ry独立地选自氢、氘、卤素、取代的或未取代的C1-C8烷基、取代的或未取代的C3-C10环烷基、取代的或未取代的C1-C8杂烷基、取代的或未取代的C7-C10芳烷基、取代或未取代的C2-C20的烯基、取代的或未取代的C3-C8烷基硅基、取代的或未取代的C6-C10芳基、取代的或未取代的C3-C10杂芳基、取代的或未取代的C3-C10芳基硅基、取代或未取代的C0-C6的胺基、氰基。
- 根据权利要求5所述的金属络合物,其中R1、R2、R7、R8、R10、R11、R18、R101、R102、Ra、Rb、Rx和Ry独立地选自氢、氘、卤素、取代的或未取代的C1-C8烷基、取代的或未取代的C3-C10环烷基、取代的或未取代的C1-C8杂烷基、取代的或未取代的苯基烷基、取代的或未取代的C6-C10芳基、取代的或未取代的C3-C10杂芳基。
- 根据权利要求6所述的金属络合物,其中R18为氘、取代或未取代的直链碳原子C1-C4 烷基、取代或未取代的C1-C6个环烷基,所述取代为被氘或卤素所取代。
- 根据权利要求6所述的金属络合物,其中R1和R2至少之一不为氢。
- 一种电致发光器件,其包括:阴极,阳极以及设置在阴极阳极之间的有机层,所述有机层至少一层包含权利要求1-9任一所述的金属络合物。
- 如权利要求11所述的电致发光器件,其中所述有机层包含发光层,所述金属络合物作为发光层中的绿色发光材料;或者其中所述有机层包含空穴注入层,所述金属络合物作为空穴注入层中的空穴注入材料。
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