Complex and OLED (organic light emitting diode) with same
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A technology of organic light-emitting devices and complexes, which is applied in the fields of light-emitting materials, organic chemistry, and electric solid-state devices, and can solve the problems of high driving voltage, low light-emitting efficiency, and poor thermal stability.
Inactive Publication Date: 2018-10-02
CHANGCHUN HYPERIONS TECH CO LTD
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[0004] Organic complexes have good luminescent properties, many of which have been extensively studied in the scientific research and industrial production of OLEDs and other electroluminescent technologies, but there are still deficiencies. Phosphorescent materials generally have poor thermal stability and low luminous efficiency. , the problem of high driving voltage, and the fundamental factor that determines the performance of organic electroluminescent devices is the choice of materials. Therefore, it is urgent to design and develop an organic complex with higher luminous efficiency and lower driving voltage.
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Embodiment 1
[0071] Embodiment 1: the preparation of compound 1
[0072]
[0073] Preparation of Intermediate A1
[0074] Dissolve 1.66 g (10.5 mmol) of 2,3-diaminonaphthalene and 1.4 g (10.0 mmol) of 1-phenyl-1,2-propanedione in 30 ml of absolute ethanol, and stir at reflux for 5 hours. After cooling to room temperature, the resulting solution was concentrated and separated by column chromatography, using petroleum ether / ethyl acetate=12 / 1 as the eluent, to obtain a yellow solid powder with a yield of 80%, and compound intermediate A1 was obtained.
[0075] Preparation of Intermediate B1
[0076] In a 1L three-necked flask, iridium trichloride hydrate (14.11g, 40mmol) and intermediate A1 (27.23g, 170mmol) were added, then 300mL of 2-ethoxyethanol and 100mL of water were added, and the mixture was refluxed overnight under a nitrogen atmosphere. After the reaction, the temperature was lowered to room temperature, the precipitate was filtered, washed with methanol, and dried to obtain i...
Embodiment 2
[0081] Embodiment 2: the preparation of compound 10
[0082] The b1 in Example 1 was replaced by equimolar b10, and the other steps were the same as in Example 1 to obtain the target compound 10 (5.59 g, 29%).
[0083]
[0084] Mass Spectrum m / z: 963.38 (calculated: 963.37). Theoretical element content (%)C 53 h 50 IrN 6 : C, 66.09; H, 5.23; Ir, 19.96; N, 8.72 Measured element content (%): C, 66.09; H, 5.22; Ir, 19.97; N, 8.72. The above results confirmed that the obtained product was the target product.
Embodiment 3
[0085] Embodiment 3: the preparation of compound 29
[0086] The c1 (bromobenzene) in Example 1 was converted into equimolar c29 (isopropyl bromide), and the other steps were the same as in Example 1 to obtain the target compound 29 (5.23 g, 29%).
[0087]
[0088] Mass Spectrum m / z: 901.37 (calculated: 901.36). Theoretical element content (%)C 48 h 48 IrN 6 : C, 63.98; H, 5.37; Ir, 21.33; N, 9.33 Measured element content (%): C, 63.99; H, 5.36; Ir, 21.33; N, 9.33. The above results confirmed that the obtained product was the target product.
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Abstract
The invention discloses a complex and an OLED (organic light emitting diode) with the same and relates to the technical field of organic optoelectronic materials. According to the complex, by means ofintroduction of a big Pi conjugated structure and a steric hindrance group, collision of triplet excitons is reduced, and the problem of roll-off of efficiency of the OLED under the large current density is solved; an electron-rich dinitrogen coordination structure in the structure is beneficial to stabilizing central trivalent metal cations and also affects electron cloud distribution on metal iridium, thereby producing great influence on photoelectric property of the whole complex molecule; besides, a four-membered ring consisting of ligands of the dinitrogen coordination structure and metals has higher rigidity, so that reduction of unnecessary vibration energy loss is facilitated, and efficient luminescence property is realized. The complex is enabled to achieve better heat stabilityand chemical properties by regulating substitutional groups. The OLED is prepared from the complex, and especially when the complex is taken as a doping material, the OLED shows the advantages of lowdrive voltage and high luminous efficiency and is better than a present common OLED.
Description
technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a complex and an organic light-emitting device thereof. Background technique [0002] In recent years, organic light-emitting diodes (OLEDs) have been favored due to their excellent properties such as ultra-thin, flexible, self-luminous, and wide viewing angle. Among them, due to the existence of their own heavy atoms, organic transition complexes (such as iridium, platinum, etc.) can simultaneously use singlet and triplet excitons to emit light through spin coupling, and theoretically achieve 100% internal quantum efficiency, which has attracted everyone's attention. Widespread concern. At present, the dopant materials in the light-emitting layer of organic electroluminescent devices are still mainly phosphorescent materials, most of which are organic complexes. [0003] Since Tang et al. used 8-hydroxyquinoline aluminum (Alq3) as the light-emitting lay...
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