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A compound with quinolinone derivative as the core and its application in organic electroluminescent devices
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A technology of compounds and derivatives, applied in the field of organic electroluminescent devices, can solve the problems of different performances and achieve the effects of reverse system crossing, increasing orbital overlap, and improving luminous efficiency
Active Publication Date: 2021-10-22
JIANGSU SUNERA TECH CO LTD
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In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.
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preparation example Construction
[0070] Preparation of Intermediate B:
[0071] Preparation of intermediate Ⅰ-1:
[0072]
[0073] (1) In a 500mL three-necked flask, under nitrogen protection, add 0.05mol raw material C-1, 0.06mol raw material D-1, dissolve in a mixed solvent (180ml toluene, 90ml ethanol), and then add 0.15mol Na 2 CO 3 aqueous solution (2M), stirred under nitrogen for 1 hour, then added 0.0005mol Pd(PPh 3 ) 4 , Heated to reflux at 100°C for 15 hours, sampled and plated, and the reaction was complete. Naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate L-1 with a HPLC purity of 93.4% and a yield of 64.2%.
[0074] Elemental analysis structure (molecular formula C 23 h 17 BrS 2 ): theoretical value C, 63.16; H, 3.92; Br, 18.27; S, 14.66; tested value: C, 63.15; H, 3.92; Br, 18.27; ESI-MS (m / z) (M+): theoretical value 436.00, found value 436.12.
[0075] (2) Under the protection of nitrogen, weigh 0.01mol of i...
Embodiment 1
[0107] Embodiment 1: the synthesis of compound 2:
[0108]
[0109] In a 250mL three-neck flask, blow nitrogen, add 0.01mol raw material A-1, 0.015mol intermediate I-1, dissolve with a mixed solvent of toluene and ethanol (toluene 90mL, ethanol 45mL), and then add 0.03mol Na 2 CO 3 Aqueous solution (2M), stirred with nitrogen for 1h, then added 0.0001mol Pd(PPh 3 ) 4 , Heated to reflux at 100°C for 15h, sampled and plated, and the reaction was complete. After natural cooling, filtration, rotary evaporation of the filtrate, and passing the residue through a silica gel column, the target product was obtained with a purity of 98.1% and a yield of 84.9%. Elemental analysis structure (molecular formula C 52 h 36 N 2 OS): Theoretical value C, 84.75; H, 4.92; N, 3.80; O, 2.17; S, 4.35; Test value: C, 84.75; ESI-MS (m / z) (M+): theoretical value 736.25, found value 736.19.
Embodiment 2
[0110] Embodiment 2: the synthesis of compound 12:
[0111]
[0112] The preparation method of compound 12 is the same as that of Example 1, except that raw material A-1 is replaced by raw material A-2, and intermediate I-1 is replaced by intermediate II-1. Elemental analysis structure (molecular formula C 51 h 36 N 4 O): theoretical value C, 84.97; H, 5.03; N, 7.77; O, 2.22; tested value: C, 84.96; H, 5.03; N, 7.77; HPLC-MS: The molecular weight of the material is 720.29, and the measured molecular weight is 720.35.
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Abstract
The invention discloses a compound with quinolinone derivatives as the core and its application in organic electroluminescent devices. The structure of the compound of the invention contains quinolinone derivatives as electron acceptors, which is beneficial for electrons in the light-emitting layer in the transmission. The attached heterocyclic group is an electron donor, which facilitates the transport of holes in the emissive layer. The nitrogen atom inside the heteroatom-containing benzazinone is a saturated atom, which not only has strong rigidity, but also helps to improve the triplet energy level of the mother nucleus compound. The combination of electron donor and electron acceptor can improve the excitonic Recombination efficiency, lower start-up voltage, and improve device performance. When the compound of the present invention is used as a light-emitting layer material of an organic electroluminescent device, the current efficiency of the device is greatly improved, and at the same time, the lifetime of the device is significantly improved.
Description
technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with quinolinone derivatives as the core and its application in organic electroluminescent devices. Background technique [0002] At present, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, compared with actual product application requirements, the luminous efficiency and service life of OLED devices Further improvement is required. [0003] The current research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device. In order to realize the continuous improvement of the performance of OLED devices, not only the innovation of OLED device structure and manufacturing process is required, but also t...
Claims
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