Preparation method of organic luminescent material based on quinacridine and luminescent device thereof
A luminescent material, quinacridine technology, applied in luminescent materials, organic chemistry, electric solid-state devices, etc., can solve the problems of less correlation research, restrictions on high-efficiency delayed fluorescent materials, and limited types of TADF materials, so as to reduce product production costs , the effect of improving device performance
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Embodiment 1
[0031] Synthesis of compound M1
[0032] The synthetic process of compound M1 comprises the following steps:
[0033] The first step: the synthesis of intermediate 1:
[0034]
[0035] In a 100mL two-necked flask, add 2.3g (7.0mmol) 9-(4-bromophenyl) carbazole, 1g (3.2mmol) quinacridone, 0.68g (7.0mmol) sodium tert-butoxide, 222mg (0.19 mmol) palladium tetrakistriphenylphosphine, 38mg (0.19mmol) tri-tert-butylphosphine and 50mL toluene, and the temperature of the reaction solution was raised to 100° C. for 18 hours under the protection of nitrogen. After the reaction was completed, cool to room temperature, remove the solvent under reduced pressure, extract three times with dichloromethane, dry, and separate by column chromatography (petroleum ether: dichloromethane=2:1) to obtain white intermediate 1 (0.55g, yield 61% ). MALDI-TOF-MS (m / z): 794.13; 1 H NMR (400MHz, CDCl 3 ,δ):8.55(d,2H),8.19(d,2H),7.94(d,2H),7.69-7.70(m,6H),7.58(d,2H),7.51(s,2H),7.48- 7.50(m,4H),7....
Embodiment 2-4
[0044] The preparation method of the compounds M2, M3, and M4 of Examples 2-4 is the same as that of Example M1, the difference is that the substituents represented by R in R-Br are 2 to 4 to replace 1 in Example M1, and the specific process No longer.
[0045]
[0046] In order to better illustrate the performance of the thermally activated delayed fluorescence of the compounds of the present invention, the energy data of compounds M2, M3, and M4 in Examples 2-4 were obtained by calculating the simulation method as described in Example 1. For specific results, see Table 1 below.
[0047] Table 1
[0048]
[0049] As shown in Table 1: the excited singlet energy S of compounds M2, M3, and M4 1 and the excited triplet state energy T 1 The energy difference △E ST Between 0.06 and 0.10, all less than 0.2eV. Therefore, when the compounds M2, M3, and M4 are used as light-emitting materials, RISC can be realized, that is, triplet exciton reverse intersystem crossing transit...
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