Organic light-emitting material using pyrene nitride as core and having TADF characteristic, and organic electroluminescent device thereof
A luminescent material and luminescent technology, applied in luminescent materials, electrical solid devices, electrical components, etc., can solve the problems of unbalanced carrier transport, small electron transport rate, and reduced quantum efficiency, so as to improve luminous efficiency and improve Effect of Injection and Transport Capability, Improving Fluorescence Quantum Efficiency
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Embodiment 1
[0025] This embodiment provides a method for preparing an organic luminescent material M1 with TADF characteristics with pyrene as the core, and the specific steps are as follows:
[0026] (1) Preparation of intermediate compound C:
[0027]
[0028] Add 7.15g (50mol) of compound A, 5g (50mol) of triethylamine and 150mL of dichloromethane into a 250ml three-necked flask in sequence, and after cooling down to 0°C in an ice bath, slowly dropwise add the compound A dissolved in 50mL of dichloromethane with a constant pressure dropping funnel. 8.68g (20mol) of compound B in methane, after the dropwise addition, was raised to room temperature and stirred for 18h. After the reaction was complete, it was quenched by adding ice water, extracted three times with dichloromethane, the organic phases were combined, the organic solvent was removed by rotary evaporation, and the product C (7.24 g, yield 55%) was obtained by recrystallization with toluene / ethanol.
[0029] MALDI-TOF (m / z...
Embodiment 2-4
[0041] Examples 2-4 are the preparation methods of compounds M2, M3 and M4 respectively, the preparation methods of which are similar to those of M1 in the example, and the specific process will not be repeated here.
[0042] In order to better illustrate that the organic luminescent material of the present invention has thermally induced delayed fluorescence properties, the energy data of compounds M2, M3 and M4 were obtained by calculating the simulation method as described in Example 1, and the specific results are shown in Table 1.
[0043] Table 1 Physical test data of organic luminescent materials M1, M2, M3 and M4
[0044]
[0045] It can be seen from Table 1 that the HOMO energy levels of the organic luminescent materials M2, M3 and M4 with TADF characteristics centered on azopyrene are -5.40, -5.45 and -5.31eV, and the LUMO energy levels are -2.36 and -5.31eV, respectively. 2.32, -2.27eV; Excited singlet energies S of M2, M3 and M4 1 Respectively 2.54, 2.72, 2.58e...
Embodiment 5
[0047] Embodiment 5: organic electroluminescence device:
[0048] The four kinds of organic luminescent materials M1, M2, M3 and M4 with TADF characteristics in Examples 1-4 of the present invention as the core are respectively used as light-emitting objects, and the blue light material ADN is used as the main body, and are applied to doped organic light-emitting materials. In electroluminescent devices, the device structure and energy levels are as follows figure 2 As shown, the device includes: conductive glass (ITO) substrate layer 1, hole injection layer 2 (poly3,4-ethylenedioxythiophene: polystyrene sulfonate, PEDOT: PSS), hole transport layer 3 (4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline], TAPC), light-emitting layer 4 (the host material is ADN(9,10-bis(β-naphthyl)anthracene ), the guest material adopts the organic luminescent material M1, M2, M3 or M4 of embodiment 1-4), the electron transport layer 5 (1,3,5-three (1-phenyl-1H-benzimidazol-2-yl ) benzene, TPBI...
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