Host material based on naphtho five-membered heterocycle and benzo five-membered heterocycle, preparation method of host material and organic light-emitting device
A five-membered heterocycle and host material technology, which is applied in the manufacture of electrical solid state devices, semiconductor devices, semiconductor/solid state devices, etc., can solve the problems of low triplet state energy level and poor stability, and achieve high and stable triplet state energy level The effect of good nature and high chemical stability
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Embodiment 1
[0060] This example provides a host material based on a naphtho five-membered heterocyclic benzo five-membered heterocyclic ring, which is denoted as compound 1. The synthetic route of compound 1 is as follows:
[0061]
[0062] The synthetic method of compound 1 specifically comprises the following steps:
[0063] Synthesis of Intermediate 1: 15.8g (0.1mol) of raw material 1 was dissolved in 500mL of tetrahydrofuran, 69.6g (0.4mol) of sodium dithionite was dissolved in 200mL of water to prepare a suspension, and this suspension was added to The above tetrahydrofuran containing raw material 1 was isolated from air and stirred at room temperature for 2 hours to obtain a mixed solution containing intermediate 1.
[0064] Synthesis of Intermediate 2: At room temperature, add 100 mL of potassium hydroxide solution (10 mol / L) dropwise to the above mixed solution, after stirring for 1 hour, add 38.7 mL (0.4 mol) of dimethyl sulfate dropwise, and continue at room temperature Stir...
Embodiment 2
[0071] This example provides a host material based on a naphtho five-membered heterocyclic benzo five-membered heterocyclic ring, which is denoted as compound 49. The synthetic route of compound 49 is as follows:
[0072]
[0073] The synthetic method of compound 49 specifically comprises the following steps:
[0074] Synthesis of Intermediate 1-6: Same as Example 1.
[0075] Synthesis of intermediate 7: under a nitrogen atmosphere, 200ml toluene, 100ml water and 50ml ethanol were added to a 500mL flask and mixed, then 8g (0.014mol) of intermediate 6, 3.16g (0.015mol) of raw material 3, 5.81g ( 0.042mol) of potassium carbonate and 0.51g (0.0007mol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride were reacted at 100°C for 12 hours. After concentration, it was purified by chromatographic column to obtain intermediate 7 (5.75 g, yield 82.4%). 1 H NMR (500MHz, CDCl 3 )δ8.25(dd, J=7.5,1.4Hz,1H),8.05–7.96(m,2H),7.86–7.80(m,1H),7.57(dtd,J=27.3,7.7,1.3Hz,2H) ,7.52...
Embodiment 3
[0078] This example provides a host material based on a naphtho five-membered heterocyclic benzo five-membered heterocyclic ring, which is denoted as compound 13. The synthetic route of compound 13 is as follows:
[0079]
[0080] The synthetic method of compound 13 specifically comprises the following steps:
[0081] Synthesis of Intermediate 1-6: Same as Example 1.
[0082] Synthesis of compound 13: under a nitrogen atmosphere, 80ml of toluene, 40ml of water and 20ml of ethanol were added to a 2500mL flask and mixed, then 4.56g (0.008mol) of intermediate 6, 5.9g (0.018mol) of raw material 5, 3.3 (0.024 mol) potassium carbonate and 0.73g (0.001mol) [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, reacted at 100°C for 12 hours, concentrated and purified by chromatographic column to obtain the compound 6 (4.57 g, 84.7% yield). 1 H NMR (500MHz, CDCl 3)δ8.68(d,J=1.6Hz,1H),8.52(d,J=1.4Hz,1H),8.28–8.23(m,0H),8.18–8.12(m,2H),7.98–7.82(m ,5H), 7.57–7.41(m,2H).
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