Precursors of organometallic compounds for electroluminescent materials
A technology of electroluminescent materials and luminescent materials, which is applied in the direction of luminescent materials, electroluminescent light sources, electric light sources, etc., and can solve the problems of metal complex conductivity and luminous efficiency limitations
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Synthetic example 1
[0077] [Synthesis Example 1] Synthesis of DPBT
[0078]
[0079] p-Diaminobenzidine (1.0 g, 5.4 mmol) and potassium thiocyanate (2.4 g, 24.4 mmol) were added to 20 mL of acetic acid, and the resulting mixture was stirred at room temperature for 10 minutes. 0.5 mL (1 equivalent) of bromine was slowly added thereto, and the resulting mixture was stirred at room temperature for 2 hours. After stirring for 1 hour a yellow precipitate appeared. After the stirring was stopped, 20 mL of methanol was added to the reaction solution, and the resulting mixture was neutralized with a 0.1 N aqueous potassium hydroxide solution. 40 mL˜50 mL of distilled water was added to the neutralization reaction solution to obtain a solid formed, which was then filtered and washed with distilled water and methanol to obtain 1.2 g (4.1 mmol, yield: 75%) of an intermediate. This intermediate was added to 15 mL of 2,3-butanediol, and the mixture was heated to form a solution. Excess potassium hydroxi...
Synthetic example 2
[0085] [Synthesis Example 2] Synthesis of Zn-DPBT
[0086]
[0087] DPBT (0.9 g, 2.0 mmol) prepared in Synthesis Example 1 was added to 30 mL of methanol, and sodium hydroxide (at least 0.5 equivalent) was added thereto. The mixture was stirred to form a solution. A solution of zinc(II) acetate (0.35 g, 2.2 mmol) dissolved in 5 mL of methanol was slowly added to the reaction mixture, and the resulting mixture was stirred at room temperature for 2 hours. The resulting precipitate was filtered from the reaction solution, washed with 20 mL of distilled water, 50 mL of methanol and 10 mL of ether, and dried in vacuo to obtain a Zn(II) complex (Zn-DPBT) of the title compound DPBT (0.9 g, yield: 74%) ).
[0088] MS / FAB: 516, 1032, 1546 (measured).
Synthetic example 3
[0089] [Synthesis Example 3] Synthesis of DMBT
[0090]
[0091] Except using 3,3'-diaminobiphenyl-4,4'-dithiol (1.0g, 4.0mmol) as compound (112), repeat the same steps as in Synthesis Example 1 to obtain the title compound (133) (DMBT ) (0.75 g, 1.66 mmol, yield: 42%).
[0092] 1 H NMR (200MHz, CDCl 3 ): δ4.7(s, 2H), 6.8-7.1(m, 6H), 7.3(d, 2H), 7.8(d, 2H), 8.2(d, 2H), 8.4(s, 2H).
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