Organic electrogenerated orange red light-emitting material and preparation method thereof

Abstract

The invention discloses an organic electrogenerated orange red light-emitting material and a preparation method thereof. The organic electrogenerated orange red light-emitting material has a general structural formula shown in the patent specification, wherein x is in a range of 0.01 to 0.5. The preparation method comprises the following steps that 2,7-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene, 2,7-dibromo-9,9-dioctylfluorene and 2,7-di(5-bromo-2-thienyl)-9-fluorenone are mixed according to a mole ratio of 100: (0 to 98): (2 to 100); and the mixture is added with tetrakis(triphenylphosphine)palladium and methyl trioctyl ammonium chloride and then undergoes a reaction in toluene and a sodium carbonate solution having the content of 2mol / L at a temperature of 60 to 120 DEG C in a nitrogen protective atmosphere under the conditions of backflow and stirring to produce the organic electrogenerated orange red light-emitting material. A device prepared from the organic electrogenerated orange red light-emitting material and having a structure of ITO / PEDOT / the organic electrogenerated orange red light-emitting material / Ca / Al has an electrogenerated orange red light-emitting characteristic. In an electrogenerated light-emitting spectrum of the organic electrogenerated orange red light-emitting material, an obvious orange red light peak exists.

Description

technical field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic electroluminescent material, in particular to an electroluminescent polymer material capable of emitting orange-red light, and a preparation method of the organic electroluminescent material. Background technique

[0002] Organic electroluminescent device (OLED) is a new type of flat display device, which has the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, long life, light weight and thin thickness.

[0003] In 1990, Burroughs et al. at the University of Cambridge reported the electroluminescence of poly(p-phenylene vinylene) (PPV) for the first time. Due to the characteristics of simple process and easy realization of large-screen display and flexible display, people have become more interested in electroluminescent polymer materials and devices, and a series of in-depth res...

Examples

Embodiment 1

[0026] Example 1: Synthesis of an organic electroluminescent orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 10% of the total molar weight of the polymer (x=0.1)

[0027] 1) Synthesis of 2,7-dibromo-9,9-dioctylfluorene

[0028]

[0029] Add 200mL of dimethyl sulfoxide and 14g of 2,7-dibromofluorene into a three-necked flask, stir to dissolve 2,7-dibromofluorene, raise the temperature to 75°C, add 0.12g of tetrabutylammonium bromide, 50wt% hydrogen Sodium oxide solution 50mL, stir to dissolve completely, add 1-bromooctane 20g, stir and react for 24h to obtain a mixed solution;

[0030] Dilute the mixed solution with 100 mL of ethyl acetate, wash with deionized water 3 times, add 50 mL of water each time, stir and wash for 25 min, and extract to obtain a light yellow organic phase solution;

[0031] Add 30 g of desiccant anhydrous magnesium sulfate to the light yellow solution, stir for 25 minutes, and filter to obtain a light yellow liquid;...

Embodiment 2

[0052] Example 2: Synthesis of an organic electro-orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 5% of the total molar weight of the polymer (x=0.05)

[0053] In a three-necked flask, 0.9 mmol (0.494 g) of 2,7-dibromo-9,9-dioctylfluorene, 2,7-bis(4,4,5,5-tetramethyl-1,3, 2-dioxaborane-diyl)-9,9-dioctylfluorene 1mmol (0.478g), 2,7-bis(5-bromo-2-thiophene)-9-fluorenone 0.1mmol (0.050g ), then add tetrakis (triphenylphosphine) palladium 0.023g, toluene 10mL, methyl trioctyl ammonium chloride 1mL, 2mol / L sodium carbonate solution 30mL, in 40cm 3 Nitrogen gas was introduced at a speed of 1 / min, the temperature was raised to 80°C, and the reaction was heated and stirred under reflux for 48 hours;

[0054] Pour the reaction solution into methanol and stir for 25min, precipitate out, filter to obtain an orange-red solid; add 200mL of 2mol / L hydrochloric acid solution to the orange-red solid, stir, then add 50mL of chloroform, extract, collect the or...

Embodiment 3

[0056] Example 3: Synthesis of an organic electro-orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 1% of the total molar weight of the polymer (x=0.01)

[0057] In the three-necked flask, 0.98 mmol (0.537 g) of 2,7-dibromo-9,9-dioctylfluorene, 2,7-bis(4,4,5,5-tetramethyl-1,3, 2-dioxaborane-diyl)-9,9-dioctylfluorene 1mmol (0.478g), 2,7-bis(5-bromo-2-thiophene)-9-fluorenone 0.02mmol (0.010g ), then add tetrakis (triphenylphosphine) palladium 0.023g, toluene 10mL, methyl trioctyl ammonium chloride 1mL, 2mol / L sodium carbonate solution 30mL, in 40cm 3 Nitrogen gas was introduced at a speed of 1 / min, the temperature was raised to 80°C, and the reaction was heated and stirred under reflux for 48 hours;

[0058] Pour the reaction solution into methanol and stir for 25min, precipitate out, filter to obtain a dark red solid; add 200mL of 2mol / L hydrochloric acid solution to the dark red solid, stir, then add 50mL of chloroform, extract, collect the org...

technical field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic electroluminescent material, in particular to an electroluminescent polymer material capable of emitting orange-red light, and a preparation method of the organic electroluminescent material. Background technique

[0002] Organic electroluminescent device (OLED) is a new type of flat display device, which has the characteristics of energy saving, fast response, stable color, strong environmental adaptability, no radiation, long life, light weight and thin thickness.

[0003] In 1990, Burroughs et al. at the University of Cambridge reported the electroluminescence of poly(p-phenylene vinylene) (PPV) for the first time. Due to the characteristics of simple process and easy realization of large-screen display and flexible display, people have become more interested in electroluminescent polymer materials and devices, and a series of in-depth res...

Examples

Embodiment 1

[0026] Example 1: Synthesis of an organic electroluminescent orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 10% of the total molar weight of the polymer (x=0.1)

[0027] 1) Synthesis of 2,7-dibromo-9,9-dioctylfluorene

[0028]

[0029] Add 200mL of dimethyl sulfoxide and 14g of 2,7-dibromofluorene into a three-necked flask, stir to dissolve 2,7-dibromofluorene, raise the temperature to 75°C, add 0.12g of tetrabutylammonium bromide, 50wt% hydrogen Sodium oxide solution 50mL, stir to dissolve completely, add 1-bromooctane 20g, stir and react for 24h to obtain a mixed solution;

[0030] Dilute the mixed solution with 100 mL of ethyl acetate, wash with deionized water 3 times, add 50 mL of water each time, stir and wash for 25 min, and extract to obtain a light yellow organic phase solution;

[0031] Add 30 g of desiccant anhydrous magnesium sulfate to the light yellow solution, stir for 25 minutes, and filter to obtain a light yellow liquid;...

Embodiment 2

[0052] Example 2: Synthesis of an organic electro-orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 5% of the total molar weight of the polymer (x=0.05)

[0053] In a three-necked flask, 0.9 mmol (0.494 g) of 2,7-dibromo-9,9-dioctylfluorene, 2,7-bis(4,4,5,5-tetramethyl-1,3, 2-dioxaborane-diyl)-9,9-dioctylfluorene 1mmol (0.478g), 2,7-bis(5-bromo-2-thiophene)-9-fluorenone 0.1mmol (0.050g ), then add tetrakis (triphenylphosphine) palladium 0.023g, toluene 10mL, methyl trioctyl ammonium chloride 1mL, 2mol / L sodium carbonate solution 30mL, in 40cm 3 Nitrogen gas was introduced at a speed of 1 / min, the temperature was raised to 80°C, and the reaction was heated and stirred under reflux for 48 hours;

[0054] Pour the reaction solution into methanol and stir for 25min, precipitate out, filter to obtain an orange-red solid; add 200mL of 2mol / L hydrochloric acid solution to the orange-red solid, stir, then add 50mL of chloroform, extract, collect the or...

Embodiment 3

[0056] Example 3: Synthesis of an organic electro-orange-red light material in which 2,7-bis(2-thiophene)-9-fluorenone accounts for 1% of the total molar weight of the polymer (x=0.01)

[0057] In the three-necked flask, 0.98 mmol (0.537 g) of 2,7-dibromo-9,9-dioctylfluorene, 2,7-bis(4,4,5,5-tetramethyl-1,3, 2-dioxaborane-diyl)-9,9-dioctylfluorene 1mmol (0.478g), 2,7-bis(5-bromo-2-thiophene)-9-fluorenone 0.02mmol (0.010g ), then add tetrakis (triphenylphosphine) palladium 0.023g, toluene 10mL, methyl trioctyl ammonium chloride 1mL, 2mol / L sodium carbonate solution 30mL, in 40cm 3 Nitrogen gas was introduced at a speed of 1 / min, the temperature was raised to 80°C, and the reaction was heated and stirred under reflux for 48 hours;

[0058] Pour the reaction solution into methanol and stir for 25min, precipitate out, filter to obtain a dark red solid; add 200mL of 2mol / L hydrochloric acid solution to the dark red solid, stir, then add 50mL of chloroform, extract, collect the org...

Images