Compound with 9-fluorenone as nucleus and application of same to OLED device

Abstract

The invention discloses a compound with 9-fluorenone as a nucleus and application of the same to an OLED device. The compound uses 9-fluorenone as the nucleus and has the characteristics that molecules are not prone to crystallization and aggregation and the compound has good film forming ability. Applied as a luminescent layer material to an organic light-emitting diode, the compound has good photoelectric performance and can better adapt to and meet application requirements of panel manufacturers.

Description

technical field

[0001] The invention relates to the technical field of semiconductors, in particular to a compound with 9-fluorenone as the core and its application as a light-emitting layer material in an organic light-emitting diode. Background technique

[0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect.

[0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OL...

Examples

Embodiment 1

[0063] Embodiment 1: the synthesis of compound 35:

[0064] synthetic route:

[0065]

[0066] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-9-fluorenone, 0.015mol intermediate A1, 0.03mol sodium tert-butoxide, 1×10 -4 molPd(dppf)Cl 2 , 180mL toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , the target product was obtained, the HPLC purity was 99.2%, and the yield was 74.7%.

[0067] Elemental analysis structure (molecular formula C 49 h 36 N 2 O): Theoretical C, 87.99; H, 5.43; N, 4.19; O, 2.39; Tested: C, 87.98; H, 5.45; N, 4.20;

[0068] HPLC-MS: The theoretical molecular weight of the material is 668.82, and the measured molecular weight is 669.04.

Embodiment 2

[0069] Embodiment 2: the synthesis of compound 37:

[0070] synthetic route:

[0071]

[0072] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 3-bromo-9-fluorenone, 0.015mol intermediate B1, 0.03mol sodium tert-butoxide, 1×10 -4 molPd(dppf)Cl 2 , 180mL toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , the target product was obtained, the HPLC purity was 99.4%, and the yield was 76.3%.

[0073] Elemental analysis structure (molecular formula C 46 h 30 N 2 O): Theoretical C, 88.15; H, 4.82; N, 4.47; O, 2.55; Tested: C, 88.14; H, 4.84; N, 4.46;

[0074] HPLC-MS: The theoretical molecular weight of the material is 626.74, and the measured molecular weight is 626.96.

Embodiment 3

[0075] Embodiment 3: the synthesis of compound 48:

[0076] synthetic route:

[0077]

[0078] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-9-fluorenone, 0.015mol intermediate C1, 0.03mol sodium tert-butoxide, 1×10 -4 molPd(dppf)Cl 2 , 180mL toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , the target product was obtained, the HPLC purity was 99.1%, and the yield was 78.6%.

[0079] Elemental analysis structure (molecular formula C 43 h 23 NO 3 ): theoretical value C, 85.84; H, 3.85; N, 2.33; O, 7.98; test value: C, 85.85; H, 3.86; N, 2.32;

[0080] HPLC-MS: The theoretical molecular weight of the material is 601.65, and the measured molecular weight is 601.88.

technical field

[0001] The invention relates to the technical field of semiconductors, in particular to a compound with 9-fluorenone as the core and its application as a light-emitting layer material in an organic light-emitting diode. Background technique

[0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect.

[0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OL...

Examples

Embodiment 1

[0063] Embodiment 1: the synthesis of compound 35:

[0064] synthetic route:

[0065]

[0066] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-9-fluorenone, 0.015mol intermediate A1, 0.03mol sodium tert-butoxide, 1×10 -4 molPd(dppf)Cl 2 , 180mL toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , the target product was obtained, the HPLC purity was 99.2%, and the yield was 74.7%.

[0067] Elemental analysis structure (molecular formula C 49 h 36 N 2 O): Theoretical C, 87.99; H, 5.43; N, 4.19; O, 2.39; Tested: C, 87.98; H, 5.45; N, 4.20;

[0068] HPLC-MS: The theoretical molecular weight of the material is 668.82, and the measured molecular weight is 669.04.

Embodiment 2

[0069] Embodiment 2: the synthesis of compound 37:

[0070] synthetic route:

[0071]

[0072] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 3-bromo-9-fluorenone, 0.015mol intermediate B1, 0.03mol sodium tert-butoxide, 1×10 -4 molPd(dppf)Cl 2 , 180mL toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , the target product was obtained, the HPLC purity was 99.4%, and the yield was 76.3%.

[0073] Elemental analysis structure (molecular formula C 46 h 30 N 2 O): Theoretical C, 88.15; H, 4.82; N, 4.47; O, 2.55; Tested: C, 88.14; H, 4.84; N, 4.46;

[0074] HPLC-MS: The theoretical molecular weight of the material is 626.74, and the measured molecular weight is 626.96.

Embodiment 3

[0075] Embodiment 3: the synthesis of compound 48:

[0076] synthetic route:

[0077]

[0078] In a 250mL three-neck flask, under a nitrogen atmosphere, add 0.01mol 2-bromo-9-fluorenone, 0.015mol intermediate C1, 0.03mol sodium tert-butoxide, 1×10 -4 molPd(dppf)Cl 2 , 180mL toluene, heated to reflux for 10 hours, sampled and spotted, the raw materials were completely reacted; naturally cooled to room temperature (20-25°C), filtered, and the filtrate was collected for vacuum rotary evaporation (-0.09MPa, 85°C), and column chromatography , the target product was obtained, the HPLC purity was 99.1%, and the yield was 78.6%.

[0079] Elemental analysis structure (molecular formula C 43 h 23 NO 3 ): theoretical value C, 85.84; H, 3.85; N, 2.33; O, 7.98; test value: C, 85.85; H, 3.86; N, 2.32;

[0080] HPLC-MS: The theoretical molecular weight of the material is 601.65, and the measured molecular weight is 601.88.

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