Compound taking dibenzocycloheptene as core and application of compound

Abstract

The invention discloses a compound taking dibenzocycloheptene as a core and applications of the compound, and belongs to the technical field of semiconductors. The structure of the compound provided by the invention is shown as general formula (1). The invention also discloses applications of the compound. The compound provided by the invention contains a dibenzocycloheptene structure, has relatively high glass-transition temperature and molecular thermal stability, and appropriate HOMO and LUMO energy levels, and can effectively improve the luminous efficiency of devices and prolong the service life of OLED devices after being applied to manufacturing of the OLED devices.

Description

technical field

[0001] The invention relates to a compound with dibenzocycloheptene as the core and application thereof, belonging to the technical field of semiconductors. Background technique

[0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can not only be used to manufacture new display products, but also can be used to make new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a very wide application prospect . The OLED light-emitting device is 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 OLED light-emitting device, and the positive and negative charg...

Examples

Embodiment 1

[0082] Embodiment 1: the synthesis of compound 1

[0083]

[0084] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate A1, 0.012mol raw material B1, 150ml toluene, stir and mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.1%, yield 82.7%;

[0085] Elemental analysis structure (molecular formula C 48 h 33 N): theoretical value C, 92.42; H, 5.33; N, 2.25; test value: C, 92.45; H, 5.35; N, 2.28. ESI-MS(m / z)(M + ): The theoretical value is 623.80, and the measured value is 623.87.

Embodiment 2

[0086] Embodiment 2: the synthesis of compound 5

[0087]

[0088] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate A1, 0.012mol raw material B2, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.3%, yield 82.7%;

[0089] Elemental analysis structure (molecular formula C 51 h 32 N 2 ): theoretical value C, 91.04; H, 4.79; N, 4.16; test value: C, 91.08; H, 4.83; N, 4.22. ESI-MS(m / z)(M + ): The theoretical value is 672.83, and the measured value is 672.88.

Embodiment 3

[0090] Embodiment 3: the synthesis of compound 27

[0091]

[0092] The preparation method of compound 27 is the same as that in Example 1, except that intermediate A1 is replaced by intermediate A2, and raw material B1 is replaced by raw material B3.

[0093] Elemental analysis structure (molecular formula C 45 h 27 NO): Theoretical C, 90.43; H, 4.55; N, 2.34; O, 2.68; Tested: C, 90.47; H, 4.59; N, 2.37; ESI-MS(m / z)(M + ): The theoretical value is 597.72, and the measured value is 597.76.

technical field

[0001] The invention relates to a compound with dibenzocycloheptene as the core and application thereof, belonging to the technical field of semiconductors. Background technique

[0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can not only be used to manufacture new display products, but also can be used to make new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a very wide application prospect . The OLED light-emitting device is 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 OLED light-emitting device, and the positive and negative charg...

Examples

Embodiment 1

[0082] Embodiment 1: the synthesis of compound 1

[0083]

[0084] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate A1, 0.012mol raw material B1, 150ml toluene, stir and mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.1%, yield 82.7%;

[0085] Elemental analysis structure (molecular formula C 48 h 33 N): theoretical value C, 92.42; H, 5.33; N, 2.25; test value: C, 92.45; H, 5.35; N, 2.28. ESI-MS(m / z)(M + ): The theoretical value is 623.80, and the measured value is 623.87.

Embodiment 2

[0086] Embodiment 2: the synthesis of compound 5

[0087]

[0088] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate A1, 0.012mol raw material B2, 150ml toluene and stir to mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 99.3%, yield 82.7%;

[0089] Elemental analysis structure (molecular formula C 51 h 32 N 2 ): theoretical value C, 91.04; H, 4.79; N, 4.16; test value: C, 91.08; H, 4.83; N, 4.22. ESI-MS(m / z)(M + ): The theoretical value is 672.83, and the measured value is 672.88.

Embodiment 3

[0090] Embodiment 3: the synthesis of compound 27

[0091]

[0092] The preparation method of compound 27 is the same as that in Example 1, except that intermediate A1 is replaced by intermediate A2, and raw material B1 is replaced by raw material B3.

[0093] Elemental analysis structure (molecular formula C 45 h 27 NO): Theoretical C, 90.43; H, 4.55; N, 2.34; O, 2.68; Tested: C, 90.47; H, 4.59; N, 2.37; ESI-MS(m / z)(M + ): The theoretical value is 597.72, and the measured value is 597.76.

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