Silicon group containing 1, 4-phenylene vinylidene and its preparation method and use

Abstract

The invention is the method for preparing 1,4- containing silicon silicon group (Si-PPV) and its application. Compared with the present technology which has complex equipment, low lightening efficiency and unsatisfying heat stability, the invention uses polymer 3 as the raw material, generates 4 which then has coupling reaction with 6, generating 7, and the acquiring the active monomer through mole without water existence, the active monomer is changed into Si-PPV through Gilch reaction. The polymer has outstanding film-making performance, heat stability and lightening efficiency.

Description

field of invention

[0001] The invention discloses a class of silicon group-containing 1,4-phenylene vinylene with high luminous performance of electric field luminescence, ie Si-PPV, its preparation method and application. The polymer can be used in the fields of light-emitting devices, photovoltaic cells, light-emitting diodes and the like. Background of the invention

[0002] Since the 1990s, people have gained a better understanding of polymer electroluminescence. Electroluminescence is the process of converting electrical energy into light energy, that is, carrier double-injection luminescence. It has basically the same light-emitting mechanism as the ground tube, so they can also be regarded as a light-emitting diode: driven by the external voltage, the holes injected from the positive electrode and the electrons injected from the negative electrode are respectively transported to the light-emitting layer and Recombination occurs to release energy, and then the energy...

Examples

Embodiment 1

[0036] Example 1 Synthesis of 2,5-bis(bismethoxyoctylsilyl)-PPV: the structural formula is as follows:

[0037]

[0038] (1) Synthesis of 1,4-bis(bismethoxyoctylsilyl)benzene: 10.0 grams (42mmol) of p-dibromobenzene was dissolved in 100ml of anhydrous tetrahydrofuran, and N 2 For protection, 50ml (100mmol) of 2M freshly prepared n-butyllithium tetrahydrofuran solution was slowly added dropwise at -78°C, and after maintaining the temperature for 3 hours, 20g (84mmol) dimethoxyoctane was slowly added dropwise at -78°C Chlorosilane, after 2 hours of reaction, the temperature was slowly raised to room temperature within 3 hours, and the reaction was completed at room temperature for 6 hours. The reactant was washed with water, dried and distilled under reduced pressure to obtain the product. Boiling point: 173°C / 0.2mmHg.

[0039] The analytical results of the product are as follows:

[0040] 1 H NMR (R3DR3l3 ): δ (ppm) 7.08 (4H, singlet, R1r-H), 1.45-1.15 (24H, multiplet), ...

Embodiment 2

[0049] Example 2 Synthesis of 2,5-bis(methoxybutoxyoctylsilyl)-PPV: the structural formula is as follows:

[0050]

[0051] (1) Synthesis of 1,4-bis(methoxybutoxyoctylsilyl)benzene: 10.0 grams of p-dibromobenzene (42mmol) were dissolved in 500ml of anhydrous tetrahydrofuran, passed into N 2 For protection, 100ml (200mmol) of 2M freshly prepared n-propyllithium tetrahydrofuran solution was slowly added dropwise at -70°C, and the reaction was maintained at this temperature for 3 hours. 40 g (142 mmol) of methoxybutoxyoctylchlorosilane was slowly added dropwise at -70°C, and after 2 hours of reaction, the temperature was slowly raised to room temperature within 3 hours, and the reaction was completed at room temperature for 12 hours. The reactant was washed with water, dried and distilled under reduced pressure to obtain the product. Boiling point: 181°C / 0.2mmHg.

[0052] The analytical results of the product are as follows:

[0053] 1 H NMR (R3DR3l 3 ): δ (ppm) 7.06 (4H,...

Embodiment 3

[0062] Example 3 Synthesis of 2,5-bis(methyloctyloctadecylsilyl)-PPV: the structural formula is as follows:

[0063]

[0064] (1) Synthesis of 1,4-bis(methyloctyloctadecylsilyl)benzene: 10.0 grams (42mmol) of p-dibromobenzene are dissolved in 200ml of anhydrous tetrahydrofuran, and N 2 For protection, 120ml (240mmol) of fresh 2M isooctyllithium tetrahydrofuran solution was slowly added dropwise at -80°C, and the reaction was maintained at this temperature for 8 hours. Slowly add 130 g (292 mmol) of methyloctyloctadecylchlorosilane dropwise at -80°C. After 5 hours of reaction, the temperature is slowly raised to room temperature within 3 hours, and the reaction is completed at room temperature for 12 hours. The reactant was washed with water, dried and distilled under reduced pressure to obtain the product. Boiling point: 168°C / 0.1mmHg.

[0065] The analytical results of the product are as follows:

[0066] 1 H NMR (R3DR3l 3 ): δ (ppm) 7.23 (4H, singlet, R1r-H), 1.50-1....

field of invention

[0001] The invention discloses a class of silicon group-containing 1,4-phenylene vinylene with high luminous performance of electric field luminescence, ie Si-PPV, its preparation method and application. The polymer can be used in the fields of light-emitting devices, photovoltaic cells, light-emitting diodes and the like. Background of the invention

[0002] Since the 1990s, people have gained a better understanding of polymer electroluminescence. Electroluminescence is the process of converting electrical energy into light energy, that is, carrier double-injection luminescence. It has basically the same light-emitting mechanism as the ground tube, so they can also be regarded as a light-emitting diode: driven by the external voltage, the holes injected from the positive electrode and the electrons injected from the negative electrode are respectively transported to the light-emitting layer and Recombination occurs to release energy, and then the energy...

Examples

Embodiment 1

[0036] Example 1 Synthesis of 2,5-bis(bismethoxyoctylsilyl)-PPV: the structural formula is as follows:

[0037]

[0038] (1) Synthesis of 1,4-bis(bismethoxyoctylsilyl)benzene: 10.0 grams (42mmol) of p-dibromobenzene was dissolved in 100ml of anhydrous tetrahydrofuran, and N 2 For protection, 50ml (100mmol) of 2M freshly prepared n-butyllithium tetrahydrofuran solution was slowly added dropwise at -78°C, and after maintaining the temperature for 3 hours, 20g (84mmol) dimethoxyoctane was slowly added dropwise at -78°C Chlorosilane, after 2 hours of reaction, the temperature was slowly raised to room temperature within 3 hours, and the reaction was completed at room temperature for 6 hours. The reactant was washed with water, dried and distilled under reduced pressure to obtain the product. Boiling point: 173°C / 0.2mmHg.

[0039] The analytical results of the product are as follows:

[0040] 1 H NMR (R3DR3l3 ): δ (ppm) 7.08 (4H, singlet, R1r-H), 1.45-1.15 (24H, multiplet), ...

Embodiment 2

[0049] Example 2 Synthesis of 2,5-bis(methoxybutoxyoctylsilyl)-PPV: the structural formula is as follows:

[0050]

[0051] (1) Synthesis of 1,4-bis(methoxybutoxyoctylsilyl)benzene: 10.0 grams of p-dibromobenzene (42mmol) were dissolved in 500ml of anhydrous tetrahydrofuran, passed into N 2 For protection, 100ml (200mmol) of 2M freshly prepared n-propyllithium tetrahydrofuran solution was slowly added dropwise at -70°C, and the reaction was maintained at this temperature for 3 hours. 40 g (142 mmol) of methoxybutoxyoctylchlorosilane was slowly added dropwise at -70°C, and after 2 hours of reaction, the temperature was slowly raised to room temperature within 3 hours, and the reaction was completed at room temperature for 12 hours. The reactant was washed with water, dried and distilled under reduced pressure to obtain the product. Boiling point: 181°C / 0.2mmHg.

[0052] The analytical results of the product are as follows:

[0053] 1 H NMR (R3DR3l 3 ): δ (ppm) 7.06 (4H,...

Embodiment 3

[0062] Example 3 Synthesis of 2,5-bis(methyloctyloctadecylsilyl)-PPV: the structural formula is as follows:

[0063]

[0064] (1) Synthesis of 1,4-bis(methyloctyloctadecylsilyl)benzene: 10.0 grams (42mmol) of p-dibromobenzene are dissolved in 200ml of anhydrous tetrahydrofuran, and N 2 For protection, 120ml (240mmol) of fresh 2M isooctyllithium tetrahydrofuran solution was slowly added dropwise at -80°C, and the reaction was maintained at this temperature for 8 hours. Slowly add 130 g (292 mmol) of methyloctyloctadecylchlorosilane dropwise at -80°C. After 5 hours of reaction, the temperature is slowly raised to room temperature within 3 hours, and the reaction is completed at room temperature for 12 hours. The reactant was washed with water, dried and distilled under reduced pressure to obtain the product. Boiling point: 168°C / 0.1mmHg.

[0065] The analytical results of the product are as follows:

[0066] 1 H NMR (R3DR3l 3 ): δ (ppm) 7.23 (4H, singlet, R1r-H), 1.50-1....

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