Benzodiazaborole derivative and organic light-emitting diodes using the same

Abstract

A benzodiazaborole derivative has the structure of the following formula (1) as shown in the description, wherein R1 is selected from one of a group consisting of a hydrogen atom, a formula (2), a formula (3), and a formula (4), and R2 is selected from the group consisting of a hydrogen atom, a formula (3) and a formula (4), R1 is different from R2 and at least one of them is a hydrogen atom, R3 is a general formula (4) when R2 is a general formula (4), and R3 is a hydrogen atom or a general formula (3) When R2 is a hydrogen atom; R4 to R19 are independently selected from one group consistingof a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, a alkoxy group, a haloalkyl group, a sulfanyl group, a silyl group, and an alkenyl group.

Description

Technical field

[0001] The invention relates to a light-emitting material and a light-emitting element, in particular to a benzodiazepine compound and an organic light-emitting diode element.

Background technique

[0002] With the advancement of electronic technology, light-weight and high-efficiency flat-panel display devices are also booming. Organic electroluminescent devices are expected to become the mainstream of next-generation flat-panel display devices due to their advantages such as self-illumination, no viewing angle limitation, power saving, easy manufacturing process, low cost, high response speed, and full color.

[0003] Generally, an organic electroluminescence device includes an anode, an organic light emitting layer and a cathode. When a direct current is applied to the organic electroluminescent device, holes and electrons are injected into the organic light-emitting layer from the anode and the cathode respectively, and the potential difference cause...

Examples

Synthetic example 1

[0091] Synthesis Example 1: Preparation of Compound 1

[0092] Get 1,2-dibromobenzene (1,2-dibromobenzene, 1.50 g, 6.40 mmol), palladium acetate (Palladiumacetate, Pd(OAc) 2 , 0.04 g, 0.178 mmol), tri-tert-butylphosphonium tetrafluoroborate (Tri-tert-butylphosphonium tetrafluoroborate, 0.15 g, 0.52 mmol), sodium tert-butoxide (Sodium tert-butoxide, NaO t Bu, 1.82 g, 18.95 mmol) in a 50 ml double-necked flask, after pumping argon three times, inject toluene (Toluene, 20 ml) and aniline (Aniline, 1.70 ml, 18.65 mmol) that have dehydrated and deoxygenated, Reflux and react for 18 hours. After returning to room temperature, filter through diatomaceous earth and collect the filtrate, add ammonium chloride aqueous solution for extraction, dry the organic layer with anhydrous magnesium sulfate, and then suck it dry. Using n-hexane: dichloromethane = 4:1 as the eluent to perform column chromatography, 1.45 g of compound 1 was obtained as a white solid with a yield of 87%. The foreg...

Synthetic example 2

[0095] Synthesis Example 2: Preparation of Compound 2

[0096] Get 2,3-dichlorobromobenzene (1-bromo-2,3-dichlorobenzene, 1.00 g, 4.43 mmol), phenylboronic acid (Phenylboronic acid, 0.56 g, 4.60 mmol), potassium carbonate (Potassium carbonate, K 2 CO 3 , 1.38 g, 10.00 mmol), palladium chloride (Palladium (II) chloride, PdCl 2 , 4.00 mg, 0.02 mmol) were placed in a 100 ml single-necked bottle, and ethanol (Ethanol, 5 ml) and 15 ml of deionized water were added. After stirring at room temperature for half an hour, it was extracted with dichloromethane and potassium carbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and sucked dry. Column chromatography was performed using n-hexane as the eluent to obtain 0.80 g of compound 2 as a transparent liquid with a yield of 82%. The foregoing reaction is shown in reaction formula (2).

[0097] data analysis: 1 H NMR (400MHz, CDCl 3 ):δ7.44-7.37(m,6H),7.25-7.21(m,2H); 13 C NMR (100MHz, CDCl 3 ...

Synthetic example 3

[0099] Synthesis Example 3: Preparation of Compound 3

[0100]Take compound 2 (0.75 g, 3.38 mmol), three (dibenzylideneacetone) dipalladium (Bis (dibenzylideneacetone) palladium (0), Pd (dba) 2 , 0.19 g, 0.33 mmol), tri-tert-butylphosphonium tetrafluoroborate (Tri-tert-butylphosphonium tetrafluoroborate, 0.19 g, 0.66 mmol), sodium tert-butoxide (Sodium tert-butoxide, NaO t Bu, 0.95 g, 0.99 mmol) was placed in a 25 ml double-necked flask, and after argon was replaced three times, toluene (Toluene, 16 ml) and aniline (Aniline, 0.90 ml, 9.87 mmol) were injected , heated to 110° C. and reacted for 18 hours. After returning to room temperature, filter through diatomaceous earth and collect the filtrate, add ammonium chloride aqueous solution for extraction, dry the organic layer with anhydrous magnesium sulfate, and then suck it dry. Column chromatography was carried out using n-hexane:dichloromethane=4:1 as the eluent to obtain 0.83 g of compound 3 as a white solid with a yield ...

Technical field

[0001] The invention relates to a light-emitting material and a light-emitting element, in particular to a benzodiazepine compound and an organic light-emitting diode element.

Background technique

[0002] With the advancement of electronic technology, light-weight and high-efficiency flat-panel display devices are also booming. Organic electroluminescent devices are expected to become the mainstream of next-generation flat-panel display devices due to their advantages such as self-illumination, no viewing angle limitation, power saving, easy manufacturing process, low cost, high response speed, and full color.

[0003] Generally, an organic electroluminescence device includes an anode, an organic light emitting layer and a cathode. When a direct current is applied to the organic electroluminescent device, holes and electrons are injected into the organic light-emitting layer from the anode and the cathode respectively, and the potential difference cause...

Examples

Synthetic example 1

[0091] Synthesis Example 1: Preparation of Compound 1

[0092] Get 1,2-dibromobenzene (1,2-dibromobenzene, 1.50 g, 6.40 mmol), palladium acetate (Palladiumacetate, Pd(OAc) 2 , 0.04 g, 0.178 mmol), tri-tert-butylphosphonium tetrafluoroborate (Tri-tert-butylphosphonium tetrafluoroborate, 0.15 g, 0.52 mmol), sodium tert-butoxide (Sodium tert-butoxide, NaO t Bu, 1.82 g, 18.95 mmol) in a 50 ml double-necked flask, after pumping argon three times, inject toluene (Toluene, 20 ml) and aniline (Aniline, 1.70 ml, 18.65 mmol) that have dehydrated and deoxygenated, Reflux and react for 18 hours. After returning to room temperature, filter through diatomaceous earth and collect the filtrate, add ammonium chloride aqueous solution for extraction, dry the organic layer with anhydrous magnesium sulfate, and then suck it dry. Using n-hexane: dichloromethane = 4:1 as the eluent to perform column chromatography, 1.45 g of compound 1 was obtained as a white solid with a yield of 87%. The foreg...

Synthetic example 2

[0095] Synthesis Example 2: Preparation of Compound 2

[0096] Get 2,3-dichlorobromobenzene (1-bromo-2,3-dichlorobenzene, 1.00 g, 4.43 mmol), phenylboronic acid (Phenylboronic acid, 0.56 g, 4.60 mmol), potassium carbonate (Potassium carbonate, K 2 CO 3 , 1.38 g, 10.00 mmol), palladium chloride (Palladium (II) chloride, PdCl 2 , 4.00 mg, 0.02 mmol) were placed in a 100 ml single-necked bottle, and ethanol (Ethanol, 5 ml) and 15 ml of deionized water were added. After stirring at room temperature for half an hour, it was extracted with dichloromethane and potassium carbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and sucked dry. Column chromatography was performed using n-hexane as the eluent to obtain 0.80 g of compound 2 as a transparent liquid with a yield of 82%. The foregoing reaction is shown in reaction formula (2).

[0097] data analysis: 1 H NMR (400MHz, CDCl 3 ):δ7.44-7.37(m,6H),7.25-7.21(m,2H); 13 C NMR (100MHz, CDCl 3 ...

Synthetic example 3

[0099] Synthesis Example 3: Preparation of Compound 3

[0100]Take compound 2 (0.75 g, 3.38 mmol), three (dibenzylideneacetone) dipalladium (Bis (dibenzylideneacetone) palladium (0), Pd (dba) 2 , 0.19 g, 0.33 mmol), tri-tert-butylphosphonium tetrafluoroborate (Tri-tert-butylphosphonium tetrafluoroborate, 0.19 g, 0.66 mmol), sodium tert-butoxide (Sodium tert-butoxide, NaO t Bu, 0.95 g, 0.99 mmol) was placed in a 25 ml double-necked flask, and after argon was replaced three times, toluene (Toluene, 16 ml) and aniline (Aniline, 0.90 ml, 9.87 mmol) were injected , heated to 110° C. and reacted for 18 hours. After returning to room temperature, filter through diatomaceous earth and collect the filtrate, add ammonium chloride aqueous solution for extraction, dry the organic layer with anhydrous magnesium sulfate, and then suck it dry. Column chromatography was carried out using n-hexane:dichloromethane=4:1 as the eluent to obtain 0.83 g of compound 3 as a white solid with a yield ...

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