Organic light-emitting material containing tetraphenylbenzene, preparation and application

Abstract

The invention belongs to the field of organic optoelectronic materials, and discloses an organic light-emitting material containing tetraphenylbenzene, preparation and application. The structural formula of the organic light-emitting material containing the tetraphenylbenzene is shown in the formula I, wherein R1 is an aromatic nucleus derivative electron-donating group, and R2 is an aromatic nucleus derivative electron-withdrawing group. The preparation method comprises the steps that 1,4-dibromo-2.5-terphenyl and R2-substituted phenylboronic acid are used as raw materials, and an aromatic nucleus compound containing the R2 is obtained through a Suzuki reaction; under the action of a tetrakispalladium catalyst, the aromatic nucleus compound containing the R2 and R1-substituted phenylboronic acid or borate are reacted, and the organic light-emitting material containing the tetraphenylbenzene is obtained. The organic light-emitting material containing the tetraphenylbenzene has the advantages of efficient solid-state lighting and double polarity, and the organic light-emitting material can be used for preparing an organic light-emitting device which is high in efficiency, low in roll-off degree and non-doped with blue light.

Description

technical field

[0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to an organic luminescent material containing tetraphenylbenzene and its preparation and application. Background technique

[0002] With the rise and vigorous development of the organic electronics industry, organic optoelectronic materials have been widely used in the field of organic light-emitting diodes, and have now become a rapidly growing field in materials science due to their important scientific research value and broad commercial application prospects . Exploring and developing organic light-emitting materials with better performance, high luminous efficiency, and adjustable emission wavelength is a problem that researchers need to solve urgently. However, the development of efficient luminescent materials is quite difficult, because traditional materials will cause their luminescence to be quenched in the aggregated state. Contents of the inv...

Examples

Embodiment 1

[0034] The preparation of the organic electroluminescent material (TPA-TPB-CN) containing tetraphenylbenzene in this embodiment:

[0035]

[0036] The synthetic route is as follows:

[0037]

[0038] (1) P-bromoterphenyl (compound 1) (6g, 15.5mmol), 4-cyanophenylboronic acid (compound 2) (2.50g, 17.0mmol), anhydrous potassium carbonate (6.4g, 46.5mmol) and Pd (PPh 3 ) 4 (895mg, 0.8mmol) was added to a 250mL reaction flask, under nitrogen protection, 105mL THF and 15mL water were added, refluxed overnight, after the reaction was cooled, it was extracted with dichloromethane, concentrated and then powdered and passed through the column to obtain a white solid 3 with a yield of 73 %;

[0039] (2) Intermediate 3 (2.136g, 1.5mmol), triphenylamine 4-phenylboronic acid (compound 4) (1.6g, 3.9mmol), anhydrous potassium carbonate (1.616g, 11.7mmol) and Pd (PPh 3 ) 4 (225mg, 0.195mmol) was added to a 250mL reaction flask, under the protection of nitrogen, 10mL THF and 5mL wat...

Embodiment 2

[0042] Preparation of the organic electroluminescent material (Cz-TPB-CN) containing tetraphenylbenzene in this embodiment

[0043]

[0044] The synthetic route is as follows:

[0045]

[0046] Intermediate 3 (2.136g, 1.5mmol), 4-boronic acid carbazole (compound 5) (1.119g, 3.9mmol), anhydrous potassium carbonate (1.616g, 11.7mmol) and Pd (PPh 3 ) 4 (225mg, 0.195mmol) was added to a 250mL reaction flask, under the protection of nitrogen, 10mL THF and 5mL water were added, refluxed overnight, the reaction was cooled, extracted with dichloromethane, concentrated, powdered and passed through the column to obtain white solid Cz-TPB-CN , productive rate 86%; Product identification data are as follows:

[0047] 1 H NMR (500MHz, CD 2 Cl 2 ),δ(TMS,ppm):8.16(m,1H),8.14(m,1H),7.69(s,1H),7.58(d,2H),7.56(m,1H),7.47(d,4H) ,7.45-7.38(m,6H),7.35-7.25(m,12H).

Embodiment 3

[0049] Preparation of the organic electroluminescent material (3PhCz-TPB-CN) containing tetraphenylbenzene in this embodiment

[0050]

[0051] The synthetic route is as follows:

[0052]

[0053] Intermediate 3 (2.136g, 1.5mmol), compound 6 (1.415g, 3.9mmol), anhydrous potassium carbonate (1.616g, 11.7mmol) and Pd(PPh 3 ) 4 (225mg, 0.195mmol) was added to a 250mL reaction flask, under the protection of nitrogen, 10mL THF and 5mL water were added, refluxed overnight, after the reaction was cooled, it was extracted with dichloromethane, concentrated, powdered and passed through the column to obtain a white solid 3PhCz-TPB-CN , productive rate 84%; Product identification data are as follows:

[0054] 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm):8.35(d,1H),8.18(m,1H),7.59-7.66(m,8H),7.50(d,3H),7.47(m,4H),7.27-7.45( d,13H), 7.29(m,2H).

technical field

[0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to an organic luminescent material containing tetraphenylbenzene and its preparation and application. Background technique

[0002] With the rise and vigorous development of the organic electronics industry, organic optoelectronic materials have been widely used in the field of organic light-emitting diodes, and have now become a rapidly growing field in materials science due to their important scientific research value and broad commercial application prospects . Exploring and developing organic light-emitting materials with better performance, high luminous efficiency, and adjustable emission wavelength is a problem that researchers need to solve urgently. However, the development of efficient luminescent materials is quite difficult, because traditional materials will cause their luminescence to be quenched in the aggregated state. Contents of the inv...

Examples

Embodiment 1

[0034] The preparation of the organic electroluminescent material (TPA-TPB-CN) containing tetraphenylbenzene in this embodiment:

[0035]

[0036] The synthetic route is as follows:

[0037]

[0038] (1) P-bromoterphenyl (compound 1) (6g, 15.5mmol), 4-cyanophenylboronic acid (compound 2) (2.50g, 17.0mmol), anhydrous potassium carbonate (6.4g, 46.5mmol) and Pd (PPh 3 ) 4 (895mg, 0.8mmol) was added to a 250mL reaction flask, under nitrogen protection, 105mL THF and 15mL water were added, refluxed overnight, after the reaction was cooled, it was extracted with dichloromethane, concentrated and then powdered and passed through the column to obtain a white solid 3 with a yield of 73 %;

[0039] (2) Intermediate 3 (2.136g, 1.5mmol), triphenylamine 4-phenylboronic acid (compound 4) (1.6g, 3.9mmol), anhydrous potassium carbonate (1.616g, 11.7mmol) and Pd (PPh 3 ) 4 (225mg, 0.195mmol) was added to a 250mL reaction flask, under the protection of nitrogen, 10mL THF and 5mL wat...

Embodiment 2

[0042] Preparation of the organic electroluminescent material (Cz-TPB-CN) containing tetraphenylbenzene in this embodiment

[0043]

[0044] The synthetic route is as follows:

[0045]

[0046] Intermediate 3 (2.136g, 1.5mmol), 4-boronic acid carbazole (compound 5) (1.119g, 3.9mmol), anhydrous potassium carbonate (1.616g, 11.7mmol) and Pd (PPh 3 ) 4 (225mg, 0.195mmol) was added to a 250mL reaction flask, under the protection of nitrogen, 10mL THF and 5mL water were added, refluxed overnight, the reaction was cooled, extracted with dichloromethane, concentrated, powdered and passed through the column to obtain white solid Cz-TPB-CN , productive rate 86%; Product identification data are as follows:

[0047] 1 H NMR (500MHz, CD 2 Cl 2 ),δ(TMS,ppm):8.16(m,1H),8.14(m,1H),7.69(s,1H),7.58(d,2H),7.56(m,1H),7.47(d,4H) ,7.45-7.38(m,6H),7.35-7.25(m,12H).

Embodiment 3

[0049] Preparation of the organic electroluminescent material (3PhCz-TPB-CN) containing tetraphenylbenzene in this embodiment

[0050]

[0051] The synthetic route is as follows:

[0052]

[0053] Intermediate 3 (2.136g, 1.5mmol), compound 6 (1.415g, 3.9mmol), anhydrous potassium carbonate (1.616g, 11.7mmol) and Pd(PPh 3 ) 4 (225mg, 0.195mmol) was added to a 250mL reaction flask, under the protection of nitrogen, 10mL THF and 5mL water were added, refluxed overnight, after the reaction was cooled, it was extracted with dichloromethane, concentrated, powdered and passed through the column to obtain a white solid 3PhCz-TPB-CN , productive rate 84%; Product identification data are as follows:

[0054] 1 H NMR (500MHz, CDCl 3 ), δ(TMS,ppm):8.35(d,1H),8.18(m,1H),7.59-7.66(m,8H),7.50(d,3H),7.47(m,4H),7.27-7.45( d,13H), 7.29(m,2H).

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