Organic photoelectric functional material and organic light-emitting device prepared from same

Abstract

The invention relates to an organic photoelectric functional material based on an aromatic ring pyridopyrazine structure as a parent nucleus, and a long-life and high-efficiency organic light-emittingdevice prepared by using the organic photoelectric functional material as an electron transport material and a thermal activation delayed red light guest material, and belongs to the technical fieldof organic photoelectric functional materials. The structural general formula of the material is shown as (I), wherein R1 and R2 are C6-C14 aryl or Ra-substituted C6-C14 aryl, 5-24-membered heteroarylor Ra-substituted 5-24-membered heteroaryl, aromatic amino or Ra-substituted aromatic amino; ring A is a benzene ring group, an acenaphthene ring group, a phenanthrene ring group, or a 1, 10-azaphenanthrene ring group.

Description

Technical field

[0001] The present invention belongs to the technical field of organic photoelectric function materials, and in particular, an organic photoelectric function material based on an aromatic ring and pyridine and a pyrazine structure is a mother-core, and an organic electrical or electrical electrical or electrical electrical or electrically activated delayed red light material is applied. LED.Background technique

[0002] Organic Light Emitting Diode, OLEDs have the advantages of high efficiency, low levels of enhancement, viewing angle, have become a new generation of display and lighting technology. With the wide application of OLEDs in the field of smartphones, TV, wearables, in the past ten years, East Asia Three Kingdoms (China, Japan, South Korea) invests in the OLED panel production lines have reached trillion yuan. Although the OLED materials and devices have been widely studied and concerned in the scientific community and the industry, the maximum external quantum ...

Examples

preparation Embodiment 1

[0078]Table 1. Preparation Example Product Data Summary:

[0079]

[0080]1,2-benzoquinone or pyroxal or phenanthrene or 1,10-phenanthridine-5,6-diketone and 2-bromipate-3,4 diamine and / or 5-bromipate-3, 4 Diamine is added to acetic acid in accordance with the ratio of molar ratio 1: 1, and after cooling to room temperature, the reaction liquid is poured into water, filtered, washed with water and methanol, and the resulting filter cake is vacuum dry, resulting in 1 - and / or 4-bromoic benzopyrazine.

[0081]1- and / or 4-bromine benzopyridine and the intermediate reactants were reacted with a one-step reaction or two steps in nitrogen in nitrogen, and potassium carbonate, four in the water, and water in nitrogen and water according to the molar ratio 1: 1.1. (Trobenzylphosphine) palladium refluxed 24 hours, then cooled to room temperature, filtered to room temperature, and water was added to the filtrate, and the organic phase was extracted with dichloromethane, separated from the organi...

preparation Embodiment 2

[0094]Table 2. Preparation Example Product Data Summary:

[0095]

[0096]

[0097]

[0098]

[0099]1,2-benzoquinone or pyroxal or phenanthrene or 1,10-phenanthridine-5,6-diketone and 2-bromipate-3,4 diamine and / or 5-bromipate-3, 4 Diamine is added to acetic acid in accordance with the ratio of molar ratio 1: 1, and after cooling to room temperature, the reaction liquid is poured into water, filtered, washed with water and methanol, and the resulting filter cake is vacuum dry, resulting in 1 - and / or 4-bromoic benzopyrazine.

[0100]1- and / or 4-bromine benzopyridine and the intermediate reactants were reacted with a one-step reaction or two steps in nitrogen in nitrogen, and potassium carbonate, four in the water, and water in nitrogen and water according to the molar ratio 1: 1.1. (Triphenylphosphine) palladium reflux 24 hours, then cooled to room temperature, filtered the reaction liquid, adding water to the filtrate, extract organic phase with dichloromethane, separating the organic phase a...

preparation Embodiment 3

[0113]Table 3. Preparation Example Product Data Summary:

[0114]

[0115]

[0116]

[0117]

[0118]1,2-benzoquinone or pyroxal or phenanthrene or 1,10-phenanthridine-5,6-diketone and 2-bromipate-3,4 diamine and / or 5-bromipate-3, 4 Diamine is added to acetic acid in accordance with the ratio of molar ratio 1: 1, and after cooling to room temperature, the reaction liquid is poured into water, filtered, washed with water and methanol, and the resulting filter cake is vacuum dry, resulting in 1 - and / or 4-bromoic benzopyrazine.

[0119]1- and / or 4-bromogeneous benzopyridine and the intermediate reactants were taken in nitric acid under the protection of nitrogen by the molar ratio 1: 1.1 by the molar ratio 1: 1.1. Rurium, bis (dibenzyl acetone) palladium and tri-butylphosphine were added after 24 hours, then cooled to room temperature, filtered the reaction liquid, and water was added to the filtrate, and the organic phase was extracted with dichloromethane, separated After the organic phase was ...

Technical field

[0001] The present invention belongs to the technical field of organic photoelectric function materials, and in particular, an organic photoelectric function material based on an aromatic ring and pyridine and a pyrazine structure is a mother-core, and an organic electrical or electrical electrical or electrical electrical or electrically activated delayed red light material is applied. LED.Background technique

[0002] Organic Light Emitting Diode, OLEDs have the advantages of high efficiency, low levels of enhancement, viewing angle, have become a new generation of display and lighting technology. With the wide application of OLEDs in the field of smartphones, TV, wearables, in the past ten years, East Asia Three Kingdoms (China, Japan, South Korea) invests in the OLED panel production lines have reached trillion yuan. Although the OLED materials and devices have been widely studied and concerned in the scientific community and the industry, the maximum external quantum ...

Examples

preparation Embodiment 1

[0078]Table 1. Preparation Example Product Data Summary:

[0079]

[0080]1,2-benzoquinone or pyroxal or phenanthrene or 1,10-phenanthridine-5,6-diketone and 2-bromipate-3,4 diamine and / or 5-bromipate-3, 4 Diamine is added to acetic acid in accordance with the ratio of molar ratio 1: 1, and after cooling to room temperature, the reaction liquid is poured into water, filtered, washed with water and methanol, and the resulting filter cake is vacuum dry, resulting in 1 - and / or 4-bromoic benzopyrazine.

[0081]1- and / or 4-bromine benzopyridine and the intermediate reactants were reacted with a one-step reaction or two steps in nitrogen in nitrogen, and potassium carbonate, four in the water, and water in nitrogen and water according to the molar ratio 1: 1.1. (Trobenzylphosphine) palladium refluxed 24 hours, then cooled to room temperature, filtered to room temperature, and water was added to the filtrate, and the organic phase was extracted with dichloromethane, separated from the organi...

preparation Embodiment 2

[0094]Table 2. Preparation Example Product Data Summary:

[0095]

[0096]

[0097]

[0098]

[0099]1,2-benzoquinone or pyroxal or phenanthrene or 1,10-phenanthridine-5,6-diketone and 2-bromipate-3,4 diamine and / or 5-bromipate-3, 4 Diamine is added to acetic acid in accordance with the ratio of molar ratio 1: 1, and after cooling to room temperature, the reaction liquid is poured into water, filtered, washed with water and methanol, and the resulting filter cake is vacuum dry, resulting in 1 - and / or 4-bromoic benzopyrazine.

[0100]1- and / or 4-bromine benzopyridine and the intermediate reactants were reacted with a one-step reaction or two steps in nitrogen in nitrogen, and potassium carbonate, four in the water, and water in nitrogen and water according to the molar ratio 1: 1.1. (Triphenylphosphine) palladium reflux 24 hours, then cooled to room temperature, filtered the reaction liquid, adding water to the filtrate, extract organic phase with dichloromethane, separating the organic phase a...

preparation Embodiment 3

[0113]Table 3. Preparation Example Product Data Summary:

[0114]

[0115]

[0116]

[0117]

[0118]1,2-benzoquinone or pyroxal or phenanthrene or 1,10-phenanthridine-5,6-diketone and 2-bromipate-3,4 diamine and / or 5-bromipate-3, 4 Diamine is added to acetic acid in accordance with the ratio of molar ratio 1: 1, and after cooling to room temperature, the reaction liquid is poured into water, filtered, washed with water and methanol, and the resulting filter cake is vacuum dry, resulting in 1 - and / or 4-bromoic benzopyrazine.

[0119]1- and / or 4-bromogeneous benzopyridine and the intermediate reactants were taken in nitric acid under the protection of nitrogen by the molar ratio 1: 1.1 by the molar ratio 1: 1.1. Rurium, bis (dibenzyl acetone) palladium and tri-butylphosphine were added after 24 hours, then cooled to room temperature, filtered the reaction liquid, and water was added to the filtrate, and the organic phase was extracted with dichloromethane, separated After the organic phase was ...

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