Compound, display panels and display devices

Abstract

The invention belongs to the technical field of OLEDs and provides a compound used as an OLED hole transport material and an electron blocking material. The compound has a general formula structure asshown in [chemical formula 1], wherein Ar1 and Ar2 are respectively and independently selected from hydrogen atoms, and substituted or unsubstituted C5-C40 aryl, and m and n are respectively and independently selected from 0, 1 and 2; in [Chemical Formula 1], X is selected from O atom, S atom, or -NR-, R is selected from hydrogen, a substituted or unsubstituted C5-C40 aryl group; Ar3 has a structure represented by [Chemical Formula 2]; in [Chemical Formula 2], R1-R8 are each independently selected from hydrogen, substituted or unsubstituted C5-C40 aryl; Y is selected from O atom, S atom or -NR '-; and R' is selected from hydrogen, substituted or unsubstituted C5-C40 aryl. The hole transport material provided by the invention not only has triarylamine groups of traditional hole transport materials, can adjust material LUMO energy level, but also contains electron donating groups which are relatively weak electron donating groups, so that molecules are relatively high in HOMO energy level, and hole transport capability is effectively improved.

Description

technical field

[0001] The invention belongs to the field of OLED technology, and in particular relates to a compound mainly used as a hole transport material and an electron blocking material, a display panel and a display device comprising the compound. Background technique

[0002] Many small and medium-sized OLED screens such as mobile phone consumer products use R, G, and B sub-pixel display methods. In order to improve the production yield, some functional layers are often designed as common layers, which can reduce the use of FMM (fine metal mask), and the hole transport layer often uses a common layer, and the general public hole transport layer can be used in the market. sales materials.

[0003] Existing hole-transport material technologies suffer from several problems. One is that the solubility of the material is not good, which will lead to poor cleaning effect of the evaporation mask during mass production; the other is that the mobility of the material is to...

Examples

Embodiment approach

[0032] According to one embodiment of the compound of the present invention, the compound has a structure shown in [Chemical Formula 1-1]:

[0033]

[0034] Wherein, X is selected from O or S.

[0035] According to one embodiment of the compound of the present invention, the compound has a structure shown in [Chemical Formula 1-2]:

[0036]

[0037] Wherein, X is -NR-, and R is selected from hydrogen or phenyl.

[0038] According to one embodiment of the compound of the present invention, in [Chemical Formula 1], Ar 1 and Ar 2 are independently selected from a hydrogen atom or a phenyl group.

[0039] When Ar 1 and Ar 2 When it is hydrogen and phenyl, the molecular synthesis is relatively simple. In addition, increasing or decreasing the number of phenyl groups can effectively adjust the HOMO value of molecules to match different material systems.

[0040] According to one embodiment of the compound of the present invention, in [Chemical Formula 1], m and n are ea...

Embodiment 1

[0065] Synthesis of compound HT007

[0066]

[0067] In a 250ml round bottom flask, 1-bromo-4-iodo-9-phenyl-9H-carbazole (12mmol), 3-dibenzofuranboronic acid (10mmol) and Na 2 CO 3 (80mmol) was added to toluene / EtOH (absolute ethanol) / H 2 In O (75 / 25 / 50, mL) solvent, a mixed solution was formed, and then Pd(PPh 3 ) 4 (0.48mmol) was added in the above-mentioned mixed solution, carried out reflux reaction under nitrogen atmosphere 20 hours and the intermediate obtained was cooled to room temperature, added in water, filtered through diatomaceous earth pad then, extracted with dichloromethane simultaneously, washed with water then, And dried over anhydrous magnesium sulfate, filtered and evaporated, the crude product was purified by silica gel column chromatography to obtain the intermediate product HT007-1.

[0068] In a 250 ml round bottom flask, the intermediate product HT007-1 (12 mmol), cuprous iodide (15 mmol), potassium tert-butoxide (65 mmol), 1,2-diaminocyclohexan...

Embodiment 2

[0071] Synthesis of compound HT012

[0072]

[0073] In a 250ml round bottom flask, 1-bromo-4-iodo-9-phenyl-9H-carbazole (12mmol), 1-dibenzofuranboronic acid (10mmol) and Na 2 CO 3 (80mmol) was added to toluene / EtOH (absolute ethanol) / H 2 In O (75 / 25 / 50, mL) solvent, a mixed solution was formed, and then Pd(PPh 3 ) 4 (0.48mmol) was added in the above-mentioned mixed solution, carried out reflux reaction under nitrogen atmosphere 20 hours and the intermediate obtained was cooled to room temperature, added in water, filtered through diatomaceous earth pad then, extracted with dichloromethane simultaneously, washed with water then, And dried with anhydrous magnesium sulfate, filtered and evaporated, the crude product was purified by silica gel column chromatography to obtain the intermediate product HT012-1.

[0074] In a 250ml round bottom flask, the intermediate product HT012-1 (12mmol), cuprous iodide (15mmol), potassium tert-butoxide (65mmol), 1,2-diaminocyclohexane (1...

technical field

[0001] The invention belongs to the field of OLED technology, and in particular relates to a compound mainly used as a hole transport material and an electron blocking material, a display panel and a display device comprising the compound. Background technique

[0002] Many small and medium-sized OLED screens such as mobile phone consumer products use R, G, and B sub-pixel display methods. In order to improve the production yield, some functional layers are often designed as common layers, which can reduce the use of FMM (fine metal mask), and the hole transport layer often uses a common layer, and the general public hole transport layer can be used in the market. sales materials.

[0003] Existing hole-transport material technologies suffer from several problems. One is that the solubility of the material is not good, which will lead to poor cleaning effect of the evaporation mask during mass production; the other is that the mobility of the material is to...

Examples

Embodiment approach

[0032] According to one embodiment of the compound of the present invention, the compound has a structure shown in [Chemical Formula 1-1]:

[0033]

[0034] Wherein, X is selected from O or S.

[0035] According to one embodiment of the compound of the present invention, the compound has a structure shown in [Chemical Formula 1-2]:

[0036]

[0037] Wherein, X is -NR-, and R is selected from hydrogen or phenyl.

[0038] According to one embodiment of the compound of the present invention, in [Chemical Formula 1], Ar 1 and Ar 2 are independently selected from a hydrogen atom or a phenyl group.

[0039] When Ar 1 and Ar 2 When it is hydrogen and phenyl, the molecular synthesis is relatively simple. In addition, increasing or decreasing the number of phenyl groups can effectively adjust the HOMO value of molecules to match different material systems.

[0040] According to one embodiment of the compound of the present invention, in [Chemical Formula 1], m and n are ea...

Embodiment 1

[0065] Synthesis of compound HT007

[0066]

[0067] In a 250ml round bottom flask, 1-bromo-4-iodo-9-phenyl-9H-carbazole (12mmol), 3-dibenzofuranboronic acid (10mmol) and Na 2 CO 3 (80mmol) was added to toluene / EtOH (absolute ethanol) / H 2 In O (75 / 25 / 50, mL) solvent, a mixed solution was formed, and then Pd(PPh 3 ) 4 (0.48mmol) was added in the above-mentioned mixed solution, carried out reflux reaction under nitrogen atmosphere 20 hours and the intermediate obtained was cooled to room temperature, added in water, filtered through diatomaceous earth pad then, extracted with dichloromethane simultaneously, washed with water then, And dried over anhydrous magnesium sulfate, filtered and evaporated, the crude product was purified by silica gel column chromatography to obtain the intermediate product HT007-1.

[0068] In a 250 ml round bottom flask, the intermediate product HT007-1 (12 mmol), cuprous iodide (15 mmol), potassium tert-butoxide (65 mmol), 1,2-diaminocyclohexan...

Embodiment 2

[0071] Synthesis of compound HT012

[0072]

[0073] In a 250ml round bottom flask, 1-bromo-4-iodo-9-phenyl-9H-carbazole (12mmol), 1-dibenzofuranboronic acid (10mmol) and Na 2 CO 3 (80mmol) was added to toluene / EtOH (absolute ethanol) / H 2 In O (75 / 25 / 50, mL) solvent, a mixed solution was formed, and then Pd(PPh 3 ) 4 (0.48mmol) was added in the above-mentioned mixed solution, carried out reflux reaction under nitrogen atmosphere 20 hours and the intermediate obtained was cooled to room temperature, added in water, filtered through diatomaceous earth pad then, extracted with dichloromethane simultaneously, washed with water then, And dried with anhydrous magnesium sulfate, filtered and evaporated, the crude product was purified by silica gel column chromatography to obtain the intermediate product HT012-1.

[0074] In a 250ml round bottom flask, the intermediate product HT012-1 (12mmol), cuprous iodide (15mmol), potassium tert-butoxide (65mmol), 1,2-diaminocyclohexane (1...

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