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Compound having indenocarbazole ring structure, and organic electroluminescent element
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A component and organic technology, applied in the field of compounds with indenocarbazole ring structure and organic electroluminescence components, can solve the problems of current efficiency, insufficient component life and the like
Active Publication Date: 2020-06-19
HODOGOYA CHEMICAL CO LTD
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[0014]
In devices using these compounds for the hole transport layer and the light emitting layer, there are too many electrons in the light emitting layer, and the current efficiency and device life are not sufficient.
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Embodiment 1
[0246]
[0247] Into the nitrogen-substituted reaction vessel, add 18.5 g of N-(9,9-dimethyl-9H-fluoren-2-yl)-2-bromo-aniline, 6.98 g of potassium acetate, and 95 ml of DMF, and let it flow for 1 hour nitrogen. 1.18 g of tetrakis(triphenylphosphine)palladium was added, heated, and stirred at 100° C. for 11 hours. After cooling to room temperature, the reaction liquid was poured into 300 ml of water, and extracted with 300 ml of toluene. The organic layer was repeatedly washed twice with 200 ml of water, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product. The crude product is purified by column chromatography (carrier: silica gel, eluent: toluene / n-hexane) to obtain 12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole 7.9 g of light yellow powder (yield 55.2%).
[0248] The obtained 12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole 7.8g was mixed with iodobenzene 3.7ml, sodium bisulfite 0.43g, copper powder 0....
Embodiment 2
[0255]
[0256] In the reaction vessel replaced by nitrogen, add the 7-bromo-12,12-dimethyl-10-phenyl-10,12-dihydroindeno[2,1-b]carbazole synthesized in Example 1 2.0 g, 1.32 g of 4-diphenylamino-phenylboronic acid, 15 ml of a mixed solvent of toluene / ethanol (4 / 1, v / v), 3.4 ml of 2M potassium carbonate aqueous solution, and nitrogen gas for 30 minutes while irradiating ultrasonic waves. 0.26 g of tetrakis(triphenylphosphine)palladium was added, heated, and stirred at 73° C. for 5 hours. After cooling to room temperature, 30 ml of toluene and 20 ml of water were added for liquid separation, and the organic layer was collected. The organic layer was washed with saturated brine, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product. Purify the crude product by column chromatography (carrier: silica gel, eluent: toluene / n-hexane) to obtain 12,12-dimethyl-10-phenyl-7-(4-diphenylamino-phenyl) - 1.6 g of light yellowi...
Embodiment 3
[0261]
[0262] In the reaction vessel replaced by nitrogen, add the 7-bromo-12,12-dimethyl-10-phenyl-10,12-dihydro-indeno[2,1-b]carba synthesized in Example 1 Azole 3.0g, (biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl ]-Phenylamine 3.7g, toluene / ethanol (4 / 1, v / v) mixed solvent 50ml, 2M potassium carbonate aqueous solution 10ml, while irradiating ultrasonic waves, pass nitrogen gas for 30 minutes. 0.4 g of tetrakis(triphenylphosphine)palladium was added, heated, and stirred at 73° C. for 8 hours. After cooling to room temperature, the precipitated crude product was collected by filtration. 140 ml of 1,2-dichlorobenzene was added to the crude product and dissolved while heating, and the insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. Purified by recrystallization using 100 ml of 1,2-dichlorobenzene to obtain 7-[4-{(biphenyl-4-yl)-phenylamino}-phenyl]-12,12-dimethyl - 2.7 g of white powder of 10...
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Abstract
The purpose of the present invention is to provide an organic compound for use as a material in a highly efficient and highly durable organic electroluminescent element, said compound exhibiting superior hole injection and transport performance, having an electron blocking ability, and exhibiting superior properties such as high stability and light emission efficiency when in a thin-film form, andto provide a highly efficient and highly durable organic electroluminescent element using said compound. An organic electroluminescent element characterized by comprising, between a positive electrode and a negative electrode, at least a first hole transport layer, a second hole transport layer, a green light-emitting layer and an electron transport layer in the given order from the positive electrode side, wherein the second hole transport layer or at least one layer among the stacked films disposed between the electron transport layer and the first hole transport layer includes a compound having an indenocarbazole ring structure represented by general formula (1). (In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon, a substituted or unsubstituted aromatic hetero-cycle, or a substituted or unsubstituted divalent polycyclic aromatic group; Ar1, Ar2 and Ar3 may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted polycyclic aromatic group; A and Ar2 or Ar2 and Ar3 may form a ring via a single bond, or may form a ring by mutually bonding to a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom; R1-R9 may be the same or different, represent a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an optionally-substituted C1-6 linear or branched alkyl group, an optionally-substituted C5-10 cycloalkyl group, an optionally-substituted C2-6 linear or branched alkenyl group, an optionally-substituted C1-6 linear or branched alkyloxy group, an optionally-substituted C5-10 cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbongroup, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, and may form a ring via asingle bond, or may form a ring by mutually bonding to a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom; and R10 and R11 may be the same or different, represent an optionally-substituted C1-6 linear or branched alkyl group, an optionally-substituted C5-10 cycloalkyl group, an optionally-substituted C2-6 linear or branched alkenyl group, an optionally-substituted C1-6 linear or branched alkyloxy group, an optionally-substituted C5-10 cycloalkyloxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted polycyclic aromatic group or a substituted or unsubstituted aryloxy group, and may form a ring via a single bond, or may form a ring by mutually bonding to a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom.)
Description
technical field [0001] The present invention relates to compounds suitable for use in organic electroluminescence elements (hereinafter simply referred to as organic EL elements) as self-luminous elements suitable for various display devices and the elements, and specifically relates to compounds having an indenocarbazole ring structure. A compound and an organic EL device using the compound. Background technique [0002] Since the organic EL element is a self-luminous element, compared with a liquid crystal element, it is bright and has excellent visibility and can perform a clear display, so active research has been conducted. [0003] In 1987, C.W.Tang of Eastman Kodak Company developed a layered structure element in which various functions are distributed to each material, thus making organic EL elements using organic materials a practical element. They will be able to transport electrons phosphor, tris (8-hydroxyquinoline) aluminum (hereinafter referred to as Alq 3 ) ...
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