Arylamine compound and organic electroluminescent element

An arylamine compound, electromechanical technology, applied in the field of arylamine compounds and organic electroluminescent elements, can solve the problems of low driving voltage luminous efficiency, unexpectable luminous efficiency, insufficient electron barrier, etc. Excellent, excellent electron blocking ability, good injection characteristics

CN114867713APending Publication Date: 2022-08-05HODOGOYA CHEMICAL CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2022-08-05

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Abstract

The purpose of the present invention is to provide, as a material for high-efficiency and high-durability organic EL elements, a material for organic EL elements, which has excellent hole injection / transport performance, electron blocking ability, high stability in a thin film state, and excellent durability, and to provide a high-efficiency and high-durability organic EL element using the compound. The present invention is an arylamine compound represented by general formula (1). (In the formula, Ar1, Ar2, Ar3 and Ar4 represent a substituted or unsubstituted aromatic hydrocarbon group or the like, L1 and L2 represent a divalent substituted or unsubstituted aromatic hydrocarbon group or the like, R1 to R7 represent a hydrogen atom or a heavy hydrogen atom or the like, m and n represent integers of 0 to 2, which may be the same as or different from each other, L1 represents a single bond when m is 0, and L2 represents a single bond when n is 0. )
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Description

Technical field

[0001] The present invention involves the compounds and components that are suitable for the organic electrical glow elements (hereinafter referred to as organic EL components) suitable for the optical components that are suitable for various display devices. Organic EL component. Background technique

[0002] Organic EL components are spontaneous optical components. Therefore, compared with LCD components, it is bright and visual. It can be displayed sharply, so active research is conducted.

[0003] In 1987, C.W.tang, Eastman Kodak, developed a layered structure component that divided various functions to various materials, which made organic EL elements using organic materials into practical components. They will be able to transmit electronics fluorescent body and organic objects that can be transmitted to the ground, and inject the charge of the two into the layer of the fluorescent body to glow, thereby using the voltage below 10V 2 The above high brightness...

Examples

Embodiment 1

[0107]

[0108] Incorporate 2,4,6-triangular-bromoly: 7.0g, double (couplet-4-base)-[3- (4, 4, 5, 5-four-in-four bases- [1 , 3, 2] -The bonitrine-2-base) -Bhenyl] -Anamin: 12.4g, [1, 1'-dual (two phenylbenyl) Ermao Iron] 钯 (II) Dichloride · dichloromethane additive: 0.3g, sodium bicarbonate: 3.6g, in THF / H 2 O mixed solvent will stir the next night. After natural cooling, add ethyl acetate / h to the system 2 O, remove the organic layer through extraction and liquid operation, concentrate, and obtain rough products. By refining the obtained crude products through the column chromatography (carrier: silicone, elute: dichloromethane / orthopedane), obtain double (colon-4-yield)-(3 ', 5'-two benzene base -1,1, 1,: 2, '1 "-triple benzene-3" -Base) -The white powder of amine (compound (58)): 9.5g (income: 74.5 %).

[0109] [化 2]

[0110]

[0111] For the obtained white powder, the NMR identification structure is used.

[0112] use 1 H-nmr ​​(CDCL 3 ) Detect the following 39 hydrogen sig...

Embodiment 2

[0115]

[0116] Incorporate 2,4,6-triangular-bromybenzene: 10.0g, (Lianzhen-4-Ya)-(4-萘 -1-base-phenyl)-[3- (4, 4, 4, 4,5,5-four-meta-[1, 3, 2] -The bonitrine boron-2-base) -Phenyl] -Amine: 22.3g, [1, 1'-double (bignene Bidthyl) Ermao Iron] 二 (II) dichlorophmony · Dichlorimlanide bonus: 0.4g, sodium bicarbonate: 5.1g, in THF / H 2 O mixed solvent will stir the next night. After natural cooling, add ethyl acetate / h to the system 2 O, the organic layer is removed by extraction and liquid operation, and the organic layer is concentrated to obtain crude products. By refining the obtained crude products through the column chromatography (carrier: silicone, elute: dichloromethane / orthopedane), obtain (lin benzene-4-yield)-(3 ', 5'-two phenyl- 1, 1 ': 2', 1 "-triple benzene-3" -Base)-(4-萘 -1-yl-phenyl) -The white powder with amine (compound (59)): 16.0g : 82.0 %).

[0117] [化 3]

[0118]

[0119] For the obtained white powder, the NMR identification structure is used.

[0120] use 1 H-nm...

Embodiment 3

[0123]

[0124] Incorporate 2,4,6-triangular-bromybenzene: 11.0g, (linked benzene-4-yield)-(4-萘 -2-base-phenyl)-[3- (4, 4, 4, 4,5,5-four-in-four bases- [1, 3, 2] -The bonitrine boron-2-base) -Phenyl] -Amine: 24.6g, [1, 1'-double (bignene Bidth) Ermao Iron] 二 (II) dichlorophmony · dichloromethane bonus: 0.5g, sodium bicarbonate: 5.6g, in THF / H 2O mixed solvent will stir the next night. After natural cooling, add ethyl acetate / h to the system 2 O, the organic layer is removed by extraction and liquid operation, and the organic layer is concentrated to obtain crude products. By refining the obtained crude products through the column chromatography (carrier: silicone, elute: dichloromethane / orthopedane), obtain (lin benzene-4-yield)-(3 ', 5'-two phenyl- 1, 1 ': 2', 1 "-trisopene-3" -The)-(4-萘 -2-base-phenyl) -The white powder (compound (60)): 15.5g : 72.0 %).

[0125] [化 4]

[0126]

[0127] For the obtained white powder, the NMR identification structure is used.

[0128] use 1 H-n...