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An aromatic amine compound and its organic electroluminescent device

A compound and aromatic amine technology, applied in the field of aromatic amine compounds and organic electroluminescent devices, can solve the problems of reduced luminous efficiency, shortened service life, unbalanced charge of the light-emitting layer, etc., to improve the refractive index and prolong the use The effect of low life and aging rate

Active Publication Date: 2021-04-27
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As far as the current OLED devices are concerned, since the hole transport material should have a low highest occupied molecular orbital (HOMO) value, most of them have a low triplet energy level (T1) value, which makes the The excitons are transferred to the interface of the hole transport layer or to the side of the hole transport layer, causing the charge imbalance in the light-emitting layer, resulting in light emission at the interface of the hole transport layer, and ultimately reducing the luminous efficiency and service life of the device

Method used

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  • An aromatic amine compound and its organic electroluminescent device
  • An aromatic amine compound and its organic electroluminescent device
  • An aromatic amine compound and its organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0073] Preparation of intermediate M1:

[0074]

[0075] Compound A1 and compound Y1 undergo a C-N coupling reaction under the conditions of base, catalyst and ligand to obtain intermediate M1;

[0076] Preparation of intermediate M2:

[0077]

[0078] Compound A2 and compound Y2 undergo a C-N coupling reaction under the conditions of base, catalyst and ligand to obtain intermediate M2;

[0079] The preparation of arylamine compound shown in general formula (I):

[0080]

[0081] The intermediate M1 and the intermediate M2 undergo a C-N coupling reaction under conditions such as a base and a catalyst to obtain an arylamine compound represented by the general formula (I).

[0082] Wherein, said X is selected from O or S,

[0083] The L is selected from one of a single bond, a substituted or unsubstituted arylene group with 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group with 3 to 12 carbon atoms,

[0084] The L 1 , L 2 one independently sel...

Synthetic example 1

[0104] Synthesis Example 1: Synthesis of Compound 1

[0105]

[0106] Synthesis of intermediate M1-1: under an argon atmosphere, successively add Y1-1 (2.95g, 12mmol) and A1-1 (1.69g, 10mmol) and 50ml toluene, then add sodium tert-butoxide (1.44g , 15mmol), Pd 2 (dba) 3 (0.46g, 0.5mmol) and tri-tert-butylphosphine (0.1g, 0.5mmol), stirred and heated to reflux, and reacted for 24 hours; after the reaction, cooled to room temperature, filtered, and the filtrate was distilled under reduced pressure, and then passed through the column layer Purified by analysis to obtain intermediate M1-1 (2.98g, 8.9mmol), with a HPLC purity of 99.4% and a yield of 89%.

[0107] Synthesis of intermediate M2-1: To the system of Y2-1 (3.73g, 10mmol) and A2-1 (2.54g, 15mmol) dissolved in toluene (85ml), add Pd in ​​sequence 2 (dba) 3 (0.28g, 0.3mmol), tri-tert-butylphosphine (0.12g, 0.6mmol) and sodium tert-butoxide (2.88g, 30mmol), heated to 100°C, and reacted for 12 hours; after the reaction...

Synthetic example 2

[0109] Synthesis Example 2: Synthesis of Compound 13

[0110]

[0111]

[0112] The raw materials and intermediates in Synthesis Example 1 were converted accordingly, and according to the synthesis method of Compound 1 in Synthesis Example 1, Compound 13 was obtained, with an HPLC purity of 99.5% and a yield of 76%. Mass Spectrum m / z: 895.03 (calculated: 894.09). Theoretical element content (%)C 66 h 43 N 3O: C, 88.66; H, 4.85; N, 4.70; O, 1.79. Actual element content (%): C, 88.59; H, 4.83; N, 4.75; O, 1.85. 1 H NMR (600MHz, CDCl 3 )(δ,ppm):9.60(dd,1H),8.63(dd,1H),8.51(dd,1H),8.33(dd,1H),8.07(d,1H),7.97(d,1H),7.80 (d,1H),7.79-7.67(m,7H),7.66-7.61(m,3H),7.55(dd,1H),7.52(dd,2H),7.28-7.22(m,11H),7.19(dd ,1H),7.16(d,1H),7.11(t,1H),7.10-7.06(m,3H),7.02-6.98(m,3H),6.67(dd,1H),6.52(td,1H), 6.46(td,1H).

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Abstract

The invention provides an aromatic amine compound and an organic electroluminescence device thereof, belonging to the technical field of organic photoelectric materials. In order to achieve better light emission inside the light-emitting layer, thereby improving the luminous efficiency and service life of the device, the present invention provides an aromatic amine compound with a high glass transition temperature, which is located between the light-emitting layer and the hole transport layer The HOMO value and high T1 value, when it is applied to the device as a luminescence auxiliary layer, can effectively improve the luminous efficiency and service life of the device, and at the same time reduce the driving voltage of the device. Therefore, the aromatic amine compound provided by the invention is a kind of OLED material with excellent performance.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound and an organic electroluminescence device thereof. Background technique [0002] Organic Light-Emitting Diode (hereinafter referred to as OLED), with its small thickness, light weight, wide viewing angle, short response time, good low temperature characteristics, simple manufacturing process, low cost, high luminous efficiency, and energy consumption The advantages of low weight and good bendability have attracted the attention of major display companies and material companies around the world. [0003] The light-emitting mechanism of OLED is: driven by an external electric field, electrons and holes are injected from the cathode and anode to the organic layer sandwiched between the two electrodes, and then from the electron transport layer and the hole transport layer to the light-emitting layer respectively. Migration, and the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D405/10C07D405/14C07D409/04C07D409/10C07D409/14C07D413/14C07D417/14H01L51/54H01L51/50
CPCC07D405/04C07D405/14C07D405/10C07D413/14C07D409/14C07D409/10C07D417/14C07D409/04H10K85/622H10K85/624H10K85/626H10K85/636H10K85/633H10K85/656H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K30/865H10K50/15
Inventor 朱鸫达鲁秋邵钰杰孙月
Owner CHANGCHUN HYPERIONS TECH CO LTD
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