Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes

A technology of organic compounds and derivatives, applied in the field of spirofluorene derivative organic compounds and their application in organic electroluminescent devices, can solve the problems of different performance

Inactive Publication Date: 2019-05-31
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes
  • Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes
  • Spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Embodiment 1: the synthesis of intermediate II and intermediate VI

[0077] a. Synthesis of Intermediate II

[0078]

[0079] (1) Weigh raw material A and dissolve it in acetic acid, cool down to 0°C with an ice-salt bath; weigh liquid bromine and dissolve it in glacial acetic acid, and slowly add it dropwise to the acetic acid solution of raw material A, stir at room temperature for 5 hours, and the sampling point plate, it shows that there is no remaining material A, and the reaction is complete; Distillate, through silica gel column, obtain raw material II; The mol ratio of described raw material A and liquid bromine is 1:1~1.5; The consumption of described acetic acid is that 0.01mol raw material A adds 20-40ml acetic acid;

[0080] Take the synthesis of intermediate II-1 as an example:

[0081]

[0082] (1) Add 0.01mol of raw material A-1 to a 100mL three-necked flask, dissolve 20ml of acetic acid, cool to 0°C with an ice-salt bath; add 0.8ml ( 0.015mol) l...

Embodiment 2

[0106] Embodiment 2: the synthesis of compound 1:

[0107]

[0108] (1) In a 500ml three-neck flask, under the protection of nitrogen, add 0.1mol raw material I-1, 0.12mol intermediate II-1, 0.3mol sodium tert-butoxide, 5×10 -4 mol Pd 2 (dba) 3 , 5×10 -4 mol tri-tert-butylphosphorus, dissolved in 300ml toluene, heated and refluxed for 24 hours, sampled and spotted on the plate, no raw material I-1 remained, and the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate III- 1, HPLC purity 99.8%, yield 80.5%. Elemental analysis structure (molecular formula C 39 h 25 NO 3 ): theoretical value C, 84.31; H, 4.54; N, 2.52; O, 8.64; test value: C, 84.32; H, 4.52; N, 2.53; ESI-MS(m / z)(M + ): The theoretical value is 555.18, and the measured value is 555.47.

[0109] (2) In a 500ml three-neck flask, under the protection of nitrogen, add 0.05mol of intermediate III-1, add 100ml of ...

Embodiment 3

[0112] Embodiment 3: the synthesis of compound 12:

[0113]

[0114] (1) In a 500ml three-neck flask, under the protection of nitrogen, add 0.1mol raw material I-1, 0.12mol intermediate II-2, 0.3mol sodium tert-butoxide, 5×10 -4 mol Pd 2 (dba) 3 , 5×10 -4 mol of tri-tert-butylphosphorus, dissolved in 300ml of toluene, heated to reflux for 24 hours, sampling point plate, showed that no raw material I-1 was left, and the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain intermediate III- 2. HPLC purity 99.4%, yield 82.1%. Elemental analysis structure (molecular formula C 39 h 25 NO 2 S): theoretical value C, 81.94; H, 4.41; N, 2.45; O, 5.60; S, 5.61; test value: C, 81.92; ESI-MS(m / z)(M + ): The theoretical value is 571.16, and the measured value is 571.48.

[0115] (2) In a 500ml three-neck flask, under the protection of nitrogen gas, add 0.05mol of intermediate III-2, add 100ml of ...

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Abstract

The invention relates to a spirofluorene derivative type organic compound and application thereof to organic light-emitting diodes (OLEDs). The spirofluorene derivative type organic compound has the advantages that spirofluorene is in loop connection with a nitrogen-containing six-membered heterocyclic structure through carbon-carbon double bonds, the loop connection through the carbon-carbon double bonds increases material chemical stability and avoids branch chain group active position exposure, and the whole molecule is a large rigid structure and has high triplet-state energy level (T1); adimethyl acridine structure is large in steric hindrance, less prone to rotation and stable in three-dimensional space structure, and accordingly the compound is high in glass transition temperatureand molecular thermal stability; in addition, the HOMO and LUMO distribution positions of the compound are separated from each other, so that the compound has appropriate HOMO and LUMO energy level; after the compound is applied to the OLEDs, the light-emitting efficiency of the OLEDs can be effectively increased, and the service life of the OLEDs can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a spirofluorene derivative organic compound and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive an...

Claims

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Application Information

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IPC IPC(8): C07D491/107C07D495/10C07D221/20C07D471/10C07D498/10C07D265/34C07D279/14C07D513/10C07D241/38C09K11/06H01L51/50H01L51/54
Inventor 王立春唐丹丹李崇张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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