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Compound with spirodimethyl anthracene fluorene as core and application thereof in organic light emission diode device

A technology of spirodimethyl anthracene fluorene and compound, which can be applied to the application field of organic electroluminescence devices, and can solve problems such as disparity

Inactive Publication Date: 2019-04-05
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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  • Compound with spirodimethyl anthracene fluorene as core and application thereof in organic light emission diode device
  • Compound with spirodimethyl anthracene fluorene as core and application thereof in organic light emission diode device
  • Compound with spirodimethyl anthracene fluorene as core and application thereof in organic light emission diode device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Example 1 Compound 4

[0139]

[0140] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol of intermediate A1, 0.012mol of raw material B1, and 150ml of toluene, stir and mix, then add 0.03mol of sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol tri-tert-butylphosphine, heated to 105 ° C, refluxed for 24 hours, sampling point plate, showed that no bromine remained, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09 MPa, 85 ° C ), passed through a neutral silica gel column to obtain the target product, the HPLC purity was 99.3%, and the yield was 64.7%;

[0141] Elemental analysis structure (molecular formula C 43 H 35 N): Theoretical C, 91.29; H, 6.24; N, 2.48; Tested: C, 91.27; H, 6.25; N, 2.50. ESI-MS (m / z) (M+): theoretical value 565.28, found value 565.31.

Embodiment 2

[0142] Example 2 Compound 15

[0143]

[0144] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol intermediate A2, 0.012mol raw material B2, 150ml toluene, stir and mix, then add 0.03mol sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5 × 10-5mol tri-tert-butylphosphine, heated to 105 ° C, refluxed for 24 hours, sampling point plate, showed that no bromine remained, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to reduced pressure rotary evaporation (- 0.09MPa, 85°C), passed through a neutral silica gel column to obtain the target product, the HPLC purity was 99.3%, and the yield was 64.7%;

[0145] Elemental analysis structure (molecular formula C 40 H 29 NS): Theoretical C, 86.45; H, 5.26; N, 2.52; S, 5.77; Tested: C, 86.43; H, 5.21; N, 2.55; S, 5.75. ESI-MS (m / z) (M+): Theoretical value is 555.20, and the found value is 555.25.

Embodiment 3

[0146] Example 3 Compound 20

[0147]

[0148] In a 250ml three-necked flask, under the protection of nitrogen, add 0.01mol intermediate A3, 0.012mol raw material B3, 150ml toluene, stir and mix, then add 0.03mol sodium tert-butoxide, 5 × 10 -5 molPd 2 (dba) 3 , 5×10 -5 mol tri-tert-butylphosphine, heated to 105 ° C, refluxed for 24 hours, sampling point plate, showed that no bromine remained, the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09 MPa, 85 ° C ), passed through a neutral silica gel column to obtain the target product, the HPLC purity was 99.3%, and the yield was 64.7%;

[0149] Elemental analysis structure (molecular formula C 49 H 37 NO): Theoretical C, 89.74; H, 5.69; N, 2.14; O, 2.44; Tested: C, 89.72; H, 5.67; N, 2.15; O, 2.46. ESI-MS (m / z) (M+): theoretical value 655.29, found value 655.32.

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Abstract

The invention relates to a compound with spirodimethyl anthracene fluorene as a core and an application thereof in organic light emission diode device. A structure of the compound is shown as the following formula. The compound provided by the invention utilizes the spirodimethyl anthracene fluorene as a skeleton, a connecting branched branch is a dibenzo six-membered ring derivative structure, and since the strong and weak capability of a branched chain group giving an electron is different, an HOMO energy level of an overall structure of the compound can be freely adjusted, the compound witha shallow HOMO energy level can be used as hole transport / electron blocking materials; and materials with a deep HOMO energy level can be used as main materials of a partial hole type light-emittinglayer.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound with spirodimethyl anthracene fluorene as the core and its application in organic electroluminescence devices. Background technique [0002] Organic electroluminescence (OLED: Organic Light Emission Diodes) device technology can not only be used to make new display products, but also can be used to make new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, with a very wide range of application prospects . OLED light-emitting device is 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 purpose to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emittin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D265/38C07D279/22C07D491/048C07D491/052C07D491/153C07D471/04C07D495/04C07D221/18C07D498/04C07D265/34C07D513/04C07D471/06C07D498/06C07D417/12C07D279/14C07D495/14C07D498/14C07D513/14C07D219/08C07D405/12C07D409/12C07D401/12C07D413/12C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D219/02C07D219/08C07D221/18C07D265/34C07D265/38C07D279/14C07D279/22C07D401/12C07D405/12C07D409/12C07D413/12C07D417/12C07D471/04C07D471/06C07D491/048C07D491/052C07D491/153C07D495/04C07D495/14C07D498/04C07D498/06C07D498/14C07D513/04C07D513/14C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1029C09K2211/1011C09K2211/1088C09K2211/1092H10K85/624H10K85/636H10K85/633H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 蔡啸张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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