Acridine cyclo-thiaxanthene sulfone derivative as well as preparation method and application thereof

Abstract

The invention belongs to the field of organic optoelectronic materials and particularly relates to an acridine cyclo-thiaxanthene sulfone derivative as well as a preparation method and application thereof. The structural general formula of the acridine cyclo-thiaxanthene sulfone derivative is shown in the specification, wherein Ar represents phenyl, biphenylyl, naphthyl or anthryl. According to the compound, the acridine cyclo-thiaxanthene sulfone is taken as a nuclear parent and is linked with aromatic heterocyclic groups, so that the molecular symmetry is broken, the aggregation among molecules is avoided, and a good film-forming property is achieved; the acridine cyclo-thiaxanthene sulfone compound is taken as a luminescent layer material to be applied to organic light emitting diodes and has relatively high glass transition temperature and molecular thermal stability, so that the optoelectronic performance of OLED devices can be effectively improved, and the service lives of the OLED devices can be effectively prolonged; and the OLED devices utilizing the compound disclosed by the invention have good optoelectronic performance and can meet the industrialization requirements of panel manufacturing enterprises.

Description

technical field

[0001] The invention belongs to the field of organic photoelectric materials, in particular to an acridine spirothioxanthene derivative, a preparation method and application thereof. Background technique

[0002] Organic Light Emitting Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat-panel display product at home and abroad. Domain, low operating voltage (3 ~ 10V), thin panel (less than 1mm) and rollable characteristics. OLED is hailed as the star flat panel display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and its future is limitless.

[0003] 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 dev...

Examples

Embodiment 1

[0044] Example 1 Compound C01

[0045]

[0046] Take a 250ml three-necked flask, and add 0.01mol 10-(4-bromophenyl)-acridine spirothioxanthene sulfone, 0.02mol compound R1, 0.03mol sodium tert-butoxide, 1×10 under nitrogen atmosphere. -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.56% and a yield of 57%.

[0047] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 52 h 36 N 2 o 3 S, theoretical value: 768.92, test value: 769.21.

Embodiment 2

[0048] Example 2 Compound C02

[0049]

[0050] Take a 250ml three-necked flask, and add 0.01mol 10-(3-bromophenyl)-acridine spirothioxanthene sulfone, 0.02mol compound R1, 0.03mol sodium tert-butoxide, 1×10 under nitrogen atmosphere. -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.326% and a yield of 48%.

[0051] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 52 h 36 N 2 o 3 S, theoretical value: 768.92, test value: 769.18.

Embodiment 3

[0052] Example 3 Compound C09

[0053]

[0054] Take a 250ml three-neck flask, and add 0.01mol 10-(4-bromobiphenyl)-acridine spirothioxanthene sulfone, 0.02mol compound R1, 0.03mol sodium tert-butoxide, 1×10 under nitrogen atmosphere. -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.6% and a yield of 45%.

[0055] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 58 h 40 N 2 o 3 S, theoretical value: 845.01, test value: 845.22.

technical field

[0001] The invention belongs to the field of organic photoelectric materials, in particular to an acridine spirothioxanthene derivative, a preparation method and application thereof. Background technique

[0002] Organic Light Emitting Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat-panel display product at home and abroad. Domain, low operating voltage (3 ~ 10V), thin panel (less than 1mm) and rollable characteristics. OLED is hailed as the star flat panel display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and its future is limitless.

[0003] 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 dev...

Examples

Embodiment 1

[0044] Example 1 Compound C01

[0045]

[0046] Take a 250ml three-necked flask, and add 0.01mol 10-(4-bromophenyl)-acridine spirothioxanthene sulfone, 0.02mol compound R1, 0.03mol sodium tert-butoxide, 1×10 under nitrogen atmosphere. -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.56% and a yield of 57%.

[0047] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 52 h 36 N 2 o 3 S, theoretical value: 768.92, test value: 769.21.

Embodiment 2

[0048] Example 2 Compound C02

[0049]

[0050] Take a 250ml three-necked flask, and add 0.01mol 10-(3-bromophenyl)-acridine spirothioxanthene sulfone, 0.02mol compound R1, 0.03mol sodium tert-butoxide, 1×10 under nitrogen atmosphere. -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.326% and a yield of 48%.

[0051] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 52 h 36 N 2 o 3 S, theoretical value: 768.92, test value: 769.18.

Embodiment 3

[0052] Example 3 Compound C09

[0053]

[0054] Take a 250ml three-neck flask, and add 0.01mol 10-(4-bromobiphenyl)-acridine spirothioxanthene sulfone, 0.02mol compound R1, 0.03mol sodium tert-butoxide, 1×10 under nitrogen atmosphere. -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and spot plated, naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.6% and a yield of 45%.

[0055] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 58 h 40 N 2 o 3 S, theoretical value: 845.01, test value: 845.22.

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