Five-membered ring substituted compound with xanthone as core and use thereof

Abstract

The invention discloses a five-membered ring substituted compound with xanthone as a core and a use thereof. According to the compound, xanthone is a mother nucleus and is connected to an aromatic heterocyclic group so that molecular symmetry is destroyed, molecule crystallinity is destroyed, intermolecular aggregation is avoided and good film-forming performances are obtained. The compound as a light-emitting layer material is used for an organic light-emitting diode. An OLED device prepared from the compound has good photoelectric properties and can satisfy the requirements of the panel manufacturing companies.

Description

Technical field

[0001] The present invention relates to the field of semiconductor technology, in particular to a xanthone-based compound and its application as a light-emitting layer material in an organic light-emitting diode. Background technique

[0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat panel display product at home and abroad. This is because OLED displays have self-luminous, wide viewing angle (up to 175°), short response time, high luminous efficiency, and wide color. Domain, low working voltage (3~10V), thin panel (can be less than 1mm) and rollable characteristics. OLED is hailed as the star flat display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and the future is limitless.

[0003] The principle of OLED light emission is by applying an external voltage. After holes and electrons overcome the interface barrier, they are injec...

Examples

Embodiment 1

[0064] Example 1 Synthesis of compound C03

[0065]

[0066] In a 250ml four-necked flask, add 0.01mol 2-(3-bromophenyl)-xanthone, 0.015mol compound A1, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 99.70% and a yield of 42.10%.

[0067] HPLC-MS: The molecular weight of the material is 694.23, and the measured molecular weight is 694.26.

Embodiment 2

[0068] Example 2 Synthesis of Compound C05

[0069]

[0070] In a 250ml four-neck flask, add 0.01mol 2-bromo-xanthone, 0.015molA2, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 98.60% and a yield of 56.20%.

[0071] HPLC-MS: The molecular weight of the material is 644.25, and the measured molecular weight is 644.32.

Embodiment 3

[0072] Example 3 Synthesis of Compound C11

[0073]

[0074] In a 250ml four-necked flask, add 0.01mol 2-(3-bromophenyl)-xanthone, 0.015molA3, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 98.20% and a yield of 42.30%.

[0075] HPLC-MS: The molecular weight of the material is 811.32, and the measured molecular weight is 811.46.

Technical field

[0001] The present invention relates to the field of semiconductor technology, in particular to a xanthone-based compound and its application as a light-emitting layer material in an organic light-emitting diode. Background technique

[0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) has become a very popular emerging flat panel display product at home and abroad. This is because OLED displays have self-luminous, wide viewing angle (up to 175°), short response time, high luminous efficiency, and wide color. Domain, low working voltage (3~10V), thin panel (can be less than 1mm) and rollable characteristics. OLED is hailed as the star flat display product of the 21st century. As the technology becomes more and more mature, it may develop rapidly in the future, and the future is limitless.

[0003] The principle of OLED light emission is by applying an external voltage. After holes and electrons overcome the interface barrier, they are injec...

Examples

Embodiment 1

[0064] Example 1 Synthesis of compound C03

[0065]

[0066] In a 250ml four-necked flask, add 0.01mol 2-(3-bromophenyl)-xanthone, 0.015mol compound A1, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 99.70% and a yield of 42.10%.

[0067] HPLC-MS: The molecular weight of the material is 694.23, and the measured molecular weight is 694.26.

Embodiment 2

[0068] Example 2 Synthesis of Compound C05

[0069]

[0070] In a 250ml four-neck flask, add 0.01mol 2-bromo-xanthone, 0.015molA2, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 98.60% and a yield of 56.20%.

[0071] HPLC-MS: The molecular weight of the material is 644.25, and the measured molecular weight is 644.32.

Embodiment 3

[0072] Example 3 Synthesis of Compound C11

[0073]

[0074] In a 250ml four-necked flask, add 0.01mol 2-(3-bromophenyl)-xanthone, 0.015molA3, 0.03mol sodium tert-butoxide, 1×10 under a nitrogen atmosphere -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butyl phosphine, 150 ml of toluene, heating and refluxing for 24 hours, sampling point plate, reaction complete, natural cooling, filtration, rotary evaporation of the filtrate, and silica gel column to obtain the target product with a purity of 98.20% and a yield of 42.30%.

[0075] HPLC-MS: The molecular weight of the material is 811.32, and the measured molecular weight is 811.46.

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