Compound containing ketone and heterocyclic nitrogen and application thereof to organic light-emitting device

Abstract

The invention discloses a compound containing ketone and heterocyclic nitrogen and application thereof to an organic light-emitting device. The compound has the advantages of being not subjected to crystallization and aggregation easily and having good film-forming property, and rigid groups in molecules can improve heat stability of a material. The compound serving as a light-emitting layer material is applied to an organic light-emitting diode (OLED), and a manufactured OLED device has good photoelectric property and can meet the requirements of panel manufacturing enterprises.

Description

technical field

[0001] The invention relates to the technical field of semiconductors, in particular to a compound containing a ketone and a nitrogen heterocycle, and its application as a light-emitting layer material in an organic light-emitting diode. 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.

[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 device. As a current device, when a voltage is applied to the electrodes at b...

Examples

Embodiment 1

[0039] Example 1 Compound 1

[0040]

[0041] The concrete synthetic route of this compound is provided now:

[0042]

[0043] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 4-bromobenzophenone, 0.015mol 9H-5-oxa-9,13b-diaza-naphthalene[3,2,1- de]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 98.2% and a yield of 70.00%.

[0044] HPLC-MS: The molecular weight of the material is 452.15, and the measured molecular weight is 452.22.

Embodiment 2

[0045] Example 2 Compound 2

[0046]

[0047] The concrete synthetic route of this compound is provided now:

[0048]

[0049] In a 250ml four-necked flask, add 0.01mol biphenyl-4-yl-(3-bromophenyl)methanone, 0.015mol 9H-5-oxa-9,13b-diazepine under nitrogen atmosphere -Naphth[3,2,1-de]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.0% and a yield of 72.00%.

[0050] HPLC-MS: The molecular weight of the material is 528.18, and the measured molecular weight is 528.62.

Embodiment 3

[0051] Example 3 Compound 7

[0052]

[0053] The concrete synthetic route of this compound is provided now:

[0054]

[0055] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol (4-bromophenyl)-triphenylen-2-yl-methanone, 0.015mol 9,9-dimethyl-5H,9H- 5,13b-diaza-naphthalene[3,2,1-de]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.1% and a yield of 76.00%.

[0056] HPLC-MS: The molecular weight of the material is 628.25, and the measured molecular weight is 628.67.

technical field

[0001] The invention relates to the technical field of semiconductors, in particular to a compound containing a ketone and a nitrogen heterocycle, and its application as a light-emitting layer material in an organic light-emitting diode. 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.

[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 device. As a current device, when a voltage is applied to the electrodes at b...

Examples

Embodiment 1

[0039] Example 1 Compound 1

[0040]

[0041] The concrete synthetic route of this compound is provided now:

[0042]

[0043] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 4-bromobenzophenone, 0.015mol 9H-5-oxa-9,13b-diaza-naphthalene[3,2,1- de]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 98.2% and a yield of 70.00%.

[0044] HPLC-MS: The molecular weight of the material is 452.15, and the measured molecular weight is 452.22.

Embodiment 2

[0045] Example 2 Compound 2

[0046]

[0047] The concrete synthetic route of this compound is provided now:

[0048]

[0049] In a 250ml four-necked flask, add 0.01mol biphenyl-4-yl-(3-bromophenyl)methanone, 0.015mol 9H-5-oxa-9,13b-diazepine under nitrogen atmosphere -Naphth[3,2,1-de]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.0% and a yield of 72.00%.

[0050] HPLC-MS: The molecular weight of the material is 528.18, and the measured molecular weight is 528.62.

Embodiment 3

[0051] Example 3 Compound 7

[0052]

[0053] The concrete synthetic route of this compound is provided now:

[0054]

[0055] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol (4-bromophenyl)-triphenylen-2-yl-methanone, 0.015mol 9,9-dimethyl-5H,9H- 5,13b-diaza-naphthalene[3,2,1-de]anthracene, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.1% and a yield of 76.00%.

[0056] HPLC-MS: The molecular weight of the material is 628.25, and the measured molecular weight is 628.67.

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