Organic electroluminescent compound containing adamantane and heterocyclic structure and its preparation method and application

An electroluminescent device, adamantane technology, applied in organic chemistry, chemical instruments and methods, preparation of amino compounds from amines, etc., can solve the problem of low color purity and efficiency of light-emitting devices, destruction of hole-electron charge balance, quantum Improve thermal stability, improve physical and chemical properties, and improve device performance

Active Publication Date: 2022-05-20
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, OLEDs using these materials have problems in deteriorating quantum efficiency and lifetime
This is because the hole transport material usually has a low highest occupied molecular orbital (HOMO) value, and the excitons generated in the light-emitting layer diffuse to the interface of the hole transport layer or the side of the hole transport layer, eventually resulting in The luminescence of the luminescence or the charge imbalance in the luminescent layer, thereby emitting light on the interface of the hole transport layer, making the color purity and efficiency of the organic electroluminescent device lower, and the life is shortened; in addition, when driving the OLED at a high current , thermal stress occurs between the anode and the hole injection layer, and the thermal stress significantly reduces the service life of the device
In addition, since the organic materials used in the hole transport region have very high hole mobility, the hole-electron charge balance may be disrupted and the quantum efficiency may decrease

Method used

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  • Organic electroluminescent compound containing adamantane and heterocyclic structure and its preparation method and application
  • Organic electroluminescent compound containing adamantane and heterocyclic structure and its preparation method and application
  • Organic electroluminescent compound containing adamantane and heterocyclic structure and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The synthesis of embodiment 1 compound 1

[0050] synthetic route:

[0051]

[0052] Specific synthesis method:

[0053] Step 1: Add reactant B-1 (50mmol) into a 500mL three-necked flask, add 100mL of anhydrous tetrahydrofuran, replace with nitrogen three times, then cool the reaction system to -78°C, add dropwise 20mL of n-BuLi (2.5M) ( 50mmol), stirred at -78°C for 2h. Intermediate A-1 (42 mmol) was dissolved in 50 mL of tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 10 h. 100 mL of distilled water was added to terminate the reaction, the organic phase was collected by liquid separation, and dried by adding anhydrous magnesium sulfate. The solvent was removed by rotary evaporator to obtain intermediate C-1 (10.1 g, yield 76%, MS: 316.18).

[0054] Step 2: Add intermediate C-1 (30mmol) and intermediate D-1 (36mmol) into a 500mL three-neck flask, ...

Embodiment 2

[0076] The synthesis of embodiment 2 compound 41

[0077] synthetic route:

[0078]

[0079] Specific synthesis method:

[0080]Step 1: Add reactant B-41 (120mmol) into a 500mL three-necked flask, add 200mL of anhydrous tetrahydrofuran, replace with nitrogen three times, then cool the reaction system to -78°C, add dropwise 40mL of n-BuLi (2.5M) ( 120mmol), stirred at -78°C for 2h. Reactant A-41 (100 mmol) was dissolved in 50 mL of tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 10 h. 100 mL of distilled water was added to terminate the reaction, the organic phase was collected by liquid separation, and dried by adding anhydrous magnesium sulfate. The solvent was removed by rotary evaporator to obtain intermediate C-41 (32.2 g, 73% yield, 441.19).

[0081] Step 2: Add intermediate C-41 (70mmol) into a 1L three-necked flask, add 400mL of glacial acetic acid...

Embodiment 3

[0090] The synthesis of embodiment 3 compound 60

[0091] synthetic route:

[0092]

[0093] Specific synthesis method:

[0094] Step 1: Add the reactant B-60 (120mmol) into a 500mL three-necked flask, add 200mL of anhydrous tetrahydrofuran, replace with nitrogen three times, then cool the reaction system to -78°C, add dropwise 40mL of n-BuLi (2.5M) ( 120mmol), stirred at -78°C for 2h. The reactant A-60 (100 mmol) was dissolved in 50 mL of tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 10 h. 100 mL of distilled water was added to terminate the reaction, the organic phase was collected by liquid separation, and dried by adding anhydrous magnesium sulfate. The solvent was removed by rotary evaporator to obtain intermediate C-60 (36.4 g, yield 75%, MS: 485.21).

[0095] Step 2: Add intermediate C-60 (70mmol) into a 1L three-neck flask, add 400mL of glacial ...

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Abstract

The present invention relates to an organic electroluminescent compound containing adamantane and a heterocyclic structure and its preparation method and application. Its chemical structural formula is shown in general formula I: wherein, X exists or does not exist; Independently selected from chemical bonds, O, S, Si(R4R5), C(R6R7), NR8; Y1‑Y9 independently selected from carbon, nitrogen, oxygen, sulfur atoms, at least one of which is a heteroatom; R1‑R3 each independently selected from methyl, ethyl, propyl, tert-butyl, alkoxy, alkylmercapto, aryloxy, phenyl, biphenyl, or naphthyl; Ar1 ​​and Ar2 are each independently selected from naphthyl, Phenanthryl, phenyl, methylphenyl, terphenyl, biphenyl, dibenzofuran, dibenzothiophene, cyclopentadithiophene, cyclopentadifuran, fluorene and their derivatives. The compound changes the spatial structure and physical and chemical properties of the compound through the use of the adamantane structure and the introduction of heteroatoms. As a luminescence auxiliary layer, the driving voltage of the device can be greatly reduced, and the life and efficiency of the device can be significantly improved.

Description

technical field [0001] The invention relates to the technical field of luminescent materials, in particular to an organic electroluminescent compound containing adamantane and a heterocyclic structure, a preparation method and application thereof, and an organic electroluminescent device using the compound as a luminescent auxiliary layer. Background technique [0002] OLED materials are divided into luminescent materials, hole transport materials, electron transport materials and the like. Among them, the hole transport material directly affects the efficiency and lifetime of the OLED. Compounds commonly used in the existing hole transport region include copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N' -Diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"- Tris(3-methylphenylphenylamino)triphenylamine (MTDATA), etc. However, OLEDs using these materials have problems in deteriorating quantum efficiency and li...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42C07D213/74C07D221/22C07D401/04C07D241/20C07C211/61C07D409/12C07D405/12C07D403/04C07D239/70C07D471/10C07D491/107C07D311/78C07D335/04C07D495/10C07C211/54C07C209/68C07D405/04C09K11/06H01L51/50H01L51/54
CPCC07D239/42C07D213/74C07D221/22C07D401/04C07D241/20C07C211/61C07D409/12C07D405/12C07D403/04C07D239/70C07D471/10C07D491/107C07D311/78C07D335/04C07D495/10C07C211/54C07C209/68C07D405/04C09K11/06C07C2603/90H10K85/624H10K85/636H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/15H10K50/11Y02E10/549
Inventor 马晓宇贾宇张雪金成寿陈振生徐佳楠韩文坤
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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