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Novel materials for organic electroluminescent devices

A general formula, compound technology, applied in the field of new materials for organic electroluminescent devices, can solve the problems of low power efficiency, voltage increase, high voltage, etc.

Active Publication Date: 2009-07-22
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 2. The color coordinates of many blue emitters are still unsatisfactory
[0005] 3. Insufficient thermal stability, especially for blue dopant
Another disadvantage is that AlQ 3 strong hygroscopicity, and low electron mobility, which lead to higher voltage and thus lower power efficiency
To prevent short circuits in displays, it is desirable to increase the thickness of the layer; for AlQ 3 This is not possible because of the low charge carrier mobility, which results in an increase in voltage
Moreover, AlQ 3 Intrinsic color (yellow when solid), color shift due to reabsorption and weak re-emission, especially in blue OLEDs, proves to be very unfavorable
Only OLEDs with comparable efficiencies and color positional defects can be fabricated here

Method used

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  • Novel materials for organic electroluminescent devices
  • Novel materials for organic electroluminescent devices
  • Novel materials for organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0199] Example 1: 1,2-benzo-3,8-bis(N,N-diphenylamino)-6,6,12,12-tetramethyl-6,12-dihydroindeno[1, 2-b]fluorene

[0200] a) ethyl 1-(9,9-dimethyl-9H-fluoren-2-yl)naphthalene-2-carboxylate

[0201]

[0202] 86.3g (362.55mmol) of 9,9'-dimethylfluorene-2-boronic acid, 92g (329.59mol) of 2-carboxyethylbromonaphthalene and 159.4g (692mmol) of tripotassium phosphate monohydrate were suspended in To 450 ml of toluene, 230 ml of dioxane, 700 ml of water and 6.0 g (19.8 mmol) of tri-o-tolylphosphine, 740 mg (3.3 mmol) of palladium acetate were subsequently added, and the mixture was heated at boiling point for 4 hours. The organic phase was separated off, filtered through silica gel and evaporated in vacuo. The residue was recrystallized from heptane. Yield: 100.6 g (78%) of colorless solid.

[0203] b) 2-[1-(9,9-dimethyl-9H-fluoren-2-yl)naphthalene-2-yl]propan-2-ol

[0204]

[0205] 100.6 g of ethyl 1-(9,9-dimethyl-9H-fluoren-2-yl)naphthalene-2-carboxylate (256 mmol) was fi...

Embodiment 8

[0218] Example 8: 1,2-Benzo-3-[9-{10-(2-naphthyl)}anthracenyl]-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b]fluorene

[0219] a) 1,2-benzo-3-bromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene

[0220]

[0221] Dissolve 15.5g (43mmol) of 1,2-benzo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene in 350ml of THF, add 8.4 g (47.3 mmol) of NBS, the mixture was heated at the boiling point for 4 hours. After removing the solvent in vacuo, the residue was washed by boiling in ethanol / water (1:1), the solid was filtered off with suction, washed with ethanol and dried, leaving 15.4 g (82%) of the monobromide as a colorless powder.

[0222] b) 1,2-benzo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene-3-boronic acid

[0223]

[0224] Suspend 14g (32mmol) of 1,2-benzo-3-bromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene in 150ml of In dry ether, add 21ml (42mmol) of 2M n-butyllithium cyclohexane solution at -70°C, stir the mixture at this ...

Embodiment 13

[0231] Example 13: 1,2-benzo-3-(N,N-bis-4-tert-butylphenylamino)-6,6,12,12-tetramethyl-6,12-dihydroindeno [1,2-b]fluorene

[0232]

[0233] 23.1g (53mmol) of 1,2-benzo-3-bromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene and 19.2g (68mmol) of di-tert-butylphenylamine was dissolved in 100ml of dry toluene, with N 2 The solution was saturated and then 0.5 ml (2 mmol) of tri-tert-butylphosphine were added, followed by 240 mg (1 mmol) of palladium acetate and 8.6 g (89 mmol) of sodium tert-butoxide. The mixture is heated at the boiling point for 3 hours, the organic phase is separated off, washed twice with water, filtered and evaporated in a rotary evaporator. Four times recrystallization from isopropanol afforded 24 g (71%) of the amine in the form of a yellow powder with a purity (RP-HPLC) of >99.9%. This compound has excellent thermal stability. No decomposition was observed upon sublimation.

[0234] The following compounds were synthesized similarly to the...

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Abstract

The invention relates to the compounds of formulae (1) to (6) and to organic electroluminescent devices, especially blue-emitting devices, in which these compounds are used as the host material or doping agent in the emitting layer and / or as the hole transport material and / or as the electron transport material.

Description

field of invention [0001] The present invention relates to organic semiconductors and their use in organic electronic devices. Background technique [0002] Organic semiconductors are being developed for many different applications that can be attributed in the broadest sense to the electronics industry. The structure of organic electroluminescent devices (OLEDs) in which these organic semiconductors are used as functional materials is described, for example, in US Pat. However, these devices still have considerable issues that require urgent improvement: [0003] 1. Commonly used compounds do not have a sufficiently low LUMO (lowest unoccupied molecular orbital). Compounds with lower LUMO are required for easier electron injection and thus for reduction of operating voltage. [0004] 2. The color coordinates of many blue illuminants are still unsatisfactory. [0005] 3. Thermal stability, especially the thermal stability of the blue dopant is insufficient. [0006] 4. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H05B33/14
CPCC09K2211/1011C07C25/22H01L51/5012C07F5/027H01L51/5048C09K11/06C07C13/62C09K2211/1033C07C211/61C09B57/00C09K2211/1007C09B1/00C07D493/06C07F7/0809C09K2211/1014C09K2211/1044C07D333/54H01L51/0056C09B23/0008C09B57/008C09K2211/1029C09K2211/1092H01L51/006C09K2211/1037C07D277/84C07D265/38C07D307/77C07D495/06H05B33/14C09B3/14C09B57/001C09K2211/1059C09K2211/1088C07C49/792C07C2103/90C09B23/14C07D333/22Y02E10/549H01L51/0058C07C2603/90C07F7/0805H10K85/624H10K85/626H10K85/633H10K50/14H10K50/11C07D209/82C07D333/76
Inventor 阿尔内·比辛菲利普·施特塞尔霍尔格·海尔
Owner MERCK PATENT GMBH
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