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Organic electroluminescent device with bipolar body material with spiro[fluorine-9,2'-imidazole] group

An electroluminescence device and luminescence technology, which is applied in the manufacture of electric solid-state devices, semiconductor devices, semiconductor/solid-state devices, etc., can solve the problems of easy crystallization at glass transition temperature, unbalanced carrier injection and transmission, high driving voltage, etc. Problems, to achieve the effects of carrier injection and transport balance, long service life, and high luminous efficiency

Active Publication Date: 2018-07-10
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems of high driving voltage required by existing host (CBP) materials, easy crystallization at glass transition temperature, and unbalanced carrier injection and transport, the present invention provides an organic electroluminescence device, the host material of which is a light-emitting layer is Bipolar host material, the material uses spiro[fluorene-9,2'-imidazole] as the strong electron center core, and diphenylamine, carbazole, acridine and other derivatives with strong electron donating ability as the linking group, Form D-A type, D-A-D type bipolar material

Method used

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  • Organic electroluminescent device with bipolar body material with spiro[fluorine-9,2'-imidazole] group
  • Organic electroluminescent device with bipolar body material with spiro[fluorine-9,2'-imidazole] group
  • Organic electroluminescent device with bipolar body material with spiro[fluorine-9,2'-imidazole] group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Synthesis of 4'-(4-bromophenyl)-5'-phenylspiro(fluorene-9,2'-imidazole) (c1)

[0028] The synthetic route is as follows:

[0029]

[0030] Concrete synthetic steps are:

[0031] Weigh 1-(4-bromophenyl)-2-phenylethyl-1,2-dione (14.5 g, 50 mmol) (a1) (prepared by Sonogashira coupling reaction, re-oxidation), 9-fluorenone (7.2g, 40mmol) (b1), ammonium acetate (19.2g, 250mmol), 150mL glacial acetic acid in a 250mL round bottom flask, heated to reflux and stirred for 16 hours. After the reaction, it was naturally cooled to room temperature, poured into 200 mL of pure water, and a yellow solid was precipitated. Filter with sand core funnel and wash with water. Silica gel column chromatography separated to obtain 9.9 g of yellow solid. Yield: 55%. (2) 9,9-Dimethyl-10-[4-[4'-phenylspiro(fluorene-9,2'-imidazolium)-5'-yl]phenyl]-9,10-dihydroacridine Synthesis of pyridine (1)

[0032] The synthetic route is as follows:

[0033]

[0034] Concrete synthetic steps a...

Embodiment 2

[0038] (1) Synthesis of 2-bromo-4'-(4-bromophenyl)-5'-phenylspiro(fluorene-9,2'-imidazole) (c2)

[0039] The synthetic route is as follows:

[0040]

[0041]Weigh 1-(4-bromophenyl)-2-phenylethyl-1,2-dione (4.34 g, 15 mmol) (a1) (prepared by Sonogashira coupling reaction, re-oxidation), 2-bromo- 9-Fluorenone (3.89g, 15mmol), ammonium acetate (5.8g, 75mmol), and 30mL of glacial acetic acid were placed in a 50mL round bottom flask, heated to reflux and stirred for 16 hours. After the reaction, it was naturally cooled to room temperature, poured into 100 mL of pure water, and a yellow solid was precipitated. Filter with sand core funnel and wash with water. Silica gel column chromatography separated to obtain 4.1 g of yellow solid. Yield: 52%.

[0042] (2) 10-(4-(2-(9,9-dimethylacridin-10(9H)-yl)-4'-phenylspiro(fluorene-9,2'-imidazole)-5'- Synthesis of yl]phenyl]-9,9-dimethyl-9,10-dihydroacridine (2)

[0043] The synthetic route is as follows:

[0044]

[0045] Concre...

Embodiment 3

[0049] Glass transition temperature test

[0050] Under the protection of nitrogen, the glass transition temperature of compound 2 was measured by differential scanning calorimetry (DSC) at a heating and cooling rate of 20 °C / min. The glass transition temperature T of compound 2 was measured g at 158°C ( figure 1 ). However, the glass transition temperature of CBP reported in the literature is only 62°C.

[0051] It can be seen that the compound in the present invention has a higher glass transition temperature than the commonly used host material CBP, and the present invention significantly improves the thermal stability of the host material.

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Abstract

The invention relates to an organic electroluminescent device which comprises a cathode, an anode and an organic layer. The organic layer is one or more layers selected from a hole blocking layer, anelectron transport layer and a light emitting layer. The organic layer comprises a compound with a structure represented by a formula (I), wherein R1-R3 are acridinyl with substituted or un-substituted C1-C4 alkyl or alkyloxy, phenothiazinyl, carbazole, diphenylamine, hydrogen, halogen and C1-C4 alkyl. Experiments prove a fact that the device has a relatively high glass-transition temperature (Tg=158 DEG C); and the bipolar material facilitates carrier injection and transport balance, and therefore the organic electroluminescent device has advantages of high light emitting efficiency and longservice life.

Description

technical field [0001] The invention relates to an organic electroluminescent device, in particular to an organic electroluminescent device prepared from a bipolar host material with spiro[fluorene-9,2'-imidazole] as the central core. Background technique [0002] Organic light-emitting diodes (OLEDs) have the characteristics of fast response speed, low energy consumption, high brightness, wide viewing angle, bendability, and active light emission, and have been highly valued by the scientific and industrial circles. Its application in display, lighting and other aspects has great potential. Electrofluorescence and electrophosphorescence are referred to as first- and second-generation OLEDs, respectively. OLEDs based on fluorescent materials have the characteristics of high stability, but are limited by the law of quantum statistics. The maximum internal quantum efficiency of luminescence is only 25%. Phosphorescent materials have the spin-orbit coupling effect of heavy a...

Claims

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Application Information

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IPC IPC(8): H01L51/50H01L51/54
CPCH10K85/111H10K50/10C09K11/06
Inventor 彭嘉欢戴雷蔡丽菲
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS