Organic electroluminescent material and device

An organic compound, selected technology, applied in the direction of luminescent materials, electric solid devices, electrical components, etc., can solve the problems of uneven distribution of excitons, unsatisfactory device life, unstable phosphine groups, etc.

Inactive Publication Date: 2019-11-15
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] However, the above two types of hosts have the following defects in application: the hole-type carbazole-based host material has an uneven distribution of excitons due to its weak electron transport ability, and the device efficiency rolls off seriously; the phosphorus-oxygen compound host material although High efficiency, but unsatisfactory device lifetime due to instability of phosphine groups

Method used

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  • Organic electroluminescent material and device
  • Organic electroluminescent material and device
  • Organic electroluminescent material and device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0079] Synthesis Example 1: Synthesis of Product P1

[0080]

[0081] Synthesis of Intermediate M1

[0082] Under nitrogen atmosphere, 2.2g (10.0mmol, 1eq) of 4-bromo-2,6-difluorobenzonitrile, 1.8g (12.0mmol, 1.2eq) of 4-cyanophenylboronic acid, Pd (PPh 3 ) 4 Add 0.16g (0.1mmol, 1%eq) and 4.1g (30.0mmol, 3eq) of potassium carbonate to a 100mL single-necked flask, add 20mL toluene, 5mL ethanol and 5mL water, heat up to reflux temperature, and react overnight. Using silica gel column chromatography. Obtained M1, mass spectrum: 240.

[0083] Synthesis of intermediate M2

[0084] Under a nitrogen atmosphere, 3.3g (10.0mmol, 1.0eq) of 3,9-bicarbazole, 0.24g (10.0mmol, 1.0eq) of NaHH, and DMF (30mL) were added to a 100mL single-necked bottle, and stirred for 30min in an ice-water bath Afterwards, 2.4 g (10.0 mmol, 1 eq) of the intermediate M1 was added, the temperature was raised to room temperature, and the reaction was carried out overnight. Using silica gel column chroma...

Synthetic example 2

[0087] Synthesis Example 2: Synthesis of Product P12

[0088]

[0089] Synthesis of Intermediate M3

[0090] The reactant 4-bromo-2,6-difluorobenzonitrile was replaced by 2-bromo-4-iodo-5,6-difluorobenzonitrile, and M3 was obtained through the same synthesis method as the intermediate M1 in Synthesis Example 1. , mass spectrum: 319.

[0091] Synthesis of Intermediate M4

[0092] Under nitrogen atmosphere, the intermediate M3 3.2g (10.0mmol, leq), 3,9-bicarbazole 3.7g (11.0mmol, 1.1eq), Pd 2 (dba) 3 0.09g (0.1mmol, 1%eq), and 2.9g (30.0mmol, 3eq) of potassium tert-butoxide were added to a 100mL single-necked flask, then 20mL of xylene was added, the temperature was raised to reflux temperature, and the reaction was carried out overnight. Using silica gel column chromatography. Obtained M4, mass spectrum: 240.

[0093] Synthesis of Product P12

[0094] The reactant 3,9-bicarbazole was replaced by carbazole to react with intermediate M4, and the synthesis method was the...

Synthetic example 3

[0095] Synthesis Example 3: Synthesis of Product P23

[0096]

[0097] Synthesis of Intermediate M5

[0098] The reactant 4-cyanophenylboronic acid was replaced by 4-trifluoromethylphenylboronic acid, and M5 was obtained through the same synthesis method as the intermediate M1 in Synthesis Example 1, mass spectrum: 283.

[0099] Synthesis of Intermediate M6

[0100] The reactant intermediate M1 was replaced by intermediate M5, and M6 was obtained through the same synthesis method as intermediate M2 in Synthesis Example 1, mass spectrum: 595.

[0101] Synthesis of product P23

[0102] The reactant 3,9-bicarbazole was replaced by carbazole to react with intermediate M6, and through the same synthesis method as intermediate M2 in Synthesis Example 1, P23 was obtained, mass spectrum: 742. 1 H NMR (300MHz, CDCl 3 ): 8.60(3H), 8.30(2H), 8.15(2H), 7.98(1H), 7.94(3H), 7.71(2H), 7.66(3H), 7.53(4H), 7.41(2H), 7.36(3H ), 7.33(1H), 7.31(2H), 7.28(3H).

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Abstract

The invention provides an organic electroluminescent material and an application thereof in a device. An organic compound is represented by a general formula (1) shown in the description as follows, wherein Ar1 is a group, obtained through removing n+1 H from a C6-C30 aromatic ring or C3-C30 hetero aromatic ring; Ar2 represents one or two substituents represented by a formula (2) shown in the description, wherein X is selected from a single bond, O, S, NR9 and CR10R11; R1 represents n substituents of Ar1, separately independently selected from cyano, nitro, alpha-bit-fluoro-substituted C1-C10alkyl, -C(O)R12 and -C(O)NR13, and n is an integer not smaller than 1; R2 is selected from H, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10alkoxy and cyano; R3 to R8 each independently represents one or anymultiple substituents and is independently selected from H, halogen, -C(O)R12, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, C3-C30 heteroaryl or combinations thereof; random adjacenttwo substituents can form a ring; R9 to R13 each is independently selected from C1-C10 alkyl, C6-C30 aryl and C3-C30 heteroaryl; and a molecule only has one C-N dicarbazyl.

Description

technical field [0001] The invention relates to a novel organic electroluminescent material and its application in organic electroluminescent devices, belonging to the technical field of organic electroluminescent display. Background technique [0002] Under the condition of electro-excitation, organic electroluminescent materials will produce 25% singlet state and 75% triplet state, and traditional fluorescent materials can only use singlet state excitons due to spin prohibition. In order to utilize triplet excitons, researchers have proposed many methods, the most notable of which is the utilization of phosphorescent materials. However, the T1 lifetime of phosphorescent materials is generally above 1 μs, which is much higher than the lifetime of fluorescent materials of tens of nanoseconds, so the efficiency rolls off seriously at high current densities, and due to the use of rare heavy metals, the materials are relatively expensive, which is not conducive to Product cost...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D413/14C07D417/14C07D209/88C07D403/14C07D401/14C09K11/06H01L51/54
CPCC07D209/86C07D413/14C07D417/14C07D209/88C07D403/14C07D401/14C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059H10K85/657H10K85/6572
Inventor 高文正张春雨邵爽
Owner BEIJING ETERNAL MATERIAL TECH
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