Derivant of electrophosphorescence 1, 8-naphthimide and luminous ligand thereof

A kind of naphthalimide, electrophosphorescence technology, applied in 1 field

Inactive Publication Date: 2005-01-05
EAST CHINA UNIV OF SCI & TECH
View PDF1 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the Chinese patent application number 00116212.8 discloses a class of molecularly twisted electroluminescent materials co

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Derivant of electrophosphorescence 1, 8-naphthimide and luminous ligand thereof
  • Derivant of electrophosphorescence 1, 8-naphthimide and luminous ligand thereof
  • Derivant of electrophosphorescence 1, 8-naphthimide and luminous ligand thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 4-piperidinyl-N-[4-(2-benzothiazolyl)phenyl]-1,8-naphthalimide:

[0026]

[0027] (1) Preparation of 4-piperidinyl-1,8-naphthalene anhydride

[0028] In a round bottom flask, add 2.76g of 4-bromo-1,8-naphthalene anhydride, 1.5mL of piperidine and 40mL of ethylene glycol monomethyl ether, stir, and heat to reflux for 3h. After standing overnight, a precipitate precipitated out. Suction filtration yielded an orange solid. Recrystallized from ethanol and ethylene glycol monomethyl ether to obtain 2.04 g of orange-red needle-like crystals with a yield of 73.6%. The melting point is 172-173°C.

[0029] (2) Preparation of 4-(2-benzothiazolyl)aniline

[0030] In a round bottom flask, 2.74 g p-aminobenzoic acid, 2.2 mL o-aminothiophenol and 30 mL polyphosphoric acid (PPA) were added. Protected by argon, heated to 250°C for 4h. After cooling, dilute with water until solid precipitates. Filter, pour the filter cake into 10% Na 2 CO 3 In the aqueous soluti...

Embodiment 2

[0037] Synthesis of 4-piperidinyl-N-[4-(2-oxazolyl)phenyl]-1,8-naphthalimide:

[0038]

[0039] (1) Preparation of 4-(2-benzoxazolyl)aniline

[0040] Except that one of the raw materials o-aminothiophenol is replaced by o-aminophenol, the preparation method is the same as (2) in Example 1. 3.99 g of pure product was obtained with a yield of 63%. The melting point is 172-175°C.

[0041] (2) Preparation of 4-piperidinyl-N-[4-(2-oxazolyl)phenyl]-1,8-naphthalimide

[0042] 4-(2-benzoxazolyl)aniline and 4-piperidinyl-1,8-naphthalene anhydride (see step (1) of Example 1 for preparation) were prepared according to the method of (3) in Example 1 Product (yellow-green solid). Yield 45.8%. Melting point > 270°C.

[0043] 1 H-NMR (CDCl 3 ): 1.76(m, 2H), 1.92(m, 4H), 3.28(m, 4H), 7.22(d, J=8.08Hz, 1H), 7.39(t, 2H), 7.50(d, J=8.43Hz , 2H), 7.62(d×d, J=3.36Hz, J=2.29Hz, 1H), 7.73(t, 1H), 7.82(d×d, J=2.33Hz, J=3.3Hz, 1H), 8.44 (d, J=8.43Hz, 2H), 8.46(t, 1H), 8.56(d, J=8.06Hz, 1H...

Embodiment 3

[0046] Synthesis of 4-piperidinyl-N-[4-(2-benzimidazolyl)phenyl]-1,8-naphthalimide:

[0047]

[0048] (1) Preparation of 4-(2-benzimidazolyl)aniline

[0049] Except that one of the raw materials o-aminothiophenol is replaced by o-phenylenediamine, the preparation method is the same as (2) in Example 1. 1.80 g of pure 4-(2-benzimidazolyl)aniline was obtained with a yield of 28.7%. The melting point is 174-175°C.

[0050] (2) Preparation of 4-piperidinyl-N-[4-(2-benzimidazolyl)phenyl]-1,8-naphthalimide

[0051] 4-(2-benzimidazolyl)aniline and 4-piperidinyl-1,8-naphthalene anhydride (see step (1) of Example 1 for preparation) were prepared according to the method of (3) in Example 1 to obtain the target product (yellow-green solid). Yield 55.1%. Melting point > 270°C.

[0052] 1 H-NMR (CDCl 3 ): 1.76(m, 2H), 1.92(d, J=4.59Hz, 4H), 3.30(m, 4H), 7.25(t, 1H), 7.27(d, 2H), 7.44(d, J=8.21Hz , 2H), 7.47(t, 1H), 7.74(t, 1H), 7.84(d, J=6.31Hz, 1H), 8.13(d, J=8.2Hz, 2H), 8.48(...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Resistanceaaaaaaaaaa
Login to view more

Abstract

The invention designs and synthesizes an electrophosphorescent or electrofluorescent 1,8-naphthalimide derivative. The derivative contains a five-membered heterocyclic functional grou: 1, 8-naphthalimide, benzothiazole, etc, which ensures both the injection and compound of carriers and the generation of excitons happen in molecules and simultaneously avoids the defect of light chroma change caused by the change of conjugated delocalization degree; its maximum lighting wavelength is in 511-521 nm (emitting yellow-green light) or greater than 630 nm (emitting red light), and at driving voltage, the maximum light brightness is 4500-4800 cd/sq m.

Description

technical field [0001] The present invention relates to an electroluminescent organic compound, in particular to an electrophosphorescent or fluorescent 1,8-naphthalimide derivative. Background technique [0002] Compared with liquid crystal displays, organic electroluminescent devices (OLEDs) are recognized as the most advanced display technology. It completely overcomes the shortcomings of liquid crystal display, and has the advantages of low-voltage DC drive, active light emission, large viewing angle, easy bending, fast response speed, large-area display, complete luminous color and low cost, so almost all related products in the world Many large companies have invested a lot of manpower and material resources to join this increasingly fierce competition. [0003] Naphthalimide derivatives are a very important class of functional materials. At present, in addition to being widely used as fluorescent dyes and fluorescent whitening agents, it can also be used in high-tec...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D401/10C09K11/06
Inventor 田禾丁国华荆淑萍朱为宏
Owner EAST CHINA UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap