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Rare-earth europium complex and application thereof as luminescence material

A technology of europium complexes and neutral ligands, which is applied in the field of rare earth complex light-emitting materials, can solve the problems of temperature rise stability, poor carrier transport performance, and down-conversion LED that affect the efficiency of β-diketone europium complexes. Material electroluminescence OLED application is not smooth and other problems

Active Publication Date: 2015-05-20
PEKING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] At present, the rare earth europium complexes that are being studied and utilized basically use β-diketone compounds as antenna ligands, and there is no shortage of compounds with high photoluminescence quantum yields, but in down-converting LED materials or electroluminescence The application in light-emitting OLED is not smooth
The main reason is that this kind of ligands has these important defects: 1. The luminescence of β-diketone complexes is prone to thermal quenching
2. The carrier transport performance of the β-diketone structure complex is relatively poor during electroluminescence
These disadvantages severely affect the efficiency of electroluminescence of β-diketone europium complexes and their stability to elevated temperatures during device operation

Method used

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  • Rare-earth europium complex and application thereof as luminescence material
  • Rare-earth europium complex and application thereof as luminescence material
  • Rare-earth europium complex and application thereof as luminescence material

Examples

Experimental program
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Effect test

Embodiment 1

[0071] The synthetic route involved in the present embodiment is as follows:

[0072]

[0073] (1) Synthesis of 8mCND (3-cyano-4-hydroxyl-8-methyl-1,5-naphthyridine, 4-hydroxy-8-methyl-1,5-naphthyridine-3-carbonitrile):

[0074] Mix 3.24g (30mmol) of 4-methyl-3-aminopyridine and 5.07g (30mmol) of ethyl 2-cyano-3-ethoxyacrylate in a 100mL round bottom flask, add 30mL of toluene, and reflux for 15 minute. Most of the toluene was evaporated to dryness, and petroleum ether was added to precipitate the product immediately. Suction filtration, dichloromethane / petroleum ether (volume ratio 1:3) recrystallization, obtained intermediate pre-8mCND light yellow crystal 6.51g, yield 95%. 1HNMR (400MHz, CDCl 3 , δ): 10.84 (br, d, J = 12.8Hz, 1H), 8.48 (s, 1H), 8.36 (d, J = 5.2Hz, 1H), 7.91 (d, J = 12.8Hz, 1H), 7.19 (d, J=5.2Hz, 1H), 4.32(q, J=7.2Hz, 2H), 2.39(s, 3H), 1.38(t, J=7.2Hz, 3H).MS(m / z, ESI) : calcd for C 12 h 13 N 3 o 2 231, found 232 (+H + ).

[0075] After the int...

Embodiment 2

[0079] The synthetic route involved in the present embodiment is as follows:

[0080]

[0081] (1) Synthesis of 3m8mND (3-methyl-4-hydroxy-8-methyl-1,5-naphthyridin, 3,8-dimethyl-1,5-naphthyridin-4-ol):

[0082] The synthesis of 3m8mND is similar to that of 8mCND, except that the raw material 2-cyano-3-ethoxyethyl acrylate is replaced by 2-methyl-3-methoxymethyl acrylate. Mix 5.16g (46mmol) of 4-methyl-3-aminopyridine and 6.5g (50mmol) of methyl 2-methyl-3-methoxyacrylate in a 100mL round bottom flask, add 20mL of toluene, and reflux for 36 Hour. The toluene was evaporated to dryness, and the precipitated unreacted raw material 4-methyl-3-aminopyridine was recovered by suction filtration (3.5 g). The filtrate is subjected to column chromatography (eluent: dichloromethane / petroleum ether=1:1, volume ratio), the intermediate pre-3m8mND can be separated, and the raw material 2-methyl-3-methoxymethyl acrylate can be recovered simultaneously 4.5g.

[0083] The intermediate p...

Embodiment 3

[0088] The synthetic route involved in the present embodiment is as follows:

[0089]

[0090] (1) Synthesis of Ac-CND (3-cyano-4-hydroxy-6-acetyl-1,5-naphthyridine, 6-acetyl-4-hydroxy-1,5-naphthyridine-3-carbonitrile):

[0091] The synthesis of Ac-CND is similar to 8mCND, except that the raw material 4-methyl-3-aminopyridine is replaced by 2-acetyl-5-aminopyridine. 2-Acetyl-5-aminopyridine is obtained by reacting 2-cyano-5-aminopyridine with methyl Grignard reagent.

[0092] Intermediate pre-AcCND yield 63%. 1 H NMR (300MHz, CDCl 3 , δ): 10.96 (br, d, J = 12.8Hz, 1H), 8.47 (d, J = 2.7Hz, 1H), 8.12 (d, J = 8.7Hz, 1H), 7.93 (d, J = 13.2Hz , 1H), 7.54(dd, J=8.7, 2.7Hz, 1H), 4.34(q, J=7.2Hz, 2H), 2.71(s, 3H), 1.39(t, J=7.2Hz, 3H).MS (m / z, ESI): calcd for C 13 h 13 N 3 o 3 259, found 260 (+H + ).

[0093] The yield of the product Ac-CND was 40%. 1 H NMR (300MHz, DMSO-d6, δ): 13.13(br, s, 1H), 8.88(s, 1H), 8.27(d, J=8.7Hz, 1H), 8.19(d, J=8.7Hz, 1H ), 2.71(s, 3H).MS(m...

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Abstract

Disclosed in the present invention is a rare earth europium coordination complex and applications using the same as a light emitting material. The europium coordination complex has a structural formula of Eu(ND)xAyLm, wherein ND is a 4-hydroxy-1,5-naphthyridine anion ligand, A is another anion ligand, L is a neutral ligand; x = l, 2 or 3, y = 0, 1 or 2, and x+y = 3; m = 0, 1, 2 or 3. Such europium coordination complexes have a high-efficient photoluminescence quantum yield, good thermal stability and a good carrier transmission efficiency, and can be used as photoluminescent and electroluminescent materials.

Description

technical field [0001] The invention relates to the field of rare earth complex luminescent materials, in particular to a novel rare earth europium complex with high-efficiency photoluminescence and electroluminescence properties. Background technique [0002] As we all know, in the 21st century, energy will be a difficult problem that must be solved for the development and progress of human society. While people are developing new energy sources, "saving expenditure" will also be an important measure. In terms of living energy consumption, lighting alone accounts for about 20% of the total energy consumption. However, the energy utilization efficiency of current lighting sources still cannot achieve satisfactory results. LED (Light-emitting Diode) light source has attracted much attention due to its high energy conversion rate. Especially OLED (Organic Light-emitting Diode, organic light-emitting diode), which has potential advantages such as large area, flexibility, ult...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/00C07D471/04C09K11/06
CPCC07D471/04C09K11/06H05B33/14C09K2211/1029C09K2211/182C07F5/003H10K85/351H10K85/324H10K2102/103C07F5/00C07F1/08H10K50/00
Inventor 卞祖强卫慧波丁飞黄春辉
Owner PEKING UNIV