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Iridium cooperation compound as near-infrared light-emitting material, and applications thereof

A technology of iridium complexes and luminescent materials, applied in luminescent materials, indium organic compounds, platinum group organic compounds, etc., can solve the problems of enhanced non-radiative decay of excited states, low luminous quantum efficiency of NIROLEDs, and low external quantum efficiency, etc. Highlights: Long half-life time, broad commercialization prospects, and simple synthesis methods

Active Publication Date: 2020-02-21
WUYI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage of NIR OLEDs based on platinum complexes is that the near-infrared light of such complexes is derived from the interaction between two or more platinum complex molecules at high concentrations (including Pt...Pt and π...π interactions ), they are easily formed based on dimers and oligomers (excimers) under light or electrical stimulation; while at low concentrations, the interaction between platinum complex molecules is limited, and its OLEDs devices The spectral emission peak is blue-shifted, and NIR OLEDs cannot be realized
The use of large-volume conjugated fused rings significantly increases the vibration of chemical bonds inside the material (such as: chemical bond rotation and stretching vibration), strengthens the non-radiative decay of excited states, and the energy gap law further aggravates the non-radiative energy loss of these excited states
Therefore, NIR OLEDs prepared with near-infrared iridium complexes based on large-volume conjugated fused rings have low luminous quantum efficiency (PLQY) (<20%) and low external quantum efficiency (EQE) (<6%).

Method used

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  • Iridium cooperation compound as near-infrared light-emitting material, and applications thereof
  • Iridium cooperation compound as near-infrared light-emitting material, and applications thereof
  • Iridium cooperation compound as near-infrared light-emitting material, and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of CNIr

[0031] (1) Preparation of 1-phenyl-4-cyanoisoquinoline:

[0032]

[0033] A 50ml flask was added with raw materials 1-chloro-4-cyanoisoquinoline (300mg, 1.59mmol), phenylboronic acid (290mg, 2.39mmol), potassium carbonate (439mg, 3.18mmol), palladium tetrakistriphenylphosphine (Pd(PPh 3 ) 4 ) (184mg, 0.16mmol), add 5ml of toluene, 0.75ml of ethanol and 2.5ml of water under the protection of nitrogen, and react at 95°C for 12 hours; then cool to room temperature, extract with ethyl acetate, pass through the column after rotary evaporation (ethyl acetate / Petroleum ether = 1 / 8, v / v) purification to obtain 241 mg of product, yield = 66%.

[0034] 1 H NMR (400MHz, CDCl 3 ,δ):8.98(s,1H),8.25(m,2H),7.92(m,1H),7.71(m,3H),7.57(m,3H);

[0035] 13 C NMR (100.5MHz, CDCl 3 ,δ): 165.0, 147.7, 138.3, 135.8, 132.7, 130.1, 129.9, 129.1, 128.8, 125.9, 124.7, 116.5, 104.9.

[0036] Matrix-assisted laser desorption ionization time-of-flig...

Embodiment 2

[0046] Embodiment 2: the preparation of t-BuCNIr:

[0047] (1) Preparation of 1-p-tert-butylphenyl-4-cyanoisoquinoline: similar to step (1) of Example 1, only the raw material phenylboronic acid was replaced with p-tert-butylphenylboronic acid. Yield = 76%.

[0048] 1 H NMR (400MHz, CDCl 3 ,δ):8.95(s,1H),8.30(d,J=8.4Hz,1H),8.25(d,J=8.4Hz,1H),7.9(m,1H),7.68(m,3H),7.59 (m,2H),1.40(s,9H);

[0049] 13 C NMR (100.5MHz, CDCl 3 ,δ): 164.9, 153.7, 147.6, 135.7, 135.4, 132.4, 129.9, 128.8, 125.8, 125.6, 124.5, 116.5, 104.5, 34.9, 31.3.

[0050] MALDI-TOF-MS: Molecular formula: Molecular formula: C 20 h 18 N 2 , Calculated: 286.3703; Measured: 287.0030.

[0051] (2) Preparation of dichloro(1-p-tert-butylphenyl-4-cyanoisoquinoline) iridium(III) dimer: similar to Example 1 step (2), only the raw material 1-chloro -4-cyanoisoquinoline was replaced by 1-p-tert-butylphenyl-4-cyanoisoquinoline.

[0052] (3) Preparation of t-BuCNIr: Similar to Example 1 step (3), only the raw mater...

Embodiment 3

[0056] Embodiment 3: the preparation of DCNIr:

[0057] (1) Preparation of 1-(3',5'-methylphenyl)-4-cyanoisoquinoline: Similar to step (1) in Example 1, only the raw material phenylboronic acid is replaced by 3,5-bis Tolylboronic acid. Yield = 65%.

[0058] 1 H NMR (400MHz, CDCl 3 ,δ):8.96(s,1H),8.25(dd,J=8.4Hz,0.8Hz,2H),7.92(m,1H),7.70(m,1H),7.30(s,1H),7.20(s ,1H),2.43(s,6H);

[0059] 13 C NMR (100.5MHz, CDCl 3 ,δ): 165.4, 147.5, 138.3, 138.1, 135.6, 132.5, 131.4, 128.9, 127.7, 125.9, 124.5, 116.4, 115.3, 104.6, 21.4.

[0060] MALDI-TOF-MS: Molecular formula: Molecular formula: C 18 h 14 N 2 , calculated value: 258.1157; measured value: 259.0741.

[0061] (2) Preparation of dichloro(1-(3',5'-methylphenyl)-4-cyanoisoquinoline) iridium(III) dimer: similar to step (2) of Example 1, Only the starting material 1-chloro-4-cyanoisoquinoline was replaced by 1-(3',5'-methylphenyl)-4-cyanoisoquinoline.

[0062] (3) Preparation of DCNIr: Similar to Example 1 step (3), only ...

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Abstract

The invention relates to an iridium cooperation compound as a near-infrared light-emitting material, wherein the iridium cooperation compound has a nitrogen-containing aromatic condensed ring structure, and an electron-withdrawing cyano group is introduced to the aromatic condensed ring. According to the invention, after the iridium cooperation compound as a the near-infrared light-emitting material is doped into a main body material and is used as a light-emitting layer in an organic near-infrared light-emitting diode, PLQY is about 45% at most and is remarkably higher than about 20% reportedin the prior art, and EQE is about 10% at most and is remarkably higher than 5-6% reported in the prior art; and the organic near-infrared light-emitting diode of the iridium cooperation compound hascharacteristics of excellent stability, high performance repeatability, long bright spot half-life period and long service life, wherein particularly a spectrum does not generate obvious displacementwhen a voltage is increased while other miscellaneous peaks do not occur, and the light color is not changed.

Description

technical field [0001] The invention belongs to the field of photoelectric materials, and in particular relates to an iridium complex as a near-infrared luminescent material and an application thereof. Background technique [0002] Luminescent materials and light-emitting devices are currently a hot topic in scientific research, attracting the research interest of many scholars at home and abroad and the widespread attention of the technology industry. Due to the ability to achieve 100% internal quantum efficiency (including 25% singlet state and 75% triplet state), phosphorescent materials have become one of the important branches of organic light-emitting materials. At present, organic near-infrared light-emitting diodes (NIR OLEDs) based on platinum (Pt(II)) complexes (hereinafter referred to as platinum complexes) have shown excellent performance: external quantum efficiency (EQE) = 24%, emission peak λem = 740nm. However, the disadvantage of NIR OLEDs based on platinu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342H10K50/12
Inventor 陈钊吴文海
Owner WUYI UNIV
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