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Organic metal iridium complex, electroluminescent material and application thereof

A technology of organometallic and iridium complexes, applied in the fields of luminescent materials, organic chemistry, compounds containing elements of Group 8/9/10/18 of the periodic table, etc. Red shift and other problems, to achieve the effect of improving luminescence performance, improving ligand coplanarity, and increasing coplanarity

Pending Publication Date: 2022-04-26
冠能光电材料(深圳)有限责任公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The invention provides a light-emitting organic metal complex formed by indolocarbazole-based light-emitting ligands and metal iridium. Because indolocarbazole or its derivatives are highly conjugative, it is beneficial to obtain pyridyl red organometallic complexes. The iridium complex solves the problem that the D-type luminescent complex molecule is too large to be sublimated in the above-mentioned background technology and the problem that the E-type luminescent iridium complex is only difficult to red-shift the green light, and at the same time solves the problem of the F-type iridium complex things are just a matter of reddish

Method used

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  • Organic metal iridium complex, electroluminescent material and application thereof
  • Organic metal iridium complex, electroluminescent material and application thereof
  • Organic metal iridium complex, electroluminescent material and application thereof

Examples

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Effect test

Embodiment 1

[0117] This embodiment provides an organometallic iridium complex II-1, the structural formula of which is as follows:

[0118]

[0119] The preparation method of this organometallic iridium complex II-1 comprises the following steps:

[0120] (1) Ligand synthesis

[0121]

[0122] Synthesis of Tm-2: Add Tm-1 (49.0g, 0.2mol), pinacol ester (76g, 0.3mol), KOAc (40g, 0.4mol), Pd 2 (dba) 3 (33.7g, 4mmol), S-Phos (3.3g, 8mmol) and dioxane (600mL), N 2 Protected, 110°C reflux reaction for 16h, cooled and then spin-dried, DCM was dissolved and mixed with silica gel powder, passed through a short column, concentrated, beaten with PE, and filtered to obtain Tm-2 as a yellow solid (42.0 g, 55% yield). Mass spectrometry detects m / e=293, theoretical molecular formula C 18 h 20 BNO 2 It is 293.17, and the HPLC purity test is 96%.

[0123] Synthesis of Tm-3: Add Tm-2 (42g, 0.14mol), o-bromopyridine (22g, 0.14mol), K 2 CO 3 (39g, 0.28mol), Pd (pph 3 ) 4 (43.2g, 2.8mmol), to...

Embodiment 2

[0131] This embodiment provides an organometallic iridium complex III-1, the structural formula of which is as follows:

[0132]

[0133] The preparation method of this organometallic iridium complex III-1 comprises the following steps:

[0134] (1) Ligand synthesis

[0135]

[0136] Synthesis of Tm-6: Add Tm-3 (16g, 65mmol), o-fluorobromobenzene (23g, 0.13mol), Cs 2 CO 3 (43g, 0.13mol) and DMF (180mL), 150°C under reflux for 16h in nitrogen, washed with water after cooling, extracted with DCM, dried over anhydrous sodium sulfate, purified by silica gel column and recrystallized from toluene to obtain Tm-6 as a white solid (6.6 g, 25% yield). Mass spectrometry m / e=399, theoretical molecular formula C 23 h 15 BrN 2 It is 398.29, and the HPLC purity test is 99%.

[0137] Synthesis of Tm-7: Add Tm-6 (7.4g, 18.6mmol), K 2 CO 3(5.2g, 37.2mmol), Pd(OAc) 2 (0.084g, 372mmo), t-Bu 3 PF 4 B (0.22g, 0.744mmol) and DMAc (50mL), N 2 Reflux reaction at 180°C for 16h under...

Embodiment 3

[0145] This embodiment provides an organometallic iridium complex IV-10, the structural formula of which is as follows:

[0146]

[0147] The preparation method of this organometallic complex IV-10 comprises the following steps:

[0148] (1) Ligand synthesis

[0149]

[0150] Synthesis of Tm-10: Add Tm-9 (42g, 150mmol), 1-fluoro-3methoxybenzene (22g, 180mol), Cs 2 CO 3 (97g, 0.3mol) and DMF (300mL), reflux reaction at 150°C in nitrogen for 16h, cooled, washed with water, extracted with DCM, dried over anhydrous sodium sulfate, purified by silica gel column and recrystallized from toluene to obtain Tm-10 as a white solid (46.2g, 80% yield); Mass spectrometry detects m / e=386, theoretical molecular formula C 19 h 13 BrClNO is 386.67, and the HPLC purity test is 99%.

[0151] Synthesis of Tm-11: Add Tm-10 (38g, 0.1mol), 4-deuteropicoline-2 borate (22g, 0.1mol), K 2 CO 3 (27.6g, 0.2mol), Pd (pph 3 ) 4 (1g, 1mmol), toluene (200mL), ethanol (70mL) and water (100mL), N ...

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Abstract

The invention provides an organic metal iridium complex, an electroluminescent material and application thereof. The organic metal iridium complex provided by the invention has a structure as shown in a formula I. Pyridine and carbazole (or indolocarbazole) are adopted as organic metal iridium luminescent ligands to synthesize a novel red luminescent material, and the pyridine (or substituted pyridine) leading LUMO and the carbazole (or indolocarbazole) leading HOMO are bonded to form the ligands. An N atom in carbazole or indolocarbazole is located at a para-position of a metal Ir bonded benzene ring, so that lone pair electron power supply on the N atom is favorably induced to an empty electron d orbit on the metal Ir, and a red-shifted metal-ligand charge transfer complex MLCT is formed; acetylacetone or a derivative thereof is used as an auxiliary ligand to form a metal iridium complex with metal iridium; the compound can be used as a photoluminescent material to be applied to biomedical fluorescence imaging, and can also be used as an organic light-emitting device OLED to be applied to products such as automobile taillights and panchromatic flat display screens.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to an organometallic iridium complex, an electroluminescent material and applications thereof. Background technique [0002] Organic semiconductor materials are new optoelectronic materials, and its large-scale research originated in 1977 by Hideki Shirakawa, A. Heeger and A. McDiamid jointly discovered doped polyacetylene with conductivity up to copper level. Subsequently, in 1987, C.Tang of Kodak Company invented the organic small molecule light-emitting diode (OLED), and in 1990, R.Friend and A.Holmes of Cambridge University invented the polymer light-emitting diode P-OLED, and in 1998, S.Forrest Invented with M.Thomson a more efficient organic phosphorescent light-emitting diode PHOLED. Because organic semiconductor materials have a structure that is easy to adjust, they can obtain a variety of varieties, adjustable energy bands, and even have ...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342H10K50/11
Inventor 李晓常黄辉殷正凯张建新
Owner 冠能光电材料(深圳)有限责任公司
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