Novel 1,8-naphthalimide derivative compound organic electroluminescent main material and device

A technology of naphthalimide and host material, applied in the field of organic electroluminescence materials, can solve the problems of unsatisfactory electroluminescence performance and the like

Inactive Publication Date: 2014-08-20
SICHUAN UNIV
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Problems solved by technology

The current research work mainly focuses on the effect of TTA process on the luminous efficiency of OLED devices, using common materials with TFDF properties, such as anthracene derivatives, tris(8-hydroxyquinoline aluminum) and rubrene, etc.【 Phys. Rev. Lett., 2009, 102, 087404; Appl. Phys. Lett., 2009, 94, 083307; Appl. Phys. Lett i>., 2013, 103, 263301], the overall electroluminescent performance is often not ideal

Method used

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  • Novel 1,8-naphthalimide derivative compound organic electroluminescent main material and device
  • Novel 1,8-naphthalimide derivative compound organic electroluminescent main material and device
  • Novel 1,8-naphthalimide derivative compound organic electroluminescent main material and device

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Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1: the synthesis of NI-1

[0040]

[0041] 1. Compound 4-bromo-N-(4-tert-butylphenyl)-1,8-naphthalimide ( 1 )Synthesis

[0042] Into a 250 mL three-necked flask, add 5.0 g (18.05 mmol) 4-bromo-1,8-naphthalene anhydride, 3.23 g (21.64 mmol) 4-tert-butylaniline and 150 mL EtOH, heat to reflux for 14 h, and cool to At room temperature, spin off the solvent to obtain a solid, and recrystallize from acetone to obtain white needle-like crystals, with a yield of 81.1%. Melting point: 292-293°C. 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 8.71 (dd, J = 7.2, 0.8 Hz, 1H), 8.65 (dd, J = 8.4, 0.8 Hz, 1H), 8.47 (d, J = 8.0 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H), 7.91 (t, J 1 = 7.2 Hz, J 2 = 8.4 Hz, 1H), 7.57 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 8.8 Hz, 2H), 1.38 (s, 9H).

[0043] 2. 4-(3-bromophenoxy)-N-(4-tert-butylphenyl)-1,8-naphthalimide ( 2 )Synthesis

[0044] To a 250 mL three-necked bottle, add 0.5 g (1.23 mmol) 1 , 0.30 g (1.9 mmol) m-bromophenol, 0...

Embodiment 2

[0047] Embodiment 2: the synthesis of NI-2

[0048]

[0049] 1. 4-(3,5-dibromophenoxy)-N-(4-tert-butylphenyl)-1,8-naphthalimide ( 3 )Synthesis

[0050] To a 250 mL three-necked bottle, add 0.5 g (1.23 mmol) 1 , 0.30 g (1.9 mmol) m-bromophenol, 0.29 g (2.1 mmol) K 2 CO 3 React with 30 mL of DMF in an oil bath at 100 °C for 4 h, then cool to room temperature, pour the reaction solution into 150 mL of water, and filter with suction to obtain a yellow solid. The product was subjected to silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1:4) to obtain a yellow solid with a yield of 65 % and a melting point of 274-276 °C. 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 8.77 (d, J = 7.6 Hz, 1H), 8.67 (d, J = 7.2 Hz, 1H), 8.23 ​​(d, J = 7.6 Hz, 2H), 8.08 (d, J = 7.6 Hz, 1H), 7.94 (d, J = 8.0 Hz, 1H), 7.59 (d, J = 8.4 Hz, 1H), 7.45 (t, d, J 1 = 8.8 Hz, J 2 = 7.2 Hz, 1H), 7,6 (d, J = 8.4 Hz, 2H), 7.3 (d, J = 8.4 Hz, 2H), 7.06 (d, J = 7.6 Hz,...

Embodiment 3

[0053] Embodiment 3: the synthesis of NI-3

[0054]

[0055] NI-3 Synthesis

[0056] To a 250 mL round bottom flask, add 0.5 g (0.87 mmol) 2 , 0.81 g (1.91 mmol) 3-(4,4,5,5-tetramethyl-[1,3,4]dioxaborolane-9-(N-(4-tert-butylphenyl ))-9 H -carbazole, 0.03 g (0.026 mmol) Pd (pph 3 ) 4 , 12 mL NaCO 3 (2 M, aq.) and 40 mL of toluene were reacted in an oil bath at 100 °C for 24 h. After the reaction was finished, cool to room temperature, pour the reaction solution into 150 mL of water, and extract with dichloromethane, anhydrous Na 2 SO 4 After drying, spin off the solvent, silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1 / 10) gave a yellow solid, yield: 57.4%, melting point: 301-302 °C. 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 8.84-8.81 (dd, J = 9.6, 7.2 Hz, 1H), 8.73-8.71 (dd, J = 8.0, 6.4 Hz, 1H), 8.54-8.52 (d, J = 8.0 Hz, 1H), 8.36 (s, 1H), 8.18-8.16 (d, J = 7.6 Hz, 1H), 7.86-7.82 (t, J = 7.6 Hz,1H), 7.69-7.40 (m,14H), 7.31-7.27 (...

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Abstract

The invention discloses a series of novel 1,8-naphthalimide derivative compounds with triplet state fusion delayed fluorescence (TFDF) properties, and a preparation method and application thereof to electroluminescent devices. The molecules are used as the organic electroluminescent main materials, and can be prepared into high-efficiency yellow, orange and red organic light-emitting diodes; and the utilization rate of the exciton can substantially exceed the theory limit of singlet exciton utilization rate (25%, namely the external quantum yield of 5%). Therefore, the materials are promising main materials with TFDF properties, and the design and synthesis of the materials have important theoretical and practical significance to increase luminous efficiency of electroluminescence devices and promote the industrialization process of the electroluminescence devices.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and particularly relates to a novel host material with triplet state fusion ability which can be used to prepare yellow, orange and red electroluminescent devices. Specifically, the present invention relates to a series of 1,8-naphthoimide derivative compounds with delayed fluorescence properties and a preparation method thereof, and the 1,8-naphthoimide derivative compounds as host materials in existing Applications in the field of electromechanical luminescence. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted considerable attention due to their potential applications in full-color displays and lighting. According to the light-emitting mechanism, OLEDs can be divided into two categories: phosphorescent OLEDs and fluorescent OLEDs. Among them, phosphorescent OLEDs can use triplet excitons and singlet excitons at the same time, so the luminou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D401/14C07D221/14C09K11/06H01L51/54
CPCC09K11/06C07D221/14C07D401/12C07D401/14C09K2211/1029H10K85/6572
Inventor 卢志云周洁王宁郑徐军黄艳
Owner SICHUAN UNIV
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