Novel organic electroluminescent compound and organic electroluminescent device comprising same

Abstract

According to the invention, indolocarbazole is connected with a very good electron transmission material, namely a phenanthrene compound with a large pi conjugate structure, so that a classical indolo-phenanthrene-carbazole compound is formed; the introduction of different substituent groups enables a material to have better plane structure and conjugate system in comparison with a simple indolo-phenanthrene-carbazole compound. Under a condition that the luminous brightness is not changed, the luminous efficiency is remarkably improved in comparison with a contrast sample. 1,4-dibromo-2,5-dinitrobenzene and benzo[9,10]phenanthrene-2-boric acid are used as raw materials, synthesis and purification comparison processes are simple, the cost is low, and industrialized development demands can be met.

Description

technical field

[0001] The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising them. Specifically, it relates to novel organic electroluminescent compounds as electroluminescent materials and using them as an organic electroluminescent device. Background technique

[0002] Luminous efficiency is the most important factor in determining an OLED (Organic Light Emitting Diode) electroluminescent material type. Although fluorescent materials have been widely used as electroluminescent materials, at present, the luminous efficiency of phosphorescent materials is four times that of the theory, which is one of the best ways to improve the luminous efficiency.

[0003] So far, iridium(III) complexes are widely known as phosphorescent materials, including (acac)Ir(btp) 2 , Ir(PPy) 3 and Firpic for red, green and blue ones. In particular, many phosphorescent materials have been developed in Japan, Europe, and th...

Examples

Embodiment 1

[0035]

[0036] 10,16-dihydroindolo[3,2-B]phenanthrene[9,10-H]carbazole 7.19mmol, bromobenzene 21.65mmol, sodium tert-butoxide 30.18mmol, tris(dibenzylideneacetone) 400 mg of dipalladium and 100 mg of tri-tert-butylphosphine were dissolved in 60 ml of toluene, under nitrogen protection, and stirred at 90° C. for 3 hours. After the reaction was completed, cool to room temperature, extract three times with dichloromethane and water, evaporate the organic phase to dryness with anhydrous magnesium sulfate, and obtain 3.56 g of indolo[2,3-H]carbazole derivatives by column chromatography. 70%. Mass Spectrum: Calculated 708.86; Found 708.82. Elemental analysis: Calculated value: C: 91.50; H: 4.55; N: 3.95; Tested value: C: 91.53; H: 4.56; N: 3.91. 1 H NMR(500MHz,Chloroform) δ9.86(s,1H), 9.58(s,1H), 9.06(s,1H), 7.72(d,J=3.5Hz,1H), 7.68 (s,1H), 7.65 (dd, J=7.3, 3.5Hz, 1H), 7.63–7.55(m, 4H), 7.49 (d, J=10.0Hz, 4H).

Embodiment 2

[0038]

[0039] 10,16-dihydroindolo[3,2-B]phenanthrene[9,10-H]carbazole 7.19mmol, 2-bromonaphthalene 21.65mmol, sodium tert-butoxide 30.18mmol, tri(dibenzylidene Dissolve 400 mg of acetone) dipalladium and 100 mg of tri-tert-butylphosphine in 60 ml of toluene, under nitrogen protection, and stir at 90° C. for 3 hours. After the reaction was completed, cool to room temperature, extract three times with dichloromethane and water, evaporate the organic phase to dryness with anhydrous magnesium sulfate, and obtain 3.56 g of indolo[2,3-H]carbazole derivatives by column chromatography. 70%. Mass Spectrum: Calcd. 808.98; Tested 808.96. Elemental analysis: Calcd: C: 92.05; H: 4.49; N: 3.46; Tested: C: 92.03; H: 4.48; N: 3.49.

Embodiment 3

[0041]

[0042]10,16-dihydroindolo[3,2-B]phenanthrene[9,10-H]carbazole 7.19mmol, 2-bromophenanthrene 21.65mmol, sodium tert-butoxide 30.18mmol, tri(dibenzylidene Dissolve 400 mg of acetone) dipalladium and 100 mg of tri-tert-butylphosphine in 60 ml of toluene, under nitrogen protection, and stir at 90° C. for 3 hours. After the reaction was completed, cool to room temperature, extract three times with dichloromethane and water, evaporate the organic phase to dryness with anhydrous magnesium sulfate, and obtain 3.56 g of indolo[2,3-H]carbazole derivatives by column chromatography. 70%. Mass Spectrum: Calculated 909.10; Found 909.13. Elemental analysis: Calcd: C: 92.48; H: 4.44; N: 3.08; Tested: C: 92.46; H: 4.45; N: 3.10.

technical field

[0001] The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising them. Specifically, it relates to novel organic electroluminescent compounds as electroluminescent materials and using them as an organic electroluminescent device. Background technique

[0002] Luminous efficiency is the most important factor in determining an OLED (Organic Light Emitting Diode) electroluminescent material type. Although fluorescent materials have been widely used as electroluminescent materials, at present, the luminous efficiency of phosphorescent materials is four times that of the theory, which is one of the best ways to improve the luminous efficiency.

[0003] So far, iridium(III) complexes are widely known as phosphorescent materials, including (acac)Ir(btp) 2 , Ir(PPy) 3 and Firpic for red, green and blue ones. In particular, many phosphorescent materials have been developed in Japan, Europe, and th...

Examples

Embodiment 1

[0035]

[0036] 10,16-dihydroindolo[3,2-B]phenanthrene[9,10-H]carbazole 7.19mmol, bromobenzene 21.65mmol, sodium tert-butoxide 30.18mmol, tris(dibenzylideneacetone) 400 mg of dipalladium and 100 mg of tri-tert-butylphosphine were dissolved in 60 ml of toluene, under nitrogen protection, and stirred at 90° C. for 3 hours. After the reaction was completed, cool to room temperature, extract three times with dichloromethane and water, evaporate the organic phase to dryness with anhydrous magnesium sulfate, and obtain 3.56 g of indolo[2,3-H]carbazole derivatives by column chromatography. 70%. Mass Spectrum: Calculated 708.86; Found 708.82. Elemental analysis: Calculated value: C: 91.50; H: 4.55; N: 3.95; Tested value: C: 91.53; H: 4.56; N: 3.91. 1 H NMR(500MHz,Chloroform) δ9.86(s,1H), 9.58(s,1H), 9.06(s,1H), 7.72(d,J=3.5Hz,1H), 7.68 (s,1H), 7.65 (dd, J=7.3, 3.5Hz, 1H), 7.63–7.55(m, 4H), 7.49 (d, J=10.0Hz, 4H).

Embodiment 2

[0038]

[0039] 10,16-dihydroindolo[3,2-B]phenanthrene[9,10-H]carbazole 7.19mmol, 2-bromonaphthalene 21.65mmol, sodium tert-butoxide 30.18mmol, tri(dibenzylidene Dissolve 400 mg of acetone) dipalladium and 100 mg of tri-tert-butylphosphine in 60 ml of toluene, under nitrogen protection, and stir at 90° C. for 3 hours. After the reaction was completed, cool to room temperature, extract three times with dichloromethane and water, evaporate the organic phase to dryness with anhydrous magnesium sulfate, and obtain 3.56 g of indolo[2,3-H]carbazole derivatives by column chromatography. 70%. Mass Spectrum: Calcd. 808.98; Tested 808.96. Elemental analysis: Calcd: C: 92.05; H: 4.49; N: 3.46; Tested: C: 92.03; H: 4.48; N: 3.49.

Embodiment 3

[0041]

[0042]10,16-dihydroindolo[3,2-B]phenanthrene[9,10-H]carbazole 7.19mmol, 2-bromophenanthrene 21.65mmol, sodium tert-butoxide 30.18mmol, tri(dibenzylidene Dissolve 400 mg of acetone) dipalladium and 100 mg of tri-tert-butylphosphine in 60 ml of toluene, under nitrogen protection, and stir at 90° C. for 3 hours. After the reaction was completed, cool to room temperature, extract three times with dichloromethane and water, evaporate the organic phase to dryness with anhydrous magnesium sulfate, and obtain 3.56 g of indolo[2,3-H]carbazole derivatives by column chromatography. 70%. Mass Spectrum: Calculated 909.10; Found 909.13. Elemental analysis: Calcd: C: 92.48; H: 4.44; N: 3.08; Tested: C: 92.46; H: 4.45; N: 3.10.

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