CN103484105B - Red light organic electroluminescent materials and devices - Google Patents

Red light organic electroluminescent materials and devices Download PDF

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CN103484105B
CN103484105B CN201310396364.1A CN201310396364A CN103484105B CN 103484105 B CN103484105 B CN 103484105B CN 201310396364 A CN201310396364 A CN 201310396364A CN 103484105 B CN103484105 B CN 103484105B
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nim
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卢志云
郑徐军
王毅
黄艳
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Sichuan University
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Abstract

The invention discloses organic electroluminescent materials capable of emitting bright red light at a solid powder state. The compounds, namely the organic electroluminescent materials, contain 7H-benzimidazole [2, 1-a) naphtho [de] isoquinolyl-7-keto structure units, and a triarylated amine derivative with vinyl is introduced into the 4-site of the structure unit, so that the maximal fluorescence emission wavelengths of the electroluminescent materials at the solid powder state are larger than 600 nm, and the color of the emitted light is pure red. The electroluminescent materials can be used as guest materials to be prepared into organic electroluminescent red light devices with high doping concentration (6wt%), the maximal electroluminescent wavelengths of the devices are larger than 620 nm, and the luminous efficiency and brightness of the devices are high.

Description

Ruddiness organic electroluminescent fluorescent materials and device
Technical field
The invention belongs to field of organic electroluminescent materials, particularly the red electroluminescent fluorescent materials of a class.Specifically, the present invention relates to the organic electroluminescence red light material of a class with 7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone fluorescent chromophore.
Background technology
Organic electroluminescence device (OLED) is described as " third generation flat panel display ", causes the extensive concern of people in recent years.In the red, green, blue three primary colours device needed for total colouring, the current efficiency of green glow OLED close to 30cd/A[J.Appl.Phys., 2010,108,024510], can meet practical requirement; The maximum current efficiency of pure Nan dian Yao also reaches 9.1cd/A[Org.Electron., 2011,12,1068].By contrast, although the maximum current efficiency of red device can reach 12cd/A, this efficiency obtains under the low doping concentration of 0.5wt%, and this is because red light material often has caused by more serious concentration quenching problem.Along with the increase of ruddiness guest materials doping content, the luminous efficiency of device can sharply decline [J.Lumin., 2007,122-123,636].And so low doping content will bring problem [Adv.Mater., 2002,14,1072 such as complex manufacturing technology, poor reproducibility of device; Chem.Mater., 2004,16,4389].Therefore, industry wishes that exploitation can for the preparation of the novel red electroluminescent material of high-dopant concentration device.
7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone is the important fluorescent chromophore of a class.The fluorescent material built based on it generally has good light, heat, chemical stability, has been widely used as fluorescence dye [Dyes and Pigments, 2009,82,238] and fluorescent optical sensor [Bull.Chem.Soc.Jpn., 2001,74,173; The field such as Org.Biomol.Chem., 2012,10,8076], but they are in application also less [Eur.Phys.J.Appl.Phys., 2007,38,227 of photoelectric field; Polymer, 2009,50,5668].In addition, due to 7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone is the electron acceptor(EA) structural unit of an electron deficiency, therefore, when introducing the substituting group of different electron supplying capacity to its 3-position or 4-position, can tuning gained give-the fluorescence color of acceptor (D-A) structural molecule.Such as: to its 4-position introduce alkyl or aryl replace amino time, yellowish green photoemissive D-A molecule [Dyes and Pigments, 2009,80,279] can be obtained; When introducing aryloxy to its 4-position, then can obtain bluish-green photoemissive D-A molecule [J.Soc.Dyers Colourists., 1989,105,29].But up to the present, also not yet have the 7H-benzoglyoxaline of red emission also [2,1-a] benzo [de] isoquinolyl-7-ketone derivatives be seen in report.
Summary of the invention
Because red light material often has more serious concentration quenching problem, cause ruddiness OLED in prior art usually to adopt host-guest system structure, and the doping content of ruddiness guest materials is general lower.In order to address this problem, the invention provides 7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketones derivant that a class can send bright red fluorescence in the solid state.During used as guest emitting material, can prepare ruddiness OLED that is efficient, high-dopant concentration, be the organic electroluminescence red light material of a class excellent performance.The present invention also provides the synthetic method of above-claimed cpd.
Design of the present invention is: with 7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone is electron donor(ED) (D) unit as electron acceptor(EA) (A) structural unit, with triaryl amine, vinyl is pi-conjugated bridging unit, construct the D-π-A molecule with larger conjugation degree, enable its fluorescent emission be positioned at red spectral band; Above-mentioned D unit has larger spatial volume, A unit then introduces the steric group such as the tertiary butyl and trifluoromethyl, to effectively reducing intermolecular interaction, thus improve concentration quenching problem, acquisition can send the material of bright fluorescence when solid-state, and can for the preparation of the OLED of high-dopant concentration.
7H-benzoglyoxaline of the present invention is [2,1-a] benzo [de] isoquinolyl-7-ketone D-π-A red fluorescence molecule also, and its general structure is as follows:
Wherein R 1for hydrogen atom or the tertiary butyl; R 2for hydrogen atom or trifluoromethyl; Ar 1for benzene-Isosorbide-5-Nitrae-two base, 9,9-diphenylfluorene-2,7-bis-bases or spiral shell fluorenes-2,7-bis-base; Ar 2for phenyl or 1-naphthyl.Further, organic electroluminescence red light material provided by the present invention, its Ar 1, Ar 2, R 1, R 2assembly have following 12 kinds of forms:
Organic electroluminescence ruddiness compound provided by the present invention, its preparation technology mainly comprises following three steps: 1) prepare the bromo-11-tertiary butyl of 4--7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone or the bromo-10-trifluoromethyl of 4--7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (A unit); 2) triarylamine derivative with vinyl on aryl is prepared, i.e. D-π unit; 3) by Heck linked reaction, A unit and D-π unit are coupled together, obtain target compound.Above-mentioned technique is carried out all at ambient pressure, and concrete operations and processing condition are explained by embodiment.
7H-benzoglyoxaline provided by the present invention is [2,1-a] benzo [de] isoquinolyl-7-ketones derivant also, and its pressed powder all can send red fluorescence under ultraviolet-visible optical excitation, maximum emission wavelength λ pLmaxall more than 600nm, show that they are red light materials that a class concentration quenching problem obtains effectively improving; The OLED of the 6wt% high-dopant concentration that it can be used as light emitting guest material to prepare, all can send high brightness, efficiently red electroluminescent, show that they are the promising red electroluminescent materials of a class.
Red light material of the present invention can be used for making organic electroluminescence fluorescent device, and its manufacture craft is known, ripe technique [J.Phys.Chem.C., 2010,114,5193], therefore is not described at this.Made EL device structure is: ITO/NPB (30nm)/Alq 3: NIM-1 ~ NIM-12 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm).Wherein, ITO is the indium oxide tin glass of conduction, as the anode of device; NPB is N, N '-two (1-naphthyl)-N, N '-phenylbenzene biphenyl-4,4 '-diamines, plays transporting holes; Alq 3being that three (oxines) close aluminium, is doped body material; Bphen is 4,7-phenylbenzene-1,10-phenanthroline, plays transmission electronic; Mg:Ag is magnesium alloy silver electrode, as the negative electrode of device.
The fluorescence property of red light material of the present invention under pressed powder state and list in table 1 using its performance as the electroluminescent device of the 6wt% doping content prepared by guest materials.
The fluorescence property of table 1 red light material provided by the invention under pressed powder state and with the performance of the OLED of its 6wt% doping prepared 1
Note: 1. all data are all the same time, similarity condition, record on same instrument;
2. fluorescence emission spectrum records under the shooting conditions of 480nm.
Beneficial effect
Organic electroluminescence ruddiness compound provided by the present invention has following beneficial effect:
1. provided by the present invention with 7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone fluorescent emission group organic electroluminescence ruddiness compound N IM-1 ~ NIM-12, its pressed powder under the excited by visible light of 480nm, λ pLmaxall be greater than 600nm, glow color is pure red.
2, organic electroluminescence ruddiness compound N IM-1 ~ NIM-12 provided by the present invention, all can be used as guest emitting material, prepares the organic electroluminescence red device of high-dopant concentration, the maximum electroluminescent λ of device eLmaxall be greater than 620nm, simultaneously the luminous efficiency of device and brightness all higher.
Therefore, organic electroluminescence red light material provided by the present invention not only can issue out pure red fluorescence in pressed powder state, and the organic electroluminescence red device of high-dopant concentration can also be prepared as guest materials, the brightness of device is high, efficiency is high, is the promising red electroluminescent material of a class.
The concrete synthetic method of described organic electroluminescence ruddiness compound will be described in embodiment hereafter.
Below in conjunction with drawings and Examples, the present invention is further illustrated.
Accompanying drawing explanation
Fig. 1: compound N IM-1, NIM-2, NIM-3, NIM-4 fluorescence emission spectrogram under pressed powder state (luminous intensity through normalized, excitation wavelength: 480nm)
Fig. 2: compound N IM-5, NIM-6, NIM-7, NIM-8 fluorescence emission spectrogram under pressed powder state (luminous intensity through normalized, excitation wavelength: 480nm)
Fig. 3: compound N IM-9, NIM-10, NIM-11, NIM-12 fluorescence emission spectrogram under pressed powder state (luminous intensity through normalized, excitation wavelength: 480nm)
The electroluminescent spectrum figure (luminous intensity is through normalized) of Fig. 4: the OLED of the 6wt% doping content made for guest emitting material with compound N IM-1, NIM-2, NIM-3, NIM-4
The electroluminescent spectrum figure (luminous intensity is through normalized) of Fig. 5: the OLED of the 6wt% doping content made for guest emitting material with compound N IM-5, NIM-6, NIM-7, NIM-8
The electroluminescent spectrum figure (luminous intensity is through normalized) of Fig. 6: the OLED of the 6wt% doping content made for guest emitting material with compound N IM-9, NIM-10, NIM-11, NIM-12
Fig. 7: the 4-bromo-11-tertiary butyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (1) and the bromo-10-trifluoromethyl of the 4--7H-benzoglyoxaline also molecular structure of [2,1-a] benzo [de] isoquinolyl-7-ketone (2) and synthetic route
Fig. 8: the molecular structure of compound N IM-1, NIM-2, NIM-3, NIM-4 and synthetic route
Fig. 9: the molecular structure of compound N IM-5, NIM-6, NIM-7, NIM-8 and synthetic route
Figure 10: the molecular structure of compound N IM-9, NIM-10, NIM-11, NIM-12 and synthetic route
Embodiment
The synthetic method of above-claimed cpd is set forth further below in conjunction with accompanying drawing, and their fluorescent emission under pressed powder state and electroluminescent properties.
Embodiment 1
The synthesis of NIM-1 and fluorescence and electroluminescent properties:
The synthesis technique of NIM-1 comprises following three steps: the bromo-11-tertiary butyl of (1) synthesis 4--7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (being called for short compound 1); (2) 4-(N, N-diphenylamino) vinylbenzene (be called for short compound 3) (synthesis technique step can see Chem.Commun., 2013,49,5730) is synthesized; (3) compound 1 and 3 is obtained NIM-1 by Heck linked reaction.
1, the synthesis of compound 1
Bromo-1, the 8-naphthalic anhydride (1.80g, 6.5mmol) of 4-, 4-tert-butyl o phenylenediamine (1.5g, 9.1mol) and 50mL Glacial acetic acid is added, after being warming up to 110 DEG C of reaction 4h in 100mL mono-neck bottle.Cooling reaction solution, is poured in 500mL distilled water, separates out a large amount of yellow mercury oxide.Suction filtration, distilled water wash three times (each 30mL), dries and obtains yellow solid powder.Thick product is purified through column chromatography method (eluent: sherwood oil/methylene dichloride=60/1) and is obtained the bromo-11-tertiary butyl of 4--7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 1), for greenish yellow solid, productive rate is 17.7%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.93(d,J=8.2Hz,1H),8.68(s,1H),8.60–8.41(m,3H),8.19(s,1H),8.05(s,1H),7.79(s,1H),1.48(s,9H)。
2, the synthesis of compound 3
Compound 3 is raw material with triphenylamine, prepares through two-step reaction.Its concrete synthesis technique step can see Chem.Commun., and 2013,49,5730.
3, the synthesis of target compound NIM-1
Under argon shield, in 100mL two neck bottle, add compound 1(0.89g, 2.6mmol), compound 3(0.8g, 2.8mmol), palladium (0.012g, 5.2 × 10 -5mmol), three (o-methyl-phenyl-) phosphine (0.032g, 1.04 × 10 -4mmol), triethylamine (1.84g, 0.018mol), and 50mL DMF, after being warming up to 90 DEG C of reaction 24h, cooling reaction solution.Be poured in 200mL distilled water, use 50mL dichloromethane extraction, organic phase is washed three times (each 30mL) through saturated nacl aqueous solution, anhydrous sodium sulfate drying.Remove solvent under reduced pressure, obtain red solid.Thick product is purified through column chromatography method (eluent: sherwood oil/methylene dichloride=60/1) and is obtained NIM-1, is red solid powder, productive rate 18.2%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.82(d,J=7.2Hz,1H),8.72(d,J=7.6Hz,1H),8.62(s,1H),8.47(d,8.0Hz,1H),8.01(d,J=7.6Hz,1H),7.81-7.76(m,3H),7.55(dd,J=8.4Hz,J=1.6Hz,1H),7.51(d,J=8.8Hz,2H),7.33-7.29(m,5H),7.17-7.15(m,4H),7.12-7.07(m,4H),1.47(s,9H)。
Organic electroluminescence ruddiness compound N IM-1 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 618nm, fluorescence quantum efficiency is 14.3%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-1 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 10540cd/m 2, maximum luminous efficiency is 3.6cd/A, λ eLmaxbeing positioned at 622nm, is pure ruddiness.
Embodiment 2
The synthesis of NIM-2 and fluorescence and electroluminescent properties:
The synthesis technique of NIM-2 comprises following three steps: the bromo-10-trifluoromethyl of (1) synthesis 4--7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (being called for short compound 2); (2) 4-(N, N-diphenylamino) vinylbenzene (compound 3) is synthesized; (3) compound 2 and 3 is obtained NIM-2 by Heck linked reaction.
1, the synthesis of compound 2
The synthesis technique step of compound 2 is similar to the synthesis technique step of embodiment 1 compound 1, only raw material is replaced to 4-trifluoromethyl O-Phenylene Diamine by 4-tert-butyl o phenylenediamine.Gained compound 2 is yellow solid powder, productive rate 16.7%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.88(d,J=8.4Hz,1H),8.67(s,1H),8.59–8.52(m,3H),8.52–8.18(m,2H),7.60(s,1H)。
2, the synthesis of compound 3
The synthesis technique step of compound 3 is with embodiment 1.
3, the synthesis of target compound NIM-2
The synthesis technique step of NIM-2 is similar to the synthesis technique step of NIM-1 in embodiment 1, only changes compound 1 into compound 2.Gained NIM-2 is red solid, productive rate 18.3%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.87(d,J=7.8Hz,1H),8.82(d,J=12.0Hz,1H),8.52(s,1H),8.47(d,1H),8.02(d,1H),7.83-7.78(m,3H),7.56(dd,J=8.4Hz,J=12.6Hz,1H),7.53(d,J=8.8Hz,2H),7.35-7.32(m,5H),7.20-7.18(m,4H),7.15-7.09(m,4H)。
Organic electroluminescence ruddiness compound N IM-2 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 625nm, fluorescence quantum efficiency is 13.2%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-2 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 10320cd/m 2, maximum luminous efficiency is 3.5cd/A, λ eLmaxbeing positioned at 626nm, is pure ruddiness.
Embodiment 3
The synthesis of NIM-3 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-3 comprises following three steps: (1) the synthesis 4-bromo-11-tertiary butyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 1); (2) N-phenyl-N-(4-styryl) naphthyl-1-amine (being called for short compound 4) (synthesis technique step see J.Mater.Chem., 2011,21,14907) is synthesized; (3) compound 1 and 4 is obtained NIM-3 by Heck linked reaction.
1, the synthesis of compound 1
The synthesis technique step of compound 1 is with embodiment 1.
2, the synthesis of compound 4
Compound 4 be with phenylbenzene naphthyl-1-amine for raw material, prepare through two-step reaction.Its concrete synthesis technique step can see J.Mater.Chem., and 2011,21,14907.
3, the synthesis of target compound NIM-3
The synthesis technique step of NIM-3 is similar to the synthesis technique step of NIM-1 in embodiment 1, only changes compound 3 into compound 4.Gained NIM-3 is red solid, productive rate 15.3%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.82(d,J=8.2Hz,1H),8.79–8.51(m,4H),8.49(s,1H),8.09(s,1H),8.08–8.06(m,1H),8.08–7.48(m,10H),7.47(d,J=15.0Hz,2H),7.4–7.38(m,7H),7.35–7.31(m,4H),7.24(s,2H),7.23(s,2H),7.2–7.17(m,6H),7.15(d,1H),7.14(s,1H),6.95(d,1H),1.48(s,9H)。
Organic electroluminescence ruddiness compound N IM-3 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 620nm, fluorescence quantum efficiency is 21.1%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-3 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 11220cd/m 2, maximum luminous efficiency is 4.4cd/A, λ eLmaxbeing positioned at 623nm, is pure ruddiness.
Embodiment 4
The synthesis of NIM-4 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-4 comprises following three steps: (1) synthesis 4-bromo-10-trifluoromethyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 2); (2) N-phenyl-N-(4-ethenylphenyl) naphthyl-1-amine (compound 4) is synthesized; (3) compound 2 and 4 is obtained NIM-4 by Heck linked reaction.
1, the synthesis of compound 2
The synthesis technique step of compound 2 is with embodiment 2.
2, the synthesis of compound 4
The synthesis technique step of compound 4 is with embodiment 3.
3, the synthesis of target compound NIM-4
The synthesis technique step of NIM-4 is similar to the synthesis technique step of NIM-2 in embodiment 2, only changes compound 3 into compound 4.Gained NIM-4 is red solid, productive rate 16.6%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.85(d,J=8.4Hz,1H),8.75(d,J=8.0Hz,1H),8.66(s,2H),8.48(t,J=42.5Hz,5H),8.05(d,J=5.0Hz,2H),7.71(s,1H),7.53(s,1H),7.50(s,1H),7.47(s,2H),7.34(s,1H),7.20(s,2H),7.18(s,1H),7.09(d,J=10.0Hz,3H),7.00(s,1H),6.95(s,2H)。
Organic electroluminescence ruddiness compound N IM-4 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 626nm, fluorescence quantum efficiency is 19.3%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-4 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 11030cd/m 2, maximum luminous efficiency is 3.9cd/A, λ eLmaxbeing positioned at 630nm, is pure ruddiness.
Embodiment 5
The synthesis of NIM-5 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-5 comprises following three steps: (1) the synthesis 4-bromo-11-tertiary butyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 1); (2) N, N is synthesized, 9,9-tetraphenyl-7-vinyl-9H-fluorenes-2-amine (being called for short compound 6); (3) compound 1 and 6 is obtained NIM-5 by Heck linked reaction.
1, the synthesis of compound 1
The synthesis technique step of compound 1 is with embodiment 1.
2, the synthesis of compound 6
(1) synthesis of compound 5: under argon shield, adds bromo-9, the 9-diphenylfluorene (14.22g, 0.03mol) of 2,7-bis-, pentanoic (6.35g, 0.038mol), sodium tert-butoxide (11.52g, 0.12mol), Pd (OAc) in 250mL three-necked bottle 2(3.584g, 0.016mol), tri-butyl phosphine a tetrafluoro borate (0.58g, 0.002mol) and 20mL toluene, after being warming up to 110 DEG C of reaction 12h, cooling reaction solution.Be poured in 200mL distilled water, use 200mL dichloromethane extraction.Organic phase is washed three times (each 50mL) through saturated nacl aqueous solution, and anhydrous sodium sulfate drying, removes solvent under reduced pressure, obtains red solid.Thick product is purified through column chromatography method (eluent: petrol ether/ethyl acetate=30/1) and is obtained compound 5, is white solid powder, productive rate 60.2%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):7.95–7.76(m,3H),7.64(s,1H),7.42(s,1H),7.28–7.15(m,7H),7.09(m,4H),6.99(d,J=10.0Hz,8H),6.90(s,2H)。
(2) synthesis of compound 6: under argon shield, adds 5(1.20g, 2.53mmol in 50mL bis-neck bottle), tributylvinyl tin (0.88g, 2.78mmol), Pd (Ph 3p) 4(0.058g, 0.05mmol), 2,6 di t butyl phenol (0.06g, 0.28mmol) and 20mL toluene, after being warming up to 110 DEG C of reaction 12h, cooling reaction solution.Add 20mL shrend to go out reaction, then add the saturated potassium fluoride solution of 20mL and stir solids removed by filtration after 1h.Organic phase is washed three times (each 30mL) through saturated nacl aqueous solution, and anhydrous sodium sulfate drying, removes solvent under reduced pressure, obtains white solid.Thick product is purified through column chromatography method (eluent: sherwood oil) and is obtained compound 6, is white solid powder, productive rate 68.2%. 1HNMR(400MHz,CDCl 3，TMS)δ(ppm):7.83–7.66(m,3H),7.58(s,1H),7.38(s,1H),7.26–7.06(m,11H),6.99(d,J=10.0Hz,8H),6.90(s,2H),6.82(s,1H),5.76(s,1H),5.25(s,1H)。
3, the synthesis of target compound NIM-5
The synthesis technique step of NIM-5 is similar to the synthesis technique step of NIM-1 in embodiment 1, only changes compound 3 into compound 6.Gained NIM-5 is red solid, productive rate 15.3%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.84(d,J=7.9Hz,1H),8.66(s,1H),8.65–8.51(m,3H),8.19(s,1H),8.15(s,1H),7.93–7.76(m,3H),7.69(s,1H),7.48(s,1H),7.28(s,1H),7.27–7.24(d,J=10.0Hz,4H),7.25–7.13(m,7H),7.15(m,J=10.0Hz,8H),7.12(s,2H),7.02(s,1H),7.06(s,1H),1.46(s,9H)。
Organic electroluminescence ruddiness compound N IM-5 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 627nm, fluorescence quantum efficiency is 35.5%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-5 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 12960cd/m 2, maximum luminous efficiency is 5.1cd/A, λ eLmaxbeing positioned at 632nm, is pure ruddiness.
Embodiment 6
The synthesis of NIM-6 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-6 comprises following three steps: (1) synthesis 4-bromo-10-trifluoromethyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 2); (2) N, N is synthesized, 9,9-tetraphenyl-7-vinyl-9H-fluorenes-2-amine (being called for short compound 6); (3) compound 2 and 6 is obtained NIM-6 by Heck linked reaction.
1, the synthesis of compound 2
The synthesis technique step of compound 2 is with embodiment 2.
2, the synthesis of compound 6
The synthesis technique step of compound 6 is with embodiment 5.
3, the synthesis of target compound NIM-6
The synthesis technique step of NIM-6 is similar to the synthesis technique step of NIM-2 in embodiment 2, only changes intermediate 3 into intermediate 6.Gained NIM-6 is red solid, productive rate 15.9%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.84(d,J=8.2Hz,1H),8.69(s,1H),8.67–8.55(m,3H),8.22(s,1H),8.17(s,1H),7.92–7.83(m,3H),7.75(m,3H),7.61(s,1H),7.49(s,1H),7.32(d,J=16.0Hz,1H),7.30(s,1H),7.28–7.26(d,4H),7.25–7.23(m,4H),7.17(m,J=8.0Hz,8H),7.11(s,2H),7.01(d,J=16.0Hz,1H)。
Organic electroluminescence ruddiness compound N IM-6 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 638nm, fluorescence quantum efficiency is 30.2%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-6 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 12870cd/m 2, maximum luminous efficiency is 4.7cd/A, λ eLmaxbeing positioned at 638nm, is pure ruddiness.
Embodiment 7
The synthesis of NIM-7 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-7 comprises following three steps: (1) the synthesis 4-bromo-11-tertiary butyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 1); (2) N-(naphthalene-1-base)-N, 9,9-triphenyl-7-vinyl-9H-fluorenes-2-amine (being called for short compound 8) is synthesized; (3) compound 1 and 8 is obtained NIM-7 by Heck linked reaction.
1, the synthesis of compound 1
The synthesis technique step of compound 1 is with embodiment 1;
2, the synthesis of compound 8
(1) synthesis of compound 7: the synthesis technique step of compound 7 is similar to the synthesis technique step of embodiment 6 compound 5, only the pentanoic in raw material is replaced to phenyl napthyl-1-amine.Gained compound 7 is white solid, productive rate 59.9%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.23(s,1H),7.88–7.65(m,5H),7.67(s,1H),7.60(s,1H),7.54–7.43(m,4H),7.27(t,J=7.9Hz,7H),7.20(s,2H),7.10(d,J=10.0Hz,6H),7.01(s,1H)。
(2) synthesis of compound 8: the synthesis technique step of compound 8 is similar to the synthesis technique step of embodiment 6 compound 6, only by the N in raw material, N, 9,9-tetraphenyl-7-vinyl-9H-fluorenes-2-amine replaces to N-(naphthalene-1-base)-N, the bromo-9H-fluorenes of 9,9-triphenyl-7--2-amine.Gained compound 8 is white solid, productive rate 65.9%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.22(s,1H),7.80–7.63(m,5H),7.63(s,1H),7.58(s,1H),7.52–7.42(m,4H),7.24(t,J=7.9Hz,7H),7.18(s,2H),7.09(d,J=10.0Hz,6H),7.00(s,1H),6.72(s,1H),5.75(s,1H),5.24(s,1H)。
3, the synthesis of target compound NIM-7
The synthesis technique step of NIM-7 is similar to the synthesis technique step of NIM-1 in embodiment 1, only changes compound 3 into compound 8.Gained NIM-7 is red solid, productive rate 16.4%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.87d,J=8.1Hz,1H),8.59(s,1H),8.50–8.35(m,3H),δ8.32(s,1H),8.29(s,1H),8.11(s,1H),7.99(s,1H),7.83–7.75(m,5H),7.63(s,1H),7.58(s,1H),7.57–7.52(m,4H),7.53(t,J=8,0Hz,6H),7.48(s,2H),7.37–7.32(d,4H),7.29(d,J=10.0Hz,4H),7.15(s,1H),7.12(s,1H),1.47(s,9H)。
Organic electroluminescence ruddiness compound N IM-7 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 627nm, fluorescence quantum efficiency is 39.0%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-7 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 13620cd/m 2, maximum luminous efficiency is 5.8cd/A, λ eLmaxbeing positioned at 629nm, is pure ruddiness.
Embodiment 8
The synthesis of NIM-8 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-8 comprises following three steps: (1) synthesis 4-bromo-10-trifluoromethyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 2); Synthesis N-(naphthalene-1-base)-N, 9,9-triphenyl-7-vinyl-9H-fluorenes-2-amine (compound 8); (3) compound 2 and 8 is obtained NIM-8 by Heck linked reaction.
1, the synthesis of compound 2
The synthesis technique step of compound 2 is with embodiment 2.
2, the synthesis of compound 8
The synthesis technique step of compound 8 is with embodiment 7.
3, the synthesis of target compound NIM-8
The synthesis technique step of NIM-8 is similar to the synthesis technique step of NIM-2 in embodiment 2, only changes compound 3 into compound 8.Gained NIM-8 is red solid, productive rate 13.3%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.88(d,J=8.0Hz,1H),8.67(s,1H),8.59–8.52(m,3H),8.52–8.18(m,2H),7.60(s,1H),δ8.22(s,1H),7.80–7.63(m,5H),7.63(s,1H),7.58(s,1H),7.52–7.42(m,4H),7.35(d,1H),7.31(d,J=16.0Hz,1H),7.24(t,J=7.9Hz,7H),7.18(s,2H),7.09(d,J=10.0Hz,6H),7.00(d,J=16.0Hz,1H)。
Organic electroluminescence ruddiness compound N IM-8 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 639nm, fluorescence quantum efficiency is 36.8%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-8 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 13360cd/m 2, maximum luminous efficiency is 5.4cd/A, λ eLmaxbeing positioned at 638nm, is pure ruddiness.
Embodiment 9
The synthesis of NIM-9 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-9 comprises following three steps: (1) the synthesis 4-bromo-11-tertiary butyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 1); (2) N, N-phenylbenzene-7-vinyl-9,9 '-spiral shell fluorenes-2-amine (being called for short compound 10) is synthesized; (3) compound 1 and 10 is obtained NIM-9 by Heck linked reaction.
1, the synthesis of compound 1
The synthesis technique step of compound 1 is with embodiment 1.
2, the synthesis of compound 10
(1) synthesis of compound 9: the synthesis technique step of compound 9 is similar to the synthesis technique step of embodiment 5 compound 5, only replaces to 2,7-bis-bromo-9 by raw material by bromo-9, the 9-diphenylfluorene of 2,7-bis-, 9 '-spiral shell two fluorenes.Gained compound 9 is white solid powder, productive rate 56.3%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):7.82(s,2H),7.86(d,J=5.0Hz,2H),7.54(d,J=6.3Hz,3H),7.40(s,1H),7.35(s,1H),7.25(s,2H),7.17(t,J=2.5Hz,7H),6.70(s,4H),6.90(s,2H)。
(2) synthesis of compound 10: the synthesis technique step of compound 10 is similar to the synthesis technique step of embodiment 5 compound 6, only by raw material by N, N, 9, the bromo-9H-fluorenes of 9-tetraphenyl-7--2-amine replaces to N, N-phenylbenzene-7-bromo-9,9 '-spiral shell fluorenes-2-amine.Gained compound 10 is white solid powder, productive rate 50.6%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):7.75(d,J=5.0Hz,2H),7.51(d,J=6.3Hz,3H),7.38(s,1H),7.32(s,1H),7.24(s,2H),7.14(t,J=2.5Hz,7H),6.98(s,4H),6.90(s,2H),6.70(s,1H),5.71(s,1H),5.21(s,1H)。
3, the synthesis of target compound NIM-9
The synthesis technique step of NIM-9 is similar to the synthesis technique step of NIM-1 in embodiment 1, only changes compound 3 into compound 10.Gained NIM-9 is red solid, productive rate 15.8%. 1HNMR(400MHz,CDCl 3，TMS)δ(ppm):8.83(d,J=7.8Hz,1H),8.59(s,1H),8.51–8.41(m,3H),8.49(s,1H),8.39(s,1H),7.96(s,1H),7.85(s,2H),7.71(d,J=5.0Hz,2H),7.59(d,J=6.3Hz,3H),7.39(s,1H),7.34(s,1H),7.31(d,J=16.0Hz,1H),7.26(s,2H),7.17(t,J=2.5Hz,7H),7.11(s,4H),7.09(s,2H),7.08(d,J=16.0Hz,1H),1.47(s,9H)。
Organic electroluminescence ruddiness compound N IM-9 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 618nm, fluorescence quantum efficiency is 48.7%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-9 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 15100cd/m 2, maximum luminous efficiency is 6.4cd/A, λ eLmaxbeing positioned at 620nm, is pure ruddiness.
Embodiment 10
The synthesis of NIM-10 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-10 comprises following three steps: (1) synthesis 4-bromo-10-trifluoromethyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 2); (2) N, N-phenylbenzene-7-vinyl-9,9 '-spiral shell fluorenes-2-amine (compound 10) is synthesized; (3) compound 2 and 10 is obtained NIM-10 by Heck linked reaction.
1, the synthesis of compound 2
The synthesis technique step of compound 2 is with embodiment 2.
2, the synthesis of compound 10
The synthesis technique step of compound 10 is with embodiment 9.
3, the synthesis of target compound NIM-10
The synthesis technique step of NIM-10 is similar to the synthesis technique step of NIM-2 in embodiment 2, only changes compound 3 into compound 10.Gained NIM-10 is red solid, productive rate 17.1%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.85(d,J=8.2Hz,1H),8.67(s,1H),8.59–8.40(m,3H),8.23(s,1H),8.20(s,1H),8.08(s,1H),7.93(s,2H),7.90(s,3H),7.69(s,1H),7.79–7.55(m,6H),7.80(s,1H),7.50(s,1H),7.46(d,J=8.2Hz,2H),7.44(s,2H),7.31(d,J=16.0Hz,1H),7.24(d,J=7.4Hz,3H),7.15(s,1H),7.09(s,2H),7.04(s,1H),6.99(d,J=16.0Hz,1H),1.48(s,9H)。
Organic electroluminescence ruddiness compound N IM-10 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 632nm, fluorescence quantum efficiency is 43.2%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-10 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 14900cd/m 2, maximum luminous efficiency is 6.2cd/A, λ eLmaxbeing positioned at 633nm, is pure ruddiness.
Embodiment 11
The synthesis of NIM-11 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-11 comprises following three steps: (1) the synthesis 4-bromo-11-tertiary butyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 1); (2) N-(naphthalene-1-base)-N-phenyl-7-vinyl-9,9 '-spiral shell fluorenes-2-amine (being called for short compound 12) is synthesized; (3) compound 1 and 12 is obtained NIM-11 by Heck linked reaction.
1, the synthesis of compound 1
The synthesis technique step of compound 1 is with embodiment 1.
2, the synthesis of compound 12
(1) synthesis of chemical combination 11: the synthesis technique step of compound 11 is similar to the synthesis technique step of embodiment 9 compound 9, only raw material is replaced to phenyl napthyl-1-amine by pentanoic.Gained compound 9 is white solid powder, productive rate 60.3%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.26(s,1H),7.93(s,2H),7.87(d,J=5.0Hz,3H),7.73(s,1H),7.82–7.54(m,6H),7.56(s,1H),7.54(d,J=4.0Hz,2H),7.39(s,2H),7.25(d,J=1.4Hz,3H),7.15(s,1H),7.10(s,2H),7.03(s,1H)。
(2) synthesis of compound 12: the synthesis technique step of compound 12 is similar to the synthesis technique step of embodiment 9 compound 10, only by raw material by N, N-phenylbenzene-7-bromo-9,9 '-spiral shell fluorenes-2-amine replaces to N-(naphthalene-1-base)-N-phenyl-7-bromo-9,9 '-spiral shell fluorenes-2-amine.Gained compound 12 is white solid powder, productive rate 50.8%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.25(s,1H),7.90(s,2H),7.85(d,J=5.0Hz,3H),7.69(s,1H),7.81–7.52(m,6H),7.50(s,1H),7.44(d,J=4.0Hz,2H),7.34(s,2H),7.24(d,J=1.4Hz,3H),7.13(s,1H),7.08(s,2H),7.00(s,1H),6.71(s,1H),5.74(s,1H),5.23(s,1H)。
3, the synthesis of target compound NIM-11
The synthesis technique step of NIM-11 is similar to the synthesis technique step of NIM-1 in embodiment 1, only changes compound 3 into compound 12.Gained NIM-11 is red solid, productive rate 16.5%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.85(d,J=8.2Hz,1H),8.67(s,1H),8.59–8.40(m,3H),8.23(s,1H),8.20(s,1H),8.08(s,1H),7.93(s,2H),7.90(s,3H),7.69(s,1H),7.79–7.55(m,6H),7.80(s,1H),7.50(s,1H),7.46(d,J=8.2Hz,2H),7.44(s,2H),7.31(d,J=16.0Hz,1H),7.24(d,J=7.4Hz,3H),7.15(s,1H),7.09(s,2H),7.04(s,1H),6.99(d,J=16.0Hz,1H),1.48(s,9H)。
Organic electroluminescence ruddiness compound N IM-11 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 621nm, fluorescence quantum efficiency is 56.8%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-11 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 16840cd/m 2, maximum luminous efficiency is 7.2cd/A, λ eLmaxbeing positioned at 623nm, is pure ruddiness.
Embodiment 12
The synthesis of NIM-12 and fluorescence and electroluminescent properties:
The synthesis technique step of NIM-12 comprises following three steps: (1) synthesis 4-bromo-10-trifluoromethyl-7H-benzoglyoxaline also [2,1-a] benzo [de] isoquinolyl-7-ketone (compound 2); (2) N-(naphthalene-1-base)-N-phenyl-7-vinyl-9,9 '-spiral shell fluorenes-2-amine (compound 12) is synthesized; (3) compound 2 and 12 is obtained NIM-12 by Heck linked reaction.
1, the synthesis of compound 2
The synthesis technique step of compound 2 is with embodiment 2.
2, the synthesis of compound 12
The synthesis technique step of compound 12 is with embodiment 11.
3, the synthesis of target compound NIM-12
The synthesis technique step of NIM-12 is similar to the synthesis technique step of NIM-2 in embodiment 2, only changes compound 3 into compound 12.Gained NIM-12 is red solid, productive rate 14.8%. 1HNMR(400MHz,CDCl 3,TMS)δ(ppm):8.85(d,J=8.2Hz,1H),8.67(s,1H),8.59–8.40(m,3H),8.23(s,1H),8.20(s,1H),8.08(s,1H),7.93(s,2H),7.90(s,3H),7.69(s,1H),7.79–7.55(m,6H),7.80(s,1H),7.50(s,1H),7.46(d,J=8.2Hz,2H),7.44(s,2H),7.31(d,J=16.0Hz,1H),7.24(d,J=7.4Hz,3H),7.15(s,1H),7.09(s,2H),7.04(s,1H),6.99(d,J=16.0Hz,1H),1.48(s,9H)。
Organic electroluminescence ruddiness compound N IM-12 in the present embodiment can issue out red fluorescence in pressed powder state, its λ pLmaxbe positioned at 630nm, fluorescence quantum efficiency is 54.1%.It can be used as light emitting guest material, preparation there is ITO/NPB (30nm)/Alq 3: the electroluminescent device of NIM-12 (6wt%) (10nm)/Bphen (40nm)/Mg:Ag (200nm) structure, maximum luminousing brightness is 16100cd/m 2, maximum luminous efficiency is 6.9cd/A, λ eLmaxbeing positioned at 631nm, is pure ruddiness.

Claims (9)

1. ruddiness organic electroluminescent fluorescent materials, its structural formula is as follows:
Wherein:
R 1represent hydrogen atom or the tertiary butyl;
R 2represent hydrogen atom or trifluoromethyl;
Ar 1represent benzene-Isosorbide-5-Nitrae-two base, 9,9-diphenylfluorene-2,7-bis-bases or spiral shell fluorenes-2,7-bis-base;
Ar 2represent phenyl or 1-naphthyl.
2. ruddiness organic electroluminescent fluorescent materials as claimed in claim 1, is characterized in that R 1for the tertiary butyl, R 2for hydrogen atom, Ar 1for benzene-Isosorbide-5-Nitrae-two base, Ar 2for phenyl or 1-naphthyl.
3. ruddiness organic electroluminescent fluorescent materials as claimed in claim 1, is characterized in that R 1for hydrogen atom, R 2for trifluoromethyl, Ar 1for benzene-Isosorbide-5-Nitrae-two base, Ar 2for phenyl or 1-naphthyl.
4. ruddiness organic electroluminescent fluorescent materials as claimed in claim 1, is characterized in that R 1for the tertiary butyl, R 2for hydrogen atom, Ar 1be 9,9-diphenylfluorene-2,7-bis-base, Ar 2for phenyl or 1-naphthyl.
5. ruddiness organic electroluminescent fluorescent materials as claimed in claim 1, is characterized in that R 1for hydrogen atom, R 2for trifluoromethyl, Ar 1be 9,9-diphenylfluorene-2,7-bis-base, Ar 2for phenyl or 1-naphthyl.
6. ruddiness organic electroluminescent fluorescent materials as claimed in claim 1, is characterized in that R 1for the tertiary butyl, R 2for hydrogen atom, Ar 1for spiral shell fluorenes-2,7-bis-base, Ar 2for phenyl or 1-naphthyl.
7. ruddiness organic electroluminescent fluorescent materials as claimed in claim 1, is characterized in that R 1for hydrogen atom, R 2for trifluoromethyl, Ar 1for spiral shell fluorenes-2,7-bis-base, Ar 2for phenyl or 1-naphthyl.
8. ruddiness organic electroluminescent fluorescent materials as claimed in claim 1 is preparing the application in electroluminescent device.
9. ruddiness organic electroluminescent fluorescent materials as claimed in claim 8 is preparing the application in electroluminescent device, it is characterized in that: for the preparation of the luminescent layer of electroluminescent device.
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