CN102702075A - Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof - Google Patents
Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an organic electroluminescent material containing a tertiary aromatic amine structure. The organic electroluminescent material containing the tertiary aromatic amine structure is characterized in that: the structural formula is shown in the specifications; and in the structural formula, n1, n2 and n3 independently represent that the quantity of benzene ring is 0 or 1 respectively; a radical A represents a substituted carbazole radical; a radical B represents a structural radical containing substituted fluorenyl; and a structure C is a structure radical containing phenyl and substituted phenyl. The organic electroluminescent material is a fluorescent material which has high luminous efficiency; a result of the luminous efficiency in a solution can further indicate that the organic electroluminescent material which has high luminous efficiency and of which the brightness and performance can meet the industrial development can be applied to electroluminescent devices by serving as a luminous material or a luminous main body material or a transmission material. A synthesizing process has the advantages of reaction in two simple steps, easiness and convenience for operating, easiness for purifying, great increase in the industrial synthesizing yield, great reduction in cost, wide application, applicability to a plurality of materials for devices, and wide prospect. Meanwhile, a substituted radical is adjusted, so that the performance of the material further meets requirement of industrialization.
Description
Technical field
the present invention relates to the organic photoelectrical material field, especially relate to a kind of electroluminescent organic material that contains three arylamine structures.
Background technology
Exploitation to OLED (organic electroluminescence device) in
world wide has obtained very huge development; But progress along with application and development; Requirement to material is also increasingly high, more particularly can improve the luminous organic material of usefulness, because synthetic technology is relatively more difficult now; Purification difficult, the building-up process of some compound possibly also relate to the more virose raw material or the course of processing.Make OLED aspect industrialized development, make slow progress.
organic electroluminescent technology is the latest generation flat panel display, can be used for flat-panel monitor and lighting source, and present commercial flat-panel monitor puts goods on the market.Lighting source since himself absolute predominance also very soon with industrialization.Electroluminescent device has structure of whole solid state, and electroluminescent organic material is core and the basis that constitutes this device.The exploitation of novel material is to promote the continuous progressive driving source of electroluminescent technology.To original material prepn and device optimization also is the research focus of present organic electroluminescent industry.
since organic three arylamine structure applications in electroluminescent organic material; Make the electroluminescent organic material of three arylamine structures obtain good development; Material that some are classical such as NPB, TPD, the three arylamine structures that all right and wrong of TAPC are usually seen; Certain advantage is also arranged, particularly aspect cost with the technology maturity aspect.But the coupling of the quantum yield of this type material, life-span, brightness and novel material much all exists problem, is restricting the development of OLED industrialization, can not satisfy the demand of industrialization to material.And the cost of development of existing novel material is than higher; The synthesis technique more complicated; Synthesis technique and purifying technique are had relatively high expectations, and make that the cost of material is high, cause the OLED cost high; Because a lot of technical parameters such as the life-span of novel material, brightness, efficient do not reach industrialized growth requirement yet, how developing novel dynamical material is exactly OLED worker's task simultaneously.
Summary of the invention
the object of the present invention is to provide a kind of electroluminescent organic material that contains three arylamine structures; Difference through linking group, substituted radical; Can regulate the luminescent properties of material; Thereby realize the controllability of the performance of material, particularly the adjusting between blue light radiation dark blue and light blue.
another object of the present invention provides the easy synthetic route of a cover; Utilize the very little organic solvent of common toxicity as reaction solvent and processing solvent; Handle simply, cost is lower, can adapt to extensive industrialization needs; Design and develop a series of relevant organic materialss simultaneously, and provided the corresponding devices structure.
For realizing above-mentioned purpose, the present invention provides a kind of electroluminescent organic material that contains three arylamine structures, it is characterized in that: general structure is suc as formula shown in (1):
Wherein, it is 0 or 1 that n1, n2, n3 independently represent the number of phenyl ring respectively, and the A group is represented the substituted carbazole group, and concrete structure is (wherein * is the site that links to each other with phenyl ring or N) as follows:
The representative of B group contains the building stone that replaces fluorenyl, and concrete structure is (wherein * is the site that links to each other with phenyl ring or N) as follows:
C-structure is the building stone that contains phenyl and substituted-phenyl, and concrete structure is (wherein * is the site that links to each other with phenyl ring or N) as follows:
The present invention also provides the above-mentioned preparation method who contains the electroluminescent organic material of three arylamine structures, it is characterized in that:
Synthesizing of step 1, diaryl-amine compound
Under nitrogen protection system, take by weighing part fluorenyl aromatic amine a 100mmol, aryl halide b 110mmol puts into reaction system, adds KOH solid 400mmol (22.4g), adds the toluene 500ml of drying and dehydrating; Under nitrogen protection, Catalysts Cu I 10mmol, 1.10-phenanthroline 20mmol, nitrogen protection refluxed reaction 5-10 hour; Reacted cooling, suction filtration concentrates, and methylene dichloride is made solvent; Cross silica gel and do column chromatography, concentrate, obtain off-white color two amine products, subsequent use;
Synthesizing of step 2, triarylamine compounds
Take by weighing diaryl-amine compound 50mmol, carbazyl halogenide 55mmol, potassium tert.-butoxide 75mmol (8.4g) under nitrogen protection, adds catalyst P d (OAC) 2 22.5mmol; Tri-butyl phosphine 27mmol, under the nitrogen protection, backflow 4-8 hour, cool to room temperature; Suction filtration, solution concentration is made solvent with methylene dichloride, crosses silica gel column chromatography; Concentrate, use methylene dichloride, the sherwood oil recrystallization obtains the white solid triarylamine compounds.
The difference of the group that n1, n2, n3 and A, B, C represent separately in the structural formula according to the present invention (1), the concrete structure of the preferred electroluminescent organic material of the present invention is following:
The concrete number of A, B, C-structure and n1, n2, n3 is as shown in the table in the above structural formula:
| Numbering | n1 | n2 | n3 | A | B | C |
| M101 | 0 | 0 | 0 | A1 | B1 | C1 |
| M102 | 0 | 0 | 0 | A1 | B4 | C3 |
| M103 | 0 | 1 | 0 | A1 | B3 | C2 |
| M104 | 0 | 1 | 0 | A1 | B1 | C3 |
| M105 | 0 | 1 | 1 | A1 | B1 | C1 |
| M106 | 0 | 0 | 1 | A1 | B2 | C5 |
| M107 | 0 | 1 | 0 | A3 | B1 | C1 |
| M108 | 0 | 1 | 0 | A4 | B1 | C1 |
| M109 | 0 | 1 | 1 | A4 | B1 | C1 |
| M110 | 0 | 1 | 1 | A2 | B3 | C1 |
| M111 | 1 | 0 | 0 | A1 | B1 | C1 |
| M112 | 1 | 0 | 0 | A2 | B1 | C1 |
| M113 | 1 | 0 | 0 | A4 | B1 | C1 |
| M114 | 1 | 0 | 0 | A1 | B4 | C1 |
| M115 | 1 | 0 | 0 | A1 | B3 | C3 |
| M116 | 1 | 1 | 0 | A1 | B1 | C1 |
| M117 | 1 | 1 | 0 | A2 | B1 | C1 |
| M118 | 1 | 1 | 0 | A4 | B1 | C1 |
| M119 | 1 | 1 | 0 | A2 | B1 | C1 |
| M120 | 1 | 1 | 0 | A3 | B2 | C1 |
| M121 | 1 | 1 | 0 | A4 | B2 | C1 |
| M122 | 1 | 1 | 0 | A1 | B2 | C3 |
| M123 | 1 | 1 | 1 | A1 | B1 | C1 |
| M124 | 1 | 1 | 1 | A3 | B3 | C1 |
| M125 | 1 | 1 | 1 | A1 | B2 | C5 |
| M126 | 1 | 1 | 1 | A1 | B1 | C1 |
| M127 | 1 | 1 | 1 | A4 | B1 | C1 |
| M128 | 1 | 1 | 0 | A2 | B1 | C5 |
| M129 | 1 | 1 | 1 | A4 | B1 | C5 |
| M130 | 1 | 1 | 1 | A4 | B2 | C1 |
We can find through device data; This is that one type of luminous efficiency is than higher fluorescent material; Particularly through luminous efficiency result in the solution; More illustrative this be one type of luminous efficiency than higher, and brightness and performance all satisfy the electroluminescent organic material of industrialization development, can be used as luminescent material or luminous material of main part and transport material and be applied in the electroluminescent device.Synthesis technique is simple two-step reaction, and is simple to operation, and it is simple to purify, and the industrialization synthetic yield significantly improves, and cost significantly reduces, and is of many uses, can have a extensive future as in the multiple material of device.Simultaneously to the adjusting of substituted radical, make the performance of material reach the demand of industrialization more.
Embodiment
Embodiment 1 compound M101's is synthetic
Synthesizing of step 1, diaryl-amine compound:
Under nitrogen protection system, take by weighing part fluorenyl aromatic amine a 100mmol (20.9g), aryl halide b 110mmol (17.16g) puts into reaction system, adds KOH solid 400mmol (22.4g); The toluene 500ml that adds drying and dehydrating, under nitrogen protection, Catalysts Cu I 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g); Cooling has been reacted in nitrogen protection refluxed reaction 5 hours, and suction filtration concentrates; Methylene dichloride is made solvent, crosses silica gel and does column chromatography, concentrates; Obtain off-white color two amine product 26.22g, productive rate is more than 92%, and HPLC purity is greater than 98%.Can directly be used as next step reaction.
Synthesizing of step 2, triarylamine compounds (M101):
Take by weighing diaryl-amine compound 50mmol (14.25g), carbazyl halogenide 55mmol (17.66g), potassium tert.-butoxide 75mmol (8.4g) under nitrogen protection, adds catalyst P d (OAC) 222.5mmol (5.04g); Tri-butyl phosphine 27mmol under the nitrogen protection, refluxed cool to room temperature 4 hours; Suction filtration, solution concentration is made solvent with methylene dichloride, crosses silica gel column chromatography; Concentrate, use methylene dichloride, the sherwood oil recrystallization obtains white solid triarylamine compounds 22.36g.Productive rate is 85%.HPLC purity is greater than 98%.
Mass spectrum: calculated value is 526.24; Test value is 526.21.Ultimate analysis: calculated value C:88.94%; H:5.74%; N:5.32%; Test value is: C:88.91%; H:5.72%; N:5.30%.
Embodiment 2 compound M106's is synthetic
Synthesizing of step 1, diaryl-amine compound:
Under nitrogen protection system, take by weighing part fluorenyl aromatic amine a 100mmol (25.9g), aryl halide b 110mmol (28.60g) puts into reaction system, adds KOH solid 400mmol (22.4g); The toluene 500ml that adds drying and dehydrating, under nitrogen protection, Catalysts Cu I 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g); Cooling has been reacted in nitrogen protection refluxed reaction 10 hours, and suction filtration concentrates; Methylene dichloride is made solvent, crosses silica gel and does column chromatography, concentrates; Obtain off-white color two amine product 39.51g, productive rate is 90%, and HPLC purity is greater than 98%.Can directly be used as next step reaction.
Synthesizing of step 2, triarylamine compounds (M106):
Take by weighing diaryl-amine compound 50mmol (21.95g), carbazyl halogenide 55mmol (17.66g), potassium tert.-butoxide 75mmol (8.4g) under nitrogen protection, adds catalyst P d (OAC) 222.5mmol (5.04g); Tri-butyl phosphine 27mmol under the nitrogen protection, refluxed cool to room temperature 8 hours; Suction filtration, solution concentration is made solvent with methylene dichloride, crosses silica gel column chromatography; Concentrate, use methylene dichloride, the sherwood oil recrystallization obtains white solid triarylamine compounds 28.90g.Productive rate is 85%.HPLC purity is greater than 98%.
Mass spectrum: calculated value is 680.32; Test value is 680.30.Ultimate analysis: calculated value C:89.96%; H:5.92%; N:4.11%; Test value is: C:89.93%; H:5.90%; N:4.08%.
Embodiment 3 compound M109's is synthetic
Synthesizing of step 1, diaryl-amine compound:
Under nitrogen protection system, take by weighing part fluorenyl aromatic amine a 100mmol (28.5g), aryl halide b 110mmol (25.52g) puts into reaction system, adds KOH solid 400mmol (22.4g); The toluene 500ml that adds drying and dehydrating, under nitrogen protection, Catalysts Cu I 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g); Cooling has been reacted in nitrogen protection refluxed reaction 8 hours, and suction filtration concentrates; Methylene dichloride is made solvent, crosses silica gel and does column chromatography, concentrates; Obtain off-white color two amine product 20.11g, productive rate is 92%, and HPLC purity is greater than 98%.Can directly be used as next step reaction.
Synthesizing of step 2, triarylamine compounds (M109):
Take by weighing diaryl-amine compound 50mmol (21.85g), carbazyl halogenide 55mmol (21.84g), potassium tert.-butoxide 75mmol (8.4g) under nitrogen protection, adds catalyst P d (OAC) 222.5mmol (5.04g); Tri-butyl phosphine 27mmol under the nitrogen protection, refluxed cool to room temperature 6 hours; Suction filtration, solution concentration is made solvent with methylene dichloride, crosses silica gel column chromatography; Concentrate, use methylene dichloride, the sherwood oil recrystallization obtains white solid triarylamine compounds 32.42g.Productive rate is 85%.HPLC purity is greater than 98%.
Mass spectrum: calculated value is 754.33; Test value is 754.30.Ultimate analysis: calculated value C:90.68%; H:5.61%; N:3.71%; Test value is: C:90.66%; H:5.58%; N:3.69%.
Embodiment 4 compound M111's is synthetic
Synthesizing of step 1, diaryl-amine compound:
Under nitrogen protection system, take by weighing part fluorenyl aromatic amine a 100mmol (20.9g), aryl halide b 110mmol (17.16g) puts into reaction system, adds KOH solid 400mmol (22.4g); The toluene 500ml that adds drying and dehydrating, under nitrogen protection, Catalysts Cu I 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g); Cooling has been reacted in nitrogen protection refluxed reaction 6 hours, and suction filtration concentrates; Methylene dichloride is made solvent, crosses silica gel and does column chromatography, concentrates; Obtain off-white color two amine product 26.22g, productive rate is more than 92%, and HPLC purity is greater than 98%.Can directly be used as next step reaction.
Synthesizing of step 2, triarylamine compounds (M111):
Take by weighing diaryl-amine compound 50mmol (14.25g), carbazyl halogenide 55mmol (21.84g), potassium tert.-butoxide 75mmol (8.4g) under nitrogen protection, adds catalyst P d (OAC) 222.5mmol (5.04g); Tri-butyl phosphine 27mmol under the nitrogen protection, refluxed cool to room temperature 5 hours; Suction filtration, solution concentration is made solvent with methylene dichloride, crosses silica gel column chromatography; Concentrate, use methylene dichloride, the sherwood oil recrystallization obtains white solid triarylamine compounds 27.09g.Productive rate is 90%.HPLC purity is greater than 98%.
Mass spectrum: calculated value is 602.27; Test value is 602.25.Ultimate analysis: calculated value C:89.67%; H:5.69%; N:4.65%; Test value is: C:89.66%; H:5.66%; N:4.62%.
Embodiment 5 compound M126's is synthetic
Synthesizing of step 1, diaryl-amine compound:
Under nitrogen protection system, take by weighing part fluorenyl aromatic amine a 100mmol (28.5g), aryl halide b 110mmol (25.52g) puts into reaction system, adds KOH solid 400mmol (22.4g); The toluene 500ml that adds drying and dehydrating, under nitrogen protection, Catalysts Cu I 10mmol (1.9g), 1.10-phenanthroline 20mmol (3.6g); Cooling has been reacted in nitrogen protection refluxed reaction 9 hours, and suction filtration concentrates; Methylene dichloride is made solvent, crosses silica gel and does column chromatography, concentrates; Obtain off-white color two amine product 20.11g, productive rate is 92%, and HPLC purity is greater than 98%.Can directly be used as next step reaction.
Synthesizing of step 2, triarylamine compounds (M126):
Take by weighing diaryl-amine compound 50mmol (21.85g), carbazyl halogenide 55mmol (21.84g), potassium tert.-butoxide 75mmol (8.4g) is under nitrogen protection; Add catalyst P d (OAC) 222.5mmol (5.04g), tri-butyl phosphine 27mmol under the nitrogen protection, refluxed 7 hours; Cool to room temperature, suction filtration, solution concentration is made solvent with methylene dichloride; Cross silica gel column chromatography, concentrate,, obtain white solid triarylamine compounds 26.49g with methylene dichloride, sherwood oil recrystallization.Productive rate is 88%.HPLC purity is greater than 98%.
Mass spectrum: calculated value is 602.27; Test value is 602.25.Ultimate analysis: calculated value C:89.67%; H:5.69%; N:4.65%; Test value is: C:89.65%; H:5.66%; N:4.62%.
The reaction of the compound that all the other are listed is identical with embodiment 1 method for making, and just reaction substrate is different, and concrete structure can be found out through the structure in the tabulation, and the compound of gained characterizes as follows:
Embodiment 6 compound M102:
Mass spectrum: calculated value is 590.27; Test value is 590.25.Ultimate analysis: calculated value C:89.46%; H:5.80%; N:4.74%; Test value is: C:89.44%; H:5.78%; N:4.72%.
Embodiment 7 compound M103
Mass spectrum: calculated value is 666.30; Test value is 666.28.Ultimate analysis: calculated value C:90.06%; H:5.74%; N:4.20%; Test value is: C:90.03%; H:5.71%; N:4.18%.
Embodiment 8 compound M104
Mass spectrum: calculated value is 616.29; Test value is 616.28.Ultimate analysis: calculated value C:89.58%; H:5.88%; N:4.54%; Test value is: C:89.56%; H:5.86%; N:4.42%.
Embodiment 9 compound M105
Mass spectrum: calculated value is 678.30; Test value is 678.28.Ultimate analysis: calculated value C:90.23%; H:5.64%; N:4.13%; Test value is: C:90.20%; H:5.61%; N:4.10%.
Embodiment 10 compound M107
Mass spectrum: calculated value is 652.29; Test value is 652.28.Ultimate analysis: calculated value C:90.15%; H:5.56%; N:4.29%; Test value is: C:90.13%; H:5.54%; N:4.26%.
Embodiment 11 compound M108
Mass spectrum: calculated value is 678.30; Test value is 678.27.Ultimate analysis: calculated value C:90.23%; H:5.64%; N:4.13%; Test value is: C:90.23%; H:5.62%; N:4.10%.
Embodiment 12 compound M110
Mass spectrum: calculated value is 778.33; Test value is 778.30.Ultimate analysis: calculated value C:90.97%; H:5.43%; N:3.60%; Test value is: C:90.95%; H:5.40%; N:3.58%.
Embodiment 13 compound M112
Mass spectrum: calculated value is 652.29; Test value is 652.26.Ultimate analysis: calculated value C:90.15%; H:5.56%; N:4.29%; Test value is: C:90.13%; H:5.54%; N:4.26%.
Embodiment 14 compound M113
Mass spectrum: calculated value is 678.30; Test value is 678.26.Ultimate analysis: calculated value C:90.23%; H:5.64%; N:4.13%; Test value is: C:90.20%; H:5.61%; N:4.10%.
Embodiment 15 compound M114
Mass spectrum: calculated value is 652.29; Test value is 652.26.Ultimate analysis: calculated value C:90.15%; H:5.56%; N:4.29%; Test value is: C:90.13%; H:5.53%; N:4.26%.
Embodiment 16 compound M115
Mass spectrum: calculated value is 666.30; Test value is 666.26.Ultimate analysis: calculated value C:90.06%; H:5.74%; N:4.20%; Test value is: C:90.03%; H:5.71%; N:4.18%.
Embodiment 17 compound M116
Mass spectrum: calculated value is 678.30; Test value is 678.26.Ultimate analysis: calculated value C:90.23%; H:5.64%; N:4.13%; Test value is: C:90.21%; H:5.61%; N:4.10%.
Embodiment 18 compound M117
Mass spectrum: calculated value is 728.32; Test value is 728.30.Ultimate analysis: calculated value C:90.63%; H:5.53%; N:3.84%; Test value is: C:90.60%; H:5.50%; N:3.81%.
Embodiment 19 compound M118
Mass spectrum: calculated value is 754.33; Test value is 754.30.Ultimate analysis: calculated value C:90.68%; H:5.61%; N:3.71%; Test value is: C:90.66%; H:5.58%; N:3.69%.
Embodiment 20 compound M119
Mass spectrum: calculated value is 728.32; Test value is 728.30.Ultimate analysis: calculated value C:90.63%; H:5.53%; N:3.84%; Test value is: C:90.60%; H:5.50%; N:3.81%.
Embodiment 21 compound M120
Mass spectrum: calculated value is 778.33; Test value is 778.30.Ultimate analysis: calculated value C:90.97%; H:5.43%; N:3.60%; Test value is: C:90.95%; H:5.40%; N:3.58%.
Embodiment 22 compound M121
Mass spectrum: calculated value is 804.35; Test value is 804.32.Ultimate analysis: calculated value C:91.01%; H:5.51%; N:3.48%; Test value is: C:90.98%; H:5.49%; N:3.46%.
Embodiment 23 compound M122
Mass spectrum: calculated value is 742.33; Test value is 742.32.Ultimate analysis: calculated value C:90.50%; H:5.70%; N:3.77%; Test value is: C:90.48%; H:5.69%; N:3.76%.
Embodiment 24 compound M123
Mass spectrum: calculated value is 754.33; Test value is 754.32.Ultimate analysis: calculated value C:90.68%; H:5.61%; N:3.71%; Test value is: C:90.66%; H:5.60%; N:3.70%.
Embodiment 25 compound M124
Mass spectrum: calculated value is 854.37; Test value is 854.32.Ultimate analysis: calculated value C:91.30%; H:5.42%; N:3.28%; Test value is: C:91.28%; H:5.40%; N:3.26%.
Embodiment 26 compound M125
Mass spectrum: calculated value is 832.38; Test value is 832.36.Ultimate analysis: calculated value C:90.83%; H:5.81%; N:3.36%; Test value is: C:90.80%; H:5.78%; N:3.33%.
Embodiment 27 compound M127
Mass spectrum: calculated value is 830.37; Test value is 830.36.Ultimate analysis: calculated value C:91.05%; H:5.58%; N:3.37%; Test value is: C:91.02%; H:5.56%; N:3.35%.
Embodiment 28 compound M128
Mass spectrum: calculated value is 756.35; Test value is 756.32.Ultimate analysis: calculated value C:90.44%; H:5.86%; N:3.70%; Test value is: C:90.42%; H:5.83%; N:3.68%.
Embodiment 29 compound M129
Mass spectrum: calculated value is 858.40; Test value is 858.38.Ultimate analysis: calculated value C:90.87%; H:5.87%; N:3.26%; Test value is: C:90.85%; H:5.85%; N:3.24%.
Embodiment 30 compound M130
Mass spectrum: calculated value is 880.38; Test value is 880.36.Ultimate analysis: calculated value C:91.33%; H:5.49%; N:3.18%; Test value is: C:91.30%; H:5.45%; N:3.16%.
Application implementation example 1
With its ito glass substrate that is formed with 1000 thickness in the above, be placed on ultrasonic middle the cleaning 30 minutes of washings, use the zero(ppm) water ultrasonic cleaning then 10 minutes twice.After distilled water wash finishes, distinguish ultrasonic cleaning 30 minutes with Virahol, toluene, acetone, ethanol respectively, dry then.Put into the plasma washing machine at last,, send into vacuum evaporation equipment and process with oxygen plasma cleaning base plate 5 minutes.
NPB, synthetic materials, DBQA, AlQ, LiF, Al are distinguished vapor deposition to device; Form structure devices: [ITO/NPB (20nm)/M101 (30nm): DBQA (2%)/AlQ (20nm)/LiF (5nm)/Al (10nm)]; The velocity of evaporation organism is 1/s; The velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
Test results of devices is cut-in voltage 5v, and high-high brightness is 2800cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.31; Y:0.52 obtains a green color device, and life-span transformation period of device is 1800h.
Application implementation example 2
Application implementation example 2 is identical with making method with the device architecture of application implementation routine 1, and different is with the material of M106 as luminous dopant material, and the device architecture of making is:
[ITO/NPB (20nm)/M106 (30nm): DBQA (2%)/AlQ (20nm)/LiF (5nm)/Al (10nm)]; Velocity of evaporation is that organism is 1/s; The velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
Test results of devices is cut-in voltage 6v, and high-high brightness is 2600cd/m2, and observing efficient under the 10v voltage is 22lm/w, and chromaticity coordinates (CIE) value is x:0.32; Y:0.56 obtains a green color device, and life-span transformation period of device is 2000h.
Application implementation example 3
Application implementation example 3 is identical with making method with the device architecture of application implementation routine 1, and different is with M109 as luminescent material, and the device architecture of making is:
[ITO/NPB (20nm)/M106 (30nm): DBQA (2%)/AlQ (20nm)/LiF (5nm)/Al (10nm)]; Velocity of evaporation is that organism is 1/s; The velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
Test results of devices is cut-in voltage 12v, and high-high brightness is 275000cd/m2, and observing efficient under the 10v voltage is 26lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.58 obtains a green device, and life-span transformation period of device is 2000h.
Application implementation example 4
Application implementation example 4 is identical with making method with the device architecture of application implementation routine 1, and different is with M111 as luminescent material, and the device architecture of making is:
[ITO/NPB (20nm)/M111 (30nm): DBQA (2%)/AlQ (20nm)/LiF (5nm)/Al (10nm)]; Velocity of evaporation is that organism is 1/s; The velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
Test results of devices is cut-in voltage 4.8v, and high-high brightness is 2300cd/m2, and observing efficient under the 10v voltage is 22lm/w, and chromaticity coordinates (CIE) value is x:0.38; Y:0.55 obtains an orange red device, and life-span transformation period of device is 1520h.
Application implementation example 5
Application implementation example 5 is identical with making method with the device architecture of application implementation routine 1, and different is with A26 as luminescent material, and the device architecture of making is:
[ITO/NPB (20nm)/M126 (30nm): DBQA (2%)/AlQ (20nm)/LiF (5nm)/Al (10nm)]; Velocity of evaporation is that organism is 1/s; The velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
Test results of devices is cut-in voltage 4v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.30; Y:0.59 obtains an orange red device, and life-span transformation period of device is 2200h.
The reaction of the compound that all the other are listed is the same with application implementation example 1, and just product is selected different compounds for use, and the device detection of the compound of gained is as follows:
Application implementation example 6 compound M102:
Test results of devices is cut-in voltage 4v, and high-high brightness is 3700cd/m2, and observing efficient under the 10v voltage is 26lm/w, and chromaticity coordinates (CIE) value is x:0.35; Y:0.59 obtains an orange red device, and life-span transformation period of device is 2800h.
Application implementation example 7 compound M103
Test results of devices is cut-in voltage 5v, and high-high brightness is 2900cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.36; Y:0.58 obtains an orange red device, and life-span transformation period of device is 3200h.
Application implementation example 8 compound M104
Test results of devices is cut-in voltage 6v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.58 obtains an orange red device, and life-span transformation period of device is 3200h.
Application implementation example 9 compound M105
Test results of devices is cut-in voltage 4v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3200h.
Application implementation example 10 compound M107
Test results of devices is cut-in voltage 5v, and high-high brightness is 3700cd/m2, and observing efficient under the 10v voltage is 28lm/w, and chromaticity coordinates (CIE) value is x:0.32; Y:0.56 obtains an orange red device, and life-span transformation period of device is 2800h.
Application implementation example 11 compound M108
Test results of devices is cut-in voltage 5v, and high-high brightness is 3500cd/m2, and observing efficient under the 10v voltage is 26lm/w, and chromaticity coordinates (CIE) value is x:0.36; Y:0.55 obtains an orange red device, and life-span transformation period of device is 3500h.
Application implementation example 12 compound M110
Test results of devices is cut-in voltage 4v, and high-high brightness is 3300cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.32; Y:0.56 obtains an orange red device, and life-span transformation period of device is 4200h.
Application implementation example 13 compound M112
Test results of devices is cut-in voltage 5v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 2800h.
Application implementation example 14 compound M113
Test results of devices is cut-in voltage 5v, and high-high brightness is 3700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.35; Y:0.55 obtains an orange red device, and life-span transformation period of device is 2800h.
Application implementation example 15 compound M114
Test results of devices is cut-in voltage 5v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.55 obtains an orange red device, and life-span transformation period of device is 3800h.
Application implementation example 16 compound M115
Test results of devices is cut-in voltage 5v, and high-high brightness is 2500cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3200h.
Application implementation example 17 compound M116
Test results of devices is cut-in voltage 5v, and high-high brightness is 2600cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.35; Y:0.55 obtains an orange red device, and life-span transformation period of device is 3000h.
Application implementation example 18 compound M117
Test results of devices is cut-in voltage 5v, and high-high brightness is 3200cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.35; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3300h.
Application implementation example 19 compound M118
Test results of devices is cut-in voltage 5v, and high-high brightness is 3300cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3800h.
Application implementation example 20 compound M119
Test results of devices is cut-in voltage 5v, and high-high brightness is 3300cd/m2, and observing efficient under the 10v voltage is 28lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3800h.
Application implementation example 21 compound M120
Test results of devices is cut-in voltage 5v, and high-high brightness is 3700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3500h.
Application implementation example 22 compound M121
Test results of devices is cut-in voltage 5v, and high-high brightness is 3200cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.36; Y:0.55 obtains an orange red device, and life-span transformation period of device is 3200h.
Application implementation example 23 compound M122
Test results of devices is cut-in voltage 5v, and high-high brightness is 2800cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3300h.
Application implementation example 24 compound M123
Test results of devices is cut-in voltage 5v, and high-high brightness is 3300cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3500h.
Application implementation example 25 compound M124
Test results of devices is cut-in voltage 5v, and high-high brightness is 2800cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3800h.
Application implementation example 26 compound M125
Test results of devices is cut-in voltage 5v, and high-high brightness is 3600cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 2800h.
Application implementation example 27 compound M127
Test results of devices is cut-in voltage 5v, and high-high brightness is 3200cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3800h.
Application implementation example 28 compound M128
Test results of devices is cut-in voltage 5v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.36; Y:0.56 obtains an orange red device, and life-span transformation period of device is 4200h.
Application implementation example 29 compound M129
Test results of devices is cut-in voltage 5v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3200h.
Application implementation example 30 compound M130
Test results of devices is cut-in voltage 5v, and high-high brightness is 2700cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.33; Y:0.56 obtains an orange red device, and life-span transformation period of device is 3300h.
List the luminosity factor of the compound of embodiment 1-5 below
The luminosity factor of gained compound among table 1 embodiment
| ? | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 |
| The luminous efficiency of dilute solution | 96% | 97% | 99% | 95% | 98% |
| The luminous efficiency of solid film | 55% | 58% | 60% | 62% | 68% |
Can find out that from the data of table 1 electroluminescent organic material of three arylamine structures among the embodiment has high luminous efficiency, high luminous efficiency shows that this compound can be used as luminescent material or luminous material of main part and transport material and is applied in the electroluminescent device.Simultaneously according to application implementation example 1-30; Material is applied in the organic electroluminescence device; Through data test and comparison; Finding that this type material is reasonable luminous material of main part of the electroluminescent organic material of excellent property, particularly performance and transport material, is very promising one type of electroluminescent organic material.
Should be understood that application of the present invention is not limited to above-mentioned giving an example, concerning those of ordinary skills, can improve or conversion that all these improvement and conversion all should belong to the protection domain of accompanying claims of the present invention according to above-mentioned explanation.
Claims (6)
1. electroluminescent organic material that contains three arylamine structures, it is characterized in that: general structure is suc as formula shown in (1):
Wherein, it is 0 or 1 that n1, n2, n3 independently represent the number of phenyl ring respectively, and the A group is represented the substituted carbazole group, and concrete structure is following:
The representative of B group contains the building stone that replaces fluorenyl, and concrete structure is following:
C-structure is the building stone that contains phenyl and substituted-phenyl, and concrete structure is following:
2. the electroluminescent organic material that contains three arylamine structures according to claim 1 is characterized in that: electroluminescent organic material is any one in the represented compound of structural formula M101-M130:
3. according to claim 1, the 2 described preparing methods that contain the electroluminescent organic material of three arylamine structures, it is characterized in that:
Synthesizing of step 1, diaryl-amine compound
Under nitrogen protection system, take by weighing part fluorenyl aromatic amine a 100mmol, aryl halide b 110mmol puts into reaction system, adds KOH solid 400mmol (22.4g), adds the toluene 500ml of drying and dehydrating; Under nitrogen protection, Catalysts Cu I 10mmol, 1.10-phenanthroline 20mmol, nitrogen protection refluxed reaction 5-10 hour; Reacted cooling, suction filtration concentrates, and methylene dichloride is made solvent; Cross silica gel and do column chromatography, concentrate, obtain off-white color two amine products, subsequent use;
Synthesizing of step 2, triarylamine compounds
Take by weighing diaryl-amine compound 50mmol, carbazyl halogenide 55mmol, potassium tert.-butoxide 75mmol (8.4g) under nitrogen protection, adds catalyst P d (OAC)
222.5mmol, tri-butyl phosphine 27mmol, under the nitrogen protection, backflow 4-8 hour, cool to room temperature, suction filtration, solution concentration is made solvent with methylene dichloride, crosses silica gel column chromatography, concentrates, and uses methylene dichloride, and the sherwood oil recrystallization obtains the white solid triarylamine compounds.
4. the application that contains the electroluminescent organic material of three arylamine structures according to claim 1 is characterized in that: between the positive and negative electrode on the organic electronic devices, have at least one deck organic material layer to comprise any one compound according to claim 1.
5. the application that contains the electroluminescent organic material of three arylamine structures according to claim 4 is characterized in that: organic electronic devices comprises organic luminescent device, solar cell device, organic semiconductor device, organic crystal tube device.
6. the application that contains the electroluminescent organic material of three arylamine structures according to claim 4; It is characterized in that: organic material layer comprises luminescent material, hole mobile material, electron transport material, hole-injecting material, electronics injecting material, hole barrier materials, electronics blocking material, and organic material layer comprises the described organic materials of one or more claims 1.
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