CN102532105A - Triphenylene compound containing pyridine group and application thereof - Google Patents

Triphenylene compound containing pyridine group and application thereof Download PDF

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CN102532105A
CN102532105A CN2010106111777A CN201010611177A CN102532105A CN 102532105 A CN102532105 A CN 102532105A CN 2010106111777 A CN2010106111777 A CN 2010106111777A CN 201010611177 A CN201010611177 A CN 201010611177A CN 102532105 A CN102532105 A CN 102532105A
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reaction
warp
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raw material
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邱勇
孙绪霞
李银奎
段炼
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Tsinghua University
Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
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Tsinghua University
Beijing Visionox Technology Co Ltd
Kunshan Visionox Display Co Ltd
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Abstract

The invention provides a novel compound, which has stable compound property, a simple preparation process, high luminous efficiency and high carrier mobility and can be applied to a phosphorescent main body material and an electron transfer layer of an electroluminescent element. According to an applied device, the driving voltage can be reduced remarkably, and the current efficiency is increased. The structural general formula of the compound is shown as a formula I, wherein a mother nucleus is selected from triphenylene; terminal groups Ar1, Ar2 and Ar3 are selected from a pyridine group, a phenyl group, a biphenylyl group or a naphthyl group; A, B and C are chemical bonds or aromatic rings with 6-30 carbon atoms; and m, n and p are integers of 0-2.

Description

A kind of triphenylene compounds and application thereof that contains the pyridine group
Technical field
The present invention relates to a kind of novel organic materials, and the application in the ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
Phosphorescent coloring can not need be entrained in it in suitable material of main part separately as the luminescent layer of OLED usually, forms the Subjective and Objective luminescent layer.In order to realize effective transmission ofenergy, require the triplet E of material of main part usually TThe triplet E that is higher than dye molecule TFor redness or green phosphorescent dye, material of main part CBP (structure is shown in the following figure) performance commonly used at present is original.But for the blue phosphorescent dyestuff, the triplet energy state of itself is higher, and the material of main part of seeking the higher triplet energy state that is complementary with it is just comparatively difficult.Blue phosphorescent dyestuff FIrpic with commonly used at present is an example, and its triplet is 2.65eV, and the triplet of material of main part CBP commonly used is 2.56eV, thereby the energy transfer process between from CBP to FIrpic is an endothermic process.Discover that for the phosphorescence Subjective and Objective system of heat absorption transmission ofenergy, device prepares in the process as introduced micro-water oxygen contamination and will cause device efficiency to reduce greatly; And when temperature reduces, the heat absorption energy transfer process will be restrained.Simultaneously, because a large amount of triplet excitons are present in the main body and can not energy be in time passed to phosphorescent coloring, this also is to cause one of of short duration reason blue phosphorescent device lifetime.Therefore, the material of main part of seeking high triplet energy state becomes one of main path that solves blue phosphorescent device lifetime and efficiency.
Since 2003; People are through reducing the molecular conjugation degree; The material of main part that (structure are shown below) such as mCP, UGH, CDBP, SimCP has high triplet energy state (2.7-3.2eV) has been synthesized in design, for the CBP material of main part, has improved the efficient of blue phosphorescent device greatly.In the work in early stage; We study and have reported the TBCPF series blue phosphorescent material of main part TBCPF based on carbazole/fluorenyl; High triplet and high stability with 2.84ev; Realized also that particularly wet method prepares the high efficiency blue phosphorescent device of small molecules individual layer (Tetrahedron, 63 (2007): 10161-10168).The aforementioned body material is the material of main part that contains the inclined to one side hole transport ability of carbazole group mostly.We develop the material of main part with inclined to one side electronic transmission performance again at this.
Figure BSA00000402025600011
Summary of the invention
The objective of the invention is to propose a kind of novel cpd, this compounds can be used for the ORGANIC ELECTROLUMINESCENCE DISPLAYS field.
Triphenylene group triplet is than higher (2.86ev); And the pyridine group is a strong electron-withdrawing group group; Have the good electron transmission performance, its introducing can significantly not reduce the triplet of whole molecule, thereby the triplet that guarantees this type of material is enough high.Triphenylene group and pyridine group are combined; Both satisfied the particularly requirement of the higher triplet of blue phosphorescent main body needs of phosphorescent light body material; Because molecule has certain conjugated system, high electronics flowability can be provided on the other hand, link to each other with electrophilic pyridine group; Can increase its electronic mobility, improve the material electronics transmission performance.Compound of the present invention has higher electronic transmission performance, and good film-forming property at room temperature has advantages of higher stability, and applied device at room temperature also has advantages of higher stability.In organic electroluminescent device, not only can be used as phosphorescent light body material, also can be used as electron transport material.
The present invention discloses one type of novel cpd, and its general structure is as follows:
Figure BSA00000402025600022
Wherein Ar1, Ar2, Ar3 are selected from pyridine group, phenyl group, xenyl group or naphthyl group, and A, B, C are the aromatic ring of chemical bond or carbonatoms 6-30, and m, n, p are the integer of 0-2.
The concrete structure of Ar1 among the following formula I, Ar2, Ar3 is selected from following formula:
Figure BSA00000402025600031
In order more to clearly demonstrate content of the present invention, the structure of the compound that following mask body narration the present invention relates to:
Figure BSA00000402025600032
Figure BSA00000402025600041
Figure BSA00000402025600051
Figure BSA00000402025600061
Figure BSA00000402025600071
Figure BSA00000402025600081
Figure BSA00000402025600091
Figure BSA00000402025600111
Figure BSA00000402025600131
Figure BSA00000402025600141
Figure BSA00000402025600151
Figure BSA00000402025600161
Figure BSA00000402025600171
Figure BSA00000402025600201
Figure BSA00000402025600211
Organic materials of the present invention is used as phosphorescence main body or electron transfer layer in organic electroluminescence device.
The present invention also proposes a kind of organic electroluminescence device, comprises above-mentioned general formula compound in its organic function layer, and this compounds is as phosphorescent light body material or electron transport material in the organic function layer.
Embodiment
Among the present invention used industrial chemicals such as haloperidid, phenylo boric acid, pyridine boric acid, naphthalene boronic acids, biphenyl boric acid and bromo triphenylene all at home Chemicals market bought, various substituted pyridine boric acid or all available common organic method of substituted phenylo boric acid are synthetic.
Embodiment
In the present invention the compound process mainly through halides and boric acid compound carry out linked reaction (Journal of Organometallic Chenistry1999,576,147-168).Wherein the boronic acid compounds preparation that is see document (Organic Syntheses2005, Vol.81, p.89) the concrete elaboration as follows:
The preparation of embodiment 1 compound 1-1
(1) preparation of the substituted pyridine boric acid of aryl:
Figure BSA00000402025600212
23.5g (0.10mmol) 2,6-dibromo pyridine, 12.0g phenylo boric acid and 0.50g Pd (PPh 3) 4Be dissolved in the 300.0mL toluene, 22.0g salt of wormwood is dissolved in the 100.0mL water adds in the above reaction solution, 50 ℃ of reaction solutions become yellow immediately.Along with reaction is carried out, the reaction solution color is thin out gradually, behind the 1.5h, adds the 2.50g phenylo boric acid, TLC monitoring reaction process.About 0.5h afterreaction finishes, with three anhydrous Na of organic layer washing 2SO 4Carry out column chromatography after the drying, eluent is a sherwood oil: dichloro=20: 1 (V 1/ V 2) must near-white solid 15.1g.MS (m/e): 234, fusing point 47-49 °, productive rate 64.3%.Products obtained therefrom is dissolved in 200.0mL exsiccant THF, adds 16.0 gram triisopropyl borate esters again and be cooled to-40 ℃ of dropping 34.0mL butyllithiums (2.5M), controlled temperature stirs 30min at-40 ℃ between-50 ℃, be warming up to-20 ℃ naturally; The hydrochloric acid soln that adds 100.0mL1.5M is hydrolyzed, separatory, and water layer transfers pH to neutral with 10% sodium carbonate solution; It is saturated to add 40.0g sodium-chlor again, extracts with ETHYLE ACETATE 40.0mL * 3, merges organic layer; Use dried over mgso 30min, the elimination siccative is evaporated to dried; Obtain white solid 10.8 grams, MS (m/e): 199, productive rate 84.4%.
(2) preparation of target molecule:
Figure BSA00000402025600221
4.62g (0.01mol) 2,6,10-tribromo triphenylene and 7.5g (0.038mol) 6-phenyl-pyridine-2-boric acid is dissolved in the mixing solutions of 200.0mL YLENE, 100mL ethanol and 100mL water, adds 8.3g salt of wormwood and 1.2g Pd (PPh 3) 4, refluxing, reaction solution becomes yellow, behind the reaction 2h, adds 2.0g 6-phenyl-pyridine-2-boric acid.The TLC detection reaction finishes, and cooling has been left standstill a large amount of solids and separated out, with its washing three times.Boil twice with THF again.Get pale yellow powder 4.72g at last, be compound 1-1.MS (m/e): 687, ultimate analysis (C 51H 33N 3): theoretical value C:89.06%, H:4.84%, N:6.11%; Measured value C:89.12%, H:4.77%, N:6.11%.Productive rate 68.7%.
The preparation route of embodiment 2-30 is specifically set forth as follows with embodiment 1 at present:
Embodiment 2 compound 1-2's is synthetic
Selecting 2-chloro-4-iodine pyridine and phenylo boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-2.MS (m/e): 687, ultimate analysis (C 51H 33N 3): theoretical value C:89.06%, H:4.84%, N:6.11%; Measured value C:89.10%, H:4.71%, N:6.19%.Productive rate 62.4%.
Embodiment 3 compound 1-3's is synthetic
Select 3 for use, 5-dibromo pyridine and phenylo boric acid are raw material, the reaction that warp and embodiment 1 are identical, compound 1-3.MS (m/e): 687, ultimate analysis (C 51H 33N 3): theoretical value C:89.06%, H:4.84%, N:6.11%; Measured value C:89.15%, H:4.81%, N:6.04%.Productive rate 58.8%.
Embodiment 4 compound 1-4's is synthetic
Selecting 2-iodo-4-bromopyridine and phenylo boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-4.MS (m/e): 687, ultimate analysis (C 51H 33N 3): theoretical value C:89.06%, H:4.84%, N:6.11%; Measured value C:89.01%, H:4.96%, N:6.03%.Productive rate 61.4%.
Embodiment 5 compound 1-5's is synthetic
Selecting 2-bromo-5-iodine pyridine and phenylo boric acid for use is raw material, and the reaction that warp and embodiment 1 are identical obtains compound 1-5.MS (m/e): 687, ultimate analysis (C 51H 33N 3): theoretical value C:89.06%, H:4.84%, N:6.11%; Measured value C:89.01%, H:4.93%, N:6.06%.Productive rate 62.3%.
Embodiment 6 compound 1-6's is synthetic
Selecting 2-iodo-5-bromopyridine and phenylo boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-6.MS (m/e): 687, ultimate analysis (C 51H 33N 3): theoretical value C:89.06%, H:4.84%, N:6.11%; Measured value C:88.97%, H:4.91%, N:6.12%.Productive rate 59.5%.
Embodiment 7 compound 1-7's is synthetic
Select 2 for use, 6-dibromo pyridine and 3-biphenyl boric acid are raw material, the reaction that warp and embodiment 1 are identical, compound 1-7.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.37%, H:4.93%, N:5.70%.Productive rate 64.2%.
Embodiment 8 compound 1-8's is synthetic
Selecting 2-chloro-4-iodine pyridine and 3-biphenyl boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-8.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.29%, H:5.05%, N:4.66%.Productive rate 60.6%.
Embodiment 9 compound 1-9's is synthetic
Select 3 for use, 5-dibromo pyridine and 3-biphenyl boric acid are raw material, the reaction that warp and embodiment 1 are identical, compound 1-9.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.42%, H:5.03%, N:4.55%.Productive rate 56.8%.
Embodiment 10 compound 1-10's is synthetic
Selecting 2-iodo-4-bromopyridine and 3-biphenyl boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-10.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.35%, H:4.98%, N:4.67%.Productive rate 61.4%.
Embodiment 11 compound 1-11's is synthetic
Selecting 2-bromo-5-iodine pyridine and 3-biphenyl boric acid for use is raw material, and the reaction that warp and embodiment 1 are identical obtains compound 1-11.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.40%, H:5.03%, N:4.57%.Productive rate 62.7%.
Embodiment 12 compound 1-12's is synthetic
Selecting 2-iodo-5-bromopyridine and 3-biphenyl boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-12.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.57%, H:5.03%, N:4.40%.Productive rate 60.8%.
Embodiment 13 compound 1-13's is synthetic
Select 3 for use, 5-dibromo pyridine and 4-biphenyl boric acid are raw material, the reaction that warp and embodiment 1 are identical, compound 1-13.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.52%, H:4.91%, N:4.57%.Productive rate 62.4%.
Embodiment 14 compound 1-14's is synthetic
Selecting 2-iodo-4-bromopyridine and 4-biphenyl boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-14.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.39%, H:5.07%, N:4.54%.Productive rate 61.2%.
Embodiment 15 compound 1-15's is synthetic
Select 3 for use, 5-dibromo pyridine and 4-biphenyl boric acid are raw material, the reaction that warp and embodiment 1 are identical, compound 1-15.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.42%, H:5.03%, N:4.55%.Productive rate 56.8%.
Embodiment 16 compound 1-16's is synthetic
Selecting 2-iodo-4-bromopyridine and 4-biphenyl boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-16.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.35%, H:4.98%, N:4.67%.Productive rate 61.4%.。
Embodiment 17 compound 1-17's is synthetic
Selecting 2-bromo-5-iodine pyridine and 4-biphenyl boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-17.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.40%, H:5.03%, N:4.57%.Productive rate 62.7%.
Embodiment 18 compound 1-18's is synthetic
Selecting 2-iodo-5-bromopyridine and 4-biphenyl boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-18.MS (m/e): 915, ultimate analysis (C 69H 45N 3): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.57%, H:5.03%, N:4.40%.Productive rate 60.8%.
Embodiment 19 compound 1-19's is synthetic
Select 2 for use, 6-dibromo pyridine and 1-naphthalene boronic acids are raw material, the reaction that warp and embodiment 1 are identical, compound 1-19.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.38%, H:4.71%, N:4.91%.Productive rate 58.3%.
Embodiment 20 compound 1-20's is synthetic
Selecting 2-chloro-4-iodine pyridine and 1-naphthalene boronic acids for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-20.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.14%, H:4.70%, N:5.16%.Productive rate 57.8%.
Embodiment 21 compound 1-21's is synthetic
Select 3 for use, 5-dibromo pyridine and 1-naphthalene boronic acids are raw material, the reaction that warp and embodiment 1 are identical, compound 1-21.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.21%, H:4.80%, N:4.99%.Productive rate 58.7%.
Embodiment 22 compound 1-22's is synthetic
Selecting 2-chloro-4-iodine pyridine and 1-naphthalene boronic acids for use is raw material, 1 reaction that warp and embodiment 1 are identical, compound 1-22.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.22%, H:4.77%, N:5.01%.Productive rate 60.8%.
Embodiment 23 compound 1-23's is synthetic
Selecting 2-bromo-5-iodine pyridine and 1-naphthalene boronic acids for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-23.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.40%, H:4.63%, N:4.97%.Productive rate 61.4%.
Embodiment 24 compound 1-24's is synthetic
Selecting 2-iodo-5-bromopyridine and 1-naphthalene boronic acids for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-24.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.21%, H:4.83%, N:4.96%.Productive rate 58.8%.
Embodiment 25 compound 1-25's is synthetic
Select 2 for use, 6-dibromo pyridine and 2-naphthalene phenylo boric acid are raw material, the reaction that warp and embodiment 1 are identical, compound 1-25.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.18%, H:4.68%, N:5.14%.Productive rate 60.1%.
Embodiment 26 compound 1-26's is synthetic
Selecting 2-chloro-4-iodine pyridine and 2-naphthalene boronic acids for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-26.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.13%, H:4.77%, N:5.10%.Productive rate 62.3%.
Embodiment 27 compound 1-27's is synthetic
Select 3 for use, 5-dibromo pyridine and 2-naphthalene boronic acids are raw material, the reaction that warp and embodiment 1 are identical, compound 1-27.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.30%, H:4.71%, N:4.99%.Productive rate 59.1%.
Embodiment 28 compound 1-28's is synthetic
Selecting 2-chloro-4-iodine pyridine and 2-naphthalene boronic acids for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-28.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.28%, H:4.65%, N:5.07%.Productive rate 61.3%.
Embodiment 29 compound 1-29's is synthetic
Selecting 2-bromo-5-iodine pyridine and 2-naphthalene boronic acids for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-29.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.40%, H:4.63%, N:4.97%.Productive rate 59.7%.
Embodiment 30 compound 1-30's is synthetic
Selecting 2-iodo-5-bromopyridine and 2-naphthalene boronic acids for use is raw material, the reaction that warp and embodiment 1 are identical, compound 1-30.MS (m/e): 837, ultimate analysis (C 63H 39N 3): theoretical value C:90.29%, H:4.69%, N:5.01%; Measured value C:90.21%, H:4.83%, N:4.96%.Productive rate 57.4%
Embodiment 31 compound 2-1's is synthetic
Select 2 for use, 7-dibromo triphenylene and 6-phenyl-2-pyridine boric acid is raw material, the control feed ratio, the reaction that warp and embodiment 1 are identical, compound 2-1.MS (m/e): 534, ultimate analysis (C 40H 26N 2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.82%, H:4.91%, N:5.27%.Productive rate 59.1%.
Embodiment 32 compound 2-2's is synthetic
Figure BSA00000402025600261
At first 2,7-dibromo triphenylene and 6-phenyl-2-pyridine boric acid is raw material, makes midbody M, M and 4-phenyl-2-pyridine boric acid coupling, compound 2-2.MS (m/e): 534, ultimate analysis (C 40H 26N 2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.90%, H:4.81%, N:5.29%.Productive rate 62.3%.
Embodiment 33-60 and embodiment 32 are similar, select suitable reaction substrate, and the control ingredient proportion carries out twice coupling and promptly gets title product.Existing concrete the elaboration as follows:
Embodiment 33 compound 2-3's is synthetic
Selecting midbody M and 5-phenyl-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-3.MS (m/e): 534, ultimate analysis (C 40H 26N 2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.80%, H:4.97%, N:5.23%.Productive rate 46.2%.
Embodiment 34 compound 2-4's is synthetic
Selecting midbody M and 2-phenyl-4-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-4.MS (m/e): 534, ultimate analysis (C 40H 26N 2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.97%, H:4.92%, N:5.11%.Productive rate 40.8%.
Embodiment 35 compound 2-5's is synthetic
Selecting midbody M and 5-phenyl-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-5.MS (m/e): 534, ultimate analysis (C 40H 26N 2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.82%, H:4.93%, N:5.25%.Productive rate 38.6%.
Embodiment 36 compound 2-6's is synthetic
Selecting midbody M and 6-phenyl-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-6.MS (m/e): 534, ultimate analysis (C 40H 26N 2): theoretical value C:89.86%, H:4.90%, N:5.24%; Measured value C:89.79%, H:5.01%, N:5.20%.Productive rate 41.3%.
Embodiment 37 compound 2-7's is synthetic
Selecting midbody M and 6-(3-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-7.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.42%, H:4.91%, N:4.67%.Productive rate 42.1%.
Embodiment 38 compound 2-8's is synthetic
Selecting midbody M and 4-(3-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-8.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.38%, H:5.47%, N:4.65%.Productive rate 41.6%.
Embodiment 39 compound 2-9's is synthetic
Selecting midbody M and 5-(3-biphenyl)-3-pyridine boric acid for use is raw material, and the reaction that warp and embodiment 32 are identical obtains compound 2-9.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.54%, H:5.02%, N:4.44%.Productive rate 46.3%.
Embodiment 40 compound 2-10's is synthetic
Identical reaction that to select midbody M and 2-(3-biphenyl)-4-pyridine boric acid for use be the raw material warp with embodiment 32, compound 2-10.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.41%, H:5.02%, N:4.57%.Productive rate 40.6%.
Embodiment 41 compound 2-11's is synthetic
Selecting midbody M and 5-(3-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-11.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.52%, H:5.06%, N:4.42%.Productive rate 41.3%.
Embodiment 42 compound 2-12's is synthetic
Selecting midbody M and 6-(3-biphenyl)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-12.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.51%, H:4.97%, N:4.42%.Productive rate 43.2%.
Embodiment 43 compound 2-13's is synthetic
Selecting midbody M and 6-(4-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-13.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.42%, H:5.11%, N:4.47%.Productive rate 45.7%.
Embodiment 44 compound 2-14's is synthetic
Selecting midbody M and 4-(4-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-14.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.55%, H:4.89%, N:4.56%.Productive rate 41.4%.
Embodiment 45 compound 2-15's is synthetic
Selecting midbody M and 5-(4-biphenyl)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-15.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.56%, H:5.03%, N:4.48%.Productive rate 38.8%.
Embodiment 46 compound 2-16's is synthetic
Selecting midbody M and 2-(4-biphenyl)-4-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-16.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.41%, H:4.97%, N:4.62%.Productive rate 41.6%.
Embodiment 47 compound 2-17's is synthetic
Selecting midbody M and 5-(4-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-17.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.50%, H:5.05%, N:4.45%.Productive rate 41.3%.
Embodiment 48 compound 2-18's is synthetic
Selecting midbody M and 6-(4-biphenyl)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-18.Product MS (m/e): 610, ultimate analysis (C 46H 30N 2): theoretical value C:90.46%, H:4.95%, N:4.59%; Measured value C:90.39%, H:5.08%, N:4.53%.Productive rate 42.3%
Embodiment 49 compound 2-19's is synthetic
Selecting midbody M and 6-(1-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-19.MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.25%, H:4.87%, N:4.88%.Productive rate 43.8%.
Embodiment 50 compound 2-20's is synthetic
Selecting midbody M and 4-(1-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-20.MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.32%, H:4.88%, N:4.80%.Productive rate 41.7%.
Embodiment 51 compound 2-21's is synthetic
Selecting midbody M and 5-(1-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-21.MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.29%, H:4.98%, N:4.73%.Productive rate 38.9%.
Embodiment 52 compound 2-22's is synthetic
Selecting midbody M and 2-(1-naphthalene)-4-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-22.MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.43%, H:4.84%, N:4.73%.Productive rate 40.8%.
Embodiment 53 compound 2-23's is synthetic
With midbody M and 5-(1-naphthalene)-2-pyridine boric acid is raw material, the reaction that warp and embodiment 32 are identical, compound 2-23.MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:92.35%, H:4.97%, N:4.68%.Productive rate 42.4%.
Embodiment 54 compound 2-24's is synthetic
Selecting midbody M and 6-(1-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-24.MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.34%, H:4.90%, N:4.76%.Productive rate 41.9%.
Embodiment 55 compound 2-25's is synthetic
Selecting midbody M and 6-(2-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-25.Product MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.27%, H:4.92%, N:4.81%.Productive rate 40.7%.
Embodiment 56 compound 2-26's is synthetic
Selecting midbody M and 6-(2-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-26.Product MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.24%, H:4.98%, N:4.78%.Productive rate 40.3%.
Embodiment 57 compound 2-27's is synthetic
Selecting midbody M and 5-(2-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-27.Product MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.25%, H:4.90%, N:4.84%.Productive rate 41.5%.
Embodiment 58 compound 2-28's is synthetic
Selecting midbody M and 6-(2-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-28.Product MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.24%, H:4.91%, N:4.85%.Productive rate 40.8%.
Embodiment 59 compound 2-29's is synthetic
Selecting midbody M and 5-(2-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-29.Product MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.37%, H:4.82%, N:4.81%.Productive rate 40.7%.
Embodiment 60 compound 2-30's is synthetic
Selecting midbody M and 6-(2-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 2-30.Product MS (m/e): 584, ultimate analysis (C 44H 28N 2): theoretical value C:90.38%, H:4.83%, N:4.79%; Measured value C:90.35%, H:4.92%, N:4.73%.Productive rate 41.4%.
Embodiment 61 compound 3-1's is synthetic
Midbody K prepares route and is shown in the following figure:
Figure BSA00000402025600311
Selecting midbody K and 6-phenyl-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 1 are identical, compound 3-1.Product MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.24%, H:4.72%, N:8.04%.Productive rate 41.4%.Wherein the preparation of Compound C as follows (Org.Lett.2007., Vol.9, No.4,559-562, NewJ.Chem.2001,25,1136-1147):.
Figure BSA00000402025600312
18.5g (0.1mol) p-bromobenzaldehyde and 24.2g (0.20mol) 2-acetylpyridine is dissolved in the 640mL methyl alcohol, in this solution, adds 4.0g (0.10mol) NaOH, reaction solution is faint yellow, adds the ammoniacal liquor of 160mL 25% again.Reflux, solution colour is gradually dark, from faint yellow-yellow-green colour-pale brown look-brown.There are a large amount of solids to separate out, refluxed 2.5 days.The HPLC monitoring reaction leaves standstill cooling, and with the solid suction filtration, it is closely colourless that water, methyl alcohol are repeatedly washed solid to washing lotion, uses ethyl alcohol recrystallization, gets white needle-like crystals A 14.7g, 159.5 ℃ of fusing points, and MS (m/e): 387, productive rate 38.4%.With Pd (dPPf) Cl 2Catalyzer 0.30g (0.03equiv) Potassium ethanoate 3.53g (36mml, 3equiv) and two neopentyl alcohol boric acid ester 2.85g (12.6mmol 1.05equiv) is dissolved among the 120mL exsiccant DMSO, and nitrogen protection adds down 4-bromo-2; 2 ': 6 ', 2 "-and terpyridyl 4.66g (12mmol), 80 ℃ are stirred 5.5h, finish to add toluene 100mL; add washing repeatedly again, organic layer is used dried over mgso, revolves dried; use recrystallizing methanol, gets white crystal B 3.13g, productive rate 61.9%.It is dissolved in the 30mL trifluoroacetic acid, adds 1.0g KOH, stirring at room 20min adds 20mL water again, has a large amount of solids to separate out, and filters, and uses ethyl alcohol recrystallization, gets white solid C 2.17g, productive rate 83.1%.
Embodiment 62 compound 3-2's is synthetic
Selecting midbody K and 4-phenyl-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-2.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.10%, H:4.77%, N:8.23%.Productive rate 46.2%.
Embodiment 63 compound 3-3's is synthetic
Selecting midbody K and 5-phenyl-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-3.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.14%, H:4.67%, N:8.19%.Productive rate 43.7%.
Embodiment 64 compound 3-4's is synthetic
Selecting midbody K and 2-phenyl-4-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-4.MS (m/e) 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:89.25%, H:4.72%, N:8.03%.Productive rate 42.8%.
Embodiment 65 compound 3-5's is synthetic
Selecting midbody K and 5-phenyl-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-5.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.22%, H:4.73%, N:8.05%.Productive rate 39.6%.
Embodiment 66 compound 3-6's is synthetic
Selecting midbody K and 6-phenyl-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-6.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.09%, H:4.71%, N:8.20%.Productive rate 42.8%.
Embodiment 67 compound 3-7's is synthetic
Selecting midbody K and 6-(3-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-7.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.92%, H:4.81%, N:7.27%.Productive rate 44.6%.
Embodiment 68 compound 3-8's is synthetic
Selecting midbody K and 4-(3-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-8.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.88%, H:4.77%, N:7.35%.Productive rate 41.6%.
Embodiment 69 compound 3-9's is synthetic
Selecting midbody K and 5-(3-biphenyl)-3-pyridine boric acid for use is raw material, and the reaction that warp and embodiment 32 are identical obtains compound 3-9.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.84%, H:4.72%, N:7.44%.Productive rate 46.3%.
Embodiment 70 compound 3-10's is synthetic
Identical reaction that to select midbody K and 2-(3-biphenyl)-4-pyridine boric acid for use be the raw material warp with embodiment 32, compound 3-10.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.91%, H:4.82%, N:7.27%.Productive rate 42.6%.
Embodiment 71 compound 3-11's is synthetic
Selecting midbody K and 5-(3-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-11.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.82%, H:4.76%, N:7.42%.Productive rate 41.3%.
Embodiment 72 compound 3-12's is synthetic
Selecting midbody K and 6-(3-biphenyl)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-12.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.85%, H:4.67%, N:7.48%.Productive rate 43.2%.
Embodiment 73 compound 3-13's is synthetic
Selecting midbody K and 6-(4-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-13.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:88.02%, H:4.71%, N:7.27%.Productive rate 44.7%.
Embodiment 74 compound 3-14's is synthetic
Selecting midbody K and 4-(4-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-14.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.85%, H:4.82%, N:7.33%.Productive rate 42.5%.
Embodiment 75 compound 3-15's is synthetic
Selecting midbody K and 5-(4-biphenyl)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-15.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.86%, H:4.83%, N:7.31%.Productive rate 39.8%.
Embodiment 76 compound 3-16's is synthetic
Selecting midbody K and 2-(4-biphenyl)-4-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-16.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:88.04%, H:4.77%, N:7.19%.Productive rate 42.4%.
Embodiment 77 compound 3-17's is synthetic
Selecting midbody K and 5-(4-biphenyl)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-17.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:87.90%, H:4.85%, N:7.25%.Productive rate 41.9%.
Embodiment 78 compound 3-18's is synthetic
Selecting midbody K and 6-(4-biphenyl)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-18.Product MS (m/e): 764, ultimate analysis (C 56H 36N 4): theoretical value C:87.93%, H:4.74%, N:7.32%; Measured value C:88.04%, H:4.68%, N:7.28%.Productive rate 42.3%
Embodiment 79 compound 3-19's is synthetic
Selecting midbody K and 6-(1-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-19.MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.85%, H:4.77%, N:7.38%.Productive rate 42.7%.
Embodiment 80 compound 3-20's is synthetic
Selecting midbody K and 4-(1-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-20.MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.82%, H:4.68%, N:7.50%.Productive rate 44.7%.
Embodiment 81 compound 3-21's is synthetic
Selecting midbody K and 5-(1-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-21.MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.86%, H:4.68%, N:7.46%.Productive rate 41.9%.
Embodiment 82 compound 3-22's is synthetic
Selecting midbody K and 2-(1-naphthalene)-4-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-22.MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.83%, H:4.74%, N:7.43%.Productive rate 40.8%.
Embodiment 83 compound 3-23's is synthetic
With midbody K and 5-(1-naphthalene)-2-pyridine boric acid is raw material, the reaction that warp and embodiment 32 are identical, compound 3-23.MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.75%, H:4.67%, N:7.58%.Productive rate 42.4%.
Embodiment 84 compound 3-24's is synthetic
Selecting midbody M and 6-(1-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-24.MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.74%, H:4.70%, N:7.56%.Productive rate 42.5%.
Embodiment 85 compound 3-25's is synthetic
Selecting midbody K and 6-(2-naphthalene)-2-pyridine boric acid for use is raw material, the three-step reaction that warp and embodiment 1 are identical, compound 3-25.Product MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.90%, H:4.49%, N:7.61%.Productive rate 40.7%.
Embodiment 86 compound 3-26's is synthetic
Selecting midbody K and 6-(2-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-26.Product MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.74%, H:4.68%, N:7.58%.Productive rate 40.3%.
Embodiment 87 compound 3-27's is synthetic
Selecting midbody K and 5-(2-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-27.Product MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.85%, H:4.70%, N:7.45%.Productive rate 41.7%.
Embodiment 88 compound 3-28's is synthetic
Selecting midbody K and 6-(2-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-28.Product MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.74%, H:4.71%, N:7.55%.Productive rate 40.8%.
Embodiment 89 compound 3-29's is synthetic
Selecting midbody K and 5-(2-naphthalene)-2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-29.Product MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.67%, H:4.72%, N:7.61%.Productive rate 40.7%.
Embodiment 90 compound 3-30's is synthetic
Selecting midbody K and 6-(2-naphthalene)-3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-30.Product MS (m/e): 738, ultimate analysis (C 54H 34N 4): theoretical value C:87.78%, H:4.64%, N:7.58%; Measured value C:87.85%, H:4.72%, N:7.43%.Productive rate 41.4%.
Embodiment 91-120 is similar to embodiment 61-90, and K is changed to G with midbody, is shown in the following figure:
Figure BSA00000402025600361
The preparation of compound F 17-hydroxy-corticosterone is shown in the following figure:
Figure BSA00000402025600362
Embodiment 121 compound 3-61's is synthetic
Select for use midbody K and 3-(2-pyridine) base-phenylo boric acid with for raw material, the reaction that warp and embodiment 32 are identical, compound 3-61.MS (m/e) 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.11%, H:4.65%, N:8.24%.Productive rate 41.2%.
Embodiment 122 compound 3-62's is synthetic
Selecting midbody K and 3-(3-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-62.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.15%, H:4.75%, N:8.10%.Productive rate 39.7%.
Embodiment 123 compound 3-63's is synthetic
Selecting midbody K and 3-(2-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-63.MS (m/e) 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.22%, H:4.66%, N:8.12%.Productive rate 41.4%.
Embodiment 124 compound 3-64's is synthetic
Selecting midbody K and 4-(2-pyridine) base-phenylo boric acid for use is raw material, and the reaction that warp and embodiment 32 are identical obtains compound 3-64.MS (m/e) 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.20%, H:4.76%, N:8.04%.Productive rate 43.6%.
Embodiment 125 compound 3-65's is synthetic
Selecting midbody K and 4-(3-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-65.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.09%, H:4.78%, N:8.13%.Productive rate 42.5%.
Embodiment 126 compound 3-66's is synthetic
Selecting midbody K and 4-(4-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-66.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.27%, H:4.72%, N:8.01%.Productive rate 40.2%.
Embodiment 127 compound 3-67's is synthetic
Selecting midbody G and 3-(2-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-67.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.15%, H:4.65%, N:8.20%.Productive rate 42.7%.
Embodiment 128 compound 3-68's is synthetic
Selecting midbody G and 3-(3-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-68.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.14%, H:4.77%, N:8.09%.Productive rate 41.4%.
Embodiment 129 compound 3-69's is synthetic
Selecting for use with midbody G and 3-(4-pyridine) base-phenylo boric acid is raw material, the reaction that warp and embodiment 32 are identical, compound 3-69.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.24%, H:4.71%, N:8.05%.Productive rate 42.8%.
Embodiment 130 compound 3-70's is synthetic
Selecting midbody G and 4-(2-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-70.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.24%, H:4.63%, N:8.13%.Productive rate 41.5%.
Embodiment 131 compound 3-71's is synthetic
Selecting midbody G and 4-(3-pyridine) base-phenylo boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-71.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.16%, H:4.73%, N:8.09%.Productive rate 40.8%.
Embodiment 132 compound 3-72's is synthetic
Selecting for use with midbody G and 4-(4-pyridine) base-phenylo boric acid is raw material, the reaction that warp and embodiment 32 are identical, compound 3-72.MS (m/e): 688, ultimate analysis (C 50H 32N 4): theoretical value C:87.18%, H:4.68%, N:8.13%; Measured value C:87.12%, H:4.76%, N:8.12%.Productive rate 43.4%.
Embodiment 133 compound 3-73's is synthetic
Selecting midbody K and 2-pyridine boric acid for use is raw material, and the reaction that warp and embodiment 32 are identical obtains compound 3-73.MS (m/e) 612, ultimate analysis (C 44H 28N 4): theoretical value C:86.25%, H:4.61%, N:9.14%; Measured value C:86.20%, H:4.66%, N:9.14%.Productive rate 40.6%.
Embodiment 134 compound 3-74's is synthetic
Selecting midbody K and 3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-74.MS (m/e): 612, ultimate analysis (C 44H 28N 4): theoretical value C:86.25%, H:4.61%, N:9.14%; Measured value C:86.19%, H:4.70%, N:9.11%.Productive rate 41.3%.
Embodiment 135 compound 3-75's is synthetic
Selecting midbody K and 4-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-75.MS (m/e): 612, ultimate analysis (C 44H 28N 4): theoretical value C:86.25%, H:4.61%, N:9.14%; Measured value C:86.27%, H:4.72%, N:9.01%.Productive rate 40.8%.
Embodiment 136 compound 3-76's is synthetic
Selecting midbody G and 2-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-76.MS (m/e): 612, ultimate analysis (C 44H 28N 4): theoretical value C:86.25%, H:4.61%, N:9.14%; Measured value C:86.15%, H:4.65%, N:9.20%.Productive rate 43.8%.
Embodiment 137 compound 3-77's is synthetic
Selecting midbody G and 3-pyridine boric acid for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-77.MS (m/e): 612, ultimate analysis (C 44H 28N 4): theoretical value C:86.25%, H:4.61%, N:9.14%; Measured value C:86.18%, H:4.70%, N:9.12%.Productive rate 41.4%.
Embodiment 138 compound 3-78's is synthetic
Select for use and use midbody G and 4-pyridine boric acid to be raw material, the reaction that warp and embodiment 32 are identical, compound 3-78.MS (m/e): 612, ultimate analysis (C 44H 28N 4): theoretical value C:86.25%, H:4.61%, N:9.14%; Measured value C:86.24%, H:4.71%, N:9.05%.Productive rate 42.4%.
Embodiment 139 compound 3-79's is synthetic
Selecting midbody C and 2-bromine triphenylene for use is raw material, the reaction that warp and embodiment 32 are identical, compound 3-79.MS (m/e): 535, ultimate analysis (C 39H 25N 3): theoretical value C:87.45%, H:4.70%, N:7.84%; Measured value C:87.44%, H:4.63%, N:7.93%.Productive rate 40.6%.
Embodiment 140 compound 3-80's is synthetic
Selecting midbody F and 2-bromine triphenylene for use is raw material, the reaction that warp and embodiment 1 are identical, compound 3-80.MS (m/e): 535, ultimate analysis (C 39H 25N 3): theoretical value C:87.45%, H:4.70%, N:7.84%; Measured value C:87.50%, H:4.63%, N:7.87%.Productive rate 42.6%.
Be the application implementation example of The compounds of this invention below:
Embodiment 141: the preparation of electroluminescence device and result:
The preferred implementation of fabricate devices:
(1) adopt compound of the present invention as the electron transport material in the OLED device:
Device architecture: ITO/NPB (40nm)/EM1 (30nm)/ETL (The compounds of this invention) (20nm)/LiF (0.5nm)/Al (150nm).Material structure is shown in the following figure:
Figure BSA00000402025600391
It is following that device prepares process: sheet glass supersound process in commercial clean-out system that will be coated with the ITO transparency conducting layer; In deionized water, wash; At acetone: ultrasonic oil removing in the alcohol mixed solvent; Under clean environment, be baked to and remove moisture content fully, with UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
Place the above-mentioned anodic glass substrate that has in the vacuum chamber, be evacuated to 1 * 10 -5～9 * 10 -3Pa, vacuum evaporation NPB is as hole transmission layer on above-mentioned anode tunic, and vapor deposition speed is 0.1nm/s, and the vapor deposition thickness is 40nm;
Vacuum evaporation EM1 is as the luminescent layer of device on hole transmission layer, and vapor deposition speed is 0.1nm/s, and the vapor deposition total film thickness is 30nm;
Vacuum evaporation on luminescent layer-stratification compound 1-1,1-12,2-12,2-28,3-8,3-20,3-39,3-52,3-63,3-69,3-75,3-78,3-80 are as the electron transfer layer of device, and its vapor deposition speed is 0.1nm/s, and the vapor deposition total film thickness is 20nm;
Go up the negative electrode of vacuum evaporation Al layer as device at electron transfer layer (ETL), thickness is 150nm.
Device performance sees the following form:
Figure BSA00000402025600401
Can see by last table, adopt the device of The compounds of this invention to obtain effect preferably, on the basis that driving voltage reduces relatively, obtain higher luminous efficiency with respect to the device that adopts the Bphen that generally uses in the industry
(2) adopt the material of main part of compound of the present invention as phosphorescence luminescent dye in the luminescent layer of OLED device:
Adopt 1-4 of the present invention, 1-20,2-6,2-26,3-4,3-19,3-37,3-55,3-67,3-76,3-80 contrast material of main part mCP as the material of main part of this FIrpic.
Device architecture: ITO/NPB (40nm)/TCTA (10nm)/The compounds of this invention: FIrpic (30nm, 10%)/TAZ (40nm)/LiF (0.5nm)/Al (150nm).
Figure BSA00000402025600402
It is following that device prepares process:
The preparation process of the substrate of device, anode, hole transmission layer and negative electrode is the same.
On hole transmission layer, at first prepare one deck TCTA as electronic barrier layer, in order to the carrier concentration in the balancing device.Adopt the process method of double source vapor deposition to adopt mCP, compound 1-4 of the present invention, 1-20,2-6,2-26 respectively then; 3-4,3-19,3-37,3-55; 3-67,3-76,3-80 adopt the luminescent layer of FIrpic as dyestuff as main body; Control vapor deposition speed is 0.1nm/s, and the vapor deposition total film thickness is 30nm, and the doping content of FIrpic is 5%.
Vacuum evaporation on luminescent layer-layer TAZ is as the electron transfer layer of device, and its vapor deposition speed is 0.1nm/s, and the vapor deposition thickness is 40nm.
Vacuum evaporation LiF and Al layer are as the negative electrode of device on electron transfer layer, and thickness is 150nm.
Device performance sees the following form:
The luminescent layer material Require brightness cd/m 2 Voltage V Current efficiency cd/A color
mCP：FIrpic 5000.00 6.0 18 indigo plants
1-4：FIrpic 5000.00 5.8 25 indigo plants
1-20：FIrpic 5000.00 5.4 23 indigo plants
2-6：FIrpic 5000.00 5.5 27 indigo plants
2-26：FIrpic 5000.00 5.3 26 indigo plants
3-4：FIrpic 5000.00 5.4 25 indigo plants
3-19：FIrpic 5000.00 5.6 28 indigo plants
3-37：FIrpic 5000.00 5.4 21.5 it is blue
3-55：FIrpic 5000.00 5.5 26 indigo plants
3-67：FIrpic 5000.00 5.6 28 indigo plants
3-76：FIrpic 5000.00 5.4 28.5 it is blue
3-80：FIrpic 5000.00 5.7 27 indigo plants
Can see that by last table the device that adopts The compounds of this invention has obtained effect preferably with respect to the phosphorescence luminescent device that adopts the mCP that generally uses in the industry as material of main part, on the basis that driving voltage reduces relatively, has obtained higher current efficiency.
Although describe the present invention in conjunction with embodiment, the present invention is not limited to the foregoing description, should be appreciated that those skilled in the art can carry out various modifications and improvement under the guiding of the present invention's design, and accompanying claims has been summarized scope of the present invention.

Claims (7)

1. organic cpds, its general structure is as shown in the formula shown in the I:
Figure FSA00000402025500011
Wherein Ar1, Ar2, Ar3 are selected from pyridine group, phenyl group, xenyl group or naphthyl group, and A, B, C are the aromatic ring of chemical bond or carbon atom 6-30, and m, n, p are respectively the integer of 0-2.
2. compound according to claim 1, can be by shown in Formula Il, III, the IV:
Figure FSA00000402025500012
3. compound according to claim 1 is characterized in that, A, B and C are selected from singly-bound, phenylene, naphthylidene, anthrylene, phenanthrylene, inferior fluoranthene base, inferior pyrenyl 、 Ya perylene base among the formula I.
4. compound according to claim 1 is characterized in that, the structural formula of Ar1, Ar2, Ar3 is selected from following formula among the formula I:
Figure FSA00000402025500021
5. according to claim 1, one of 2 or 3 described compounds, structural formula is selected from following formula:
Figure FSA00000402025500022
Figure FSA00000402025500031
Figure FSA00000402025500041
Figure FSA00000402025500061
Figure FSA00000402025500071
Figure FSA00000402025500081
Figure FSA00000402025500101
Figure FSA00000402025500121
Figure FSA00000402025500141
Figure FSA00000402025500151
Figure FSA00000402025500161
Figure FSA00000402025500171
Figure FSA00000402025500191
Figure FSA00000402025500201
6. the described compound of claim 1 is used as phosphorescence main body or electric transmission layer material in organic electroluminescence device.
7. an organic electroluminescence device wherein comprises pair of electrodes and is arranged on the organic light emitting medium between this counter electrode, comprises a kind of described compound of claim 1 that is selected from this organic light emitting medium at least.
CN2010106111777A 2010-12-17 2010-12-17 Triphenylene compound containing pyridine group and application thereof Pending CN102532105A (en)

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