CN102372708B - Pyridyl phenanthroline compound and application - Google Patents
Pyridyl phenanthroline compound and application Download PDFInfo
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- CN102372708B CN102372708B CN 201010258728 CN201010258728A CN102372708B CN 102372708 B CN102372708 B CN 102372708B CN 201010258728 CN201010258728 CN 201010258728 CN 201010258728 A CN201010258728 A CN 201010258728A CN 102372708 B CN102372708 B CN 102372708B
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- -1 Pyridyl phenanthroline compound Chemical class 0.000 title abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
- 239000000463 material Substances 0.000 claims abstract description 20
- 230000005540 biological transmission Effects 0.000 claims abstract description 8
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 65
- 238000005401 electroluminescence Methods 0.000 claims description 12
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 180
- 238000006243 chemical reaction Methods 0.000 description 101
- 238000004458 analytical method Methods 0.000 description 90
- 239000002994 raw material Substances 0.000 description 90
- 239000000047 product Substances 0.000 description 86
- 239000004327 boric acid Substances 0.000 description 59
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 36
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 31
- 229910052740 iodine Inorganic materials 0.000 description 30
- 239000011630 iodine Substances 0.000 description 30
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 18
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 18
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 15
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- MZWFYABOEZMENB-UHFFFAOYSA-N 4-bromo-2-iodopyridine Chemical compound BrC1=CC=NC(I)=C1 MZWFYABOEZMENB-UHFFFAOYSA-N 0.000 description 15
- HSNBRDZXJMPDGH-UHFFFAOYSA-N 5-bromo-2-iodopyridine Chemical compound BrC1=CC=C(I)N=C1 HSNBRDZXJMPDGH-UHFFFAOYSA-N 0.000 description 15
- 230000027756 respiratory electron transport chain Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 239000011368 organic material Substances 0.000 description 6
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
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- 238000004519 manufacturing process Methods 0.000 description 4
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- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 2
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 2
- SHBHYINHXNTBRP-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-methylsulfonylethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCS(=O)(=O)C)C=CC=1 SHBHYINHXNTBRP-UHFFFAOYSA-N 0.000 description 2
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- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 2
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- FVQKGQNSCKJPIJ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCN2C(OCC2)=O)C=CC=1 FVQKGQNSCKJPIJ-UHFFFAOYSA-N 0.000 description 2
- AJZDHLHTTJRNQJ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(tetrazol-1-yl)ethyl]benzamide Chemical compound N1(N=NN=C1)CCNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O AJZDHLHTTJRNQJ-UHFFFAOYSA-N 0.000 description 2
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 2
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 2
- NRLQBVLOUUPAMI-UHFFFAOYSA-N 8-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2CCC3(CNC(O3)=O)CC2)C=CC=1 NRLQBVLOUUPAMI-UHFFFAOYSA-N 0.000 description 2
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 2
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
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- YKKPYMXANSSQCA-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3-pyrazol-1-ylazetidin-1-yl)methanone Chemical compound N1(N=CC=C1)C1CN(C1)C(=O)C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F YKKPYMXANSSQCA-UHFFFAOYSA-N 0.000 description 2
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- BYWBCSRCPLBDFU-CYBMUJFWSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3R)-3-aminopyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@@H](CC1)N BYWBCSRCPLBDFU-CYBMUJFWSA-N 0.000 description 2
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- JWSIZPAOIFLWKM-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[3-(dimethylamino)-4-hydroxypyrrolidin-1-yl]methanone Chemical compound CN(C)C1CN(CC1O)C(=O)c1cccc(Oc2cc(CN)cc(n2)C(F)(F)F)c1 JWSIZPAOIFLWKM-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- ANQSYQOHGAJRKN-UHFFFAOYSA-N 1,1'-biphenyl;boric acid Chemical compound OB(O)O.C1=CC=CC=C1C1=CC=CC=C1 ANQSYQOHGAJRKN-UHFFFAOYSA-N 0.000 description 1
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- XIYPPJVLAAXYAB-UHFFFAOYSA-N 2-bromo-6-phenylpyridine Chemical compound BrC1=CC=CC(C=2C=CC=CC=2)=N1 XIYPPJVLAAXYAB-UHFFFAOYSA-N 0.000 description 1
- PQGJDTVHKBKIRX-UHFFFAOYSA-N 2-pyridin-2-yl-1,10-phenanthroline Chemical class N1=CC=CC=C1C1=CC=C(C=CC=2C3=NC=CC=2)C3=N1 PQGJDTVHKBKIRX-UHFFFAOYSA-N 0.000 description 1
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- 125000005259 triarylamine group Chemical group 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical class CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
The invention provides a novel compound which has a symmetric structure, is simple to prepare, has high luminescence efficiency and high carrier mobility, and can be used in electronic transmission layer of an electroluminescent element. An applied device can be used to obviously reduce driving voltage and raise current efficiency. The general formula of the material is as shown in the formula I, wherein mother nucleus is selected from 2,9-disubstituted, 3,8-disubstituted and 4,7 disubstituted 1,10-Phenanthroline and end group Ar is selected from phenyl group, biphenyl group and naphthalene group.
Description
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
As a rule, electron transport material all has the plane aromatics of big conjugated structure, they have the ability of accepting electronics preferably mostly, under certain forward bias, can effectively transmit electronics again simultaneously, at present known well behaved electron transport material is also few, available electron transport material mainly contains oxine aluminium compounds at present, the furodiazole compound, quinoxaline compound, the polymkeric substance of nitrile group-containing, (Chem.Mater.2004 such as other nitrogen-containing heterocycle compound, 16,4556-4573, J Mater.Chem.2005,15,94-106).
Therefore will design an electron transport material that organic electroluminescence device efficient is significantly promoted, need possess following character: (1) has reversible electrochemical reduction and enough high reduction potentials; (2) need there be appropriate H OMO and LUMO to make electronics that minimum injection energy gap be arranged, to reduce initial and operating voltage; (3) higher electronics rate of flow need be arranged; (4) has the stable and thermostability of good gamma transition; (5) has noncrystalline film.(electroluminescent organic material and element, the prosperous yellow filial piety literary composition of Chen Jin work, five southern bibliogony companies).
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.
From the relation of compound structure and character, the reduction potential of heterogeneous ring compound is lower than the pure aromatic series of analog structure, is conducive to accept electronics, thereby shows electric transmission character preferably.The phenanthroline analog derivative has conjugate planes and lower HOMO energy level preferably, so we are connected to the pyridyl group of electron deficiency on the phenanthroline base, can show high electronics flowability; The molecular structure symmetry can increase the regularity of molecular stacks simultaneously, has also improved carrier mobility to a certain extent.The nonplanarity of phenylpyridyl, xenyl pyridyl or naphthyl pyridyl can form uniform noncrystalline shape film so that this compounds has to a certain degree distortion at space multistory when being more conducive to vacuum evaporation.Compound of the present invention at room temperature has advantages of higher stability, and applied device also has advantages of higher stability.
The present invention develops a kind of novel organic materials, and preparation is simple and this material has good thermostability, and high electronic mobility can be used as electron transfer layer in organic electroluminescence device.
The present invention discloses a class novel cpd, and its general structure is as shown in the formula shown in the I:
Wherein Ar is selected from phenyl group, xenyl group or naphthyl group.
Pyridine group among following formula I the position of substitution on 1,10-phenanthroline base is selected from 2,9 two replacements, 3,8 two replacement or 4,7 two replacements, and the structural formula that is substituted of 1,10-phenanthroline base is selected from Formula Il, III or IV:
The concrete structure of Ar among the following formula I is selected from following formula V, VI, VII, VIII or IX:
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:
Organic materials of the present invention is used as 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 the electron transport material in the organic function layer.
Organic materials of the present invention has higher electronic mobility, can be used as electron transfer layer in display of organic electroluminescence.
Embodiment
Among the present invention used basic chemical industry raw materials such as haloperidid, phenylo boric acid, biphenyl boric acid, naphthalene boronic acids and various two bromos, 1,10 phenanthrolines all at home Chemicals market bought, various aryl pyridine ylboronic acids all available common organic method are synthetic.
Embodiment
Compound process in the present invention mainly divided for three steps: (1) is normally by Suzuki linked reaction (Journal of Organometallic Chenistry1999,576,147-168) aromatic ring and pyridine ring are coupled together, generate the aryl-pyridine of getting of single halo; (2) resulting halides in 1 is become pyridine boric acid (OrganicSyntheses2005, Vol.81, p.89); (3) two bromos 1 that boric acid and the different positions of gained in 2 replaced, the coupling of 10-phenanthroline is got up, get final product target molecule.Above-mentioned steps specifically is described below:
Embodiment 1 compound 1-1's is synthetic
(1) the first step
23.5g 2,6-dibromo pyridine, 12.0g phenylo boric acid and 0.50g Pd (PPh
3)
4Be dissolved in the 300mL toluene, 22.0g salt of wormwood is dissolved in the 100mL water adds in the above reaction solution, add 200mL ethanol again, 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 sherwood oil: dichloro=5: 1 (V
1/ V
2) must faint yellow solid 14.70g.MS (m/e): 234, fusing point 47-49 °, productive rate 62.8%.
(2) second steps
23.4g 2-bromo-6-phenylpyridine and 24.6 gram triisopropyl borate esters are dissolved in the tetrahydrofuran (THF) of 200mL drying, are cooled to-40 ℃ of Dropwise 5 0mL butyllithiums (2.5M), the control temperature is between-40 ℃ to-50 ℃.Finish between-40 ℃ to-50 ℃ and be incubated 30 minutes, remove cryostat, be warming up to-20 ℃ naturally, slowly add the solution that 20 milliliters of concentrated hydrochloric acids and 80 ml waters are made into, rise to 15 ℃ more naturally, separatory, water layer transfers pH to neutral with 10% sodium carbonate solution, and it is saturated to add 40g sodium-chlor again, extracts with ethyl acetate 40mL * 3, merge organic layer, use dried over mgso 30 minutes, the elimination siccative, be evaporated to dried, obtain white solid 15.8 grams, MS (m/e): 199, productive rate 79.4%.
(3) the 3rd steps
8.45g, 2,9 two bromo-1,10-phenanthroline and 12.0g 6-phenyl-pyridine-2-boric acid are dissolved in the mixing solutions of 400mL dimethylbenzene and 300mL ethanol, add 13.8g salt of wormwood and 0.5g Pd (PPh
3)
4, refluxing, reaction solution becomes yellow, behind the reaction 2h, adds 2.00g 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 4.50g at last, be compound 1-1.MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.80%, H:4.62%, N:11.58%, productive rate 37.2%.
Embodiment 2-30 prepares route with the preparation of 1-1 compound among the embodiment 1, and difference only is in the first step position of halogen in the phenylpyridyl, and this can select different reaction substrates according to concrete target molecule, now specifically is described below:
Embodiment 2 compound 1-2's is synthetic
Selecting 2-chloro-4-iodine pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-2, MS (m/e): 486, and ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.97%, H:4.48%, N:11.55%.Overall yield is 36.5%.
Embodiment 3 compound 1-3's is synthetic
Selecting 3,5-dibromo pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-3.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.99%, H:4.62%, N:11.39%.Overall yield is 34.9%.
Embodiment 4 compound 1-4's is synthetic
Selecting 2-iodo-4-bromopyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-4.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.97%, H:4.72%, N:11.31%.Overall yield is 45.2%.
Embodiment 5 compound 1-5's is synthetic
Selecting 2,6-dibromo pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-5.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.32%, H:4.82%, N:8.86%.Overall yield is 35.4%.
Embodiment 6 compound 1-6's is synthetic
Selecting 2-chloro-4-iodine pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-6.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.41%, H:4.81%, N:8.78%.Overall yield is 36.5%.
Embodiment 7 compound 1-7's is synthetic
Selecting 3,5-dibromo pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-7.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.37%, H:4.80%, N:8.93%.Overall yield is 27.8%.
Embodiment 8 compound 1-8's is synthetic
Selecting 2-iodo-4-bromopyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-8.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.53%, H:4.71%, N:8.76%.Overall yield is 41.2%.
Embodiment 9 compound 1-9's is synthetic
Selecting 2,6-dibromo pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-9.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.39%, H:4.75%, N:8.86%.Overall yield is 27.6%.
Embodiment 10 compound 1-10's is synthetic
Selecting 2-chloro-4-iodine pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-10.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.45%, H:4.86%, N:8.69%.Overall yield is 36.2%.
Embodiment 11 compound 1-11's is synthetic
Selecting 3,5-dibromo pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-11.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.38%, H:4.80%, N:8.82%.Overall yield is 29.3%.
Embodiment 12 compound 1-12's is synthetic
Selecting 2-iodo-4-bromopyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-12.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.55%, H:4.70%, N:8.75%.Overall yield is 40.4%.
Embodiment 13 compound 1-13's is synthetic
Selecting 2,6-dibromo pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-13.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.02%, H:4.52%, N:9.44%.Overall yield is 26.8%.
Embodiment 14 compound 1-14's is synthetic
Selecting 2-chloro-4-iodine pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-14.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.08%, H:4.51%, N:9.41%.Overall yield is 37.5%.
Embodiment 15 compound 1-15's is synthetic
Selecting 3,5-dibromo pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-15.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.10%, H:4.42%, N:9.48%.Overall yield is 28.8%.
Embodiment 16 compound 1-16's is synthetic
Selecting 2-iodo-4-bromopyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-16.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.13%, H:4.40%, N:9.47%.Overall yield is 36.8%.
Embodiment 17 compound 1-17's is synthetic
Selecting 2,6-dibromo pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-17.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.06%, H:4.52%, N:9.42%.Overall yield is 27.6%.
Embodiment 18 compound 1-18's is synthetic
Selecting 2-chloro-4-iodine pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-18.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:85.88%, H:4.57%, N:9.55%.Overall yield is 37.8%.
Embodiment 19 compound 1-19's is synthetic
Selecting 3,5-dibromo pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-19.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.13%, H:4.41%, N:9.46%.Overall yield is 30.8%.
Embodiment 20 compound 1-20's is synthetic
Selecting 2-iodo-4-bromopyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-20.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.03%, H:4.35%, N:9.62%.Overall yield is 37.9%.
Embodiment 21 compound 1-21's is synthetic
Selecting 2-chloro-5-iodine pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-21.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.83%, H:4.70%, N:11.47%.Overall yield is 43.1%.
Embodiment 22 compound 1-22's is synthetic
Selecting 2-iodo-5-bromopyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-22.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.97%, H:4.72%, N:11.31%.Overall yield is 42.2%.
Embodiment 23 compound 1-23's is synthetic
Selecting 2-chloro-5-iodine pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-23.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.52%, H:4.65%, N:8.83%.Overall yield is 42.1%.
Embodiment 24 compound 1-24's is synthetic
Selecting 2-iodo-5-bromopyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-24.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.58%, H:4.70%, N:8.72%.Overall yield is 41.2%.
Embodiment 25 compound 1-25's is synthetic
Selecting 2-chloro-5-iodine pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-25.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.42%, H:4.63%, N:8.95%.Overall yield is 41.0%.
Embodiment 26 compound 1-26's is synthetic
Selecting 2-iodo-5-bromopyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-26.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.51%, H:4.79%, N:8.70%.Overall yield is 40.8%.
Embodiment 27 compound 1-27's is synthetic
Selecting 2-chloro-5-iodine pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-27.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.10%, H:4.40%, N:9.50%.Overall yield is 37.3%.
Embodiment 28 compound 1-28's is synthetic
Selecting 2-iodo-5-bromopyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-28.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.05%, H:4.42%, N:9.53%.Overall yield is 36.8%.
Embodiment 29 compound 1-29's is synthetic
Selecting 2-chloro-5-iodine pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-29.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.11%, H:4.37%, N:9.52%.Overall yield is 38.2%.
Embodiment 30 compound 1-30's is synthetic
Selecting 2-iodo-5-bromopyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 1-30.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.06%, H:4.56%, N:9.48%.Overall yield is 36.9%.
What use in the three-step reaction among the embodiment 31-60 is 3,8-two bromos-1, and the 10-phenanthroline, other is with embodiment 1.Specifically be described below:
Embodiment 31 compound 2-1's is synthetic
Selecting 2,6-dibromo pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-1.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.89%, H:4.52%, N:11.59%.Overall yield is 27.3%.
Embodiment 32 compound 2-2's is synthetic
Selecting 2-chloro-4-iodine pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-2, MS (m/e): 486, and ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.98%, H:4.46%, N:11.55%.Overall yield is 33.5%.
Embodiment 33 compound 2-3's is synthetic
Selecting 3,5-dibromo pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-3.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.79%, H:4.66%, N:11.57%.Overall yield is 32.4%.
Embodiment 34 compound 2-4's is synthetic
Selecting 2-iodo-4-bromopyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-4.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.87%, H:4.73%, N:11.40%.Overall yield is 40.2%.
Embodiment 35 compound 2-5's is synthetic
Selecting 2,6-dibromo pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-5.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.36%, H:4.83%, N:8.81%.Overall yield is 28.3%.
Embodiment 36 compound 2-6's is synthetic
Selecting 2-chloro-4-iodine pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-6.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.60%, H:4.81%, N:8.59%.Overall yield is 36.7%.
Embodiment 37 compound 2-7's is synthetic
Selecting 3,5-dibromo pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-7.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.35%, H:4.80%, N:8.85%.Overall yield is 31.8%.
Embodiment 38 compound 2-8's is synthetic
Selecting 2-iodo-4-bromopyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-8.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.43%, H:4.71%, N:8.86%.Overall yield is 40.5%.
Embodiment 39 compound 2-9's is synthetic
Selecting 2,6-dibromo pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-9.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.37%, H:4.75%, N:8.88%.Overall yield is 29.5%.
Embodiment 40 compound 2-10's is synthetic
Selecting 2-chloro-4-iodine pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-10.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.41%, H:4.86%, N:8.73%.Overall yield is 36.7%.
Embodiment 41 compound 2-11's is synthetic
Selecting 3,5-dibromo pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-11.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.37%, H:4.91%, N:8.82%.Overall yield is 32.4%.
Embodiment 42 compound 2-12's is synthetic
Selecting 2-iodo-4-bromopyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-12.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.56%, H:4.70%, N:8.74%.Overall yield is 41.6%.
Embodiment 43 compound 2-13's is synthetic
Selecting 2,6-dibromo pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-13.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.08%, H:4.52%, N:9.40%.Overall yield is 28.8%.
Embodiment 44 compound 2-14's is synthetic
Selecting 2-chloro-4-iodine pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-14.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.05%, H:4.57%, N:9.38%.Overall yield is 37.5%.
Embodiment 45 compound 2-15's is synthetic
Selecting 3,5-dibromo pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-15.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.11%, H:4.44%, N:9.45%.Overall yield is 29.6%.
Embodiment 46 compound 2-16's is synthetic
Selecting 2-iodo-4-bromopyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-16.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:85.93%, H:4.50%, N:9.57%.Overall yield is 37.8%.
Embodiment 47 compound 2-17's is synthetic
Selecting 2,6-dibromo pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-17.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.07%, H:4.55%, N:9.38%.Overall yield is 28.7%.
Embodiment 48 compound 2-18's is synthetic
Selecting 2-chloro-4-iodine pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-18.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:85.92%, H:4.57%, N:9.51%.Overall yield is 38.8%.
Embodiment 49 compound 2-19's is synthetic
Selecting 3,5-dibromo pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-19.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.10%, H:4.41%, N:9.49%.Overall yield is 31.4%.
Embodiment 50 compound 2-20's is synthetic
Selecting 2-iodo-4-bromopyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-20.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.12%, H:4.35%, N:9.53%.Overall yield is 37.5%.
Embodiment 51 compound 2-21's is synthetic
Selecting 2-chloro-5-iodine pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-21.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.81%, H:4.70%, N:11.49%.Overall yield is 43.4%.
Embodiment 52 compound 2-22's is synthetic
Selecting 2-iodo-5-bromopyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-22.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.98%, H:4.65%, N:11.37%.Overall yield is 42.7%.
Embodiment 53 compound 2-23's is synthetic
Selecting 2-chloro-5-iodine pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-23.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.55%, H:4.65%, N:8.80%.Overall yield is 40.1%.
Embodiment 54 compound 2-24's is synthetic
Selecting 2-iodo-5-bromopyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-24.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%: measured value C:86.57%, H:4.60%, N:8.83%.Overall yield is 41.3%.
Embodiment 55 compound 2-25's is synthetic
Selecting 2-chloro-5-iodine pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-25.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.41%, H:4.69%, N:8.90%.Overall yield is 41.8%.
Embodiment 56 compound 2-26's is synthetic
Selecting 2-iodo-5-bromopyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-26.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.56%, H:4.79%, N:8.65%.Overall yield is 40.7%.
Embodiment 57 compound 2-27's is synthetic
Selecting 2-chloro-5-iodine pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-27.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.11%, H:4.41%, N:9.48%.Overall yield is 37.3%.
Embodiment 58 compound 2-28's is synthetic
Selecting 2-iodo-5-bromopyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-28.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.06%, H:4.42%, N:9.52%.Overall yield is 36.8%.
Embodiment 59 compound 2-29's is synthetic
Selecting 2-chloro-5-iodine pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-29.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.07%, H:4.37%, N:9.56%.Overall yield is 39.2%.
Embodiment 60 compound 2-30's is synthetic
Selecting 2-iodo-5-bromopyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 2-30.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.03%, H:4.56%, N:9.41%.Overall yield is 37.5%.
What use in the three-step reaction among the embodiment 61-90 is 4,7-two bromos-1, and the 10-phenanthroline, other is with embodiment 1.
Execute the synthetic of example 61 compound 3-1
Selecting 2,6-dibromo pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-1.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.90%, H:4.62%, N:11.48%.Overall yield is 28.6%.
Embodiment 62 compound 3-2's is synthetic
Selecting 2-chloro-4-iodine pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-2, MS (m/e): 486, and ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.85%, H:4.58%, N:11.57%.Overall yield is 38.5%.
Embodiment 63 compound 3-3's is synthetic
Selecting 3,5-dibromo pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-3.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.78%, H:4.62%, N:11.60%.Overall yield is 28.3%.
Embodiment 64 compound 3-4's is synthetic
Selecting 2-iodo-4-bromopyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-4.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.82%, H:4.72%, N:11.36%.Overall yield is 40.2%.
Embodiment 65 compound 3-5's is synthetic
Selecting 2,6-dibromo pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-5.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.37%, H:4.82%, N:8.91%.Overall yield is 28.4%.
Embodiment 66 compound 3-6's is synthetic
Selecting 2-chloro-4-iodine pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-6.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.40%, H:4.81%, N:8.79%.Overall yield is 36.7%.
Embodiment 67 compound 3-7's is synthetic
Selecting 3,5-dibromo pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-7.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.35%, H:4.80%, N:8.85%.Overall yield is 33.8%.
Embodiment 68 compound 3-8's is synthetic
Selecting 2-iodo-4-bromopyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-8.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.56%, H:4.71%, N:8.73%.Overall yield is 40.2%.
Embodiment 69 compound 3-9's is synthetic
Selecting 2,6-dibromo pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-9.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.36%, H:4.85%, N:8.79%.Overall yield is 29.6%.
Embodiment 70 compound 3-10's is synthetic
Selecting 2-chloro-4-iodine pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-10.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.42%, H:4.86%, N:8.74%.Overall yield is 36.8%.
Embodiment 71 compound 3-11's is synthetic
Selecting 3,5-dibromo pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-11.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.35%, H:4.84%, N:8.81%.Overall yield is 29.3%.
Embodiment 72 compound 3-12's is synthetic
Selecting 2-iodo-4-bromopyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-12.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.56%, H:4.64%, N:8.80%.Overall yield is 40.8%.
Embodiment 73 compound 3-13's is synthetic
Selecting 2,6-dibromo pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-13.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.05%, H:4.52%, N:9.43%.Overall yield is 26.8%.
Embodiment 74 compound 3-14's is synthetic
Selecting 2-chloro-4-iodine pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-14.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.09%, H:4.51%, N:9.40%.Overall yield is 38.5%.
Embodiment 75 compound 3-15's is synthetic
Selecting 3,5-dibromo pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-15.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.12%, H:4.42%, N:9.44%.Overall yield is 32.8%.
Embodiment 76 compound 3-16's is synthetic
Selecting 2-iodo-4-bromopyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-16.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.07%, H:4.53%, N:9.47%.Overall yield is 36.6%.
Embodiment 77 compound 3-17's is synthetic
Selecting 2,6-dibromo pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-17.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:85.86%, H:4.62%, N:9.52%.Overall yield is 29.6%.
Embodiment 78 compound 3-18's is synthetic
Selecting 2-chloro-4-iodine pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-18.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:85.87%, H:4.59%, N:9.54%.Overall yield is 38.8%.
Embodiment 79 compound 3-19's is synthetic
Selecting 3,5-dibromo pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-19.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.04%, H:4.51%, N:9.45%.Overall yield is 32.8%.
Embodiment 80 compound 3-20's is synthetic
Selecting 2-iodo-4-bromopyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-20.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:85.93%, H:4.55%, N:9.52%.Overall yield is 37.6%.
Embodiment 81 compound 3-21's is synthetic
Selecting 2-chloro-5-iodine pyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-21.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.86%, H:4.70%, N:11.44%.Overall yield is 41.1%.
Embodiment 82 compound 3-22's is synthetic
Selecting 2-iodo-5-bromopyridine and phenylo boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-22.Product MS (m/e): 486, ultimate analysis (C
34H
22N
4): theoretical value C:83.93%, H:4.56%, N:11.51%; Measured value C:83.95%, H:4.72%, N:11.33%.Overall yield is 41.2%.
Embodiment 83 compound 3-23's is synthetic
Selecting 2-chloro-5-iodine pyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-23.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.57%, H:4.65%, N:8.78%.Overall yield is 42.4%.
Embodiment 84 compound 3-24's is synthetic
Selecting 2-iodo-5-bromopyridine and 4-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-24.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.58%, H:4.70%, N:8.72%.Overall yield is 41.8%.
Embodiment 85 compound 3-25's is synthetic
Selecting 2-chloro-5-iodine pyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-25.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.60%, H:4.62%, N:8.78%.Overall yield is 41.2%.
Embodiment 86 compound 3-26's is synthetic
Selecting 2-iodo-5-bromopyridine and 3-biphenyl boric acid for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-26.Product MS (m/e): 638, ultimate analysis (C
46H
30N
4): theoretical value C:86.49%, H:4.73%, N:8.77%; Measured value C:86.56%, H:4.79%, N:8.65%.Overall yield is 40.6%.
Embodiment 87 compound 3-27's is synthetic
Selecting 2-chloro-5-iodine pyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-27.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.10%, H:4.42%, N:9.48%.Overall yield is 37.7%.
Embodiment 88 compound 3-28's is synthetic
Selecting 2-iodo-5-bromopyridine and 1-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-28.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.08%, H:4.42%, N:9.50%.Overall yield is 38.8%.
Embodiment 89 compound 3-29's is synthetic
Selecting 2-chloro-5-iodine pyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-29.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.01%, H:4.37%, N:9.62%.Overall yield is 39.2%.
Embodiment 90 compound 3-30's is synthetic
Selecting 2-iodo-5-bromopyridine and 2-naphthalene boronic acids for use is raw material, and the three-step reaction through identical with embodiment 1 obtains compound 3-30.Product MS (m/e): 586, ultimate analysis (C
42H
26N
4): theoretical value C:85.98%, H:4.47%, N:9.55%; Measured value C:86.05%, H:4.57%, N:9.48%.Overall yield is 36.9%.
Be the Application Example of The compounds of this invention below:
Embodiment 91: the preparation of electroluminescence device and result
The preferred implementation of fabricate devices:
(1) designs
The transmission performance that compares these electron transport materials for convenience, the present invention has designed a simple electroluminescence device (substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode), only use compound 1-1,1-5,1-13 and 1-21 as the electron transport material illustration, efficent electronic transport material Bphen is material as a comparison, (EM1 is material of main part to EM1 as the luminescent material illustration, it is not luminescent material, purpose is not to pursue high-level efficiency, but verifies the possibility of these material practicalities).The structure of Bphen and EM1 is:
Substrate can use the substrate in traditional organic luminescent device, for example: glass or plastics.Select glass substrate for use in element manufacturing of the present invention, ITO makes anode material.
Hole transmission layer can adopt various tri-arylamine group materials.Selected hole mobile material is NPB in element manufacturing of the present invention.
Negative electrode can adopt metal and composition thereof structure, as Mg:Ag, Ca:Ag etc., also can be electron injecting layer/metal-layer structure, as common cathode constructions such as LiF/Al, Li2O.Electronics injecting material selected in element manufacturing of the present invention is LiF, and cathode material is Al.
(2) element manufacturing
Sheet glass supersound process in commercial clean-out system of ITO transparency conducting layer will be coated with, wash in deionized water, at acetone: ultrasonic oil removing in the alcohol mixed solvent is baked under clean environment and removes moisture content fully, with UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
The above-mentioned glass substrate that has anode is placed in the vacuum chamber, be evacuated to 1 * 10
-5～9 * 10
-3Pa, as hole transmission layer, evaporation speed is 0.1nm/s at above-mentioned anode tunic vacuum evaporation NPB, the evaporation thickness is 50nm;
Vacuum evaporation EM1 or EM2 are as the luminescent layer of device on hole transmission layer, and evaporation speed is 0.1nm/s, and the evaporation total film thickness is 30nm;
Vacuum evaporation one deck compound 1-1,1-5,1-13,1-21 or Bphen are as the electron transfer layer of device on luminescent layer, and its evaporation speed is 0.1nm/s, and the evaporation total film thickness is 50nm;
Go up vacuum evaporation Al layer as the negative electrode of device at electron transfer layer (ETL), thickness is 150nm.
Device performance see the following form (device architecture: ITO/NPB (40nm)/EM1 (30nm)/ETL material (20nm)/LiF (0.5nm)/Al (150nm))
Above result shows that novel organic materials of the present invention can be preferably used as electron transfer layer in organic electroluminescence device.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, 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 claims have been summarized scope of the present invention.
Claims (6)
1. organic compound, its general structure is as shown in the formula shown in the I:
Wherein Ar is selected from phenyl group, xenyl group or naphthyl group.
2. compound according to claim 1 is characterized in that the pyridine group the position of substitution on 1,10-phenanthroline base among the formula I is selected from 2,9 two replacements, 3,8 two replacement or 4,7 two replacements, the structural formula that is substituted of 1,10-phenanthroline base is selected from Formula Il, III or IV:
3. compound according to claim 1 is characterized in that, the structural formula of Ar is selected from following formula V, VI, VII, VIII or IX among the formula I:
4. according to claim 1, one of 2 or 3 described compounds, structural formula is selected from following formula:
5. the described compound of claim 1 is used as the electric transmission layer material in organic electroluminescence device.
6. organic electroluminescence device wherein comprises pair of electrodes and is arranged on 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.
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| EP3252837B1 (en) | 2016-05-30 | 2021-05-05 | Novaled GmbH | Organic light emitting diode comprising an organic semiconductor layer |
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| EP0564224A2 (en) * | 1992-04-03 | 1993-10-06 | Pioneer Electronic Corporation | Organic electroluminescene device |
| WO2010075379A2 (en) * | 2008-12-22 | 2010-07-01 | E. I. Du Pont De Nemours And Company | Electronic device including phenanthroline derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0564224A2 (en) * | 1992-04-03 | 1993-10-06 | Pioneer Electronic Corporation | Organic electroluminescene device |
| WO2010075379A2 (en) * | 2008-12-22 | 2010-07-01 | E. I. Du Pont De Nemours And Company | Electronic device including phenanthroline derivative |
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