CN102924431A - Organic luminescent compound containing acridine core and application thereof in electroluminescent device - Google Patents
Organic luminescent compound containing acridine core and application thereof in electroluminescent device Download PDFInfo
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- CN102924431A CN102924431A CN2012104281202A CN201210428120A CN102924431A CN 102924431 A CN102924431 A CN 102924431A CN 2012104281202 A CN2012104281202 A CN 2012104281202A CN 201210428120 A CN201210428120 A CN 201210428120A CN 102924431 A CN102924431 A CN 102924431A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 230000000007 visual effect Effects 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 abstract description 3
- 238000000295 emission spectrum Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 19
- 239000000470 constituent Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 230000005540 biological transmission Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012065 filter cake Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000004949 mass spectrometry Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000027756 respiratory electron transport chain Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 210000003739 neck Anatomy 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 0 CCc1ccc(*)cc1 Chemical compound CCc1ccc(*)cc1 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 229960000286 proflavine Drugs 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- -1 xylyl amine Chemical class 0.000 description 3
- SLPTVCUECFWGKU-UHFFFAOYSA-N 1-butyl-2-iodobenzene Chemical compound CCCCC1=CC=CC=C1I SLPTVCUECFWGKU-UHFFFAOYSA-N 0.000 description 2
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YQYBUJYBXOVWQW-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3,4-dihydro-1H-isoquinolin-2-yl)methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1CC2=CC=CC=C2CC1 YQYBUJYBXOVWQW-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UIWLITBBFICQKW-UHFFFAOYSA-N 1h-benzo[h]quinolin-2-one Chemical compound C1=CC=C2C3=NC(O)=CC=C3C=CC2=C1 UIWLITBBFICQKW-UHFFFAOYSA-N 0.000 description 1
- NAIGXIXEPKSMBJ-UHFFFAOYSA-N 2-phenyl-1h-naphtho[2,1-e]benzimidazole Chemical class C1=CC=CC=C1C(N1)=NC2=C1C=CC1=C2C=CC2=CC=CC=C12 NAIGXIXEPKSMBJ-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 241000024287 Areas Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic luminescent compound containing an acridine core and application thereof in an electroluminescent device. The structural formula of the compound is shown in the specification; the compound can be used as a luminescent layer for the preparation of an electroluminescent device, thus obtaining a high-performance electroluminescent device of which the emission spectrum is in a green light region; and the electroluminescent device can be used in the application fields such as illuminating light sources, signal lamps, alphanumeric displays, indicators, photoelectric couplers, flat-panel displays and the like.
Description
Technical field
The invention belongs to technical field of organic electroluminescence, be specifically related to contain organic light emission compound and the application of these compounds in electroluminescent device of acridine core.
Background technology
Organic Light Emitting Diode is OLED(Organic Light Emitting Diode) owing to self intrinsic advantage,, wide viewing angle high such as luminous, brightness, response are fast, less energy-consumption, can make flexible display apparatus etc., are considered to the technique of display of future generation that replaces liquid crystal technology desirable.In recent years, the exploitation of luminous organic material becomes a study hotspot in materials chemistry field.The organic electroluminescent technology is hopeful to realize the panchromatic flat-panel monitor of big area at low power consuming, low-work voltage, wide visual angle.
In fact, about the organic electroluminescent phenomenon.The people such as Pope have reported the organic electroluminescent phenomenon the earliest in earlier 1960s, and they have observed the blue light that anthracene sends when applying the high pressure of four hectovolts in the anthracene single crystal both sides.But because monocrystalline is difficult to growth, device drive voltage is very high, and (400～2000V), the technique that they adopt does not almost have practical use.Until 1987, the people such as C.W.Tang of U.S. Kodak company adopt the ultrathin membrane technology with the hole transport effect preferably aromatic amine as hole transmission layer, with the aluminum complex of oxine as luminescent layer, respectively as anode and negative electrode, prepared luminescent device with tin indium oxide (ITO) film and metal alloy.This device has obtained brightness up to 1000cd/m under the 10V driving voltage
2Green emission, the efficient of device is that 1.5lm/W(sees C.W.Tang and S.A.VanSlyke, Appl.Phys.Lett., 1987,51,913).This breakthrough so that organic electroluminescent research be able to worldwide in depth carry out rapidly.
The OLED technology is used for showing several large advantages: low cost of manufacture, and active illuminating, flexibility, frivolous, response speed microsecond magnitude, high-level efficiency.Because OLED is based on the technology of organic film, so it must have the advantage of thickness, quality, flexibility, considers that the OLED thickness only has about 100nm, and therefore thickness and the quality-base of whole indicating meter originally derive from substrate.Use in addition organic materials also to bring an advantage, be exactly time of response fast, this depends on that the radiative transition life-span of OLED material generally only has several nanoseconds to about the 500ns, and this is most suitable for displaying video, especially playing back at high speed picture, this is that liquid-crystal display is beyond one's reach.The OLED technology is as showing that maximum advantage just is its high-level efficiency, if adopt phosphor material, theoretic internal quantum efficiency can reach 100%.And occupy at present the liquid crystal of demonstration field main flow, because the restriction of spectral filter will have 2/3rds backlight losing, the loss of efficient is self-evident.Compare with liquid-crystal display in addition, OLED shows 180 ° that also have active illuminating.The present invention is intended to develop new electroluminescent material, the material that relates to have advantages of be easy to prepare, with low cost, and have preferably electroluminescent properties.
Summary of the invention
The object of the present invention is to provide a class to contain the organic light emission compound (compound 1 – 11) of acridine core, and be applied to prepare in the high performance organic electroluminescence device.
The synthetic route of compound 1-6 is shown below.Compound 1-6 is made of acridine, phenyl phenanthro-imidazoles and amido (dimethyl amine, diphenylamine, xylyl amine or two fourth phenyl amine).Compound 7-11 acridine and hexichol amido or dimethylbenzene amido consist of.The concrete synthesis condition condition of compound 1-11 is seen embodiment.
Compound of the present invention can be used as luminescent layer and prepares electroluminescent device, and the device architecture of employing as shown in Figure 1.Device architecture comprises successively: be attached to ITO on the transparent glass as anode, NPB(N, N'-two (1-naphthyl)-N, N'-phenylbenzene-1,1'-biphenyl-4,4'-diamines) as hole transmission layer, one or more compound compounds of the present invention as luminescent layer, Bebq
2(two (10 hydroxy benzo quinoline) beryllium) as material of main part and electron transfer layer, LiF as electron injecting layer, metal A l as negative electrode.
Hole and electronics inject from anode and negative electrode respectively, transmit in hole transmission layer and electron transfer layer respectively, and finally inject luminescent layer, and wherein a part of hole and electronics are captured pairing mutually, form exciton.Exciton is got back to ground state by radiative transition, just has light to send.These electroluminescent devices can be used for the Application Areass such as lighting source, signal lamp, aplhanumeric visual display, direction board, photoelectronic coupler, flat-panel monitor.By electroluminescent spectrum, brightness, the test of current/voltage characteristic analytical procedure.
Description of drawings
Fig. 1: use material of the present invention preparation the EL device structure schematic diagram;
Fig. 2: the electroluminescent device spectrogram of using compound 1-6 preparation of the present invention.
As shown in Figure 1, each component names is: be attached to ito anode 1, NPB(N on the transparent glass, N'-two (1-naphthyl)-N, N'-phenylbenzene-1,1'-biphenyl-4,4'-diamines) hole transmission layer 2, comprise luminescent layer 3, the Bebq of compound of the present invention
2 Electron transfer layer 4, LiF electron injecting layer 5, metal A l negative electrode 6.
As shown in Figure 2, its characteristic of the electroluminescent device of the compounds of this invention is as follows: compound 1 emission peak position is 532nm, cut-in voltage 2.4V, and high-high brightness is 84340cd/m
2, maximum current efficient is 9.8cd/A, maximum power efficiency is 11.5lm/W; Compound 2 emission peak positions are 532nm, cut-in voltage 2.4V, and high-high brightness is 66040cd/m
2, maximum current efficient is 7.1cd/A, maximum power efficiency is 8.6lm/W; Compound 3 emission peak positions are 544nm, cut-in voltage 2.4V, and high-high brightness is 95605cd/m
2, maximum current efficient is 11.8cd/A, maximum power efficiency is 13.3lm/W; Compound 4 emission peak positions are 564nm, cut-in voltage 2.4V, and high-high brightness is 62480cd/m
2, maximum current efficient is 7.4cd/A, maximum power efficiency is 8.8lm/W.Compound 5 emission peak positions are 508nm, cut-in voltage 2.4V, and high-high brightness is 30950cd/m
2, maximum current efficient is 5.3cd/A, maximum power efficiency is 4.9lm/W.Compound 6 emission peak positions are 512nm, cut-in voltage 2.4V, and high-high brightness is 52930cd/m
2, maximum current efficient is 7.4cd/A, maximum power efficiency is 8.2lm/W.
Embodiment
Embodiment 1: amido phenanthro-imidazoles acridine synthetic
With 3,6-proflavin (slave ladder Xi Ai company buys for 1.04g, 5mmol), phenanthrenequione (0.42g, 2mmol buy from An Naiji company), ammonium acetate (0.62g, 8mmol) and phenyl aldehyde (0.21g, 2mmol) join in the 50ml Glacial acetic acid, at N
2The lower back flow reaction of gas protection 12 hours.Cooling after question response finishes joins in a large amount of water reaction solution and stirring, has a large amount of precipitations to generate.To precipitate suction filtration, filter cake washes with water.Solid separates with column chromatography after dry.The molion quality that mass spectroscopy is determined is: 486.5, and (calculated value is: 486.1); Theoretical constituent content (%) C
34H
22N
4: C, 84.26; H, 4.31; N, 11.25; Actual measurement constituent content (%): C, 83.93; H, 4.56; N, 11.51; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Example 2: compound 1 synthetic:
With amido phenanthro-imidazoles acridine (360mg, 0.74mmol), cesium carbonate (962mg, 2.96mmol), cuprous iodide (24mg, 0.062mmol) phenanthroline (48mg, 0.124mmol) is in the 50ml bottle with two necks, behind the nitrogen replacement from injecting methyl iodide (420mg, 2.96mmol) and 10ml DMF.Refluxed three days.Question response is poured reaction solution in a large amount of water into after finishing, and filters, and the filter cake silica gel column chromatography is obtained product.The molion quality that mass spectroscopy is determined is: 514.1, and (calculated value is: 514.2); Theoretical constituent content (%) C
36H
28N
4: C, 84.02; H, 5.09; N, 10.89; Actual measurement constituent content (%): C, 83.72; H, 5.26; N, 10.90; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Embodiment 3: compound 2 synthetic:
With amido phenanthro-imidazoles acridine (360mg, 0.74mmol), cesium carbonate (962mg, 2.96mmol), cuprous iodide (24mg, 0.062mmol) phenanthroline (48mg, 0.124mmol) in the 50ml bottle with two necks, behind the nitrogen replacement from injecting iodobenzene (603mg, 2.96mmol) and 10ml DMF.Refluxed three days.Question response is poured reaction solution in a large amount of water into after finishing, and filters, and the filter cake silica gel column chromatography is obtained product.The molion quality that mass spectroscopy is determined is: 638.1, and (calculated value is: 638.3); Theoretical constituent content (%) C
46H
32N
4: C, 86.49; H, 4.73; N, 8.77; Actual measurement constituent content (%): C, 86.03; H, 4.82; N, 9.01; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Embodiment 4: compound 3 synthetic:
With amido phenanthro-imidazoles acridine (360mg, 0.74mmol), cesium carbonate (962mg, 2.96mmol), cuprous iodide (24mg, 0.062mmol) phenanthroline (48mg, 0.124mmol) is in the 50ml bottle with two necks, behind the nitrogen replacement from injecting methyl iodobenzene (645mg, 2.96mmol) and 10ml DMF.Refluxed three days.Question response is poured reaction solution in a large amount of water into after finishing, and filters, and the filter cake silica gel column chromatography is obtained product.The molion quality that mass spectroscopy is determined is: 666.1, and (calculated value is: 666.3); Theoretical constituent content (%) C
49H
36N
4: C, 86.46; H, 5.14; N, 8.40; Actual measurement constituent content (%): C, 86.81; H, 4.98; N, 8.00; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Embodiment 5: compound 6 synthetic:
With amido phenanthro-imidazoles acridine (360mg, 0.74mmol), cesium carbonate (962mg, 2.96mmol), cuprous iodide (24mg, 0.062mmol) phenanthroline (48mg, 0.124mmol) is in the 50ml bottle with two necks, behind the nitrogen replacement from injecting butyl iodobenzene (820mg, 2.96mmol) and 10ml DMF.Refluxed three days.Question response is poured reaction solution in a large amount of water into after finishing, and filters, and the filter cake silica gel column chromatography is obtained product.The molion quality that mass spectroscopy is determined is: 750.0, and (calculated value is: 750.4); Theoretical constituent content (%) C
54H
48N
4: C, 86.37; H, 6.17; N, 7.46; Actual measurement constituent content (%): C, 86.26; H, 6.24; N, 7.07; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Embodiment 6: compound 7 synthetic:
Get 3,6-proflavin (155mg, 0.74mmol), cesium carbonate (962mg, 2.96mmol), cuprous iodide (24mg, 0.062mmol) and phenanthroline (48mg, 0.124mmol) in the 50ml bottle with two necks, inject iodobenzene (603mg behind the nitrogen replacement, 2.96mmol) and 10ml DMF, refluxed three days.Question response is poured reaction solution in a large amount of water into after finishing, and filters, and the filter cake silica gel column chromatography is obtained product.Nucleus magnetic hydrogen spectrum
1H NMR (300MHz, DMSO, ppm): δ 8.71 (s, 1H), 7.91 (d, J=9.3Hz, 2H), 7.43-7.38 (m, 8H), 7.22-7.12 (m, 14H), 7.04 (d, J=2.1Hz, 2H).The molion quality that mass spectroscopy is determined is: 513.1, and (calculated value is: 513.2); Theoretical constituent content (%) C
37H
27N
3: C, 86.52; H, 5.30; N, 8.18; Actual measurement constituent content (%): C, 86.84; H, 5.09; N, 8.06; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Embodiment 7: compound 8 synthetic:
Get 3,6-proflavin (155mg, 0.74mmol), cesium carbonate (962mg, 2.96mmol), cuprous iodide (24mg, 0.062mmol) and phenanthroline (48mg, 0.124mmol) in the 50ml bottle with two necks, inject behind the nitrogen replacement methyl iodobenzene (645mg, 2.96mmol) and 10ml DMF, refluxed three days.Question response is poured reaction solution in a large amount of water into after finishing, and filters, and the filter cake silica gel column chromatography is obtained product.The molion quality that mass spectroscopy is determined is: 569.1, and (calculated value is: 569.3); Theoretical constituent content (%) C
41H
35N
3: C, 86.43; H, 6.19; N, 7.38; Actual measurement constituent content (%): C, 86.83; H, 6.05; N, 7.29; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Embodiment 8: compound 11 synthetic:
Get 3,6-proflavin (155mg, 0.74mmol), cesium carbonate (962mg, 2.96mmol), cuprous iodide (24mg, 0.062mmol) and phenanthroline (48mg, 0.124mmol) in the 50ml bottle with two necks, inject behind the nitrogen replacement butyl iodobenzene (820mg, 2.96mmol) and 10ml DMF, refluxed three days.Question response is poured reaction solution in a large amount of water into after finishing, and filters, and the filter cake silica gel column chromatography is obtained product.The molion quality that mass spectroscopy is determined is: 737.3, and (calculated value is: 737.0); Theoretical constituent content (%) C
53H
59N
3: C, 86.29; H, 8.01; N, 5.70; Actual measurement constituent content (%): C, 86.67; H, 8.05; N, 5.62; Above-mentioned analytical results shows, the product of the product of acquisition for estimating.
Embodiment 9: luminescent device [ITO/NPB/Bebq2: compound 1=3%/Bebq2/LiF/Al]
Evaporation hole transmission layer NPB(thickness is being coated with on the glass substrate of ito anode successively
), the compound 1 of luminescent layer embodiment 1 preparation is as doping agent, Bebq
2As material of main part
Electron transfer layer Bebq
2 Electron injection material LiF
The Al negative electrode
Keeping pressure in evaporate process is 5 * 10
-6Pa.This device emission peak position is 532nm, cut-in voltage 2.4V, and high-high brightness is 84340cd/m
2, maximum current efficient is 9.8cd/A, maximum power efficiency is 11.5lm/W.
Embodiment 10: luminescent device [ITO/NPB/Bebq
2: compound 2=5%/Bebq
2/ LiF/Al] evaporation hole transmission layer NPB(thickness is being coated with on the glass substrate of ito anode successively
), the compound 2 of luminescent layer embodiment 2 preparations is as doping agent, Bebq
2As material of main part
Electron transfer layer Bebq
2 
Electron injection material LiF
The Al negative electrode
Keeping pressure in evaporate process is 5 * 10
-6Pa.This device emission peak position is 532nm, cut-in voltage 2.4V, and high-high brightness is 66040cd/m
2, maximum current efficient is 7.1cd/A, maximum power efficiency is 8.6lm/W.
Embodiment 11: luminescent device [ITO/NPB/Bebq
2: compound 3=3%/Bebq
2/ LiF/Al] evaporation hole transmission layer NPB(thickness is being coated with on the glass substrate of ito anode successively
), the compound 3 of luminescent layer embodiment 3 preparations is as doping agent, Bebq
2As material of main part
Electron transfer layer Bebq
2 
Electron injection material LiF
The Al negative electrode
Keeping pressure in evaporate process is 5 * 10
-6Pa.This device emission peak position is 544nm, cut-in voltage 2.4V, and high-high brightness is 95605cd/m
2, maximum current efficient is 11.8cd/A, maximum power efficiency is 13.3lm/W.
Embodiment 12: luminescent device [ITO/NPB/Bebq
2: compound 6=5%/Bebq
2/ LiF/Al] evaporation hole transmission layer NPB(thickness is being coated with on the glass substrate of ito anode successively
), the compound 6 of luminescent layer embodiment 4 preparations is as doping agent, Bebq
2As material of main part
Electron transfer layer Bebq
2 
Electron injection material LiF
The Al negative electrode
Keeping pressure in evaporate process is 5 * 10
-6Pa.This device emission peak position is 564nm, cut-in voltage 2.4V, and high-high brightness is 62480cd/m
2, maximum current efficient is 7.4cd/A, maximum power efficiency is 8.8lm/W.
Embodiment 13: luminescent device [ITO/NPB/Bebq
2: compound 7=5%/Bebq
2/ LiF/Al] evaporation hole transmission layer NPB(thickness is being coated with on the glass substrate of ito anode successively
), the compound 7 of luminescent layer embodiment 5 preparations is as doping agent, Bebq
2As material of main part
Electron transfer layer Bebq
2 
Electron injection material LiF
The Al negative electrode
Keeping pressure in evaporate process is 5 * 10
-6Pa.This device emission peak position is 508nm, cut-in voltage 2.4V, and high-high brightness is 30950cd/m2, and maximum current efficient is 5.3cd/A, and maximum power efficiency is 4.9lm/W.
Embodiment 14: luminescent device [ITO/NPB/Bebq
2: compound 8=5%/Bebq
2/ LiF/Al] evaporation hole transmission layer NPB(thickness is being coated with on the glass substrate of ito anode successively
), the compound 8 of luminescent layer embodiment 6 preparations is as doping agent, Bebq
2As material of main part
Electron transfer layer Bebq
2 
Electron injection material LiF
The Al negative electrode
Keeping pressure in evaporate process is 5 * 10
-6Pa.This device emission peak position is 512nm, cut-in voltage 2.4V, and high-high brightness is 52930cd/m
2, maximum current efficient is 7.4cd/A, maximum power efficiency is 8.2lm/W.
Claims (4)
1. contain the organic light emission compound of acridine core, its structural formula is as follows:
Wherein, R'=H, R'=CH
3, R'=CH
2CH
3,
R'=(CH
2)
2CH
3Or R'=(CH
2)
3CH
3
2. the application of organic light emission compound in the preparation electroluminescent device that contains the acridine core claimed in claim 1.
3. the application of organic light emission compound in the preparation electroluminescent device that contains the acridine core as claimed in claim 2 is characterized in that: as the luminescent layer of electroluminescent device.
4. contain as claimed in claim 2 or claim 3 the application of organic light emission compound in the preparation electroluminescent device of acridine core, it is characterized in that: for the preparation of lighting source, signal lamp, aplhanumeric visual display, direction board, photoelectronic coupler or flat-panel monitor.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650032A (en) * | 2015-01-23 | 2015-05-27 | 北京鼎材科技有限公司 | Acridine derivatives, and preparation method and application thereof |
| CN104693174A (en) * | 2015-01-23 | 2015-06-10 | 北京鼎材科技有限公司 | Benzacridine derivative as well as preparation method and application thereof |
| CN107311926A (en) * | 2017-07-13 | 2017-11-03 | 长春海谱润斯科技有限公司 | A kind of acridine compound and its organic luminescent device |
| CN107482132A (en) * | 2017-08-22 | 2017-12-15 | 长春海谱润斯科技有限公司 | A kind of organic luminescent device |
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| CN102443004A (en) * | 2011-11-01 | 2012-05-09 | 南京工业大学 | Organic luminescent material 6,7,14,15-tetrahydro-5,13-disubstituted benzene [1,2-c:4,5-c']bis-acridine compound, its synthesis method and its application |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104650032A (en) * | 2015-01-23 | 2015-05-27 | 北京鼎材科技有限公司 | Acridine derivatives, and preparation method and application thereof |
| CN104693174A (en) * | 2015-01-23 | 2015-06-10 | 北京鼎材科技有限公司 | Benzacridine derivative as well as preparation method and application thereof |
| CN104693174B (en) * | 2015-01-23 | 2017-01-04 | 北京鼎材科技有限公司 | Benzacridine derivant, its preparation method and application thereof |
| CN107311926A (en) * | 2017-07-13 | 2017-11-03 | 长春海谱润斯科技有限公司 | A kind of acridine compound and its organic luminescent device |
| CN107482132A (en) * | 2017-08-22 | 2017-12-15 | 长春海谱润斯科技有限公司 | A kind of organic luminescent device |
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| CN102924431B (en) | 2014-05-07 |
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