CN1477175A - Beta-diketone ligand and its europium coordination compound and europium coordinationi compound electroluminescence device - Google Patents
Beta-diketone ligand and its europium coordination compound and europium coordinationi compound electroluminescence device Download PDFInfo
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Abstract
The present invention relates to a beta-diketone ligand and its europium coordination compound and europium coordination compound electroluminescent device. The ligand is the transmission group with carrier, for example, beta-diketone ligand of carbazyl or oxazolyl, and the chemical formula of europium coordination compound is Eu(DBM)n(R-DBM)3-nBath, n=1.2, Bath=4,7-diphenyl-1,10-o-phenan-throline. The electroluminescent device includes conductive glass substrate layer, hole transmission layer, luminous layer and cathode layer, and the luminous material of luminous layer adopts the above-mentioned europium coordination compound.
Description
Technical field:
The present invention relates to field of organic electroluminescent materials, relate in particular to a kind of rare earth elements europium complex luminescent material.
Technical background:
At present, the used color monitor of people mostly is cathode tube or liquid-crystal display, the former volume is big, response speed is slow, efficient is low, the latter compares volume-diminished with the former, can realize flat pannel display, but, still can not satisfy people's needs because of it is that passive type light source, visual angle are little, low-response, complex process.
1987, the C.W.Tang of U.S. Eastman Kodak company and VanSlyke (Appl.Phys.Lett.1987,51,913) made initiative research to organic electroluminescent.They are clipped in double-deck organic membrane and have made organic electroluminescence device (OLED) between two electrodes.Since then, organic electroluminescent becomes the research focus in luminous field.Organic electroluminescent exists huge magnetism to be that it has following characteristics:
1) adopt organism, the material range of choice is wide, can realize the demonstration of any color from the blue light to ruddiness;
2) driving voltage is low, only needs the volts DS of 3-10 volt;
3) luminosity and luminous efficiency height;
4) full solidified active illuminating;
5) visual angle is wide, and response speed is fast;
6) preparation process is simple, and expense is low;
7) ultrathin membrane, in light weight;
8) can be produced on the softish substrate, device is expected bending fold.
Common electroluminescent organic material can be divided into polymkeric substance and small molecule material.The general broad of these material luminescent spectrum scopes is difficult to satisfy the requirement of actual displayed to purity of color.Because be subjected to the central ion of part perturbation luminous luminous the belonging to of rare earth compounding (the especially title complex of europium and terbium), emission wavelength depends on metal ion, glow peak is sharp-pointed narrow band, its luminous mechanism is to be excited to singlet state after part absorbs energy, give excited triplet state with transmission ofenergy more through leaping up between system then, give central ion by excited triplet state with transmission ofenergy again, it is excited, the radiative transition process of rare earth central ion excited state to ground state takes place at last.Compare with other organic molecules, it is narrow that rare earth compounding has emission band, the purity of color height, and modified ligand does not influence the emmission spectrum of central ion.In addition, rare earth compounding is used for the do not spinned restriction of choosing rule of electroluminescent, and its internal quantum efficiency can reach 100% in theory.These unique advantages make it become one of the research focus in electroluminescent field.
The title complex of europium is a red illuminating material, and 1991, people such as Japanese Kido utilized rare-earth europium title complex Eu (TTA) first
32H
2O has realized the emitting red light of narrow band as the luminescent materials organic electroluminescence device.After this, people study multiple europium complex material.Up to now, the europium complex electroluminescent device high-high brightness of bibliographical information is 1670cd/m
2, luminous efficiency is 2.1lm/W (P.P.Sun, J.P.Duan, H.T.Shih, C.H.Cheng, Appl.ehys.Lett.2002,81,792.), and be to have utilized adulterating method prepared, be about to europium complex and mix up in having the material of carrier transmission performance as luminescent layer.
It is generally acknowledged that good electroluminescent material should possess excellent photoluminescence performance, carrier transmission performance, thermal stability and film forming properties etc.Therefore, synthetic europium complex with These characteristics just becomes the key that improves its electroluminescent properties.We have invented the europium complex electroluminescent material with These characteristics, and have been made into device on working foundation for many years, and the high-high brightness of the made device of some europium complex electroluminescent material reaches 2797cd/m
2, luminous efficiency 32lm/W.
Summary of the invention:
The object of the present invention is to provide the rare-earth europium complex luminescent material of a kind of brightness height, excellent in efficiency, and the part of this europium complex and the electroluminescent device that adopts this europium complex as luminescent material.
Europium complex part of the present invention is a beta-diketonate ligand, has carrier transport group, and general structure is
R is a carrier transport group in the formula, is selected from carbazyl or oxazolyl; R
1Be linker, be selected from alkyl or alkoxyl group, n=0,1; DBM=diphenylpropane-1,3-dione(DPPO) negatively charged ion ,-HDBM=diphenylpropane-1,3-dione(DPPO) base.
Described carrier transport group can be carbazole group, and this ligand structure formula is as follows, notes by abridging to be c-HDBM:
Also can be the oxazole group, this ligand structure formula is as follows, notes by abridging to be o-HDBM:
Europium complex of the present invention, chemical formula are Eu (DBM)
n(R-DBM)
3-nBath, n=1,2, Bath=4,7-phenylbenzene-1,10-Phenathroline.
Described R-DBM is selected from c-DBM, o-DBM.
Europium complex of the present invention can be Eu (DBM)
2(c-DBM) Bath:
Also can be (c-DBM) (o-DBM) Bath of Eu (DBM):
Electroluminescent device of the present invention comprises the Conducting Glass layer, hole transmission layer, and luminescent layer, cathode layer, the luminescent material chemical formula of luminescent layer are Eu (DBM)
n(R-DBM)
3-nBath, n=1,2.
Above-mentioned device also can comprise hole blocking layer and electron transfer layer.
Above-mentioned luminescent material chemical formula can be Eu (DBM)
2(c-DBM) (c-DBM) (o-DBM) Bath of Bath and/or Eu (DBM).
Beta-diketonate ligand of the present invention is compared with disclosing part, and by introducing carrier transport groups such as carbazole or oxazole group, the title complex that itself and europium are formed has hole and electron transport ability simultaneously, has improved the brightness and the efficient of device.
Europium complex of the present invention has excellent electroluminescent properties, can be used as electroluminescent material, makes luminescent layer in electroluminescent device.
The inventor has found to have higher photoluminescence efficiency and can produce high efficiency electroluminous red europium complex.The electroluminescent properties of these title complexs is better than disclosed europium complex Eu (TTA)
3DPPZ (P.P.Sun, J.P.Duan, H.T.Shih, C.H.Cheng, Appl.Phys.Lett.2002,81,792).Maximum brightness can reach every square metre of 2797 Kan Tela, and maximum power efficiency can reach every watt of 32 lumen, you can well imagine high 1.8 and 15 times than the highest disclosed numerical value 1600 every square metre of Kan Tela and the every watt-minute of 2.1 lumens.
Description of drawings:
Fig. 1 electroluminescent device structural representation of the present invention
The emmission spectrum of Fig. 2 electroluminescent device of the present invention
Embodiment:
Below by specific embodiment product of the present invention and method are further described, but the protection domain that these specific embodiments do not limit the present invention in any way.
The present embodiment is raw materials used to be known compound, can buy on market, or available methods known in the art is synthetic.
1: part 4-(carbazyl-9) diphenylpropane-1,3-dione(DPPO) (c-HDBM) synthetic
A. synthetic to carbazyl benzene nitrile: (16.7g is 0.100mol) with (12.1g 0.100mol) is dissolved in the inferior maple of 100mL diformazan, in anhydrous K to equimolar carbazole to fluorobenzonitrile
2CO
3(41.4g, 0.300mol) the following 140 ℃ of reaction 12h of catalysis pour mixture in the 1L water into then, obtain gray solid.Crude product is with methylene dichloride: sherwood oil (1: 3) is an eluent, separate with silicagel column and purify, white solid, yield 60%.
1H?NMR(inCD
3Cl)，8.15～8.13(d，2H)，7.91～7.88(d，2H)，7.75～7.72(q，2H)，7.47～7.41(m，4H)，7.35～7.31(m，2H).
B. synthetic to the carbazyl ethyl benzoate: in 50mL ethanol, add 3g to carbazyl benzene nitrile, stir and slowly drip the 15mL vitriol oil down, return heat up in a steamer 72h after, mixture is poured in the 500mL frozen water, filter crude product, with methylene dichloride: sherwood oil (1: 2) is an eluent, separates with silicagel column and purifies, get white solid, yield 72%.
1H?NMR(in?CD
3Cl)，8.30～8.28(d，2H)，8.15～8.13(d，2H)，7.68～7.66(q，2H)，7.48～7.40(m，4H)，7.33～7.29(m，2H)，4.78～4.42(q，2H)，1.56～1.43(t，2H).
C.4-(carbazyl-9) diphenylpropane-1,3-dione(DPPO) is synthetic: heat up in a steamer 48h equimolar carbazyl ethyl benzoate and methyl phenyl ketone are returned under the NaH catalysis in anhydrous dimethyl benzene, use the dilute hydrochloric acid acidifying then, organic phase be spin-dried for a yellow solid.With methylene dichloride: sherwood oil (1: 1) is an eluent, separate with silicagel column and purify, yellow solid, yield 42%.
1H?NMR(in?CD
3Cl)，
1H?NMR(in?CD
3Cl)，16.93(s，1H)，8.23～8.21(d，2H)，8.15～8.14(d，2H)，8.03～8.02(d，2H)，7.73～7.71(d，2H)，7.58～7.57(q，1H)，7.56
2: part 4-[(5-phenyl-1,3,4-oxadiazoles base)-2] diphenylpropane-1,3-dione(DPPO) (o-HDBM) is synthetic
A. synthetic to the tetrazyl ethyl benzoate: paracyanobenzoic acid ethyl ester (5.2g, 30mmol), sodiumazide (2.93g, 45mmol) and ammonium chloride (2.4g, 45mmol) the mixed liquid that is dissolved in the 30mL dimethyl formamide is poured in the 400mL water after 100 ℃ of reaction 24h. cooling, the dilute hydrochloric acid acidifying, filter white solid.Productive rate 72%.
1H NMR (in CD
3Cl), 8.26～8.24 (d, 2H), 8.22～8.20 (d, 2H), 4.47～4.41 (q, 2H), 1.45～1.42 (t, 3H).
B.2-phenyl-5-synthetic to the group-4 ethyl formate phenyltetrazole: under the nitrogen atmosphere, (3.0g, (4.36g in 25mL pyridine solution 20mmol), returns and heats up in a steamer 2h 22mmol) slowly to be added drop-wise to the tetrazyl ethyl benzoate with Benzoyl chloride.After the cooling, add 200mL water, separate out precipitation, filter white solid, productive rate 90%.
1H NMR (in CD
3Cl), 8.22～8.16 (m, 4H), 8.16～8.15 (d, 2H), 7.59～7.55 (m, 3H), 4.46～4.41 (q, 2H), 1.46～1.42 (t, 3H).
C.4-[(5-phenyl-1,3,4-oxadiazoles base)-2] diphenylpropane-1,3-dione(DPPO) is synthetic: the similar c-HDBM of synthetic method, productive rate 56%.
1H NMR (in CD
3Cl), 17.12 (s, 1H), 8.43～8.41 (d, 2H), 8.33～8.31 (d, 2H), 8.24～8.18 (m, 4H), 7.71～7.59 (m, 6H), 7.50 (s, 1H).
Europium [Eu (DBM) is closed in 3: two (diphenylpropane-1,3-dione(DPPO) negatively charged ion) [4-(carbazyl-9) diphenylpropane-1,3-dione(DPPO) negatively charged ion] (4,7-phenylbenzene Phenathroline)
2(c-DBM) Bath] synthetic
HDBM (0.444g, 2.00mmol), c-HDBM (0.389g, 1.00mmol), 4,7-phenylbenzene Phenathroline (0.332g, 1.00mol) and NaOH (0.12g, 3.00mol) 50mL ethanolic soln stirs the EuCl that slowly adds 10mL down
36H
2O (0.366g, 1.00mol) ethanolic soln.Return heat up in a steamer 2h after, filter, yellow solid.Crude product ethanol and tetrahydrofuran (THF) mixed solution recrystallization.Productive rate 86%.Determination of elemental analysis value: C, 73.40; H, 4.25; N.3.16.C
81H
56N
3O
6Eu calculated value: C, 73.75; H, 4.30; N, 3.19.
4:(diphenylpropane-1,3-dione(DPPO) negatively charged ion) [4-(carbazyl-9) diphenylpropane-1,3-dione(DPPO) negatively charged ion] { 4-[(5-phenyl-1,3,4-oxadiazoles base)-2] diphenylpropane-1,3-dione(DPPO) negatively charged ion } (4,7-phenylbenzene Phenathroline) close the synthetic of europium [Eu (DBM) is (o-DBM) Bath (c-DBM)]
HDBM (0.222g, 1.00mmol), c-HDBM (0.389g, 1.00mmol), o-HDBM (0.366g, 1.00mmol), 4,7-phenylbenzene-1.10-Phenathroline (0.332g, 1.00mol) and NaOH (0.12g, 3.00mol) 50mL ethanolic soln stirs the EuCl that slowly adds 10mL down
36H
2O (0.366g, 1.00mol) ethanolic soln.Return heat up in a steamer 2h after, filter, yellow solid.Crude product ethanol and tetrahydrofuran (THF) mixed solution recrystallization, productive rate 86%.Determination of elemental analysis value: C, 73.17; H, 4.19; N, 4.96.C
89H
58N
5O
7Eu calculated value: C, 73.14; H, 4.00; N, 4.79.
5: the making of device
The new europium complex of the present invention can comprise conductive glass (ITO) substrate layer, hole transmission layer N as the device of luminescent layer, N '-phenylbenzene-N, N '-two (3-aminomethyl phenyl)-1,1 '-phenylbenzene-4,4 '-diamines (TPD), luminescent layer europium complex, hole blocking layer 2,9-dimethyl-4,7-phenylbenzene-1,10-Fei Luolin (BCP), electron transfer layer oxine aluminium (AlQ) or 2-(4-xenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazoles (PBD), cathode layer.
Electroluminescent device can be made by methods known in the art, as presses reference (Appl.Phys.Lett.1987,51,913) disclosed method and make.Concrete grammar is: in high vacuum (less than 8 * 10
-4Pa) under the condition, on through conductive glass (ITO) substrate that cleans, deposit hole mobile material, luminescent material, hole barrier materials, electron transport material and cathode material successively.
Ito glass sheet (21 * 21mm
2), remove 1/3rd ITO with concentrated hydrochloric acid corrosion, with its with washing composition and organic solvent ultrasonic cleaning clean after, oven dry places in the vacuum plating unit,＜8 * 10
-4Under the high vacuum condition of Pa, monitor the thickness of each layer with quartz resonator, with title complex, hole barrier materials, electron transport material and the metallic cathode [magnesium silver alloys (Mg of hole mobile material, europium
0.9Ag
0.1)] deposit on the conductive glass successively.The thickness of each organic layer can change, so that device sends the feature ruddiness of title complex.
Make four-layer device as Fig. 1 with this method, the structure of the various devices that make is as follows:
Device one: ITO/TPD/Eu (DBM)
2(c-DBM) Bath/BCP/ALQ/Mg
0.9Ag
0.1/ Ag
Device two: ITO/TPD/Eu (DBM)
2(c-DBM) Bath:PBD/PBD/Mg
0.9Ag
0.1/ Ag
Device three: ITO/TPD/Eu (DBM)
2(c-DBM) Bath:PBD/PBD/ALQ/Mg
0.9Ag
0.1/ Ag
When measuring element performance and electroluminescent spectrum, the ITO electrode always links to each other with positive pole.The mensuration of electroluminescent spectrum is on PR650 spectrograph or Hitachi F4500 fluorescence spectrophotometer, apply a constant voltage (usually 3-30 volt between) to device in, write down its emmission spectrum (see figure 2).
Voltage-to-current (I-V) curve and voltage-brightness (L-V) curve are by measuring on the computer-controlled Keithley 2400Sourcemeter Unit, and brightness is corrected by silicon photoelectric diode.(see figure 2)
The performance data of device-～three sees the following form:
Maximum brightness maximum power efficient
Device glow color luminescent spectrum
Kan Tela/every square metre of lumens/watt
Device one 1,948 0.54 redness are seen Fig. 2
Device 2 2,019 32 redness are seen Fig. 2
Device 3 2,797 9.4 redness are seen Fig. 2
Document maximum 1,670 2.1 redness
The ownership system gets the feature redness that device all sends the europium of narrow band.Device one and document Appl.Phys.Lett.2002,81,792. compare, and do not adopt doping techniques, make the device high-high brightness reach every square metre of 1948 Kan Tela.And after being entrained in europium complex among the PBD, resulting device two efficient significantly improve, and are 15 times of document maximum.Device three is introduced oxine aluminium (AlQ) layer, has improved the injectability of electronics, and the high-high brightness that makes device is up to every square metre of 2797 Kan Tela, and efficient also is more than 4 times of literature value.Therefore, compare with other europium complex electroluminescent material and device, the present invention has higher brightness and better electroluminescent efficiency, and the high-high brightness of the electroluminescent device of gained of the present invention and efficient are the highest in the present europium complex electroluminescent device.
Claims (9)
1, a kind of beta-diketonate ligand has carrier transport group, and general structure is
R is a carrier transport group in the formula; R
1Be linker, be selected from alkyl or alkoxyl group, n=0,1; DBM=diphenylpropane-1,3-dione(DPPO) negatively charged ion ,-HDBM=diphenylpropane-1,3-dione(DPPO) base.
2, beta-diketonate ligand as claimed in claim 1 is characterized in that described carrier transport group is a carbazole group, and this ligand structure formula is c-HDBM.
3, beta-diketonate ligand as claimed in claim 1 is characterized in that described carrier transport group is the oxazole group, and this ligand structure formula is o-HDBM.
4, a kind of europium complex of beta-diketonate ligand, chemical formula are Eu (DBM)
n(R-DBM)
3-nBath, n=1,2, R is a carrier transport group, Bath=4,7-phenylbenzene-1,10-Phenathroline.
5, the europium complex of beta-diketonate ligand as claimed in claim 4 is characterized in that described R-DBM is selected from c-DBM, o-DBM.
6, a kind of europium complex electroluminescent device comprises the Conducting Glass layer, hole transmission layer, and luminescent layer, cathode layer, the luminescent material chemical formula that it is characterized in that luminescent layer are Eu (DBM)
n(R-DBM)
3-nBath, n=1,2.
7, europium complex electroluminescent device as claimed in claim 6 is characterized in that this device also comprises hole blocking layer and electron transfer layer.
8,, it is characterized in that described luminescent material chemical formula is Eu (DBM) as claim 6 or 7 described europium complex electroluminescent devices
2(c-DBM) Bath.
9,, it is characterized in that described luminescent material chemical formula is (c-DBM) (o-DBM) Bath of Eu (DBM) as claim 6 or 7 described europium complex electroluminescent devices.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100412074C (en) * | 2005-04-21 | 2008-08-20 | 北京大学 | Oxadiazole derivative containing carbazolyl and its electroluminescent device |
| CN100439368C (en) * | 2006-11-09 | 2008-12-03 | 湘潭大学 | Organic eurepium compound based on functional o-phenan throline ligand and its electroluminous device |
| CN100467462C (en) * | 2006-03-31 | 2009-03-11 | 北京大学 | Terdentate ligand contg. heteroaryl pyrazole, its Eu complex and electroluminescent element |
| US7517596B2 (en) * | 2004-11-29 | 2009-04-14 | Canon Kabushiki Kaisha | Phenanthroline compound and light-emitting device |
| CN101066975B (en) * | 2007-06-15 | 2010-06-02 | 北京大学 | Europium complex with visible light sensitized light emitting performance and its synthesis process |
| CN102002062A (en) * | 2010-09-26 | 2011-04-06 | 中科院广州化学有限公司 | Polynuclear rare earth organic complex, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7517596B2 (en) * | 2004-11-29 | 2009-04-14 | Canon Kabushiki Kaisha | Phenanthroline compound and light-emitting device |
| CN100412074C (en) * | 2005-04-21 | 2008-08-20 | 北京大学 | Oxadiazole derivative containing carbazolyl and its electroluminescent device |
| CN100467462C (en) * | 2006-03-31 | 2009-03-11 | 北京大学 | Terdentate ligand contg. heteroaryl pyrazole, its Eu complex and electroluminescent element |
| CN100439368C (en) * | 2006-11-09 | 2008-12-03 | 湘潭大学 | Organic eurepium compound based on functional o-phenan throline ligand and its electroluminous device |
| CN101066975B (en) * | 2007-06-15 | 2010-06-02 | 北京大学 | Europium complex with visible light sensitized light emitting performance and its synthesis process |
| CN102002062A (en) * | 2010-09-26 | 2011-04-06 | 中科院广州化学有限公司 | Polynuclear rare earth organic complex, and preparation method and application thereof |
| CN102093398A (en) * | 2011-01-24 | 2011-06-15 | 安徽大学 | Rare earth compound two-photon absorption material and preparation method thereof |
| CN102093398B (en) * | 2011-01-24 | 2012-07-18 | 安徽大学 | Rare earth compound two-photon absorption material and preparation method thereof |
| CN107434893A (en) * | 2017-07-21 | 2017-12-05 | 广西柳城县成霖农业科技有限公司 | It is a kind of that there is the agricultural film improved through light quality |
| CN110408383A (en) * | 2018-04-28 | 2019-11-05 | 香港科技大学深圳研究院 | With distortion to pure organic room temperature phosphorimetry material and its preparation method and application of-receptor structure |
| CN110408383B (en) * | 2018-04-28 | 2023-01-10 | 香港科技大学深圳研究院 | Pure organic room temperature phosphorescent material with twisted donor-acceptor structure and preparation method and application thereof |
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