CN103086950A - Carbazolyl-based organic electroluminescence compound - Google Patents
Carbazolyl-based organic electroluminescence compound Download PDFInfo
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Abstract
The invention discloses a carbazolyl-based organic electroluminescence compound which has the structural general formula shown by formula (I), wherein R is H, CH3 or CH2CH3. The organic electroluminescence compound disclosed by the invention is used as phosphorescent host material in an organic electrophosphorescent device, and has good electronic transmission characteristic and thermal stability; and meanwhile, the host material has relatively high triplet state energy level and can effectively prevent back transfer of triplet state energy so as to improve the luminous efficiency and prolong the service life of the organic electrophosphorescent device.
Description
Technical field
The invention belongs to the electroluminescent organic material technical field, relate to a kind of electroluminescent organic material based on carbazyl.The invention still further relates to the organic electroluminescence device that uses this compound to make.
Background technology
Organic phosphorescent electroluminescence device (PhOLED:Phosphorescent organic-light emitting device) can be caught triplet state and singlet exciton simultaneously, therefore its internal quantum efficiency has been broken the theoretical limit of conventional fluorescent OLED 25%, make 100% internal quantum efficiency become possibility.In PhOLED, due to guest materials---the quenching effect of phosphorescent light-emitting materials can only be entrained in material of main part as luminescent layer.Compare with other material, the shortage of mazarine phosphorescent light body material has seriously restricted the development of OLED, becomes the bottleneck that OLED realizes industrialization, demands developing high efficiency blue phosphorescent material of main part urgently.
Cause the reason of this situation to mainly contain: the triplet of blue phosphorescent material of main part is not high enough on the one hand, causes object to arrive the energy passback of main body, thereby has reduced the luminous efficiency of device; The carrier transmission performance of mazarine phosphorescent light body material is not good on the other hand, and electronics and hole-recombination probability are reduced, and device efficiency descends.
The material of main part that is applied to organic electro phosphorescent device should have following character: (1) possesses good charge transmission; (2) have energy level coupling preferably between Subjective and Objective, general requirement main body energy gap effectively is transferred to exciton energy and launches phosphorescence on guest molecule greater than the object energy gap, perhaps electric charge directly is trapped in and forms exciton attenuation emission phosphorescence on object; (3) usually must possess certain phosphorescent characteristics, the phosphorescence peak wavelength of its phosphorescence peak value wavelength ratio object phosphor material is short at low temperatures, namely requires material of main part triplet (T
1) greater than object T
1Energy level, and have long phosphorescent lifetime.Wherein, the level structure of material of main part and guest materials coupling is the key factor of restriction device luminous efficiency.
In order to guarantee energy level coupling and to prevent that main body to the triplet excitons quencher of phosphorescence object, selecting the luminescent material of broad stopband as material of main part usually.The carbazole derivative class is present small molecules material of main part with the most use.The existence of lone-pair electron on the N atom in carbazole group makes the triplet state of this class material and the exchange energy between singlet usually very little, thus triplet state and singlet energy level difference few, cause higher triplet.Higher triplet, highly beneficial to the doping of phosphor material, can effectively triplet excitons be limited on phosphor material, prevent that triplet energy state runs off, its T
1Energy level is higher than the T of organic phosphorescent light-emitting materials
1Energy level is realized the phosphorescent emissions of its triplet state.
Summary of the invention
The purpose of this invention is to provide a kind of organic electroluminescent compounds based on carbazyl, this compound has good electronic transmission performance, can be used as a kind of phosphorescent light body material.
For achieving the above object, the organic electroluminescent compounds based on carbazyl provided by the invention has the general structure of formula (I) expression:
In formula: R is H, CH
3Or CH
2CH
3
The organic electroluminescent compounds of above-mentioned general formula (I) expression can be abbreviated as XCP.
Wherein, be respectively H, CH as R
3Or CH
2CH
3The time, corresponding organic electroluminescent compounds is abbreviated as respectively hCP, mhCP and ehCP.
Carbazole derivative and 1,6-dibromo-hexane that organic electroluminescent compounds of the present invention can be represented by the general formula (II) of stoichiometric ratio prepare with the method that following equation represents:
In formula: the definition of R is the same.
The concrete preparation method of organic electroluminescent compounds of the present invention is: with the carbazole derivative and 1 of the general formula (II) of stoichiometric ratio expression; the 6-dibromo-hexane is dissolved in tetrahydrofuran solvent; under nitrogen protection and the existence of Tetrabutyl amonium bromide catalyzer; add the alkali hydroxide soln back flow reaction, obtain the compounds X CP of general formula (I) expression.
Wherein, the preferred potassium hydroxide of described alkali metal hydroxide.
It is raw material that the present invention adopts carbazole derivative and 1,6-dibromo-hexane, has synthesized the organic electroluminescent compounds XCP based on carbazyl, and synthetic method is simple, and the molecular structure of XCP by X-ray single crystal diffraction,
1HNMR and FT-IR characterize and are verified.
The present invention also adopts solvent crystallization simultaneously, has turned out the monocrystalline of the measured compounds X CP of matter.Specifically the above-mentioned XCP for preparing is dissolved in the mixing solutions of methylene dichloride and sherwood oil, it is concentrated that placement is volatilized solvent naturally, crystallize out, and collection obtains the monocrystalline of the compound of general formula (I) expression.The XCP monocrystalline that the present invention prepares has good single crystal diffraction ability.
The present invention has also further measured the thermal stability of XCP.Use the thermogravimetric of French SETARAM company/differential thermal combined instrument, temperature rise rate with 5～10 ℃/min carries out thermal stability analysis, the second-order transition temperature that test draws XCP is 92～110 ℃, phosphorescent light body material CBP with respect to classics has improved 30～40 ℃, and 321～350 ℃ of heat decomposition temperatures have excellent thermostability.
The present invention has also measured fluorescent characteristic and the antenna effect characteristic of XCP simultaneously, and when comprising room temperature, concentration is 1 * 10 in dichloromethane solution
-5The photoluminescence spectra of mol/L, during 77K, the antenna effect spectrum in 2-methyltetrahydrofuran solution.After measured, the room temperature fluorescence emission peak of XCP is positioned at 351～380nm scope, calculated the triplet of XCP by antenna effect spectrum in 3.2～3.5eV scope, with respect to CBP, in a big way raising is arranged, can effectively stop the passback of triplet energy state, thereby improve the luminous efficiency of organic electro phosphorescent device.
The present invention has also measured the chemical property of XCP.Use the cyclic voltammetry curve of Dutch Autolab/PG STAT302 electrochemical test test product, reference electrode is 222 type mercurous chloride electrodes, working electrode and electrode is respectively platinized platinum is dissolved in acetone as supporting electrolyte with the tetrabutylammonium perchlorate, concentration 1mol/L.After measured, the oxidation take-off potential of XCP (
) be 1.24～1.58V, the highest occupied molecular orbital (HOMO) that calculates according to electrochemical method and energy level (relative vacuum energy level) relational expression of lowest unoccupied molecular orbital (LUMO), the HOMO energy level that calculates XCP be-5.98～-6.32eV.In conjunction with the XCP ultra-violet absorption spectrum of 264～346nm, be 3.51～3.52eV but proximate calculation goes out the optical band gap of XCP, the lowest unoccupied molecular orbital energy level that calculates at last XCP is-2.47～-2.81eV.
The present invention also provides a kind of organic electro phosphorescent device, includes the above-mentioned organic electroluminescent compounds of the present invention in described organic electro phosphorescent device.
As everyone knows, organic electro phosphorescent device comprises two electrodes and is inserted in two organic layers between electrode, the organic layer structure comprises hole transmission layer, luminescent layer and electron transfer layer at least, comprise or do not comprise hole injection layer and electron injecting layer, luminescent layer wherein is made of the guest materials of phosphorescent light body material and doping again.And then the above-mentioned organic electroluminescent compounds of the present invention is used as the phosphorescent light body material in organic electro phosphorescent device.
Particularly, the present invention is with organic electroluminescent phosphorescence luminescent material, and namely guest materials is entrained in host compound XCP as luminescent layer, and adopting the traditional vacuum vapour deposition method to prepare structure is ITO/NPB/Ir (ppy)
3(7wt%): the device of XCP/TPBi/LiF/Al.In said structure, ITO is tin indium oxide, as anode material; NPB is N, N '-two (1-naphthyl)-N, and N ,-phenylbenzene-1,1 '-biphenyl-4, the abbreviation of 4 '-diamines is hole mobile material; Ir (ppy)
3Be the abbreviation that three (2-phenylpyridines) close iridium, be guest materials; TPBi is that (1-phenyl-1H-benzimidazolyl-2 radicals-yl) abbreviation of benzene is electron transport material to 1,3,5-three; LiF is electron injection material; Al is cathode material.
The organic phosphorescent electroluminescence device of above-mentioned preparation, the maximum glow peak of electroluminescence spectrum all is positioned at 520nm, is guest materials Ir (ppy)
3Luminous, when driving voltage was 12～15V, the high-high brightness of device was 9500～10103cd/m
2, when XCP was hCP, the maximum luminous efficiency of device was 15.1cd/A, with respect to having improved 34.8% with CBP (4,4 ,-two (9-carbazole) biphenyl) for the luminescent device of material of main part.
Obviously, above-mentioned is not restriction to protection domain of the present invention with XCP as the structure of the organic phosphorescent electroluminescence device of phosphorescent light body material, and the present invention also is not limited to above-mentioned device architecture.The aim of the present invention protection be with XCP as phosphorescent light body material, every with the organic phosphorescent electroluminescence device of XCP as phosphorescent light body material, all be construed as protection scope of the present invention.For example, can also prepare the organic phosphorescent electroluminescence device of following structure.
ITO/m-MTDATA(10nm)/NPB(30nm)/Ir(piq)
2acac:XCP/TPBi(30nm)/LiF(1nm)/Al。
ITO/m-MTDATA(10nm)/NPB(30nm)/Ir(piq)
2acac:XCP/Bphen(30nm)/LiF(1nm)/Al。
ITO/m-MTDATA(10nm)/NPB(30nm)/Ir(piq)
2acac:XCP/BCP(30nm)/LiF(1nm)/Al。
ITO/NPB(30nm)/FIrpic:XCP/Bphen(30nm)/LiF(1nm)/Al。
ITO/NPB(30nm)/FIrpic:XCP/?TPBi(30nm)/LiF(1nm)/Al。
ITO/NPB(30nm)/FIrpic:XCP/?BCP(30nm)/LiF(1nm)/Al。
In sum, the organic electroluminescent compounds based on carbazyl that the present invention prepares has higher second-order transition temperature, as organic phosphorescent light body material, can effectively improve the stability of phosphorescence device; Simultaneously, this compounds has wider optical band gap and higher triplet, good electronic transmission performance is arranged, in organic phosphorescent electroluminescence device as phosphorescent light body material, can effectively avoid guest materials to the energy passback of material of main part, thereby improve luminous efficiency and the life-span of phosphorescence device, satisfy the requirement of preparation high-level efficiency phosphorescence device.
Description of drawings
Fig. 1 is the nuclear magnetic spectrogram of the hCP for preparing of embodiment 1.
Fig. 2 is the infrared spectrogram of the hCP for preparing of embodiment 1.
Fig. 3 is the structure iron of the hCP monocrystalline for preparing of embodiment 1.
Fig. 4 is uv-absorbing and the utilizing emitted light spectrogram of the hCP for preparing of embodiment 1.
Fig. 5 is the cyclic voltammetry curve figure of the hCP for preparing of embodiment 1.
Fig. 6 is TG, DTG and the DSC graphic representation of the hCP for preparing of embodiment 1.
Fig. 7 is the electroluminescent spectrum figure of organic electroluminescence device under different voltages take hCP as material of main part.
Fig. 8 is respectively as current density-voltage and the brightness-voltage curve of the organic electroluminescence device of material of main part with hCP and CBP.
Fig. 9 is respectively as the current efficiency of the organic electroluminescence device of material of main part-current density graphic representation with hCP and CBP.
Embodiment
With 10.032g carbazole and 7.3191g 1, the 6-dibromo-hexane is dissolved in the 90ml tetrahydrofuran (THF) successively, adds 0.192g catalyzer Tetrabutyl amonium bromide under nitrogen protection; mix; add the potassium hydroxide solution 40ml of 16mol/L, be warming up to backflow, reaction 12h.Reaction is used the dichloromethane extraction organic layer after finishing, and dried over mgso is revolved inspissation contracting solution, upper silica gel column chromatography, and with sherwood oil drip washing, the volatilization leacheate is purified with ethyl alcohol recrystallization, obtains white needles 1,6-two carbazyl hexane (hCP) crystal.
[0040]With
1HNMR and FT-IR characterize the structure that obtains compound, in Fig. 1
1HNMR (CDCl
3, 600MHz) δ: 1.3881 (m, 4H), 1.8309 (m, 4H), 4.2439 (td, 4H), 7.2194 (ts, 4H), 7.32665 (d, 4H), 7.4194 (td, 4H), 8.0934 (d, 4H); FT-IR in Fig. 2 (KBr): 3445,2926,2852,2360,1626,1456,752,722cm
-1, prove that its molecular structure is hCP.
The hCP that obtains is dissolved in the mixing solutions of methylene dichloride that volume ratio is 1:2 and sherwood oil, places 48h, obtain the white needles transparent single crystal.(λ=0.71073nm) gathers the single crystal diffraction data to use German Bruker Smart CCD Advances in crystal X-ray diffraction instrument, utilizing Shelxl 97 software packages to resolve obtains: the single crystal structure of hCP (Fig. 3) is rhombic system, P2 (1) 2 (1) 2 (1) spacer, α=β=γ=90 °.Its crystal data and acquisition of information are as follows.
Wherein, the bond distance of chemical bond, bond angle are as shown in the table.
HCP is dissolved in obtains concentration 5 * 10 in methylene dichloride
-6The solution of mol/L is tested its uv-visible absorption spectra with Lambda Bio 40 ultraviolet-visible spectrometers; HCP is dissolved in obtains concentration 1 * 10 in methylene dichloride
-5The solution of mol/L uses Cary Eclipse spectrophotofluorometer to test its fluorescence spectrum; HCP is dissolved in 2-methyltetrahydrofuran solution, uses Hitachi Model F-7000 pectrophosphorimeter to test the phosphorescence spectrum of its low temperature 77K.Three kinds of spectrograms are incorporated in Fig. 4.As shown in Figure 4, the ultraviolet absorption peak wavelength of hCP is mainly 264,294 and 346nm; Fluorescence emission peak in dichloromethane solution lays respectively at 351 and 368nm; Antenna effect spectrum glow peak when temperature 77K is respectively 369,413 and 443nm, is calculated the T of hCP by the antenna effect spectrometer
1Energy level is 3.36eV, than the T of CBP
1The high 0.8eV of energy level (2.56eV).
The cyclic voltammetry curve of hCP as shown in Figure 5, the HOMO energy level that calculates hCP is-5.98eV.In conjunction with the ultra-violet absorption spectrum data of Fig. 2, be 3.51eV but proximate calculation goes out the optical band gap of hCP, and the lumo energy that calculates hCP is-2.47eV.
Fig. 6 is thermogravimetric (TG) curve and second-heating differential thermal (DSC) graphic representation of hCP, second-order transition temperature and the heat decomposition temperature that can obtain hCP from figure are respectively 93 ℃ and 321 ℃, and its second-order transition temperature has improved 31 ℃ than classical phosphorescent light body material CBP.
Select classical green PhOLED device architecture, respectively take hCP and CBP as phosphorescent light body material, with the green phosphorescent luminescent material Ir (ppy) of 7wt%
3Be entrained in material of main part as luminescent layer, and be respectively hole transmission layer and electron transfer layer with NPB and TPBi, prepared device A and device B.
Device A:
ITO/NPB(30nm)/Ir(ppy)
3(7wt%):hCP(30nm)/TPBi(30nm)/LiF(1nm)/Al(300nm)。
Device B:
ITO/NPB(30nm)/Ir(ppy)
3(7wt%):CBP(30nm)/TPBi(30nm)/LiF(1nm)/Al(300nm)。
Use PR655 spectral radiometer and Keithley 2400 digital sourcemeters to test the properties of device, all tests are all carried out under atmospheric environment.
Fig. 7 is the electroluminescent spectrum of device A, and its maximum glow peak wavelength is 520nm, corresponding to Ir (ppy)
3The green emission peak, realized that material of main part hCP is to guest materials Ir (ppy)
3Total energy shift.
Fig. 8 is current density-voltage and the brightness-voltage curve of device, and as can be seen from the figure, the bright voltage that opens of device A and device B is respectively 4.2 and 5V.When driving voltage was 15V, device A reached maximum luminousing brightness 10103cd/m
2, improved 8% than the device B take CBP as material of main part.
Fig. 9 is the current efficiency-current density curve of device, when current density is 12mA/cm
2The time, device A reaches maximum current efficient 15.1cd/A, and B has improved 34.8% with respect to device.
With 11.72g 3,6-Dimethylcarbazole and 7.3191g 1,6-dibromo-hexane are dissolved in the 90ml tetrahydrofuran (THF) successively; add 0.192g catalyzer Tetrabutyl amonium bromide under nitrogen protection, mix, add the potassium hydroxide solution 40ml of 16mol/L; be warming up to backflow, reaction 12h.Reaction is used the dichloromethane extraction organic layer after finishing, and dried over mgso is revolved inspissation contracting solution, upper silica gel column chromatography, with sherwood oil drip washing, the volatilization leacheate is purified with ethyl alcohol recrystallization, obtain white needles 1,6-two (4,7-Dimethylcarbazole base) hexane (mhCP) crystal.
The mhCP that negate should obtain is dissolved in the mixing solutions of methylene dichloride that volume ratio is 1:2 and sherwood oil, places 48h, obtains the white needles transparent single crystal.
Embodiment 3
With 13.39g 3,6-diethyl carbazole and 7.3191g 1,6-dibromo-hexane are dissolved in the 90ml tetrahydrofuran (THF) successively; add the 0.192g Tetrabutyl amonium bromide; add the potassium hydroxide solution 40ml of 16mol/L after mixing, back flow reaction 12h, aforesaid operations all carry out under nitrogen protection.Reaction is used the dichloromethane extraction organic layer after finishing, and dried over mgso is revolved inspissation contracting solution, upper silica gel column chromatography, with sherwood oil drip washing, the volatilization leacheate is purified with ethyl alcohol recrystallization, obtain white needles 1,6-two (4,7-diethyl carbazyl) hexane (ehCP) crystal.
[0056]The ehCP that negate should obtain is dissolved in the mixing solutions of methylene dichloride that volume ratio is 1:2 and sherwood oil, places 48h, obtains the white needles transparent single crystal.
Claims (6)
1. organic electroluminescent compounds based on carbazyl has the general structure of formula (I) expression:
In formula: R is H, CH
3Or CH
2CH
3
2. the preparation method of the described organic electroluminescent compounds of claim 1 is that the carbazole derivative by general formula (II) expression of stoichiometric ratio prepares with the reaction of 1,6-dibromo-hexane the compound that claim 1 general formula (I) represents,
In formula: R defines with claim 1.
3. preparation method according to claim 2; it is the carbazole derivative and 1 with general formula (II) expression of stoichiometric ratio; the 6-dibromo-hexane is dissolved in tetrahydrofuran solvent; under nitrogen protection and the existence of Tetrabutyl amonium bromide catalyzer; add the alkali hydroxide soln back flow reaction, obtain the compound of general formula (I) expression.
4. preparation method according to claim 3, is characterized in that described alkali metal hydroxide is potassium hydroxide.
5. an organic electro phosphorescent device, include organic electroluminescent compounds claimed in claim 1 in described organic electro phosphorescent device.
6. organic electro phosphorescent device according to claim 5, described organic electroluminescent compounds is as the phosphorescent light body material in organic electro phosphorescent device.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108409787A (en) * | 2018-03-16 | 2018-08-17 | 南京邮电大学 | A kind of phosphorescence manganese complex and its preparation method and application |
| CN111689891A (en) * | 2020-06-24 | 2020-09-22 | 太原理工大学 | Light activated dynamic long-life phosphorescent material and application thereof |
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Cited By (4)
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| CN108409787A (en) * | 2018-03-16 | 2018-08-17 | 南京邮电大学 | A kind of phosphorescence manganese complex and its preparation method and application |
| CN108409787B (en) * | 2018-03-16 | 2020-05-15 | 南京邮电大学 | Phosphorescent manganese complex and preparation method and application thereof |
| CN111689891A (en) * | 2020-06-24 | 2020-09-22 | 太原理工大学 | Light activated dynamic long-life phosphorescent material and application thereof |
| CN111689891B (en) * | 2020-06-24 | 2021-08-17 | 太原理工大学 | Light activated dynamic long-life phosphorescent material and application thereof |
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Application publication date: 20130508 |