CN112300135B - Carbazole-azaheterocycle A-D-A type room temperature organic phosphorescent white light material - Google Patents
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Abstract
The invention belongs to the field of organic luminescent materials, and particularly relates to a carbazole-nitrogen heterocyclic A-D-A type room temperature organic phosphorescent white light material. The room temperature organic phosphorescent white material takes 9-benzylcarbazole as an electron donor (D) unit and diazabenzene as an electron acceptor (A) unit to obtain an A-D-A type room temperature organic phosphorescent white material, the material can realize cold white emission in a crystal state, and a luminescent spectrum simultaneously covers blue fluorescence and yellow-green phosphorescent emission with the service life of 105 ms.
Description
Technical Field
The invention belongs to the field of organic luminescent materials, and particularly relates to a metal-free room temperature organic phosphorescent material which is an A-D-A type room temperature organic phosphorescent white light material constructed by taking a 9-benzylcarbazole electron donor (D) unit as a central core and a diazabenzene electron acceptor (A) unit as an end group.
Background
In recent years, photoelectric materials having room temperature phosphorescent properties have attracted attention in the fields of illumination, bio-imaging, forgery prevention, encryption, and the like. The room temperature phosphorescent materials reported so far are mostly metal-based inorganic compounds or organic compounds, such as alkaline earth metal aluminate/silicate, transition metal sulfide, cyclometalated platinum (or iridium) organic compounds, etc., and these materials have the problems of cytotoxicity, difficult processing, high cost, etc. The pure organic room temperature phosphorescent material without metal is a class of phosphorescent material developed in recent years, and has the advantages of easy structure modification, low cost, large Stokes shift, good biocompatibility and the like, so that the pure organic room temperature phosphorescent material is concerned by the industry and is considered to be a class of room temperature phosphorescent material with great development potential.
Phosphorescence is the singlet excited state (S) of excited molecules1) The exciton of (2) undergoes intersystem crossing (ISC) and transits to a triplet excited state (T)1) Then from T1Transition to the ground state (S)0) The process of releasing energy in a manner of radiative luminescence. However, excitons in the singlet excited state are transited to the triplet excited state (T) by intersystem crossingn) In general, the spin direction of the electron is changed to form two electrons having the same spin direction, which is easy to be usedAnd is quenched by oxygen and water in the air, and thus, phosphorescence of a pure organic compound containing no metal at room temperature is generally hardly observed.
The efficiency of intersystem crossing is generally low for pure organic compounds which are free of metals. In order to realize room temperature phosphorescence, it is important to increase intersystem crossing (ISC), enhance spin coupling (SOC), and expand the triplet exciton source. To this end, researchers have developed three approaches to achieve room temperature phosphorescence of pure organic compounds in conjunction with the EL-colored rule: (1) the introduction of halogens (bromine and iodine) and the utilization of heavy atom effect realize the high-efficiency utilization of triplet excitons, but the bonds formed by bromine and iodine and carbon atoms are weak and are easy to decompose. (2) Introduction of hetero atom (N, S, P) with lone pair electrons enhances electron transition of N → pi and pi → pi, and improves intersystem crossing (ISC) efficiency. (3) The rigidity of the medium is enhanced by means of host-guest doping, crystal induction, polymer embedding and the like, and the nonradiative transition rate (k) caused by molecular rotation, vibration and the like is inhibitednr) Increasing the radiative transition rate (k) of triplet excitonsr) Thereby improving the utilization rate of triplet excitons and improving the luminous efficiency.
Carbazole molecules are a class of fluorescent compounds which are commercially produced on a large scale and are low in price, have room-temperature phosphorescence in a crystalline state, but are easily oxidized in air due to the existence of an N-H structure.
Disclosure of Invention
The invention constructs an A-D-A type room temperature organic phosphorescent white light material by taking 9-benzyl carbazole as an electron donor (D) unit and diazabenzene as an electron acceptor (A) unit. The material realizes cold white light emission in a crystal state, and the emission spectrum simultaneously covers blue fluorescence and yellow-green phosphorescence emission with the service life of 105 ms.
The novel A-D-A type room temperature organic phosphorescent white light material provided by the invention has a molecular structure shown in a formula 1.
Formula 1
Wherein R is 2-pyrimidinyl (CBM), 2-pyrazinyl (CBPz) and 2-methylpyrazinyl (CBMPz). R is pyrimidinyl as the preferred group.
The preferable A-D-A type room temperature organic phosphorescent white light material Compound (CBM) has the following structure:
the structural characteristics of the molecule are as follows: (1) the nitrogen heterocyclic ring in the molecule contains nitrogen heterocyclic atoms of lone pair electrons, so that spin orbit coupling of singlet state-triplet state can be promoted, and the intersystem crossing efficiency is improved; (2) benzyl in the molecule can protect active N-H bond; (3) the methylene carbon atom on the benzyl has a unique regular tetrahedron configuration, and is favorable for the molecules to form strong intermolecular interaction in the crystal; (4) the crystals containing benzyl structures have less free volume in unit cells, can inhibit non-radiative transition of molecules and enhance phosphorescence efficiency.
The material realizes cold white light emission at room temperature in a crystal state, the luminescence spectrum is 400nm-650nm, and the luminescence spectrum simultaneously covers blue fluorescence and yellow-green phosphorescence emission with the service life of 105 ms.
A carbazole-nitrogen heterocyclic A-D-A type room temperature organic phosphorescence white light material is used as a light emitting layer material in an organic light emitting diode.
Compared with the prior art, the invention has the beneficial effects that: the use of diazepine groups promotes the room temperature phosphorescent white emission of purely organic compounds. Compared with the introduction of bromine and iodine halogen, the A-D-A type room temperature organic phosphorescent material containing the diazepine group can be used as a luminescent layer material and has wide application prospect in Organic Light Emitting Diodes (OLEDs).
Drawings
FIG. 1 is a UV-VIS spectrum of a CBM prepared in example 1 according to the present invention in a solution state;
FIG. 2 is a photoluminescence spectrum of a CBM prepared in example 1 of the present invention in a solution state;
FIG. 3 is a thermogravimetric plot (TGA) of the CBM produced in example 1 of the present invention;
FIG. 4 is a Differential Scanning Calorimetry (DSC) curve of a CBM made in example 1 of the present invention;
FIG. 5 shows phosphorescence emission spectra of 77K and 298K in tetrahydrofuran aqueous solution of CBM prepared in example 1;
FIG. 6 shows the luminescence and delayed luminescence spectra of the CBM prepared in example 1 of the present invention in a crystalline state at a temperature of 298K;
FIG. 7 shows a life decay curve obtained by transient luminescence decay spectrum test of 540nm, 510nm, 460nm and 430nm of CBM prepared in example 1 of the present invention in a crystal state;
FIG. 8 is a spectrum of light emission of CBPz prepared in example 3 of the present invention in a crystalline state at a temperature of 298K.
Detailed Description
The following specific examples are intended to further illustrate the invention, but these specific embodiments do not limit the scope of the invention in any way.
Example 1
The synthesis route of the CBM is as follows:
preparation of Compound 1
3, 6-dibromocarbazole (5.00g, 15.38mmol) and NaH (972mg, 23.09mmol) were added to dry DMF (30mL), stirred at room temperature under nitrogen for 1h, then benzyl bromide (1.83mL, 15.38mmol) was slowly added dropwise through a needle tube, and after the addition was complete, stirring was continued at room temperature for 12 h. Cooling to room temperature, slowly pouring the reaction liquid into ice water to generate white floccule, performing suction filtration to obtain a solid, and drying under vacuum. 6.38g of a white solid was obtained (98% yield).1H NMR(400MHz,DMSO)δ8.52(s,2H),7.65(d,J＝8.7Hz,2H),7.60(d,J＝8.7Hz,2H),7.24(dd,J＝12.5,7.0Hz,3H),7.12(d,J＝7.3Hz,2H),5.68(s,2H).
Preparation of Compound 2
Compound 1(3.00g, 7.2mmol), pinacol diboron (4.40g, 17.3mmol), potassium acetate (4.2g, 43.3mmol), 1,1' -bisDiphenylphosphinobenzene palladium dichloride (314mg, 0.43mmol) was added to toluene (50ml) and the reaction refluxed for 24h under nitrogen. Cooling to room temperature, distilling off toluene, and then using CH2Cl2And extracting, washing the extract with water, and drying over anhydrous magnesium sulfate. Silica gel column chromatography (petroleum ether: dichloromethane ═ 1:1), recrystallization and drying gave 3.09g of a white solid (84% yield).1H NMR(300MHz,CDCl3)δ8.70(s,2H),7.88(d,J＝1.1Hz,1H),7.85(d,J＝1.1Hz,1H),7.37–7.36(m,1H),7.34(d,J＝0.4Hz,1H),7.23–7.21(m,4H),7.08(dd,J＝7.2,2.3Hz,2H),5.54(s,2H).
Preparation of Compound CBM
Compound 2(1.00g, 1.9mmol), 2-bromopyrimidine (687mg, 4.3mmol), tetrakis (triphenylphosphine) palladium (69.30mg, 0.114mmol), 2M potassium carbonate solution (4.3ml), purified by column chromatography with toluene: and (3) completely dissolving the ethanol-3: 1 mixed solvent, heating to 85 ℃ under the protection of nitrogen, and reacting for 24 hours. Cooling to room temperature, distilling off the solvent, and then using CH2Cl2And extracting, washing the extract with water, and drying over anhydrous magnesium sulfate. Silica gel column chromatography (petroleum ether: dichloromethane ═ 2:1), recrystallization, and drying gave 680mg of a solid (86% yield).1H NMR(400MHz,DMSO)δ9.30(s,2H),8.92(d,J＝4.7Hz,4H),8.57(d,J＝8.6Hz,2H),7.82(d,J＝8.7Hz,2H),7.41(t,J＝4.7Hz,2H),7.30(d,J＝6.9Hz,2H),7.24(d,J＝7.4Hz,3H),5.79(s,2H).
Example 2
Room temperature phosphorescent performance testing of CBM in example 1:
FIGS. 1 and 2 show the UV absorption spectrum and photoluminescence spectrum of CBM in tetrahydrofuran, chloroform and toluene solution, respectively, wherein the absorption band around 320-335nm in FIG. 1 is attributed to n- π transition absorption, and the absorption band around 335-350nm is attributed to π - π transition absorption.
FIG. 3 is a thermogravimetric curve of CBM, corresponding to a temperature of 364 ℃ when the mass loss is 5%, i.e. the decomposition temperature TdAt 364 ℃;
FIG. 4 is a DSC curve of CBM, which shows a melting temperature TmAt 253 ℃ and a crystallization temperature TcThe temperature was 157 ℃. FIGS. 3 and 4 illustrate that CBM hasBetter thermal performance.
FIG. 5 shows CBM in tetrahydrofuran solution (10)-5M) at 77K, and comparing the fluorescence spectrum at 298K, the inventors found that new emission peaks appear at 440nm, 475nm and 500nm in the phosphorescence spectrum at 77K of CBM, and suspected that the new emission peaks belong to phosphorescence peaks, and verified that the three emission peaks still exist after delaying for 2ms and 5ms respectively in the phosphorescence delay spectrum at 77K. Indicating that the solution state has phosphorescence emission at a low temperature of 77K.
FIG. 6 shows the emission spectrum of CBM at 298K in the crystal state, the emission spectrum is 400nm-650nm, and the emission spectrum belongs to cold white light emission. Transient luminescence decay spectrum tests are respectively carried out on 430nm, 460nm, 510nm and 540nm (see figure 7), the fitting life at 430nm is 1.79ns through life fitting, the fitting life at 460nm is 50.05ns, both short-life fluorescence emission and the fitting life at 510nm and 540nm is 58.16ms and 105.89ms respectively, the phenomenon belongs to long-life phosphorescence emission, the phenomenon is also proved in a delayed luminescence test of the crystal under 298K (see figure 6), and when the delay time is 105ms, an emission peak only appears at about 530 nm.
Example 3
The synthesis route of CBPz is as follows:
the preparation of compounds 1, 2 is described in example 1.
Preparation of Compound CBPz
Compound 2(1.00g, 1.9mmol), 2-bromopyrazine (687mg, 4.3mmol), tetrakis (triphenylphosphine) palladium (69.30mg, 0.114mmol), 2M potassium carbonate solution (4.3ml), purified with toluene: and (3) completely dissolving the ethanol-3: 1 mixed solvent, heating to 85 ℃ under the protection of nitrogen, and reacting for 24 hours. Cooling to room temperature, distilling off the solvent, and then using CH2Cl2And extracting, washing the extract with water, and drying over anhydrous magnesium sulfate. Silica gel column chromatography (petroleum ether: dichloromethane: 2:1), recrystallization, and drying to obtain 680mg of solid,(86% yield).1H NMR(400MHz,DMSO)δ9.42(d,J＝1.2Hz,2H),9.20(d,J＝1.3Hz,2H),8.73–8.72(m,2H),8.58(d,J＝2.4Hz,2H),8.33(d,J＝1.6Hz,1H),8.31(d,J＝1.5Hz,1H),7.85(s,1H),7.83(s,1H),7.29(d,J＝6.9Hz,2H),7.23(d,J＝7.9Hz,3H),5.80(s,2H).
FIG. 8 is an emission spectrum at 298K of a crystal whose donor is a 2-pyrazine group, the emission spectrum being a single peak emission at 425nm, which is a blue-violet light emission.
When the donor is a 2-methylpyrazine group, the sample is in a liquid state, and a crystal sample cannot be obtained.
Thus, the preferred group is when the donor is a 2-pyrimidine group, and the crystal luminescence is cool white emission at 298K.
While the present invention has been described in connection with the preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. In light of the present inventive concept, those skilled in the art will recognize that certain changes may be made in the embodiments of the invention to which the invention pertains without departing from the spirit and scope of the claims.
Claims (3)
1. A carbazole-nitrogen heterocyclic A-D-A type room temperature organic phosphorescent white light material is characterized in that the structural formula of the room temperature organic phosphorescent white light material is as follows:
the carbazole-nitrogen heterocyclic A-D-A type group material can realize cold white light emission at room temperature in a crystal state.
2. The carbazole-nitrogen heterocyclic a-D-a type room temperature organic phosphorescent white light material according to claim 1, wherein the carbazole-pyrimidine a-D-a type group material has a light emission spectrum covering both blue fluorescence and yellow-green phosphorescent emission with a phosphorescent lifetime of 105 ms.
3. The use of the carbazole-nitrogen heterocyclic a-D-a type room temperature organic phosphorescent white light material according to claim 1, wherein the carbazole-nitrogen heterocyclic a-D-a type room temperature organic phosphorescent white light material is used as a light emitting layer material in an organic light emitting diode.
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| KR20130069431A (en) * | 2011-12-16 | 2013-06-26 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| KR20160077485A (en) * | 2014-12-23 | 2016-07-04 | 주식회사 네패스 | Nitrogen hetero ring compound and organic emitting device employing the same |
| EP3392247A1 (en) * | 2017-04-19 | 2018-10-24 | Cynora Gmbh | Organic molecules, in particular for use in optoelectronic devices |
| CN109293637A (en) * | 2018-09-18 | 2019-02-01 | 南京邮电大学 | A kind of diazines isomers blue light material |
| CN111205272A (en) * | 2020-02-20 | 2020-05-29 | 长春海谱润斯科技有限公司 | Material for organic electroluminescent device and organic electroluminescent device thereof |
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| CN102206207A (en) * | 2011-04-15 | 2011-10-05 | 南京邮电大学 | 4-aryl pyrimidine or 4-heterocyclic aryl pyrimidine compound luminescent material and preparation method thereof |
| KR20130069431A (en) * | 2011-12-16 | 2013-06-26 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| KR20160077485A (en) * | 2014-12-23 | 2016-07-04 | 주식회사 네패스 | Nitrogen hetero ring compound and organic emitting device employing the same |
| EP3392247A1 (en) * | 2017-04-19 | 2018-10-24 | Cynora Gmbh | Organic molecules, in particular for use in optoelectronic devices |
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| CN111205272A (en) * | 2020-02-20 | 2020-05-29 | 长春海谱润斯科技有限公司 | Material for organic electroluminescent device and organic electroluminescent device thereof |
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