CN114605313B - Bicarbazole material based on fluorene units and preparation method and application thereof - Google Patents
Bicarbazole material based on fluorene units and preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the field of organic electroluminescent materials, and particularly relates to a fluorene unit-based dicarbazole material, a preparation method and application thereof; cyano groups, fluorene units and alkyl chains are introduced on the basis of the carbazole rich in electron groups, and a dicarbazole structure center is synthesized through Suzuki coupling reaction, so that electron transmission and hole transmission can be performed on the center structure of the dicarbazole, meanwhile, the structure has excellent thermal stability, the fluorene units are modified to effectively adjust the emission light wavelength of the material, deep blue luminescence is realized, and a higher triplet energy level is ensured; meanwhile, the material has a narrower half-peak width, and can be used as a main body material of a high-purity deep blue light OLED device.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and relates to a deep blue light bicarbazole material based on fluorene unit modification, and a preparation method and application thereof.
Technical Field
Organic Light Emitting Diodes (OLEDs) were first proposed by two scientists, tang and VanSlyke (appl. Phys. Lett.1987,51,913.Doi. Org/10.1063/1.98799) in 1987, and have received considerable attention from researchers in the scientific community as a new generation of full-color displays and for widespread use on solid-state illumination source materials. Since thirty years, OLEDs have become commercially available display materials for use in electronic devices such as mobile phones and computers, and in spite of significant progress in this field, it is necessary to realize red, green and blue emission with high color purity in order to realize full-color display. Currently, blue phosphorescent OLEDs cannot meet the needs of the industry due to short lifetime, low efficiency, etc. (j.am. Chem. Soc.,2011,133 (44): 17895.doi. Org/10.1021/ja207554 h), and developing efficient and stable blue and deep blue OLED materials with low cost and low price remains a great challenge. The dicarbazole is a structurally stable electron-rich body, and has the capability of electron transmission and charge transmission at the same time as a bipolar transmission center, and various derivatives taking the dicarbazole as the center can be used as a main material of a blue phosphorescent OLED (ACS appl. Mater. Interfaces 2014,6, (17), 14874.Doi. Org/10.1021/am502848 c), but the blue light emission purity and the thermal stability of the main material of phosphorescence are required to be improved, and the capability of electron transmission is slightly insufficient.
Disclosure of Invention
In view of the defects, the invention constructs the design thought of the acceptor structure by introducing electron-deficient groups, not only can effectively improve the triplet state energy level, but also the material has excellent thermal stability. The introduction of fluorenyl can regulate and control the emission wavelength of the material to move to a deeper blue light region, and a blue light-emitting main body material with a bipolar transmission center is synthesized.
The invention provides a synthesis method with mild conditions and low cost to obtain a material with bipolar transmission performance, and a donor-acceptor structure DFCzPhCN is synthesized by introducing pseudohalogen cyano and fluorene units into a center main body of dicarbazole. The pseudohalogen substituent effect can promote the intersystem crossing process, quench excitons of carbazole moieties, and in an aggregation state, a charge transfer state formed between cyanobenzene and carbazole can serve as a transition state between a singlet state and a triplet state, so that the intersystem crossing process and the inverse intersystem crossing process of excitons are promoted. Compared with a monomer carbazole structure, the center structure of the biscarbazole can also carry out hole transport, and the thermal stability and the glass transition temperature of a substance are greatly improved and the film forming performance is better although the triplet state energy level is reduced. The introduction of alkyl chain can improve the film forming property of the compound and can effectively inhibit aggregation of components. Fluorene is used as an important structural segment of a blue light material, and the introduction of fluorene promotes deep blue light emission on one hand, and simultaneously ensures good bipolar property and higher triplet energy level. The red shift of the emission spectrum of the regulating material is realized, the blue light emission at 422nm is realized, and the regulating material can be used for a high-purity blue light OLED device.
In a first aspect, the present invention provides a fluorene unit-based bicarbazole material, which is a bipolar bicarbazole material modified by fluorene units and cyano groups, and the molecular structure of the compound is as follows:
in a second aspect, the invention also provides a specific preparation method of the compound DFCzPhCN, and the synthetic route is as follows:
corresponding to the synthetic route, the specific preparation steps are as follows:
the step (i) is that p-bromophenol reacts with bromoethane under anhydrous, anaerobic and alkaline conditions to generate 4-bromophenetole BrPh, and the reaction time is 12 hours;
step (ii) is a step of preparing fluorene unit-modified functional groups, specifically, a step of reacting fluorenone with an excessive amount of 4-bromophenyl ethyl ether in a format under anhydrous and anaerobic conditions at a reaction temperature of 65 ℃ for 12 hours to generate an intermediate product, namely fluorene unit-modified functional groups FPhOH;
step (iii) is a step of preparing a precursor of a cyano-modified bicarbazole center, specifically, a tribromocarbazole and 2-fluorobenzonitrile are reacted under an alkaline condition, the reaction temperature is 150 ℃, the reaction time is 12 hours, and an intermediate product, namely a precursor of the cyano-modified bicarbazole center, brCzPhCN is generated;
step (iv) is specifically that BrCzPhCN reacts with bisboronic acid pinacol ester for 12 hours at 110 ℃ under the condition of catalyst 1,1' -bis-diphenylphosphine ferrocene palladium dichloride to generate an intermediate product BCzPhCN;
step (v) is specifically that the intermediate product DCzPhCN with the bicarbazole is generated through Suzuki coupling reaction of the BrCzPhCN and the BCzPhCN, tetra (triphenylphosphine) palladium is used as a catalyst, and the reaction is carried out for 12 hours at the temperature of 110 ℃;
step (vi) is an acid catalyzed Friedel-Crafts reaction, specifically, the DCzPhCN and the fphh synthesize the product DFCzPhCN of the present invention at room temperature for 3 hours.
The compound DFCzPhCN with the bicarbazole bipolar center synthesized by the invention effectively adjusts the conjugated structure of the compound and the distribution state of electron cloud under the modification of cyano groups, fluorene units and alkyl chains, so that the whole structure generates Intramolecular Charge Transfer (ICT) after being excited by light; the compound has strong ultraviolet absorption and strong blue fluorescence emission at 422nm, and meanwhile, the temperature can reach 462 ℃ when the weight loss is 5%, so that the compound has excellent heat stability, and can be used for an OLED device luminescent layer material or a device serving as a blue light main body material;
the compound DFCzPhCN synthesized by the invention introduces fluorene units and pseudohalogen cyano groups on the basis of bicarbazole, and cyano groups bring obvious influence on the luminescence and charge transmission performance of bicarbazole bipolar materials, and bipolar centers can carry out charge transmission and hole transmission, so that the compound DFCzPhCN can be used as an electron or hole carrier transmission material.
The beneficial effects are that:
1. the synthetic raw materials are cheap and easy to obtain, and the cost is low.
2. Due to the existence of fluorene units, the red shift of the fluorescence emission spectrum of the material is effectively regulated, the strong ultraviolet-visible absorption and the strong blue fluorescence emission at 422nm are realized, and the material is suitable for being used as a luminescent layer material of a blue light OLED device.
3. Due to the existence of the cyano carbon-nitrogen triple bond and the conjugated extension of the carbazole at the 3 rd and 6 th positions, the temperature can reach 462 ℃ when the weight loss of the material is 5%, and the material has very excellent heat stability.
Drawings
FIG. 1 DFCzPhCN prepared in example 1 1 HNMR spectrogram;
FIG. 2 time-of-flight mass spectrum of DFCzPhCN prepared in example 1;
FIG. 3 DSC test curve of DFCzPhCN prepared in example 1;
FIG. 4 TGA test curve of DFCzPhCN prepared in example 1;
FIG. 5 UV-visible absorption spectrum of DFCzPhCN prepared in example 1 in toluene solution;
FIG. 6 fluorescence emission spectra of DFCzPhCN prepared in example 1 and DCzPhCN prepared in comparative example 1 in toluene solution;
FIG. 7 electrochemical oxidation profile of DFCzPhCN prepared in example 1 in methylene chloride solution.
Detailed description of the preferred embodiments
For a better understanding of the details of the present invention, the synthetic schemes and routes of the present invention will be further described through detailed experimental procedures. Specifically including synthetic routes and related characterization of properties. The examples do not limit the invention.
EXAMPLE 1 Synthesis of the Compound DFCzPhCN
The structure of compound DFCzPhCN is shown in the figure:
the preparation process of the compound DFCzPhCN is as follows:
step (i), synthesis of BrPh
Into a 100ml reaction flask were charged p-bromophenol (4.35 g,25.00 mmol), potassium carbonate (4.14 g,50.00 mmol), rubber stopper was sealed, and three repetitions were performed with evacuation and nitrogen replenishmentN, N-dimethylformamide (30 m) after bubbling a nitrogen balloon was added to the reaction flask to sufficiently dissolve the N, N-dimethylformamide, and then bromoethane (3.27 g,30.00 mmol) was added thereto under nitrogen atmosphere, the temperature of the oil bath was raised to 80℃and the mixture was refluxed for 8 hours. The lower organic phase was extracted three times with dichloromethane using TCL thin layer chromatography and the collected was taken up in anhydrous Na 2 SO 4 Drying, distilling off the solvent under reduced pressure, using petroleum ether: the eluent was purified by column chromatography on a silica gel column using methylene chloride (15:1 by volume) to give 3.41g (yield: 68%) of a pale yellow transparent oily liquid. Product nuclear magnetism: 1 H NMR(400MHz,CDCl 3 ，ppm)δ7.39–7.34(m,2H),6.79–6.74(m,2H),3.99(q,J＝7.0Hz,2H),1.41(td,J＝6.9,0.5Hz,3H).
step (ii) Synthesis of FPhOH
Into a 50mL reaction flask containing magneton was charged polished magnesium turnings (0.192 g,8 mmol), one shot of iodine, sealed with a rubber stopper, evacuated and nitrogen supplemented three times repeatedly, compound BrPh (1.00 g,5 mmol) and water-removed tetrahydrofuran (5 mL) solvent were slowly added into the flask while heating it with a hot air blower until a brownish yellow solution turned to a clear colorless solution indicating successful initiation, and heating was stopped. The reaction apparatus was transferred to a preheated oil bath, 9-fluorenone (0.90 g,5 mmol) was dissolved in tetrahydrofuran (5 mL), a reaction flask was added under nitrogen, the mixture was refluxed for 12 hours at 65℃and detected by TCL thin layer chromatography, and a saturated aqueous ammonium chloride solution (6 mL) was added to quench the reaction. The lower organic phase was washed with saturated brine and extracted three times with dichloromethane and the collected organic phase was taken up in anhydrous Na 2 SO 4 Drying, distilling off the solvent under reduced pressure, using petroleum ether: the eluent was eluted in methylene chloride (3:1 by volume) and purified by column chromatography on a silica gel column to give 0.97g (yield: 64.3%) of pale yellow solid powder. Product nuclear magnetism: 1 H NMR(400MHz,CDCl 3 ，ppm)δ7.68(d,J＝7.5Hz,2H),7.48–7.19(m,8H),6.90–6.74(m,2H),4.00(q,J＝7.0Hz,2H),2.68(s,1H),1.41(t,J＝7.0Hz,3H).
step (iii), synthesis of BrCzPhCN
3-bromocarboline was added to a 100ml reaction flaskOxazole (0.74 g,3.00 mmol) and cesium carbonate (1.40 g,4.00 mmol) were sealed with a rubber stopper, evacuated and circulated three times with additional nitrogen, and N, N-dimethylformamide solution (30 mL) after bubbling with a nitrogen balloon was added to the reaction flask to sufficiently dissolve it, and then 2-fluorobenzonitrile (0.49 g,4.00 mmol) was added under nitrogen atmosphere, and the temperature of the oil bath was raised to 160℃and condensed and refluxed for 12 hours. The reaction was cooled to room temperature, washed with saturated brine and extracted three times with dichloromethane, and the collected lower organic phase was taken up in anhydrous Na 2 SO 4 Drying, distilling off the solvent under reduced pressure, using petroleum ether: the eluent was eluted in methylene chloride (volume ratio: 5:1) and purified by column chromatography on a silica gel column to give 0.63g (yield: 78%) of a white flaky solid after separation. Product nuclear magnetism: 1 H NMR(400MHz,CDCl 3 ，ppm)δ8.27(d,J＝1.9Hz,1H),8.10(d,J＝7.8Hz,1H),7.94(dd,J＝7.8,1.6Hz,1H),7.82(td,J＝7.8,1.6Hz,1H),7.66–7.56(m,2H),7.55–7.44(m,2H),7.35(t,J＝7.5Hz,1H),7.20(d,J＝8.2Hz,1H),7.08(d,J＝8.7Hz,1H).
step (iv), synthesis of BCzPhCN
Into a 50ml two port reaction flask were charged BrCzPhCN (0.52 g,1.50 mmol), pinacol biborate (0.57 g,2.25 mmol), potassium acetate (0.45 g,4.50 mmol), sealed with a rubber stopper, evacuated and purged with nitrogen three times and Pd (DPPF) Cl was added under nitrogen 2 (0.0525 g,0.075 mmol) and then 1, 4-dioxane solution (25 mL) after nitrogen bubbling treatment was added to the reaction flask to dissolve it sufficiently, the temperature of the oil bath was raised to 110℃and the mixture was condensed and refluxed for 12 hours. The reaction was cooled to room temperature, washed with saturated brine and extracted three times with dichloromethane, and the collected lower organic phase was taken up in anhydrous Na 2 SO 4 Drying, distilling off the solvent under reduced pressure, using petroleum ether: the eluent was eluted in methylene chloride (3:1 by volume) and purified by column chromatography on a silica gel column to give 0.41g (yield: 67%) of a white solid powder. Product nuclear magnetism: 1 H NMR(400MHz,CDCl 3 ，ppm)δ8.65(s,2H),8.19(d,J＝7.7Hz,2H),7.95(d,J＝7.7Hz,2H),7.92–7.80(m,4H),7.63(t,J＝8.1Hz,4H),7.43(t,J＝7.7Hz,2H),7.34(t,J＝7.4Hz,2H),7.26(s,1H),7.19(dd,J＝8.3,3.0Hz,4H).
step (v), synthesis of DCzPhCN
To a 50mL reaction flask was added BrCzPhCN (0.29 g,0.84 mmol), compound BCzPhCN (0.40 g,0.10 mmol), sealed with a rubber stopper, evacuated and nitrogen-supplemented three times repeatedly, and under a nitrogen atmosphere, palladium tetraphenylphosphine (0.097 g,0.084 mmol) was added, and then a nitrogen-sparged 2mol/L potassium carbonate (5 mL), toluene (10 mL) and ethanol (5 mL) mixed solution was added to the reaction flask to dissolve it sufficiently, and the temperature of the oil bath was raised to 110℃and condensed and refluxed for 12 hours. The reaction was cooled to room temperature, washed with saturated brine and extracted three times with dichloromethane, and the collected lower organic phase was taken up in anhydrous Na 2 SO 4 Drying, distilling off the solvent under reduced pressure, using petroleum ether: the eluent was eluted in methylene chloride (volume ratio: 2:1) and purified by column chromatography on a silica gel column to give 0.22g (yield: 51.3%) of a white solid powder. Product nuclear magnetism: 1 H NMR(400MHz,CDCl 3 ，ppm)δ8.40–8.32(m,2H),8.15(dd,J＝7.8,3.2Hz,2H),7.88(d,J＝7.8Hz,2H),7.75(t,J＝7.8Hz,2H),7.68(dd,J＝7.9,5.6,1.8Hz,2H),7.60–7.50(m,4H),7.37(t,J＝7.7Hz,2H),7.28(d,J＝7.5Hz,2H),7.22(d,J＝8.5Hz,2H),7.15(d,J＝8.1Hz,2H).MALDL-TOF-MS:m/z calcd for C 38 H 22 N 4 [M] + :534.62,found:533.987.
step (vi), synthesis of DFCzPhCN
To a 50mL reaction flask containing a magneton was added DCzPhCN (0.20 g,0.40 mmol), dichloromethane (20 mL) was added for dissolution, boron trifluoride diethyl ether (0.128 g,0.80 mmol) was added, and compound FPhOH (0.302 g,1.00 mmol) was dissolved in dichloromethane solution (20 mL) and slowly added to the reaction flask at a rate of 2 drops per second, and stirred at room temperature for 3 hours. The reaction mixture was subjected to TCL thin layer chromatography, quenched with water, washed with saturated brine and extracted three times with dichloromethane, and the collected lower organic phase was taken up with anhydrous Na 2 SO 4 Drying, distilling off the solvent under reduced pressure, using petroleum ether: eluting with dichloromethane (volume ratio of 2:3), separating and purifying by column chromatography in silica gel column to obtain white0.24g of a coloured solid powder (yield: 54.0%). Product nuclear magnetism: 1 H NMR(400MHz,CDCl 3 ，ppm)δ8.18(s,2H),8.01(s,2H),7.94(d,J＝7.7Hz,2H),7.80(d,J＝7.6Hz,6H),7.67(t,J＝7.2Hz,2H),7.60(t,J＝8.0Hz,4H),7.50(d,J＝7.6Hz,4H),7.38(p,J＝6.1Hz,4H),7.30(s,6H),7.21(d,J＝8.4Hz,6H),7.06(d,J＝8.7Hz,2H),6.78(d,J＝8.3Hz,4H),3.99(q,J＝6.9Hz,4H),1.38(t,J＝6.9Hz,6H).MALDL-TOF-MS:m/z calcd for C 80 H 54 N 4 O 2 [M] + :1103.34,found:1102.70.
comparative example 1 Synthesis of DCzPhCN
The structure of intermediate DCzPhCN of comparative example 1 is shown in the figure:
the procedure for the synthesis of intermediate DCzPhCN of comparative example 1 was exactly the same as in example 1, steps (i) - (v).
Physical property test
Through 400MHz 1 The structure and relative molecular mass of the product were characterized by H NMR spectroscopy and MALDI-TOF-MS time-of-flight mass spectrometry. The thermal stability analysis was measured by a DSC differential scanning calorimeter and a simultaneous thermal analyzer under nitrogen atmosphere. The spectral properties of DFCzPhCN were determined by uv-vis spectrophotometer LAMBDA-35, fluorescence spectrophotometer RF-6000 analysis. The electrochemical properties of the compounds were tested by cyclic voltammetry at the Chi660E electrochemical workstation.
Weighing 5mg of DFCzPhCN, dissolving in 0.6mL of deuterium chloroform, and performing analysis and test by a nuclear magnetic resonance spectrometer to obtain DFCzPhCN 1 HNMR spectra, test results are shown in fig. 1.
1mg of DFCzPhCN was weighed and dissolved in methylene chloride, and analysis and test were performed by a time-of-flight mass spectrometer MALDI-TOF-MS to obtain a MALDI-TOF spectrum of DFCzPhCN, and the test result is shown in FIG. 2.
5mg of DFCzPhCN was weighed and tested by DSC differential scanning calorimeter under nitrogen to obtain a DSC test curve of DFCzPhCN, and the test result is shown in FIG. 3. The glass transition temperature of the DFCzPhCN is 141 ℃, which shows that the DFCzPhCN has better film forming property. The melting point can reach 225 ℃, which indicates that the material has good thermal stability.
5mg of DFCzPhCN was weighed and tested by a simultaneous thermal analyzer under nitrogen atmosphere to obtain a TGA test curve of DFCzPhCN, and the test results are shown in FIG. 4. 5% mass decomposition temperature T of DFCzPhCN d At 462 ℃, this benefits from the rigid conjugated structure between the dicarbazole and fluorene units, resulting in DFCzPhCN having a very high thermal decomposition temperature, which is beneficial for improving the lifetime and stability of the organic light emitting diode device.
Weighing 5.5mg of DFCzPhCN prepared in example 1, and dissolving in toluene to give a concentration of 1×10 -5 The mol/L solution is analyzed and tested by an LAMBDA-35 ultraviolet-visible spectrophotometer to obtain the ultraviolet-visible absorption spectrum of DFCzPhCN, and the test result is shown in figure 5. In the solution state, the absorption of the compound at 300nm is due to the n-pi transition of the dicarbazole backbone moiety, and the longer shoulder absorption after 320nm can be attributed to intramolecular charge transfer from the dicarbazole host to electron deficient cyanobenzene. The optical bandgap Eg was 3.36eV as derived from the spectrum.
Weighing 5.5mg of DFCzPhCN prepared in example 1, and dissolving in toluene to give a concentration of 1×10 -5 The mol/L solution is analyzed and tested by an RF-6000 model fluorescence spectrophotometer to obtain the fluorescence emission spectrum of DFCzPhCN, and the test result is shown in figure 6. 2.7mg of DCzPhCN prepared in comparative example 1 was dissolved in toluene to prepare a 1X 10 concentration - 5 The mol/L solution is analyzed and tested by a fluorescence spectrophotometer RF-6000 to obtain the fluorescence emission spectrum of DCzPhCN, the test result is shown in figure 6, and compared with the emission spectrum result of DFCzPhCN prepared in the embodiment 1, the result shows that the maximum fluorescence emission wavelength of DFCzPhCN after introducing fluorenyl units is red shifted by 11nm, the adjustability of the emission spectrum is realized, and the deep blue light emission of 422nm is achieved, so that the DFCzPhCN can be used as a main material of a luminescent layer of a deep blue phosphorescent OLED.
5mg of DFCzPhCN prepared in example 1 was weighed and dissolved in anhydrous and anaerobic methylene dichloride, the electrolyte was tetrabutylammonium hexafluorophosphate, and analysis and test were performed by means of Chi660E electrochemical work to obtain an electrochemical oxidation curve of DFCzPhCN, and the test result is shown in FIG. 7. Shows a reversible oxidation process, indicating good electrochemical stability. The combination of spectrum data DFCzPhCN can know that the HOMO energy level is-5.79 eV, the LUMO energy level is-2.43 eV, and the energy level can reach higher matching degree with the work function values of the materials of the anode ITO layer and the common electron input layer in terms of numerical value, thereby being beneficial to the realization of the electron transmission process; meanwhile, the dicarbazole center also has hole transmission performance, and the DFCzPhCN can have dual transmission performance of charge and hole at the same time, so that the dicarbazole is expected to become a bipolar transmission material.
Claims (10)
1. A fluorene unit-based dicarbazole material, characterized by the following structure:
2. a preparation method of a dicarbazole material based on fluorene units is characterized in that the synthetic route is as follows:
3. the method for preparing a fluorene unit-based dicarbazole material according to claim 2, wherein the preparation process of step (i) is specifically that p-bromophenol reacts with bromoethane under anhydrous, anaerobic and alkaline conditions to generate 4-bromophenetole BrPh, and the reaction time is 12 hours.
4. A method for preparing a fluorene unit-based dicarbazole material according to claim 3, wherein the preparation process of fphhoh is step (ii), wherein step (ii) is a step of preparing a fluorene unit-modified functional group, specifically, a reaction between fluorenone and an excess amount of 4-bromophenetole in a format under anhydrous and anaerobic conditions is performed at a reaction temperature of 65 ℃ for 12 hours, and an intermediate product, i.e., a fluorene unit-modified functional group fphhoh, is formed.
5. The method for preparing a dicarbazole material based on fluorene units according to claim 4, wherein the preparation process of BrCzPhCN is step (iii), and step (iii) is a step of preparing a precursor of cyano-modified dicarbazole center, specifically, the reaction of tribromocarbazole and 2-fluorobenzonitrile under alkaline condition is performed, the reaction temperature is 150 ℃, the reaction time is 12 hours, and an intermediate product, namely, the precursor of cyano-modified dicarbazole center BrCzPhCN is generated.
6. The method for preparing a fluorene unit-based dicarbazole material according to claim 5, wherein the preparation process of BCzPhCN is step (iv), and the step (iv) is specifically that the intermediate BCzPhCN is produced by reacting BrCzPhCN with bisboronic acid pinacol ester at 110 ℃ for 12 hours under the condition of catalyst 1,1' -bis-diphenylphosphino ferrocene palladium dichloride.
7. The method for preparing a dicarbazole material based on a fluorene unit according to claim 6, wherein the preparation process of DCzPhCN is step (v), and the step (v) is specifically that the intermediate DCzPhCN with the dicarbazole is generated through the Suzuki coupling reaction of the BrCzPhCN and the BCzPhCN, and the catalyst uses tetrakis (triphenylphosphine) palladium and reacts for 12 hours at 110 ℃.
8. The method for preparing a fluorene unit-based dicarbazole material according to claim 7, wherein the preparation process of DFCzPhCN is step (vi), and the step (vi) is an acid-catalyzed Friedel-Crafts reaction, specifically, the DFCzPhCN and the fphh are synthesized into the product DFCzPhCN of the present invention at room temperature, and the reaction time is 3 hours.
9. Use of the fluorene unit-based bicarbazole material as claimed in claim 1 as a light-emitting layer material of an OLED device.
10. Use of a biscarbazole material based on fluorene units according to claim 1 as electron transport material or hole transport material for organic devices.
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