CN101775010A - Carbazole-terminated heterofluorene main body material and preparation and application method - Google Patents
Carbazole-terminated heterofluorene main body material and preparation and application method Download PDFInfo
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Abstract
The invention discloses a carbazole-terminated heterofluorene main body material and a preparation and application method which is a general method for the carbazole-terminated heterofluorene main body material formed by introducing carbazole groups at the second and seventh sites or the third and sixth sites of heterofluorene. The carbazole-terminated heterofluorene main body material has the following basic structure, wherein X is one of heteroatoms such as nitrogen, oxygen, sulfur, phosphorus and the like; R1 and R2 are phenyl, alkyl (such as methyl, octyl and the like) with chain length of C1 to C18, thienyl and the like, or oxygen substituted group or are not existent; and R3 and R4 are one of ortho-para substituted groups such as methyl, alkoxyl, tertiary butyl and the like or are not existent.
Description
Technical field
The invention belongs to the photoelectric material technical field.Be specifically related to the preparation of the carbazole-terminated assorted fluorenes class material of a class, and relate to such material in the organic electroluminescent Application for Field.
Technical background
Since Tang research group of Kodak in 1987 and nineteen ninety univ cambridge uk Cavan enlightening permitted since the laboratory realized that organic molecule and polymer fluorescent material are made film-type organic electroluminescence device (Organic Light-emitting Diodes) and polymer LED (PolymericLight-emitting Diodes), the organic/polymer flat panel display has all had development at full speed at aspects such as material and devices.In order to realize the commercialization of organic/polymer electroluminescent device early, device has high quantum yield and can not be ignored.Because the restriction of spin statistics, the probability that current carrier is compounded to form singlet exciton in the small molecules organic electroluminescent fluorescent materials has only 25%, causes its external quantum efficiency generally can not surpass 5%.Replace fluorescent material with phosphor material, and the heavy metal atom of introducing can make lowest excited triplet state that original spin the prohibits transition (T to single line ground state in phosphor material
1-S
0) become permission, thus the energy of singlet and triplet excitons utilized simultaneously, be one of important channel of improving the organic electroluminescence device quantum yield.The phosphorescence guest materials makes the phosphorescence quantum yield reduce because concentration quenching and triplet state-triplet state are buried in oblivion (T-T annihilation) effect, thus in the phosphorescence device doped body material in the phosphorescence guest materials usually.The selection of material of main part is most important, should meet the following conditions: 1) singlet of material of main part and triplet energy state can be transferred to guest materials effectively; 2) absorption spectrum of the emmission spectrum of main body and object have bigger overlapping, i.e. energy level coupling; 3) material of main part has good carrier mobility character.
The triplet of carbazole (ET) is up to 3.05eV, so the carbazyl material is a present most widely used human subject material, and 4,4 '-N, N '-two carbazole biphenyl (CBP) they are the small molecules material of main parts that is most widely used at present.But the triplet energy state of CBP has only 2.67eV, can only be as the material of main part of ruddiness and green glow.Analyze from the CBP structure, two biphenyl planarityes of its intermediary are fine, make its triplet energy state energy reduce, thereby hindered its application as the blue light material of main part.Therefore, having a lot of researchs to focus on the middle cyclohexyl biphenyl of CBP at present increases steric group, reduces its effective conjugate length to improve its triplet, has obtained good achievement.As: 9,9 '-(1, the 3-phenyl) two-9H-carbazole (mCP), 4,4 '-two (9-carbazyl)-2, the triplet of 2 '-dimethyl-biphenyl (CDBP) has all reached 2.90eV.
As everyone knows, fluorenes also has high triplet energy state (2.95eV), and it is introduced the material of main part that can form high ternary energy level in the conjugated system as conjugate unit.Yet, assorted fluorenes is not but had patent report as the carbazole-terminated heterofluorene main body material that replaces the formation of CBP intermediary biphenyl group.Carbazole-terminated heterofluorene main body material shows following advantage: (1) assorted fluorenes class raw material or purchase price are cheap or be easy to make, and have high triplet energy state and good optical and electrical properties.(2) carbazole has advantages such as high triplet, strong cavity transmission ability, high thermostability and second-order transition temperature.Therefore, the present invention has developed a series of carbazole-terminated heterofluorene main body materials by simple synthetic route, has introduced simultaneously to have to increase solubleness or increase stable structural chain to enlarge the application of such material in organic electronic, photoelectron or photoelectric material.
Summary of the invention
Technical problem: preparation and its application method of the objective of the invention is to propose a kind of carbazole-terminated heterofluorene main body material.This method be with improved Ullmann prepared in reaction a series of carbazole-terminated assorted fluorenes class materials.In addition, pointed out the application of such material in phosphorescent organic electroluminescent device.
Technical scheme: carbazole-terminated heterofluorene main body material of the present invention has following general structure:
Wherein, X is a kind of in the heteroatomss such as nitrogen, oxygen, sulphur, phosphorus; R1, R2 are that phenyl, chain length are the alkyl (as methyl, octyl group etc.), thienyl of C1 ~ C18 etc., or for the oxygen substituting group or do not exist; R3, R4 are a kind of in the adjacency pair bit substituents such as methyl, alkoxyl group, the tertiary butyl, perhaps do not exist.
Above-claimed cpd of the present invention comparatively typically has following several:
R1, R2, R4 all do not exist, and X is a sulphur atom, and its structural formula is as follows:
Perhaps, R1 is an octyl group, and R2, R4 are and do not exist, and X is a nitrogen-atoms, and its structural formula is as follows:
Perhaps, R1 is a phenyl ring, and R2 does not exist, and R3 is a methoxyl group, and X is a phosphorus atom, and its structural formula is as follows:
Perhaps, R1, R2 are methyl, and R3 is an octyloxy, and X is a Siliciumatom, and its structural formula is as follows:
Perhaps, R1 is a phenyl ring, and R2 is that oxygen replaces, and R3 is the tertiary butyl, and X is a phosphorus atom, and its structural formula is as follows:
The synthetic method of the carbazole-terminated heterofluorene main body material that the present invention proposes is as follows:
The assorted fluorenes of (one) 2,7-dibromo is monomeric synthetic
The feature of utilizing butyllithium or magnesium can be under iodine and the simultaneous condition of bromine optionally to react with iodine, with 3,3 '-two replace-4,4 '-two bromo-6,6 '-diiodobiphenyl and butyllithium or reactive magnesium generate 3,3 '-two and replace-4,4 '-two bromo-6,6 '-two lithium biphenyl or 3,3 '-two replace-4,4 '-two bromo-6,6 '-two magnesium iodine biphenyl, this organo-metallic intermediate and the reaction of suitable dibasic heteroatoms just can obtain 2, the 7-dibromo fluorenes monomer of mixing;
(2) heterofluorene main body material of carbazole end group is synthetic
Utilize the Ullmann linked reaction can be with the assorted fluorenes coupling of carbazole and dibromo, this method is the catalytic amination reaction of copper, in the presence of Anhydrous potassium carbonate and catalytic amount copper, with oil of mirbane as solvent, temperature of reaction is 190 ℃, reaction times is 1 day, just can obtain high-purity target product through column chromatography and recrystallization;
Perhaps utilize butyllithium that the hydrogen on the carbazole is pulled out, and then react with the assorted fluorenes of dibromo, solvent is a tetrahydrofuran (THF), and temperature of reaction is a normal temperature, and the reaction times is 1-3 days, just can obtain pure target product through column chromatography and recrystallization equally;
Perhaps utilize the Buchward-Hartwing reaction, this catalysts is the palladium transition metal, and reaction conditions is an alkalescence, reaction solvent is toluene or dioxane, temperature of reaction is 120-180 ℃, and the reaction times is 1-3 days, just can obtain pure target product through column chromatography and recrystallization.
The application method of carbazole-terminated heterofluorene main body material is characterized in that can be used for the material of main part in the phosphorescent organic electroluminescent device.The mechanism of device is transparent anode/hole transmission layer/electronic barrier layer/material of main part and guest materials/electron transfer layer/electron injecting layer/negative electrode.
Beneficial effect: the heterofluorene main body material structure of carbazole end group is characterized by ultimate analysis, infrared spectra (FTIR), nucleus magnetic resonance (NMR), chromatograph mass spectrometer (GC-MS), ground substance assistant laser parsing time-of-fight mass spectrometry (MALDI-TOF); By ultraviolet-fluorescence (UV-PL), electrochemical analyser (CV) its optical physics performance is characterized; Thermostability by thermogravimetric analysis and differential thermal analysis test material.
Aspect the preparation of material, because raw material or purchase price are cheap or be easy to preparation, synthesis step is easy, and reaction yield height, this product tool aspect industrialization has great advantage.Aspect of performance at material, such material is in the fluorenes of having introduced high triplet, high triplet, high thermostability and the carbazole of second-order transition temperature have been introduced, make material have very high triplet and have good thermostability and solvability, can be used for the material of main part of phosphorescence electroluminescent device (PLED); In view of the fluorescence spectrum of part material in blue region, therefore can in organic electroluminescence device (OLED), be used as blue light material.
Description of drawings:
Fig. 1. be the carbazole-terminated micromolecular uv-absorbing spectrogram of dibenzothiophen;
Fig. 2. be carbazole-terminated dibenzothiophen small molecules fluorescence emission spectrum;
Fig. 3. be carbazole-terminated dibenzothiophen small molecules nuclear magnetic spectrogram.
Embodiment
Further specify technical scheme of the present invention below by embodiment, so that understand content of the present invention better.
Carbazole-terminated heterofluorene main body material of the present invention is characterized in that 2,7 or 3,6 introducing carbazole end groups at assorted fluorenes, has following structure:
Wherein, X is a kind of in the heteroatomss such as nitrogen, oxygen, sulphur, phosphorus;
R1, R2 are that phenyl, chain length are the alkyl (as methyl, octyl group etc.), thienyl of C1 ~ C18 etc., or for the oxygen substituting group or do not exist;
R3, R4 are a kind of in the adjacency pair bit substituents such as methyl, alkoxyl group, the tertiary butyl, perhaps do not exist.
Embodiment 1:
Synthesizing of carbazole-terminated dibenzothiophen
With carbazole, 3,6-dibromo dibenzothiophen, electrolytic copper powder, Anhydrous potassium carbonate adding are equipped with in two mouthfuls of flasks of stirrer, and described flask is dry and vacuumizes logical nitrogen airtight back three times, will use through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, reaction unit is put into oil bath pan, add oil of mirbane with syringe, oil of mirbane will be removed some impurity through strict processing before use.Whole reaction system is reacted 24h under reflux state.Reaction finishes, and after oil of mirbane is removed in underpressure distillation, also uses dichloromethane extraction three times with deionized water wash, and organic phase was spin-dried for silicagel column, obtains white solid.
Embodiment 2:
Synthesizing of carbazole-terminated carbazole
With carbazole, N-octyl-3,6-dibromo carbazole, electrolytic copper powder, Anhydrous potassium carbonate adding are equipped with in two mouthfuls of flasks of stirrer, described flask is dry and vacuumize logical nitrogen airtight back three times, will handle through strict anhydrous and oxygen-free device before high pure nitrogen uses and use.Then, reaction unit is put into oil bath pan, add oil of mirbane with syringe, oil of mirbane will be removed some impurity through strict processing before use.Whole reaction system is reacted 24h under reflux state.Reaction finishes, and after oil of mirbane is removed in underpressure distillation, also uses dichloromethane extraction three times with deionized water wash, and organic phase was spin-dried for silicagel column, obtains white solid.
Embodiment 3:
Synthesizing of carbazole-terminated phosphorus fluorenes
With 4,4 '-two bromo-, 6,6 '-two iodo-3, the adding of 3 '-dimethoxy-biphenyl is equipped with in the single port flask of stirrer, and described flask is dry and vacuumizes logical nitrogen airtight back three times, will use through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, with reaction unit as in ether and the dry ice bath, it is cooled to-100 ℃ and after adding butyllithium reaction half an hour under this temperature, add the dichlorophenyl phosphine, reaction is at normal temperatures spent the night, and uses dichloromethane extraction, obtain white solid 2 behind the column chromatography, 7-two bromo-3,6-dimethoxy-9, phenyl-phosphorus fluorenes.
With carbazole, 2,7-naled fluorenes, electrolytic copper powder, Anhydrous potassium carbonate adding are equipped with in two mouthfuls of flasks of stirrer, and described flask is dry and vacuumizes logical nitrogen airtight back three times, will use through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, reaction unit is put into oil bath pan, add oil of mirbane with syringe, oil of mirbane will be removed some impurity through strict processing before use.Whole reaction system is reacted 24h under reflux state.Reaction finishes, and after oil of mirbane is removed in underpressure distillation, also uses dichloromethane extraction three times with deionized water wash, and organic phase was spin-dried for silicagel column, obtains white solid.
Embodiment 4:
Synthesizing of carbazole-terminated silicon fluorenes
With 4, the adding of 4 '-two bromo-, 6,6 '-two iodo-, 3,3 '-two octyloxy biphenyl is equipped with in the single port flask of stirrer, and described flask is dry and vacuumizes logical nitrogen airtight back three times, will use through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, with reaction unit as in ether and the dry ice bath, it is cooled to-100 ℃ and after adding butyllithium reaction half an hour under this temperature, add dichlorodimethylsilane, reaction is at normal temperatures spent the night, and uses dichloromethane extraction, obtain white solid 2 behind the column chromatography, 7 two bromo-3,6-two octyloxies-9,9 '-dimethyl-silicon fluorenes.
With carbazole, 2,7-dibromo silicon fluorenes, electrolytic copper powder, Anhydrous potassium carbonate adding are equipped with in two mouthfuls of flasks of stirrer, and described flask is dry and vacuumizes logical nitrogen airtight back three times, will use through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, reaction unit is put into oil bath pan, add oil of mirbane with syringe, oil of mirbane will be removed some impurity through strict processing before use.Whole reaction system is reacted 24h under reflux state.Reaction finishes, and after oil of mirbane is removed in underpressure distillation, also uses dichloromethane extraction three times with deionized water wash, and organic phase was spin-dried for silicagel column, obtains white solid.
Embodiment 5:
Synthesizing of carbazole-terminated phosphorus oxide fluorenes
With 4,4 '-two bromo-, 6,6 '-two iodo-3, the adding of 3 '-tertiary butyl biphenyl is equipped with in the single port flask of stirrer, and described flask is dry and vacuumizes logical nitrogen airtight back three times, will use through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, with reaction unit as in ether and the dry ice bath, it is cooled to-100 ℃ and after adding butyllithium reaction half an hour under this temperature, add dichlorophenyl oxidation phosphine, reaction is at normal temperatures spent the night, and uses dichloromethane extraction, obtains white solid 2 behind the column chromatography, 7-two bromo-3,6-di-t-butyl-9-phenyl-phosphorus oxide fluorenes.
With carbazole, 2,7-dibromo phosphorus oxide fluorenes, electrolytic copper powder, Anhydrous potassium carbonate adding are equipped with in two mouthfuls of flasks of stirrer, and described flask is dry and vacuumizes logical nitrogen airtight back three times, will use through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, reaction unit is put into oil bath pan, add oil of mirbane with syringe, oil of mirbane will be removed some impurity through strict processing before use.Whole reaction system is reacted 24h under reflux state.Reaction finishes, and after oil of mirbane is removed in underpressure distillation, also uses dichloromethane extraction three times with deionized water wash, and organic phase was spin-dried for silicagel column, obtains white solid.
Embodiment 6:
The preparation of the phosphorescence electroluminescent device of carbazole-terminated heterofluorene main body material (CEHF)
The device architecture of a multilayer device is ITO/NPB (30nm)/CEHF:FIrpic or Ir (ppy)
3OrIr (piq)
2(40nm)/TPBI (40nm)/Mg:Ag (100nm)/Ag (100nm) wherein ITO be square resistance 10-20 Ω/cm
2Transparency electrode; CEHF adopts evaporation coating technique.
Claims (8)
1. carbazole-terminated heterofluorene main body material is characterized in that carbazole is introduced 2,7 or 3,6 of assorted fluorenes as end group, has following structure:
Wherein, X is a kind of in the heteroatomss such as nitrogen, oxygen, sulphur, phosphorus;
R1, R2 are that phenyl, chain length are the alkyl (as methyl, octyl group etc.), thienyl of C1～C18 etc., or for the oxygen substituting group or do not exist;
R3, R4 are a kind of in the adjacency pair bit substituents such as methyl, alkoxyl group, the tertiary butyl, perhaps do not exist.
2. carbazole-terminated heterofluorene main body material according to claim 1 is characterized in that: R1, R2, R4 all do not exist, and X is a sulphur atom, and its structural formula is as follows:
3. carbazole-terminated heterofluorene main body material according to claim 1 is characterized in that: R1 is an octyl group, and R2, R4 are and do not exist, and X is a nitrogen-atoms, and its structural formula is as follows:
4. carbazole-terminated foreign material human subject material according to claim 1, it is characterized in that: R1 is a phenyl ring, and R2 does not exist, and R3 is a methoxyl group, and X is a phosphorus atom, and its structural formula is as follows:
5. carbazole-terminated heterofluorene main body material according to claim 1 is characterized in that: R1, R2 are methyl, and R3 is an octyloxy, and X is a Siliciumatom, and its structural formula is as follows:
6. carbazole-terminated heterofluorene main body material according to claim 1 is characterized in that: R1 is a phenyl ring, and R2 is that oxygen replaces, and R3 is the tertiary butyl, and X is a phosphorus atom, and its structural formula is as follows:
7. the preparation method of a carbazole-terminated according to claim 1 heterofluorene main body material is characterized in that concrete preparation process is as follows:
Step 1: 2, the assorted fluorenes of 7-dibromo is monomeric synthetic
The feature of utilizing butyllithium or magnesium can be under iodine and the simultaneous condition of bromine optionally to react with iodine, with 3,3 '-two replace-4,4 '-two bromo-6,6 '-diiodobiphenyl and butyllithium or reactive magnesium generate 3,3 '-two and replace-4,4 '-two bromo-6,6 '-two lithium biphenyl or 3,3 '-two replace-4,4 '-two bromo-6,6 '-two magnesium iodine biphenyl, this organo-metallic intermediate and the reaction of suitable dibasic heteroatoms just can obtain 2, the 7-dibromo fluorenes monomer of mixing;
Step 2: the heterofluorene main body material of carbazole end group synthetic
Utilize the Ullmann linked reaction can be with the assorted fluorenes coupling of carbazole and dibromo, this method is the catalytic amination reaction of copper, in the presence of Anhydrous potassium carbonate and catalytic amount copper, with oil of mirbane as solvent, temperature of reaction is 190 ℃, reaction times is 1-3 days, just can obtain high-purity target product through column chromatography and recrystallization; Also can utilize butyllithium that the hydrogen on the carbazole is pulled out, and then react with the assorted fluorenes of dibromo, solvent is a tetrahydrofuran (THF), and temperature of reaction is a normal temperature, and the reaction times is 1-3 days, just can obtain pure target product through column chromatography and recrystallization equally; Can also utilize the Buchward-Hartwing reaction, this catalysts is the palladium transition metal, and reaction conditions is an alkalescence, reaction solvent is toluene or dioxane, temperature of reaction is 120-180 ℃, and the reaction times is 1-3 days, just can obtain pure target product through column chromatography and recrystallization.
8. the application method of a carbazole-terminated heterofluorene main body material as claimed in claim 1 is characterized in that this material of main part is used for the material of main part of phosphorescent organic electroluminescent device; The mechanism of device is transparent anode/hole transmission layer/electronic barrier layer/material of main part and guest materials/electron transfer layer/electron injecting layer/negative electrode.
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| JP2012099515A (en) * | 2010-10-29 | 2012-05-24 | Konica Minolta Holdings Inc | Organic electroluminescent element material, organic electroluminescent element and manufacturing method thereof, display, and luminaire |
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| CN103951705A (en) * | 2014-04-30 | 2014-07-30 | 华南理工大学 | Butterfly-shaped bipolar small molecular host material taking carbazole as core and preparation method thereof |
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| CN106188141B (en) * | 2016-07-01 | 2018-04-17 | 中节能万润股份有限公司 | A kind of OLED material and its application |
| CN107353302A (en) * | 2017-07-03 | 2017-11-17 | 南京邮电大学 | A kind of carborane derivative material based on carbazole and preparation method and application |
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Application publication date: 20100714 |