CN104017188B - Organic electroluminescence device main body material containing carbazole and triphenyl phosphine/phosphine oxide - Google Patents
Organic electroluminescence device main body material containing carbazole and triphenyl phosphine/phosphine oxide Download PDFInfo
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Abstract
The invention belongs to the field of organic electroluminescence and in particular relates to an organic electroluminescence device main body material containing carbazole and triphenyl phosphine/phosphine oxide. The main body material has a general structural formula as shown in the specification, in the formula, R1 is straight chain or branched alkyl chain with 1-12 carbon atoms, and R2 is phenyl, thienyl, alkyl substituted phenyl, alkyl substituted thienyl, alkyl, carbazolyl, alkyl substituted carbazolyl, fluorenyl, alkyl substituted fluorenyl, halogen atom or borate; x is more than 0 and less than 1, y is more than 0 and less than 1, and x+y=1; and n is a positive integer. According to the main body material, carbazole with good hole transmission performance is adopted as a hole transmission unit, and a triphenyl phosphine group or a triphenyl phosphine oxide group with good electron transmission capability is adopted as an electron transmission unit, so that the charge transfer balance is facilitated; and meanwhile, phosphorus atoms and modified 9-phenylcarbazole are favorable for reducing the conjugation degree of main polymer chains and increasing the triplet state energy level of polymers.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, more particularly, to one class contains having of carbazole and triphenyl phosphorus/phosphorus oxygen
Organic electroluminescence devices material of main part.
Background technology
Organic Light Emitting Diode (OLED) is considered as illumination of future generation and full developing technology.At present, report is the most efficient
The luminescent device of rate is realized based on full phosphorescent emissions Organic Light Emitting Diode, and higher SO coupling efficiency makes
Obtain phosphorescent emissive material and not only using singlet exciton but also can utilize triplet excitons, so that internal quantum efficiency is resonable
By 100% above can be reached.But, for current blue emitting phosphor luminescent device, remain restriction Organic Light Emitting Diode development
One bottleneck.It is possible, firstly, to the outstanding blue phosphor materials for Organic Light Emitting Diode are limited.At present, most popular
Blue light material is that double (4,6- difluorophenyl pyridinato-N, C2) pyridinecarboxylic close iridium (III) (FIrpic, triplet 2.62eV),
But this material is sky blue.Secondly, can be less as the material of main part of Organic Light Emitting Diode blue phosphorescent.Blue phosphorescent material
Material is frequently not directly used in the emission layer preparing Organic Light Emitting Diode, and is dispersed in material of main part, so just can keep away
Exempt from triplet state to be quenched and concentration quenching.This triplet state energy requiring material of main part and the triplet state being higher than blue emitting phosphor material
Energy level could effectively avoid energy to be returned from phosphor material to material of main part.With most popular blue light dopant material at present
Must be requested that the triplet of material of main part could effectively suppress the passback of energy higher than 2.65eV for FIrpic.
Prepare the conventional material of main part of Organic Light Emitting Diode and include small molecule and macromolecule two class.At present, high efficiency has
The small molecule host material that machine LED device mainly adopts.Although the efficiency of small molecule Organic Light Emitting Diode is than high
The efficiency of mulecular luminescence diode is generally high, but preparation small molecule Organic Light Emitting Diode often uses evaporation skill
Art, complex process time consumption and energy consumption and relatively costly.Solwution method is considered as to be best suitable at this stage preparing organic light emission two on a large scale
The technology of pole pipe, such technical matters are simple and low cost.But existing macromolecule material of main part is using fluorenes or carbazole as knot
Structure unit, has that triplet is low and the unbalanced problem of carrier transport.
In consideration of it, the polymer host material that high triplet energy level was processed, had to the suitable solwution method of synthesis is that solution is organic
Light emitting diode bottleneck urgent problem.
Content of the invention
In order to solve the above problems, present invention aim at provide being beneficial to the raising of triplet and the increase of stability
The organic electroluminescence device material of main part containing carbazole and triphenyl phosphorus/phosphorus-oxygen groups compound.
The technical scheme is that：Organic electroluminescence device main body material containing carbazole and triphenyl phosphorus/phosphorus-oxygen groups
The compound of material, the structural formula of this compound is as follows：
The compound of the organic electroluminescence device material of main part containing carbazole and phosphorus atoms, the general structure of this polymer
For： Wherein,
R in formula1Straight chain for 1 to 12 carbon atoms or branched alkyl chain, R2For phenyl, thienyl, the phenyl of alkyl replacement, thiophene
Base, fluorenyl, halogen atom or borate that alkyl, carbazyl, the carbazyl of alkyl replacement, fluorenyl, alkyl replace；0 ＜ x ＜ 1,0
＜ y ＜ 1, and x+y=1；N value is positive integer.
Preferably, when x and y is 0.5, described compound has formula P1 structure：
P1
Preferably, when x and y is 0.5, described compound has formula P2 structure：
P2
The invention has the beneficial effects as follows, due to adopting technique scheme, the polymer of the present invention has advantages below：
1) carbazole and triphenyl phosphorus/phosphorus-oxygen groups have higher hole and electronic transmission performance, and carbazole has relatively
High triplet (3.01V)；
2) introducing of triphenyl phosphorus/phosphorus-oxygen groups can form tetrahedral structure, effectively interrupts being total to of high polymer main chain
Yoke, makes polymer have higher triplet, and so that high polymer main chain is distorted, and weakens intermolecular π-π intermolecular interaction, and
And hinder intermolecular accumulation and crystallization, increased the rigidity of molecule, can effectively increase the stability after film forming；
3) make after introducing phenyl on the N of rigid carbazole group 9 between side chain and main chain, certain distortion, beat
Interaction between disconnected side chain and main chain, and the conjugation between side chain and main chain is interrupted；
4) alkyl chain that phenyl connects can effectively increase the dissolubility of molecule, and provides for accessing other groups
Site.The increase of all these raisings, deliquescent improvement and stability being all conducive to triplet.
Brief description
Fig. 1 is the polymer P 1 and P2 ultra-violet absorption spectrum in dichloromethane solution and thin film and fluorescence emission spectrum.
Fig. 2 is the polymer P 1 and P2 phosphorescent emissions in 2- methyltetrahydrofuran under 77K.
Fig. 3 is the cyclic voltammetry curve of polymer P 1 and P2.
Specific embodiment
Below by specific embodiment, the present invention is described further, and specific examples below is in order to better illustrate
The present invention but be not intended to limit the present invention.
Embodiment 1:
The synthesis of M1
250ml flask adds to iodophenol (22g, 100mmol), 1- bromooctane (25.09g, 130mmol), carbonic acid
Potassium (18g, 130mmol), acetone 100ml, backflow lower reaction overnight, then solvent is evaporated, is obtained by extraction with dichloromethane
Organic faciess anhydrous sodium sulfate drying, obtains viscous liquid, obtains 1- iodo- 4- (octyloxy) benzene 33g (yield through chromatographic column
99%).1H NMR(400MHz,CDCl3) δ=7.52 (d, J=8.8,2H), 6.65 (d, J=8.8,2H), 3.88 (t, J=
6.5,2H), 1.90 1.78 (m, 2H), 1.41 (s, 2H), 1.27 (s, 8H), 0.87 (t, J=6.3,3H).
By 3,6- dibromo carbazole (10g, 28mmol), 1- iodo- 4- (octyloxy) benzene (14.4g, 33mmol), Hydro-Giene (Water Science).
(285mg, 1.5mmol) tripotassium phosphate (6.4g, 30mmol), trans 1,6- cyclohexanediamine (3mol, 370ul) are added to 250ml
In flask, add toluene (100mL), the lower backflow of argon protection 40 hours.Stop heating, be cooled to room temperature, solvent is evaporated, use
Dichloromethane extracts, and after organic faciess anhydrous sodium sulfate drying, solvent evaporated obtains M1 12g by column chromatography, and yield is
80.7%.
1H NMR(400MHz,CDCl3) δ=8.33 (d, J=20.4,0.4H), 8.13 (d, J=18.9,1.6H), 7.66
(d, J=23.7,0.4H), 7.50 (d, J=24.2,1.6H), 7.33 (s, 1H), 7.24 (s, 1H), 7.15 (s, 1H), 7.07
(s, 1H), 4.27 (d, J=55.1,1H), 3.96 (d, J=57.7,1H), 1.83 (s, 2H), 1.49 (s, 1H), 1.26 (d, J=
33.1,9H), 0.87 (d, J=14.8,3H).
MS(MALDI-TOF)：m/z C26H27Br2NO theoretical value 529.3；Measured value 529.1 (M+).
Reaction equation is as follows：
The synthesis of M2
At -78 DEG C, in the tetrahydrofuran solution of Isosorbide-5-Nitrae-dibromobenzene (14.2g, 60mmol) Deca n-BuLi (1.6M's
Hexane solution) 26.25mL, it is incubated 1.5 hours under argon protection, then Deca phenyl dichloro phosphine (5.9g, 4.5mL), drips
Add Bi Houzai to react 1.5 hours at -78 DEG C, be then transferred into being stirred overnight under room temperature.Solvent is evaporated, uses dichloromethane
Extraction, uses anhydrous sodium sulfate drying organic faciess, removes solvent, obtains double (4- bromophenyl) (phenyl) phosphine 10g through chromatographic column,
Yield 79.3%.1H NMR(400MHz,CDCl3) δ=7.46 (d, J=7.7,4H), 7.35 (d, J=4.1,3H), 7.27 (d, J
=7.5,2H), 7.13 (t, J=7.6,4H).13C NMR(101MHz,CDCl3) δ=135.98,135.92,135.86,
135.28,135.07,133.77,133.57,131.86,131.79,129.25,128.83,128.76,123.69.
Double (4- bromophenyl) (phenyl) phosphine (8g, 18mmol) are dissolved in 100ml oxolane, are cooled to -78, the positive fourth of Deca
Base lithium (hexane solution of 1.6M) 20mL, argon protection reaction 1.5h, allows rear Deca 2- isopropoxy -4 at this temperature, and 4,
5,5- tetramethyl -1,3,2- di (hetero) oxygen pentaborane (9.8mL, 45mmol), after completion of dropping, it is badly in need of reaction 1.5h, then give birth to extremely
Room temperature reaction is overnight.Oxolane is evaporated, obtains the solid M2 7.2g of white, yield 77.8% by column chromatography.1H NMR
(400MHz,CDCl3) δ=7.86 (d, J=6.5,0.6H), 7.73 (d, J=7.6,3H), 7.68 7.58 (m, 1H), 7.55
7.47 (m, 0.3H), 7.42 (t, J=7.8,0.3H), 7.31 7.25 (m, 7.8H), 1.31 (s, 24H).13C NMR(101MHz,
CDCl3) δ=140.65,140.53,134.64,134.58,134.04,133.85,133.01,132.82,128.87,
128.56,128.45,83.81,24.81.MS(MALDI-TOF)：m/z C30H37B2O4P theoretical value 512.2；Measured value
513.2(M++1).
Reaction equation is as follows：
The synthesis of P1
By monomer M1 (0.50g, 0.9450mmol), monomer M2 (0.4860g, 0.9450mmol), wet chemical
(2M, 5mL), methyl tricapryl ammonium chloride (Aliquat 336), a tetra-triphenylphosphine palladium (Pd (PPh3)4, 21.8mg) and
20ml toluene is added in 50ml twoport flask, under argon protection, reacts 48 hours under the conditions of 90 DEG C of lucifuges.It is subsequently adding benzene
The deoxidation toluene solution (5mL) of boric acid (100mg) and bromobenzene (0.5mL), reaction respectively is blocked for 12 hours.It is cooled to room
Temperature, mixing liquid is imported in methanol, and the precipitation of generation is extracted with dichloromethane after filtering, is had with anhydrous sodium sulfate drying
Machine phase, after carrying out being concentrated to give suitable volume, is precipitated with methanol extraction.Precipitation is used in apparatus,Soxhlet'ses after collecting divides
Normal hexane, methanol extracting Yong not remove small molecule and catalyst, finally be extracted with chloroform.The solution obtaining uses three after concentrating
Chloromethanes/methanol extraction, obtain white fibrous solid 0.4g, yield 67%.1H NMR(400MHz,CDCl3) δ=8.79
8.17(m,1H),7.67(s,13H),7.43(s,6H),7.14–6.98(m,2H),4.05(s,2H),1.83(s,2H),1.52–
1.40 (m, 2H), 1.32 1.18 (m, 8H), 0.98 (t, J=7.2,3H).13C NMR(101MHz,CDCl3) δ=145.68,
140.13,138.58,134.72,132.17,132.10,132.01,128.96,128.56,128.44,127.28,121.73,
121.02,114.35,59.16,31.88,29.74,29.50,29.33,26.15,24.19,22.60,19.90,14.12,
13.74. elementary analysiss：(C44H40NOP)nTheoretical value C 83.94, H 6.36, N 2.22；Measured value C84.35, H 6.49, N
1.97.
Reaction equation is as follows：
Embodiment 2：
The synthesis of M1
250ml flask adds to iodophenol (22g, 100mmol), 1- bromooctane (25.09g, 130mmol), carbonic acid
Potassium (18g, 130mmol), acetone 100ml, backflow lower reaction overnight, then solvent is evaporated, is obtained by extraction with dichloromethane
Organic faciess anhydrous sodium sulfate drying, obtains viscous liquid, obtains 1- iodo- 4- (octyloxy) benzene 33g (yield through chromatographic column
99%).1H NMR(400MHz,CDCl3) δ=7.52 (d, J=8.8,2H), 6.65 (d, J=8.8,2H), 3.88 (t, J=
6.5,2H), 1.90 1.78 (m, 2H), 1.41 (s, 2H), 1.27 (s, 8H), 0.87 (t, J=6.3,3H).
By 3,6- dibromo carbazole (10g, 28mmol), 1- iodo- 4- (octyloxy) benzene (14.4g, 33mmol), Hydro-Giene (Water Science).
(285mg, 1.5mmol) tripotassium phosphate (6.4g, 30mmol), trans 1,6- cyclohexanediamine (3mol, 370ul) are added to 250ml
In flask, add toluene (100mL), the lower backflow of argon protection 40 hours.Stop heating, be cooled to room temperature, solvent is evaporated, use
Dichloromethane extracts, and after organic faciess anhydrous sodium sulfate drying, solvent evaporated obtains M1 12g by column chromatography, and yield is
80.7%.
1H NMR(400MHz,CDCl3) δ=8.33 (d, J=20.4,0.4H), 8.13 (d, J=18.9,1.6H), 7.66
(d, J=23.7,0.4H), 7.50 (d, J=24.2,1.6H), 7.33 (s, 1H), 7.24 (s, 1H), 7.15 (s, 1H), 7.07
(s, 1H), 4.27 (d, J=55.1,1H), 3.96 (d, J=57.7,1H), 1.83 (s, 2H), 1.49 (s, 1H), 1.26 (d, J=
33.1,9H), 0.87 (d, J=14.8,3H).
MS(MALDI-TOF)：m/z C26H27Br2NO theoretical value 529.3；Measured value 529.1 (M+).
Reaction equation is as follows：
The synthesis of M3
By double for phenyl 4- (4,4,5,5- tetramethyl -1,3,2- dioxy boron penta ring -2- base) Phenylphosphines (M2) (5.16g,
10mmol), Iron(III) chloride hexahydrate (305.4mg, 0.791mmol), thiocyanation ferrum (230.64mg, 2.37mmol), catalytic amount
Iodine be added in 100ml flask, add 60mL acetonitrile, under the continuous air-blowing of oxygen, 80 DEG C react 30 minutes, after finishing cool down
To room temperature.Solvent is evaporated, white solid M3 5g, yield 94% are obtained by column chromatography.1H NMR(400MHz,CDCl3) δ=
7.85 (d, J=5.7,4H), 7.70 7.56 (m, 6H), 7.53 7.47 (m, 1H), 7.42 (d, J=6.7,2H), 1.32 (s,
24H).13C NMR(101MHz,CDCl3) δ=135.57,134.60,134.55,134.48,132.14,132.04,131.97,
131.25,131.15,128.55,128.43,84.20,24.87.MS(MALDI-TOF)：m/z C30H37B2O5P theoretical value
530.2；Measured value 531.2 (M++1).
The synthesis of P2
By monomer M1 (0.5293g, 1.0mmol), monomer M3 (0.5302g, 1.0mmol), wet chemical (2M,
5mL), methyl tricapryl ammonium chloride (Aliquat 336), a tetra-triphenylphosphine palladium (Pd (PPh3)4, 23.1mg) and 20ml first
Benzene is added in 50ml twoport flask, under argon protection, reacts 48 hours under the conditions of 90 DEG C of lucifuges.It is subsequently adding phenylboric acid
(100mg) deoxidation toluene solution (5mL) and bromobenzene (0.5mL), reaction respectively is blocked for 12 hours.It is cooled to room temperature, will
Mixing liquid imports in methanol, and the precipitation of generation is extracted with dichloromethane after filtering, uses anhydrous sodium sulfate drying organic faciess,
After carrying out being concentrated to give suitable volume, it is precipitated with methanol extraction.Precipitation is used in apparatus,Soxhlet'ses after collecting and uses respectively
Normal hexane, methanol extracting remove small molecule and catalyst, are finally extracted with chloroform.The solution obtaining uses three chloromethanes after concentrating
Alkane/methanol extraction, obtains white fibrous solid 0.45g, yield 69.4%.1H NMR(400MHz,CDCl3) δ=8.41 (s,
1H), 8.28 (d, J=18.7,1H), 7.74 (d, J=51.7,11H), 7.45 (dd, J=28.0,20.1,8H), 7.10 (s,
2H),4.04(s,2H),1.83(s,2H),1.45–1.11(m,10H),0.88(s,3H).13C NMR(101MHz,CDCl3) δ=
145.60,145.35,144.08,141.51,132.91,132.71,132.13,129.04,128.67,128.50,128.29,
127.36,126.98,126.00,119.11,118.15,115.81,110.31,68.29,31.88,29.38,26.15,
22.68,14.25.Elementary analysiss：(C44H40NO2P) n theoretical value C 80.12, H 6.07, N 2.12；Measured value C, 80.97；H
5.86；N 2.01.
Reaction equation is as follows：
Polymer performance characterizes：
The spectral quality of polymer P 1 and P2, electrochemical properties
1) spectral quality of compound P1 and P2
Fig. 1 is the polymer P 1 and P2 uv absorption in dichloromethane and thin film and fluorescence emission spectrum.As shown in Figure 1
In the solution of polymer P 1 and P2, ultraviolet absorption peak is located at 225nm and 303nm, and maximum emission peak is respectively in 387 Hes
393nm.Maximum absorption band in thin film is located at 285 and 303nm about respectively, and maximum emission peak is located at 410 and 428nm.By P1
Being calculated both and carry with the absorption edge of P2 filminess is (Eg) it is respectively 3.18 and 3.26eV.Fig. 2, by the phosphorus under 77K
Light spectrum can obtain the triplet (E of P1 and P2T) for 2.72eV, (triplet is according to formula ET=1240/ λ calculates
Obtain, wherein λ is the peak position of first emission peak of phosphorescence emission spectra), the high triplet of polymer P 1 and P2 can meet
Requirement as organic electroluminescence device material of main part.
2) electrochemical properties of compound P1 and P2
Fig. 3 is the cyclic voltammetry curve of polymer P 1 and P2.Electrolyzer adopts three-electrode system, with platinum carbon electrode for work
Electrode, platinum filament is to electrode, and silver/silver chloride electrode is reference electrode, and tetrabutyl ammonium hexafluorophosphate is as supporting electrolyte.Scanning
Speed is per second for 100 millivolts.Show that polymer P 1 and the initial oxidation current potential of P2 are respectively 1.05 Hes by cyclic voltammetry curve
1.15V, thus calculates HOMO energy level and is respectively -5.42 and -5.52V (ferrocene is internal standard, correcting potential 0.43V).Foundation
HOMO and EgObtain LUMO and be respectively -2.24 and -2.26eV.
Claims (3)
1. contain the organic electroluminescence device material of main part of carbazole and triphenyl phosphorus/phosphorus oxygen it is characterised in that the knot of this polymer
Structure formula is：、、
Or；
Wherein, R in formula1Straight chain for 1 to 12 carbon atoms or branched alkyl chain, R2For phenyl, the phenyl of alkyl replacement, thiophene
Fen base, fluorenyl, halogen atom or borate that alkyl, carbazyl, the carbazyl of alkyl replacement, fluorenyl, alkyl replace；0 ＜ x ＜ 1,
0 ＜ y ＜ 1, and x+y=1；N value is positive integer.
2. the organic electroluminescence device material of main part containing carbazole and triphenyl phosphorus/phosphorus oxygen according to claim 1, it is special
Levy and be, work as x=0.5, y=0.5, the structural formula of this material of main part（P1）, as follows：
Formula P1.
3. the organic electroluminescence device material of main part containing carbazole and triphenyl phosphorus/phosphorus oxygen according to claim 1, it is special
Levy and be, work as x=0.5, y=0.5, the structural formula of this material of main part（P2）, as follows：
Formula P2.
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