CN102993417B - Quaternary ammonium salt group containing organic semiconductor material and applications thereof - Google Patents
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Abstract
The invention discloses a quaternary ammonium salt group containing organic semiconductor material and applications thereof in OLED (organic light emitting diode) devices. A side chain of the quaternary ammonium salt group containing organic semiconductor material disclosed by the invention is provided with quaternary ammonium salt polar groups, so that the material can be dissolved in polar solvents such as methanol and ethanol and hardly soluble in solvents such as toluene and the like. The quaternary ammonium salt group containing organic semiconductor material can be used as a hole injection layer material and applied to OLED devices.
Description
Technical field
The present invention relates to photoconductive organic semiconductor Material Field, particularly relate to a kind of organic semiconductor material containing quaternary ammonium salt group, and the application in the hole injection layer of OLED.
Background technology
As shown in Figure 1, OLED is formed primarily of negative electrode 1, luminescent layer 2, hole injection layer (HIL) 3, anode 4, substrate 5 stacked above one another, and power supply 6 connects negative electrode 1 and anode 4.Described luminescent layer 2 is organic materials.During preparation OLED, tin indium oxide (ITO) is normally first set on substrate 5 as anode 4, then hole injection layer (HIL) 3 is set on ito anode 4, then luminescent layer 2 is set on hole injection layer 3, last on luminescent layer 2 evaporation metal negative electrode 1 again, such as successively vacuum evaporation one deck CsF and layer of metal Al jointly as negative electrode 1.The method arranging luminescent layer 2 utilizes spin-coating method usually, specific practice luminous organic material is dissolved in obtained Organic luminescent material solution in toluene equal solvent, then by Organic luminescent material solution rotary coating on hole injection layer 3, in order to avoid hole injection layer 3 dissolves or corrodes by the toluene equal solvent in Organic luminescent material solution, thus affect the working effect of OLED, so can only select insoluble or be insoluble in the material of organic materials as hole injection layer 3 of toluene equal solvent.
At present, selectable hole injection layer organic materials is little, and conventional hole injection layer material mainly contains two kinds, and one is poly-(3,4-ethylenedioxy thiophene) and the mixture aqueous solution (PEDOT:PSS) of poly styrene sulfonate, another kind is Polyvinyl carbazole (PVK).Wherein conventional with PEDOT:PSS again, but PEDOT:PSS is a kind of acidic solution in fact, has certain corrosive nature to ito anode, so adopt PEDOT:PSS can reduce life-span and the stability of OLED as hole injection layer.And due to PVK be the unconjugated polymkeric substance of a kind of main chain, its specific conductivity is not high, so the hole injection/transmission performance of PVK is not so good, this is also one of unfavorable factor affecting OLED performance.
Summary of the invention
The object of the invention is to the defect overcoming prior art, provide a kind of can as the hole injection layer material of OLED containing the organic semiconductor material of quaternary ammonium salt group.
Technical solution of the present invention is: a kind of organic semiconductor material containing quaternary ammonium salt group, and structural formula is:
Wherein, 0<x<1,0<y<1, x+y=1; N is the polymerization degree of described organic semiconductor material, and n is the natural number of 1 ~ 10000; R
1, R
2, R
3, R
4, R
5, R
6for the alkyl of C1 ~ C4.
Preferably, described R
1, R
2, R
3, R
4, R
5, R
6for ethyl.
The described application of organic semiconductor material in the hole injection layer of OLED containing quaternary ammonium salt group.
The side chain of the organic semiconductor material containing quaternary ammonium salt group of the present invention is with quaternary ammonium salt polar group, make this material can be dissolved in polar solvent as in methyl alcohol, ethanol, and be insoluble in again toluene equal solvent, therefore the described organic semiconductor material containing quaternary ammonium salt group can as the hole injection layer material of OLED.
Advantage of the present invention is:
(1) organic semiconductor material containing quaternary ammonium salt group of the present invention can as the hole injection layer material of OLED, for the selecting of hole injection layer material of OLED provides more more options.
(2) organic semiconductor material containing quaternary ammonium salt group of the present invention does not have acid corrosion effect to ito anode, is conducive to the extensive industrialization of OLED.
(3) main polymer chain of the organic semiconductor material containing quaternary ammonium salt group of the present invention is conjugation, main polymer chain is formed by the carbazole group and trianilino group copolymerization with good hole injection/transmission performance, there is higher specific conductivity, be conducive to injection and the transmission in hole in OLED.
Accompanying drawing explanation
Fig. 1 is OLED structural representation;
Fig. 2 is using the PCTN-Br of embodiment 12 preparation as hole injection layer (HIL) material, is the OLED of ITO/HIL/P-PPV/CsF/Al making and the current efficiency-current density plot figure of control device thereof by device architecture;
1, negative electrode, 2, luminescent layer, 3, hole injection layer, 4, ito anode, 5, substrate, 6, power supply.
Embodiment
Synthetic route 1 is as follows:
Embodiment 1:
The preparation of the bromo-2 nitro biphenyl of 4,4-bis-(1)
Be dissolved in by 4,4-'-dibromobiphenyl (20g, 64mmol) in glacial acetic acid (300mL), heated and stirred at 110 DEG C, drip concentrated nitric acid (70%, 132mL) in glacial acetic acid, 6h is until solid slowly dissolves in heating, is then cooled to room temperature.By reacting liquid filtering, solid washed with water, then obtains yellow solid (17.6g, yield77%) with ethyl alcohol recrystallization.
1 h-NMR (300MHz, CDCl
3 ): (ppm) 8.32 (d, 2H), 8.29 (d, 2H), 7.77 (dd, 2H).
Embodiment 2:
The preparation of 2,7-dibromo carbazole (2)
Compound 1(16.5g, 46.1mmol will be added with) triethyl phosphate (60mL) reflux 18h under nitrogen protection.By reaction solution underpressure distillation removing excessive solvent, a small amount of methylene dichloride of residuum dissolves, and then settling out with sherwood oil obtains head product, then obtains white solid (9.28g, yield 62%) with silica gel/sherwood oil column chromatography.
1 H-NMR(300MHz, CDCl
3 ): δ(ppm) 8.20 (br，1H，NH); 7.92 (d，2H); 7.56 (d，2H); 7.35 (dd，2H)。
Embodiment 3:
The preparation of the bromo-6-hexyl ether (3) of p-methylphenyl-1-
P-methyl phenol (28g), 1,6-dibromo-hexane (220mL), salt of wormwood (60g), Tetrabutyl amonium bromide (3.8g) and acetone (150mL) is added, heated and stirred backflow 48h in 500mL flask.Room temperature is down in reaction, and filter, filtrate is threaded to quality with water circulating pump and no longer reduces, and then uses oil pump underpressure distillation, collects 210 DEG C ~ 220 DEG C cuts and is colorless oil as product (53.5g, yield76.1%).
1 h-NMR (300MHz, CDCl
3 ): δ (ppm) 7.10 (d, 2H); 6.82 (d, 2H); 3.96(t, 2H); 3.45(t, 2H); 2.32(s, 3H); 1.8(br, 8H).
Embodiment 4:
The preparation of 1,13-bis-(to methylphenoxy)-7-tridecanol (4)
Compound is added in there-necked flask (100mL)
3(16.1g, 60mmol), THF(60mL) and brand-new magnesium rod (1.44g, 60mmol), under nitrogen protection reflux 3h, room temperature is down in reaction.Ethyl formate (1.48g is added in three neck round-bottomed flasks (250mL) of drying, 20mmol) and THF(100mL), then subzero 78 DEG C are cooled to, then extract the stillness of night in there-necked flask (100mL) out with minute hand head and dropwise add in three neck round-bottomed flasks (250mL), maintain reaction and react 1h at subzero 78 DEG C, then at room temperature stir and spend the night.Add methyl alcohol cancellation reaction, then add saturated ammonium chloride solution, use petroleum ether extraction reaction solution, extraction liquid saturated nacl aqueous solution washes three times, extraction liquid dried over mgso.Then extraction liquid underpressure distillation is obtained white solid product (21.07 g, yield 82 %).
1h-NMR (300MHz, CDCl
3): δ (ppm) 7.10 (d, 4H); 6.82 (d, 4H); 3.96(t, 4H); 3.6 (br, 1H); 2.26 (d, 6H); 1.5 (m, 21H),
13c-NMR (75MHz, CDCl
3): δ (ppm) 157.00,129.84,129.66,114.40,77.44,77.22,77.02,76.60,71.91,68.00,37.42,29.44,29.28,26.05,25.57,20.43.
Embodiment 5:
Tosic acid-7-{1,13-bis-(to methylphenoxy) } preparation of tridecyl ester (5)
Compound is added in the 250 mL flasks that methylene dichloride (30mL) is housed
4(6.0g, 14.55mmol), triethylamine (5.1mL) and trimethylamine hydrochloride (1.38 g, 14.55 mmol), control the temperature of dichloromethane solution 0 – 5 DEG C, the dichloromethane solution (30mL) of p-methyl benzene sulfonic chloride (4.16g, 21.8mmol) is added drop-wise in flask, stirring reaction 90 minutes, then the cancellation that adds water is reacted, reaction solution dichloromethane extraction three times, organic phase washed with water and salt washing, then use dried over mgso.Then underpressure distillation is except desolventizing, and head product silica gel/sherwood oil column chromatography obtains white solid (6.5g, yield 78.8 %).
1h-NMR (300MHz, CDCl
3): δ (ppm) 7.79 (d, 2H); 7.31 (d, 2H); 7.10 (d, 4H); 6.82 (d, 4H); 4.56 (m, 1H); 3.96(t, 4H); 2.46 (s, 3H); 2.31 (s, 6H); 1.51 (m, 17H).
13c-NMR (75MHz, CDCl
3): δ (ppm) 156.93,144.39,134.70,129.87,129.70,129.67,127.72,1144.32,84.37,67.85,34.09,29.16,29.04,25.86,24.64,21.60,20.47.
Embodiment 6:
The preparation of N-7 '-{ 1 ', 13 '-two (to methylphenoxy) } tridecyl-2,7-dibromo carbazole (6)
Compound is added in three-necked flask
2(6.500 g, 20.00 mmol), DMSO (30 mL) and fresh potassium hydroxide powder (5.611 g, 100.0 mmol), work as compound
2after dissolving completely, at room temperature add compound by dropping funnel
5dMSO (50 mL) solution of (17.0g, 30.00 mmol), controls time for adding at 1.5 – 2 h.After continuing reaction 6h, reaction solution is poured in distilled water (300 mL), extracts three times, then wash with water repeatedly by extraction liquid, organic phase dried over mgso with sherwood oil (350 mL).Then the solvent of decompression removing organic phase, residuum methylene dichloride dissolves again, obtains thick liquid (11.1g, yield:77.0%) with silica gel/sherwood oil column chromatography.
1 H-NMR(300MHz,CDCl
3): δ(ppm) 7.89 (t，2H); 7.60 (d，2H); 7.34 (dd，2H); 7.04(d,4H); 6.75(d,4H); 4.40(m,1H); 3.80(t,4H); 2.28(s,6H); 1.5(m,20H).
13C-NMR(75MHz, CDCl
3):δ(ppm)156.92，129.81，129.65，122.43，121.53，121.29，119.82，119.22，114.36，112.08，68.04，67.81，56.99，33.44，29.11，29.04，26.70，25.77，20.43。
Embodiment 7:
The preparation of N-7 '-(1 ', 13 '-dibromo) tridecyl-2,7-dibromo carbazole (7)
Compound is added in 250mL there-necked flask
6(11g, 15.2mmol), Hydrogen bromide (60g, 50%) and glacial acetic acid 180mL, reflux 48h, reaction solution is poured in water (300mL), repeatedly extracts with methylene dichloride, and organic phase washed with water and solution of potassium carbonate are washed, and then use dried over mgso.Then removal of solvent under reduced pressure, obtains white solid (7.7g, yield76.2%) with silica gel/sherwood oil column chromatography.
1 H-NMR(300MHz, CDCl3): δ(ppm) 7.89 (t,2H); 7.60 (d,2H); 7.34 (d,2H); 4.41(m,1H); 3.30(t,4H); 2.08(m,4H); 1.72(m,4H); 1.2(m,4H).
13C-NMR(75MHz, CDCl
3): δ(ppm) 122.50，121.59，121.34，119.86，119.25，114.42，112.03，56.83，33.79，33.33，32.49，28.37，27.79，26.52。
Embodiment 8:
The preparation of N-7 '-{ 1 ', 13 '-two (N, N dimethylamine base) } tridecyl-2,7-dibromo carbazole (M1)
Compound is added in 250mL there-necked flask
7(15g, 22.6mmol), DMF(50mL) and diethylamine (82.4,1130mmol), reflux 6h.Stopped reaction, pours in 250mL water by reaction solution, with dichloromethane extraction, organic phase sodium carbonate dilute solution washes three times, then dried over mgso; Then underpressure distillation is except desolventizing, obtains weak yellow liquid (12.5g, yield:85.6%) with silica gel/sherwood oil (adding triethylamine) column chromatography.
1 H-NMR(300MHz, CDCl
3):δ(ppm)7.89(t,2H); 7.60(d,2H); 7.34(d,2H); 4.41(m,1H); 2.43(q,8H); 2.25(t,4H); 2.00(m,4H); 1.20(m,16H); 0.91(t,12H).
13C-NMR(75MHz, CDCl
3): δ(ppm)122.10, 121.50, 121.40, 119.45, 114.44, 112.10, 56.98, 52.60, 46.90, 33.55, 29.31, 29.20, 27.30, 26.90, 11.60。
Synthetic route 2 is as follows:
Embodiment 9:
4,4 '-dibromo triphenylamine (8) preparation
Under lucifuge and argon shield condition, 2.45g triphenylamine (10mmol) being joined in a dry three-necked bottle, simultaneously by 3.56g(20mmol) N-bromo-succinimide (N-bromosuccinimide is called for short NBS) is as in constant pressure funnel.Add 20mL methylene dichloride dissolved solids respectively, then with frozen water mixing bath, system temperature is reduced to 0 DEG C, NBS is slowly dropped in three-necked bottle and also constantly stir, drip rear continuation and keep low-temp reaction 1 hour.After reaction terminates, reaction solution is poured in 100mL distilled water, use CH
2 cl
2 extraction, after combining extraction liquid, rotary evaporation is except desolventizing, with sherwood oil as eluent column chromatography purification, obtains white solid 3.6g (yield:90.05%).
1 H-NMR(300MHz, CDCl
3 ): δ(ppm) 8.61 (m, 1H)；8.26(d，2H)，7.88(d，2H)，7.64(d，2H)，7.47(m，4H)，7.33(t，2H)。
Embodiment 10:
4,4 '-bis-(4 ', 4 ', 5 ', 5 '-tetramethyl--1 ', 3 ', 2 '-dioxaborinate-2 ') and the preparation of triphenylamine (M2)
Compound 8 and THF is added in 250 mL flasks, Jiang Wen Zhi – 78 DEG C, dropwise add n-butyllithium, stir 1 hour at mixture – 78 DEG C, then in reaction solution, squeeze into 2-isopropoxy-4 with syringe fast, 4,5,5-tetramethyl--1,3,2-dioxaborolanes, reaction stirring is spent the night.Then reaction solution is poured into water, and uses CH
2 cl
2 extract four times, then use dried over mgso, removal of solvent under reduced pressure, finally obtain white crystal (Yield:79%) with silica gel/sherwood oil column chromatography.
1 h-NMR (300MHz, CDCl
3 ): δ (ppm) 8.61 (m, 1H), 7.75 (d, 4H), 7.46 (d, 2H), 7.14 (d, 2H), 7.10 (d, 4H), 1.36 (s, 24H ,-CH
3 ).
Synthetic route 3 is as follows:
Embodiment 11:
The preparation of polymkeric substance (PCTN)
In reaction flask, add compound M2(248.5mg, 0.5mmol), compound M1(325.0mg, 0.5mmol) and Pd (PPh
3 )
4 (3mg), then under argon shield, add 8ml toluene with syringe in reaction flask, 2ml removes dried up and 2ml TBAH (35%) aqueous solution, and at 90 DEG C, lucifuge reacts 48 hours.Stopped reaction, instills reaction solution in methyl alcohol, filters, obtains fibrous solids.Then fibrous solids is used acetone extraction 24h, then change THF extracting 24h, the THF solution that concentrated extracting obtains, then instill in methyl alcohol, filter, dry, obtain polymkeric substance, productive rate about 50%.
1 H-NMR(300MHz, CDCl
3 ): δ(ppm)8.12(t,2H); 7.60(m,8H); 7.20(m,9H); 4.66(br,1H); 2.75(m,8H); 2.56(br,4H); 1.3~2.2(m,20H); 1.13(t,12H)。
Embodiment 12:
Containing the preparation of the organic semiconductor material (PCTN-Br) of quaternary ammonium salt group
By polymer PC TN(50mg in 100mL round-bottomed flask) be dissolved in THF(25mL) in, then add monobromethane (1g, 9mmol) and DMSO(5mL), reaction solution stirs 5 days at 50 DEG C.Stopped reaction, by the THF in reaction solution and unnecessary monobromethane decompression removing, then add ethyl acetate (40mL), centrifugal, filter, filter residue is washed with chloroform and THF successively, and then at 80 DEG C, vacuum-drying one is late, namely obtains product (36mg, 57%).
1 H-NMR(300MHz, DMSO-d
6 )8.70(d,2H); 7.85(br,2H); 7.6(br,8H); 7.15(br,7H); 4.90(br,41H); 3.15(br,12H); 2.95(br,4H); 2.23(br,4H); 1.90(br,4H); 1.2~1.5(br,12H); 1.10(br,18H)。
Embodiment 13:
The preparation of OLED
Consult Fig. 1, using the organic semiconductor material PCTN-Br containing quaternary ammonium salt group prepared by embodiment 12 as hole injection layer (HIL) 3 material of OLED, prepare the OLED of following structure: ITO/HIL/P-PPV/CsF/Al.Preparation process is as follows: be first dissolved in methyl alcohol by the organic semiconductor material PCTN-Br containing quaternary ammonium salt group prepared in above-described embodiment and (can add a small amount of acetic acid when needing), make polyelectrolyte methanol solution.Time prepared by device, first in glass substrate 5, indium oxide layer tin (ITO) is sputtered as anode 4, glass substrate 5 toluene of ito anode 4 will be provided with, acetone, ethanol, deionized water is cleaned repeatedly, then UV ozone radiation treatment is carried out to glass substrate 5, then on ito anode 4, spin coating one deck is about the thick polyelectrolyte methanol solution of 40nm as hole injection layer (HIL) 3, then on hole injection layer 3, spin coating one deck is about the phenyl replacement p-phenylene vinylene (P-PPV of 80nm, be purchased from Guangzhou Li Jian photoelectric material Science and Technology Ltd.) as luminescent layer 2, next, on luminescent layer 2, vacuum evaporation a layer thickness is successively about the CsF of 1.5nm and a layer thickness is about the metal A l of 120nm as negative electrode 1, power supply 6 connects negative electrode 1 and anode 4, obtain OLED.
Adopt by display the present invention organic semiconductor material PCTN-Br containing quaternary ammonium salt group as the effect of hole injection layer material, prepared control device ITO/P-PPV/CsF/Al simultaneously.The preparation method of control device adopts the preparation method of above-mentioned OLED, and difference is only that control device does not arrange hole injection layer (HIL) 3.The measuring result of OLED lists in table 1.
Table 1:
From table 1 and Fig. 2, during using the organic semiconductor material PCTN-Br containing quaternary ammonium salt group as hole injection layer (HIL) material of OLED, the maximum current efficiency (LE of prepared OLED
max ) be 8.28cdA-1, corresponding current density is 5.42mAcm
-2 , voltage is 6.2V, and the maximum current efficiency (LE of contrast OLED without hole injection layer (HIL)
max ) be only 0.12cdA
-1 , the visible organic semiconductor material PCTN-Br containing quaternary ammonium salt group has good hole injection efficiency, can as the hole injection layer material of OLED, for the selecting of hole injection layer material of OLED provides more more options.
Above-listed detailed description is illustrating for one of the present invention possible embodiments, and this embodiment is also not used to limit the scope of the claims of the present invention, and the equivalence that all the present invention of disengaging do is implemented or changed, and all should be contained in the scope of the claims of this case.
Claims (3)
1., containing an organic semiconductor material for quaternary ammonium salt group, it is characterized in that structural formula is:
Wherein, 0<x<1,0<y<1, x+y=1; N is the polymerization degree of described organic semiconductor material, and n is the natural number of 1 ~ 10000; R
1, R
2, R
3, R
4, R
5, R
6for the alkyl of C1 ~ C4.
2., according to claim 1 containing the organic semiconductor material of quaternary ammonium salt group, it is characterized in that, described R
1, R
2, R
3, R
4, R
5, R
6for ethyl.
3. described in claim 1 or 2, contain the application of organic semiconductor material in the hole injection layer of OLED of quaternary ammonium salt group.
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|---|---|---|---|---|
| CN1974709A (en) * | 2006-06-30 | 2007-06-06 | 华南理工大学 | Electroluminescent conjugated polymer containing polar radical and its application |
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