CN108767133B - Optical pump organic light emitting diode with high gain and manufacturing method thereof - Google Patents
Optical pump organic light emitting diode with high gain and manufacturing method thereof Download PDFInfo
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Abstract
The invention discloses an optical pump organic light-emitting diode with high gain and a manufacturing method thereof. The invention uses the transparent conductive electrode of the glass substrate as the first electrode, uses the method of vacuum evaporation or solution spin coating to grow the metal oxide layer, the organic light-emitting gain medium layer, the metal oxide layer buffer layer and the metal electrode in turn, and obtains the light pump organic light-emitting diode with high gain and low spontaneous emission amplification threshold value by regulating the film thickness of the metal oxide layer and the metal electrode. The manufacturing method is simple and rapid, can realize organic laser emission by introducing the grating structure into the gain medium layer, and can be applied to realize the electric pump organic laser diode.
Description
Technical Field
The invention belongs to the technical field of laser, and particularly relates to an optical pump organic light emitting diode with high gain and a manufacturing method thereof.
Background
Since the advent of organic lasers, there has been a growing interest in organic lasers. Compared with inorganic materials, the organic laser material has wide sources, and has the advantages of wide and tunable emission spectrum, large absorption and emission sectional area and the like; and the organic material has low price and simple and convenient processing, and can adopt a simple solution method to prepare the device, even construct a flexible device on a flexible substrate, and the like. But the electric pumping organic laser device is not realized yet and is a difficult point of research.
In terms of devices, people mainly research device structures based on organic light emitting diodes (O L ED) and Organic Field Effect Transistors (OFET). particularly, organic semiconductor light emitting diodes O L ED are important ways for realizing electrically pumped organic semiconductor lasers, but the O L ED device structures are still provided with various challenges, such as the problem of carrier mobility under high electric field, the problem of interaction between excitons, quenching of excitons by metal electrodes and the like.
Disclosure of Invention
Aiming at the difficulties in the prior art, the invention aims to provide an optical pump organic light-emitting diode with high gain and a manufacturing method thereof. The light pump organic light emitting diode with high gain and low laser pumping threshold is prepared by adjusting the metal oxide functional layer and combining the spirofluorene ladder-shaped structure material with high gain.
In order to achieve the purpose, the invention adopts the technical scheme that:
an optical pump organic light emitting diode with high gain comprises a transparent conductive electrode, a metal oxide functional layer, an organic gain medium layer, a hole transmission buffer layer and a metal electrode which are sequentially arranged from top to bottom.
Preferably, the transparent conductive electrode is made of one of indium tin oxide, fluorine-doped tin oxide and aluminum-doped zinc oxide.
Preferably, the metal oxide functional layer is made of zinc oxide, is obtained by spin-coating and annealing a precursor solution of the zinc oxide, and has a thickness of 35-90 nm.
Preferably, the organic gain medium layer is made of a material based on a spirofluorene trapezoid structure, and the thickness of the organic gain medium layer is 100-200 nm.
Preferably, the material based on the spirofluorene ladder-shaped structure is a linear ladder-shaped micromolecule material constructed by taking spirofluorene as a core star-shaped ladder-shaped macromolecule or based on the spirofluorene structure.
Preferably, the hole transmission buffer layer is made of molybdenum oxide and is grown on the organic gain medium layer in a vacuum evaporation mode, and the thickness of the hole transmission buffer layer is 5-8 nm.
Preferably, the metal electrode is made of one of silver, gold, copper and aluminum, and the thickness of the metal electrode is 50-120 nm.
A manufacturing method of an optical pump organic light emitting diode comprises the following steps:
step a, selecting a material for preparing a transparent conductive electrode, ultrasonically cleaning the material with soap water, deionized water, acetone and ethanol in sequence, and drying to obtain a clean transparent conductive electrode;
step b, carrying out plasma treatment on the clean transparent conductive electrode obtained in the step a for 5-30 minutes;
step c, preparing a precursor solution of the metal oxide, and performing spin coating and annealing on the transparent conductive electrode processed in the step b in a spin coating mode to obtain a metal oxide functional layer;
step d, preparing an organic gain medium solution, and spin-coating the metal oxide functional layer processed in the step c to obtain an organic gain medium layer;
e, putting the organic gain medium layer processed in the step d into a vacuum evaporation system, sequentially evaporating a hole transmission buffer layer and a metal electrode, and controlling the thickness through a crystal oscillator;
and f, finishing the evaporation, keeping the vacuum state, and cooling the manufactured optical pump organic light emitting diode to room temperature.
In the step e, the evaporation condition is that the pressure of the evaporation cavity is controlled to be 1-10 × 10-4Pa, and the evaporation rate is controlled to be 0.1-1 nm/s.
In the step c, the thickness of the metal oxide functional layer is controlled to be 35-90 nm;
in the step d, the thickness of the organic gain medium layer is controlled to be 100-200 nm;
in the step e, the thickness of the hole transmission buffer layer is controlled to be 5-8 nm, and the thickness of the metal electrode is controlled to be 50-120 nm.
Has the advantages that: the optical pump organic light-emitting diode with high gain provided by the invention has the advantages of simple structure, easy design, simple process and low cost. Meanwhile, the method for adjusting the metal oxide functional layer and using the spirofluorene ladder-shaped structure material with high gain is simple and effective, and the optically pumped organic light-emitting diode with high gain and low laser pumping threshold can be obtained. The prepared device structure can introduce a grating structure into the gain medium layer to realize organic laser emission, and can be applied to realize an electric pump organic laser diode.
Drawings
FIG. 1 is a schematic view of an optical pump OLED structure according to the present invention.
Fig. 2 is a schematic molecular structure diagram of organic gain medium spirofluorene ladder derivative Sp L (2) -1 used in the examples.
FIG. 3 shows Sp L (2) -11H NMR chart
FIG. 4 shows Sp L (2) -113C NMR chart
FIG. 5 is MA L DI-TOF graph of Sp L (2) -1
Fig. 6 is a graph of the spectrum as a function of the pumping intensity under the optical pumping in example 1, which is a graph of the normalized spectrum as a function of the pumping intensity.
Fig. 7 is a graph of the variation of the half-width of the spectrum of the device with different zinc oxide thickness with the pumping energy under the condition of the optical pump in the embodiment 1, and the figure is a graph of the variation of the spontaneous emission amplification threshold with different zinc oxide thicknesses.
Fig. 8 is a graph of device net gain under optical pumping for example 2.
Detailed Description
The invention is further explained below with reference to the drawings.
As shown in fig. 1, the optical pump organic light emitting diode with high gain of the present invention includes a transparent conductive electrode 1, a metal oxide functional layer 2, an organic gain medium layer 3, a hole transport buffer layer 4, and a metal electrode 5, which are sequentially disposed from top to bottom.
The transparent conductive electrode is made of one of indium tin oxide, fluorine-doped tin oxide and aluminum-doped zinc oxide.
The metal oxide functional layer is made of zinc oxide, is obtained by spin-coating and annealing a precursor solution of the zinc oxide, and has a thickness of 35-90 nm.
The organic gain medium layer is made of a material based on a spirofluorene ladder-shaped structure, and the thickness of the organic gain medium layer is 100-200 nm.
The material based on the spirofluorene ladder-shaped structure is a linear ladder-shaped micromolecule material constructed by taking spirofluorene as a nuclear star-shaped ladder-shaped macromolecule or based on the spirofluorene structure.
The hole transmission buffer layer is made of molybdenum oxide and is obtained by growing on the organic gain medium layer in a vacuum evaporation mode, and the thickness of the hole transmission buffer layer is 5-8 nm.
The metal electrode is made of one of silver, gold, copper and aluminum, and the thickness of the metal electrode is 50-120 nm.
The manufacturing method of the optical pump organic light-emitting diode comprises the following steps:
step a, selecting a material for preparing a transparent conductive electrode, ultrasonically cleaning the material with soap water, deionized water, acetone and ethanol in sequence, and drying to obtain a clean transparent conductive electrode;
step b, carrying out plasma treatment on the clean transparent conductive electrode obtained in the step a for 5-30 minutes;
step c, preparing a precursor solution of the metal oxide, and performing spin coating and annealing on the transparent conductive electrode processed in the step b in a spin coating mode to obtain a metal oxide functional layer, wherein the thickness is controlled to be 35-90 nm;
step d, preparing an organic gain medium solution, and spin-coating the metal oxide functional layer processed in the step c to obtain an organic gain medium layer, wherein the thickness is controlled to be 100-200 nm;
step e, placing the organic gain medium layer processed in the step d into a vacuum evaporation system, and controlling the pressure of an evaporation cavity to be 1-10 × 10-4Pa, controlling the evaporation rate to be 0.1-1 nm/s, sequentially evaporating a hole transmission buffer layer and a metal electrode, controlling the thickness through a crystal oscillator, controlling the thickness of the hole transmission buffer layer to be 5-8 nm, and controlling the thickness of the metal electrode to be 50-120 nm;
and f, finishing the evaporation, keeping the vacuum state, and cooling the manufactured optical pump organic light emitting diode to room temperature.
The present invention is further illustrated by the following specific examples. The present invention will be better understood from the following examples. However, those skilled in the art will readily appreciate that the specific material ratios, process conditions and results thereof described in the examples are illustrative only and should not be taken as limiting the invention as detailed in the claims.
In the embodiment described below, it is preferred that,
ITO: indium tin oxide;
FTO: fluorine-doped tin oxide.
Example 1
In this example, the device structure is Indium Tin Oxide (ITO)/zinc oxide/Sp L (2) -1/molybdenum oxide/silver, wherein the thickness of zinc oxide is 35nm, the thickness of Sp L (2) -1 is 120nm, the thickness of molybdenum oxide is 5nm, and the thickness of silver is 120 nm.
The selected transparent conductive electrode is ITO, the metal electrode is silver, and the organic gain layer is a trapezoidal spirofluorene micromolecule derivative Sp L (2) -1.
The manufacturing steps are as follows:
step a, selecting ITO as a material of a transparent conductive electrode, ultrasonically cleaning the ITO with soap water, deionized water, acetone and ethanol in sequence, and drying to obtain a clean transparent conductive electrode;
step b, carrying out plasma treatment on the clean transparent conductive electrode for 10 minutes;
c, preparing a precursor solution of the metal oxide zinc oxide, and performing spin coating and annealing on the transparent conductive electrode treated in the step b in a spin coating mode to obtain a zinc oxide layer; controlling the thickness of the zinc oxide layer to be 35nm through different spin coating parameters;
step d, preparing an Sp L (2) -1 solution, and spin-coating the functional layer of the metal oxide treated in the step c to obtain Sp L (2) -1, wherein the thickness of the Sp L (2) -1 is controlled to be 120 nm;
step e, putting the sample processed in the step d into a vacuum evaporation system, and controlling the pressure of an evaporation cavity to be 1.2 × 10-4Pa, evaporation rate is controlled at 0.1nm/s, molybdenum oxide and silver are evaporated in sequence, and thickness is controlled by crystal oscillatorWherein the thickness of the molybdenum oxide is 5nm, and the thickness of the silver is 120 nm;
and f, finishing the evaporation, keeping the vacuum state, cooling the electrode to room temperature, and then performing related tests.
Fig. 3 shows the spectrum as a function of the pump intensity under an optical pump, and the figure is a graph of the normalized spectrum as a function of the pump intensity. It can be seen that there is a phenomenon of spectral narrowing under the organic diode when the intensity of the optical pump reaches a certain value.
In this embodiment, the organic gain layer is made of a trapezoidal spirofluorene small molecule derivative Sp L (2) -1, and its structural formula is:
synthesized by the following method:
the synthetic route is as follows:
dibromo spirofluorene is subjected to Suzuki coupling reaction under the solvent conditions of monoboronate, butyl lithium and tetrahydrofuran to obtain a spirofluorene diboronate monomer 1, the spirofluorene diboronate and a monomer 2 are subjected to Suzuki coupling reaction to obtain a spirofluorene two-arm trapezoidal precursor 3, the lithiation of bromobutyl benzene is realized through butyl lithium, the lithium bromobutyl benzene attacks a carbonyl active site, and finally, a cyclization process is realized through boron trifluoride diethyl ether, wherein the Synthesis references of the monomer 2 are' Yi Jian, M.Fang, S.J.Chang, J.J.Huang, S.Q.Chu, S.M.Hu, C.F. L iu, W.Y. L ai, W.Huang.Tods pharmaceutical monomeric Star-Shaped L ader-type conjugated Systems, Degan, Synthesis, Stable Blue fluorescence and amplified emission, J.5423, J.48-48. J.23.
The synthesis steps of Sp L (2) -1 are as follows:
step I, under the condition of nitrogen, adding 2, 7-dibromo spirobifluorene (1.89g,4.00mmol) and 30M L anhydrous tetrahydrofuran into a dry reaction bottle, stirring for half an hour at the temperature of minus 78 ℃, slowly dropwise adding a 4.8M L butyl lithium hexane solution (12.00mmol) to ensure that the concentration of butyl lithium is 2.5M, stirring for 1 hour, quickly dropwise adding isopropanol pinacol borate (2.96g,16.00mmol) into a reaction system, reacting for 12 hours at the temperature of minus 78 ℃, quenching reaction by ice water, extracting an organic phase by dichloromethane, washing twice and three times by deionized water, drying by anhydrous magnesium sulfate, carrying out suction filtration, carrying out vacuum concentration on a crude product, purifying by column chromatography (eluent is DCM), obtaining 1.32g of spirofluorene diboronate white solid, and ensuring the yield to be 58%.
Step II: spirofluorene diboronate (100mg,0.18mmol), precursor 1(389mg,0.54mmol), tetrabutylammonium bromide (208mg,0.65mmol), tetrakistriphenylphosphine palladium (3mg,0.003mmol), NaHCO under nitrogen conditions3(54mg,0.65mmol), tetrahydrofuran (15m L) and water (8m L) were added into a 50m L reaction flask, reacted at 85 ℃ for 48 hours, quenched with ice water, the organic phase was extracted with dichloromethane, washed with deionized water twice and three times, dried over anhydrous magnesium sulfate, filtered, concentrated under vacuum, and the crude product was purified by column chromatography (eluent is DCM: PE ═ 2:1) to give 218mg of a yellow spirofluorene double-armed ladder precursor in 76% yield.
And step III, under the condition of nitrogen, adding para-bromobutyl benzene (639mg,3.0mmol) and a dried tetrahydrofuran solution (20M L) into a 100M L reaction bottle, cooling to-78 ℃, dropwise adding 1.2M L butyl lithium hexane solution, wherein the concentration of butyl lithium is 2.5M, after reacting for 1 hour, dropwise adding 159mg (0.1mmol) of a spirofluorene two-arm trapezoidal precursor dissolved in 3M L tetrahydrofuran into the reaction bottle, slowly heating for overnight reaction, quenching with ice water, extracting an organic phase with dichloromethane, washing twice with deionized water, drying with anhydrous magnesium sulfate, carrying out suction filtration, carrying out vacuum concentration on a crude product, carrying out column chromatography (eluent is DCM: PE ═ 1:1), obtaining a yellow transparent colloid, dissolving the yellow colloid in 20M L dichloromethane solution, dropwise adding 0.2M L boron ether, reacting and stirring for 30 minutes at room temperature, quenching with ice water, extracting the organic phase with dichloromethane, carrying out vacuum concentration on the organic phase, carrying out twice washing with deionized water, drying, carrying out vacuum column chromatography, carrying out vacuum concentration on the yellow colloid, obtaining a light yellow colloid, and obtaining a light yellow compound (DCM: 139mg, and purifying).
1H NMR(400MHz,CDCl3,):7.94–7.87(m,3H),7.69(d,J＝3.0Hz,1H),7.65(s,1H),7.54(d,J＝3.4Hz,1H),7.51(d,J＝3.1Hz,1H),7.47(d,J＝10.7Hz,3H),7.44(s,1H),7.39–7.33(m,5H),7.20–7.15(m,18H),7.07(d,J＝8.3Hz,6H),6.99(d,J＝8.2Hz,18H),6.93(d,J＝7.9Hz,16H),2.58(s,8H),2.50(s,8H),1.60(s,8H),1.52(d,J＝5.8Hz,8H),1.38–1.30(m,16H),0.95–0.89(m,24H).13C NMR(100MHz,CDCl3,):153.64,153.52,152.83,152.30,152.15,151.58,148.66,147.82,147.65,147.04,143.48,143.11,143.00,141.08,141.02,140.89,140.85,140.72,136.23,135.03,134.95,133.16,129.05,128.43,128.38,128.21,128.15,128.06,127.71,126.92,126.60,123.88,123.72,122.52,122.42,119.94,65.46,64.50,58.13,35.25,35.16,33.48,33.40,33.58,22.45,13.99,13.96.MALDI-TOF-MS(m/z):calcd for C157H146N2,exact mass:M+2059.15；Found:2058.987(M+).
Comparative example 1
In this comparative example, the device structure was Indium Tin Oxide (ITO)/zinc oxide/Sp L (2) -1/molybdenum oxide/silver, where the thickness of zinc oxide was 90nm, the thickness of Sp L (2) -1 was 120nm, the thickness of molybdenum oxide was 5nm, and the thickness of silver was 120 nm.
In this comparative example, which is characterized by a zinc oxide thickness of 90nm, see fig. 4 showing the variation of the spectral half-width with pumping energy for devices of different zinc oxide thicknesses in the case of an optical pump, the figure is a graph of the spontaneous emission amplification threshold with different zinc oxide thicknesses. It can be seen that with the introduction of zinc oxide and the increase of the thickness of the zinc oxide, the spontaneous emission amplification threshold of the device is greatly reduced, and the spontaneous emission amplification threshold of the device is lower when the thickness of the zinc oxide is 90nm compared with that of the device with the thickness of the zinc oxide of 35 nm. It can be seen that metal oxides play a very important positive role in reducing optical losses.
Example 2
This embodiment is substantially the same as embodiment 1, and is characterized in that the material of the transparent conductive electrode is fluorine-doped tin oxide.
In this example, the device structure was fluorine-doped tin oxide (FTO)/zinc oxide/Sp L (2) -1/molybdenum oxide/silver, wherein the thickness of zinc oxide was 90nm, the thickness of Sp L (2) -1 was 120nm, the thickness of molybdenum oxide was 5nm, and the thickness of silver was 120 nm.
Example 3
This embodiment is substantially the same as embodiment 1, and is characterized in that the metal electrode is made of aluminum and has a thickness of 80 nm.
In this example, the device structure was Indium Tin Oxide (ITO)/zinc oxide (90nm)/Sp L (2) -1(120 nm)/molybdenum oxide (5 nm)/aluminum (80nm), where the thickness of zinc oxide was 90nm, the thickness of Sp L (2) -1 was 120nm, the thickness of molybdenum oxide was 5nm, and the thickness of aluminum was 80 nm.
Fig. 5 shows the net gain plot of the device under the optical pump of example 2. It can be seen that the use of the trapezoidal spirofluorene structural material still has a high net gain coefficient even under the structure of the organic light emitting diode.
From the above, the invention provides an optically pumped organic light emitting diode with high gain and low laser threshold by using a simple method.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (7)
1. An optically pumped organic light emitting diode with high gain, characterized by: the organic gain medium layer comprises a transparent conductive electrode (1), a metal oxide functional layer (2), an organic gain medium layer (3), a hole transmission buffer layer (4) and a metal electrode (5) which are sequentially arranged from top to bottom; the metal oxide functional layer (2) is made of zinc oxide and is obtained by spin-coating and annealing a precursor solution of the zinc oxide; the organic gain medium layer (3) is made of a material based on a spirofluorene ladder-shaped structure, and the material is a linear ladder-shaped micromolecule material constructed by taking spirofluorene as a nuclear star-shaped ladder-shaped macromolecule or based on the spirofluorene structure.
2. An optically pumped organic light emitting diode with high gain according to claim 1, wherein: the transparent conductive electrode (1) is made of one of indium tin oxide, fluorine-doped tin oxide and aluminum-doped zinc oxide.
3. An optically pumped organic light emitting diode with high gain according to claim 1, wherein: the hole transmission buffer layer (4) is made of molybdenum oxide and is obtained by growing on the organic gain medium layer (3) in a vacuum evaporation mode.
4. An optically pumped organic light emitting diode with high gain according to claim 1, wherein: the metal electrode (5) is made of one of silver, gold, copper and aluminum.
5. A method of fabricating an optically pumped organic light emitting diode as claimed in any of claims 1 to 4, characterized by: the method comprises the following steps:
step a, selecting a material for preparing a transparent conductive electrode, ultrasonically cleaning the material with soap water, deionized water, acetone and ethanol in sequence, and drying to obtain a clean transparent conductive electrode;
step b, carrying out plasma treatment on the clean transparent conductive electrode obtained in the step a for 5-30 minutes;
step c, preparing a precursor solution of the metal oxide, and performing spin coating and annealing on the transparent conductive electrode processed in the step b in a spin coating mode to obtain a metal oxide functional layer;
step d, preparing an organic gain medium solution, and spin-coating the metal oxide functional layer processed in the step c to obtain an organic gain medium layer;
e, putting the organic gain medium layer processed in the step d into a vacuum evaporation system, sequentially evaporating a hole transmission buffer layer and a metal electrode, and controlling the thickness through a crystal oscillator;
and f, finishing the evaporation, keeping the vacuum state, and cooling the manufactured optical pump organic light emitting diode to room temperature.
6. Method for manufacturing an optically pumped organic light emitting diode according to claim 5The method is characterized in that in the step e, the evaporation condition is that the pressure of the evaporation cavity is controlled to be 1-10 × 10−4Pa, and the evaporation rate is controlled to be 0.1-1 nm/s.
7. The method of claim 5, wherein:
in the step c, the thickness of the metal oxide functional layer is controlled to be 35-90 nm;
in the step d, the thickness of the organic gain medium layer is controlled to be 100-200 nm;
in the step e, the thickness of the hole transmission buffer layer is controlled to be 5-8 nm, and the thickness of the metal electrode is controlled to be 50-120 nm.
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