CN110718642B - OLED device based on blended light emitting layer and preparation method thereof - Google Patents

OLED device based on blended light emitting layer and preparation method thereof Download PDF

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CN110718642B
CN110718642B CN201810755140.8A CN201810755140A CN110718642B CN 110718642 B CN110718642 B CN 110718642B CN 201810755140 A CN201810755140 A CN 201810755140A CN 110718642 B CN110718642 B CN 110718642B
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应磊
彭沣
钟知鸣
黄飞
曹镛
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Dongguan Volt Ampere Photoelectric Technology Co ltd
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses an OLED device based on a hole-transport small molecule and a blended light-emitting layer containing triphenylamine ethylene unit light-emitting polymers and a preparation method thereof. The OLED device structurally comprises an anode, a cathode and at least one organic compound layer arranged between the two electrodes; the organic compound layer comprises at least one blended light-emitting layer; the components of the blended light-emitting layer comprise hole-transport small molecules and a light-emitting polymer containing triphenylamine ethylene units. The invention firstly provides a high-performance luminescent polymer of triphenylamine ethylene units, which has high thermal stability and good film-forming property and can be used for preparing organic luminescent devices; then, a hole transport small molecule is provided, and the hole transport small molecule is used as a light emitting layer after being blended with the light emitting polymer, so that the advantages of high efficiency and long service life are achieved. The OLED device prepared by the method has good application effect and also has great advantages in the aspect of industrialization.

Description

OLED device based on blended light emitting layer and preparation method thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an OLED device based on a hole-transport small molecule and a blended light-emitting layer containing triphenylamine ethylene unit light-emitting polymers and a preparation method thereof.
Background
An Organic Light-Emitting Diode (OLED) refers to an Organic material capable of Emitting Light under the action of current, that is, capable of directly converting electric energy into Light energy. At present, many Organic Light Emitting Devices (OLEDs) can be used for illumination and can be manufactured into display screens and electronic paper, have the characteristics of gorgeous property, high brightness, ultrathin property, high reaction speed and the like, start to gradually enter the market, and are the most advantageous technology of next-generation flat panel displays.
The core part of an OLED is the light-emitting layer, and the material used in the light-emitting layer determines the light-emitting efficiency of the device. From the beginning, small-molecule fluorescent dye compounds, high-molecular compounds, and metal complexes have been used as the over-luminescent layer. The key points of the method are that the method has the properties of high luminous quantum efficiency, good film forming performance, good carrier transport performance and the like. Nowadays, polymers are being studied more as luminescent materials. The difficulties of the polymer luminescent material are as follows: the polymer material is a single-layer structure device, and balanced injection of electrons and holes is satisfied by using a single material. It is difficult to satisfy high luminous efficiency, good film forming property and high heat resistance at the same time, so in order to manufacture high-performance OLED luminescent devices, doping or blending of luminescent materials or addition of a layer of hole transport material is needed.
At present, organic light emitting devices are increasingly used in life, but there still exist problems to be solved: long service life and high efficiency. Therefore, it is urgent to develop materials having better performance.
Disclosure of Invention
In order to overcome the defects and shortcomings of the prior art, the invention mainly aims to provide an OLED device based on a blended light-emitting layer of a hole transport small molecule and a light-emitting polymer containing triphenylamine ethylene units.
The invention blends the hole-transport micromolecules and the luminescent polymer containing the triphenylamine ethylene unit to be used as the luminescent layer, wherein the luminescent polymer based on the triphenylamine ethylene unit as the core is chromophore, thereby obtaining the OLED device.
The invention also aims to provide a preparation method of the OLED device based on the blended light-emitting layer of the hole-transport small molecules and the triphenylamine ethylene unit-containing light-emitting polymer.
The purpose of the invention is realized by the following scheme:
an OLED device based on a blended light-emitting layer of hole-transport small molecules and a light-emitting polymer containing triphenylamine ethylene units structurally comprises an anode, a cathode and at least one organic compound layer arranged between the two electrodes; the organic compound layer comprises at least one blended light-emitting layer; the components of the blended light-emitting layer comprise hole-transport small molecules and a light-emitting polymer containing triphenylamine ethylene units.
The chemical structural formula of the luminescent polymer containing the triphenylamine ethylene unit satisfies one of the following general formulas:
Figure BDA0001726549560000021
in the formula: x and y are mole fractions of each unit component, and satisfy the following conditions: 0< x <1, 0< y <1, x + y ═ 1; n is the number of repeating units, and n is an integer in the range of 5-5000;
Ar 1 is an aromatic hydrocarbon group of C6-60 or an aromatic heterocyclic group of C3-60;
Ar 2 is a vinyl triarylamine unit having the following general structure:
Figure BDA0001726549560000022
Ar 3 、Ar 4 、Ar 5 、Ar 6 the same or different are each a C6-60 aromatic hydrocarbon group or a C3-60 aromatic heterocyclic group.
Further, Ar 1 Preferably at least one of the following chemical structures or derivatives of the following structures:
Figure BDA0001726549560000023
Figure BDA0001726549560000031
wherein R is 1 Is C1-30 alkyl, C3-30 cycloalkyl, C6-60 aromatic hydrocarbon or C3-60 aromatic heterocyclic radical; r is 2 、R 3 、R 4 H, D, F, CN, alkenyl, alkynyl, amino, nitro, acyl, alkoxy, carbonyl, sulfonyl, C1-30 alkyl, C1-30 alkoxy, C3-30 cycloalkyl, C6-60 aromatic hydrocarbon or C3-60 aromatic heterocyclic group.
Further, Ar is 3 、Ar 4 、Ar 5 、Ar 6 The same or different is preferably one of the following structures or derivatives thereof, respectively:
Figure BDA0001726549560000041
wherein R is 5 Is C1-30 alkyl, C3-30 cycloalkyl, C6-60 aromatic hydrocarbon or C3-60 aromatic heterocyclic radical.
Further, said Ar 2 Preferably at least one of the following chemical structures or derivatives of the following structures:
Figure BDA0001726549560000042
Figure BDA0001726549560000051
wherein R is 6 H, D, F, CN, alkenyl, alkynyl, amino, nitro, acyl, alkoxy, carbonyl, sulfonyl, C1 ~ 30 alkyl, C1 ~ 30 alkoxy, C3 ~ 30 cycloalkyl, C6 ~ 60 aromatic hydrocarbon or C3 ~ 60 aromatic heterocyclic.
In the device, the hole transport micromolecules comprise carbazoles and triarylamine derivatives; preferably at least one of the structures shown below:
Figure BDA0001726549560000052
Figure BDA0001726549560000061
Figure BDA0001726549560000071
Figure BDA0001726549560000081
Figure BDA0001726549560000091
Figure BDA0001726549560000101
Figure BDA0001726549560000111
Figure BDA0001726549560000121
Figure BDA0001726549560000131
Figure BDA0001726549560000141
Figure BDA0001726549560000151
Figure BDA0001726549560000161
Figure BDA0001726549560000171
Figure BDA0001726549560000181
Figure BDA0001726549560000191
in the blended light-emitting layer, the content of the hole-transporting micromolecules is more than 0 and less than or equal to 50 percent by mass. The content of the luminescent polymer containing triphenylamine ethylene units is more than or equal to 50% and less than 100% by mass.
The thickness of the blended light-emitting layer is preferably 50-1000 nm.
The invention also provides a preparation method of the OLED device based on the hole transport micromolecule and the blended light-emitting layer containing the triphenylamine ethylene unit light-emitting polymer, which comprises the following steps:
(1) attaching a hole injection layer, preferably a mixture of polystyrene sulfonic acid and poly (3, 4-ethylenedioxythiophene), an aromatic amine compound to the ITO substantially by a spin coating method;
(2) optionally, a layer of solvent-orthogonal processing or crosslinkable or curable hole transport layer is prepared on the hole injection layer by a spin coating method, preferably polyvinylcarbazole, crosslinkable aromatic amine-containing compounds or carbazole-based compounds;
(3) preparing at least one layer of light-emitting layer blended by the hole-transport micromolecules and the triphenylamine-containing ethylene unit light-emitting polymers in a spin coating mode, and dissolving the hole-transport micromolecules and the triphenylamine-containing ethylene unit light-emitting polymers in an organic solvent before spin coating;
(4) optionally, an electron injection layer and/or a cathode reflection electrode layer is/are prepared on the light emitting layer by spin coating or evaporation;
(5) finally, a layer of cathode electrode is evaporated.
The OLED device based on the blended light-emitting layer of the hole-transport micromolecule and the triphenylamine ethylene unit light-emitting polymer can further comprise a transparent substrate layer, an ITO anode layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer and a cathode reflection electrode layer. The transparent substrate layer, the ITO anode layer, the hole injection layer, the hole transport layer, the light-emitting layer, the electron injection layer and the cathode reflection electrode layer are sequentially stacked and arranged.
Compared with the prior art, the invention has the following advantages and beneficial effects:
the invention firstly provides a high-performance luminescent polymer of triphenylamine ethylene units, which has high thermal stability and good film-forming property and can be used for preparing organic luminescent devices; then, a hole transport small molecule is provided, and the hole transport small molecule is used as a light emitting layer after being blended with the light emitting polymer, so that the advantages of high efficiency and long service life are achieved. The OLED device prepared by the method has good application effect and also has great advantages in the aspect of industrialization.
Drawings
FIG. 1 shows the device 1 at 1000cd/m 2 The electroluminescence spectrum at brightness is blue emission.
Fig. 2 is a current efficiency-current density curve for device 5.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
The materials referred to in the following examples are commercially available.
Example 1
Preparation of electroluminescent device 1 (comparative example)
The device takes polymer 1 based on triphenylamine ethylene unit as a luminescent layer, and the preparation steps comprise:
a) ultrasonically cleaning an ITO glass substrate with isopropanol, acetone, deionized water (4 times) and isopropanol for 15 minutes respectively, and then treating the ITO glass substrate with plasma for 2 minutes;
b) on the ITO anode, a hole injection layer material (poly (3, 4-ethylenedioxythiophene) doped with polystyrene sulfonic acid) is obtained by a spin coating method: PSS) is formed on the surface of the substrate, the thickness of the film is about 40nm, and the layer is a hole injection layer;
c) on the hole injection layer, obtaining a film of a hole transport layer material PVK by a spin coating method, wherein the film thickness is about 20nm, and the layer is the hole transport layer;
d) on the hole transport layer, a thin film of a light-emitting layer material polymer P1 (dissolved in xylene) is obtained by a spin coating method, the thickness of the thin film is about 60nm, and the layer is a light-emitting layer;
e) vacuum evaporating an electron injection layer CsF on the luminescent layer, wherein the thickness of the electron injection layer CsF is 0.8nm, and the electron injection layer is the electron injection layer;
f) vacuum evaporating cathode Al (100nm) on the electron injection layer, wherein the cathode is a cathode reflecting electrode layer;
the molecular formulas of PVK and luminescent polymer P1 described in this example are as follows:
Figure BDA0001726549560000211
example 2
Preparation of electroluminescent devices 2-5
The device fabrication method is similar to device 1, except that: in the step d, the polymer luminescent material P1 and the hole transport small molecule BCFN are blended and dissolved in xylene, and then a blended luminescent layer is obtained by a spin coating method. In the blended light-emitting layers corresponding to the devices 2-5, the mass fraction concentrations of BCFN are 4 wt%, 8 wt%, 12 wt% and 16 wt%, respectively.
The structural formula of the hole transport small molecule BCFN described in the embodiment is as follows:
Figure BDA0001726549560000221
example 3
Preparation of electroluminescent devices 6-9
The device fabrication method is similar to device 1, except that: in the step d, the polymer luminescent material P1 and the hole transport small molecule BSFN are blended and dissolved in xylene, and then a blended luminescent layer is obtained by a spin coating method. In the blended light-emitting layers corresponding to the devices 6-9, the mass fraction concentrations of BSFN are respectively 4 wt%, 8 wt%, 12 wt% and 16 wt%.
The structural formula of the hole transport small molecule BSFN described in this example is as follows:
Figure BDA0001726549560000222
example 4
Preparation of electroluminescent devices 10-13
The device fabrication method is similar to device 1, except that: in the step d, the polymer luminescent material P2 and the hole transport small molecule NPB are blended and dissolved in xylene, and then a blended luminescent layer is obtained by a spin coating method. In the blended light-emitting layers corresponding to the devices 10 to 13, the mass fraction concentrations of NPB are respectively 4 wt%, 8 wt%, 12 wt% and 16 wt%.
The molecular formulas of NPB and luminescent polymer P2 described in this example are as follows:
Figure BDA0001726549560000231
example 5
Preparation of electroluminescent devices 14-17
The device fabrication method is similar to device 1, except that: step c, i.e. no hole transport material, is not required. In the step d, the polymer luminescent material P2 and the hole transport small molecule TAPC are blended and dissolved in xylene, and then a blended luminescent layer is obtained by a spin coating method. The mass fraction concentrations of TAPC in the blended emissive layers corresponding to devices 14-17 were 4 wt%, 8 wt%, 12 wt%, 16 wt%, respectively.
The structural formula of the hole transport small molecule TAPC described in this example is as follows:
Figure BDA0001726549560000232
example 6
Electroluminescent device 18
The device fabrication method is similar to device 1, except that: in step d, the polymer luminescent material P1 is blended with the hole transport small molecules BCFN and BSFN and dissolved in xylene, and then a blended luminescent layer is obtained through a spin coating method. The concentrations of BCFN, BSFN in the blended emissive layer of device 18 were 4 wt%, respectively.
Example 7
Preparation of electroluminescent devices 19-22
The device fabrication method is similar to device 1, except that: in the step c, PVK, BCFN, BSFN, NPB and TAPC are respectively blended and dissolved in chlorobenzene, and a blended hole transport layer is obtained by a spin coating method, wherein the mass fractions of the BCFN, BSFN, NPB and TAPC fill the hole transport layer are all 10%; in the step d, the polymer luminescent material P1 and hole transport small molecule BCFN (mass fraction is 10%) are blended and dissolved in xylene, and then a blended luminescent layer is obtained by a spin coating method.
The results of the characteristic tests of the light emitting device fabricated in the above embodiment are shown in table 1, fig. 1 and fig. 2.
FIG. 1 shows the device 1 at 1000cd/m 2 The electroluminescence spectrum at brightness is blue emission. Fig. 2 is a plot of current efficiency versus current density for device 5, which exhibits superior device performance and stability.
Table 1 test of light emitting characteristics of light emitting device
Figure BDA0001726549560000241
Figure BDA0001726549560000251
The results show that the light-emitting polymer containing triphenylamine ethylene units and the hole transport micromolecules are applied to the light-emitting layer of the organic light-emitting device after being blended, have the advantages of low driving voltage, high light-emitting efficiency and high maximum brightness, and are organic light-emitting materials with excellent performance. Compared with the device 1 without the mixed hole transport micromolecules, the devices 2-22 based on the mixed hole transport micromolecules and the luminescent polymer have higher device performance.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such modifications are intended to be included in the scope of the present invention.

Claims (5)

1. An OLED device based on a hole-transport small molecule and a blended light-emitting layer containing triphenylamine ethylene unit light-emitting polymers is characterized in that the structure of the OLED device comprises an anode, a cathode and at least one organic compound layer arranged between the two electrodes; the organic compound layer includes at least one blended light-emitting layer; the components of the blended light-emitting layer comprise hole-transport small molecules and a light-emitting polymer containing triphenylamine ethylene units;
the chemical structural formula of the luminescent polymer containing the triphenylamine ethylene unit satisfies one of the following general formulas:
Figure FDA0003656920690000011
in the formula: x and y are mole fractions of each unit component, and satisfy the following conditions: 0< x <1, 0< y <1, x + y ═ 1; n is the number of repeating units, and n is an integer in the range of 5-5000;
Ar 1 is an aromatic hydrocarbon group of C6 to 60 or an aromatic heterocyclic group of C3 to 60;
Ar 2 is a vinyl triarylamine unit having the following general structure:
Figure FDA0003656920690000012
Ar 3 、Ar 4 、Ar 5 、Ar 6 the same or different aromatic hydrocarbon groups are C6-60 or C3-60 aromatic heterocyclic groups;
the hole transmission micromolecule comprises at least one of carbazole derivatives and triarylamine derivatives;
wherein Ar is 1 Is at least one of the following chemical structures or derivatives of the following structures:
Figure FDA0003656920690000013
Figure FDA0003656920690000021
wherein R is 1 Is C1-30 alkyl, C3-30 cycloalkyl, C6-60 aromatic hydrocarbon or C3-60 aromatic heterocyclic radical; r is 2 、R 3 、R 4 H, D, F, CN, alkenyl, alkynyl, amido, nitryl, acyl, alkoxy, carbonyl, sulfuryl, C1-30 alkyl, C1-30 alkoxy, C3-30 cycloalkyl, C6-60 aromatic hydrocarbon or C3-60 aromatic heterocyclic radical;
wherein, Ar is 3 、Ar 4 、Ar 5 、Ar 6 The same or different is respectively one of the following structures or derivatives of the following structures:
Figure FDA0003656920690000022
Figure FDA0003656920690000031
wherein R is 5 Is C1-30 alkyl, C3-30 cycloalkyl, C6-60 aromatic hydrocarbon or C3-60 aromatic heterocyclic radical;
wherein, Ar is 2 Is at least one of the following chemical structures or derivatives of the following structures:
Figure FDA0003656920690000032
Figure FDA0003656920690000041
wherein R is 6 H, D, F, CN, alkenyl, alkynyl, amino, nitro, acyl, alkoxy, carbonyl, sulfonyl, C1 ~ 30 alkyl, C1 ~ 30 alkoxy, C3 ~ 30 cycloalkyl, C6 ~ 60 aromatic hydrocarbon or C3 ~ 60 aromatic heterocyclic.
2. The OLED device based on the blended light-emitting layer of the hole-transporting small molecule and the triphenylamine ethylene unit-containing light-emitting polymer in the claim 1, is characterized in that: the hole-transporting small molecule is at least one of the following structures:
Figure FDA0003656920690000042
Figure FDA0003656920690000051
Figure FDA0003656920690000061
Figure FDA0003656920690000071
Figure FDA0003656920690000081
Figure FDA0003656920690000091
Figure FDA0003656920690000101
Figure FDA0003656920690000111
Figure FDA0003656920690000121
Figure FDA0003656920690000131
Figure FDA0003656920690000141
Figure FDA0003656920690000151
Figure FDA0003656920690000161
Figure FDA0003656920690000171
Figure FDA0003656920690000181
3. the OLED device based on the blended light-emitting layer of the hole-transporting small molecule and the triphenylamine ethylene unit-containing light-emitting polymer in the claim 1, is characterized in that: in the blended luminescent layer, the content of the hole-transport small molecules is more than 0 and less than or equal to 50 percent in percentage by mass; the content of the luminescent polymer containing triphenylamine ethylene units is more than or equal to 50% and less than 100% by mass; the thickness of the blended light-emitting layer is 50-1000 nm.
4. The OLED device based on the blended light-emitting layer of the hole-transporting small molecule and the light-emitting polymer containing the triphenylamine ethylene unit in the claim 1, wherein: the structure also comprises a transparent substrate layer, an ITO anode layer, a hole injection layer, a hole transmission layer, a luminescent layer, an electron injection layer and a cathode reflecting electrode layer; the transparent substrate layer, the ITO anode layer, the hole injection layer, the hole transport layer, the light-emitting layer, the electron injection layer and the cathode reflection electrode layer are sequentially stacked.
5. A preparation method of the OLED device based on the blended light-emitting layer of the hole-transport small molecule and the light-emitting polymer containing the triphenylamine ethylene unit as claimed in any one of claims 1 to 4 is characterized by comprising the following steps:
(1) attaching a hole injection layer on the ITO glass substrate by a spin coating method;
(2) preparing at least one layer of light-emitting layer blended by the hole-transport micromolecules and the triphenylamine-containing ethylene unit light-emitting polymers in a spin coating mode, and dissolving the hole-transport micromolecules and the triphenylamine-containing ethylene unit light-emitting polymers in an organic solvent before spin coating;
(3) finally, a layer of cathode electrode is evaporated.
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