CN112661708A - Single-layer doped electron transport layer green phosphorescent device and preparation method and application thereof - Google Patents
Single-layer doped electron transport layer green phosphorescent device and preparation method and application thereof Download PDFInfo
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- 229910052741 iridium Inorganic materials 0.000 claims description 7
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- 230000000903 blocking effect Effects 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical group [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
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- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 abstract description 2
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- -1 naphthyl anthryl modified triazine Chemical class 0.000 abstract description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
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Abstract
The invention relates to the field of organic small molecule light emitting diodes, and discloses a single-layer doped electron transport layer green phosphorescent device and a preparation method and application thereof. The high-efficiency green phosphorescence device provided by the invention introduces the naphthyl anthryl modified triazine-based organic micromolecule electron transport material. The anthracene unit and 9, 10-substituted naphthyl and anthracene group have steric hindrance, which can promote amorphous state formation and block triplet energy transfer between the light emitting layer and the electron transport layer. The 1,3, 5-triazine unit with strong electron absorption property is beneficial to improving the electron injection and transmission performance.
Description
Technical Field
The invention relates to the field of organic small molecule light-emitting diodes, in particular to a high-efficiency single-layer doped electron transport layer green phosphorescence device and a preparation method and application thereof.
Background
Organic Light Emitting Diodes (OLEDs) have advantages of self-emission, high contrast, realization of flexible display, and the like, and have important applications in the fields of flat panel display, solid state lighting, and the like. The OLED device with the single-layer electron transmission layer and high efficiency and high stability is designed, and has important significance for simplifying device preparation. Generally, since the green phosphorescent material has a high triplet energy level, an exciton-blocking/electron-transporting layer having a higher triplet energy level than the green phosphorescent material is interposed between the electron-transporting layer and the light-emitting layer. The anthracene unit is easy to synthesize and modify, and appropriate aromatic groups are respectively introduced into the 9 and 10-positions, so that an amorphous state is easy to form. However, the anthracene-based derivative has a low triplet level, less than 1.8eV, lower than the triplet level of the green phosphorescent material, and easily quenches the light emitting layer. Thus, designing and fabricating high efficiency green phosphorescent devices containing a single anthracene-based electron transport layer is challenging.
Disclosure of Invention
In view of the shortcomings of the prior art, it is a primary object of the present invention to provide a single doped electron transport layer green phosphorescent device. The green phosphorescent device is divided into a bottom emission structure and a top emission structure.
The invention also aims to provide a preparation method of the single-layer doped electron transport layer green phosphorescent device.
The invention further aims to provide the application of the single-layer doped electron transport layer green phosphorescent device in the fields of flat panel display, solid state lighting and the like.
The purpose of the invention is realized by the following technical scheme:
a single layer doped electron transport layer green phosphorescent device comprising an organic electron transport material of the structure:
the single-layer doped electron transport layer green phosphorescent device is of a bottom emission or top emission structure;
wherein the bottom-emitting green phosphorescent device structure is as follows: ITO/HIL, p-dock/HTL/EBL/HOST, green light phosphorescent iridium complex/ETM, Liq/EIL/Al;
the top emission green light phosphorescence device has the following structure: Ag/ITO/HIL, p-dock/HTL/EB/HOST, green light phosphorescent iridium complex/ETM, Liq/EIL/Mg, Ag/CPL.
P-dock is used as a hole injection layer, HTL is used as a high-mobility aromatic amine hole transport layer, and EBL is used as a hole transport/exciton blocking layer; HOST as a green phosphorescent HOST material; CPL is used as a light extraction layer; liq is an 8-hydroxyquinoline lithium complex; EIL is an electron injection layer, ETM is one of naphthyl anthryl substituted triazine derivatives shown in formulas I-II.
The EIL is one of active metals such as Yb and Liq and ionic salts thereof.
The hole injection layer, the hole transport/exciton blocking layer, and the light-emitting layer may be formed by solution processing or vacuum evaporation. The electron transport layer, the electron injection layer, the cathode, and the light extraction layer are formed by vacuum deposition.
The principle of the invention is as follows:
the high-efficiency green phosphorescence device provided by the invention introduces the naphthyl anthryl modified triazine-based organic micromolecule electron transport material. The anthracene unit and 9, 10-substituted naphthyl and anthracene group have steric hindrance, which can promote amorphous state formation and block triplet energy transfer between the light emitting layer and the electron transport layer. The 1,3, 5-triazine unit with strong electron absorption property is beneficial to improving the electron injection and transmission performance.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the green light phosphorescence device provided by the invention has a simple structure, and can avoid an exciton blocking/electron transmission layer.
(2) The organic micromolecule electron transport material provided by the invention has the advantages of simple synthesis and purification, low molecular weight (m/z of NaAN-m-TRZ is 611.7, m/z of NaAN-m-PhTRZ is 687.3) and high glass transition temperature (T of NaAN-m-TRZ)gT of NaAN-m-PhTRZ 150 ℃g158 deg.c and high electron mobility (mobility of 6.23 × 10 of NaAN-m-TRZ)-5–7.19×10-4cm2 V-1s-1@(2–5)×105V cm-1And mobility of NaAN-m-PhTRZ 4.51X 10-5–1.88×10-4cm2 V-1s-1@(3–6)×105V cm-1) And the like. The existing electron transport material BPTRZ-Py-TPO (m/z 814.9, T)g123 ℃, triplet energy level 2.88 eV; electron mobility of 4.66 × 10-5–3.21×10-4cm2 V-1s-1@(2–5)×105V cm-1(Chinese patent publication CN 110016053A).
(3) The bottom emission electroluminescence efficiencies of the NaAN-m-TRZ and the NaAN-m-PhTRZ are 65.3cd/A and 60.3cd/A respectively, and the corresponding external quantum efficiencies are 17.6 percent and 16.51 percent respectively; and the bottom emission efficiency of the similar BPTRZ-Py-TPO is 62.6 cd/A; the corresponding external quantum efficiency was 16.9% (table 1). The anthracene-based derivative has a low triplet level, should be less than 1.8eV, lower than the triplet level of the green phosphorescent material, while the triplet level of BPTRZ-Py-TPO is about 2.88 eV. In the bottom emission green phosphorescence device, NaAn-m-TRZ has high electroluminescent efficiency, which indicates that the twisted molecular structure can effectively inhibit energy transfer between the light emitting layer and the electron transport layer; and meanwhile, the doped Liq crystal is doped with Liq and shows high mobility.
(4) The NaAN-m-TRZ has the top emission electroluminescent efficiencies of 88.8cd/A and 77.8cd/A, and the corresponding external quantum efficiencies are 21.4% and 19.4%; the top emission efficiency of the similar BPTRZ-Py-TPO is 72.5 cd/A; the corresponding external quantum efficiency was 19.07% (table 1).
(5) The electron transport materials NaAN-m-TRZ and NaAN-m-PhTRZ can also be applied to high-efficiency single-layer organic blue light fluorescent and red light phosphorescent OLED devices.
Drawings
FIG. 1 is a current density-voltage-luminance curve of a NaAN-m-TRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 2 is a current efficiency-luminance curve of a NaAN-m-TRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 3 is a graph of power efficiency versus luminance for a NaAN-m-TRZ single layer doped electron transport layer high efficiency bottom emission green phosphorescent organic electroluminescent device.
FIG. 4 is a current density-voltage-luminance curve of a NaAN-m-TRZ single-layer doped electron transport layer high efficiency top-emitting green phosphorescent organic electroluminescent device.
FIG. 5 is a current efficiency-luminance curve of a NaAN-m-TRZ single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device.
FIG. 6 is a graph of power efficiency versus luminance for a NaAN-m-TRZ single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device.
FIG. 7 is a current density-voltage-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 8 is a current efficiency-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 9 is a power efficiency-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 10 is a current density-voltage-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high efficiency top-emitting green-emitting phosphorescent organic electroluminescent device.
FIG. 11 is a current efficiency-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high efficiency top-emitting green phosphorescent organic electroluminescent device.
FIG. 12 is a power efficiency-luminance curve of a NaAN-m-PhTRZ single layer doped electron transport layer high efficiency top emission green light phosphorescent organic electroluminescent device.
FIG. 13 is a graph of current density-voltage-luminance for a BPTRZ-Py-TPO single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device.
FIG. 14 is a graph of current efficiency versus luminance for a BPTRZ-Py-TPO single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device.
FIG. 15 is a graph of power efficiency vs. luminance for a BPTRZ-Py-TPO single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device.
FIG. 16 is a current density-voltage curve of organic small molecule electron transport materials NaAN-m-TRZ and Liq doped according to the mass ratio of 1:1 n-.
FIG. 17 is a current density-voltage curve of organic small molecule electron transport materials NaAN-m-PhTRZ and Liq doped according to the mass ratio of 1:1 n-.
Detailed Description
The present invention will be further described with reference to the following specific examples and drawings, but the embodiments of the present invention are not limited thereto.
Example 1
1. Naphthyl anthryl substituted triazine derivatives NaAN-m-TRZ and NaAN-m-PhTRZ are respectively used as single-layer doped electron transport layers, a vacuum evaporation method is adopted to prepare a high-efficiency green phosphorescent device, and a BPTRZ-Py-TPO device (prepared according to Chinese patent publication CN 110016053A) is used as a comparison, and performance characterization is carried out.
The high-efficiency green light phosphorescence device has the following structures:
bottom emission green phosphorescent device: ITO/P008: P-company (100nm, 4%)/HTL (15nm)/EBL (5nm)/HOST1: HOST2: green phosphorescent iridium complex (30nm, mass ratio 1:1:0.3)/ETM: Liq (30nm,1:1)/EIL/Al (2000). The doping ratios are mass ratios.
Top emission green phosphorescent device: Ag/ITO/P008: P-dock (147nm, 4%)/HTL (15nm)/EBL (5nm)/HOST1: HOST2: green phosphorescent iridium complex (30nm,1:1:0.3)/ETM: Liq (30nm,1:1)/EIL/Mg: Ag (15nm,1:9)/CP405(70 nm).
Wherein, P008 is P-dock used as a hole injection layer (P008, purchased from Beijing Ding materials science and technology Co., Ltd)), HTL is used as a hole transport layer, and EBL is used as a hole transport/exciton blocking layer; HOST1, HOST2 as a green phosphorescent HOST material (available from Taiwan Yi radium photoelectric materials Co., Ltd.); CP405 as a light extraction layer; liq is an 8-hydroxyquinoline lithium complex; EIL is an electron injection layer, and can be selected from active metals such as Yb and Liq and ionic salts thereof. Green phosphorescent iridium complex (Ir (ppy)2(m-mbppy); ETM ═ NaAN-m-TRZ, NaAN-m-PhTRZ, structural formula as follows:
the detailed preparation process of the organic electroluminescent device is as follows:
an Indium Tin Oxide (ITO) conductive glass substrate with the resistance of 10-20 omega/port is sequentially subjected to ultrasonic cleaning for 20min by deionized water, acetone, a detergent, deionized water and isopropanol. After oven drying, the treated ITO glass substrate was placed at 3X 10-4And (3) evaporating each organic functional layer and the metal cathode under the vacuum of Pa. The film thickness was measured using a Veeco Dektak150 step meter. The deposition rate of metal electrode evaporation and its thickness were determined using a Sycon Instrument thickness/velocimeter STM-100. The performance test results of the organic electroluminescent device are shown in fig. 1 to 6.
FIG. 1 is a current density-voltage-luminance graph of a NaAN-m-TRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device;
FIG. 2 is a graph of current efficiency versus luminance for a NaAN-m-TRZ single layer doped electron transport layer high efficiency bottom emission green phosphorescent organic electroluminescent device;
FIG. 3 is a graph of power efficiency vs. luminance for a NaAN-m-TRZ single layer doped electron transport layer high efficiency bottom emission green phosphorescent organic electroluminescent device.
FIG. 4 is a current density-voltage-luminance graph of a NaAN-m-TRZ single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device;
FIG. 5 is a graph of current efficiency versus luminance for a NaAN-m-TRZ single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device;
FIG. 6 is a graph of power efficiency vs. luminance for a NaAN-m-TRZ single layer doped electron transport layer high efficiency top emission green phosphorescent organic electroluminescent device.
FIG. 7 is a current density-voltage-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 8 is a current efficiency-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 9 is a power efficiency-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high-efficiency bottom-emission green-light phosphorescent organic electroluminescent device.
FIG. 10 is a current density-voltage-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high efficiency top-emitting green-emitting phosphorescent organic electroluminescent device.
FIG. 11 is a current efficiency-luminance curve of a NaAN-m-PhTRZ single-layer doped electron transport layer high efficiency top-emitting green phosphorescent organic electroluminescent device.
FIG. 12 is a power efficiency-luminance curve of a NaAN-m-PhTRZ single layer doped electron transport layer high efficiency top emission green light phosphorescent organic electroluminescent device.
(6) As shown in FIG. 2 and FIG. 8, the single-layer doped electron transport layer of NaAN-m-TRZ and NaAN-m-PhTRZ can efficiently emit green light phosphorescence organic electroluminescent device at 1000 cd.m-2The current efficiencies of the devices were 65.3cd/a and 60.3cd/a, respectively, and the corresponding external quantum efficiencies were 17.6% and 16.51%, respectively, at luminance of (1). And the efficiency of the BPTRZ-Py-TPO bottom-emitting green-emitting phosphorescent device is 62.6 cd/A; the corresponding external quantum efficiency was 16.9%.
(7) As shown in FIG. 5 and FIG. 11, the single-layer doped electron transport layer of NaAN-m-TRZ, NaAN-m-PhTRZ has high efficiency top emission green light phosphorescence organic electroluminescent device at 1000 cd.m-2The current efficiency and external quantum efficiency of the device reach 88.8cd/A, 77.8cd/A, 21.4% and 19.4% respectively at the luminance of (Table 1).
(8) As shown in FIG. 14, the top-emitting green-emitting phosphorescent device efficiency of BPTRZ-Py-TPO is 72.5 cd/A; the corresponding external quantum efficiency was 19.07% (table 1).
Table 1: data of characteristics of green phosphorescent device with single-layer doped electron transport layer
2. The electron mobility of the NaAN-m-TRZ and NaAN-m-PhTRZ single layer doped electron transport layers of this example were characterized. Single-electron devices (ITO/ETL: Liq (50% wt, 150nm)/Al, ETL ═ NaAN-m-TRZ, NaAN-m-PhTRZ) were prepared, and electron mobility was calculated by the space charge limited current SCLC method according to the current density-voltage curve. Liq is an 8-hydroxyquinoline lithium complex. 50% wt means that the mass ratio of Liq to NaAN-m-TRZ or NaAN-m-PhTRZ is 1: 1.
The detailed preparation process of the single-electron device is as follows:
an Indium Tin Oxide (ITO) conductive glass substrate with the resistance of 10-20 omega/port is sequentially subjected to ultrasonic cleaning for 20min by deionized water, acetone, a detergent, deionized water and isopropanol. After oven drying, the treated ITO glass substrate was placed at 3X 10-4And (3) evaporating an organic functional layer and a metal Al cathode under the vacuum of Pa. The film thickness was measured using a Veeco Dektak150 step meter. The deposition rate of metal electrode evaporation and its thickness were determined using a Sycon Instrument thickness/velocimeter STM-100. FIG. 10 is a current density-voltage curve of organic electron transport materials NaAN-m-TRZ and Liq doped at a mass ratio of 1:1 n-.
As shown in FIG. 6, the electron mobility of the organic small molecule electron transport layer NaAN-m-TRZ Liq of the present embodiment is 6.23 × 10 according to SCLC calculation-5-7.19×10-4cm2·V-1·s-1(@2-5×105V·cm-1)。
As shown in FIG. 17, the electron mobility of the organic small molecule electron transport layer NaAN-m-PhTRZ: Liq in this example is 4.51 × 10 by SCLC calculation-5-1.88×10-4cm2·V-1·s-1(@3-6×105V·cm-1)。
The above results indicate that high luminous efficiency is obtained for the green phosphorescent organic electroluminescent device with NaAN-m-TRZ as a single doped electron transport layer.
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 changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (6)
1. A single-layer doped electron transport layer green phosphorescent device is characterized by comprising an organic electron transport material with the following structure:
2. the single doped electron transport layer green phosphorescent device of claim 1, wherein: the single-layer doped electron transport layer green phosphorescent device is of a bottom emission or top emission structure.
3. The single layer doped electron transport layer phosphorescent green light device of claim 2, wherein the bottom emission phosphorescent green light device is structured as follows: ITO/HIL, p-dock/HTL/EBL/HOST, green light phosphorescent iridium complex/ETM, Liq/EIL/Al;
p-dock is used as a hole injection layer, HTL is used as a hole transport layer, and EBL is used as a hole transport/exciton blocking layer; HOST as a green phosphorescent HOST material; liq is an 8-hydroxyquinoline lithium complex; the EIL is an electron injection layer.
4. The single layer doped electron transporting layer phosphorescent green light device of claim 2, wherein the top emission phosphorescent green light device is structured as: Ag/ITO/HIL, p-dock/HTL/EB/HOST, green light phosphorescent iridium complex/ETM, Liq/EIL/Mg, Ag/CPL.
5. The single doped electron transport layer green phosphorescent device of claim 2, wherein: the EIL is one of Yb, Liq and ionic salt thereof.
6. The single doped electron transport layer green phosphorescent device of claim 2, wherein: the bottom-emitting or top-emitting hole injection layer, the hole transport/exciton blocking layer and the light-emitting layer are processed by a solution method or formed into a film by vacuum evaporation; the electron transport layer, the electron injection layer, the cathode, and the light extraction layer were formed by vacuum evaporation.
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| CN110283135A (en) * | 2019-06-28 | 2019-09-27 | 华南理工大学 | The pyrrolotriazine derivatives and the preparation method and application thereof that anthryl containing naphthalene replaces |
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| CN110283135A (en) * | 2019-06-28 | 2019-09-27 | 华南理工大学 | The pyrrolotriazine derivatives and the preparation method and application thereof that anthryl containing naphthalene replaces |
Non-Patent Citations (2)
| Title |
|---|
| 于军胜 田朝勇: "《OLED显示基础及产业化》", vol. 2015, 28 February 2015, 电子科技大学出版社, pages: 90 - 91 * |
| 肖运虹 王志铭: "《显示技术 第二版》", vol. 2018, 28 February 2018, 西安电子科技大学出版社, pages: 7 * |
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Application publication date: 20210416 |