CN112467058B - Ternary exciplex composite material main body and OLED device preparation method thereof - Google Patents
Ternary exciplex composite material main body and OLED device preparation method thereof Download PDFInfo
- Publication number
- CN112467058B CN112467058B CN202011347543.2A CN202011347543A CN112467058B CN 112467058 B CN112467058 B CN 112467058B CN 202011347543 A CN202011347543 A CN 202011347543A CN 112467058 B CN112467058 B CN 112467058B
- Authority
- CN
- China
- Prior art keywords
- electron
- layer
- injection layer
- exciplex
- ternary
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000002131 composite material Substances 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 239000010410 layer Substances 0.000 claims abstract description 226
- 239000000463 material Substances 0.000 claims abstract description 127
- 238000002347 injection Methods 0.000 claims abstract description 74
- 239000007924 injection Substances 0.000 claims abstract description 74
- 239000002346 layers by function Substances 0.000 claims abstract description 25
- 230000003111 delayed effect Effects 0.000 claims abstract description 17
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 230000000694 effects Effects 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 24
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical group [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 14
- 239000011787 zinc oxide Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- -1 9, 9-dioctylfluorenyl-2, 7-diyl Chemical group 0.000 claims description 6
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 4
- 229910001887 tin oxide Inorganic materials 0.000 claims description 4
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 3
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 2
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 2
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 claims description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical group [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 abstract description 6
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 230000002708 enhancing effect Effects 0.000 abstract description 3
- 238000010129 solution processing Methods 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 description 33
- 239000000370 acceptor Substances 0.000 description 31
- 238000000151 deposition Methods 0.000 description 14
- 229920000144 PEDOT:PSS Polymers 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical group C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 8
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 6
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 6
- 238000000137 annealing Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000969 carrier Substances 0.000 description 5
- 238000005286 illumination Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000005240 physical vapour deposition Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- UNGIWHLZSGNESD-UHFFFAOYSA-N 4-(3,5-dipyridin-4-ylphenyl)-2-methylpyrimidine Chemical compound N1=CC=C(C=C1)C=1C=C(C=C(C=1)C1=CC=NC=C1)C1=NC(=NC=C1)C UNGIWHLZSGNESD-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 101001102158 Homo sapiens Phosphatidylserine synthase 1 Proteins 0.000 description 1
- DNVSTRMCTBUNBP-UHFFFAOYSA-N N1=CC(=CC=C1)C1=C(C=CC=C1)N1C(N=CC(=C1)C1=C(C=CC=C1)C=1C=NC=CC=1)C Chemical compound N1=CC(=CC=C1)C1=C(C=CC=C1)N1C(N=CC(=C1)C1=C(C=CC=C1)C=1C=NC=CC=1)C DNVSTRMCTBUNBP-UHFFFAOYSA-N 0.000 description 1
- 102100039298 Phosphatidylserine synthase 1 Human genes 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000000231 atomic layer deposition Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012858 packaging process Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000004549 pulsed laser deposition Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
Landscapes
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a ternary exciplex composite material main body and preparation of an OLED device thereof, wherein the OLED device comprises: an anode, a cathode, an organic functional layer disposed between the anode and the cathode; the organic functional layer comprises a hole injection layer, an organic light-emitting layer, an electron transport layer and an electron injection layer which are sequentially arranged in the direction from the anode to the cathode; the organic light-emitting layer comprises a host composite material and a guest material, the host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, and the electron donor is
The first electron acceptor is
The second electron acceptor is
The guest material is selected from one or more of a thermal activity delayed fluorescence material, a triplet-triplet annihilation material, a fluorescence material and a phosphorescence material. The main body composite material has good electron transmission efficiency and thermal stability, is beneficial to enhancing the efficacy and the luminous efficiency of an OLED device, and is suitable for solution processing.
Description
Technical Field
The invention relates to the technical field of electroluminescent devices, in particular to a ternary exciplex composite material main body and preparation of an OLED device thereof.
Background
Organic light-emitting diodes (OLEDs for short) have the advantages of self-luminescence, fast response, wide visibility, low driving voltage, energy saving, lightness and thinness, flexible processing and the like, and greatly meet the requirement of consumers on continuous update of display technology. Meanwhile, the OLED device has wide application prospect and huge market demand in the field of illumination.
The Thermal Activated Delayed Fluorescence (TADF) material has an intramolecular electron donor (D) -electron acceptor (A) structure, the maximum theoretical efficiency can reach 100%, the singlet excited state and triplet excited state energy levels are close to 0.5-1.0 eV, and the TADF material is used as a main material of a light-emitting layer to form an OLED device and has the characteristics of high light-emitting efficiency, no need of Eu and Ir rare earth metal elements and low volume production cost; because the traditional single-component host material (1, 3-bis (carbazole-9-yl) benzene, abbreviated as mCP) has lower glass transition temperature (Tg) (-60 ℃) to deteriorate the performance of an OLED device, the new exciplex system host replaces the mCP host to be beneficial to solving the problems, and two materials with different existing transmission properties can be used for forming, so that the charge transmission capability is increased, the electron-hole transmission is more balanced, the driving voltage of light emission is reduced, and the performance and the stability of the device are improved. The existing exciplex main body system mainly focuses on the research of a binary D-A exciplex system, and the exciplex main body system with more than three elements is rarely reported, so that an OLED new structure system based on the ternary exciplex main body system has a space for further development.
Accordingly, the prior art is yet to be improved and developed.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide a ternary exciplex composite material host and preparation of an OLED device thereof, aims to solve the limitations of the traditional single host and OLED devices based on a binary exciplex host system, and opens up a new technical route.
The technical scheme of the invention is as follows:
a ternary exciplex composite host OLED device, wherein said OLED device comprises: an anode, a cathode, and a cathode disposed at the anodeAn organic functional layer between the cathode and the anode; the organic functional layer comprises a hole injection layer, an organic light-emitting layer, an electron transport layer and an electron injection layer which are sequentially arranged in the direction from the anode to the cathode; the organic light-emitting layer comprises a host composite material and a guest material, wherein the host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, and the electron donor is
The first electron acceptor is
The second electron acceptor is
The guest material is selected from one or more of a delayed thermal activity delayed fluorescence material, a triplet-triplet annihilation material, a fluorescent material, and a phosphorescent material.
A preparation method of a ternary exciplex composite material main body OLED device comprises the following steps:
providing an anode;
sequentially forming a hole injection layer, an organic light-emitting layer, an electron transport layer and an electron injection layer on the anode by a solution method, wherein the hole injection layer, the organic light-emitting layer, the electron transport layer and the electron injection layer form an organic functional layer;
forming a cathode on the organic functional layer to obtain an OLED device;
or,
providing a cathode;
forming an electron injection layer, an electron transport layer, an organic light emitting layer and a hole injection layer on the cathode in sequence by a solution method, wherein the electron injection layer, the electron transport layer, the organic light emitting layer and the hole injection layer form an organic functional layer;
forming an anode on the organic functional layer to obtain an OLED device;
the material of the organic light-emitting layer comprises a host complexThe host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, wherein the electron donor is
The first electron acceptor is
The second electron acceptor is
The guest material is selected from one or more of a thermal activity delayed fluorescence material, a triplet-triplet annihilation material, a fluorescence material and a phosphorescence material.
Has the beneficial effects that: the ternary exciplex formed by mixing the electron donor with the chemical structure and the two electron acceptors has good electron transmission efficiency and thermal stability, can effectively capture excitons and balance carriers, and is an organic light-emitting layer formed by a host composite material and one or more of a thermal activity delayed fluorescent material, a triplet-triplet annihilation material, a fluorescent material and a phosphorescent material as a guest material, so that the efficacy efficiency and the luminous efficiency of an OLED device are enhanced; meanwhile, the electron donor and the two electron acceptors of the ternary exciplex are organic micromolecules, so that the ternary exciplex is suitable for processing and preparing OLED devices by a solution method; in addition, the ternary exciplex widens the composition of the OLED exciplex main body system. A new technical route is formed. The OLED device obtained as described above can be used as a display device, a white light illumination device, and the like.
Drawings
Fig. 1 is a schematic diagram illustrating the operation principle of energy transfer of an organic light emitting layer formed by a binary exciplex host (a) and a ternary exciplex host (b) respectively as a host and a guest (e.g., TADF material) according to an embodiment of the present invention.
Fig. 2 is a schematic structural diagram of an upright OLED device according to an embodiment of the present invention.
FIG. 3 is a graph showing energy level comparison of materials of respective layers used for preparing OLED devices in examples 1 and 2 and comparative examples 1 and 2 in example 3 of the present invention.
Detailed Description
The invention provides a ternary exciplex composite material main body and preparation of an OLED device thereof, and the invention is further described in detail below in order to make the purpose, technical scheme and effect of the invention clearer and clearer. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The embodiment of the invention provides a ternary exciplex composite material main body OLED device, which comprises: the organic light-emitting diode comprises an anode, a cathode and an organic functional layer arranged between the anode and the cathode, wherein the organic functional layer comprises a hole injection layer, an organic light-emitting layer, an electron transport layer and an electron injection layer which are sequentially arranged in the direction from the anode to the cathode; the organic light-emitting layer comprises a host composite material and a guest material, wherein the host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, and the electron donor is
The first electron acceptor is
The second electron acceptor is
The guest material is selected from one or more of a thermal activity delayed fluorescence material, a triplet-triplet annihilation material, a fluorescence material and a phosphorescence material.
In this embodiment, the ternary exciplex formed by mixing the electron donor and the two electron acceptors with the above structure has good electron transport efficiency and thermal stability, can effectively capture excitons and balance carriers, is an organic light-emitting layer formed by a host composite material and one or more selected from a thermal activity delayed fluorescent material, a triplet-triplet annihilation material, a fluorescent material and a phosphorescent material as a guest material, and is beneficial to enhancing the efficacy efficiency and the light-emitting efficiency of the OLED device; meanwhile, the electron donor and the two electron acceptors of the ternary exciplex are organic micromolecules, so that the ternary exciplex is suitable for processing and preparing OLED devices by a solution method; in addition, the ternary exciplex widens the composition of the OLED exciplex main body system. The OLED device obtained as described above can be used as a display device, a white light illumination device, and the like.
Referring to fig. 1, specifically, the operating principle (b) of energy transfer of an organic light emitting layer formed by a host composite material and a guest material (e.g., TADF material) is compared with the operating principle (a) of energy transfer of an organic light emitting layer formed by a host composite material and a guest material (e.g., TADF material); it can be known that the organic light emitting layer formed by the host composite material and the guest material (e.g., TADF material) of the ternary exciplex has dual energy transfer channels, so that the organic light emitting layer has better electron transport efficiency, and can more effectively capture excitons and balance carriers, thereby enabling the OLED device based on the ternary exciplex to have better light emitting performance and efficiency.
In one embodiment, the mass ratio of the electron donor, the first electron acceptor, and the second electron acceptor is 1 to 10:1:1 to 10. Within the mass ratio range, the ternary exciplex formed by mixing the electron donor, the first electron acceptor and the second electron acceptor has better electron transmission efficiency and thermal stability, can more effectively capture excitons and balance carriers, and is more favorable for enhancing the efficacy efficiency and the luminous efficiency of the OLED device when being used as an organic luminous layer formed by a host material composite and a guest material. Preferably, the guest material is a thermally active delayed fluorescence material.
In one embodiment, the thermally active delayed fluorescence material is selected from
In one embodiment, the triplet-triplet annihilation (TTA) material may be selected from, but is not limited to
One or more of;
the fluorescent material may be selected from, but is not limited to
One or more of;
the phosphorescent material may be selected from, but is not limited to
One or more of (a).
In one embodiment, the mass ratio of the host composite material to the guest material is 1 to 100:1.
in one embodiment, the organic light emitting layer may have a thickness of 10 to 100nm, such as 10nm, 30nm, 50nm, 60nm, 100nm, and the like.
In one embodiment, other hole function layers may be further disposed between the anode and the organic light emitting layer, such as at least one of a hole transport layer and an electron blocking layer; when the hole injection layer and the hole transport layer (or the electron blocking layer) are provided at the same time, the hole injection layer is provided near the anode, and the hole transport layer (or the electron blocking layer) is provided near the organic light emitting layer; when the hole injection layer, the hole transport layer and the electron blocking layer are simultaneously provided, the hole injection layer is disposed near the anode, the electron blocking layer is disposed near the organic light emitting layer, and the hole transport layer is disposed between the hole injection layer and the electron blocking layer. The thickness of the hole injection layer is 50 to 80nm, for example, 50nm, 60nm, 80nm, or the like; the material of the hole injection layer may be selected from, but is not limited to, 2,3,6,7, 10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN), 4- (9- (2-ethylhexyl) -9H-carbazole-3, 6-diyl) diphenol (MO) 3 ) Poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT: PSS), poly (4-styrenesulfonic acid) (structure is
Abbreviated PSSA) modified (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (m-PEDOT: PSS), poly [ (9, 9-dioctylfluorenyl-2, 7-diyl) -co- (4, 4' - (N- (p-butylphenyl)) diphenylamine)](TFB), poly (9-vinylcarbazole) (PVK)) Poly [ bis (4-phenyl) (4-butylphenyl) amine](Poly-TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 1-bis [4- [ N, N ' -di (p-tolyl) amino group]Phenyl radical]Cyclohexane (TAPC),
One or more of (a). The thickness of the hole transport layer is 50 to 80nm, for example, 50nm, 60nm, 80nm, or the like; the material of the hole transport layer may be a hole transport layer material commonly used in the art. The thickness of the electron blocking layer is 5 to 20nm, for example, 5nm, 15nm, 20nm, or the like; the material of the electron blocking layer may be an electron blocking material commonly used in the art.
In one embodiment, another electronic function layer, such as a hole blocking layer, may be disposed between the cathode and the organic light emitting layer, and when an electron injection layer, an electron transport layer and a hole blocking layer are disposed between the cathode and the organic light emitting layer, the electron injection layer is disposed adjacent to the cathode, the hole blocking layer is disposed adjacent to the organic light emitting layer, and the electron transport layer is disposed between the electron injection layer and the hole blocking layer. The thickness of the electron injection layer is 1 to 10nm, for example, 1nm, 5nm, 10nm, or the like; the electron injection layer may be made of a material but are not limited to, 8-hydroxyquinoline-lithium (II)
Liq) or LiF. The thickness of the electron transport layer is 50 to 80nm, for example, 50nm, 60nm, 80nm, or the like. The material of the electron transport layer can be, but is not limited to
ZnO、TiO 2 、BaTiO 3 One or more of aluminum-doped zinc oxide, lithium-doped zinc oxide, magnesium-doped zinc oxide, cdS, znS, moS, WS and CuS; the thickness of the hole blocking layer is 5 to 20nm, for example, 5nm, 15nm, 20nm, or the like; the material of the hole blocking layer may be, but is not limited to
Or bis-4, 6- (3, 5-bis-4-pyridylphenyl) -2-methylpyrimidine or 4, 6-bis (3, 5-bis (3-pyridylphenyl) -2-methylpyrimidine or derivatives thereof.
In one embodiment, the material of the anode may be selected from, but not limited to, one or more of Indium Tin Oxide (ITO), aluminum doped zinc oxide (AZO), antimony doped tin oxide (ATO), and fluorine doped tin oxide (FTO).
In one embodiment, the material of the cathode may be selected from one or more of, but not limited to, al, ag, cu, and Au.
Specifically, the ternary exciplex composite host OLED device of the present embodiment can be configured to be of different types, that is, the ternary exciplex composite host OLED device can be configured to be an OLED device having a forward structure, and can also be configured to be an OLED device having an inverted structure. Taking a positive OLED device with a hole injection layer as a hole functional layer and an electron injection layer, an electron transport layer and a hole blocking layer as electron functional layers as an example, the structure of the OLED device is further described, as shown in fig. 2, the OLED device sequentially includes from bottom to top: an anode 10, a hole functional layer 20 (i.e., a hole injection layer), an organic light emitting layer 30, an electron functional layer 40 (including a hole blocking layer 41, an electron transport layer 42, and an electron injection layer 43), a cathode 50; the material of the organic light emitting layer 30 includes a host composite material and a guest material, the host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, wherein the electron donor is mCP, the first electron acceptor is DTDP-TRZ, and the second electron acceptor is OXD-7; the guest material is selected from one or more of a thermal activity delayed fluorescence material, a triplet-triplet annihilation material, a fluorescence material and a phosphorescence material.
The embodiment of the invention also provides a preparation method of the ternary exciplex composite material main body OLED device, which comprises the following steps: the method comprises the steps of preparing traditional upright devices (S10, S20, S30) and preparing inverted devices (S10 ', S20', S30 ').
S10, providing an anode;
s20, sequentially forming a hole injection layer, an organic light-emitting layer, an electron transport layer and an electron injection layer on the anode by a solution method, wherein the hole injection layer, the organic light-emitting layer, the electron transport layer and the electron injection layer form an organic functional layer;
s30, forming a cathode on the organic functional layer to obtain the OLED device;
or,
s10', providing a cathode;
s20', sequentially forming an electron injection layer, an electron transport layer, an organic light emitting layer and a hole injection layer on the cathode by a solution method, wherein the electron injection layer, the electron transport layer, the organic light emitting layer and the hole injection layer form an organic functional layer;
s30', forming an anode on the organic functional layer to obtain the OLED device;
the material of the organic light-emitting layer comprises a host composite material and a guest material, wherein the host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, and the electron donor is
The first electron acceptor is
The second electron acceptor is
The guest material is selected from thermally active delayed fluorescence material and triplet-triplet annihilationOne or more of a material, a fluorescent material, and a phosphorescent material.
In one embodiment, in step S20, at least one of a hole transport layer and an electron blocking layer may be sequentially formed before forming the organic light emitting layer; the hole transport layer and the electron blocking layer may be sequentially formed by a solution method, for example, before the organic light emitting layer. In step S30, before forming the electron transport layer, a hole blocking layer may be further formed; the hole blocking layer may be thermally evaporated or solution deposited, for example, by physical vapor deposition prior to formation of the electron transport layer. In step S20', a hole blocking layer may be further formed before the organic light emitting layer is formed on the cathode; the hole blocking layer may be formed by a physical vapor deposition thermal evaporation method or a solution method, for example, before forming the organic light emitting layer on the cathode. In step S30', at least one of an electron blocking layer and a hole transporting layer may be sequentially formed before the hole injection layer is formed; the electron blocking layer and the hole transporting layer may be sequentially formed by a physical vapor deposition thermal evaporation method or a solution method, for example, before the hole injection layer is formed. That is, other functional layers may be prepared in the OLED device of this embodiment, and the material selection and the thickness of each layer in the OLED device are the same as those described above, and are not described herein again.
In this embodiment, the preparation method of each layer may be a chemical method or a physical method, wherein the chemical method includes, but is not limited to, one or more of a chemical vapor deposition method, a continuous ion layer adsorption and reaction method, an anodic oxidation method, an electrolytic deposition method, and a coprecipitation method; the physical method includes, but is not limited to, one or more of solution method (such as spin coating, printing, knife coating, dip-coating, dipping, spraying, roll coating, casting, slit coating, or bar coating), evaporation method (such as thermal evaporation, electron beam evaporation, magnetron sputtering, or multi-arc ion plating), deposition method (such as physical vapor deposition, atomic layer deposition, pulsed laser deposition, etc.).
In one embodiment, the anode needs to be pretreated in order to obtain a high-quality hole-function layer when manufacturing the positive OLED device. The pretreatment process specifically comprises the following steps: the anode is cleaned and then treated with ultraviolet-ozone or oxygen plasma to further remove organic matter attached to the surface of the anode and increase the work function of the anode.
In one embodiment, the resulting OLED device is subjected to an encapsulation process. The packaging process can adopt a common machine for packaging and can also adopt manual packaging. Preferably, the oxygen content and the water content in the packaging treatment environment are both lower than 1ppm so as to ensure the stability of the device.
The present invention will be described in detail below with reference to specific examples.
EXAMPLE 1 preparation of ternary exciplex composite host OLED devices
The structure of the red light OLED device is ITO (anode)/m-PEDOT: PSS (hole injection layer, 60 nm)/AQb 1: mCP: DTDP-TRZ: OXD-7 (organic light emitting layer, 50nm, AQb1 as guest material, mass ratio of ternary exciplex mCP: DTDP-TRZ: OXD-7 is 35); the preparation method comprises the following steps:
(1) Spin-coating a 60nm hole injection layer (m-PEDOT: PSS) on ITO glass at 4000r/min, and annealing at 120 deg.C for 10min in a glove box;
(2) In a nitrogen atmosphere, a 50nm organic light-emitting layer was spin-coated on the hole injection layer at a rotation speed of 1000r/min (AQb 1: mCP: DTDP-TRZ: OXD-7 mass ratio of 10;
(3) At a vacuum degree of 10 -5 Depositing a 15nm hole blocking layer (DPEPO) on the organic light-emitting layer under mbar;
(4) At a vacuum degree of 10 -5 Depositing a 60nm electron transport layer (material TmPyPB) on the hole barrier layer under mbar;
(5) At a vacuum degree of 10 -5 Depositing a 1nm electron injection layer (Liq material) on the electron transport layer under mbar;
(6) At a vacuum degree of 10 -5 Coating a layer of Al with a thickness of 100nm on the electron injection layer under mbar as cathode to obtainTo red OLED devices.
Comparative example 1 preparation of DTDP-TRZ-based OLED device
The structure of the red OLED device is ITO (anode)/m-PEDOT: PSS (hole injection layer, 60 nm)/AQb 1 (10 wt%). DTDP-TRZ (organic light emitting layer, 50nm, AQb1 as guest material, DTDP-TRZ as host material)/DPEPO (hole blocking layer, 15 nm)/TmPyPB (electron transport layer, 60 nm)/Liq (electron injection layer, 1 nm)/Al (cathode, 100 nm); the preparation method comprises the following steps:
(1) Spin-coating a 60nm hole injection layer (made of m-PEDOT: PSS) on ITO glass at the rotating speed of 4000r/min, and annealing in a glove box at 120 ℃ for 15min;
(2) In a nitrogen atmosphere, an organic luminescent layer with the thickness of 50nm is spin-coated on the hole injection layer at the rotating speed of 1000r/min, the content of AQb1 is 10wt%, and the content of DTDP-TRZ is 90wt%, and annealing is carried out for 10min at the temperature of 50 ℃;
(3) At a vacuum degree of 10 -5 A 15nm hole blocking layer (DPEPO) is deposited on the organic light-emitting layer under mbar;
(4) At a vacuum degree of 10 -5 Depositing a 60nm electron transport layer (material TmPyPB) on the hole blocking layer under mbar;
(5) At a vacuum degree of 10 -5 Depositing a 1nm electron injection layer (Liq material) on the electron transport layer under mbar;
(6) At a vacuum degree of 10 -5 And depositing a layer of Al with the thickness of 100nm on the electron injection layer as a cathode under the mbar condition to obtain the red light OLED device.
Example 2 preparation of OLED devices based on ternary exciplex
The structure of the red OLED device is ITO (anode)/m-PEDOT: PSS (hole injection layer, 60 nm)/AQb 1: mCP: TDP-TRZ (TDP-TRZ structure is
) OXD-7 (organic light-emitting layer, 50nm, AQb1 as guest material, mass ratio of ternary non-exciplex mCP: TDP-TRZ: OXD-7 is 35)In-layer, 1 nm)/Al (cathode, 100 nm); the preparation method of the red light OLED device comprises the following steps:
(1) Spin-coating a 60nm hole injection layer (made of m-PEDOT: PSS) on ITO glass at the rotating speed of 4000r/min, and annealing in a glove box at 120 ℃ for 10min;
(2) An organic light-emitting layer (AQb 1: mCP: TDP-TRZ: OXD-7 mass ratio of 10: 30) of 50nm was spin-coated on the hole injection layer in a nitrogen atmosphere, and annealing was performed at 50 ℃ for 10min;
(3) At a vacuum degree of 10 -5 A 15nm hole blocking layer (DPEPO) is deposited on the organic light-emitting layer under mbar;
(4) At a vacuum degree of 10 -5 Depositing a 60nm electron transport layer (material TmPyPB) on the hole barrier layer under mbar;
(5) At a vacuum degree of 10 -5 Depositing a 1nm electron injection layer (Liq material) on the electron transport layer under mbar;
(6) At a vacuum degree of 10 -5 And depositing a layer of Al with the thickness of 100nm on the electron injection layer as a cathode under the mbar condition to obtain the red light OLED device.
Comparative example 2 preparation of TDP-TRZ-based OLED device
The structure of the red OLED device is ITO (anode)/m-PEDOT: PSS (hole injection layer, 60 nm)/AQb 1 (10 wt%). TDP-TRZ (organic light emitting layer, 50nm, AQb1 as guest material, TDP-TRZ as host material)/DPEPO (hole blocking layer, 15 nm)/TmPyPB (electron transport layer, 60 nm)/Liq (electron injection layer, 1 nm)/Al (cathode, 100 nm); the preparation method of the red OLED device comprises the following steps:
(1) Spin-coating a 60nm hole injection layer (m-PEDOT: PSS) on the ITO glass, and annealing at 140 deg.C in air for 15min;
(2) In a nitrogen atmosphere, a 50nm organic light emitting layer (AQb 1 content 10wt%, 90 wt%) was spin-coated on the hole injection layer, and annealed at 50 ℃ for 10min;
(3) At a vacuum degree of 10 -5 A 15nm hole blocking layer (DPEPO) is deposited on the organic light-emitting layer under mbar;
(4) At a vacuum degree of 10 -5 Depositing a 60nm electron transport layer (material TmPyPB) on the hole blocking layer under mbar;
(5) At a vacuum degree of 10 -5 Depositing a 1nm electron injection layer (Liq material) on the electron transport layer under mbar;
(6) At a vacuum degree of 10 -5 And depositing a layer of 100nm Al on the electron injection layer as a cathode under mbar to obtain the red light OLED device.
EXAMPLE 3 Performance test analysis of OLED devices
The energy levels of the materials of the respective layers used to fabricate the OLED devices of examples 1 and 2 and comparative examples 1 and 2 are shown in fig. 3, and it can be seen that TDP-TRZ and DTDP-TRZ having similar structures have slightly different energy levels.
The light emitting properties (luminance of 10 cd. M) of the OLED devices prepared in examples 1 and 2 and comparative examples 1 and 2 -2 Time on voltage (V) on ) Characteristic emission peak (EL) peak A/nm) brightness of 10-1000 cd.m -2 Maximum Current Efficiency (CE) in the range max /cd·A -1 ) Maximum Power Efficiency (PE) max /lm·W -1 ) And maximum External Quantum Efficiency (EQE) max (%)) and a luminance of 100cd · m -2 The results of the test were shown in Table 1, based on the International Commission on illumination coordinates (CIE, (x, y))). It is known that, compared with DTDP-TRZ, the luminophores formed by taking ternary exciplexes (mCP, TDP-TRZ and OXD-7) as host composite materials and TADF materials as guest materials have better luminescence property.
TABLE 1
The ratio of the performance parameter of the OLED device prepared in the example in table 1 to the performance parameter of the OLED device prepared in the corresponding comparative example was used as the gain of the performance parameter of the OLED device prepared in the example, and the gain was converted to obtain the partial performance parameters (CE) of the OLED device prepared in the examples 1 and 2 max 、PE max And EQE max ) The gain is shown in the table2, the EQE gain of the OLED device prepared in example 1 is 1.3 times the EQE gain of the OLED device prepared in example 2; shows that: compared with a ternary non-exciplex, the ternary exciplex has better application prospect as a main composite material.
TABLE 2
In summary, the present invention provides a ternary exciplex composite material host and a preparation method of an OLED device thereof, the ternary exciplex adopted in the present invention, which is formed by mixing an electron donor having the above structure and two electron acceptors, has good electron transport efficiency and thermal stability, can effectively capture excitons and balance carriers, is a host composite material, and is an organic light emitting layer formed by using one or more selected from a thermally active delayed fluorescent material, a triplet-triplet annihilation material, a fluorescent material and a phosphorescent material as a guest material; the efficiency and the luminous efficiency of the OLED device are enhanced; meanwhile, the electron donor and the two electron acceptors of the ternary exciplex are organic micromolecules, so that the ternary exciplex is suitable for processing and preparing OLED devices by a solution method; in addition, the ternary exciplex widens the composition of the OLED exciplex main body system. The OLED device obtained as described above can be used as a display device, a white light illumination device, and the like.
It is to be understood that the invention is not limited to the examples described above, but that modifications and variations may be effected thereto by those of ordinary skill in the art in light of the foregoing description, and that all such modifications and variations are intended to be within the scope of the invention as defined by the appended claims.
Claims (2)
1. A ternary exciplex composite host OLED device, comprising: an anode, a cathode, and an organic functional layer disposed between the anode and the cathode; the organic functional layer comprises a hole injection layer, an organic light-emitting layer, an electron transport layer and an electron injection layer which are sequentially arranged in the direction from the anode to the cathode; what is needed isThe organic light-emitting layer comprises a host composite material and a guest material, wherein the host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, and the electron donor is a ternary exciplex
Or
The first electron acceptor is
The second electron acceptor is
Or
The guest material is selected from one or more of a thermal activity delayed fluorescence material, a triplet-triplet annihilation material, a fluorescence material and a phosphorescence material; the mass ratio of the electron donor to the first electron acceptor to the second electron acceptor is 1 to 10:1:1 to 10;
the thermally active delayed fluorescence material is selected from
、
One or more of;
the triplet-triplet annihilation material is selected from
One or more of (a);
the fluorescent material is selected from
And
one or more of (a);
the phosphorescent material is selected from
One or more ofA plurality of types;
the mass ratio of the host composite material to the guest material is 1-100: 1;
the material of the hole injection layer is 2,3,6,7, 10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene, 4- (9- (2-ethylhexyl) -9H-carbazole-3, 6-diyl) diphenol, poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid), poly (4-styrenesulfonic acid) -modified (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid), poly [ (9, 9-dioctylfluorenyl-2, 7-diyl) -co- (4, 4' - (N- (p-butylphenyl)) diphenylamine)]Poly (9-vinylcarbazole), poly [ bis (4-phenyl) (4-butylphenyl) amine]N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine, 1-bis [4- [ N, N ' -di (p-tolyl) amino group]Phenyl radical]Cyclohexane,
And
one or more of;
the material of the electron transport layer is
ZnO、TiO 2 、BaTiO 3 One or more of aluminum-doped zinc oxide, lithium-doped zinc oxide, magnesium-doped zinc oxide, cdS, znS, moS, WS and CuS;
the material of the electron injection layer is 8-hydroxyquinoline-lithium or LiF;
the anode is made of one or more materials selected from indium tin oxide, aluminum-doped zinc oxide, antimony-doped tin oxide and fluorine-doped tin oxide;
the cathode is made of one or more materials selected from Al, ag, cu and Au.
2. A method of making a ternary exciplex composite host OLED device as recited in claim 1, comprising the steps of:
providing an anode;
sequentially forming a hole injection layer, an organic light-emitting layer, an electron transport layer and an electron injection layer on the anode by a solution method, wherein the hole injection layer, the organic light-emitting layer, the electron transport layer and the electron injection layer form an organic functional layer;
forming a cathode on the organic functional layer to obtain the OLED device;
or,
providing a cathode;
forming an electron injection layer, an electron transport layer, an organic light-emitting layer and a hole injection layer on the cathode in sequence by a solution method, wherein the electron injection layer, the electron transport layer, the organic light-emitting layer and the hole injection layer form an organic functional layer;
forming an anode on the organic functional layer to obtain the OLED device;
the material of the organic light-emitting layer comprises a host composite material and a guest material, wherein the host composite material is a ternary exciplex formed by mixing an electron donor, a first electron acceptor and a second electron acceptor, and the electron donor is
The first electron acceptor is
The second electron acceptor is
The guest material is selected from thermally activated delayed fluorescenceOne or more of a light material, a triplet-triplet annihilation material, a fluorescent material, and a phosphorescent material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011347543.2A CN112467058B (en) | 2020-11-26 | 2020-11-26 | Ternary exciplex composite material main body and OLED device preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011347543.2A CN112467058B (en) | 2020-11-26 | 2020-11-26 | Ternary exciplex composite material main body and OLED device preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112467058A CN112467058A (en) | 2021-03-09 |
| CN112467058B true CN112467058B (en) | 2023-03-07 |
Family
ID=74808597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011347543.2A Active CN112467058B (en) | 2020-11-26 | 2020-11-26 | Ternary exciplex composite material main body and OLED device preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112467058B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115377306A (en) * | 2021-09-28 | 2022-11-22 | 广东聚华印刷显示技术有限公司 | Organic light emitting diode, manufacturing method thereof and display device |
| GB2624715A (en) * | 2022-11-28 | 2024-05-29 | Sumitomo Chemical Co | Composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109817818A (en) * | 2019-01-31 | 2019-05-28 | 云谷（固安）科技有限公司 | A kind of organic electroluminescence device and display device |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10340470B2 (en) * | 2016-02-23 | 2019-07-02 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element, display device, electronic device, and lighting apparatus |
| CN109994626B (en) * | 2017-12-29 | 2021-04-02 | 中节能万润股份有限公司 | Organic light emitting composite material and organic light emitting device including the same |
-
2020
- 2020-11-26 CN CN202011347543.2A patent/CN112467058B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109817818A (en) * | 2019-01-31 | 2019-05-28 | 云谷（固安）科技有限公司 | A kind of organic electroluminescence device and display device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112467058A (en) | 2021-03-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI499105B (en) | Organic optoelectronic device and method for manufacturing the same | |
| US7528003B2 (en) | Organic photoelectric device with improved electron transport efficiency | |
| US7074500B2 (en) | Light emitting component comprising organic layers | |
| JP4024754B2 (en) | Light emitting device having organic layer | |
| KR101003267B1 (en) | Organic Light Emitting Device and Method for Manufacturing the Same | |
| US6351067B2 (en) | Organic electroluminescent device with improved hole injecting structure | |
| US20090001878A1 (en) | Organic electroluminescent device | |
| JP2009060012A (en) | Organic field-effect element and manufacturing method therefor, and display device | |
| CN112467058B (en) | Ternary exciplex composite material main body and OLED device preparation method thereof | |
| KR101973207B1 (en) | Anode including metal oxides and an organic light emitting device having the anode | |
| US8569743B2 (en) | Light-emitting component | |
| KR102378424B1 (en) | organic light emitting device | |
| KR101419809B1 (en) | Inverted organic light-emitting diode and display apparatus including the same | |
| WO2016188042A1 (en) | Electroluminescent component, manufacturing method therefor, display substrate, and display device | |
| CN112349857B (en) | Low-roll-off fluorescent organic electroluminescent device and preparation method thereof | |
| CN101222027B (en) | Organic light-emitting device and method for producing the same | |
| US20220131101A1 (en) | Organic light emitting device, method of manufacturing same, and display panel | |
| CN108649130A (en) | A kind of lamination blue light organic electroluminescence device and its manufacturing process | |
| KR100859821B1 (en) | Organic semiconductor devices having double interfacial layers | |
| CN104183718A (en) | Organic light emission diode and preparation method thereof | |
| CN113328045A (en) | Light emitting device and light emitting apparatus | |
| CN113555511A (en) | Light emitting device, display panel and display apparatus | |
| KR100595928B1 (en) | Organic light emitting diode having dotted-line doped emission layer with mixed host materials | |
| CN104183713A (en) | Top-emission organic light emission diode and preparation method thereof | |
| CN104183761A (en) | Inverted organic light emission diode and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |