CN110016040A - Thermal activation delayed fluorescence material and organic light-emitting diode (OLED) display apparatus - Google Patents
Thermal activation delayed fluorescence material and organic light-emitting diode (OLED) display apparatus Download PDFInfo
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- CN110016040A CN110016040A CN201910315698.9A CN201910315698A CN110016040A CN 110016040 A CN110016040 A CN 110016040A CN 201910315698 A CN201910315698 A CN 201910315698A CN 110016040 A CN110016040 A CN 110016040A
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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Abstract
It includes the structure as shown in formula (I) that the present invention, which discloses a kind of thermal activation delayed fluorescence material and organic light-emitting diode (OLED) display apparatus, thermal activation delayed fluorescence material:Wherein R is selected from the alkyl of oxygen, sulphur or C1-C3.
Description
Technical field
The invention relates to a kind of organic photoelectrical material technical fields, in particular to a kind of thermal activation delayed fluorescence
Material and organic light-emitting diode (OLED) display apparatus.
Background technique
Light emitting guest material is one of the principal element for influencing organic light-emitting diode (OLED) display apparatus luminous efficiency.It is general and
Speech, the light emitting guest material that organic light-emitting diode (OLED) display apparatus uses are fluorescent material, usually aobvious in Organic Light Emitting Diode
The exciton ratio for showing the singlet state in equipment and triplet is 1:3, therefore the interior quantum of organic light-emitting diode (OLED) display apparatus is imitated
Rate (internal quantum efficiency, IQE) can only achieve 25%, and the application of fluorescence electroluminescent device is limited
System.Effect of Spin-orbit Coupling of the heavy metal complex phosphor material based on heavy atom, thus can simultaneously using singlet state and
Triplet exciton and realize 100% internal quantum efficiency.However, usually used heavy metal is all that iridium (Ir) or platinum (Pt) etc. are expensive
Heavy metal, and heavy metal complex phosphorescent light-emitting materials must also be improved in terms of blue light material.Pure organic thermal activation delay is glimmering
Luminescent material has energy level difference (the Lowest single-triplet energy gap (Δ of lower minimum single triplet
EST)), triplet exciton can return to list by reversed intersystem crossing (reverse intersystem crossing, RISC)
Weight state, then shone by radiation transistion to ground state, it, can also be with so as to utilize singlet excitons and triplet exciton simultaneously
Realize 100% internal quantum efficiency.
For thermal activation delayed fluorescence material, Gao Fanxiang intersystem crossing constant and high photoluminescence quantum yield are to prepare
The necessary condition of high efficiency organic light-emitting diode (OLED) display apparatus.Currently, having the thermal activation delayed fluorescence material of above-mentioned condition
Still compare shortage for heavy metal complex.
Therefore, it is necessary to a kind of novel thermal activation delayed fluorescence material is provided, to solve the problems of prior art.
Summary of the invention
The embodiment of the present invention provides a kind of thermal activation delayed fluorescence material, including the structure as shown in formula (I):
Wherein, R is selected from the alkyl of oxygen, sulphur or C1-C3.
In one embodiment of this invention, thermal activation delayed fluorescence material is as follows:
In one embodiment of this invention, thermal activation delayed fluorescence material is as follows:
In one embodiment of this invention, the thermal activation delayed fluorescence material is as follows:
Another embodiment of the present invention provides a kind of organic light-emitting diode (OLED) display apparatus, including anode, cathode and it is located at
Organic function layer between anode and cathode, organic function layer include thermal activation delayed fluorescence material, thermal activation delayed fluorescence material
Material includes the structure as shown in formula (I):
Wherein, R is selected from the alkyl of oxygen, sulphur or C1-C3.
In one embodiment of this invention, thermal activation delayed fluorescence material is as follows:
In one embodiment of this invention, thermal activation delayed fluorescence material is as follows:
In one embodiment of this invention, thermal activation delayed fluorescence material is as follows:
In one embodiment of this invention, thermal activation delayed fluorescence material conduct in organic light-emitting diode (OLED) display apparatus
Fluorescent host material.
In one embodiment of this invention, thermal activation delayed fluorescence material conduct in organic light-emitting diode (OLED) display apparatus
Electron transport material.
Compared to prior art, thermal activation delayed fluorescence material of the invention has the energy level of lower minimum single triplet
Difference, the property of Gao Fanxiang intersystem crossing constant and high photoluminescence quantum yield, and then realize that there is having for high-luminous-efficiency
Machine emitting diode display device.
Detailed description of the invention
Fig. 1 is the embodiment of the present inventionHighest electronics occupy track (HOMO) with most
Low electronics does not occupy track (LUMO) distribution map；
Fig. 2 is the embodiment of the present inventionHighest electronics occupy track (HOMO)
Track (LUMO) distribution map is not occupied with minimum electronics；
Fig. 3 is the embodiment of the present inventionHighest electronics occupy track
(HOMO) track (LUMO) distribution map is not occupied with minimum electronics；
Fig. 4 is photoluminescence spectra of the thermal activation delayed fluorescence material of the embodiment of the present invention in toluene solution；And
Fig. 5 is that the thermal activation delayed fluorescence material of the embodiment of the present invention is set as the organic light-emitting diode display of luminescent layer
Standby schematic diagram.
Specific embodiment
The molecular structure that there is general thermal activation delayed fluorescence material electron donor and electron acceptor to combine, the present invention are real
Example is applied by the structure of change electron acceptor unit, so that electron acceptor unit has different electron acceptabilities, and is increased
The luminous efficiency of thermal activation delayed fluorescence material, and then realize the organic light-emitting diode (OLED) display apparatus with high-luminous-efficiency.
The embodiment of the present invention provides a kind of thermal activation delayed fluorescence material, including the structure as shown in formula (I):
Wherein, R is selected from the alkyl of oxygen, sulphur or C1-C3.Preferably, thermal activation delayed fluorescence material be selected from byAndComposed group.
The synthesis step of the thermal activation delayed fluorescence material of different embodiments of the invention described further below.Synthesis step it is as follows:
It is added in bis- mouthfuls of bottles of 250mL first(1.62g, 5mmol), phenoxazine (2.20g,
12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), then in gloves
NaOt-Bu (1.16g, 12mmol) is added in two mouthfuls of bottles in case, and it is not aqueous and oxygen to squeeze into 100mL down in an argon atmosphere
Toluene and 120 DEG C react 24 hours.After reaction solution is cooled to room temperature, reaction solution is poured into 200mL ice water, and with dichloro
Methane extracts three times, merges organic phase, dries and is spin-dried for, then passes through silica gel column chromatography, wherein the body of methylene chloride and n-hexane
Product ratio is 2:1, isolates and purifies, finally obtains light blue powder 1.6g, productYield be
60%.Product appraising datum:1H NMR(300MHz,CD2Cl2,δ):8.11(s,2H),7.19-7.14(m,4H),7.05-6.96
(m,12H),6.70(s,2H)。
Synthesis step it is as follows:
It is added in bis- mouthfuls of bottles of 250mL first(1.71g, 5mmol), phenoxazine (2.20g,
12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), then in gloves
NaOt-Bu (1.16g, 12mmol) is added in two mouthfuls of bottles in case, and it is not aqueous and oxygen to squeeze into 100mL down in an argon atmosphere
Toluene and 120 DEG C react 24 hours.After reaction solution is cooled to room temperature, reaction solution is poured into 200mL ice water, and with dichloro
Methane extracts three times, merges organic phase, dries and is spin-dried for, then passes through silica gel column chromatography, wherein the body of methylene chloride and n-hexane
Product ratio is 2:1, isolates and purifies, finally obtains light blue powder 1.5g, productProduction
Rate is 55%.Product appraising datum:1H NMR(300MHz,CD2Cl2,δ):8.12(s,2H),7.20-7.14(m,12H),
6.96-6.89(m,2H),6.70(s,2H)。
Synthesis step it is as follows:
It is added in bis- mouthfuls of bottles of 250mL first(1.76g, 5mmol), phenoxazine (2.20g,
12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), then in gloves
NaOt-Bu (1.16g, 12mmol) is added in two mouthfuls of bottles in case, and it is not aqueous and oxygen to squeeze into 100mL down in an argon atmosphere
Toluene and 120 DEG C react 24 hours.After reaction solution is cooled to room temperature, reaction solution is poured into 200mL ice water, and with dichloro
Methane extracts three times, merges organic phase, dries and is spin-dried for, then passes through silica gel column chromatography, wherein the body of methylene chloride and n-hexane
Product ratio is 2:1, isolates and purifies, finally obtains light blue powder 1.8g, productProduction
Rate is 65%.Product appraising datum:1H NMR(300MHz,CD2Cl2,δ):8.46(s,2H),7.20-7.14(m,4H),7.05-
6.96(m,12H),6.71(s,2H),1.69(s,6H)。
It is the embodiment of the present invention with reference to Fig. 1, Fig. 1Highest electronics occupy track
(HOMO) track (LUMO) distribution map is not occupied with minimum electronics.
Minimum singlet state (S1), lowest triplet state energy level (T1) and electrochemistry energy level
It is as shown in table 1 below:
Table 1
It is the embodiment of the present invention with reference to Fig. 2, Fig. 2Highest electronics occupy rail
Road (HOMO) and minimum electronics do not occupy track (LUMO) distribution map.
Minimum singlet state (S1) and lowest triplet state energy level (T1), electrification
It is as shown in table 2 below to learn energy level:
Table 2
It is the embodiment of the present invention with reference to Fig. 3, Fig. 3Highest electronics occupy
Track (HOMO) and minimum electronics do not occupy track (LUMO) distribution map.
Minimum singlet state (S1) and lowest triplet state energy level (T1), electrification
It is as shown in table 3 below to learn energy level:
Table 3
It is thermal activation delayed fluorescence material (compound I, compound II and the chemical combination of the embodiment of the present invention with reference to Fig. 4, Fig. 4
Object II) photoluminescence spectra in toluene solution.
Another embodiment of the present invention provides a kind of organic light-emitting diode (OLED) display apparatus, including anode, cathode and it is located at
Organic function layer between anode and cathode, organic function layer include thermal activation delayed fluorescence material, thermal activation delayed fluorescence material
Material includes structure as follows:
Specifically, the thermal activation delayed fluorescence material with above-mentioned chemical structure is in organic light-emitting diode (OLED) display apparatus
In can be used as fluorescent host material or electron transport material.
With reference to Fig. 5, the thermal activation delayed fluorescence material of the embodiment of the present invention is aobvious as the Organic Light Emitting Diode of luminescent layer
Show that equipment includes glass and electro-conductive glass (ITO) layer 10, hole injection layer 20, hole transmission layer 30, luminescent layer 40, electron-transport
Layer 50 and cathode layer 60.In addition, organic light-emitting diode (OLED) display apparatus can be completed by method known to technical field, therefore
It repeats no more.
Electric current, brightness and the voltage characteristic of organic light-emitting diode (OLED) display apparatus are by with corrected two pole of silicon photoelectricity
The source the Keithley measuring system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) of pipe
It completes, electroluminescent spectrum is by French JY company SPEX CCD3000 spectrometer measurement, and all measurements are normal big
It is completed in air pressure and room temperature.
Organic light-emitting diode (OLED) display apparatus (I, II and III) is respectively using containing
The performance data of thermal activation delayed fluorescence material is as shown in table 4 below:
Table 4
Thermal activation delayed fluorescence material of the invention has alters between the energy level difference of lower minimum single triplet, high inverse system
The more property of constant and high photoluminescence quantum yield, and then realize the organic light-emitting diode display with high-luminous-efficiency
Equipment.
Although the present invention is described in conjunction with its specific embodiment, it should be understood that many substitutions, modification and variation pair
It will be apparent in those skilled in the art.Therefore, it is intended to comprising falling into the scope of the appended claims
Interior all substitutions, modification and variation.
Claims (10)
1. a kind of thermal activation delayed fluorescence material, which is characterized in that including the structure as shown in formula (I):
Wherein, R is selected from the alkyl of oxygen, sulphur or C1-C3.
2. thermal activation delayed fluorescence material as described in claim 1, which is characterized in that the thermal activation delayed fluorescence material is such as
Shown in lower:
3. thermal activation delayed fluorescence material as described in claim 1, which is characterized in that the thermal activation delayed fluorescence material is such as
Shown in lower:
4. thermal activation delayed fluorescence material as described in claim 1, which is characterized in that the thermal activation delayed fluorescence material is such as
Shown in lower:
5. a kind of organic light-emitting diode (OLED) display apparatus, which is characterized in that including anode, cathode and be located at the anode and institute
The organic function layer between cathode is stated, the organic function layer includes thermal activation delayed fluorescence material, and the thermal activation delay is glimmering
Luminescent material includes the structure as shown in formula (I):
Wherein, R is selected from the alkyl of oxygen, sulphur or C1-C3.
6. organic light-emitting diode (OLED) display apparatus as claimed in claim 5, which is characterized in that the thermal activation delayed fluorescence material
Material is as follows:
7. organic light-emitting diode (OLED) display apparatus as claimed in claim 5, which is characterized in that the thermal activation delayed fluorescence material
Material is as follows:
8. organic light-emitting diode (OLED) display apparatus as claimed in claim 5, which is characterized in that the thermal activation delayed fluorescence material
Material is as follows:
9. organic light-emitting diode (OLED) display apparatus as claimed in claim 5, which is characterized in that the thermal activation delayed fluorescence material
Material is used as fluorescent host material in the organic light-emitting diode (OLED) display apparatus.
10. organic light-emitting diode (OLED) display apparatus as claimed in claim 5, which is characterized in that the thermal activation delayed fluorescence
Material is used as electron transport material in the organic light-emitting diode (OLED) display apparatus.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910315698.9A CN110016040A (en) | 2019-04-19 | 2019-04-19 | Thermal activation delayed fluorescence material and organic light-emitting diode (OLED) display apparatus |
| PCT/CN2019/091050 WO2020211181A1 (en) | 2019-04-19 | 2019-06-13 | Thermally-activated delayed fluorescent material and organic light emitting diode display device |
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| CN201910315698.9A CN110016040A (en) | 2019-04-19 | 2019-04-19 | Thermal activation delayed fluorescence material and organic light-emitting diode (OLED) display apparatus |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113620973A (en) * | 2021-07-16 | 2021-11-09 | 西北工业大学 | Thermal activation delayed fluorescent material and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150333271A1 (en) * | 2014-05-19 | 2015-11-19 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light emitting device including the same |
| CN105503766A (en) * | 2015-12-18 | 2016-04-20 | 昆山国显光电有限公司 | Thermal activation delayed fluorescent material and organic electroluminescent device |
| CN106103441A (en) * | 2014-03-11 | 2016-11-09 | 保土谷化学工业株式会社 | There is spiro-compound, luminescent material and the organic electroluminescence device of azepine fluorenes ring structure |
| CN106170528A (en) * | 2014-01-17 | 2016-11-30 | 九州有机光材股份有限公司 | Luminescent material, organic illuminating element and compound |
| US20180237460A1 (en) * | 2017-02-23 | 2018-08-23 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
-
2019
- 2019-04-19 CN CN201910315698.9A patent/CN110016040A/en active Pending
- 2019-06-13 WO PCT/CN2019/091050 patent/WO2020211181A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106170528A (en) * | 2014-01-17 | 2016-11-30 | 九州有机光材股份有限公司 | Luminescent material, organic illuminating element and compound |
| CN106103441A (en) * | 2014-03-11 | 2016-11-09 | 保土谷化学工业株式会社 | There is spiro-compound, luminescent material and the organic electroluminescence device of azepine fluorenes ring structure |
| US20150333271A1 (en) * | 2014-05-19 | 2015-11-19 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light emitting device including the same |
| CN105503766A (en) * | 2015-12-18 | 2016-04-20 | 昆山国显光电有限公司 | Thermal activation delayed fluorescent material and organic electroluminescent device |
| US20180237460A1 (en) * | 2017-02-23 | 2018-08-23 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113620973A (en) * | 2021-07-16 | 2021-11-09 | 西北工业大学 | Thermal activation delayed fluorescent material and preparation method and application thereof |
| CN113620973B (en) * | 2021-07-16 | 2024-05-07 | 西北工业大学 | Thermal activation delay fluorescent material and preparation method and application thereof |
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| WO2020211181A1 (en) | 2020-10-22 |
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