CN102703059A - Phosphorescent luminescent materials and preparation method and application thereof - Google Patents
Phosphorescent luminescent materials and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses phosphorescent luminescent materials and a preparation method and application thereof. The invention is characterized in that the phosphorescent luminescent materials are red light materials containing a metal iridium complex; a structural general formula of the phosphorescent luminescent materials is shown in the specification; and in the structural general formula, R1 and R2 are independently one of alkyl, phenyl, halogen-substituted phenyl, alkyl-substituted phenyl, naphthyl, anthryl, a halogen substituent, methoxy, phenoxy, cyano-substituted carbazolyl, substituted N-phenylcarbazolyl, quinolyl, thiazolyl, thienyl, an aromatic amino group, a group with an azole structure, an aromatic heterocyclic radical, a substituted aromatic heterocyclic radical and a silicon alkyl substituent respectively. The phosphorescent materials have high luminous efficiency; and the high luminous efficiency shows that the compounds can be taken as luminescent materials or main luminescent materials and applied to electroluminescent devices. Through data test and comparison, the materials are organic electroluminescent materials which have excellent performance and a good prospect, and particularly are phosphorescent red light materials which have good performance; and moreover, a method for synthesizing the luminescent materials is simple and low in cost.
Description
Technical field
the present invention relates to the organic photoelectrical material field; Relate in particular to the phosphorescent organic electroluminescent material; The electroluminescent material that contains novel organo-metallic complex of iridium; The compound method that comprises this series compound simultaneously comprises luminescent device and the corresponding electronic device of using this analog derivative.
Background technology
Exploitation to OLED (organic electroluminescence device) in
world wide has obtained very huge development; But along with the progress of application and development, also increasingly high to the requirement of material, more particularly can improve the luminous organic material of usefulness; Because synthetic technology is relatively more difficult now; Purification difficult, the building-up process of some compound possibly also relate to the more virose raw material or the course of processing, makes OLED aspect industrialized development, make slow progress.
organic electroluminescent technology is the latest generation flat panel display, can be used for flat-panel monitor and lighting source, and present commercial flat-panel monitor puts goods on the market.Lighting source since himself absolute predominance also very soon with industrialization.Electroluminescent device has structure of whole solid state, and electroluminescent organic material is core and the basis that constitutes this device.The exploitation of novel material is to promote the continuous progressive driving source of electroluminescent technology.To original material prepn and device optimization also is the research focus of present organic electroluminescent industry.
phosphorescence luminescence phenomenon is since finding; To receive everybody chasing after high always; Because the luminous efficiency of phosphor material is apparently higher than fluorescence radiation efficient; Can reach 100% luminous efficiency theoretically, so a lot of scientific research institution attempts to accelerate industrialized development through phosphor material all in the R&D intensity that strengthens phosphor material.But because the synthetic price comparison of phosphor material is high, synthesis technique requires than higher, and purifying requires than higher, and the life-span is very low, and efficient do not reach the height of anticipation, so also do not reach market-oriented demand fully.
We have synthesized the red light material of simple metal iridium complex through design
, improve experiment condition, and the compound method of organic phosphorescent material is simplified, and purify easily, and the industrialization synthetic yield significantly improves, and cost significantly reduces simultaneously.This series metal complex of iridium is as photovaltaic material; Fluorescent material and phosphor material that luminous efficiency is similar relatively all are significantly improved; Simultaneously the life-span of material is greatly improved, luminous more than ruddiness 620nm luminous peak position, be more satisfactory ruddiness phosphorescence luminous organic material.Through adjusting to substituted radical, make the performance of material reach the demand of industrialization more, can realize the adjusting of the usefulness aspect of material; All be significantly improved aspect film forming properties, life-span; Of many uses, can have a extensive future as in the multiple material of device.
Summary of the invention
the objective of the invention is to design and develop a kind of novel organic phosphorescent material, are the red light-emitting materials that contains metal iridium complex, and luminous peak position is more than 620nm; The present invention also provides the easy synthetic route that a cover cost is lower, can adapt to extensive industrialization needs simultaneously, and the application of this luminescent material in organic electroluminescence device, and has provided the corresponding devices structure.
For realizing above-mentioned purpose, the present invention provides a kind of organic phosphorescent light-emitting materials, it is characterized in that: this organic phosphorescent light-emitting materials is the red light material that contains metal iridium complex, and its general structure is suc as formula shown in (1):
（1）；
wherein, R1, R2 independently be respectively a kind of in alkyl, phenyl, halogen substituted phenyl, alkyl-substituted phenyl, naphthyl, anthryl, halogenic substituent, methoxyl group, phenoxy, cyanic acid, substituted carbazole base, replacement N-phenyl carbazole base, quinolyl, thiazolyl, thienyl, fragrant amido, azoles building stone, aromatic heterocyclic radical, substituted aromatic heterocyclic radical, the siloyl group substituting group.
The specific examples of the phosphor material that contains metal iridium complex of
formula of the present invention (1) expression is as follows, but is not limited to these given compounds of following instance.
The present invention also provides the synthetic route of the above-mentioned metal iridium complex of having optimized, and has provided the preparation method, and its concrete steps are:
Synthesizing of step 1, bridge ligand:
Under nitrogen protection system, take by weighing part 22mmol, IrCl33H2O 10mmol puts into reaction system, adds the mixing solutions of 300ml ethylene glycol ethyl ether and 100ml pure water; Nitrogen protection refluxed 24 hours, cool to room temperature has deposition to separate out then; To precipitate suction filtration, water flushing, oven dry; Make washing composition with methylene dichloride, use silica gel column chromatography, concentrate and separate out solid, obtain bridge ligand;
Synthesizing of step 2, metal iridium complex:
take by weighing bridge ligand 4mmol, add soda ash light 4.5g, add ethylene glycol ethyl ether 200ml in the system, add methyl ethyl diketone 16mmol, and under the nitrogen protection, backflow 10-15 hour, cool to room temperature had solid precipitation to separate out; Suction filtration, washing, oven dry; Make solvent with methylene dichloride, use silica gel column chromatography, the filtrating thickened solid is separated out, and obtains final garnet product.
organic phosphorescent material of the present invention has high luminous efficiency, and high luminous efficiency shows that this compound can be used as luminescent material or luminous material of main part, is applied in the electroluminescent device.Through data test and comparison; Find that this type material is the electroluminescent organic material of excellent property, particularly the red light material of the reasonable phosphorescence of performance is very promising one type of electroluminescent organic material; And the compound method of this luminescent material is simple, and cost is low.
Description of drawings
Fig. 1 is the nuclear magnetic spectrum of compd A 103;
Fig. 2 is the uv-absorbing and the fluorescent emission collection of illustrative plates of compd A 103.
Embodiment
Synthesizing of embodiment 1 compd A 101
Synthesizing of step 1, bridge ligand:
take by weighing part 22mmol (5.13g) under nitrogen protection system, IrCl33H2O 10mmol (3.52g) puts into reaction system, add the mixing solutions of 300ml ethylene glycol ethyl ether and 100ml pure water; Nitrogen protection refluxed 24 hours, cool to room temperature has deposition to separate out then, will precipitate suction filtration; The water flushing, oven dry is made washing composition with methylene dichloride, uses silica gel column chromatography; Concentrate and separate out solid, obtain bridge ligand 4.2g, productive rate is 92%.
Synthesizing of step 2, metal iridium complex (A101):
take by weighing bridge ligand 4mmol (3.67g), add soda ash light 4.5g, add ethylene glycol ethyl ether 200ml in the system; Add methyl ethyl diketone 16mmol (1.6g), under the nitrogen protection, refluxed 10 hours; Cool to room temperature has solid precipitation to separate out.Suction filtration, washing, oven dry; Make solvent with methylene dichloride, use silica gel column chromatography, the filtrating thickened solid is separated out, and obtains final garnet product 3.56g.Productive rate is 85%.HPLC purity is greater than 98%.
mass spectrum: calculated value is 524.12; Test value is 524.10.Ultimate analysis: calculated value C:50.46%; H:4.04%; N:2.67%; O:6.11%; Ir:36.71%; Test value is: C:50.43%; H:4.01%; N:2.65%; O:6.09%; Ir:36.68%.
Synthesizing of embodiment 2 compd As 103
Synthesizing of step 1, bridge ligand:
take by weighing part 22mmol (6.49g) under nitrogen protection system, IrCl33H2O 10mmol (3.52g) puts into reaction system; The mixing solutions that adds 300ml ethylene glycol ethyl ether and 100ml pure water, nitrogen protection refluxed 24 hours, cool to room temperature then; There is deposition to separate out; To precipitate suction filtration, water flushing, oven dry.Make washing composition with methylene dichloride, use silica gel column chromatography, concentrate and separate out solid, obtain bridge ligand 4.69g.Productive rate is 90%.
Synthesizing of step 2, metal iridium complex (A103):
take by weighing bridge ligand 4mmol (4.17g), add soda ash light 4.5g, add ethylene glycol ethyl ether 200ml in the system; Add methyl ethyl diketone 16mmol (1.6g), under the nitrogen protection, refluxed 15 hours; Cool to room temperature has solid precipitation to separate out.Suction filtration, washing, oven dry.Make solvent with methylene dichloride, use silica gel column chromatography, the filtrating thickened solid is separated out, and obtains final garnet product 3.99g, and luminous peak position is seen Fig. 2 more than 620nm.Productive rate is 85%.HPLC purity is greater than 98%.
mass spectrum: calculated value is 586.14; Test value is 586.11.Ultimate analysis: calculated value C:55.37%; H:3.96%; N:2.39%; O:5.46%; Ir:32.82%; Test value is: C:55.35%; H:3.94%; N:2.36%; O:5.45%; Ir:32.80%.See Fig. 1.
Synthesizing of embodiment 3 compd As 109
Synthesizing of step 1, bridge ligand:
take by weighing part 22mmol (6.62g) under nitrogen protection system, IrCl33H2O 10mmol (3.52g) puts into reaction system; The mixing solutions that adds 300ml ethylene glycol ethyl ether and 100ml pure water, nitrogen protection refluxed 24 hours, cool to room temperature then; There is deposition to separate out; To precipitate suction filtration, water flushing, oven dry.Make washing composition with methylene dichloride, use silica gel column chromatography, concentrate and separate out solid, obtain bridge ligand 4.91g.Productive rate is 93%.
Synthesizing of step 2, metal iridium complex (A109):
take by weighing bridge ligand 4mmol (4.22g), add soda ash light 4.5g, add ethylene glycol ethyl ether 200ml in the system; Add methyl ethyl diketone 16mmol (1.6g), under the nitrogen protection, refluxed 12 hours; Cool to room temperature has solid precipitation to separate out.Suction filtration, washing, oven dry.Make solvent with methylene dichloride, use silica gel column chromatography, the filtrating thickened solid is separated out, and obtains final garnet product 4.17g.Productive rate is 88%.HPLC purity is greater than 98%.
mass spectrum: calculated value is 592.09; Test value is 592.06.Ultimate analysis: calculated value C:50.74%; H:3.58%; N:2.37%; O:5.41%; S:5.42%; Ir:32.48%; Test value is: C:50.71%; H:3.56%; N:2.35%; O:5.38%; S:5.40%; Ir:32.46%.
Synthesizing of embodiment 4 compd As 113
Synthesizing of step 1, bridge ligand:
take by weighing part 22mmol (12.08g) under nitrogen protection system, IrCl33H2O 10mmol (3.52g) puts into reaction system; The mixing solutions that adds 300ml ethylene glycol ethyl ether and 100ml pure water, nitrogen protection refluxed 24 hours, cool to room temperature then; There is deposition to separate out; To precipitate suction filtration, water flushing, oven dry.Make washing composition with methylene dichloride, use silica gel column chromatography, concentrate and separate out solid, obtain bridge ligand 7.14g.Productive rate is 92%.
Synthesizing of step 2, metal iridium complex (A113):
take by weighing bridge ligand 4mmol (6.2g), add soda ash light 4.5g, add ethylene glycol ethyl ether 200ml in the system; Add methyl ethyl diketone 16mmol (1.6g), under the nitrogen protection, refluxed 15 hours; Cool to room temperature has solid precipitation to separate out.Suction filtration, washing, oven dry.Make solvent with methylene dichloride, use silica gel column chromatography, the filtrating thickened solid is separated out, and obtains final garnet product 5.51g.Productive rate is 82%.HPLC purity is greater than 98%.
mass spectrum: calculated value is 840.22; Test value is 840.19.Ultimate analysis: calculated value C:64.34%; H:3.96%; N:5.00%; O:3.81%; Ir:22.88%; Test value is: C:64.31%; H:3.94%; N:4.98%; O:3.78%; Ir:22.86%.
Synthesizing of embodiment 5 compd As 115
Synthesizing of step 1, bridge ligand:
take by weighing part 22mmol (7.77g) under nitrogen protection system, IrCl33H2O 10mmol (3.52g) puts into reaction system; The mixing solutions that adds 300ml ethylene glycol ethyl ether and 100ml pure water, nitrogen protection refluxed 24 hours, cool to room temperature then; There is deposition to separate out; To precipitate suction filtration, water flushing, oven dry.Make washing composition with methylene dichloride, use silica gel column chromatography, concentrate and separate out solid, obtain bridge ligand 5.22g.Productive rate is 90%.
Synthesizing of step 2, metal iridium complex (A115):
take by weighing bridge ligand 4mmol (4.64g), add soda ash light 4.5g, add ethylene glycol ethyl ether 200ml in the system; Add methyl ethyl diketone 16mmol (1.6g), under the nitrogen protection, refluxed 13 hours; Cool to room temperature has solid precipitation to separate out.Suction filtration, washing, oven dry.Make solvent with methylene dichloride, use silica gel column chromatography, the filtrating thickened solid is separated out, and obtains final garnet product 4.38g.Productive rate is 85%.HPLC purity is greater than 98%.
mass spectrum: calculated value is 644.16; Test value is 644.14.Ultimate analysis: calculated value C:54.10%; H:4.54%; N:2.18%; O:4.97%; Ir:29.85%; Test value is: C:54.08%; H:4.51%; N:2.16%; O:4.95%; Ir:29.82%.
can find out that from the data of table 1 organic phosphorescent material among the embodiment has high luminous efficiency, and high luminous efficiency shows that this compound can be used as luminescent material or luminous material of main part, is applied in the electroluminescent device.Simultaneously according to application example 6-10; We are applied to material in the organic electroluminescence device; Through data test and comparison; We find that really this type material is the electroluminescent organic material of excellent property, and particularly the red light material of the reasonable phosphorescence of performance is very promising one type of electroluminescent organic material.
Application implementation example 1
are placed on ultrasonic middle the cleaning 30 minutes of washings with its ito glass substrate that is formed with 1000 thickness in the above, use the zero(ppm) water ultrasonic cleaning then 10 minutes twice.After distilled water wash finishes, use Virahol respectively, toluene, acetone, ethanol difference ultrasonic cleaning 30 minutes, dry then.Put into the plasma washing machine at last,, send into vacuum evaporation equipment and process with oxygen plasma cleaning base plate 5 minutes.
With NPB, TCTA, synthetic materials, AlQ, LiF, Al vapor deposition respectively form the object construction device to device:
velocity of evaporation is that organism is 1/s, and the velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
test results of devices is cut-in voltage 5v, and high-high brightness is 2800cd/m2, and observing efficient under the 10v voltage is 25lm/w, and chromaticity coordinates (CIE) value is x:0.48; Y:0.26 obtains an orange red device, and life-span transformation period of device is 1000h.
Application implementation example 2
Application implementation example 2 is identical with making method with the device architecture of application implementation example 1, and different is to use the material of synthetic implementation method A103 as luminous dopant material, and the device architecture of making is:
velocity of evaporation is that organism is 1/s, and the velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
test results of devices is cut-in voltage 8.0v, and high-high brightness is 1800cd/m2, and observing efficient under the 10v voltage is 22lm/w, and chromaticity coordinates (CIE) value is x:0.46; Y:0.22 obtains an orange red device, and life-span transformation period of device is 1400h.
Application implementation example 3
Application implementation example 3 is identical with making method with the device architecture of application implementation example 1, and different is to use the material of synthetic implementation method A109 as luminescent material, and the device architecture of making is:
velocity of evaporation is that organism is 1/s, and the velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
test results of devices is cut-in voltage 6.0v, and high-high brightness is 1600cd/m2, and observing efficient under the 10v voltage is 18lm/w, and chromaticity coordinates (CIE) value is x:0.46; Y:0.25 obtains an orange red device, and life-span transformation period of device is 1380h.
Application implementation example 4
Application implementation example 4 is identical with making method with the device architecture of application implementation example 1, and different is to use the material of synthetic implementation method A113 as luminescent material, and the device architecture of making is:
velocity of evaporation is that organism is 1/s, and the velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
test results of devices is cut-in voltage 4.8v, and high-high brightness is 2300cd/m2, and observing efficient under the 10v voltage is 22lm/w, and chromaticity coordinates (CIE) value is x:0.43; Y:0.26 obtains an orange red device, and life-span transformation period of device is 1520h.
Application implementation example 5
Application implementation example 5 is identical with making method with the device architecture of application implementation example 1, and different is to use the material of synthetic implementation method A115 as luminescent material, and the device architecture of making is:
velocity of evaporation is that organism is 1/s, and the velocity of evaporation of LiF is 0.5/s, and the velocity of evaporation of Al is 2/s, and vacuum tightness remains the vacuum tightness below the 10-5pa normal atmosphere.
test results of devices is cut-in voltage 5.8v, and high-high brightness is 2200cd/m2, and observing efficient under the 10v voltage is 22lm/w, and chromaticity coordinates (CIE) value is x:0.44; Y:0.28 obtains an orange red device, and life-span transformation period of device is 1650h.
Claims (7)
1. organic phosphorescent light-emitting materials, it is characterized in that: this organic phosphorescent light-emitting materials is the red light material that contains metal iridium complex, its general structure is suc as formula shown in (1):
Wherein, R1, R2 independently be respectively a kind of in alkyl, phenyl, halogen substituted phenyl, alkyl-substituted phenyl, naphthyl, anthryl, halogenic substituent, methoxyl group, phenoxy, cyanic acid, substituted carbazole base, replacement N-phenyl carbazole base, quinolyl, thiazolyl, thienyl, fragrant amido, azoles building stone, aromatic heterocyclic radical, substituted aromatic heterocyclic radical, the siloyl group substituting group.
2. organic phosphorescent light-emitting materials according to claim 1 is characterized in that: organic phosphorescent light-emitting materials is any one in the represented compound of structural formula A101-A130:
。
3. organic phosphorescent light-emitting materials according to claim 2 is characterized in that: organic phosphorescent light-emitting materials be among structural formula A101, A103, A109, A113, the A115 any one:
。
4. according to the preparation method of claim 1,2 or 3 described organic phosphorescent light-emitting materials, it is characterized in that:
Synthesizing of step 1, bridge ligand:
Under nitrogen protection system, take by weighing part 22mmol, IrCl33H2O 10mmol puts into reaction system, adds the mixing solutions of 300ml ethylene glycol ethyl ether and 100ml pure water; Nitrogen protection refluxed 24 hours, cool to room temperature has deposition to separate out then; To precipitate suction filtration, water flushing, oven dry; Make washing composition with methylene dichloride, use silica gel column chromatography, concentrate and separate out solid, obtain bridge ligand;
Synthesizing of step 2, metal iridium complex:
Take by weighing bridge ligand 4mmol, add soda ash light 4.5g, add ethylene glycol ethyl ether 200ml in the system, add methyl ethyl diketone 16mmol, under the nitrogen protection, backflow 10-15 hour, cool to room temperature had solid precipitation to separate out; Suction filtration, washing, oven dry; Make solvent with methylene dichloride, use silica gel column chromatography, the filtrating thickened solid is separated out, and obtains final garnet product.
5. the application of organic phosphorescent light-emitting materials according to claim 1 is characterized in that: between the positive and negative electrode on the organic electronic devices, have at least one deck organic material layer to comprise any one compound according to claim 1.
6. the application of organic phosphorescent light-emitting materials according to claim 5 is characterized in that: organic electronic devices comprises organic luminescent device, solar cell device, organic semiconductor device, organic crystal tube device.
7. the application of organic phosphorescent light-emitting materials according to claim 5; It is characterized in that: organic material layer comprises luminescent material, hole mobile material, electron transport material, hole-injecting material, electronics injecting material, hole barrier materials, electronics blocking material, and organic material layer comprises the described organic materials of one or more claims 1.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1589307A (en) * | 2001-10-17 | 2005-03-02 | 通用显示公司 | Phosphorescent compounds and devices comprising the same |
-
2012
- 2012-05-31 CN CN2012101746852A patent/CN102703059A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1589307A (en) * | 2001-10-17 | 2005-03-02 | 通用显示公司 | Phosphorescent compounds and devices comprising the same |
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| KR102603350B1 (en) * | 2014-11-18 | 2023-11-21 | 롬엔드하스전자재료코리아유한회사 | A plurality of dopant materials and organic electroluminescent device comprising the same |
| KR20160059437A (en) * | 2014-11-18 | 2016-05-26 | 롬엔드하스전자재료코리아유한회사 | A plurality of dopant materials and organic electroluminescent device comprising the same |
| US10153441B2 (en) | 2015-03-30 | 2018-12-11 | Industrial Technology Research Institute | Organic metal compound, organic light-emitting device, and lighting device employing the same |
| US10847728B2 (en) | 2015-10-01 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11889747B2 (en) | 2015-10-01 | 2024-01-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN105368446B (en) * | 2015-12-19 | 2018-06-29 | 江西冠能光电材料有限公司 | The organic electroluminescence device of electroluminescent material and its preparation containing furans |
| CN105368446A (en) * | 2015-12-19 | 2016-03-02 | 江西冠能光电材料有限公司 | Furan-containing electroluminescent material and organic electroluminescent device made of furan-containing electroluminescent material |
| EP3323822A1 (en) * | 2016-09-23 | 2018-05-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN113563385A (en) * | 2016-09-23 | 2021-10-29 | 环球展览公司 | Organic electroluminescent material and device |
| CN107868109A (en) * | 2016-09-23 | 2018-04-03 | 环球展览公司 | Electroluminescent organic material and device |
| CN107868109B (en) * | 2016-09-23 | 2021-07-27 | 环球展览公司 | Organic electroluminescent material and device |
| JP2018058797A (en) * | 2016-10-06 | 2018-04-12 | 三菱ケミカル株式会社 | Iridium complex compound, and composition, organic electroluminescent element, display device, and illumination device containing the compound |
| CN107459535A (en) * | 2017-09-21 | 2017-12-12 | 南京工业大学 | The iridium of poly-substituted quinoline coordination is miscellaneous with compound and preparation method and application |
| WO2019056515A1 (en) * | 2017-09-21 | 2019-03-28 | 南京工业大学 | Multi-substituted quinoline-coordinated iridium-hybridized compound, preparation method therefor and application thereof |
| US11685756B2 (en) | 2017-11-07 | 2023-06-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11214587B2 (en) * | 2017-11-07 | 2022-01-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN109956977A (en) * | 2017-12-25 | 2019-07-02 | 北京夏禾科技有限公司 | The metal complex of the ligand containing heterocyclic substituted, and electroluminescent device and compound formulas comprising the complex compound |
| CN108997438A (en) * | 2018-08-06 | 2018-12-14 | 浙江华显光电科技有限公司 | Red phosphorescent compound and the organic light emitting diode device for using the compound |
| CN108997438B (en) * | 2018-08-06 | 2023-10-27 | 浙江华显光电科技有限公司 | Red phosphorescent compound and organic light emitting diode device using the same |
| CN108997384A (en) * | 2018-08-28 | 2018-12-14 | 清华大学 | Luminous cluster compound of a kind of loop coil silver cluster and the preparation method and application thereof |
| CN112552351A (en) * | 2019-09-26 | 2021-03-26 | 环球展览公司 | Organic electroluminescent material and device |
| US11999886B2 (en) | 2019-09-26 | 2024-06-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN113321685A (en) * | 2020-02-28 | 2021-08-31 | 北京夏禾科技有限公司 | Metal complex, organic electroluminescent material and application thereof |
| CN113201028A (en) * | 2021-05-24 | 2021-08-03 | 南京邮电大学 | Methoxy-regulation-based broadband yellow phosphorescent 2-phenylquinoline iridium (III) complex and preparation method and application thereof |
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