CN107151258A - A kind of organic compound and OLED display - Google Patents
A kind of organic compound and OLED display Download PDFInfo
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- CN107151258A CN107151258A CN201610120824.1A CN201610120824A CN107151258A CN 107151258 A CN107151258 A CN 107151258A CN 201610120824 A CN201610120824 A CN 201610120824A CN 107151258 A CN107151258 A CN 107151258A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 39
- 239000000463 material Substances 0.000 claims abstract description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- -1 heterocycle alkane Chemical class 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 4
- 150000001924 cycloalkanes Chemical class 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 6
- 150000002390 heteroarenes Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- 229940093475 2-ethoxyethanol Drugs 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 0 Cc1c(*)cccc1-c1c(C)c(*)ccn1 Chemical compound Cc1c(*)cccc1-c1c(C)c(*)ccn1 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910021640 Iridium dichloride Inorganic materials 0.000 description 3
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000001698 laser desorption ionisation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 229910006400 μ-Cl Inorganic materials 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- UYNIDMQQWYSTRJ-UHFFFAOYSA-N C1=CC2=Nc(ccc3ccc4)cc3c4C3=NC=C[C]1C3=C2 Chemical compound C1=CC2=Nc(ccc3ccc4)cc3c4C3=NC=C[C]1C3=C2 UYNIDMQQWYSTRJ-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a kind of organic compound as electroluminescent organic material, its structure is as shown in formula：Wherein, A and B are independently selected from five yuan or hexa-atomic cycloalkane or aromatic hydrocarbons, or contain one or more heteroatomic five yuan or hexa-member heterocycle alkane or heteroaryl hydrocarbon；X is selected from CR1R2、COR3、NR4、SiR5R6Or GeR7R8；R1-R8It is independently selected from hydrogen, deuterium, halogen, alkyl group, substituted or unsubstituted cycloalkyl, substituted or unsubstituted Heterocyclylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.The organic compound is mainly used in the luminescent layer of OLED display, it is preferable that applied in feux rouges guest materials, the beneficial effect such as obtained OLED display has low long lifespan, driving voltage, chemical stability and heat endurance is good.
Description
Technical Field
The present invention relates to a metal complex, and more particularly, to an organic compound used as an organic electroluminescent material, and an OLED display device including the same.
Background
The TFT-LCD is a non-self-luminous display, which must transmit the light projected from the backlight source, sequentially penetrate the related components of the TFT-LCD panel, such as the polarizer, the glass substrate, the liquid crystal layer, the color filter, the glass substrate, the polarizer, and finally enter the eyes of the person for imaging, so as to achieve the display function. In practical application, the TFT-LCD display has the disadvantages of slow response rate, power consumption, narrow viewing angle, etc., and is not enough to become a perfect display.
The organic electroluminescence refers to a phenomenon that a thin film device prepared from an organic photoelectric functional material emits light under the excitation action of an electric field, is known as the most potential next-generation flat panel display technology by the industry and academia, and has the advantages of low power consumption, wide viewing angle, fast response, lightness, thinness, flexible display and the like. The organic electroluminescent device, also called an Organic Light Emitting Diode (OLED), is composed of a transparent anode ITO, a metal cathode, and an organic thin film layer. Under the drive of direct current voltage, electrons injected from the cathode and holes injected from the anode move to the organic light-emitting layer, and finally meet in the light-emitting layer and are recombined to emit light. Organic semiconductor diodes have more complicated physical processes of carriers due to disorder of their structures and diversity of materials than inorganic semiconductor diodes, and organic materials for electron transport layers and hole blocking layers are important.
The organic electroluminescent material is used as a core component of an organic electroluminescent device, and has great influence on the service performance of the device. Among them, fluorescence characteristics with high quantum efficiency, good semiconductor characteristics, high-quality film formation characteristics, good chemical and thermal stability, good processability, and the like are main performance factors. The organic light-emitting material is classified by the light-emitting wavelength range according to the molecular structural characteristics, and includes small molecule organic compounds, organic complex light-emitting materials, and organic polymer materials.
CN104650040A discloses an organic electroluminescent compound of phenazine derivatives, the structural formula of which is:wherein the organic electroluminescent compound is used in at least one or more of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer or an electron transport layer, and has the advantages of good electroluminescent efficiency, excellent color purity and long service life; CN104744369A discloses aAn organic electroluminescent material having the structural formulaA derivative of (a); the derivative forms a substance of a spiro-like compound due to the introduction of 2 benzene rings, increases the plane conjugation of a molecular structure, improves the solubility of the organic electroluminescent material, and enables the organic electroluminescent material to be easier to prepare.
At present, with the continuous expansion of the application range of organic electroluminescent devices, those skilled in the art are also going to deeply research the organic electroluminescent materials, and nevertheless, the luminescent materials still have many defects in the practical application process, so that designing and synthesizing a novel organic electroluminescent material to overcome the defects in the current practical application process is the key point in the research work of OLEDs.
Disclosure of Invention
Based on the above background, the present invention provides an organic compound used as an organic electroluminescent material, which is mainly applied to a light emitting layer of an OLED display device, preferably, a red guest material, and the resulting display device has the beneficial effects of long lifetime, low driving voltage, good chemical stability and thermal stability, etc.
The technical scheme of the invention comprises an organic compound used as an organic electroluminescent material, which is characterized in that the structure is shown as a general formula (I):
wherein A and B are independently selected from five-membered or six-membered cycloalkane or arene, or five-membered or six-membered heterocycloalkane or heteroarene containing one or more heteroatoms;
x is selected from CR1R2、COR3、NR4、SiR5R6Or GeR7R8；
R1-R8Independently of one another, from the group consisting of hydrogen, deuterium, halogen, alkanyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;
m is a metal having an atomic weight greater than 40;
y is an auxiliary ligand;
m is the total coordination number of metal M and n is an integer less than M and at least 1.
In one embodiment of the present invention, said M is Ir.
In another embodiment, Y has the structure
Further, in one embodiment, n is 2.
In one embodiment of the invention, a and B are selected from no more than two and no more than two heteroatoms in each heterocycle, said heteroatoms being selected from O, S or N, preferably N.
Further, A and B are independently selected from a five-or six-membered aromatic hydrocarbon, or a five-or six-membered heteroaromatic hydrocarbon containing one or more heteroatoms.
In one embodiment, R1-R8Independently of one another, from the group consisting of hydrogen, alkanyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; wherein, the substitution can be mono, di, tri, tetra, penta substitution, and the substitution is preferably alkanyl, such as methyl and ethyl; the hetero atom in the heteroaryl group is preferablyIs N.
In a preferred embodiment of the present invention, the organic compound has the following structure:
the technical scheme of the invention also comprises a preparation method of the organic compound, taking the structural formula shown in the general formula (II) as an example, and the preparation route comprises the following steps:
the technical scheme of the invention also comprises an organic electroluminescent material containing the organic compound.
The technical scheme of the invention also comprises an OLED light-emitting layer containing the organic compound.
The technical scheme of the invention also comprises an OLED red light guest material containing the organic compound.
The invention also provides an OLED display device containing the organic compound.
The organic compound provided by the invention is mainly applied to a light emitting layer of an OLED device, preferably applied to a red light object material, has important application value for researching the development and application of the red light material, and the OLED device prepared by the organic compound provided by the invention has the advantages of low driving voltage, higher current density, higher power efficiency and brightness, solves the defects of slow reaction rate, power consumption, narrow visual angle and the like of the existing display screen, and has the beneficial effects of long service life, low driving voltage, good chemical stability and thermal stability and the like.
Detailed Description
The invention provides an organic compound used as an organic electroluminescent material, which is characterized in that the structure is shown as the general formula (I):
wherein A and B are independently selected from five-membered or six-membered cycloalkane or arene, or five-membered or six-membered heterocycloalkane or heteroarene containing one or more heteroatoms;
x is selected from CR1R2、COR3、NR4、SiR5R6Or GeR7R8；
R1-R8Independently of one another, from the group consisting of hydrogen, deuterium, halogen, alkanyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;
m is a metal having an atomic weight greater than 40;
y is an auxiliary ligand;
m is the total coordination number of metal M and n is an integer less than M and at least 1.
In one embodiment of the present invention, said M is Ir.
In another embodiment, Y has the structure
Further, in one embodiment, n is 2.
In one embodiment of the invention, a and B are selected from no more than two and no more than two heteroatoms in each heterocycle, said heteroatoms being selected from O, S or N, preferably N.
Further, A and B are independently selected from a five-or six-membered aromatic hydrocarbon, or a five-or six-membered heteroaromatic hydrocarbon containing one or more heteroatoms.
In one embodiment, R1-R8Independently of one another, from the group consisting of hydrogen, alkanyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; wherein, the substitution can be mono, di, tri, tetra, penta substitution, and the substitution is preferably alkanyl, such as methyl and ethyl; the heteroatom in the heteroaryl group is preferably N.
In a preferred embodiment of the present invention, the organic compound has the following structure:
the invention also provides a preparation method of the organic compound, taking the structural formula shown in the general formula (II) as an example, the preparation route comprises the following steps:
the invention also provides an organic electroluminescent material containing the organic compound.
The invention also provides an OLED light-emitting layer containing the organic compound.
The invention also provides an OLED red light guest material containing the organic compound.
The invention also provides an OLED display device containing the organic compound.
According to the above technical solution of the present invention, the contents of the present invention will be further explained and explained by the following specific examples and application examples.
Example 1
An organic compound having a structure represented by general formula (1) and useful as an organic electroluminescent material, particularly as a red guest material:
the synthesis method comprises the following steps:
(1) preparation of ligand L1
Compounds A1(7.8mmol) and B (7.8mmol) were weighed out in 30ml absolute ethanol and 1ml saturated NaOH in ethanol was added. The mixture was heated to reflux and reacted overnight. And (3) cooling to room temperature after the reaction is completed, and purifying by rotary evaporation and column chromatography to obtain a solid product L1.
(2) Preparation of Complex 1
Weighing IrCl3·3H2O (1mmol) and L1(2.5mmol) were added to a three-necked flask, and the reaction system was protected with nitrogen by three cycles of evacuation-nitrogen-evacuation on the double drain tube. Injecting a mixture (3:1, v/v) of 2-ethoxyethanol and water into a reaction system by using an injector, stirring, heating the reaction system to 110 ℃, and reacting for about 24 hours, wherein a precipitate is generated in the reaction process. The reaction was cooled to room temperature, and then the precipitate was filtered and washed with water and ethanol to give a red solid product, i.e., an iridium dichlorobridge compound (L1)2Ir(μ-Cl)2Ir(L1)2。
Iridium dichloride bridge compound (0.2mmol) and Na are weighed2CO3(1.4mmol) and added into a three-neck flask, and the reaction system is recycled for three times by vacuumizing-charging nitrogen-vacuumizing on a double-row pipe, and finally protected by nitrogen. Acetylacetone (0.5mmol) and 2-ethoxyethanol were injected into the reaction system with a syringe, respectively, stirred, and the reaction system was heated to reflux. After the reaction is carried out for 12 hours, the reaction mixture is cooled to room temperature, red precipitate is obtained by filtration, and the red solid complex 1 is obtained by column chromatography purification.
The structure of the iridium complex obtained was analyzed by laser desorption ionization time-of-flight MASS spectrometer (MALDI-TOF-MASS) and nuclear magnetic resonance hydrogen spectroscopy (1H NMR).
Molecular weight characterization MS 823.88
1H-NMR：(400MHz,CDCl3)，(ppm)：8.41(d,2H),8.02(d,2H),7.61-7.68(m,8H),7.43-7.46(m,4H),4.62(s,1H),3.94(s,4H),1.51(s,6H).
Example 2
An organic compound having a structure represented by general formula (3) and useful as an organic electroluminescent material, particularly as a red guest material:
the synthesis method comprises the following steps:
(1) preparation of ligand L3
Compounds A3(7.8mmol) and B (7.8mmol) were weighed out in 30ml absolute ethanol and 1ml saturated NaOH in ethanol was added. The mixture was heated to reflux and reacted overnight. And (3) cooling to room temperature after the reaction is completed, and purifying by rotary evaporation and column chromatography to obtain a solid product L3.
(2) Preparation of Complex 3
Weighing IrCl3·3H2O (1mmol) and L3(2.5mmol) were added to a three-necked flask, and the reaction system was protected with nitrogen by three cycles of evacuation-nitrogen-evacuation on the double drain tube. Injecting a mixture (3:1, v/v) of 2-ethoxyethanol and water into a reaction system by using an injector, stirring, heating the reaction system to 110 ℃, and reacting for about 24 hours, wherein a precipitate is generated in the reaction process. The reaction was cooled to room temperature, and then the precipitate was filtered and washed with water and ethanol to give a red solid product, i.e., an iridium dichlorobridge compound (L3)2Ir(μ-Cl)2Ir(L3)2。
Iridium dichloride bridge compound (0.2mmol) and Na are weighed2CO3(1.4mmol) and added into a three-neck flask, and the reaction system is recycled for three times by vacuumizing-charging nitrogen-vacuumizing on a double-row pipe, and finally protected by nitrogen. Acetylacetone (0.5mmol) and 2-ethoxyethanol were injected into the reaction system with a syringe, respectively, stirred, and the reaction system was heated to reflux. After the reaction is carried out for 12 hours, the reaction mixture is cooled to room temperature, red precipitate is obtained by filtration, and the red solid complex 3 is obtained by column chromatography purification.
The structure of the iridium complex obtained was analyzed by laser desorption ionization time-of-flight MASS spectrometer (MALDI-TOF-MASS) and nuclear magnetic resonance hydrogen spectroscopy (1H NMR).
Molecular weight characterization MS 1161.23
1H-NMR：(400MHz,CDCl3)，(ppm)：8.44(d,2H),8.12(s,2H),8.07(d,2H),7.14(s,2H),7.81-7.85(m,4H),7.72(d,2H),7.60-7.68(m,4H),7.56(d,8H),7.44(m,2H),7.32(m,12H),7.12(d,2H),4.83(s,1H),1.63(s,6H).
Example 3
An organic compound having a structure represented by general formula (8) and useful as an organic electroluminescent material, particularly as a red guest material:
the synthesis method comprises the following steps:
(1) preparation of ligand L8
Compounds A8(7.8mmol) and B (7.8mmol) were weighed out in 30ml absolute ethanol and 1ml saturated NaOH in ethanol was added. The mixture was heated to reflux and reacted overnight. And (3) cooling to room temperature after the reaction is completed, and purifying by rotary evaporation and column chromatography to obtain a solid product L8.
(2) Preparation of Complex 8
Weighing IrCl3·3H2O (1mmol) and L8(2.5mmol) were added to a three-necked flask, evacuated on a double drain-nitrogen-evacuated, cycled three times, and finally purged with nitrogenAnd protecting the reaction system. Injecting a mixture (3:1, v/v) of 2-ethoxyethanol and water into a reaction system by using an injector, stirring, heating the reaction system to 110 ℃, and reacting for about 24 hours, wherein a precipitate is generated in the reaction process. The reaction was cooled to room temperature, and then the precipitate was filtered and washed with water and ethanol to give a red solid product, i.e., an iridium dichlorobridge compound (L8)2Ir(μ-Cl)2Ir(L8)2。
Iridium dichloride bridge compound (0.2mmol) and Na are weighed2CO3(1.4mmol) and added into a three-neck flask, and the reaction system is recycled for three times by vacuumizing-charging nitrogen-vacuumizing on a double-row pipe, and finally protected by nitrogen. Acetylacetone (0.5mmol) and 2-ethoxyethanol were injected into the reaction system with a syringe, respectively, stirred, and the reaction system was heated to reflux. After the reaction is carried out for 12 hours, the reaction mixture is cooled to room temperature, red precipitate is obtained by filtration, and the red solid complex 8 is obtained by column chromatography purification.
The structure of the iridium complex obtained was analyzed by laser desorption ionization time-of-flight MASS spectrometer (MALDI-TOF-MASS) and nuclear magnetic resonance hydrogen spectroscopy (1H NMR).
Molecular weight characterization MS 978.29
1H-NMR：(400MHz,CDCl3)，(ppm)：8.21(d,2H),7.99(d,2H),7.52-7.58(m,6H),7.20(m,2H),7.05(d,2H),6.99(m,4H),6.92(s,2H),6.75-6.78(m,4H),6.68(m,2H),6.44(d,4H),4.61(s,1H),1.45(s,6H).
Application examples
Comparative application example
The transparent anode electrode ITO substrate was ultrasonically cleaned in isopropanol for 5-10 minutes and exposed to uv light for 20-30 minutes, followed by plasma treatment for 5-10 minutes. And then putting the processed ITO substrate into evaporation equipment. Firstly, a layer of NPB with the thickness of 30-50nm is evaporated to be used as a hole transport layer, then the evaporation of a luminescent layer is carried out, the mixed evaporation of a compound CBP and 5-10% of Ir (piq)2(acac) is carried out, then 20-40nm of Alq3 is evaporated to be used as an electron transport layer, then 0.5-2nm of LiF is evaporated to be carried out, and then 100-200nm of metal Al is evaporated to be used.
Application example 1
The transparent anode electrode ITO substrate was ultrasonically cleaned in isopropanol for 5-10 minutes and exposed to uv light for 20-30 minutes, followed by plasma treatment for 5-10 minutes. And then putting the processed ITO substrate into evaporation equipment. Firstly, a layer of NPB with the thickness of 30-50nm is evaporated to be used as a hole transport layer, then the evaporation of a luminescent layer is carried out, the mixed evaporation of a compound CBP and 5-10% of a complex 1 is carried out, then 20-40nm of Alq3 is evaporated, then 0.5-2nm of LiF is evaporated, and then 100-200nm of metal Al is evaporated.
Application example 2
The complex Ir (piq)2(acac) in the comparative example was replaced by complex 3 as a guest of the light-emitting layer.
Application example 3
The complex Ir (piq)2(acac) in the comparative example was replaced by complex 8 as a guest of the light-emitting layer.
Wherein,
the OLED display device was made as follows:
comparative application example: ITO/NPB/CBP: ir (piq)2(acac)/Alq 3/LiF/Al;
application example 1: ITO/NPB/CBP: the complex is 1/Alq 3/LiF/Al;
application example 2: ITO/NPB/CBP: the complex is 3/Alq 3/LiF/Al;
application example 3: ITO/NPB/CBP: the complex is 8/Alq 3/LiF/Al.
At 1000nits, the OLED display results are as follows:
| application examples | Voltage/V | Cd/A | lm/W | CIEx | CIEy | LT90@1000nit |
| 1 | 4.8 | 17 | 13.1 | 0.673 | 0.330 | 118 |
| 2 | 4.9 | 18 | 14.6 | 0.670 | 0.325 | 123 |
| 3 | 5.0 | 18 | 14.8 | 0.671 | 0.328 | 137 |
| Comparative example | 5.3 | 14 | 10.3 | 0.670 | 0.330 | 108 |
From the above detection results, the average driving voltage of the OLED devices of examples 1 to 3 of the present invention is 4.9V, the average current density is 17.67A, and the average power efficiency is 14.17W, and compared with the OLED device of the present comparative example, the OLED devices prepared by using the organic compound of the present invention have low driving voltage, high current density, and greatly improved power efficiency and brightness, and the defects of slow reaction rate, power consumption, narrow viewing angle, etc. of the existing display screen are solved.
The embodiments of the present invention have been described in detail, but the embodiments are merely examples, and the present invention is not limited to the embodiments described above. Any equivalent modifications and substitutions to those skilled in the art are also within the scope of the present invention. Accordingly, equivalent changes and modifications made without departing from the spirit and scope of the present invention should be covered by the present invention.
Claims (10)
1. An organic compound having a formula represented by general formula (I):
wherein A and B are independently a five-membered or six-membered cycloalkane or arene, or a five-membered or six-membered heterocycloalkane or heteroarene containing one or more heteroatoms;
x is CR1R2、COR3、NR4、SiR5R6Or GeR7R8；
R1-R8Independently of one another, hydrogen, deuterium, halogen, alkanyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;
m is a metal having an atomic weight greater than 40;
y is an auxiliary ligand;
m is the total coordination number of the metal M, and n is an integer of 1 or more and less than M.
2. The organic compound of claim 1, wherein M is Ir; n is 2.
3. The organic compound of claim 3, wherein Y has the structure
4. An organic compound according to claim 1, wherein a and B are five or six membered heterocyclic alkanes or heteroarenes containing one or more heteroatoms, wherein the number of heteroatoms in each heterocycle is no more than two and the species is no more than two, and wherein the heteroatoms are selected from O, S or N.
5. An organic compound according to claim 1, wherein the substitution is mono-, di-, tri-, tetra-, penta-, and the substituent is alkanyl; the heteroatom in the heteroaryl group is N.
6. The organic compound of claim 1, wherein the structure of the organic compound is as follows:
7. a process for the preparation of the organic compound according to claim 3, wherein the route of preparation comprises:
8. the organic compound according to claim 1, wherein the organic compound is used for an OLED light emitting layer material.
9. The organic compound of claim 1, wherein the organic compound is used in an OLED red guest material.
10. An OLED display device comprising the organic compound according to claims 1 to 9.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1418217A1 (en) * | 2001-06-04 | 2004-05-12 | Sanyo Electric Co., Ltd. | Organo-electroluminescence element, luminescent material and organic compound |
| CN101087863A (en) * | 2004-12-23 | 2007-12-12 | 西巴特殊化学品控股有限公司 | Electroluminescent metal complexes with nucleophilic carbene ligands |
| CN103113413A (en) * | 2013-02-07 | 2013-05-22 | 合肥京东方光电科技有限公司 | Bicyclo-iridium complex, preparation method of complex, organic light emitting diode (OLED) and preparation method of OLED |
-
2016
- 2016-03-03 CN CN201610120824.1A patent/CN107151258A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1418217A1 (en) * | 2001-06-04 | 2004-05-12 | Sanyo Electric Co., Ltd. | Organo-electroluminescence element, luminescent material and organic compound |
| CN101087863A (en) * | 2004-12-23 | 2007-12-12 | 西巴特殊化学品控股有限公司 | Electroluminescent metal complexes with nucleophilic carbene ligands |
| CN103113413A (en) * | 2013-02-07 | 2013-05-22 | 合肥京东方光电科技有限公司 | Bicyclo-iridium complex, preparation method of complex, organic light emitting diode (OLED) and preparation method of OLED |
Non-Patent Citations (2)
| Title |
|---|
| CHENG-HSIEN YANG等，: "Color tuning of iridium complexes for organic light-emitting diodes:The electronegative effect and π-conjugation effect", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》 * |
| CHENG-HSIEN YANG等，: "Synthesis of a high-efficiency red phosphorescent emitter for organic light-emitting diodes", 《J. MATER. CHEM.》 * |
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