CN114874208B - Phenanthroline compound, organic electroluminescent device and display or lighting device - Google Patents
Phenanthroline compound, organic electroluminescent device and display or lighting device Download PDFInfo
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- CN114874208B CN114874208B CN202210417554.6A CN202210417554A CN114874208B CN 114874208 B CN114874208 B CN 114874208B CN 202210417554 A CN202210417554 A CN 202210417554A CN 114874208 B CN114874208 B CN 114874208B
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- organic electroluminescent
- light emitting
- electroluminescent device
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- -1 Phenanthroline compound Chemical class 0.000 title claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 103
- 239000012044 organic layer Substances 0.000 claims description 24
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 abstract description 22
- 239000000463 material Substances 0.000 abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 229910052805 deuterium Inorganic materials 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 150000001875 compounds Chemical class 0.000 description 55
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- 230000032258 transport Effects 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000126 substance 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
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- UJORPFQWUKFXIE-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4h-cyclopenta[c]pyrazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(CCC2)=C2C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 UJORPFQWUKFXIE-UHFFFAOYSA-N 0.000 description 1
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 1
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005550 pyrazinylene group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a phenanthroline compound, an organic electroluminescent device and a display or lighting device, wherein the charge generation and electron transport material at least comprises the phenanthroline compound, wherein the phenanthroline derivative is represented by the following formula 1: Wherein R 1 to R 8 are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C5-C30 heteroaryl; wherein at least one is a substituted or unsubstituted C7-C30 benzo [ d ] oxazolyl group. The organic electroluminescent device comprising the phenanthroline compound according to the present invention has a reduced driving voltage and improved efficiency compared to a comparative organic electroluminescent device.
Description
Technical Field
The invention relates to a phenanthroline compound, in particular to a phenanthroline compound, an organic electroluminescent device and a display or lighting device.
Background
The light emitting device is a device that converts electric energy into light energy using an organic substance, and includes a structure of an organic layer that may emit light between an anode and a cathode.
The organic light emitting device may be formed in various structures, in which a plurality of light emitting units are overlapped (tendem) is being studied.
In an overlap (tendem) organic electroluminescent device, a stack of light emitting cells comprising a light emitting layer between an anode and a cathode is provided.
A charge generation layer is provided between adjacent light emitting portions for generation and movement of charges.
The charge generation layer requires a low driving voltage and high efficiency.
Disclosure of Invention
The invention provides an organic electroluminescent device containing a phenanthroline compound, which minimizes the energy level difference between an n-type charge generation layer and a p-type charge generation layer, and improves the electron injection amount of a light emitting part, thereby reducing driving voltage and improving efficiency.
In order to achieve the purpose of the invention, the technical scheme of the invention is as follows:
The invention provides a phenanthroline compound, which has a structure shown in formula 1:
Wherein R 1 to R 8 are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C5-C30 heteroaryl; wherein at least one is a substituted or unsubstituted C7-C30 benzo [ d ] oxazole;
preferably, wherein the phenanthroline compound is represented by any one of the following formulas 1-1 to 1-4:
Wherein R 9～R17 is each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C5-C30 heteroaryl;
Each L 1～L6 is independently phenylene, pyridylene, pyrimidinylene, pyrazinylene, imidazolylene, biphenylene, or naphthylene;
n is 0 or 1.
Preferably, wherein R 1 to R 17 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted naphthyridinyl, or a combination thereof.
More preferably, wherein the phenanthroline compound is any one of the following:
the present invention further provides an organic electroluminescent device comprising:
a first electrode;
A second electrode; and
An organic layer between the first electrode and the second electrode;
the organic layer comprises the phenanthroline compound.
Preferably, at least one of the organic layers is a charge generation layer or an electron transport layer.
More preferably, the charge generation layer is an n-type charge generation layer.
More preferably, the n-type charge generation layer is composed of a metal or an organic material doped with n-type, wherein the metal is selected from Li, na, K, rb, cs, mg, ca, sr, ba, la, ce, sm, eu, tb, dy or Yb.
The present invention further provides an organic electroluminescent device comprising:
a first electrode;
A second electrode;
a first light emitting portion of a first light emitting layer, which is located between the first electrode and the second electrode;
A second light emitting portion of a second light emitting layer, which is located between the second electrode and the first light emitting portion; and
A first charge generation layer located between the first light emitting portion and the second light emitting portion;
At least one of the first light emitting part, the second light emitting part, or the first charge generating layer comprises the phenanthroline compound of the present invention.
The invention further provides application of the phenanthroline compound in manufacturing an organic electroluminescent device.
The invention also provides a display or lighting device comprising the organic electroluminescent device of the invention.
According to the present invention, in the case where the n-type charge generation layer is doped with an alkali metal, the alkali metal is strongly permeated into the main compound phenanthroline compound, and the diffusion phenomenon of the alkali metal into the p-type charge generation layer is minimized, thereby using the organic electroluminescent device.
Provides a phenanthroline compound capable of improving the service life and an organic electroluminescent device comprising the same.
Drawings
Fig. 1 is a structural layer diagram of an organic electroluminescent device of the present invention.
Detailed Description
Another object of the present invention is to provide a phenanthroline compound capable of increasing an electron injection amount for a light emitting part by minimizing an energy level difference between an n-type charge generation layer and a p-type charge generation layer, and an organic electroluminescent device including the same.
Another object of the present invention is to provide a phenanthroline compound that minimizes the phenomenon of alkali metal diffusion into a p-type charge generation layer even when an n-type charge generation layer is doped with an alkali metal, and an organic electroluminescent device including the same.
According to the organic electroluminescent device comprising the phenanthroline compound, the energy level difference between the n-type charge generation layer and the p-type charge generation layer is minimized, and the electron injection amount of the light emitting part is improved, thereby reducing the driving voltage and improving the efficiency.
According to the present invention, in the case where the n-type charge generation layer is doped with an alkali metal, the alkali metal is firmly permeated into the main compound phenanthroline compound, and the diffusion phenomenon of the alkali metal into the p-type charge generation layer is minimized, thereby improving the life span of the organic light emitting device.
Provides a phenanthroline compound capable of improving the service life of a device and an organic electroluminescent device comprising the same.
The phenanthroline compound shown in the formula 1 contains more than four nitrogen atoms, and an aromatic compound and heteroaryl are introduced into R 1-R14, so that electrons of the nitrogen atoms are more abundant, and the electron mobility is faster, and the electron transmission is promoted. In addition, nitrogen of sp2 hybridization orbitals is contained in the N-type charge generation layer (N-CGL), and this nitrogen forms a Gap state (Gap state) in combination with a metal doped as the N-type charge generation layer. Accordingly, electrons can be smoothly transferred from the P-type charge generation layer (P-CGL) to the N-type charge generation layer (N-CGL) through the gap state. The N-type charge generation layer may be composed of a metal or an organic material doped with N-type, wherein the metal is selected from Li, na, K, rb, cs, mg, ca, sr, ba, la, ce, sm, eu, tb, dy or Yb.
Further, by introducing various substituents into the above-described core structure, a compound having inherent properties of the introduced substituents can be synthesized. For example, a hole injection layer material and a hole transport layer material used for manufacturing an organic light emitting device are a compound that transports holes along the highest level orbital (HOMO) and a compound that blocks electrons crossing from the light emitting layer along the lowest level orbital (LUMO).
In particular, the core structure of the compound has stable characteristics to electrons and can improve the service life of the device. It is possible to prepare a material for electron transport layers and hole blocking materials having an appropriate energy bandgap.
In addition, by introducing various substituents into the core structure, the bandgap can be fine-tuned while improving the interfacial properties between organic materials, enabling the use of the materials to be diversified.
The charge generation layer (CG) includes a P-type charge generation layer (CGP) and an N-type charge generation layer (CGN), and is located between a first light emitting portion including a first hole transport layer, a first light emitting layer, a first electron transport layer, and a second light emitting portion including a second hole transport layer, a second light emitting layer, and a second electron transport layer in this order, and is composed of a PN junction structure connecting the first light emitting portion and the second light emitting portion.
That is, the above-described first electron transport layer has a PN junction structure thereon, and a charge generation layer including a P-type charge generation layer (CGP) and an N-type charge generation layer (CGN) is provided, and the N-type charge generation layer material may use the phenanthroline compound represented by formula 1 according to the present invention. Here, the N-type charge generation layer supplies electrons to the first electron transport layer of the first light emitting portion, the first electron transport layer supplies electrons to the first light emitting layer, the P-type charge generation layer supplies holes to the second hole transport layer of the second light emitting portion, and the second hole transport layer supplies holes to the second light emitting layer.
Here, for the first light emitting layer of the first light emitting portion; and second light emitting layers of the second light emitting part, each of which may include the same or different hosts and the same or different dopants. In addition, in the organic light emitting device according to the embodiment of the present invention, the hole injection layer (30) is located between the anode (20) and the first hole transport layer (40-1), and the second electron transport layer (60-2) is located between the electron injection layer (70) and the second light emitting layer (50-2).
The organic electroluminescent device may have various modifications, for example, a part of the organic layers may be omitted or added, may not be an overlapping structure, and may be an overlapping of 2 or more light emitting layers. In addition, the organic light emitting device may include an electron transport layer and an electron injection layer, in which case the electron transport layer and the electron injection layer may use the phenanthroline compound of the present invention.
The method for preparing the organic electroluminescent device of the present invention is not particularly limited, and may be prepared by using other methods and materials for preparing the luminescent device known to those skilled in the art, in addition to the o-phenanthroline compound represented by formula 1.
Examples
Example 1: synthesis of Compounds 1-3
1) Synthesis of intermediate 1-3-3
To compounds 1-3-1 (9.20 g,25 mmol) and 1-3-2 (8.06 g,50 mmol) was added p-toluenesulfonic acid monohydrate (23.8 g,253.65 mmol), and the resultant was stirred at 110℃for 8 hours. After the reaction was terminated, the resultant was cooled to room temperature, and the reaction solution was neutralized with an aqueous solution of a potassium carbonate compound. And dichloromethane extraction. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 1-3-3 (4.32 g, yield: 35.0%). LC-MS: M/Z492.02 (M+).
2) Synthesis of Compounds 1-3
After compound 1-3-3 (15.29 g,31 mmol) was dissolved in 1, 4-dioxane (130 mL), 1-3-4 (7.39 g,33 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to obtain the objective compound 1-3 (12.48 g, yield 68%). LC-MS: M/Z592.16 (M+).
Example 2: synthesis of Compounds 1-4
After compound 1-3-3 (15.29 g,31 mmol) was dissolved in 1, 4-dioxane (130 mL), 1-4-4 (7.36 g,33 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to obtain the objective compound 1-4 (11.74 g, yield 64%). LC-MS: M/Z591.17 (M+).
Example 3: synthesis of Compounds 1-7
After compound 1-3-3 (15.29 g,31 mmol) was dissolved in 1, 4-dioxane (130 mL), 1-7-1 (9.08 g,33 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to obtain the objective compound 1-7 (14.57 g, yield 73%). LC-MS: M/Z643.20 (M+).
Example 4: synthesis of Compounds 1-9
1) Synthesis of intermediate 1-9-3
After compound 1-9-1 (6.20 g,15 mmol) was dissolved in1, 4-dioxane (130 mL), 1-9-2 (12.04 g,32 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 1-9-3 (5.08 g, yield 40%). LC-MS: M/Z746.11 (M+).
2) Synthesis of Compounds 1-9
After compound 1-9-3 (22.77 g,31 mmol) was dissolved in 1, 4-dioxane (130 mL), 1-9-4 (7.39 g,33 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to obtain the objective compound 1-9 (14.18 g, yield 54%). LC-MS: M/Z846.25 (M+).
Example 5: synthesis of Compound 2-1
1) Synthesis of intermediate 2-1-3
After compound 2-1-1 (8.71 g,31 mmol) was dissolved in 1, 4-dioxane (130 mL), 2-1-2 (8.12 g,33 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 2-1-3 (8.61 g, yield 69%). LC-MS: M/Z402.06 (M+).
2) Synthesis of intermediate 2-1-4
2-1-3 (14 G,35 mol) was added to the reactor, followed by addition of 20g of hydrazine hydrate and 200g of ethanol, and the reaction solution was stirred at 55℃for 7 hours. The reaction solution was filtered, and the filtrate was extracted with toluene 3 times with an amount of 100g each time. Finally, the filtrate after toluene extraction was evaporated to dryness using a rotary evaporator to give 2-1-3 (8.27 g, yield 69%). LC-MS: M/Z342.11 (M+).
3) Synthesis of Compound 2-1
To compounds 2-1 to 4 (4.11 g,12 mmol) and 2-1 to 5 (8.06 g,50 mmol) was added p-toluenesulfonic acid monohydrate (23.8 g,253.65 mmol), and the resultant was stirred at 110℃for 8 hours. After the reaction was terminated, the resultant was cooled to room temperature, and the reaction solution was neutralized with an aqueous solution of a potassium carbonate compound. And dichloromethane extraction. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to obtain the objective compound 2-1 (1.85 g, yield: 26.0%). LC-MS: M/Z592.16 (M+).
Example 6: synthesis of Compounds 2-4
1) Synthesis of intermediate 2-4-3
To compound 2-4-1 (6.28 g,25 mmol) and 2-4-2 (8.06 g,50 mmol) was added p-toluenesulfonic acid monohydrate (23.8 g,253.65 mmol), and the resultant was stirred at 110℃for 8 hours. After the reaction was terminated, the resultant was cooled to room temperature, and the reaction solution was neutralized with an aqueous solution of a potassium carbonate compound. And dichloromethane extraction. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 2-4-3 (4.22 g, yield: 45.0%). LC-MS: M/Z375.00 (M+).
2) Synthesis of Compounds 2-4
After compound 2-4-3 (11.63 g,31 mmol) was dissolved in 1, 4-dioxane (130 mL), 2-4-4 (10.63 g,33 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to obtain the objective compound 2-4 (11.06 g, yield 75%). LC-MS: M/Z475.14 (M+).
Example 7: synthesis of Compounds 2-8
1) Synthesis of intermediate 2-8-3
2-8-1 (11.81 G,50 mmol) and 2-8-2 (5.46 g,50 mmol) were dissolved in glacial acetic acid (700 ml) and reacted for 12 hours. The material obtained after the completion of the reaction was introduced into H 2 O (500 ml), and the obtained solid was purified with water and methanol and dried. The resulting compound and 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) (12.5 g,55 mmol) were dissolved in methylene chloride (300 ml) and reacted for 1 hour. The reaction mixture was extracted with a benzene solvent and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. Purification by column chromatography or distillation gave intermediate 2-8-3 (7.32 g, yield 45%). LC-MS: M/Z325.09 (M+)
2) Synthesis of Compounds 2-8
2-8-3 (16.27 G,50 mmol) and 2-8-4 (21.55 g,75 mmol) were dissolved in glacial acetic acid (700 ml) and reacted for 12 hours. The material obtained after the completion of the reaction was introduced into H 2 O (500 ml), and the obtained solid was purified with water and methanol and dried. The resulting compound and 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) (12.5 g,55 mmol) were dissolved in methylene chloride (300 ml) and reacted for 1 hour. The reaction mixture was extracted with a benzene solvent and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. Purification by column chromatography or distillation afforded intermediate 2-81 (18.67. G, 63% yield). LC-MS: M/Z592.16 (M+)
Example 8: synthesis of Compounds 2-15
1) Synthesis of intermediate 2-15-3
After compound 2-15-1 (9.99 g,31 mmol) was dissolved in 1, 4-dioxane (130 mL), 2-15-2 (10.48 g,31 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 2-15-3 (7.03 g, yield 50%). LC-MS: M/Z452.03 (M+).
2) Synthesis of intermediate 2-15-4 after Compound 2-15-3 (9.99 g,20 mmol) was dissolved in tetrahydrofuran (200 mL), butyllithium (14 mL,22 mmol) was added at low temperature and stirred for half an hour, and N, N-dimethylformamide (1.5 mL) was slowly added dropwise to the reaction system to react for 2 hours. The resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to give the objective compound 2-15-4 (6.44 g, yield 80%). LC-MS: M/Z402.11 (M+).
3) Synthesis of Compounds 2-15
2-15-4 (20.12 G,50 mmol) and 2-15-5 (13.89 g,75 mmol) were dissolved in glacial acetic acid (700 ml) and reacted for 12 hours. The material obtained after the completion of the reaction was introduced into H 2 O (500 ml), and the obtained solid was purified with water and methanol and dried. The resulting compound and 2, 3-dichloro-5, 6-dicyanobenzoquinone (DDQ) (12.5 g,55 mmol) were dissolved in methylene chloride (300 ml) and reacted for 1 hour. The reaction mixture was extracted with a benzene solvent and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. Purification by column chromatography or distillation afforded intermediate 2-15 (15.89 g, 56% yield). LC-MS: M/Z567.17 (M+)
Example 9: synthesis of Compound 2-23
1) Synthesis of Compound 2-23
After compound 2-23-1 (4.97 g,15 mmol) was dissolved in1, 4-dioxane (130 mL), 2-23-2 (12.41 g,33 mmol), tetrakis triphenylphosphine palladium (1.8 g,1.5 mmol) and potassium carbonate (12.8 g, 93 mmol) were added thereto, and the resultant was stirred at 100℃for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature, and extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as a developing agent to obtain the objective compound 2-23 (7.53 g, yield 75%). LC-MS: M/Z669.70 (M+).
Device embodiments
As shown in fig. 1, the organic electroluminescent device of the present invention includes an anode (20), a first hole transport layer (40-1), a first light emitting layer (50-1) including a host and a dopant, a first light emitting unit including a first electron transport layer (60-1), a charge generation layer (CG) including a P-type charge generation layer (CGP) and an N-type charge generation layer (CGN), and a second light emitting unit including a second hole transport layer (40-2), a second light emitting layer (50-2) including a host and a dopant, a second light emitting layer including a second electron transport layer (60-2) and a cathode (80).
The layers of the organic electroluminescent device of the present invention may be formed by vacuum evaporation, sputtering, ion plating, or wet film forming such as spin coating, printing, etc., and the solvent used is not particularly limited.
< Experimental example 1> manufacture of organic light emitting device
1. First comparative example embodiment
Manufacturing of an organic electroluminescent device:
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. The patterned ITO glass substrate was then washed, then the substrate was placed in a vacuum chamber, and the standard pressure was set at 1 x 10 -6 torr. Thereafter, HATCN is evaporated on the ITO substrate to form a film with a thickness of Is formed by vapor deposition of HTL-1 on the first Hole Injection Layer (HIL) to a thickness ofIs deposited with CBP+GD-1 (3 wt%) on the hole transport layer to form a layer with a thickness ofSequentially doping and evaporating Yb (2 wt%) in Ref-1 to obtain a light-emitting layer (EML) with a thickness ofIs deposited with Al (thickness is) A cathode is formed, thereby manufacturing an organic electroluminescent device.
2. First embodiment
The organic electroluminescent device of the first embodiment was prepared by the same method as that of the first comparative example embodiment described above, except that the second electron transport material Ref-1 of the organic electroluminescent device was replaced with the compounds 1 to 3.
3. Second embodiment
The organic electroluminescent device of the second embodiment was prepared by the same method as that of the first comparative example embodiment described above, except that the second electron transport material Ref-1 of the organic electroluminescent device was replaced with the compounds 1 to 4.
Table 1 shows the results of testing the performance of the organic electroluminescent devices prepared in examples and comparative examples of the present invention.
TABLE 1
< Experimental example 2> fabrication of organic light emitting device
4. Second comparative example embodiment
Manufacturing of an organic electroluminescent device:
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. The patterned ITO glass substrate was then washed, then the substrate was placed in a vacuum chamber, and the standard pressure was set at 1 x 10 -6 torr. Thereafter, HATCN is evaporated on the ITO substrate to form a film with a thickness of Is formed by vapor deposition of HTL-1 on the first Hole Injection Layer (HIL) to a thickness ofIs deposited with CBP+RD-1 (3 wt%) to form a Hole Transport Layer (HTL) having a thickness ofIs sequentially coated with Alq3 (thickness) Yb (2 wt%) doped vapor deposition thickness in Ref-1 isHas a thickness of) P-type charge generation layer of (c). Then, the HTL-1 is evaporated to form a film with a thickness ofThe second Hole Transport Layer (HTL) of (C) was vapor deposited CBP+RD-1 (3 wt%) to a thicknessIs formed by sequentially evaporating Alq3 to a thickness ofIs deposited with LiF (thickness is) Al (thickness is /)) Thereby manufacturing an organic electroluminescent device.
5. Third embodiment
The organic electroluminescent device of the third embodiment was prepared by the same method as that of the second comparative example embodiment described above, except that only the N-type charge generation layer (N-CGL) of the organic electroluminescent device was replaced with compounds 1 to 7 in the second comparative example embodiment Ref-1.
6. Fourth embodiment
The organic electroluminescent device of the fourth embodiment was prepared by the same method as that of the second comparative example embodiment described above, except that only the N-type charge generation layer (N-CGL) of the organic electroluminescent device was replaced with compounds 1 to 9 in the second comparative example embodiment Ref-1.
7. Fifth embodiment
The organic electroluminescent device of the fifth embodiment was prepared by the same method as that of the second comparative example embodiment described above, and only the N-type charge generation layer (N-CGL) of the organic electroluminescent device was replaced with the compound 2-1 from the second comparative example embodiment Ref-1.
8. Sixth embodiment
An organic electroluminescent device of the sixth embodiment was prepared by the same method as that of the second comparative example embodiment described above, except that the N-type charge generation layer (N-CGL) of the organic electroluminescent device was replaced with the compound 2-4 from the second comparative example embodiment Ref-1.
9. Seventh embodiment
An organic electroluminescent device of the seventh embodiment was prepared by the same method as that of the above-described second comparative example embodiment, except that the N-type charge generation layer (N-CGL) of the organic electroluminescent device was replaced with the compounds 2 to 8 from the second comparative example embodiment Ref-1.
10. Eighth embodiment
An organic electroluminescent device of the eighth embodiment was prepared by the same method as that of the second comparative example embodiment described above, except that only the N-type charge generation layer (N-CGL) of the organic electroluminescent device was replaced with compounds 2 to 15 from the second comparative example embodiment Ref-1.
11. Ninth embodiment
An organic electroluminescent device of the ninth embodiment was prepared by the same method as that of the second comparative example embodiment described above, except that only the N-type charge generation layer (N-CGL) of the organic electroluminescent device was replaced with compounds 2 to 23 in the second comparative example embodiment Ref-1.
Table 2 shows the results of testing the performance of the organic electroluminescent devices prepared in examples and comparative examples of the present invention.
TABLE 2
As shown in table 1, the organic electroluminescent device including the specific compound combinations according to the present disclosure as CGL materials has a reduced driving voltage and improved efficiency compared to the organic electroluminescent device of the comparative substance.
The foregoing has outlined the basic principles, features, and advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (9)
1. A phenanthroline compound, the structure of which is represented by any one of formulas 1-2 to 1-3:
Wherein R 10 is selected from hydrogen, phenyl, naphthyl, anthryl, phenanthryl, pyridyl, quinolinyl, isoquinolinyl, phenanthroline; each R 12～R15 is independently selected from hydrogen;
Each L 3～L5 is independently a single bond, phenylene, pyridinyl; and at least one of L 4、L5 is a single bond;
n is 1.
2. A phenanthroline compound, wherein the phenanthroline compound is any one of the following:
3. An organic electroluminescent device, comprising:
a first electrode;
A second electrode; and
An organic layer between the first electrode and the second electrode;
the organic layer comprises the phenanthroline compound of any one of claims 1-2.
4. The organic electroluminescent device according to claim 3, wherein at least one of the organic layers is a charge generation layer or an electron transport layer.
5. The organic electroluminescent device according to claim 4, wherein the charge generation layer is an n-type charge generation layer.
6. The organic electroluminescent device according to claim 5, wherein the n-type charge generation layer is composed of a metal or an organic material doped with n-type, wherein the metal is selected from Li, na, K, rb, cs, mg, ca, sr, ba, la, ce, sm, eu, tb, dy or Yb.
7. An organic electroluminescent device, comprising:
a first electrode;
A second electrode;
a first light emitting portion of a first light emitting layer, which is located between the first electrode and the second electrode;
A second light emitting portion of a second light emitting layer, which is located between the second electrode and the first light emitting portion; and
A first charge generation layer located between the first light emitting portion and the second light emitting portion;
At least one of the first light emitting part, the second light emitting part, or the first charge generating layer comprises the phenanthroline compound of any one of claims 1-2.
8. Use of the phenanthroline compound according to any one of claims 1-2 in the fabrication of organic electroluminescent devices.
9. A display or lighting device comprising the organic electroluminescent device as claimed in claim 3 or 7.
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