CN117886786A - Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device - Google Patents
Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device Download PDFInfo
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- CN117886786A CN117886786A CN202410279916.9A CN202410279916A CN117886786A CN 117886786 A CN117886786 A CN 117886786A CN 202410279916 A CN202410279916 A CN 202410279916A CN 117886786 A CN117886786 A CN 117886786A
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- 125000003118 aryl group Chemical group 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 17
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- -1 dibenzofuranyl Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000002346 layers by function Substances 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 claims description 7
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- IRUFLAAZAAOXHM-UHFFFAOYSA-N 1-tert-butyl-2-phenylbenzene Chemical group CC(C)(C)C1=CC=CC=C1C1=CC=CC=C1 IRUFLAAZAAOXHM-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 77
- 239000000463 material Substances 0.000 abstract description 27
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 8
- 230000002035 prolonged effect Effects 0.000 abstract description 2
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- 238000004458 analytical method Methods 0.000 description 21
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 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 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
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- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
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- 229910000976 Electrical steel Inorganic materials 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
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- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical group CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 125000001725 pyrenyl group Chemical group 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002887 superconductor Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/658—Organoboranes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of organic photoelectric material preparation, in particular to an organic compound, an OLED (organic light emitting diode) with the compound and an organic light emitting device. According to the organic compound, the anthracene-based main body is matched with the phenanthrofuran structure and the limiting group, and the structure is deuterated to different degrees, so that the compound has excellent luminous efficiency and a better service life; the organic compound provided by the invention is used as a luminescent layer material, so that an organic luminescent device can effectively have lower driving voltage and maintain the stability of the voltage, the luminescent efficiency is improved, the service life is obviously prolonged, and the organic compound has good application prospect.
Description
Technical Field
The invention relates to the technical field of organic photoelectric material preparation, in particular to an organic compound, an OLED (organic light emitting diode) with the compound and an organic light emitting device.
Background
Organic Light Emitting Diodes (OLEDs), also known as organic electroluminescent devices, are techniques in which holes are injected from an anode and electrons from a cathode into a light emitting layer, respectively, by applying a voltage to an organic electroluminescent element, and the injected holes recombine with electrons to form excitons, resulting in light emission, which can convert electrical energy into light energy through an organic light emitting material.
In the field of conventional OLED materials, various researchers and technical developers have actively studied organic materials having light emission characteristics such as blue, which is one of three primary colors of light, and organic materials having charge transporting ability (possibility of becoming a semiconductor or superconductor) such as holes and electrons. The blue light electroluminescent material with high efficiency and high stability is designed, so that the blue light OLED device with good performance is prepared, and the blue light OLED device has important significance for realizing high-quality full-color display and high-efficiency white light emission.
Many blue light material studies are currently focused on structures with anthracenyl as the core. A related art provides a compound containing anthracene and a cyclic phenanthrene structure as a blue light-emitting host material, which has a high glass transition temperature and high molecular thermal stability, and suitable HOMO and LUMO energy levels and carrier mobility. After the blue light material is applied to OLED device manufacturing, the luminous efficiency of the device can be improved to a certain extent. However, experimental verification shows that the material has no obvious effect of improving the service life of the device in practical application, thereby affecting the further practicability of the technology.
Accordingly, there is a continuous effort to develop an organic light emitting device having low voltage driving, high luminance and long lifetime, and to find a suitable OLED photoelectric functional material for an OLED device to solve the above problems.
Disclosure of Invention
In order to solve the technical problems, the invention provides an organic compound, an OLED (organic light emitting diode) with the organic compound and a display or lighting device. The provided anthracene-based compound contains a phenanthrofuran structure and is deuterated to different degrees, so that the organic compound is used in an organic electroluminescent device, and the device can have higher efficiency and longer service life.
The organic compound provided by the invention is realized by the following technical scheme:
an organic compound having a structure represented by the following formula (I):
formula (I);
in the formula (I), R 1 -R 16 Each independently selected from hydrogen or deuterium; c atom C 1 Through C-C bond and R 9 -R 16 Any carbon atom in the position is attached; ar (Ar) 1 Independently selected from hydrogen, deuterium, substituted or unsubstituted C3-C36 aryl, substituted or unsubstituted C6-C36 aryl; the substituted substituents are each independently selected from one or more of deuterium, C6-C30 aryl, C3-C36 heteroaryl, C1-C6 alkoxy; the degree of deuteration of the structure of formula (I) is 10% to 100%.
Preferably, in the formula (I), ar 1 Independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, biphenyl, terphenyl, substituted or unsubstituted naphthyl, phenanthryl and dibenzofuranyl, wherein the substituent is selected from C6-C30 aryl.
According to one or more embodiments, the present invention provides an organic compound selected from any one of the chemical structures shown below, wherein "D" represents deuterium:
。
the invention also provides an application of the organic light-emitting diode in an organic light-emitting diode.
The invention also provides an organic electroluminescent device, which comprises:
a substrate layer;
a first electrode over the substrate;
an organic light emitting functional layer over the first electrode;
a second electrode over the organic light emitting functional layer;
the organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprises the organic compound as described above.
Preferably, the light emitting layer further comprises a boron nitrogen compound having a structure represented by the following formula (II):
formula (II);
in the formula (II), the R 17 Independently selected from hydrogen, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; r is R 18 Independently selected from methyl, tert-butyl or phenyl; r is R 19 -R 20 Each independently selected from hydrogen, deuterium, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl; ar (Ar) 2 Independently selected from deuterated or non-deuterated C1-C20 alkyl, deuterated or non-deuterated C6-C30 arylsilane groups; the substituted substituents are each independently selected from one or more of C1-C20 alkyl, C6-C30 aryl and C3-C36 heteroaryl.
Preferably, in the formula (II), R 17 Independently selected from tert-butyl, C1-C6 alkyl substituted or unsubstituted cyclohexane.
Preferably, in the formula (II), R 19 -R 20 Each independently selected from the group consisting of substituted phenyl, biphenyl, t-butylphenyl, t-butylbiphenyl, substituted or unsubstituted 1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthyl, phenanthrene [4,5-BCD ]]A furyl group; the substituted substituents are each independently selected from deuterium, tert-butyl, tert-butylphenyl, 1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthyl; and R is 19 -R 20 At least one selected from phenanthrene [4,5-BCD ]]Furyl group, which is represented by formula (III)"represents a linking site where the N atom of formula (II) may be attached to any carbon atom of the group of formula (III) that may be substituted with hydrogen.
Preferably, in the formula (II), ar 2 Independently selected from deuterated or non-deuterated tertiary butyl, triarylsilane.
Preferably, the boron nitrogen compound is selected from any one of the following chemical structures, wherein "D" represents deuterium:
。
the present invention also provides a formulation comprising an organic compound having a structure as shown in formula (I) above or a composition as described above and at least one solvent. The solvent is not particularly limited, and an unsaturated hydrocarbon solvent, a halogenated saturated hydrocarbon solvent, a halogenated unsaturated hydrocarbon solvent, an ether solvent or an ester solvent, which are well known to those skilled in the art, may be used; wherein the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetrahydronaphthalene, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc.; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane or bromocyclohexane, etc.; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene, trichlorobenzene or the like; the ether solvent is tetrahydrofuran, tetrahydropyran, or the like; the ester solvent is alkyl benzoate and the like.
The invention also provides a composition which comprises the organic compound shown in the formula (I) and the formula (II) and the boron-nitrogen compound shown in the formula (II):
formula (II);
in the formula (II), the R 17 Independently selected from hydrogen, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; r is R 18 Independently selected from methyl, tert-butyl or phenyl; r is R 19 -R 20 Each independently selected from hydrogen, deuterium, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl; ar (Ar) 2 Independently selected from deuterated or non-deuterated C1-C20 alkyl, deuterated or non-deuterated C6-C30 arylsilane groups; the substituted substituents are each independently selected from one or more of C1-C20 alkyl, C6-C30 aryl and C3-C36 heteroaryl.
The organic electroluminescent device of the present invention can be used in an OLED lighting or display device.
The invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices as described above.
In summary, compared with the prior art, the invention has the following beneficial effects:
according to the organic compound, the anthryl main body is matched with the phenanthrofuran structure and the limiting aromatic group, and the deuteration is carried out on the compound structure to different degrees, so that the compound has excellent luminous efficiency and long service life; meanwhile, after the organic compound and the boron-nitrogen compound are matched for the light-emitting layer to prepare the organic light-emitting device, the organic light-emitting device can be effectively enabled to have lower driving voltage, the stability of the voltage is kept, the light-emitting efficiency is improved, and the service life of the device can be prolonged better.
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.
The aryl group refers to a generic term that a monovalent group remains after one hydrogen atom is removed from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and may be a monocyclic aryl group or a condensed ring aryl group, and examples thereof include, but are not limited to, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, and the like.
The heterocycloalkyl group according to the present invention means a cyclic alkyl group having a single ring or multiple rings condensed. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like, or polycyclic structures such as spirocycloalkyl, and the like. The hetero atom may be oxygen atom, sulfur atom, nitrogen atom, etc.
Throughout this specification, unless explicitly stated to the contrary, the word "comprise" or variations such as "comprises" or "comprising", will be understood to imply the inclusion of other elements but not the exclusion of any other element. Furthermore, it will be understood that throughout the specification, when an element such as a layer, film, region or substrate is referred to as being "on" or "over" another element, it can be "directly on" the other element or intervening elements may also be present. In addition, "on … …" or "above … …" means above the target portion, and not necessarily above in the direction of gravity.
An object of the present invention is to provide an organic electroluminescent device comprising: a substrate layer; a first electrode over the substrate; an organic light emitting functional layer over the first electrode; a second electrode over the organic light emitting functional layer; the organic light-emitting functional layer includes a light-emitting layer including an organic compound having an anthracene-based and phenanthrofuran structure.
In one embodiment of the present invention, a light-emitting layer in an organic electroluminescent (OLED) device comprises, as a light-emitting host material, one or more compositions of a compound represented by the above general formula (i); also comprises one or more of the compounds shown in the general formula (II) as a light-emitting doping material.
In a preferred embodiment of the present invention, there is provided an OLED comprising a substrate, an anode, a cathode, an organic light emitting functional layer, wherein the organic light emitting functional layer may comprise a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, an electron injecting layer, etc., and may also comprise only a light emitting layer and one or more other layers; wherein the light-emitting layer comprises one or more of the compounds represented by the above general formula (I); preferably, one or more compounds of the formula (II) are also included. Optionally, a cover layer, protective layer and/or encapsulation layer is also provided over the organic light-emitting functional layer.
The substrate of the present invention may be any substrate used in a typical organic light emitting device. The flexible PI film can be a glass or transparent plastic substrate, a substrate made of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness and waterproofness, and the use direction is different according to the different properties of the substrates.
As the material of the hole injection layer, the hole transport layer, and the electron injection layer, any material can be selected from known materials for use in an OLED device.
The present invention will be specifically described with reference to the following examples. All starting materials and solvents were commercially available unless specified, and the solvents were used as such and were not further processed.
Example 1: synthesis of Compounds 1-003
The synthetic route is as follows:
1) 1-003-1 (15 mmoL) and 1-003-2 (15 mmoL) were dissolved in 150mL of 1, 4-dioxane and 100mL of H in a three-necked flask 2 K of O 2 CO 3 (20 mmoL) was added. Pd (P (t-Bu) was then added thereto 3 ) 2 (0.15 mmoL) under reflux conditions in an argon atmosphereStirred for 5 hours. After the reaction was completed and cooled to room temperature, the reaction solution was transferred to a separating funnel and extracted with water and toluene. The extract was treated with MgSO 4 Drying, filtering and concentrating, and purifying the sample by silica gel column chromatography to obtain an intermediate product 1-003-3;
2) In a two-necked flask, the intermediate 1-003-3 (10 mmoL), N-bromosuccinimide (NBS) (12 mmoL) and 100mL Dimethylformamide (DMF) were added and stirred under argon atmosphere at room temperature for 10 hours. After the completion of the reaction, the reaction solution was transferred to a separating funnel, and extracted with water and ethyl acetate. The extract was treated with MgSO 4 Drying, filtering and concentrating, and purifying the sample by silica gel column chromatography to obtain an intermediate product 1-003-4;
3) 1-003-4 (6 mmoL) and 1-003-5 (6 mmoL) were dissolved in 150mL of 1, 4-dioxane and 100mL of H in a three-necked flask 2 K of O 2 CO 3 (20 mmoL) was added. Pd (P (t-Bu) was then added thereto 3 ) 2 (0.06 mmoL) was stirred under reflux under argon atmosphere for 5 hours. After the reaction was completed and cooled to room temperature, the reaction solution was transferred to a separating funnel and extracted with water and toluene. The extract was treated with MgSO 4 Drying, filtering and concentrating, and purifying the sample by silica gel column chromatography to obtain the final product 1-003.
Structure of test target product 1-003: LC-MS (m/z) (m+), theoretical value 464.28 and test value 464.76 were obtained by liquid chromatography-mass spectrometry analysis.
Example 2: synthesis of Compounds 1-009
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-009 were synthesized and analyzed by liquid chromatography-mass spectrometry to give LC-MS (m/z) (m+).
Example 3: synthesis of Compounds 1-011
Referring to the synthesis procedure and reaction conditions of example 1, compounds 1-011 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+):theoretical 501.21 and test 501.67.
Example 4: synthesis of Compounds 1-019
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-019 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (M+).
Example 5: synthesis of Compounds 1-023
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-023 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 6: synthesis of Compounds 1-028
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-028 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 7: synthesis of Compounds 1-029
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-029 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 8: synthesis of Compounds 1-031
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-031 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 9: synthesis of Compounds 1-036
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-036 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 10: synthesis of Compounds 1-040
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-040 were synthesized and LC-MS (m/z) (m+), theoretical 553.24 and test 553.68 were obtained by liquid chromatography-mass spectrometry analysis.
Example 11: synthesis of Compounds 1-042
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-019 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (M+).
Example 12: synthesis of Compounds 1-062
With reference to the synthesis procedure and reaction conditions of example 1, compounds 1-062 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 13: synthesis of Compound 2-001
The synthetic route is as follows:
the synthesis steps are as follows:
1) Compound 2-001-1 (1 mmoL) and compound 2-001-2 (1 mmoL) were dissolved in 50mL toluene solution. Sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL) and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added under nitrogen atmosphere. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4, intermediate products 2-001-3;
2) Intermediate 2-001-3 (1 mmoL) and compound 2-001-4 (1 mmoL) were dissolved in 50mL toluene solution. Sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL) and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added under nitrogen atmosphere. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4, intermediate products 2-001-5;
3) Intermediate 2-001-5 (1 mmoL) and compound 2-001-6 (1 mmoL) were dissolved in 50mL toluene solution. Sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL) and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added under nitrogen atmosphere. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4, intermediate products 2-001-7;
4) Intermediate 2-001-7 (1 mmoL) and compound 2-001-8 (1 mmoL) were dissolved in 50mL toluene solution. Sodium tert-butoxide (2 mmoL), palladium acetate (0.05 mmoL) and tri-tert-butylphosphine tetrafluoroborate (0.5 mmoL) were added under nitrogen atmosphere. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:4, intermediate products 2-001-9;
5) Intermediate 2-001-9 (1 mmoL) was dissolved in 60 mL anhydrous tert-butylbenzene. The reaction was cooled to-78℃and BuLi (1 mL,2 mmoL,2M in hexane) was slowly added. After 4 hours of reaction at-78℃BBr (3247 mg,1 mmoL) was slowly added. After 1 hour of reaction at-50 ℃, the temperature was raised to room temperature, then N, N-diisopropylethylamine (387 mg,3 mmoL) was added, followed by heating to 120℃for reaction for 12 hours. After cooling to room temperature, 5 mL aqueous sodium acetate (1M) was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:8 to give the final product 2-001.
Structure of test target product 2-001: LC-MS (m/z) (m+), theoretical value 974.39 and test value 974.75 were obtained by liquid chromatography-mass spectrometry analysis.
Example 14: synthesis of Compounds 2-009
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-009 were synthesized and analyzed by liquid chromatography-mass spectrometry to give LC-MS (m/z) (m+).
Example 15: synthesis of Compound 2-017
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-017 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 16: synthesis of Compounds 2-025
Referring to the synthesis procedure and reaction conditions of example 13, compounds 2-025 were synthesized and analyzed by liquid chromatography-mass spectrometry to give LC-MS (m/z) (M+):theoretical 1023.48 and test 1023.96.
Example 17: synthesis of Compound 2-029
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-029 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 18: synthesis of Compounds 2-056
The synthetic route is as follows:
with reference to the synthesis procedure and reaction conditions of example 13, compounds 2-056 were synthesized and analyzed by liquid chromatography-mass spectrometry to give LC-MS (m/z) (m+).
Example 19: synthesis of Compound 2-060
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-060 were synthesized and LC-MS (m/z) (m+), theoretical 1124.53 and 1124.97 were obtained by liquid chromatography-mass spectrometry analysis.
Example 20: synthesis of Compound 2-064
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-064 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 21: synthesis of Compound 2-066
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-066 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 22: synthesis of Compound 2-076
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-076 were synthesized and analyzed by liquid chromatography-mass spectrometry to give LC-MS (m/z) (m+).
Example 23: synthesis of Compound 2-081
With reference to the synthesis procedure and reaction conditions of example 13, compound 2-081 was synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+): theoretical 978.57 and test 978.85.
Example 24: synthesis of Compounds 2-086
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-086 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 25: synthesis of Compounds 2-096
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-096 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
Example 26: synthesis of Compounds 2-097
With reference to the synthesis procedure and reaction conditions of example 13, compounds 2-097 were synthesized by liquid chromatography-mass spectrometry analysis to give LC-MS (m/z) (m+).
The following examples of the application of the organic compounds of the present invention to OLED devices are given to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples were purchased commercially or synthesized by themselves.
As a reference preparation mode of an embodiment of a device, the invention is to vapor-deposit 50-500nm ITO/Ag/ITO as an anode on an alkali-free glass substrate, vapor-deposit a hole injection layer (5 nm-20 nm), a hole transport layer (50-120 nm), a light-emitting auxiliary layer (5-120 nm), a light-emitting layer (20-50 nm), an electron transport layer (20-80 nm) and an electron injection layer (1-10 nm), prepare a semitransparent cathode by co-vapor-depositing Mg and Ag (weight ratio 10:1, 10-50 nm), and vapor-deposit a cover layer compound. And finally, encapsulating the light-emitting device by using an epoxy resin adhesive in a nitrogen atmosphere.
In a preferred embodiment, the OLED device provided by the present invention has the structure: the alkali-free glass substrate was first washed with an ultrasonic cleaner using isopropyl alcohol for 15 minutes, and then subjected to a UV ozone washing treatment in air for 30 minutes. The treated substrate was vapor-deposited with ITO/Ag/ITO 100nm as an anode by vacuum vapor deposition, then a hole injection layer (HT: PD,10nm, 2%), a hole transport layer (HT, 30 nm), a light emission auxiliary layer (BP, 5 nm), a blue light emitting layer (host material: dopant material=compound 1-003: compound 2-001 (weight ratio 98:2, 30 nm)), an electron transport layer (compound ET: liq=1:1, 30 nm), and an electron injection layer (LiF, 0.5 nm) were sequentially stacked and vapor-deposited, and then Mg and Ag (weight ratio 10:1, 15 nm) were co-vapor-deposited to form a semitransparent cathode, and then compound CPL (65 nm) was vapor-deposited as a capping layer. Finally, the light-emitting device was encapsulated with an epoxy resin adhesive under a nitrogen atmosphere, which was designated as application example 1. The molecular structural formula of the relevant material is shown below (particularly preferably selected from the following structures, but does not represent the present invention limited to the following structures):
application example 2-application example 12 and comparative example 1 were prepared with reference to the method provided in application example 1 above, except that the compounds 1-003 in application example 1 were replaced with the compounds listed in table 1 as host materials, respectively. The structure of Ref-1 used in the comparative example is as follows:。
with Keithley 2365A digital nanodevicesThe voltage meter tests the current of the OLED device under different voltages, and then divides the current by the light emitting area to obtain the current density of the OLED device under different voltages; testing the brightness and radiant energy density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and brightness of the OLED device under different voltages, the OLED device with the same current density (10 mA/cm 2 ) BI=E/CIEy, which refers to Blue Index in Blue light and is also a parameter for measuring the luminous efficiency of Blue light, E refers to current efficiency, and CIEy refers to an ordinate color point obtained by taking the device luminous half-width wavelength into CIE1930 software. The test data are shown in table 1.
As can be seen from table 1, application examples 1 to 12 have lower operating voltage, higher BI light emitting efficiency and longer service life compared to comparative example 1. The improvement of the performance of each application example is based on the better thermal stability and charge transmission capability of the organic compound material.
In order to further verify the excellent properties of the organic compounds provided by the present invention, application examples 13 to 26, and comparative examples 2 to 5 were prepared with reference to the method provided in application example 1 described above; the difference was only that the compounds 1-003 and the compounds 2-001 in application example 1 were replaced with the compounds listed in Table 2, respectively. The new material structure referred to in comparative example Ref-2 in table 2 is as follows:。/>
as can be seen from table 2, application examples 13 to 26 have lower operating voltage, higher BI light emitting efficiency and longer service life than comparative examples 2 to 5. The improvement in the performance of each application example is based on the better charge transport capacity of the organic compound material. Therefore, the collocation of the doped material and the main body material is better, so that the blue light emitting layer can better realize the balance of electron and hole transmission and the exciton conversion rate, reduce the power consumption of the device, and prolong the service life of the panel and the luminous efficiency of the device.
The present embodiment is only for explanation of the present invention and is not to be construed as limiting the present invention, and modifications to the present embodiment, which may not creatively contribute to the present invention as required by those skilled in the art after reading the present specification, are all protected by patent laws within the scope of claims of the present invention.
Claims (14)
1. An organic compound, characterized in that the organic compound has a structure represented by the following formula (I):
formula (I);
in the formula (I), R 1 -R 16 Each independently selected from hydrogen or deuterium; c atom C 1 Through C-C bond and R 9 -R 16 Any carbon atom in the position is attached; ar (Ar) 1 Independently selected from hydrogen, deuterium, substituted or unsubstituted C3-C36 aryl, substituted or unsubstituted C6-C36 aryl; the substituted substituents are each independently selected from one or more of deuterium, C6-C30 aryl, C3-C36 heteroaryl, C1-C6 alkoxy; the degree of deuteration of the structure of formula (I) is 10% to 100%.
2. The organic compound according to claim 1, wherein in the formula (I), ar 1 Independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, biphenyl, terphenyl, substituted or unsubstituted naphthyl, phenanthryl and dibenzofuranyl, wherein the substituent is selected from C6-C30 aryl.
3. The organic compound according to claim 1, wherein the organic compound is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:
。
4. use of an organic compound according to any one of claims 1-3 for the preparation of an organic electroluminescent device.
5. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises:
a substrate layer;
a first electrode over the substrate;
an organic light emitting functional layer over the first electrode;
a second electrode over the organic light emitting functional layer;
the organic light-emitting functional layer comprises a light-emitting layer; the light-emitting layer comprising the organic compound according to any one of claims 1 to 3.
6. The organic electroluminescent device according to claim 5, wherein the light-emitting layer further comprises a boron-nitrogen compound having a structure represented by the following formula (II):
formula (II);
in the formula (II), the R 17 Independently selected from hydrogen, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; r is R 18 Independently selected from methyl, tert-butyl or phenyl; r is R 19 -R 20 Each independently selected from hydrogen, deuterium, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl; ar (Ar) 2 Independently selected from deuterated or non-deuterated C1-C20 alkyl, deuterated or non-deuterated C6-C30 arylsilane groups; the substituted substituents are each independently selected from one or more of C1-C20 alkyl, C6-C30 aryl and C3-C36 heteroaryl.
7. The organic electroluminescent device as claimed in claim 6, wherein in the formula (II), R 17 Independently selected from tert-butyl, C1-C6 alkyl substituted or unsubstituted cyclohexane.
8. According to claim6, wherein in the formula (II), R 19 -R 20 Each independently selected from the group consisting of substituted phenyl, biphenyl, t-butylphenyl, t-butylbiphenyl, substituted or unsubstituted 1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthyl, phenanthrene [4,5-BCD ]]A furyl group; the substituted substituents are each independently selected from deuterium, tert-butyl, tert-butylphenyl, 1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthyl; and R is 19 -R 20 At least one selected from phenanthrene [4,5-BCD ]]Furyl group, which is represented by formula (III)"represents a linking site where the N atom of formula (II) may be attached to any carbon atom of the group of formula (III) that may be substituted with hydrogen.
9. The organic electroluminescent device according to claim 6, wherein Ar in the formula (II) 2 Independently selected from deuterated or non-deuterated tertiary butyl, phenyl, triarylsilane.
10. The organic electroluminescent device of claim 6, wherein the boron nitrogen compound is selected from any one of the following chemical structures, wherein "D" represents deuterium:
。/>
11. a formulation comprising an organic compound according to any one of claims 1-3 and at least one solvent.
12. A composition comprising an organic compound according to any one of claims 1 to 3 and a boron nitrogen compound of the structure of formula (II):
formula (II);
in the formula (II), the R 17 Independently selected from hydrogen, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl; r is R 18 Independently selected from methyl, tert-butyl or phenyl; r is R 19 -R 20 Each independently selected from hydrogen, deuterium, C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl; ar (Ar) 2 Independently selected from deuterated or non-deuterated C1-C20 alkyl, deuterated or non-deuterated C6-C30 arylsilane groups; the substituted substituents are each independently selected from one or more of C1-C20 alkyl, C6-C30 aryl and C3-C36 heteroaryl.
13. Use of an organic electroluminescent device as claimed in any one of claims 5 to 10 in a display or lighting apparatus.
14. A display or lighting device, characterized in that the device comprises an organic electroluminescent device as claimed in any one of claims 5-10.
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