CN116239478A - Spiro compound and organic electroluminescent device - Google Patents
Spiro compound and organic electroluminescent device Download PDFInfo
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- CN116239478A CN116239478A CN202310095913.5A CN202310095913A CN116239478A CN 116239478 A CN116239478 A CN 116239478A CN 202310095913 A CN202310095913 A CN 202310095913A CN 116239478 A CN116239478 A CN 116239478A
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- 150000003413 spiro compounds Chemical class 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- -1 amine compounds Chemical class 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 60
- 230000005525 hole transport Effects 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 17
- 239000007924 injection Substances 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 239000004973 liquid crystal related substance Substances 0.000 claims description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 29
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 5
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 150000002220 fluorenes Chemical class 0.000 abstract description 4
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical compound C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 abstract description 3
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical class NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 abstract description 2
- 150000001924 cycloalkanes Chemical group 0.000 abstract 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical class C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- XCHARIIIZLLEBL-UHFFFAOYSA-N Medicagenic acid 3-O-beta-D-glucoside Chemical compound C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C(O)=O)C)(C)C1=CCC2C3(C)CC(O)C4OC1OC(CO)C(O)C(O)C1O XCHARIIIZLLEBL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 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
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention discloses a spiro compound and an organic electroluminescent device, and relates to the technical field of organic electroluminescent, wherein compounds in the compound all have cycloalkane groups such as a three-membered ring or a four-membered ring or a five-membered ring or a six-membered ring, the cycloalkane and fluorenyl are bridged to form fluorene compounds, the fluorene compounds are connected with biphenylamine compounds to form amine compounds, and the amine compounds and phenyl groups of 9, 9-diphenyl fluorene are synthesized into the compound of the invention through Buchwald-Hartwig Cross Coupling Reaction. The introduction of the specific groups such as the three-membered ring, the four-membered ring, the five-membered ring and the six-membered ring effectively increases the steric hindrance and the torque of the material, further improves the triplet state energy level of the material, effectively blocks the reverse transmission of energy from the light-emitting layer to the transmission layer, and further improves the light-emitting efficiency and the service life of the device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a spiro compound and an organic electroluminescent device.
Background
Organic Light-emitting Devices (OLEDs) have the advantages of being thin and Light, active Light emission, wide viewing angle, fast response, low energy consumption, low temperature, excellent anti-vibration performance, and potentially flexible design. The OLED is an all-solid-state device, has no vacuum cavity and no liquid component, so the OLED is shock-resistant, convenient to use, and has the characteristics of high resolution, wide viewing angle, wide working temperature range and the like, and can be widely applied to the fields of weaponry and severe environments. In addition, OLEDs can also be used as planar backlights and illumination sources in the display field. Therefore, the OLED has a good development prospect.
OLEDs do not require the use of backlighting systems in LCDs that selectively block certain backlighting areas during operation to allow images to appear, while OLEDs emit themselves, which is particularly important for battery-powered devices because OLEDs do not require backlighting systems and consume less power than LCDs (most of the power consumed by LCDs is used in backlighting systems).
An OLED is a current-type organic light emitting device, which is a phenomenon of emitting light by injection and recombination of carriers, and the intensity of the light emission is proportional to the current injected. Under the action of an electric field, holes generated by the anode and electrons generated by the cathode of the OLED move, are respectively injected into the hole transport layer and the electron transport layer, and migrate to the light emitting layer. When the two meet at the light emitting layer, an energy exciton is generated, thereby exciting the light emitting molecule to finally generate visible light.
Since there is a great gap between the external quantum efficiency and the internal quantum efficiency of the OLED, the development of the OLED is greatly restricted, and therefore how to improve the light extraction efficiency of the OLED is also a hot spot of research. The interface of the ITO film and the glass substrate and the interface of the glass substrate and air can generate total reflection, the light emitted to the front external space of the OLED device occupies about 20 percent of the total quantity of the organic material film EL, and the rest about 80 percent of light is mainly limited in the organic material film, the ITO film and the glass substrate in a guided wave mode, so that the development and the application of the OLED are seriously restricted, the total reflection effect in the OLED device is reduced, the proportion of light coupled to the front external space of the device is improved, and the performance of the device is further improved.
In order to fully develop the excellent characteristics of the organic light-emitting device, materials constituting the organic layer in the device, for example, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and the like are stable and effective materials as backsides, and thus development of new materials is continuously demanded.
Disclosure of Invention
The invention aims at solving the technical problems and provides a spiro compound and an organic electroluminescent device.
The aim of the invention can be achieved by the following measures:
a spiro compound having a structure represented by formula 1:
wherein, the liquid crystal display device comprises a liquid crystal display device,
R 1 and R is R 3 Linking to make R 1 -C-R 3 Cycloalkyl groups constituting C3-C20 or cycloalkenyl groups constituting C3-C20;
R 2 the following groups selected from deuterium or deuterated or non-deuterated: one or more of C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aromatic group, or C1-C10 alkyl substituted C6-C20 aromatic group;
n is an integer of 0 to 5.
R in the present invention 1 And R is R 3 Is alkyl or alkenyl, and the sum of the carbon atoms of the two is 2-19.
Preferably, R 1 And R is R 3 Linking to make R 1 -C-R 3 Cycloalkyl groups constituting C3-C12 or cycloalkenyl groups constituting C3-C12.
Further preferably, R 1 -C-R 3 One of a cycloalkyl group constituting C3-C10, a cycloalkyl group constituting C3-C9, a cycloalkyl group constituting C3-C8, a cycloalkyl group constituting C3-C7, or a cycloalkyl group constituting C3-C6.
More preferably, R 1 -C-R 3 To form cyclopropane, cyclobutane, cyclopentane and cyclohexane.
Preferably, R 2 The following groups, which are deuterated or non-deuterated: C1-C4 alkyl, phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, 9-dimethylfluorenyl.
Further preferably, R 2 The following groups, which are deuterated or non-deuterated: one or more of methyl, ethyl, propyl, phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, 9-dimethylfluorenyl.
More preferably, R 2 Methyl, ethyl, propyl, deuterated methyl, deuterated ethyl or deuterated propyl.
Preferably, n is an integer from 0 to 4, in particular an integer from 0 to 3, such as in particular=0, 1, 2, 3.
In a preferred embodiment, R 1 -C-R 3 The cycloalkyl group is a monocycloalkyl group.
Further preferably, the structural formula of the compound of the present invention is represented by the following formulas 2 to 4:
still further, the compound of the present invention may be any one of the following compounds:
the spiro compound with the structure shown in the formula 1 has the following synthetic reaction route:
an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the compound.
Further, the organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer; at least one layer of the hole injection layer, the first hole transport layer, the second hole transport layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer contains the compound.
Further, the hole transport layer contains the above compound.
An electronic display device comprising the organic electroluminescent device.
An OLED lighting device comprising the organic electroluminescent device.
The room temperature of the invention is 25+/-5 ℃.
The invention has the beneficial effects that:
the invention designs a brand new organic electroluminescent material. The material has the following characteristics:
1. the compounds in the compounds of the invention all have naphthene groups (such as three-membered ring, four-membered ring, five-membered ring, six-membered ring and the like), the naphthene ring and fluorenyl are bridged to form fluorene compounds, the fluorene compounds are connected with biphenylamine compounds to form amino compounds, and the amino compounds and phenyl groups of 9, 9-diphenylfluorene are synthesized into the compounds of the invention through Buchwald-Hartwig Cross Coupling Reaction. The introduction of the specific groups such as the three-membered ring, the four-membered ring, the five-membered ring and the six-membered ring effectively increases the steric hindrance and the torque of the material, further improves the triplet state energy level of the material, effectively blocks the reverse transmission of energy from the light-emitting layer to the transmission layer, and further improves the light-emitting efficiency and the service life of the device.
2. The introduction of cycloparaffin groups (such as three-membered ring, four-membered ring, five-membered ring, six-membered ring and the like) on fluorenyl effectively increases the steric hindrance and torque of the material, and the large steric hindrance and torque improve the alignment property of the material when vapor deposition is carried out to form a film, so that the film formed by vapor deposition has certain anisotropy, and the property effectively solves the problems of transverse electric leakage and crosstalk of devices.
3. The fluorenyl group containing the naphthene group (such as a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, and the like) is connected with the phenyl group of the 9, 9-diphenyl fluorene through nitrogen, so that the torque and the space rotation freedom degree of the material are greatly improved, the rigidity of the material is reduced, the glass transition temperature of the material is further reduced, and the problem of hole blocking of the material in the evaporation process is further avoided. Meanwhile, the high torque and the space rotation freedom degree greatly improve the solvent property of the material in the solvent, thereby obviously reducing the cleaning difficulty and the cleaning cost of the mask, improving the utilization efficiency of the mask and improving the production efficiency.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to the present invention;
the reference numerals in the figures represent: 1-anode, 2-hole injection layer, 3-first hole transport layer, 4-second hole transport layer, 5-light emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode.
FIG. 2 is an HPLC chart of Compound 4 prepared in example 1 of the present invention.
FIG. 3 is a DSC chart of Compound 4 prepared in example 1 of the present invention, and as can be seen from FIG. 3, tg value of Compound 4 is 130.00 ℃.
FIG. 4 is a TGA spectrum of the compound 4 prepared in example 1 of the present invention, and as can be seen from FIG. 4, the thermal weight loss temperature Td value is 417.73 ℃.
Fig. 5 is a life chart of the organic electroluminescent device in application example 1 and comparative example 1 of the present invention; as can be seen from fig. 5, the T97% lifetimes of the organic electroluminescent devices according to application example 1 and comparative example 1 of the present invention were 709h and 461h, respectively.
FIG. 6 is an NMR chart of compound 4 prepared in example 1 of the invention.
Detailed Description
Embodiments of the various aspects are further illustrated and described below. It should be understood that the description herein is not intended to limit the claims to the particular aspects described. On the contrary, the intent is to cover alternatives, modifications and equivalents as included within the spirit and scope of the disclosure as defined by the appended claims.
As used herein, in "deuterated" or "non-deuterated," the term "deuterated" refers to the fact that at least one hydrogen in the group is re-coordinated with deuterium. The term "non-deuterated" means that all hydrogens in the group are not re-coordinated to deuterium.
As used herein, an "aromatic group" refers to a group containing one or more aromatic rings, where the aromatic rings include, but are not limited to, benzene, naphthalene, phenanthrene, fluorene, acenaphthene, pyridine, pyrimidine, pyrrole, furan, thiophene, and the like. C6-C30 in an aromatic radical of C6-C30 means that the radical contains from 6 to 30 carbon atoms. In the C1-C10 alkyl-substituted C6-C20 aromatic group, C1-C10 means the number of carbon atoms of the substituent, and C6-C20 means the number of carbon atoms of the aromatic group containing no substituent. Aromatic groups can be divided into monocyclic aryl groups and polycyclic aryl groups. Specific aromatic groups in the present invention include, but are not limited to, phenyl, biphenyl, terphenyl, anthracenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothienyl, 9-spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, and the like. The aromatic groups may be substituted and unsubstituted.
"cycloalkyl" herein refers to a monocyclic or fused ring (fused ring means that each ring in the system shares an adjacent pair of carbon atoms with the other rings in the system) group that is entirely carbon, wherein one or more of the rings is a saturated alicyclic ring, typically having 3 to 20 carbon atoms, preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms. Cycloalkyl groups can be divided into monocyclic alkyl groups having only one ring and fused ring alkyl groups having multiple rings. Examples of monocyclic alkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. Cycloalkyl groups may be substituted and unsubstituted.
"cycloalkenyl" herein refers to a single ring or fused ring of all carbons ("fused" ring means that each ring in the system shares an adjacent pair of carbon atoms with the other rings in the system), wherein one or more rings do not have a fully attached pi-electron system and contain at least one alkenyl group, typically having 3-20 carbon atoms, preferably 3-12 carbon atoms, more preferably 3-10 carbon atoms, and examples of cycloalkenyl include, but are not limited to, cyclopentene, cyclohexene, cyclohexadiene, cycloheptatriene. Cycloalkenyl groups can be substituted and unsubstituted.
"deuterated aromatic group" herein refers to a group in which one or more hydrogen atoms in the aromatic group are replaced with deuterium.
"deuterated phenyl" herein refers to a group in which 1 or more hydrogens in the phenyl group are replaced with deuterium.
Herein, "n is an integer of 0 to 5" means that n is 0, 1, 2, 3, 4, 5, and "n is an integer of 0 to 3" means that n is 0, 1, 2, 3.
The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
Example 1:
the synthesis method of the compound 4 is as follows:
1-a (29 g, 67mmol,1 eq) and 1-b (25 g,184mmol,1.1 eq) were dissolved in 300mL of toluene under nitrogen protection, pd (Pph) 4 (3.8 g,3.34mmol,2% eq), potassium carbonate (69 g,0.5mol,3 eq) was added, 80mL of ethanol and 80mL of water were added and reacted at 90℃and the progress of the reaction was monitored by HPLC.
The reaction is carried out for 24 hours, HPLC monitoring shows that 1-b is basically reacted completely, the reaction is stopped, the room temperature is reduced, silica gel is adopted, filtrate is washed with water, liquid separation is carried out, filtrate is concentrated until no liquid drops exist, petroleum ether is added, stirring is carried out for 1 hour at 0 ℃, solid is separated out, suction filtration is carried out, a small amount of petroleum ether is washed, and the mixture is dried at 55 ℃.
1-c (25.5 g,144mmol,1.2 eq) and 1-d (36 g,120mmol,1 eq) were dissolved in 300mL toluene under nitrogen, pd (dppf) Cl2 (0.9 g,1.2mmol,1% eq), S-phos (1 g,2.4mmol,2% eq), sodium t-butoxide (15 g,156mmol,1.3 eq) were added and the reaction was refluxed at 110℃and monitored by HPLC.
HPLC monitoring shows that intermediate 1-d is reacted completely, stopping reaction, cooling to room temperature, adding 300mL of water, separating liquid, passing the organic phase through silica gel, concentrating under reduced pressure until no liquid drops exist, boiling in ethanol, cooling, precipitating solid, filtering, and drying.
1-e (38 g,95mmol,1.02 eq) and 1-f (38 g,95mmol,1 eq) were dissolved in 300mL of toluene under nitrogen, pd2 (dba) 3 (0.9 g,1.4mmol,1.5% eq), sodium t-butoxide (12 g,120mmol,1.5 eq) and tri-t-butylphosphine (4 mL,2.85mmol,3% eq) were added and the reaction was refluxed at 110℃in a three-necked flask, and the progress of the reaction was monitored by HPLC.
HPLC monitoring shows that the intermediate 1-f is completely reacted, stopping the reaction, cooling to room temperature, adding 300mL of water, separating liquid, concentrating an organic phase under reduced pressure until no liquid drops exist, boiling in ethanol, cooling, separating out solid, filtering, and recrystallizing toluene and ethanol for 11 times to obtain a target product. Compound 4 (17 g, yield 25%) was finally obtained, HPLC purity 99.92%, ESI-MS (M/z) (M+): theoretical 717.96, observed 717.34, elemental analysis (formula C55H 43N): theoretical value C,92.01; h,6.04; n,1.95; measured value C,92.03; h,6.06; n,1.91.
The following product compounds were obtained in a similar manner:
TABLE 1
The synthetic identification results of the compounds prepared above are shown in table 2 below:
TABLE 2
Example 63:
the synthesis method of the compound 2 is as follows:
63-a (14.22 g,0.084mol,1.03 eq) and 63-b (24.54 g,0.082mol,1 eq) were dissolved in 300mL of toluene under nitrogen protection in a three-necked flask, pd2 (dba) 3 (1.5 g,1.64mmol,2% eq), tri-tert-butylphosphine (5 mL,2.5mmol,3% eq), sodium tert-butoxide (12 g,0.13mol,1.6 eq) were added and the reaction progress was monitored by HPLC.
HPLC monitoring shows that intermediate 63-a is reacted completely, the reaction is stopped, the temperature is reduced, 300mL of water is added, the solution is separated, the organic phase passes through silica gel and anhydrous magnesium sulfate, the organic phase is concentrated under reduced pressure, and the next reaction is carried out directly without purification.
63-c (30 g,77.2mmol,1 eq) and 63-d (32.5 g,81.8mmol,1.06 eq) were dissolved in 300mL toluene under nitrogen, pd2 (dba) 3 (1.4 g,1.55mmol,2% eq), tri-tert-butylphosphine (4.7 mL,2.32mmol,3% eq), sodium tert-butoxide (12 g,0.12mol,1.5 eq) were added and the reaction was refluxed at 110℃and the progress of the reaction was monitored by HPLC.
HPLC monitoring shows that intermediate 63-c is reacted completely, stopping reaction, cooling to room temperature, adding 300mL of water, suction filtering, separating liquid, concentrating an organic phase under reduced pressure by silica gel and anhydrous magnesium sulfate, purifying by a chromatographic column, eluting with PE/MC as eluent, collecting a product, and performing three operations to obtain a final target product. Compound 2 (7.45 g, yield 13.7%) was finally obtained with an HPLC purity of 99.92%, ESI-MS (M/z) (M+): theoretical 703.93, observed 703.45, elemental analysis (formula C54H 41N): theoretical value C,92.14; h,5.87; n,1.99; theoretical value C,92.10; h,5.91; n,1.99.
The following product compounds were obtained in a similar manner:
TABLE 3 Table 3
The synthetic identification results of the compounds prepared above are shown in table 4 below:
TABLE 4 Table 4
Material property testing:
the compounds 1, 2, 3, 4, 7, 12, 13, 19, 22, 28, 31, 40, 41, 42, 43, 49, 52, 67, 72, 79, 88, 100, 102, 106, 118, 120, 121, 139, 196, 197, 198, 202, 205, 208, 209, 210, 217, 223, 224, 226, 253, 256, 262, 264, 265, 274, 277, 283, 295, 297, 301, 305, 313, 316, 322, 393, 394, 400, 412, 418, 420, 430, 433, 439, 451, 457, 469, 478, 490, 499, 511, 519, 529 of the present invention were tested for a thermal weight loss temperature Td and a glass transition temperature Tg, and the test results are shown in table 5 below.
Note that: the thermal weight loss temperature Td is a temperature at which the weight loss is 5% in a nitrogen atmosphere, and is measured on a TGA N-1000 thermogravimetric analyzer with a nitrogen flow of 10mL/min, and a melting point Tg is measured by differential scanning calorimetry (DSC, new DSC N-650) at a heating rate of 10 ℃/min.
Table 5:
from the data, the compound synthesized by the invention has excellent thermal stability, which indicates that the compound conforming to the general structural formula of the invention has excellent thermal stability and can meet the use requirement of the organic electroluminescent material.
Device performance test:
application example 1:
ITO is adopted as the anode substrate material of the reflecting layer, and water, acetone and N are sequentially used 2 Carrying out surface treatment on the surface of the material by plasma;
depositing HT-1 doped with 2% NDP-9 by mass ratio at 10nm on the ITO anode substrate to form a Hole Injection Layer (HIL);
evaporating HT-1 of 100nm above a Hole Injection Layer (HIL) to form a first Hole Transport Layer (HTL);
vacuum evaporating the compound 4 designed by the invention above the first Hole Transport Layer (HTL) to form a second hole transport layer (GPL) with the thickness of 30 nm;
performing co-evaporation on the compound G1 and the compound G2 serving as green light main materials according to the mass ratio of 5:5, and performing evaporation on the compound G1 and the compound G2 serving as doping materials (the GD-1 is 8% of the total mass of the G1 and the G2) to form a light-emitting layer with the thickness of 30nm on a second hole transport layer (GPL);
evaporating HB-1 on the light-emitting layer to obtain a Hole Blocking Layer (HBL) with the thickness of 20 nm;
co-evaporating ET-1 and LiQ on a Hole Blocking Layer (HBL) according to the mass ratio of 5:5 to obtain an Electron Transport Layer (ETL) with the thickness of 30 nm;
mixing and evaporating magnesium (Mg) and silver (Ag) in a mass ratio of 9:1 to form an Electron Injection Layer (EIL) with a thickness of 50nm above an Electron Transport Layer (ETL);
thereafter, silver (Ag) was evaporated over the electron injection layer to form a cathode having a thickness of 100nm, DNTPD having a thickness of 50nm was deposited on the above cathode sealing layer, and in addition, the surface of the cathode was sealed with UV hardening adhesive and a sealing film (seal cap) containing a moisture scavenger to protect the organic electroluminescent device from oxygen or moisture in the atmosphere, so that the organic electroluminescent device was fabricated.
Application examples 2 to 80
The organic electroluminescent devices of application examples 2 to 80 were produced by using the compounds 1, 2, 3, 7, 12, 13, 19, 22, 28, 31, 40, 41, 42, 43, 49, 52, 67, 72, 79, 88, 100, 102, 106, 118, 120, 121, 139, 196, 197, 198, 202, 205, 208, 209, 210, 217, 223, 224, 226, 253, 256, 262, 264, 265, 274, 277, 283, 295, 297, 301, 305, 313, 316, 322, 393, 394, 400, 412, 418, 420, 430, 433, 439, 451, 457, 469, 478, 490, 499, 511, 519, 529 of the examples 2 to 80, respectively, as the second hole transporting materials, and the other portions were the same as those of application example 1.
Comparative examples 1 to 3:
the difference from application example 1 is that the compound 4 in this application was replaced with A-40, A-50, A-53, compound 7, and compound 8 in CN111635323B, respectively, as the second hole transporting material, and the remainder was the same as application example 1.
The organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the comparative example were characterized in that the current density was 10mA/cm 2 The results of the measurement under the conditions of (2) are shown in Table 6.
Table 6:
as can be seen from the above Table 6, the compound of the present invention is applied to an organic electroluminescent device, and the luminous efficiency is greatly improved under the same current density, the starting voltage of the device is reduced, the power consumption of the device is relatively reduced, and the service life of the device is correspondingly improved.
The organic electroluminescent devices prepared in comparative examples 1 to 3, application examples 1 to 8, and application examples 63 to 70 were subjected to luminescence lifetime test, respectively, to obtain luminescence lifetime T97% data (time for which luminescence luminance was reduced to 97% of initial luminance), and the test equipment was a TEO luminescent device lifetime test system. The results are shown in Table 7:
table 7:
as can be seen from the above Table 7, the application of the compound of the present invention to organic electroluminescent devices has a greatly improved service life at the same current density, and has a wide application prospect.
Claims (10)
1. A spiro compound with a structure shown in a formula 1 is characterized in that,
wherein, the liquid crystal display device comprises a liquid crystal display device,
R 1 and R is R 3 Linking to make R 1 -C-R 3 Cycloalkyl groups constituting C3-C20 or cycloalkenyl groups constituting C3-C20;
R 2 the following groups selected from deuterium or deuterated or non-deuterated: one or more of C1-C10 alkyl, C3-C10 cycloalkyl, C6-C20 aromatic group, or C1-C10 alkyl substituted C6-C20 aromatic group;
n is an integer of 0 to 5.
2. The compound of claim 1, wherein R 1 -C-R 3 Cycloalkyl groups constituting C3-C12 or cycloalkenyl groups constituting C3-C12; r is R 2 The following groups, which are deuterated or non-deuterated: C1-C4 alkyl, phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, 9-dimethylfluorenyl.
3. The compound of claim 2, wherein R 1 -C-R 3 Cycloalkyl constituting C3-C10; r is R 2 The following groups, which are deuterated or non-deuterated: one or more of methyl, ethyl, propyl, phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, 9-dimethylfluorenyl.
4. The compound of claim 2, wherein R 1 -C-R 3 Constituting cyclopropane, cyclobutane, cyclopentane or cyclohexane; r is R 2 Methyl, ethyl, propyl, deuterated methyl, deuterated ethyl or deuterated propyl, n is an integer from 0 to 3.
5. The compound of claim 1, having the structural formula 2-4:
in the formulae 2 to 4, R 1 And R is R 3 Linking to make R 1 -C-R 3 Cycloalkyl groups constituting C3-C20.
6. The compound of claim 1, wherein the compound is any one of the following:
7. an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises the compound according to any one of claims 1 to 6.
8. The organic electroluminescent device of claim 7, wherein the organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer; at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the compound according to any one of claims 1 to 5, and in particular, the hole transport layer contains the compound according to any one of claims 1 to 5.
9. An electronic display device comprising the organic electroluminescent device as claimed in claim 7.
10. An OLED lighting device comprising the organic electroluminescent device as claimed in claim 7.
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| CN113045434A (en) * | 2021-03-03 | 2021-06-29 | 陕西莱特光电材料股份有限公司 | Organic compound, and organic electroluminescent device and electronic device using same |
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| CN113045434A (en) * | 2021-03-03 | 2021-06-29 | 陕西莱特光电材料股份有限公司 | Organic compound, and organic electroluminescent device and electronic device using same |
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