CN116332828A - Dibenzocycloheptanone derivatives and application thereof in OLED (organic light emitting diode) device - Google Patents
Dibenzocycloheptanone derivatives and application thereof in OLED (organic light emitting diode) device Download PDFInfo
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- ORJNLUXHBUSOKL-UHFFFAOYSA-N 6,7-dihydrodibenzo[2,1-b:1',2'-d][7]annulen-5-one Chemical class O=C1CCC2=CC=CC=C2C2=CC=CC=C12 ORJNLUXHBUSOKL-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 66
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 claims description 11
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
- -1 tri-tert-butyl phosphine tetrafluoroborate Chemical compound 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000005525 hole transport Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 150000003997 cyclic ketones Chemical class 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000012300 argon atmosphere Substances 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 230000000877 morphologic effect Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- 238000001816 cooling Methods 0.000 claims 1
- 238000011056 performance test Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000000967 suction filtration Methods 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 10
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 10
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 7
- 238000000295 emission spectrum Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
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- HNACKJNPFWWEKI-UHFFFAOYSA-N 3,6-dimethyl-9h-carbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC=C3NC2=C1 HNACKJNPFWWEKI-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NDGSHOQCFOWVIW-UHFFFAOYSA-N (2-bromo-4-methylphenyl)-phenylmethanone Chemical compound BrC1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 NDGSHOQCFOWVIW-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
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Abstract
The invention relates to the field of organic electroluminescent materials, in particular to a novel main molecular structure taking dibenzocycloheptanone as a core and application thereof in an organic electroluminescent display device. The molecular structure of the dibenzocycloheptanone main body is shown as the formula (1) and the formula (2):
Description
Technical Field
The invention relates to the field of organic electroluminescent materials (OLEDs), in particular to a novel main material structure taking dibenzocycloheptanone as a core and application of the material in an organic electroluminescent display device.
Background
Organic Light-Emitting diodes (OLEDs), also known as Organic electroluminescent displays, organic semiconductors, have the characteristics of low energy consumption, wide viewing angle, gorgeous color, flexibility, etc., and have been attracting attention in the academic and industrial circles as a new technology in the fields of display and illumination. The last 50 years of the century, a.bernanose et al, showed the first electroluminescent phenomenon historically, but did not receive attention. Until 1987, deng Qingyun et al prepared the first organic electroluminescent device, from which the technological trend of OLED research was raised worldwide. Phosphorescent organic light emitting devices (PhOLEDs) are one type of Organic Light Emitting Diode (OLED), in which phosphorescent light emitting molecules can capture singlet and triplet excitons simultaneously, so that their external quantum efficiency and luminous efficiency are 4 times that of conventional fluorescent OLED materials, and the efficiency of the device is greatly improved. In general, pholeds rely on the device configuration of the host-guest doped light emitting layer to achieve an increase in efficiency. In the light-emitting layer of the PhOLED device, the content of general phosphorescent guest molecules is low, and host molecules which are dominant in the host direction influence and determine the physical properties of the light-emitting layer to a great extent, and directly influence the performance of the light-emitting device.
Besides good carrier transport performance and capability of forming a pinhole-free film, the main material of the excellent PhOLED device needs to have the following properties: 1. the HOMO/LUMO energy level of the host material enables efficient embedding of the HOMO/LUMO energy level of the dopant material. 2. The emission spectrum of the main material and the absorption spectrum of the doped material can be effectively overlapped, and the energy transfer is facilitated. 3. The host material needs to have a high triplet energy level to prevent the reverse transfer of triplet energy from the dopant material to the host material. 4. The transport of positive and negative carriers in the host material should reach a certain balance to confine the exciton recombination zone in the device light-emitting layer. 5. The host material has a HOMO/LUMO energy level that matches the adjacent hole transport layer, the electron transport layer energy level to reduce the injection barrier and thus the device start-up voltage. Thus, the development of new host materials that can accommodate the above requirements is faced with a great challenge.
Disclosure of Invention
The invention aims to provide a novel main body material taking dibenzocycloheptanone as a core.
The novel main body material taking dibenzocycloheptanone as a core has the structures shown in the formulas (1) and (2):
ar in the formula (1) and the formula (2) 1 And Ar is a group 2 Respectively the same or different, m is represented by Ar 1 N is represented by Ar 2 M and n are independently selected from 0, 1, 2,3 or 4, respectively.
In the formula (1) and the formula (2), the substituent R 1 Are respectively the same or different and are independently selected from hydrogen, heavy hydrogen and C 3-10 Cyclic ketones, C 1-10 Alkyl, C 1-10 Alkenyl, C 1-10 Alkynyl, C substituted or unsubstituted by hydrogen, deuterium, halogen, alkyl, alkoxy, benzyl, ester, amide, carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano 6-20 Any one of aryl, heteroaryl or arylamino groups.
Ar in the formula (1) and the formula (2) 1 And Ar is a group 2 Respectively and independently represent-R 2 -Ar-R 3 、-R 2 -Ar、- Ar-R 3 or-R 3 The method comprises the steps of carrying out a first treatment on the surface of the Ar represents C substituted or unsubstituted by hydrogen, deuterium, halogen, alkyl, alkoxy, benzyl, ester, amide, carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano 6-20 An aryl group; r is R 3 Are each identical or different and are each independently selected as hydrogen atom, heavy hydrogen atom, C substituted or unsubstituted by hydrogen, heavy hydrogen, halogen, alkyl, alkoxy, benzyl, ester, amide, carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano 3-10 Cyclic ketones, C 1-10 Alkyl, C 1-10 Alkenyl, C 6-20 Aryl, C 6-20 Heteroaryl, a structure represented by formula (3) or formula (4), and at least comprises a structure represented by formula (3) or formula (4):
in the formula (3) and the formula (4), X represents an oxygen atom, a sulfur atom, a selenium atom, C 1-10 Straight-chain or branched-chain substituted or unsubstituted alkylene, C 6-20 Aryl-substituted alkylene, C 1-10 One of the tertiary amino groups substituted with an alkyl or aryl group; r is R 4 And are each the same or different and are each independently selected from hydrogen, deuterium, any of alkyl, aryl, heteroaryl or arylamino groups having 10 or less carbon atoms substituted or unsubstituted with hydrogen, deuterium, halogen, alkyl, alkoxy, benzyl, ester, amide, carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano.
Preferably, the molecular structure in formula (1) and formula (2) includes, but is not limited to, the following structural formula:
the second object of the present invention is to provide a method for preparing the organic electroluminescent host material, wherein the reaction equation generated in the preparation process is as follows:
in the reaction equation (1), Y 1 、Y 2 Each independently represents a chlorine atom, a bromine atom or an iodine atom; the number is independently selected from 0, 1, 2,3 or 4.
Wherein the specific reaction steps of the reaction equation 1 are as follows: in nitrogen or argon atmosphere, taking halogenated compound with dibenzocycloheptanone as core and R 5 H, palladium acetate, tri-tert-butyl phosphine tetrafluoroborate and sodium tert-butoxide are placed in toluene solution, the mixed solution of the reactants is placed at the reaction temperature of 80-150 ℃ for 6-24 hours, and then cooled, filtered by diatomite in a suction way, and reducedAnd (5) performing pressure spin drying and silica gel column chromatography to obtain a target product.
The halogenated compound with dibenzocycloheptanone as a core comprises: r is R 3 H: palladium acetate: tri-tert-butylphosphine tetrafluoroborate: the molar ratio of the sodium tert-butoxide is 1 (0.01-10): (0.01-1): (0.01-10): (0.01-20).
The third object of the present invention is to apply the novel host molecules with dibenzocycloheptanone as the core to the manufacture of organic electroluminescent devices, which is characterized in that the organic electroluminescent devices with phosphorescent materials as the luminescent materials sequentially comprise an ITO conductive glass substrate (anode), a hole transport layer, an electron blocking layer, a luminescent layer (Flrpic as blue phosphorescent materials, ir (ppy)) from bottom to top 2 (acac) as green phosphorescent material, ir (mphmq) 2 (tmd) as a red phosphorescent material, the organic electroluminescent host material according to the present invention, an electron transport layer, an electron injection layer, and a cathode layer.
The organic electroluminescent device is prepared by adopting a vacuum evaporation method, and the molecular structural formula of an organic compound used in the device is as follows:
the beneficial effects of the invention are as follows:
the novel main body material molecule taking the dibenzocycloheptanone as the core has good thermal stability and photoelectric property, and HOMO and LUMO energy levels are easy to prepare, so that the novel main body material molecule is suitable for various luminescent materials and has good photoelectric property.
The novel main material molecule taking the dibenzocycloheptanone as the core can achieve good balance of positive and negative carrier transportation, so that an exciton recombination region is effectively limited in a device luminous layer, the exciton utilization rate is further improved, and lower driving voltage is displayed.
The novel host material molecule taking the dibenzocycloheptanone as the core provided by the invention has higher triplet state energy level and can be used as the host material of blue, green and red phosphorescence OLEDs.
The main body material manufactured by the method is used for manufacturing the OLEDs, has good device performance, realizes high device efficiency and low efficiency roll-off, and has good industrialized application prospect.
The novel main body material molecule taking the dibenzocycloheptanone as the core provides a novel design thought for designing a seven-membered ring structure and constructing a main body material with a non-traditional structure by using the novel main body material molecule.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of Compound A1.
FIG. 2 is a nuclear magnetic carbon spectrum of the compound A1.
FIG. 3 is a nuclear magnetic hydrogen spectrum of Compound A2.
FIG. 4 is a nuclear magnetic carbon spectrum of Compound A2.
FIG. 5 is a nuclear magnetic hydrogen spectrum of Compound B.
FIG. 6 is a nuclear magnetic carbon spectrum of Compound B.
FIG. 7 is DSC of Compound A1.
FIG. 8 is DSC of Compound A2.
FIG. 9 is DSC of Compound B.
Fig. 10 is a schematic diagram of the structure of a hole transport device and an electron transport device mainly composed of A1, A2, and B.
Fig. 11 shows the results of testing the hole transporting device and the electron transporting device mainly comprising A1, A2, and B, wherein (a), (B), and (c) correspond to A1, A2, and B, respectively.
FIG. 12 is a schematic diagram showing the structure of an organic electroluminescent device prepared from A1, A2, and B as host materials, wherein (a) is a blue phosphorescent device structure using Flrpic as a light-emitting material, and (B) is Ir (ppy) 2 (acac) is a green phosphorescent device structure of luminescent material, (c) is Ir (mphmq) 2 (tmd) is a red phosphorescent device structure of a luminescent material.
FIG. 13 shows the results of tests of organic electroluminescent devices prepared from A1, A2, and B as main materials, wherein (a) is the result of test of blue phosphorescent device with Flrpic as luminescent material, and (B) is the result of test of blue phosphorescent device with Flrpic as luminescent material Ir(ppy) 2 (acac) results of testing green phosphorescent devices as luminescent materials, (c) Ir (mphmq) 2 (tmd) is the red phosphor device test result of the luminescent material.
FIG. 14 shows the Electroluminescence (EL) emission spectra of an organic electroluminescent device prepared from A1, A2, and B as the host materials, wherein (a) is the Electroluminescence (EL) emission spectrum of a blue phosphorescent device using Flrpic as the luminescent material, and (B) is Ir (ppy) 2 (acac) Electroluminescent (EL) emission spectrum of green phosphorescent device using luminescent material, (c) Ir (mphmq) 2 (tmd) is the Electroluminescent (EL) emission spectrum of a red phosphorescent device of a luminescent material.
Detailed Description
For a better understanding of the present invention, the present invention is explained below in conjunction with specific examples, which are not intended to limit the scope of the present invention.
Example 1: preparation of formula I, exemplified by Compound A1 (MeCz-EtBP)
To a two-necked flask with a magnetic stirrer was added 2-bromo-4-methyldibenzosuberone (600.0 mg,2.0 mmol), 3, 6-dimethylcarbazole (410.0 mg,2.1mmol,1.05 equiv), palladium acetate (22.4 mg,0.1mmol,5.0 mol%), tri-tert-butylphosphine tetrafluoroborate (116.0mg,0.4mmol,20.0 mol%), sodium t-butoxide (384.4 mg,4.0mmol,2.0 equiv) and toluene (30 mL) under a nitrogen atmosphere. The resulting mixture was stirred at 100℃for 10 hours. After it has cooled to room temperature, it is treated with 10-20mL CH 2 Cl 2 The filtrate was diluted and filtered through celite, concentrated in vacuo and the residue purified by silica gel column chromatography (petroleum ether/dichloromethane=2/1, v/v) to give 772.3mg of the desired product A1 in 93% yield. The melting point is 199.5-200.5 ℃. 1 H NMR(400MHz,CDCl 3 ):δ＝7.95(d,J＝8.0Hz,1H),7.89(s,2H),7.47 (t,J＝8.8Hz,1H),7.39-7.31(m,4H),7.26-7.20(m,4H),3.36-3.33(m,2H),3.18-3.16 (m,2H),2.54(s,6H),2.42(s,3H)ppm. 13 C NMR(100MHz,CDCl 3 ):δ＝200.3,141.3, 140.8,139.8,139.6,139.1,139.0,138.3,132.4,130.7,129.8,129.5,127.3,127.1,126.7, 123.7,123.0,120.4,109.6,35.2,33.0,21.5,20.2ppm.HRMS(ESI + ) Calculated value C 30 H 25 NO[M+H] + 416.2009, found 416.2006. A1 is shown in figure 1, and A1 is shown in figure 2.
Example 2: preparation of formula I, exemplified by Compound A2 (DMAC-EtBP)
To a two-necked flask with a magnetic stirrer was added 2-bromo-4-methyldibenzosuberone (600.0 mg,2.0 mmol), 9-dimethylacridine (439.2 mg,2.1mmol,1.05 equiv), palladium acetate (22.4 mg,0.1mmol,5.0 mol%), tri-tert-butylphosphine tetrafluoroborate (116.0mg,0.4mmol,20.0 mol%), sodium t-butoxide (384.4 mg,4.0mmol,2.0 equiv) and toluene (30 mL) under a nitrogen atmosphere. The resulting mixture was stirred at 100℃for 10 hours. After it has cooled to room temperature, it is treated with 10-20mL CH 2 Cl 2 The filtrate was diluted and filtered through celite, concentrated in vacuo and the residue purified by silica gel column chromatography (petroleum ether/dichloromethane=3/1, v/v) to give 815.4mg of the desired product A2 in 95% yield. The melting point is 244.5-245.5 ℃. 1 H NMR(400MHz,CDCl 3 ):δ＝7.94(d,J＝7.6Hz,1H),7.51-7.44(m,3H),7.37(t,J ＝7.6Hz,1H),7.26(overlay,1H),7.10(s,1H),7.06(s,1H),7.0-6.91(m,4H),6.31(d, J＝8.0Hz,2H)3.34-3.31(m,2H),3.16-3.13(m,2H),2.38(s,3H),1.69(s,6H)ppm. 13 C NMR(100MHz,CDCl 3 ) Delta= 200.8,142.6,141.9,141.3,141.2,140.6,139.2,139.0, 132.5,131.9,130.8,130.1,129.8,127.7,126.7,126.5,125.5,120.8,114.2,36.1,35.3, 32.8,31.6,20.0ppm. Hrms (esi+) 31 H 27 NO[M+H] + 430.2165, found 430.2160. A2 is shown in FIG. 3, and A2 is shown in FIG. 4.
Example 3: preparation of Compound B (MeCz-BP)
To a two-necked flask with a magnetic stirrer was added 2-bromo-4-methylbenzophenone (548.0 mg,2.0 mmol), 3, 6-dimethylcarbazole (410.0 mg,2.1mmol,1.05 equiv), palladium acetate (22.4 mg,0.1mmol,5.0 mol%), tri-tert-butylphosphine tetrafluoroborate (116.0 mg,0.4mmol,20.0 mol%), sodium t-butoxide (384.4 mg,4.0mmol,2.0 equiv) and toluene (30 mL) under a nitrogen atmosphere. The resulting mixture was stirred at 100℃for 10 hours. After it has cooled to room temperature, it is treated with 10-20mL CH 2 Cl 2 The residue was diluted and filtered through celite, concentrated in vacuo and purified by silica gel column chromatography (petroleum ether/dichloromethane=4/1, v/v) to give 715.8mg of the desired product B in 92% yield. The melting point is 216.5-217.5 ℃. 1 H NMR(400MHz,CDCl 3 ):δ＝7.93-7.90(m,4H),7.64(t,J＝7.2Hz,1H),7.57-7.51(m, 4H),7.46(d,J＝8.4Hz,1H),7.41(d,J＝8.0Hz,2H),7.24(d,J＝8.4Hz,2H),2.56(s, 6H),2.46(s,3H)ppm. 13 C NMR(100MHz,CDCl 3 ):δ＝198.0,140.2,139.5,139.1, 137.9,137.0,133.4,130.6,130.3,129.7,128.9,128.7,127.3,123.8,123.2,120.4,109.7, 21.5,20.5ppm.HRMS(ESI + ) Calculated value C 28 H 28 NO[M+H] + 390.1852, observed 390.1848 ppm. B nuclear magnetic hydrogen spectrum, see FIG. 5, and B nuclear magnetic carbon spectrum, see FIG. 6.
The invention selects the compounds A1, A2 and B as main materials to manufacture the organic electroluminescent device, wherein B is used as a comparative example. Commercially available phosphorescent materials are used as luminescent materials. It should be understood that the implementation process and the result of the device are only used for better explaining the present invention, and are not limiting to the present invention.
The organic phosphorescent electroluminescent device was prepared as follows:
1. cleaning ITO (indium tin oxide) glass: washing with alkali and deionized water in sequence until the surface is neither converged into water drops nor flows down in a stranding manner, and treating in a plasma cleaner for 10 minutes after drying;
2. sequentially vacuum evaporating a hole transport layer TAPC (30 nm), an electron blocking layer TCTA (10 nm) and an evaporation rate of 0.1nm/s on anode ITO glass;
3. vacuum evaporating the co-evaporating luminescent layer on the electron blocking layer, wherein the evaporating rate is 0.1nm/s;
4. vacuum evaporating an electron transport layer TmPyPB (45 nm) on the light emitting layer, wherein the evaporation rate is 0.1nm/s;
5. vacuum evaporating LiF (0.8 nm) on the electron transport layer, wherein the evaporating speed is 0.08nm/s;
6. cathode Al (100 nm) was vacuum evaporated on top of the electron injection layer at a deposition rate of 0.1nm/s.
Blue light example 1: ITO/TAPC (30 nm)/TCTA (10 nm)/22 wt% Flrpic A1 (20 nm)/TmPyPB (45 nm)/LiF (0.8 nm)/Al (100 nm);
blue light example 2: ITO/TAPC (30 nm)/TCTA (10 nm)/22 wt% Flrpic A2 (20 nm)/TmPyPB (45 nm)/LiF (0.8 nm)/Al (100 nm);
blue light example 3: ITO/TAPC (30 nm)/TCTA (10 nm)/22 wt% Flrpic B (20 nm)/TmPyPB (45 nm)/LiF (0.8 nm)/Al (100 nm);
green light example 1: ITO/TAPC (30 nm)/TCTA (10 nm)/7 wt% Ir (ppy) 2 (acac):A1 (20nm)/TmPyPB(45nm)/LiF(0.8nm)/Al(100nm)；
Green light example 2: ITO/TAPC (30 nm)/TCTA (10 nm)/7 wt% Ir (ppy) 2 (acac):A2 (20nm)/TmPyPB(45nm)/LiF(0.8nm)/Al(100nm)；
Green light example 3: ITO/TAPC (30 nm)/TCTA (10 nm)/7 wt% Ir (ppy) 2 (acac):B (20nm)/TmPyPB(45nm)/LiF(0.8nm)/Al(100nm)；
Red light example 1: ITO/TAPC (30 nm)/TCTA (10 nm)/2 wt% Ir (mphmq) 2 (tmd): A1(20nm)/A1(10nm)/TmPyPB(45nm)/LiF(0.8nm)/Al(100nm)；
Red light example 2: ITO/TAPC (30 nm)/TCTA (10 nm)/2 wt% Ir (mphmq) 2 (tmd): A2(20nm)/A2(10nm)/TmPyPB(45nm)/LiF(0.8nm)/Al(100nm)；
Red light example 3: ITO/TAPC (30 nm)/TCTA (10 nm)/2 wt% Ir (mphmq) 2 (tmd): B(20nm)/B(10nm)/TmPyPB(45nm)/LiF(0.8nm)/Al(100nm)；
The test results of the devices are shown in tables 1 and 2
TABLE 1
TABLE 2
Table 1 data annotation: a) The brightness is 1000cd m -2 Fluorescence emission peak at that time; b) Half-width; c) CIE coordinates of the emission spectrum of the device.
Table 2 data annotation: d) Brightness of 1cd m -2 Is set to the driving voltage of (a); e) Maximum external quantum efficiency; f) And (5) power efficiency.
For comparison, compound B was used as a reference in the present invention. As can be seen from fig. 11, 12 and 13, the DSC of the inventive products A1 and A2 is far higher than that of the comparative molecule B, which indicates that the inventive products have good morphological stability, and have better film forming property and are easier to form amorphous film in the device manufacturing process, so as to effectively avoid trap generation.
As can be seen from fig. 14 and table 1, all devices showed the same Electroluminescent (EL) emission spectrum, indicating that there was sufficient energy transfer from the host material to the luminescent material.
As can be seen from table 2, in the blue, green, and red devices, the actuation voltages of A1 and A2 are smaller as a whole than comparative example B, and A1 and A2 can obtain higher external quantum efficiency while ensuring lower efficiency roll-off.
The organic phosphorescence electroluminescent device prepared based on the material of the invention has better device performance, the maximum power efficiency is 93.4lm/W, the maximum External Quantum Efficiency (EQE) is 28.1 percent, and compared with the comparison device B, the device has excellent characteristics in the aspects of current efficiency, hole and electron transmission matching, device efficiency and the like.
The foregoing is only a few embodiments of the present invention, and the present invention is not limited to the above embodiments, but can be modified, replaced, etc. within the spirit and principle of the present invention.
While the invention has been disclosed by way of examples and preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. On the contrary, it is to be understood by those skilled in the art that various modifications and similar arrangements are intended to be covered. The scope of the appended claims is, therefore, to be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements.
Claims (6)
1. The structure of a novel organic electroluminescent main material with dibenzocycloheptanone as a core and the application of the material in an organic electroluminescent display device are shown in the following formula (1) and formula (2):
ar in the formula (1) and the formula (2) 1 And Ar is a group 2 Respectively the same or different, m is represented by Ar 1 N is represented by Ar 2 M and n are independently selected from 0, 1, 2,3 or 4;
in the formula (1) and the formula (2), the substituent R 1 Are respectively the same or different and are independently selected from hydrogen, heavy hydrogen and C 3-10 Cyclic ketones, C 1-10 Alkyl, C 1-10 Alkenyl, C 1-10 Alkynyl, C substituted or unsubstituted by hydrogen, deuterium, halogen, alkyl, alkoxy, benzyl, ester, amide, carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano 6-20 Any one of aryl, heteroaryl or arylamino groups;
ar in the formula (1) and the formula (2) 1 And Ar is a group 2 Respectively and independently represent-R 2 -Ar-R 3 、-R 2 -Ar、-Ar-R 3 or-R 3 The method comprises the steps of carrying out a first treatment on the surface of the Ar represents C substituted or unsubstituted by hydrogen, deuterium, halogen, alkyl, alkoxy, benzyl, ester, amide, carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano 6-20 An aryl group; r is R 3 Are respectively identical or different and are selected as hydrogen atoms, heavy hydrogen atoms, by hydrogen, heavy hydrogen, halogen, alkyl, alkoxy, benzyl, ester, amide, amino, or the like,Carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano-substituted or unsubstituted C 3-10 Cyclic ketones, C 1-10 Alkyl, C 1-10 Alkenyl, C 6-20 Aryl, C 6-20 Heteroaryl, a structure represented by formula (3) or formula (4), and at least comprises a structure represented by formula (3) or formula (4):
in the formula (3) and the formula (4), X represents an oxygen atom, a sulfur atom, a selenium atom, C 1-10 Straight-chain or branched-chain substituted or unsubstituted alkylene, C 6-20 Aryl-substituted alkylene, C 1-10 One of the tertiary amino groups substituted with an alkyl or aryl group; r is R 4 And are each the same or different and are each independently selected from hydrogen, deuterium, any of alkyl, aryl, heteroaryl or arylamino groups having 10 or less carbon atoms substituted or unsubstituted with hydrogen, deuterium, halogen, alkyl, alkoxy, benzyl, ester, amide, carbonyl, aldehyde, alkylamino, carbonyl, nitro, cyano.
2. A novel electroluminescent host material based on dibenzocycloheptanone as claimed in claim 1, wherein the specific structure of formula (1) and formula (2) includes, but is not limited to:
3. An organic electroluminescent device comprising the compound according to any one of claims 1 and 2, characterized in that the compound is used as a host material for a light emitting layer for fabricating OLEDs devices.
4. A process for the preparation of a compound according to any one of claims 1 to 3, characterized in that the reaction equation occurring during the preparation is:
in the reaction equation (1), Y 1 、Y 2 Each independently represents a chlorine atom, a bromine atom or an iodine atom; the number is respectively and independently selected from 0, 1, 2,3 or 4;
wherein the specific reaction steps of the reaction equation 1 are as follows: in nitrogen or argon atmosphere, taking halogenated compound with dibenzocycloheptanone as core and R 5 H, palladium acetate, tri-tert-butyl phosphine tetrafluoroborate and sodium tert-butoxide are placed in toluene solution, the mixed solution of the reactants is placed at the reaction temperature of 80-150 ℃ for 6-24 hours, and then the target product is obtained after cooling, suction filtration by diatomite, reduced pressure spin drying and silica gel column chromatography;
the halogenated compound with dibenzocycloheptanone as a core comprises: r is R 3 H: palladium acetate: tri-tert-butylphosphine tetrafluoroborate: the molar ratio of the sodium tert-butoxide is 1 (0.01-10): (0.01-1): (0.01-10): (0.01-20).
5. The method for manufacturing an organic electroluminescent device by using a novel host molecule with dibenzocycloheptanone as a core according to any one of claims 1-3, wherein the organic electroluminescent device with phosphorescent material comprises an ITO conductive glass substrate (anode), a hole transport layer (TAPC), an electron blocking layer (TCTA), and a luminescent layer (Flrpic as blue phosphorescent material, ir (ppy)) sequentially from bottom to top 2 (acac) as green phosphorescent material, ir (mphmq) 2 (tmd) as a red phosphorescent material, the organic electroluminescent host material according to the present invention, an electron transport layer (TmPyPB), an electron injection Layer (LiF), and a cathode layer (Al), respectively.
6. The performance test of phosphorescent organic electroluminescent device prepared from novel host material molecules with dibenzocycloheptanone as a core according to claim 5, wherein the phosphorescent organic electroluminescent device has higher triplet energy level, lower driving voltage, coordinated matching of hole and electron transmission, good morphological stability, good device performance, and high device efficiency and low roll-off efficiency.
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