CN114031609A - Compound containing carbazole and quinazoline structure and application thereof - Google Patents
Compound containing carbazole and quinazoline structure and application thereof Download PDFInfo
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- CN114031609A CN114031609A CN202111527906.5A CN202111527906A CN114031609A CN 114031609 A CN114031609 A CN 114031609A CN 202111527906 A CN202111527906 A CN 202111527906A CN 114031609 A CN114031609 A CN 114031609A
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- compound
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- carbazole
- quinazoline
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims description 79
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 36
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 22
- -1 1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 6-dimethyl-1, 4-phenylene, monofluoro-1, 4-phenylene, difluoro-1, 4-phenylene, trifluoro-1, 4-phenylene Chemical group 0.000 claims description 21
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 230000005525 hole transport Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- SUYCTEJBRSFZCD-UHFFFAOYSA-N 9h-carbazole;quinazoline Chemical compound N1=CN=CC2=CC=CC=C21.C1=CC=C2C3=CC=CC=C3NC2=C1 SUYCTEJBRSFZCD-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims 7
- 239000002346 layers by function Substances 0.000 claims 3
- 230000000903 blocking effect Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- 229910052757 nitrogen Inorganic materials 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 238000010626 work up procedure Methods 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 5
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 4
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 4
- ZBUBNEPKTKCYLU-UHFFFAOYSA-N 3-bromo-5-fluoro-9H-carbazole Chemical compound FC1=CC=CC2=C1C1=CC(Br)=CC=C1N2 ZBUBNEPKTKCYLU-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 4
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 1
- XKBDPCKDSHRUDX-UHFFFAOYSA-N 2-chloro-4-(4-methylphenyl)quinazoline Chemical compound C1=CC(C)=CC=C1C1=NC(Cl)=NC2=CC=CC=C12 XKBDPCKDSHRUDX-UHFFFAOYSA-N 0.000 description 1
- RODQKGBYDIAMCF-UHFFFAOYSA-N 3-bromo-9-(4-methylphenyl)carbazole Chemical compound C1=CC(C)=CC=C1N1C2=CC=C(Br)C=C2C2=CC=CC=C21 RODQKGBYDIAMCF-UHFFFAOYSA-N 0.000 description 1
- 244000286893 Aspalathus contaminatus Species 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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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)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of organic electroluminescent display, and particularly discloses a compound containing carbazole and quinazoline structures, which is remarkably improved in the aspects of the luminous service life and the luminous efficiency of a device, and also discloses application of the compound in an organic electroluminescent device. The compound containing carbazole and quinazoline structure has the following structure. The electroluminescent device prepared by the compound of the invention has the advantages of high purity, high brightness and high efficiency.
Description
Technical Field
The invention relates to the technical field of OLED compounds, in particular to a novel carbazole and quinazoline containing compound, and also relates to an application thereof.
Background
Since the 60's of the 20 th century, Pope et al first reported the phenomenon of electroluminescence of anthracene single crystals, and opened the introduction to the research of organic light emitting devices, but did not gain extensive attention because the brightness and efficiency obtained at that time were not ideal.
In 1987, Rooibos Deng cloud of Kodak, USA reported that a multilayer device containing an electron hole transport layer is prepared by vacuum evaporation method, and brightness of more than 1000cd/m is obtained2And a light emitting device having an efficiency of more than 1.5lm/W and a driving voltage of less than 10V, which has advantages of lightness and thinness, low driving voltage, self-luminescence, wide viewing angle, fast response, and the like, and thus has received much attention. The research promotes the research of organic light-emitting display devices, and reports of devices with wider application and more excellent performance are continuously emerging.
In recent years, OLED display devices are developed more and more rapidly, and different types of OLED display devices, such as vehicle-mounted small OLED display devices, portable intelligent wearable OLED display devices, ultra-thin OLED display devices, and the like, are also appeared.
Along with the improvement of the living standard of people, the requirements on the performance of the display are continuously improved. In order to save energy and accord with the sustainable development of the state, the display with low energy consumption is favored by people. Therefore, development of a display with a low driving voltage has been a hot spot.
Disclosure of Invention
The invention aims to develop an organic electroluminescent material which is applied to an OLED device, can improve the current efficiency of the device and reduce the driving voltage.
In a first aspect, the present invention provides a compound containing carbazole and quinazoline structure, having a structure shown in general formula (I):
in the formula (I), R1、R2Represents a single substitution toA substituent group having a maximum allowable number of substitutions;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13and R14The substituent groups are respectively and independently selected from one of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C40 monocyclic aryl or polycyclic aryl, and the substituent groups are respectively and independently selected from one of halogen, C1-C10 chain alkyl, C6-C30 aryl and C3-C30 heteroaryl; and R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14Not hydrogen at the same time;
A1and A2The aryl group is respectively and independently selected from substituted or unsubstituted C6-C60 arylene, and the substituent groups are respectively and independently selected from one of halogen, C1-C20 chain alkyl and C3-C20 cycloalkyl.
As a preferred embodiment of the present invention, said A is1And A2Each independently selected from 1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 6-dimethyl-1, 4-phenylene, monofluoro-1, 4-phenylene, difluoro-1, 4-phenylene, trifluoro-1, 4-phenylene, and tetrafluoro-1, 4-phenylene.
As a preferred embodiment of the present invention, said R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14The substituent groups are respectively and independently selected from one of halogen, chain alkyl of C1-C5, aryl of C6-C30 and heteroaryl of C3-C30.
It is preferable thatSaid R is1、R2At least one of which is selected from one of methyl, fluorine atom, methyl-substituted phenyl, methyl-substituted biphenyl, fluorine-substituted phenyl, fluorine-substituted biphenyl.
In a preferred embodiment of the present invention, the carbazole-and quinazoline-containing compound is selected from the group consisting of the structures represented by any one of the following general formulae I-1 to I-4:
wherein, in the general formula I-1 to the formula I-4, R1、R2A substituent group representing mono-substitution to the maximum allowable number of substitution; r1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14Is as defined in formula I.
Preferably, in the general formula I-1 to formula I-4, R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14The substituent groups are respectively and independently selected from one of halogen, chain alkyl of C1-C5, aryl of C6-C30 and heteroaryl of C3-C30. More preferably, R is1、R2At least one of which is selected from one of methyl, fluorine atom, methyl-substituted phenyl, methyl-substituted biphenyl, fluorine-substituted phenyl, fluorine-substituted biphenyl.
In the present specification, the expression of Ca to Cb means that the group has carbon atoms of a to b unless otherwise specified. Each group in the present specification has a substituent, and the carbon number thereof does not include the carbon number of the substituent.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present specification, the expression of chemical elements includes the concept of chemically identical isotopes, for example, hydrogen (H) includes 1H (protium or H), 2H (deuterium or D), and the like; carbon (C) includes 12C, 13C, etc.
In the present specification, the halogen atom is F, Cl, Br or I.
In the present specification, the substituted or unsubstituted chain alkyl group includes a straight-chain alkyl group and an alkyl group containing a branched chain. Straight chain alkyl refers to straight chain alkyl of the general formula CnH2n +1-, including but not limited to methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like. Preferably, n is a linear alkyl group of 1-5. Branched chain-containing alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and the like. The preferred branched alkyl group has 1 to 5 carbon atoms.
In the present specification, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and the like. Cycloalkyl groups having 3 to 6 carbon atoms are preferable.
In the present specification, the monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in the monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of C6 to C40 is any one of a polyphenylalkyl group, a biphenyl-type polycyclic aromatic hydrocarbon group, a spirobifluorene-type group, and a fused ring aromatic hydrocarbon group, including but not limited to: biphenyl, phenanthryl, fluorenyl, anthracyl, fluoranthenyl, triphenylenyl, naphthyl, and the like. The polycyclic arylo group may be phenanthro, anthraco, fluorantheno, triphenylo, naphtho, or the like.
In a preferred embodiment of the present invention, the compound containing carbazole and quinazoline structure of the present invention is selected from the compounds represented by the following structures:
in a second aspect, the present invention provides a preparation method of the carbazole and quinazoline containing compound, which can be synthesized by the following method according to different substituents in the general formula:
the synthetic route is as follows:
the synthesis method comprises the following steps:
to be provided with
Reacting with triisopropyl borate under the condition of n-butyl lithium to obtain the compound
The above-mentioned
And
prepared by Suzuki reaction as raw material
The above-mentioned
And
as raw material, performing coupling reaction under alkaline condition to obtain
Wherein, the
The reaction molar ratio of the n-butyl lithium to the triisopropyl borate is 1:1.1:1.2, and the reaction temperature is-75 ℃; the above-mentioned
And
and alkali in a molar ratio of 1:1:2, and at a reaction temperature of 70 ℃; the above-mentioned
And
and alkali in a molar ratio of 1:1:2, and at a reaction temperature of 150 ℃; wherein the adopted alkali is potassium carbonate.
In the above preparation method, said R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14As defined above.
The OLED compound can be stably and efficiently obtained by the preparation method.
In a third aspect, the invention provides an application of the compound containing carbazole and quinazoline structures in an OLED device. Specifically, the organic electronic device is used as a functional material in an organic electronic device, and the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet type scanner or electronic paper.
Preferably, the compound containing carbazole and quinazoline structure shown in the general formula (I) is used as a luminescent material in an organic electroluminescent device.
In a fourth aspect, the present invention provides an organic electroluminescent device, which includes a light-emitting layer, wherein the material of the light-emitting layer contains the carbazole-and quinazoline-containing compound.
Specifically, the invention provides an organic electroluminescent device, which sequentially comprises a transparent substrate, an anode layer, a hole injection layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top, wherein a luminescent material of the luminescent layer comprises the compound shown in the general formula (I) provided by the invention.
In a preferred embodiment, the thickness of the light-emitting layer may be 20 to 50nm, preferably 20 to 40 nm.
In a fifth aspect, the present invention provides a display apparatus comprising the organic electroluminescent device.
In a sixth aspect, the present invention provides a lighting apparatus comprising the organic electroluminescent device.
The invention provides a carbazole and quinazoline structure-containing compound with a new structure, which takes carbazole and quinazoline as parent nucleus structures, has good bipolar transmission performance, is suitable for electron transmission and hole transmission, and can be used as a host material. Substituent group R1～R14The charge density and the electron cloud distribution of molecules can be influenced, the energy level of the molecules can be regulated and controlled, the HOMO and LUMO energy levels of the molecules are matched with adjacent materials, and the driving voltage is reduced; at the same time, film formation is also affectedThe accumulation state of the material balances the carrier transmission, improves the charge transmission performance of the material, and improves the luminous efficiency of the device.
The compound is applied to an OLED device, can reduce the driving voltage and improve the current efficiency of the device, and is an OLED material with excellent performance.
Detailed Description
The technical solution of the present invention will be explained in detail below. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The starting materials are commercially available from the open literature unless otherwise specified.
Example 1
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-1-1: under nitrogen protection, 600ml of tetrahydrofuran was added to a reaction flask, and 33.62g (100mmol) of 3-bromo-N- (4-methylphenyl) carbazole and 22.56g (120mmol) of triisopropyl borate were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up of the reaction gave 20.47g of a white solid in 68% yield.
(2) Synthesis of Compound I-1-2: 30.11g of compound I-1-1(100mmol), 24.61g (100mmol) of 3-bromocarbazole and 500ml of toluene are added into a reaction bottle under the protection of nitrogen, stirred, and added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up of the reaction gave 27.04g of a white solid in 64% yield.
(3) Synthesis of Compound I-1: under the protection of nitrogen, to42.25g of Compound I-1-2(100mmol) and 600ml of N-N-dimethylformamide were charged into a reaction flask, and the mixture was stirred. 24.07g (100mmol) of 2-chloro-4-phenylquinazoline and 0.92g Pd were added2(dba)3(1mmol) and 27.6g (200mmol) of potassium carbonate, and the reaction was carried out at 150 ℃ for 4 hours or more. Work-up of the reaction gave 41.99g of a yellow solid in 67% yield.
Elemental analysis (C)45H30N4): theoretical value C: 86.24%, H: 4.82%, N: 8.94 percent; found value C: 86.44%, H: 4.92%, N: 8.64 percent.
Example 2
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-8-1: 600ml of tetrahydrofuran was added to a reaction flask under nitrogen protection, and 32.22g (100mmol) of 3-bromo-N-phenylcarbazole and 22.56g (120mmol) of triisopropyl borate were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up of the reaction gave 19.8g of a white solid in 69% yield.
(2) Synthesis of Compound I-8-2: under the protection of nitrogen, 28.71g of compound I-8-1(100mmol), 24.61g (100mmol) of 3-bromocarbazole and 500ml of toluene are added into a reaction bottle, stirred, and added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up of the reaction gave 27.37g of a white solid in 67% yield.
(3) Synthesis of Compound I-8: 40.85g of Compound I-8-2(100mmol) and 600ml of N-N-dimethylformamide were added to a reaction flask under nitrogen protection, and the mixture was stirred. 28.28g (100mmol) of 2-chloro-4- (2 ', 4 ', 6 ' -trimethylphenyl) quinazoline, 0.92g Pd were added2(dba)3(1mmol) and 27.6g (200mmol) of potassium carbonate, and the reaction was carried out at 150 ℃ for 4 hours or more. Work-up of the reaction gave 41.9g of a yellow solid in 64% yield.
Elemental analysis (C)47H34N4): theoretical value C: 86.21%, H: 5.23%, N: 8.56 percent; found value C: 86.16%, H: 5.38%, N: 8.46 percent.
Example 3
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-28-1: under nitrogen protection, 600ml of tetrahydrofuran was added to a reaction flask, and 34.02g (100mmol) of 5-fluoro-3-bromo-N-phenylcarbazole and 22.56g of triisopropyl borate (120mmol) were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up after the reaction gave 19.82g of a white solid in 65% yield.
(2) Synthesis of Compound I-28-2: under the protection of nitrogen, 30.51g of compound I-28-1(100mmol), 24.61g (100mmol) of 3-bromocarbazole and 500ml of toluene are added into a reaction bottle, stirred, and added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up of the reaction gave 27.29g of a white solid in 64% yield.
(3) Synthesis of Compound I-28: nitrogen gasUnder protection, 42.65g of Compound I-28-2(100mmol), 600ml of N-N-dimethylformamide was added to the reaction flask, and the mixture was stirred. 24.07g (100mmol) of 2-chloro-4-phenylquinazoline and 0.92g Pd were added2(dba)3(1mmol) and 27.6g (200mmol) of potassium carbonate, and the reaction was carried out at 150 ℃ for 4 hours or more. Work-up of the reaction gave 39.1g of a yellow solid in 62% yield.
Elemental analysis (C)44H27FN4): theoretical value C: 83.79%, H: 4.32%, N: 8.88 percent; found value C: 83.89%, H: 4.12%, N: 8.98 percent.
Example 4
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-30-1: 600ml of tetrahydrofuran was added to a reaction flask under nitrogen protection, and 32.22g (100mmol) of 3-bromo-N-phenylcarbazole and 22.56g (120mmol) of triisopropyl borate were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up of the reaction gave 19.8g of a white solid in 69% yield.
(2) Synthesis of Compound I-30-2: under the protection of nitrogen, 28.71g of compound I-30-1(100mmol), 26.41g (100mmol) of 5-fluoro-3-bromocarbazole and 500ml of toluene are added into a reaction bottle, stirred, added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up after the reaction gave 26.86g of a white solid in 63% yield.
(3) Synthesis of Compound I-30: under the protection of nitrogen, 42.65g of compound I-30-2(100mmol), N-N-dimethylformamide 600ml, stirring. 24.07g (100mmol) of 2-chloro-4-phenylquinazoline and 0.92g Pd were added2(dba)3(1mmol) and 27.6g (200mmol) of potassium carbonate, and the reaction was carried out at 150 ℃ for 4 hours or more. Work-up of the reaction gave 38.47g of a yellow solid in 61% yield.
Elemental analysis (C)44H27FN4): theoretical value C: 83.79%, H: 4.32%, N: 8.88 percent; found value C: 83.87%, H: 4.41%, N: 8.75 percent.
Example 5
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-32-1: under nitrogen protection, 600ml of tetrahydrofuran was added to a reaction flask, and 34.02g (100mmol) of 5-fluoro-3-bromo-N-phenylcarbazole and 22.56g of triisopropyl borate (120mmol) were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up after the reaction gave 19.82g of a white solid in 65% yield.
(2) Synthesis of Compound I-32-2: under the protection of nitrogen, 30.51g of compound I-32-1(100mmol), 26.01g (100mmol) of 5-methyl-3-bromocarbazole and 500ml of toluene are added into a reaction bottle, stirred, added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up of the reaction gave 27.31g of a white solid in 62% yield.
(3) Synthesis of Compounds I-32: 44.05g of Compound I-32-2(100mmol) and 600ml of N-N-dimethylformamide were added to a reaction flask under nitrogen protection, and the mixture was stirred. 24.07g (100mmol) of 2-chloro-4-phenylquinazoline and 0.92g Pd were added2(dba)3(1mmol) and 27.6g (200mmol) of potassium carbonate, and the reaction was carried out at 150 ℃ for 4 hours or more. Work-up of the reaction gave 39.1g of a yellow solid in 64% yield.
Elemental analysis (C)45H29FN4): theoretical value C: 83.83%, H: 4.53%, N: 8.69 percent; found value C: 83.89%, H: 4.22%, N: 8.85 percent.
Example 6
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-36-1: under nitrogen protection, 600ml of tetrahydrofuran was added to a reaction flask, and 35.42g (100mmol) of 5-fluoro-3-bromo-N- (4' -methylphenyl) carbazole and 22.56g of triisopropyl borate (120mmol) were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up after the reaction gave 20.73g of a white solid in 65% yield.
(2) Synthesis of Compound I-36-2: 31.91g of the compound I-36-1(100mmol), 26.41g (100mmol) of 5-fluoro-3-bromocarbazole and 500ml of toluene are added into a reaction flask under the protection of nitrogen, stirred, added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up of the reaction gave 29.34g of a white solid in 64% yield.
(3) Synthesis of Compound I-36: 45.85g of Compound I-36-2(100mmol) and 600ml of N-N-dimethylformamide were added to a reaction flask under nitrogen protection, and the mixture was stirred. 25.47g (100mmol) of 2-chloro-4- (4' -methylphenyl) quinazoline and 0.92g Pd were added2(dba)3(1mmol), Potassium carbonate 27.6g (200mmol), LThe temperature is raised to 150 ℃, and the reaction lasts for more than 4 hours. Work-up of the reaction gave 42.63g of a yellow solid in 63% yield.
Elemental analysis (C)46H30F2N4): theoretical value C: 81.64%, H: 4.47%, N: 8.28 percent; found value C: 81.71%, H: 4.53%, N: 8.14 percent.
Example 7
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-40-1: 600ml of tetrahydrofuran was added to a reaction flask under nitrogen protection, and 41.63g (100mmol) of 5-fluoro-3-bromo-N-biphenylcarbazole and 22.56g of triisopropyl borate (120mmol) were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up of the reaction gave 24.01g of a white solid in 63% yield.
(2) Synthesis of Compound I-40-2: 38.12g of compound I-40-1(100mmol), 26.41g (100mmol) of 5-fluoro-3-bromocarbazole and 500ml of toluene are added into a reaction flask under the protection of nitrogen, stirred, and added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up of the reaction gave 32.79g of a white solid in 63% yield.
(3) Synthesis of Compound I-40: 52.06g of Compound I-40-2(100mmol) and 600ml of N-N-dimethylformamide were added to a reaction flask under nitrogen protection, and the mixture was stirred. Adding28.28g (100mmol) of 2-chloro-4- (2 ', 4 ', 6 ' -trimethylphenyl) quinazoline and 0.92g Pd2(dba)3(1mmol) and 27.6g (200mmol) of potassium carbonate, and the reaction was carried out at 150 ℃ for 4 hours or more. Work-up of the reaction gave 46.11g of a yellow solid in 62% yield.
Elemental analysis (C)50H29F3N4): theoretical value C: 80.85%, H: 3.94%, N: 7.54 percent; found value C: 80.92%, H: 3.98%, N: 7.46 percent.
Example 8
The synthesis route is as follows:
the specific operation steps are as follows:
(1) synthesis of Compound I-46-1: under nitrogen protection, 600ml of tetrahydrofuran was added to a reaction flask, and 43.43g (100mmol) of 5-fluoro-3-bromo-N- (4' -p-fluorophenyl) phenylcarbazole and 22.56g of triisopropyl borate (120mmol) were added thereto with stirring. 44ml of n-butyllithium (2.5mol/L) are added dropwise when the temperature is reduced to-75 ℃. After the dripping is finished for 30min, the temperature is kept at minus 75 ℃ in the dripping process, and the temperature is kept at minus 75 ℃ for reaction for 2 hours after the dripping is finished. Work-up after the reaction gave 24.75g of a white solid in 62% yield.
(2) Synthesis of Compound I-46-2: 39.92g of compound I-46-1(100mmol), 26.41g (100mmol) of 5-fluoro-3-bromocarbazole and 500ml of toluene are added into a reaction flask under the protection of nitrogen, stirred, and added with 80ml of ethanol, 40ml of water, 27.6g (200mmol) of potassium carbonate and 0.92g of Pd2(dba)3(1mmol), the temperature was raised to 70 ℃ and the reaction was carried out for 4 hours or more. Work-up of the reaction gave 31.23g of a white solid in 58% yield.
(3) Synthesis of Compound I-46: under nitrogen protection, 53.85g of Compound I-46-2(100mmol), 600ml of N-N-dimethylformamide was added to the reaction flask, and the mixture was stirred. Adding 5-fluoro-2-chloro-4- (4' -fluorobenzene)Yl) quinazoline 27.67g (100mmol), 0.92g Pd2(dba)3(1mmol) and 27.6g (200mmol) of potassium carbonate, and the reaction was carried out at 150 ℃ for 4 hours or more. Workup of the reaction gave 47.5g of a yellow solid in 61% yield.
Elemental analysis (C)50H27F5N4): theoretical value C: 77.11%, H: 3.49%, N: 7.19 percent; found value C: 77.16%, H: 3.54%, N: 7.13 percent.
According to the synthesis methods of examples 1 to 8, other compounds in I-1 to I-52 can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 9
The embodiment provides a group of OLED red light devices, and the device structure is as follows: ITO/HATCN (1nm)/HT01(40nm)/NPB (20 nm)/the representative compound of the present invention and the doping dye (30nm)/BPhen (40nm)/LiF (1nm)/Al provided by examples 1 to 8, the preparation process is:
(1) carrying out ultrasonic treatment on a glass substrate coated with an ITO transparent conducting layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic oil removal in an acetone-ethanol mixed solvent (volume ratio is 1: 1), baking in a clean environment until water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, vacuumizing to 1 x 10 < -5 > to 9 x 10 < -3 > Pa, and performing vacuum evaporation on the anode layer film to form HATCN serving as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm; then, evaporating and plating a layer of NPB (N-propyl bromide) on the hole injection layer film to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm; wherein the structural formulas of HATCN, HT01 and NPB are as follows:
(3) vacuum evaporating EML on the hole transport layer as the light emitting layer of the device, the EML including a main bodyA material and a doping material. Representative compounds of the invention, prepared in examples 1-8, were used as light emitting host materials, and Ir (piq)2acac is a doped material. By using a multi-source co-evaporation method, the evaporation rate of a main material is adjusted to be 0.1nm/s, and a doping material Ir (piq)2The mass concentration of acac is 5%, and the total film thickness of evaporation coating is 30 nm; wherein Ir (piq)2The structural formula of acac is as follows:
(4) and continuously performing vacuum evaporation on the electron transport material BPhen on the luminescent layer, wherein the evaporation rate is 0.1nm/s, the total film thickness of the evaporation is 40nm, and the electron transport layer is obtained, and the BPhen has the following structural formula:
(5) sequentially vacuum evaporating LiF with the thickness of 1nm on the electron transport layer to serve as an electron injection layer of the device, continuously evaporating a layer of Al on the electron injection layer to serve as a cathode of the device, and evaporating the film with the thickness of 150 nm; a series of OLED devices provided by the invention are obtained.
According to the same procedure as above, only the host material in step (3) was replaced with the following prior art compound DCQ as a comparative compound, the structural formula of which is shown below, to prepare a comparative device OLED-9.
The invention detects the performances of the devices OLED-1 to OLED-9. The results are shown in Table 1.
Table 1:
from the results in table 1 above, it can be seen that the current efficiency of the devices OLED-1 to OLED-8 prepared by using the organic material represented by the general formula (I) provided by the present invention is higher than that of the comparative example OLED-9, and the operating voltage is significantly lower than that of the device using DCQ as the host material under the same luminance condition.
The results show that the organic material shown in the general formula (I) provided by the invention is a novel red light main body material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A compound containing carbazole and quinazoline structures has a structure shown as a general formula (I):
in the formula (I), R1、R2A substituent group representing mono-substitution to the maximum allowable number of substitution;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13and R14The substituent groups are respectively and independently selected from one of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C40 monocyclic aryl or polycyclic aryl, and the substituent groups are respectively and independently selected from one of halogen, C1-C10 chain alkyl, C6-C30 aryl and C3-C30 heteroaryl; and R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14Not hydrogen at the same time;
A1and A2The aryl group is respectively and independently selected from substituted or unsubstituted C6-C60 arylene, and the substituent groups are respectively and independently selected from one of halogen, C1-C20 chain alkyl and C3-C20 cycloalkyl.
2. The compound containing carbazole and quinazoline structure according to claim 1, wherein a is a1And A2Each independently selected from 1, 4-phenylene, 2-methyl-1, 4-phenylene, 3-methyl-1, 4-phenylene, 2, 6-dimethyl-1, 4-phenylene, monofluoro-1, 4-phenylene, difluoro-1, 4-phenylene, trifluoro-1, 4-phenylene, and tetrafluoro-1, 4-phenylene.
3. The compound having a carbazole and quinazoline structure according to claim 1, which is selected from the structures represented by any one of the following general formulae I-1 to I-4:
in the above general formula I-1 to formula I-4, R1、R2A substituent group representing mono-substitution to the maximum allowable number of substitution; r1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14Is as defined in formula I.
4. The carbazole-and-quinazoline structure-containing compound according to claim 1 or 3, wherein R is represented by the formula1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14Each independently selected from hydrogen, methyl, fluorine atom, substituted or unsubstituted phenyl, and substituted or unsubstituted biphenyl, the substituent groups are respectively and independently selected from one of halogen, chain alkyl of C1-C5, aryl of C6-C30, and heteroaryl of C3-C30, and R is1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13And R14Not hydrogen at the same time;
preferably, said R is1、R2At least one of which is selected from one of methyl, fluorine atom, methyl-substituted phenyl, methyl-substituted biphenyl, fluorine-substituted phenyl, fluorine-substituted biphenyl.
5. The compound containing carbazole and quinazoline structure according to claim 1, characterized by being selected from compounds represented by the following structures:
6. the method for synthesizing a compound having a carbazole and quinazoline structure according to claim 1, comprising the steps of:
to be provided with
Reacting with triisopropyl borate under the condition of n-butyl lithium to obtain the compound
The above-mentioned
And
prepared by Suzuki reaction as raw material
The above-mentioned
And
as raw material, performing coupling reaction under alkaline condition to obtain
Wherein, the
The reaction molar ratio of the n-butyl lithium to the triisopropyl borate is 1:1.1:1.2, and the reaction temperature is-75 ℃; the above-mentioned
And
and alkali in a molar ratio of 1:1:2, and at a reaction temperature of 70 ℃; the above-mentioned
And
and alkali in a molar ratio of 1:1:2, and at a reaction temperature of 150 ℃; wherein the adopted alkali is potassium carbonate.
7. The use of the carbazole-and quinazoline-based structural compound according to any one of claims 1 to 5 as a functional material in an organic electronic device, the organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper;
preferably, the compound containing carbazole and quinazoline structure is applied to being used as a luminescent layer material in an organic electroluminescent device.
8. An organic electroluminescent device comprising an anode, a cathode and one or more light-emitting functional layers interposed between the anode and the cathode, wherein the light-emitting functional layers contain the compound containing carbazole and quinazoline structure of any one of claims 1 to 5;
preferably, the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, and the light-emitting layer contains the compound containing carbazole and quinazoline structure as claimed in any one of claims 1 to 5.
9. A display apparatus comprising the organic electroluminescent device according to claim 9.
10. A lighting device comprising the organic electroluminescent device according to claim 9.
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