CN117987141A - Electroluminescent material and organic electroluminescent device comprising same - Google Patents
Electroluminescent material and organic electroluminescent device comprising same Download PDFInfo
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- CN117987141A CN117987141A CN202211319307.9A CN202211319307A CN117987141A CN 117987141 A CN117987141 A CN 117987141A CN 202211319307 A CN202211319307 A CN 202211319307A CN 117987141 A CN117987141 A CN 117987141A
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- 239000000463 material Substances 0.000 title claims abstract description 109
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 239000010410 layer Substances 0.000 claims description 116
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 230000000903 blocking effect Effects 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 13
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims 2
- 230000005540 biological transmission Effects 0.000 abstract description 20
- 230000006798 recombination Effects 0.000 abstract description 8
- 238000013329 compounding Methods 0.000 abstract description 5
- 230000001105 regulatory effect Effects 0.000 abstract description 5
- 238000013461 design Methods 0.000 abstract description 4
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 15
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- 238000005516 engineering process Methods 0.000 description 8
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- 239000003086 colorant Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 229910052698 phosphorus Inorganic materials 0.000 description 2
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- 230000002035 prolonged effect Effects 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
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- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910014455 Ca-Cb Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
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- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000004988 dibenzothienyl group Chemical class C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an electroluminescent material and an organic electroluminescent device comprising the same, wherein the electroluminescent material comprises a combination of a first compound and a second compound, and has excellent photoelectric performance through the structural design and the compounding cooperation of the compounds, and is suitable for a luminescent layer, particularly a main body material, of the organic electroluminescent device. In the organic electroluminescent device containing the electroluminescent material, the electroluminescent material is used as a main material, so that the carrier recombination probability can be improved, the carrier transmission is balanced, the transmission balance of holes and electrons is realized, and the position of the electron and hole recombination center in the luminescent layer is regulated and controlled to occur at the central position of the luminescent layer, thereby effectively improving the luminous efficiency of the device, and greatly improving the stability and the service life of the device.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an electroluminescent material and an organic electroluminescent device comprising the same.
Background
The organic electroluminescence technology is a new generation display technology which is emerging in recent years, has the advantages of self-luminescence, high contrast, quick response, wide color gamut, wide viewing angle, flexibility, low power consumption and the like, is developed very rapidly in recent years, has been successful in commerce, and is widely applied to a plurality of fields such as flexible display, flat panel display, solid state lighting and the like.
The organic electroluminescent (OLED) device comprises a cathode, an anode and an organic film structure arranged between the two electrodes, and the core of the organic electroluminescent (OLED) device is the film structure containing various organic functional materials. Common organic functional materials include: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest material (dye), and the like. When energized, electrons and holes are injected, transported to the light emitting region, respectively, and recombined therein, thereby generating excitons and emitting light.
In recent years, industry has continuously tried and explored to improve the efficiency and stability of OLED devices, and a great deal of new materials are developed for use in organic electroluminescent devices because of the majority of ways to seek new materials to improve the performance of the devices. With the continuous upgrading of electronic products and illumination products, higher requirements are put on the photoelectric performance of the OLED device, but the existing OLED device has the problem that carriers are accumulated in a large amount at an interface, and the efficiency and the service life of the device are obviously insufficient. Accordingly, there is a need in the art to develop organic electroluminescent materials and OLED devices having higher performance.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an electroluminescent material and an organic electroluminescent device comprising the electroluminescent material, and the electroluminescent material has excellent photoelectric performance through structural design and compounding of compounds, can effectively regulate and control carrier transmission characteristics, and realizes the balance of hole and electron transmission, thereby remarkably improving the efficiency and the service life of the organic electroluminescent device comprising the electroluminescent material.
In order to achieve the aim of the invention, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an electroluminescent material comprising a combination of a first compound and a second compound.
The first compound has a structure as shown in formula I:
In the formula I, L 1、L2、L3 is independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene and substituted or unsubstituted C3-C30 heteroarylene; when L 1 is a single bond, ar 1 is directly connected to the N atom by a single bond; l 2 and L 3 are the same and are not described in detail.
In the formula I, ar 2、Ar3 is independently selected from any one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
In the formula I, ar 1 is
Wherein R 1、R2、R3、R4、R5、R6、R7、R8 is each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryl.
One group of any two adjacent groups in R 1、R2、R3、R4 is connected into a ring A through a chemical bond, and the ring A is* Representing the attachment site of the group.
In ring A, R 9、R10、R11、R12 is each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryl.
In R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12, at least one group of any adjacent two groups among other groups except the group forming the ring a is linked to form a ring by a chemical bond.
In Ar 1, one of any two adjacent groups R 1 to R 4 is connected to form a ring a by a chemical bond, and at least one group (e.g., group 1, group 2, group 3, etc.) of any two adjacent groups R 5 to R 12 is connected to form a ring by a chemical bond; in addition to the aforementioned defined at least 4 groups that must be cyclic, no bond or chemical bond is made between two other adjacent groups in R 1 to R 12.
X, Y are each independently selected from any one of a single bond, NR A1, O, S or CR A2RA3, and the X and Y are not both single bonds; when X and Y are not single bonds, the ring A contains a ring structure formed by fusing a benzene ring and a six-membered ring; when one of X and Y is a single bond, the ring A contains a ring structure formed by fusing a benzene ring and a five-membered ring.
R A1 is selected from any one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
R A2、RA3 is each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
The substituted substituents in formula I are each independently selected from at least one of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino.
The second compound has a structure as shown in formula II:
in the formula II, ar is selected from any one of substituted or unsubstituted C3-C30 nitrogen-containing heteroaryl;
in the formula II, L is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene and substituted or unsubstituted C3-C30 heteroarylene;
In formula II, cy is The L is attached to the ring Cy at any position that can be attached.
The dashed line represents the optional structure of ring E, i.e., the presence or absence of ring E in ring Cy.
Ring E is selected from any one of a substituted or unsubstituted C6-C20 aromatic ring and a substituted or unsubstituted C3-C20 heteroaromatic ring.
R 21、R22 is each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
M 1 represents the number of substituents R 21, selected from integers from 0 to 4, for example, may be 0, 1, 2, 3 or 4; when m 1 is not less than 2, a plurality of (at least 2) R 21 are the same or different groups.
M 2 represents the number of substituents R 22, selected from integers from 0 to 6, for example, may be 0,1, 2,3,4, 5 or 6; when m 2 is not less than 2, a plurality of (at least 2) R 22 are the same or different groups.
The substituted substituents in formula II are each independently selected from at least one of halogen, cyano, nitro, hydroxy, amino, aldehyde, ester, C1-C30 straight or branched alkyl, C1-C30 alkoxy, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, unsubstituted or R 'substituted C6-C30 aryl, unsubstituted or R' substituted C3-C30 heteroaryl;
Each R' is independently selected from at least one of halogen, cyano, unsubstituted or halogenated C1-C10 straight or branched alkyl, C6-C20 aryl or C3-C20 heteroaryl.
The electroluminescent material provided by the invention comprises the combination of the first compound with the structure shown in the formula I and the second compound with the structure shown in the formula II, and has good photoelectric property through the design of the structure of the compounds and the compounding cooperation of the two types of compounds, is suitable for being used as a luminescent layer material, especially a main body material, and effectively improves various properties of an organic electronic device. The first compound can play a role in adjusting injection and transmission of holes in the luminous layer, so that a carrier composite region in the luminous layer is adjusted and controlled, and the first compound has a higher space accumulation structure; meanwhile, the second compound has higher molecular plane unfolding property and good electron transmission property. The electroluminescent material compounded by the two can coordinate the characteristic of faster electron transfer of the second compound, thereby effectively regulating and controlling the transmission balance of holes and electrons, regulating and controlling the position of the electron and hole recombination center in the luminescent layer to occur at the central position of the luminescent layer, avoiding the problem that carriers are accumulated in a large quantity at the interface, and remarkably improving the efficiency and the service life of the device. In addition, the energy level difference between the electroluminescent material and the doping material is small, so that the loss in the energy transfer process is less, the utilization rate of excitons is improved, and the efficiency, the stability and the service life of the device are further improved.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural (at least 2), the substituents may be the same or different substituents; when the following description refers to the same expression mode, the same meaning is provided, and the selection ranges of the substituents are shown above and are not repeated.
In the present invention, unless otherwise specified, the expression of chemical elements includes the concept of isotopes having the same chemical properties, for example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), and the like; carbon (C) includes 12C、13 C and the like.
In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, si or an atom or group of atoms in Se, preferably N, O, S.
In the present invention, the expression "ring structure" means that the linking site is located at any position on the ring structure that can be bonded.
In the present invention, the expression of Ca-Cb means that the group has a carbon number of a-b, and generally the carbon number does not include the carbon number of the substituent unless otherwise specified.
In the present invention, "each independently" means that the subject has a plurality of subjects, and the subjects may be the same or different from each other.
In the present invention, the C1-C30 linear or branched alkyl group, preferably C1-C20 linear or branched alkyl group, may be a linear or branched alkyl group of C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or the like, and more preferably a C1-C10 linear or branched alkyl group; exemplary include, but are not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl and the like.
Specific examples of the C1-C30 alkoxy group, preferably C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18) alkoxy group, include monovalent groups obtained by linking the above-mentioned examples of the linear or branched alkyl group to O.
In the present invention, the C3-C30 cycloalkyl group, preferably C3-C20 cycloalkyl group, may be a cycloalkyl group such as C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.; exemplary include, but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
Specific examples of the C2-C30 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, or C28, etc.) heterocycloalkyl group include, but are not limited to, monovalent groups obtained by substituting at least one ring C atom with a heteroatom (e.g., O, S, N or P, etc.) in the examples of the cycloalkyl group described above: epoxy, tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothienyl, morpholinyl, piperidinyl, and the like.
In the present invention, the C6-C30 aryl groups may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc., and preferably C6-C20 aryl groups, including monocyclic aryl groups or condensed ring aryl groups. By monocyclic aryl is meant that the group contains at least 1 phenyl group and when at least 2 phenyl groups are present, the phenyl groups are linked by single bonds, exemplary including but not limited to: phenyl, biphenyl, terphenyl, and the like; by fused ring aryl is meant a group containing at least 2 aromatic rings in the group and having two adjacent carbon atoms in common between the aromatic rings that are fused to each other, exemplary include, but are not limited to: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof (9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthryl, triphenylene, pyrenyl, perylenyl,A radical or a tetracenyl radical, etc.; the foregoing list of groups includes all possible linkages thereof.
In the present invention, the C3-C30 heteroaryl groups may be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28 heteroaryl groups, including monocyclic heteroaryl groups or condensed ring heteroaryl groups. The monocyclic heteroaryl means that at least one heteroaryl group is contained in the molecule, and when a heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.) are contained in the molecule, the heteroaryl group and other groups are linked by a single bond, and exemplary examples include, but are not limited to: furyl, thienyl, pyrrolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl and the like. By fused ring heteroaryl is meant a group having at least one aromatic heterocycle and one aromatic ring (either aromatic heterocycle or aromatic ring) in the molecule and sharing two adjacent atoms fused to each other, exemplary including but not limited to: benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and derivatives thereof (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, etc.; the foregoing list of groups includes all possible linkages thereof.
Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) arylene group include a divalent group obtained by removing one hydrogen atom in the above examples of the aryl group; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) heteroarylene group include a divalent group obtained by removing one hydrogen atom from the above heteroaryl group.
The C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino group, i.e., a monovalent group formed by substitution of at least one H on-NH 2 with an aryl group as recited above, illustratively includes, but is not limited to: phenylamino, biphenylamino, naphthylamino, and the like. The C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino group, i.e., a monovalent group formed by substitution of at least one H on-NH 2 with a heteroaryl group as recited above.
In the present invention, the halogen includes fluorine, chlorine, bromine or iodine; the following description refers to the same meaning.
Preferably, each of said L 1、L2、L3 is independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 (e.g., C6, C7, C8, C9, C10, C12, C14, C16, or C18, etc.) arylene, a substituted or unsubstituted C6-C20 (e.g., C6, C7, C8, C9, C10, C12, C14, C16, or C18, etc.) heteroarylene.
Preferably, each of said L 1、L2、L3 is independently selected from a single bond, Any one of them; wherein U is O or S, representing the attachment site of the group.
Preferably, each Ar 2、Ar3 is independently selected from any one of the following substituted or unsubstituted groups:
* Representing the attachment site of the group.
Wherein each Z 1、Z2、Z3 is independently selected from any one of O, S, NR 32 or CR 33R34.
R 31、R32、R33、R34 is each independently selected from any one of hydrogen, C1-C20 straight or branched chain alkyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino.
Preferably, each R 31、R32、R33、R34 is independently selected from any of C1-C6 (e.g., C2, C3, C4, C5) straight or branched alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, or naphthylphenyl.
Preferably, each R 31、R33、R34 is independently methyl or phenyl.
Preferably, the R 32 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl and naphthylphenyl.
Preferably, in ring A, X is selected from any one of NR A1, O, S or CR A2RA3, Y is a single bond, i.e. ring A is* Representing the attachment site of the group.
Preferably, ar 1 is selected from any one of the following groups a-f:
wherein represents the attachment site of the group.
X is selected from any one of NR A1, O, S or CR A2RA3.
R A1 is selected from any one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
R A2、RA3 is each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12 Each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 heteroaryl, and substituted or unsubstituted C6-C30 aryl.
In Ar 1, at least one group of adjacent R M and R M+1 are connected into a ring through a chemical bond, M represents the subscript number of a group and is an integer of 1-11.
Specifically, when Ar 1 is a group a or a group c, at least one group (e.g., group 1, group 2, etc.) of any two adjacent groups in R 5、R6、R7、R8、R9、R10、R11、R12 is linked to form a ring by a chemical bond. When Ar 1 is a group b or a group d, at least one group (e.g., group 1, group 2, etc.) of any two adjacent groups in R1、R2、R5、R6、R7、R8、R9、R10、R11、R12 are linked by a chemical bond to form a ring. When Ar 1 is a group e or a group f, at least one group (e.g., group 1, group 2, etc.) of any two adjacent groups in R3、R4、R5、R6、R7、R8、R9、R10、R11、R12 are linked by a chemical bond to form a ring.
Preferably, in Ar 1, at least one group of adjacent R M and R M+1 is connected to form a benzene ring through a chemical bond, and M is an integer from 1 to 11.
Preferably, ar 1 is selected from any one of the following groups:
Preferably, each of said R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12 is independently selected from any of hydrogen, substituted or unsubstituted C1-C6 (e.g., C2, C3, C4, C5, etc.) linear or branched alkyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl; the substituted substituents are each independently selected from at least one of halogen, C1-C6 (e.g., C2, C3, C4, C5, etc.), straight or branched chain alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.), aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.), heteroaryl.
Preferably, each of said R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12 is independently selected from any one of hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, unsubstituted or phenyl-substituted quinolinyl, unsubstituted or phenyl-substituted isoquinolinyl, unsubstituted or phenyl-substituted quinazolinyl, unsubstituted or phenyl-substituted quinoxalinyl.
Preferably, ar 1 is selected from any one of the following substituted or unsubstituted groups:
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Wherein represents the attachment site of the group; the substituted substituents have the same defined range as R 1-R12; preferably, the substituted substituent is selected from any one of substituted or unsubstituted C1-C6 (e.g., C2, C3, C4, C5, etc.) straight or branched chain alkyl, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl, further preferably any one of phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, unsubstituted or phenyl-substituted quinolinyl, unsubstituted or phenyl-substituted isoquinolinyl, unsubstituted or phenyl-substituted quinazolinyl, unsubstituted or phenyl-substituted quinoxalinyl.
X is selected from any one of NR A1, O, S or CR A2RA3.
R A1 is selected from any one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
R A2、RA3 is each independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
The substituents substituted in R A1、RA2、RA3 are each independently selected from at least one of halogen, C1-C20 straight or branched chain alkyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino.
Preferably, the R A1 is selected from any of substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl.
Preferably, said R A1 is selected from
Any one of them;
Preferably, each R A2、RA3 is independently selected from any one of hydrogen, C1-C6 (e.g., C2, C3, C4, C5, etc.) straight or branched alkyl, phenyl.
Preferably, the first compound has any one of the structures shown as P1-P328 below:
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Preferably, in formula II, ar is a group having electron withdrawing properties.
Preferably, in formula II, ar is selected from any one of substituted or unsubstituted C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, or C10) nitrogen-containing heteroaryl groups.
Preferably, ar is selected from any one of the following groups:
Wherein the dotted line represents the attachment site of the group.
R 41、R42 is independently selected from any one of hydrogen, halogen, cyano, C1-C30 straight or branched chain alkyl, unsubstituted or R 'substituted C6-C30 aryl, unsubstituted or R' substituted C3-C30 heteroaryl.
R 43 is independently selected from any one of halogen, cyano, C1-C30 straight or branched chain alkyl, unsubstituted or R 'substituted C6-C30 aryl, unsubstituted or R' substituted C3-C30 heteroaryl.
Each R' is independently selected from at least one of halogen, cyano, unsubstituted or halogenated C1-C10 straight or branched alkyl, C6-C20 aryl or C3-C20 heteroaryl.
N 1、n2 represents the number of substituents R 43, n 1 is selected from integers from 0 to 3, for example may be 0, 1, 2 or 3; n 2 is an integer from 0 to 5, for example, may be 0, 1, 2, 3,4 or 5; wherein when n 1≥2、n2 is not less than 2, a plurality of (at least 2) R 43 are the same or different groups.
Preferably, each of the R 41、R42 is independently selected from any of hydrogen, unsubstituted or R 'substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, unsubstituted or R' substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl.
Preferably, each of the R 43 is independently selected from any of unsubstituted or R 'substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl, unsubstituted or R' substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl.
Preferably, each R' is independently selected from at least one of halogen, cyano, unsubstituted or halogenated C1-C6 (e.g., C2, C3, C4, C5, etc.), straight or branched chain alkyl, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.), aryl, C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.), heteroaryl, further preferably at least one of halogen, cyano, phenyl, unsubstituted or cyano-substituted biphenyl, unsubstituted or cyano-substituted terphenyl, naphthyl, pyridylphenyl, pyrimidinylphenyl, pyrazinylphenyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl, dibenzofuranylphenyl, dibenzothiophenyl, dimethylfluorenylphenyl, and the like.
Preferably, ar is selected from any one of the following groups:
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Wherein R 51、R52、R53 is each independently selected from hydrogen, * Representing the attachment site of the group.
Preferably, in formula II, L is selected from any one of a single bond, a substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) arylene, a substituted or unsubstituted C5-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroarylene.
Preferably, L is selected from the group consisting of a single bond, Any one of them; * Representing the attachment site of the group.
Preferably, in formula II, the ring E is a benzene ring.
Preferably, both m 1 and m 2 are 0.
Preferably, the ring Cy isThe L in formula II may be attached to any carbon atom on ring Cy.
Preferably, the second compound has any one of the structures shown as N1-N447:
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Preferably, the mass ratio of the first compound to the second compound is (0.1-2): 1, which may be, for example, 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1 or 1.9:1, etc., further preferably (0.8-2): 1.
In a second aspect, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer arranged between the first electrode and the second electrode, the organic layer comprising an electroluminescent material according to the first aspect.
Preferably, the organic layer comprises a light emitting layer comprising an electroluminescent material according to the first aspect.
Preferably, the electroluminescent material is used as a host material of the light emitting layer, the first compound is a first host material, and the second compound is a second host material.
As a preferred technical scheme of the invention, the electroluminescent material is used as a main material of a light-emitting layer, the first compound (first main material, P-type main material) has good hole transmission capability and a higher space accumulation structure, and the second compound (second main material, N-type main material) has higher molecular plane unfolding characteristic and good electron transmission performance. The two compounds are cooperatively compounded, so that the carrier compounding probability is improved, TPQ (polarization quenching) caused by corresponding polarons is also reduced, the carrier transmission balance is also reduced, the compound center position of electrons and holes in the luminescent layer is effectively regulated and controlled to be at the center position of the luminescent layer, the electron blocking layer is far away from, the hole blocking layer is also far away from, and a great deal of accumulation of carriers at an interface is avoided, so that the luminous efficiency of the device is obviously improved, and the service life is prolonged.
Preferably, the light emitting layer further includes a doping material therein.
Preferably, the mass percentage of the doping material in the light-emitting layer is 1-10%, for example, may be 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.
Preferably, the doping material is a phosphorescent doping material.
Preferably, the thickness of the light emitting layer is 10 to 60nm, for example, 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 28nm, 30nm, 32nm, 35nm, 38nm, 40nm, 42nm, 45nm, 48nm, 50nm, 52nm, 55nm, 58nm, or the like, and further preferably 20 to 50nm.
Preferably, the organic layer further includes any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron injection layer, a hole blocking layer, or an electron blocking layer.
In a preferred embodiment, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic layer may be a small organic molecule, a large organic molecule, or a polymer, and combinations thereof.
In a preferred embodiment, the organic electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode; the organic layer comprises a light-emitting layer, a hole transmission region arranged between the light-emitting layer and the anode, and an electron transmission region arranged between the light-emitting layer and the cathode; the luminescent layer comprises the electroluminescent material provided by the invention.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives; wherein the aromatic amine derivative includes compounds as shown below HT-1 to HT-52; or any combination thereof.
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The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-52 described above, or one or more of the compounds HI-1 through HI-3 described below; one or more compounds of HT-1 through HT-52 may also be used to dope one or more of HI-1 through HI-3 described below.
The luminescent layer comprises a Host material (electroluminescent material provided by the invention), and simultaneously comprises luminescent dyes (namely doping materials) capable of emitting different wavelength spectrums, and can be a monochromatic luminescent layer capable of emitting red, green, blue and other single colors. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
The luminescent layer material may be a phosphorescent electroluminescent material, according to different techniques. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In a preferred embodiment of the present invention, the material of the light emitting layer is a phosphorescent host material, and the phosphorescent host material is an electroluminescent material provided by the present invention, and the electroluminescent material includes a combination of a first compound and a second compound.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The phosphorescent dopant material of the light emitting layer thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
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Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The phosphor-doped material of the light emitting layer may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The phosphor doped material of the light emitting layer may be selected from, but not limited to, one or more combinations of YPD-1 through YPD-11 listed below.
The organic layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multi-layer structure including at least one of an Electron Injection Layer (EIL) and an Electron Transport Layer (ETL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-74 listed below.
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In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-74 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-74 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following: liQ, liF, naCl, csF, li 2O、Cs2CO3, baO, na, li, ca, mg or Yb.
In a third aspect, the present invention provides a display device comprising an organic electroluminescent device as described in the second aspect.
Compared with the prior art, the invention has the following beneficial effects:
In the electroluminescent material provided by the invention, through the structural design and the compounding synergy of the first compound and the second compound, the electroluminescent material has excellent photoelectric performance, and is suitable for a luminescent layer of an organic electroluminescent device, in particular to a main material. In the organic electroluminescent device containing the electroluminescent material, the electroluminescent material is used as a main material, so that the carrier recombination probability can be improved, the carrier transmission is balanced, the transmission balance of holes and electrons is realized, and the position of the electron and hole recombination center in the luminescent layer is regulated and controlled to occur at the central position of the luminescent layer, thereby effectively improving the luminous efficiency of the device, and greatly improving the stability and the service life of the device.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present invention;
the light-emitting diode comprises a 1-substrate, a 2-anode, a 3-hole injection layer, a 4-hole transmission layer, a 5-electron blocking layer, a 6-light-emitting layer, a 7-hole blocking layer, an 8-electron transmission layer, a 9-electron injection layer, a 10-cathode and an 11-external power supply.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
In the present invention, the first and second compounds may be prepared by methods disclosed in the prior art; illustratively, the preparation of the first compound may be referred to the disclosure in prior art CN103189469a and CN103555322 a; the preparation of the second compound can be referred to in the prior art CN113277988a and CN108463456a; and will not be described in detail.
Example 1-1
An electroluminescent material and an organic electroluminescent device comprising the same; the electroluminescent material comprises a combination of a first compound P5 and a second compound N10, wherein the mass ratio of the first compound P5 to the second compound N10 is 1:1.
The organic electroluminescent device containing the electroluminescent material is schematically shown in fig. 1, and comprises a substrate 1 (glass substrate), an anode 2 (ITO), a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 (Al cathode) which are laminated in sequence; an external power supply 11 is applied between the anode 2 and the cathode 10.
The organic matter electroluminescent light device fabrication the method comprises the following steps:
(1) Ultrasonic treating the glass substrate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in an acetone/ethanol mixed solvent, baking in a clean environment until the moisture is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;
(2) Placing the glass substrate with the anode in a vacuum cavity, vacuumizing to less than 1X 10 -5 Pa, and vacuum evaporating a mixture of a compound HT-4:HI-3 (97/3,w/w) on the anode layer film to serve as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the thickness of an evaporation film is 10nm;
(3) Vacuum evaporating a compound HT-4 on the hole injection layer as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 60nm;
(4) Vacuum evaporating a compound HT-52 on the hole transport layer as an electron blocking layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 60nm;
(5) Vacuum evaporating a light-emitting layer of the device on the electron blocking layer, wherein the mass percentage of the doped material in the light-emitting layer is 3% by means of a ternary mixture of a main material of the light-emitting layer (the electroluminescent material, p5:n10=1:1) and the doped material (dye, RPD-14); the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 40nm;
(6) Vacuum evaporating compound ET-74 on the luminous layer as a hole blocking layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 5nm;
(7) Vacuum evaporating a compound ET-69:ET-57 (50/50, w/w) mixture on the hole blocking layer as an electron transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 25nm;
(8) Vacuum evaporating LiF with the thickness of 1nm on the electron transport layer as an electron injection layer, wherein the evaporation rate is 0.1nm/s;
(9) Vacuum evaporating metal aluminum with the thickness of 150nm on the electron injection layer as a cathode, wherein the evaporation rate is 1nm/s; thus, an organic electroluminescent device of example 1-1 was obtained.
Examples 1-2 to 12-3, comparative examples 1 to 4
An electroluminescent material and an organic electroluminescent device comprising the same, which differ from example 1-1 only in that the electroluminescent material (host material of light-emitting layer) was replaced with the compounds in tables 1 and 2, and other structures, materials and preparation methods of the device were the same as those of example 1-1; the "first compound: second compound" in tables 1 and 2 represents the mass ratio of both.
Performance test of organic electroluminescent device:
Under the condition that the same brightness is 3000cd/m 2, the current density of the organic electroluminescent device is measured, and the ratio of the brightness to the current density is the current efficiency; the time taken for the device to decay from an initial luminance of 10000cd/m 2 to 9700cd/m 2 was recorded at a constant current to obtain a test value of LT97 lifetime.
The current efficiency and the LT97 life of the comparative example 1 are recorded as 1, and the current efficiency and the LT97 life of the other examples and the comparative examples are the ratios of the respective test values to the test value of the comparative example 1; the test results are shown in tables 1 and 2.
TABLE 1
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In table 1, "-" indicates that the compound was not added/the ratio was not present.
TABLE 2
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As can be seen from the above table data, the P-type host of the structure shown in formula I or the N-type host of the structure shown in formula II, when used alone, resulted in low luminous efficiency and short lifetime of the device due to serious imbalance in carrier transport (comparative examples 1 to 4). In table 1, a P-type main body (first compound) with a structure shown in formula I and an N-type main body (second compound) with a structure shown in formula II are selected as a mixed main body for a light-emitting layer, the first compound has good hole transmission performance, the second compound has good electron transmission performance, and the two compounds are matched and used together to balance the transmission of carriers in a mutual synergistic manner, so that the carriers are compounded in the center of the light-emitting layer, and the efficiency and the service life of the device are greatly improved. The two types of main materials are tested according to different proportions in table 2, and from the data, the matching proportion of the two main materials is adjusted, so that the data of the device is affected to a certain extent, the whole change range is not large, and the performance is still better than the effect when the main materials are independently used.
It can be seen that the electroluminescent material comprising the combination of the first compound and the second compound is used for the organic electroluminescent device, so that the luminous efficiency and the service life of the device can be effectively improved, and the reason is that when the first compound or the second compound is used alone, the luminous recombination center is close to a Hole Blocking Layer (HBL) or an Electron Blocking Layer (EBL) due to unbalanced carrier transmission, the service life of the device is shorter, and the efficiency is low; when the two are matched for use, the carriers are balanced, the recombination center of the light-emitting layer is far away from the EBL and the HBL, the service life is greatly prolonged, meanwhile, the carrier recombination probability is improved, the TPQ caused by corresponding polarons is also reduced, and the efficiency is greatly improved.
The applicant states that the electroluminescent material and the organic electroluminescent device comprising the same according to the present invention are illustrated by the above examples, but the present invention is not limited to, i.e. does not mean that the present invention has to be carried out in dependence of, the above process steps. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.
Claims (16)
1. An electroluminescent material, characterized in that the electroluminescent material comprises a combination of a first compound and a second compound;
the first compound has a structure as shown in formula I:
in the formula I, L 1、L2、L3 is independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene and substituted or unsubstituted C3-C30 heteroarylene;
Ar 2、Ar3 is independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
Ar 1 is
R 1、R2、R3、R4、R5、R6、R7、R8 is each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl;
one group of any two adjacent groups in R 1、R2、R3、R4 is connected into a ring A through a chemical bond, and the ring A is
* Represents the attachment site of the group;
R 9、R10、R11、R12 is each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl;
In R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12, at least one group of any adjacent two groups among other groups except the group forming the ring A is linked to form a ring by a chemical bond;
X, Y are each independently selected from any one of a single bond, NR A1, O, S or CR A2RA3, and the X and Y are not both single bonds;
R A1 is selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
R A2、RA3 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
The substituted substituents in formula I are each independently selected from at least one of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino;
The second compound has a structure as shown in formula II:
in the formula II, ar is selected from any one of substituted or unsubstituted C3-C30 nitrogen-containing heteroaryl;
l is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
Cy is a ring
The dashed line represents ring E as an optional structure;
ring E is selected from any one of a substituted or unsubstituted C6-C20 aromatic ring and a substituted or unsubstituted C3-C20 heteroaromatic ring;
R 21、R22 is each independently selected from any one of halogen, cyano, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
m 1 is an integer from 0 to 4, and m 2 is an integer from 0 to 6;
The substituted substituents in formula II are each independently selected from at least one of halogen, cyano, nitro, hydroxy, amino, aldehyde, ester, C1-C30 straight or branched alkyl, C1-C30 alkoxy, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, unsubstituted or R 'substituted C6-C30 aryl, unsubstituted or R' substituted C3-C30 heteroaryl;
Each R' is independently selected from at least one of halogen, cyano, unsubstituted or halogenated C1-C10 straight or branched alkyl, C6-C20 aryl or C3-C20 heteroaryl.
2. The electroluminescent material of claim 1, wherein each L 1、L2、L3 is independently selected from any one of a single bond, a substituted or unsubstituted C6-C20 arylene, a substituted or unsubstituted C6-C20 heteroarylene;
Preferably, each of said L 1、L2、L3 is independently selected from a single bond, Any one of them; wherein U is O or S, representing the attachment site of the group.
3. The electroluminescent material of claim 1, wherein each Ar 2、Ar3 is independently selected from any one of substituted or unsubstituted:
Wherein represents the attachment site of the group;
Each Z 1、Z2、Z3 is independently selected from any one of O, S, NR 32 or CR 33R34;
R 31、R32、R33、R34 is independently selected from any one of hydrogen, C1-C20 straight or branched chain alkyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino;
preferably, each R 31、R32、R33、R34 is independently selected from any one of C1-C6 straight or branched chain alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl or naphthylphenyl.
4. The electroluminescent material according to claim 1, wherein in ring a, X is selected from any one of NR A1, O, S or CR A2RA3, and Y is a single bond;
Preferably, ar 1 is selected from any one of the following groups a-f:
Wherein represents the attachment site of the group;
x is selected from any one of NR A1, O, S or CR A2RA3;
R A1 is selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
R A2、RA3 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12 Each independently selected from any one of hydrogen, halogen, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl;
In Ar 1, at least one group of adjacent R M and R M+1 are connected into a ring through chemical bonds, and M is an integer of 1-11;
Preferably, in Ar 1, at least one group of adjacent R M and R M+1 is connected to form a benzene ring through a chemical bond, and M is an integer from 1 to 11.
5. The electroluminescent material of claim 4, wherein Ar 1 is selected from any one of substituted or unsubstituted:
Wherein represents the attachment site of the group;
x is selected from any one of NR A1, O, S or CR A2RA3;
R A1 is selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
R A2、RA3 is independently selected from any one of hydrogen, substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
The substituted substituents are each independently selected from at least one of halogen, C1-C20 straight or branched chain alkyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino;
Preferably, the R A1 is selected from any one of substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl;
preferably, said R A1 is selected from Any one of them;
Preferably, each R A2、RA3 is independently selected from any one of hydrogen, C1-C6 straight or branched alkyl, phenyl.
6. The electroluminescent material of claim 1, wherein the first compound has any one of the following structures P1-P328:
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7. The electroluminescent material of claim 1, wherein in formula II, ar is selected from any one of substituted or unsubstituted C3-C10 nitrogen-containing heteroaryl groups;
Preferably, ar is selected from any one of the following groups:
wherein the dotted line represents the attachment site of the group;
R 41、R42 is independently selected from any one of hydrogen, halogen, cyano, C1-C30 straight or branched alkyl, unsubstituted or R 'substituted C6-C30 aryl, unsubstituted or R' substituted C3-C30 heteroaryl;
R 43 is independently selected from any one of halogen, cyano, C1-C30 straight or branched chain alkyl, unsubstituted or R 'substituted C6-C30 aryl, unsubstituted or R' substituted C3-C30 heteroaryl;
r' is independently selected from at least one of halogen, cyano, unsubstituted or halogenated C1-C10 linear or branched alkyl, C6-C20 aryl or C3-C20 heteroaryl;
n 1 is an integer from 0 to 3 and n 2 is an integer from 0 to 5.
8. The electroluminescent material of claim 1, wherein Ar is selected from any one of the following groups:
Wherein R 51、R52、R53 is each independently selected from hydrogen, />
* Representing the attachment site of the group.
9. The electroluminescent material of claim 1, wherein in formula II, L is selected from any one of a single bond, a substituted or unsubstituted C6-C20 arylene, a substituted or unsubstituted C5-C20 heteroarylene;
Preferably, L is selected from the group consisting of a single bond, Any one of them; * Representing the attachment site of the group.
10. The electroluminescent material of claim 1, wherein in formula II, the ring E is a benzene ring;
preferably, both m 1 and m 2 are 0;
Preferably, the ring Cy is
11. The electroluminescent material of claim 1, wherein the second compound has any one of the structures shown as N1-N447:
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12. Electroluminescent material according to claim 1, characterized in that the mass ratio of the first compound to the second compound is (0.1-2): 1, preferably (0.8-2): 1.
13. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises a first electrode, a second electrode and an organic layer arranged between the first electrode and the second electrode, the organic layer comprising the electroluminescent material according to any one of claims 1-12.
14. The organic electroluminescent device of claim 13, wherein the organic layer comprises a light-emitting layer comprising the electroluminescent material of any one of claims 1-12;
preferably, the electroluminescent material is used as a host material of the light emitting layer;
Preferably, the light-emitting layer further comprises a doping material;
preferably, the doping material is a phosphorescent doping material.
15. The organic electroluminescent device according to claim 14, wherein the thickness of the light emitting layer is 10-60nm, preferably 20-50nm;
preferably, the organic layer further includes any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron injection layer, a hole blocking layer, or an electron blocking layer.
16. A display device, characterized in that it comprises an organic electroluminescent device as claimed in any one of claims 13-15.
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