WO2022100634A1 - Organic electroluminescent device and display apparatus comprising same - Google Patents
Organic electroluminescent device and display apparatus comprising same Download PDFInfo
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- WO2022100634A1 WO2022100634A1 PCT/CN2021/129912 CN2021129912W WO2022100634A1 WO 2022100634 A1 WO2022100634 A1 WO 2022100634A1 CN 2021129912 W CN2021129912 W CN 2021129912W WO 2022100634 A1 WO2022100634 A1 WO 2022100634A1
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- heteroaryl
- independently selected
- aryl
- independently
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- 238000000605 extraction Methods 0.000 claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 238000002347 injection Methods 0.000 claims abstract description 40
- 239000007924 injection Substances 0.000 claims abstract description 40
- 230000005525 hole transport Effects 0.000 claims abstract description 28
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- 125000005549 heteroarylene group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 238000005401 electroluminescence Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- -1 anode electrode Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001975 deuterium Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000005551 pyridylene group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 104
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- 239000000463 material Substances 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 56
- 239000007787 solid Substances 0.000 description 38
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000000843 powder Substances 0.000 description 26
- 239000000376 reactant Substances 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000002019 doping agent Substances 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 17
- GEDOYYDMCZUHNW-UHFFFAOYSA-N 2-bromotriphenylene Chemical group C1=CC=C2C3=CC(Br)=CC=C3C3=CC=CC=C3C2=C1 GEDOYYDMCZUHNW-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 11
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
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- 238000000034 method Methods 0.000 description 8
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- BZUUVQCSPHPUQA-UHFFFAOYSA-N 2-bromo-5-chloropyridine Chemical compound ClC1=CC=C(Br)N=C1 BZUUVQCSPHPUQA-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000010408 film Substances 0.000 description 4
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- 101100491149 Caenorhabditis elegans lem-3 gene Proteins 0.000 description 3
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- 238000005406 washing Methods 0.000 description 3
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 2
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 2
- YNKYZLVAYQLGIE-UHFFFAOYSA-N 4-naphthalen-2-yl-n-(4-naphthalen-2-ylphenyl)aniline Chemical compound C1=CC=CC2=CC(C3=CC=C(C=C3)NC=3C=CC(=CC=3)C=3C=C4C=CC=CC4=CC=3)=CC=C21 YNKYZLVAYQLGIE-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910018068 Li 2 O Inorganic materials 0.000 description 2
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- QARVLSVVCXYDNA-RALIUCGRSA-N 1-bromo-2,3,4,5,6-pentadeuteriobenzene Chemical compound [2H]C1=C([2H])C([2H])=C(Br)C([2H])=C1[2H] QARVLSVVCXYDNA-RALIUCGRSA-N 0.000 description 1
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 1
- VCYJGRWERKUBFX-UHFFFAOYSA-N 4-(2-phenylphenyl)aniline Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1C1=CC=CC=C1 VCYJGRWERKUBFX-UHFFFAOYSA-N 0.000 description 1
- UDDATXIGLCWITG-UHFFFAOYSA-N 4-naphthalen-2-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(C=CC=C2)C2=C1 UDDATXIGLCWITG-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001680 brushing effect Effects 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
- 230000003247 decreasing effect Effects 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D269/00—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00
- C07D269/02—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00 having the hetero atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
Definitions
- the present application relates to the technical field of organic light-emitting displays, and in particular, to an organic electroluminescent device and a display device including the device.
- the organic electroluminescent device is a multilayer organic thin film structure in which the light-emitting layer is located between the cathode and the anode. After electrification, the light emitted by the light-emitting layer is transmitted from the transparent electrode side, and the light is lost due to the waveguide effect such as total reflection between each film layer. Adding a high refractive index light extraction layer on the transparent electrode can greatly improve the light extraction efficiency.
- the light extraction layer may be an inorganic compound or an organic compound.
- Inorganic compounds are characterized by a high refractive index, which is beneficial for light extraction, but the coating temperature is very high (>1000 degrees), which can cause damage to organic components.
- the evaporation temperature of organic thin films is low, and the technology has greater advantages than inorganic compounds.
- Organic electroluminescent diode (OLED) elements basically use organic light extraction materials that can improve the light extraction efficiency of OLEDs. Refractive index is the most important indicator of light extraction materials. Generally, the higher the refractive index of the light extraction layer, the higher the light extraction efficiency from the electrode to the light extraction layer, and the higher the luminous efficiency of the OLED.
- the material mainly used for the light extraction layer of OLED is an aromatic amine compound (CN103828485A) from Hodogaya, Japan.
- the refractive index of such compounds eg compounds 1-1 and 1-2
- a first aspect of the present application provides an organic electroluminescence device, comprising:
- the light extraction layer includes a compound of general formula (I):
- Ar 1 and Ar 2 are each independently selected from H atom, deuterium atom, halogen, C 6 -C 30 aryl group or C 3 -C 30 heteroaryl group, the hydrogen on the aryl group and the heteroaryl group
- Each atom can be independently substituted with Ra
- the heteroatoms on the heteroaryl group are each independently selected from O, S and N
- the Ra is each independently selected from deuterium, halogen, C 1 -C 6 alkyl, phenyl, biphenyl, terphenyl or naphthyl;
- L 1 , L 2 and L 3 are each independently selected from phenylene or pyridylene.
- a second aspect of the present application provides a display device comprising the organic electroluminescent device provided by the present application.
- the organic electroluminescent device provided by the present application includes a light extraction layer with a high refractive index, and takes advantage of the high refractive index of the light extraction layer to more effectively promote light extraction, thereby improving the luminous efficiency of the organic electroluminescent device.
- the display device provided by the present application has excellent display effect.
- FIG. 1 is a schematic diagram of an organic electroluminescent device according to an embodiment of the present application.
- a first aspect of the present application provides an organic electroluminescence device, comprising:
- the light extraction layer includes a compound of general formula (I):
- Ar 1 and Ar 2 are each independently selected from H atom, deuterium atom, halogen, C 6 -C 30 aryl group or C 3 -C 30 heteroaryl group, the hydrogen on the aryl group and the heteroaryl group
- Each atom can be independently substituted with Ra
- the heteroatoms on the heteroaryl group are each independently selected from O, S and N
- the Ra is each independently selected from deuterium, halogen, C 1 -C 6 alkyl, phenyl, biphenyl, terphenyl or naphthyl;
- L 1 , L 2 and L 3 are each independently selected from phenylene or pyridylene.
- said L 1 , L 2 and L 3 are each independently selected from the following groups:
- said Ar 1 and Ar 2 are each independently selected from the following groups:
- R 1 and R 2 are each independently selected from C 1 -C 6 alkyl, C 6 -C 12 aryl, or C 3 -C 12 heteroaryl.
- the Ar 1 is selected from the following groups:
- R 01 and R 02 are each independently selected from a C 1 -C 6 alkyl group, a C 6 -C 12 aryl group or a C 3 -C 12 heteroaryl group, and the heteroatom in the heteroaryl group is selected from O or S.
- the compound of general formula (I) may be selected from the following compounds:
- the hole transport layer comprises a compound of general formula (II):
- Ar 3 and Ar 4 are each independently selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group may each independently be substituted by Rb;
- R 3 -R 6 are each independently selected from hydrogen, deuterium, C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl base, the hydrogen atoms on the aryl group and the heteroaryl group can be independently substituted by Rb, and the two adjacent groups in the R 3 -R 6 can be connected to form a ring;
- R 7 and R 8 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl, said The hydrogen atoms on the aryl group and the heteroaryl group can each independently be replaced by Rb, and the R7 and R8 can be connected to form a ring;
- X is selected from O, S, CR 9 R 10 , NR 11 , R 9 and R 10 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 alkyl Aryl or C 3 -C 30 heteroaryl, the R 11 is selected from C 6 -C 30 aryl or C 3 -C 30 heteroaryl, the aryl and the hydrogen atom on the heteroaryl Each independently can be substituted by Rb, and said R 9 and R 10 can be linked to form a ring;
- L is selected from a chemical bond, a C 6 -C 30 arylene group or a C 3 -C 30 heteroarylene group, and each of the hydrogen atoms on the arylene group and the heteroarylene group independently may be substituted by Rb;
- heteroatoms on the heteroaryl or heteroarylene are each independently selected from O, S, N;
- the Rbs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
- the compound of general formula (II) may be selected from the following compounds:
- the electron transport layer comprises a compound of general formula (III):
- R 12 -R 17 are each independently selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, said aryl and heteroaryl
- the hydrogen atoms on each independently can be substituted by Rc, the adjacent two groups in the R 12 -R 14 can be connected to form a ring, and the R 16 and R 17 can be connected to form a ring;
- A is selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc;
- Y is selected from O, S, CR 18 R 19 , R 18 and R 19 are each independently selected from C 1 -C 6 alkyl, C 5 -C 20 cycloalkyl, C 6 -C 30 aryl or
- the heteroaryl group of C 3 -C 30 , the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc, and the R 18 and R 19 can be connected to form a ring;
- X 1 -X 4 are each independently selected from CR 20 or N, and R 20 is selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl , the hydrogen atoms on the aryl group and the heteroaryl group can be substituted by Rc independently, and the adjacent R 20 can be connected to form a ring;
- L 1 and L 2 are each independently selected from a chemical bond, a C 6 -C 30 arylene group, or a C 3 -C 30 heteroarylene group, and the hydrogen atoms on the arylene group and the heteroarylene group are each independently Can be replaced by Rc;
- heteroatoms on the heteroaryl group or the heteroarylene group are each independently selected from O, S, N;
- the Rcs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
- the compound of general formula (III) may be selected from the following compounds:
- organic electroluminescence device which may be organic electroluminescence devices of various types and structures known in the art.
- the organic electroluminescence device of the present application may be a light-emitting device with a top emission structure, and may include an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, Transparent or translucent cathodes and light extraction layer structures.
- the organic electroluminescent device of the present application may be a light-emitting device with a bottom-emitting structure, which may include a light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron Transport layer, electron injection layer and cathode electrode.
- the organic electroluminescent device of the present application may also be a light-emitting device with a double-sided light-emitting structure, which may include a light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, and a light-emitting layer on the substrate in this order. , electron transport layer, electron injection layer, transparent or semi-transparent cathode and light extraction layer.
- an electron blocking layer may also be provided between the hole transport layer and the light-emitting layer, and a hole blocking layer may be provided between the light-emitting layer and the electron transport layer.
- the above-mentioned layers may be added or omitted as long as the purpose of the present application is satisfied.
- FIG. 1 shows a schematic diagram of an organic electroluminescent device according to an embodiment of the present application, wherein, from bottom to top, a substrate 1, an anode electrode 2, a hole injection layer 3, a hole transport layer 4, and a light-emitting layer 5 are arranged in sequence. , an electron transport layer 6 , an electron injection layer 7 , a cathode electrode 8 and a light extraction layer 9 .
- FIG. 1 only schematically shows the structure of a typical organic electroluminescence device, and the present application is not limited to this structure.
- the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the prior art can be used, such as glass, polymer materials, glass and polymer materials with TFT components, and the like.
- the anode electrode 2 is not particularly limited, and can be selected from known anode electrodes in the prior art.
- metals, alloys or conductive compounds have a high work function (4 eV or greater).
- the metal may be metals such as Au and Ag.
- the conductive transparent material can be selected from materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO, or an amorphous material such as IDIXO (In 2 O 3 -ZnO) that can form a transparent conductive film is used.
- the thickness of the anode is in the range of 10 to 1,000 nm. Here, the thickness of the anode electrode varies depending on the material used.
- the material of the hole injection layer 3 is not particularly limited, and can be made of hole injection layer materials known in the art, for example, hole transport material (HTM) is selected as the hole injection material.
- HTM hole transport material
- the hole injection layer 3 may further include a p-type dopant.
- the type of the p-type dopant is not particularly limited, and various p-type dopants known in the art can be used. Dopants such as the following p-type dopants can be used:
- the amount of the p-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
- the hole transport layer 4 is not limited, and hole transport materials known to those skilled in the art can be used.
- the hole transport layer 4 may comprise at least one of the hole transport materials of the present application, or at least one of the hole transport materials of the present application and the following known hole transport materials A combination of at least one of HT-1 to HT-32.
- the material for the host of the hole injection layer and the material for the hole transport layer may be selected from at least one of the following HT-1 to HT-32 compounds:
- the light-emitting layer 5 may include a blue light-emitting layer, a green light-emitting layer or a red light-emitting layer.
- the light-emitting material in the light-emitting layer 5 is not particularly limited, and various light-emitting materials known to those skilled in the art can be used. Materials, for example, the luminescent material may comprise a host material and a luminescent dye.
- the blue light host material may be selected from at least one of the following BH-1 to BH-36 compounds:
- the green host material may be selected from at least one of the following GPH-1 to GPH-82 compounds:
- the red host material may be selected from at least one of the following RH-1 to RH-10 compounds:
- the light-emitting layer 5 adopts electroluminescence technology.
- the luminescent dye in its luminescent layer 5 is a fluorescent or phosphorescent dopant, and the dopant can be selected from, but not limited to, at least one of the following blue-light dyes BD01 to BD04 compounds, and at least one of green dyes GD01 to GD04 compounds.
- the amount of the dopant used is not particularly limited, and can be the amount known to those skilled in the art.
- the electron transport layer 6 is not particularly limited, and electron transport materials known to those skilled in the art can be used.
- the electron transport layer 6 contains at least one of the electron transport materials of the present application, and in another preferred embodiment, the electron transport layer 6 may also contain at least one of the electron transport materials of the present application A combination with at least one of the following known electron transport materials ET-1 to ET-58:
- the electron transport layer 6 may further include n-type dopants, the types of the n-type dopants are not particularly limited, and various n-type dopants known in the art can be used , for example the following n-type dopants can be used:
- the amount of the n-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
- the electron injection layer 7 is not particularly limited, and electron injection materials known in the art can be used, for example, including but not limited to LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 in the prior art At least one of CO 3 , BaO, Na, Li, Ca and other materials.
- the cathode electrode 8 is not particularly limited, and can be selected from, but not limited to, magnesium-silver mixture, LiF/Al, ITO, Al and other metals, metal mixtures, oxides and other materials.
- the light extraction layer 9 includes at least one of the light extraction layers of the present application, and the light extraction layer 9 may also include at least one of the light extraction layers of the present application and known light extraction layers.
- known light extraction layers are mainly light extraction layers containing aromatic amine compounds.
- the light extraction layer of the present application is arranged on the transparent electrode on the light extraction side. It is required that the refractive index of the light extraction layer is larger than that of the electrode and can transmit visible light.
- the light extraction layer of the present application has a higher refractive index, and thus can provide a high light extraction rate.
- the refractive index of the light extraction layer of the present application is >1.85.
- the refractive index of red light of the above-mentioned light extraction layer is greater than or equal to 1.85, the refractive index of green light is greater than or equal to 1.90, and the refractive index of blue light is greater than or equal to 2.00.
- the thickness of the light extraction layer is 50-90 nm, preferably 60-80 nm.
- the present application also provides a display device comprising the organic electroluminescent device of the present application.
- the display device includes, but is not limited to, a display, a television, a mobile communication terminal, a tablet computer, and the like.
- the method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art can be used.
- the present application can be prepared by the following preparation method:
- An electron injection material is vacuum-evaporated on the electron transport layer 6 as the electron injection layer 7, and the electron injection material is selected from LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca at least one of the other materials;
- vacuum evaporation cathode material is used as cathode electrode 8 on electron injection layer 7;
- a reflective anode electrode is arranged on the glass substrate, the anode electrode is an ITO electrode, and the thickness of the electrode is 130 nm;
- a hole injection layer with a thickness of 10 nm was vacuum evaporated on the anode electrode.
- the material of the hole injection layer was HT-11 and a p-type dopant p-1 with a mass ratio of 3%, wherein the evaporation rate was 0.1 nm/s, the selected hole injection layer materials and p-type dopants are the following materials:
- a hole transport layer with a thickness of 112 nm was vacuum evaporated on the hole injection layer, and the material of the hole transport layer was the above-mentioned HT-32, wherein the evaporation rate was 0.1 nm/s;
- a light-emitting layer is vacuum-evaporated on the hole transport layer, and the light-emitting layer includes a host material BH-1 and a light-emitting dye BD-1, and is vapor-deposited by a multi-source co-evaporation method, wherein the host material BH-1 is adjusted
- the evaporation rate is 0.1nm/s
- the evaporation rate of dye BD-1 is 3% of the evaporation rate of the host material
- the total film thickness of evaporation is 20nm
- the host material and the luminescent dye are the following materials:
- the electron transport layer contained an electron transport material ET-58 and an n-type dopant n-1, wherein the content of the n-type dopant was 50 mol%.
- the electron transport materials and n-type dopants are the following materials:
- an electron injection layer with a thickness of 40 nm is vacuum-evaporated on the electron transport layer, and the material of the electron injection layer is Liq (8-hydroxyquinoline-lithium), and the evaporation rate is 0.1 nm/s;
- a cathode electrode with a thickness of 18 nm is vacuum-evaporated on the electron injection layer, and the cathode electrode is composed of a cathode material with a Mg:Ag molar ratio of 1:9, and the evaporation rate is 1 nm/s;
- a light extraction layer with a thickness of 50 nm was vacuum evaporated on the cathode electrode, and the material of the light extraction layer was LEM-1.
- the organic electroluminescent device of this embodiment emits blue light.
- the organic electroluminescent device of this embodiment emits green light.
- Example 2 The rest is the same as Example 1, except that the light-emitting host material and the light-emitting dye are replaced by RH-10 and RPD-1, respectively.
- the organic electroluminescent device of this embodiment emits red light.
- Example 31 The same as in Example 31, except that the hole transport material was replaced by B6 and the electron transport material was replaced by C27 as shown in Table 1.
- the measuring instrument is Version-1.0.1.4 spectroscopic ellipsometer of _Radiation technology company; the size of the glass substrate is 200mm ⁇ 200mm, and the thickness of the material film is 80nm. The refractive index of the compound was measured at different wavelengths.
- the BJV test system was used to test the current efficiency and CIE color coordinates of the organic electroluminescent device.
- the blue light index (BI) is used to investigate the luminous efficiency, and the CIEy value mainly evaluates the saturation of the blue light color.
- the blue light index is obtained by dividing the current efficiency of the blue light device by the CIEy value. The larger the CIEy value, the red shift of the blue color. , the decrease of CIEy value indicates the blue shift of blue color; the current efficiency is used to evaluate the luminous efficiency of green and red devices; the color change of green and red devices is mainly evaluated by the CIEx value, and the increase of CIEx indicates the red shift of luminescence , CIEx becomes smaller, indicating a blue-shift of luminescence.
- the blue light index changed from 92 to 76, which decreased by 16, and the CIEy changed from 0.050 to 0.070, which increased by 0.020, indicating that the blue light changed to red.
- the blue light index changes from 96 to 83, a decrease of 7, and the CIEy changes from 0.051 to 0.063, an increase of 7.
- the blue light index of compound 1-1 is smaller than that of compound LEM-1, and the CIEy of compound 1-1 is larger than that of compound LEM-1, indicating that the blue light of the blue light device of LEM-1 Color saturation is higher.
- the thickness of the light extraction layer is increased from 50nm to 90nm, the current efficiency is changed from 97cd/A to 101cd/A, an increase of 4cd/A, and the CIEx is changed from 0.235 to 0.250, an increase of 0.015
- the current efficiency changed from 99cd/A to 106cd/A, an increase of 7cd/A, and the CIEx changed from 0.234 to 0.243, an increase of 0.009.
- the thickness of the light extraction layer increased from 50nm to 90nm
- the current efficiency increased from 46cd/A to 53cd/A, an increase of 7cd/A
- the CIEx increased from 0.665 to 0.675, an increase of 0.010
- the current efficiency changed from 48cd/A to 61cd/A, an increase of 13cd/A
- the CIEx changed from 0.665 to 0.676, an increase of 0.011.
- compound LEM-1 as a light extraction material can make the device emit light. Higher color saturation and greater current efficiency.
- Examples 40-46 used the compounds provided in this application as hole injection materials and electron transport materials, respectively.
- the blue light devices using these materials were compared with the comparative examples with the same thickness of the light extraction layer. It can be seen that the blue light index increased significantly. , CIEy decreases.
- the compounds provided by the present application are used in the light extraction layer of organic electroluminescent devices, and the refractive indices of blue light, green light and red light are significantly improved, Therefore, light extraction can be more effectively promoted, a high light extraction rate can be provided, and the luminous efficiency of the organic electroluminescent device can be greatly improved.
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Abstract
Provided are an organic electroluminescent device and a display apparatus comprising same. The organic electroluminescent device comprises a substrate, an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electronic transport layer, an electronic injection layer, a cathode electrode, and a light extraction layer; and the light extraction layer comprises a compound of general formula (I), has a high refractive index, and can improve light-emitting efficiency of the organic electroluminescent device.
Description
本申请要求于2020年11月12日提交中国专利局、申请号为202011260930.2发明名称为“一种有机电致发光器件及包含该器件的显示装置”的中国专利申请，以及2021年1月12日提交中国专利局、申请号为202110034259.8发明名称为“一种有机电致发光器件及包含该器件的显示装置”的中国专利申请的优先权，其全部内容通过引用结合在本申请中。This application requires a Chinese patent application with an application number of 202011260930.2 entitled "An organic electroluminescent device and a display device including the same" to be filed with the China Patent Office on November 12, 2020, and January 12, 2021 The priority of the Chinese patent application filed with the Chinese Patent Office with the application number of 202110034259.8 and the invention title is "An organic electroluminescent device and a display device including the same", the entire contents of which are incorporated herein by reference.
本申请涉及有机发光显示技术领域，特别是涉及一种有机电致发光器件及包含该器件的显示装置。The present application relates to the technical field of organic light-emitting displays, and in particular, to an organic electroluminescent device and a display device including the device.
有机电致发光器件是一种多层有机薄膜结构，其中发光层位于阴阳极之间。通电后发光层发出的光从透明电极一侧透射出来，光由于在各个膜层之间发生全反射等波导效应而损失。在透明电极上增加一层高折射率的光提取层，可以大幅提高出光效率。The organic electroluminescent device is a multilayer organic thin film structure in which the light-emitting layer is located between the cathode and the anode. After electrification, the light emitted by the light-emitting layer is transmitted from the transparent electrode side, and the light is lost due to the waveguide effect such as total reflection between each film layer. Adding a high refractive index light extraction layer on the transparent electrode can greatly improve the light extraction efficiency.
光提取层可以是无机化合物，也可以是有机化合物。无机化合物的特点在于折射率高，有利光提取，但是镀膜温度很高(>1000度)，这种镀膜会对有机元器件造成损坏。有机物薄膜蒸镀温度低，工艺上比无机化合物具有更大优势。有机电致发光二极管(OLED)元件基本都使用能够提升OLED光取出效率的有机光提取材料。折射率是光提取材料最重要的指标，通常光提取层的折射率越高，则从电极到光提取层出光效率越高，OLED的发光效率越高。The light extraction layer may be an inorganic compound or an organic compound. Inorganic compounds are characterized by a high refractive index, which is beneficial for light extraction, but the coating temperature is very high (>1000 degrees), which can cause damage to organic components. The evaporation temperature of organic thin films is low, and the technology has greater advantages than inorganic compounds. Organic electroluminescent diode (OLED) elements basically use organic light extraction materials that can improve the light extraction efficiency of OLEDs. Refractive index is the most important indicator of light extraction materials. Generally, the higher the refractive index of the light extraction layer, the higher the light extraction efficiency from the electrode to the light extraction layer, and the higher the luminous efficiency of the OLED.
目前主要用于OLED光提取层的材料是日本保土谷的芳族胺化合物(CN103828485A)。该类化合物(例如化合物1-1和1-2)的折射率依然有待提高。At present, the material mainly used for the light extraction layer of OLED is an aromatic amine compound (CN103828485A) from Hodogaya, Japan. The refractive index of such compounds (eg compounds 1-1 and 1-2) still needs to be improved.
发明内容SUMMARY OF THE INVENTION
鉴于现有技术的上述问题，本申请的目的在于提供一种有机电致发光器件，其具有高的发光效率。本申请第一方面提供了一种有机电致发光器件，包括：In view of the above problems in the prior art, the purpose of the present application is to provide an organic electroluminescence device with high luminous efficiency. A first aspect of the present application provides an organic electroluminescence device, comprising:
基板、阳极电极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、阴极电极和光提取层；Substrate, anode electrode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer, cathode electrode and light extraction layer;
所述光提取层包括通式(I)的化合物：The light extraction layer includes a compound of general formula (I):
其中，Ar
1和Ar
2各自独立地选自H原子、氘原子、卤素、C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Ra取代，所述杂芳基上的杂原子各自独立地选自O、S和N，所述Ra各自独立地选自氘、卤素、C
1-C
6的烷基、苯基、联苯基、三联苯基或萘基；
Wherein, Ar 1 and Ar 2 are each independently selected from H atom, deuterium atom, halogen, C 6 -C 30 aryl group or C 3 -C 30 heteroaryl group, the hydrogen on the aryl group and the heteroaryl group Each atom can be independently substituted with Ra, the heteroatoms on the heteroaryl group are each independently selected from O, S and N, and the Ra is each independently selected from deuterium, halogen, C 1 -C 6 alkyl, phenyl, biphenyl, terphenyl or naphthyl;
L
1、L
2和L
3各自独立地选自亚苯基或亚吡啶基。
L 1 , L 2 and L 3 are each independently selected from phenylene or pyridylene.
本申请第二方面提供了一种显示装置，其包含本申请所提供的有机电致发光器件。A second aspect of the present application provides a display device comprising the organic electroluminescent device provided by the present application.
本申请提供的有机电致发光器件，包括高折射率的光提取层，利用光提取层折射率高的优点，更加有效地促进光取出，从而提升了有机电致发光器件的发光效率。本申请提供的显示装置具有优良的显示效果。The organic electroluminescent device provided by the present application includes a light extraction layer with a high refractive index, and takes advantage of the high refractive index of the light extraction layer to more effectively promote light extraction, thereby improving the luminous efficiency of the organic electroluminescent device. The display device provided by the present application has excellent display effect.
当然，实施本申请的任一产品或方法并不一定需要同时达到以上所述的所有优点。Of course, implementing any product or method of the present application does not necessarily require achieving all of the advantages described above at the same time.
为了更清楚地说明本申请实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本申请 的一种实施方式，对于本领域普通技术人员来讲，还可以根据这些附图获得其他的实施方式。In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the following briefly introduces the accompanying drawings required for the description of the embodiments or the prior art. Obviously, the drawings in the following description are only It is an embodiment of the present application, and for those of ordinary skill in the art, other embodiments can also be obtained according to these drawings.
图1为本申请一种实施方式的有机电致发光器件示意图。FIG. 1 is a schematic diagram of an organic electroluminescent device according to an embodiment of the present application.
下面将结合附图，对本申请中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本申请一部分实施例，而不是全部的实施例。本领域普通技术人员基于本申请中的实施例所获得的所有其他实施例，都属于本申请保护的范围。The technical solutions in the present application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments in the present application fall within the protection scope of the present application.
本申请第一方面提供了一种有机电致发光器件，包括：A first aspect of the present application provides an organic electroluminescence device, comprising:
基板、阳极电极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、阴极电极和光提取层；Substrate, anode electrode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer, cathode electrode and light extraction layer;
所述光提取层包括通式(I)的化合物：The light extraction layer includes a compound of general formula (I):
其中，Ar
1和Ar
2各自独立地选自H原子、氘原子、卤素、C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Ra取代，所述杂芳基上的杂原子各自独立地选自O、S和N，所述Ra各自独立地选自氘、卤素、C
1-C
6的烷基、苯基、联苯基、三联苯基或萘基；
Wherein, Ar 1 and Ar 2 are each independently selected from H atom, deuterium atom, halogen, C 6 -C 30 aryl group or C 3 -C 30 heteroaryl group, the hydrogen on the aryl group and the heteroaryl group Each atom can be independently substituted with Ra, the heteroatoms on the heteroaryl group are each independently selected from O, S and N, and the Ra is each independently selected from deuterium, halogen, C 1 -C 6 alkyl, phenyl, biphenyl, terphenyl or naphthyl;
L
1、L
2和L
3各自独立地选自亚苯基或亚吡啶基。
L 1 , L 2 and L 3 are each independently selected from phenylene or pyridylene.
优选地，所述L
1、L
2和L
3各自独立地选自以下基团：
Preferably, said L 1 , L 2 and L 3 are each independently selected from the following groups:
图中*表示连接位点。* in the figure indicates the ligation site.
优选地，所述Ar
1和Ar
2各自独立地选自以下基团：
Preferably, said Ar 1 and Ar 2 are each independently selected from the following groups:
其中，in,
R
1和R
2各自独立地选自C
1-C
6的烷基、C
6-C
12的芳基或C
3-C
12的杂芳基。
R 1 and R 2 are each independently selected from C 1 -C 6 alkyl, C 6 -C 12 aryl, or C 3 -C 12 heteroaryl.
更优选地，所述Ar
1选自以下基团：
More preferably, the Ar 1 is selected from the following groups:
其中，in,
R
01和R
02各自独立地选自C
1-C
6的烷基、C
6-C
12的芳基或C
3-C
12的杂芳基，且杂芳基中的杂原子选自O或S。
R 01 and R 02 are each independently selected from a C 1 -C 6 alkyl group, a C 6 -C 12 aryl group or a C 3 -C 12 heteroaryl group, and the heteroatom in the heteroaryl group is selected from O or S.
例如，所述通式(I)的化合物可以选自以下化合物：For example, the compound of general formula (I) may be selected from the following compounds:
优选地，所述空穴传输层包括通式(II)的化合物：Preferably, the hole transport layer comprises a compound of general formula (II):
其中，in,
Ar
3和Ar
4各自独立地选自C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代；
Ar 3 and Ar 4 are each independently selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group may each independently be substituted by Rb;
R
3-R
6各自独立地选自氢、氘、C
1-C
10的烷基、C
3-C
6的环烷基、C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代，所述R
3-R
6中相邻的 两个基团能够连接成环；
R 3 -R 6 are each independently selected from hydrogen, deuterium, C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl base, the hydrogen atoms on the aryl group and the heteroaryl group can be independently substituted by Rb, and the two adjacent groups in the R 3 -R 6 can be connected to form a ring;
R
7和R
8各自独立地选自C
1-C
10的烷基、C
3-C
6的环烷基、C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代，所述R
7和R
8能够连接成环；
R 7 and R 8 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl, said The hydrogen atoms on the aryl group and the heteroaryl group can each independently be replaced by Rb, and the R7 and R8 can be connected to form a ring;
X选自O、S、CR
9R
10、NR
11，R
9和R
10各自独立地选自C
1-C
10的烷基、C
3-C
6的环烷基、C
6-C
30的芳基或C
3-C
30的杂芳基，所述R
11选自C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代，所述R
9和R
10能够连接成环；
X is selected from O, S, CR 9 R 10 , NR 11 , R 9 and R 10 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 alkyl Aryl or C 3 -C 30 heteroaryl, the R 11 is selected from C 6 -C 30 aryl or C 3 -C 30 heteroaryl, the aryl and the hydrogen atom on the heteroaryl Each independently can be substituted by Rb, and said R 9 and R 10 can be linked to form a ring;
L选自化学键、C
6-C
30的亚芳基或C
3-C
30的亚杂芳基，所述亚芳基和亚杂芳基上的氢原子各自独立地可以被Rb取代；
L is selected from a chemical bond, a C 6 -C 30 arylene group or a C 3 -C 30 heteroarylene group, and each of the hydrogen atoms on the arylene group and the heteroarylene group independently may be substituted by Rb;
所述杂芳基或亚杂芳基上的杂原子各自独立地选自O、S、N；The heteroatoms on the heteroaryl or heteroarylene are each independently selected from O, S, N;
所述Rb各自独立地选自氘、卤素、硝基、氰基、C
1-C
4的烷基、苯基、联苯基、三联苯基或萘基。
The Rbs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
例如，所述通式(II)的化合物可以选自以下化合物：For example, the compound of general formula (II) may be selected from the following compounds:
优选地，所述电子传输层包含通式(III)的化合物：Preferably, the electron transport layer comprises a compound of general formula (III):
其中，in,
R
12-R
17各自独立地选自氢、氘、C
1-C
6的烷基、C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代，所述R
12-R
14中相邻的两个基团能够连接成环，所述R
16和R
17能够连接成环；
R 12 -R 17 are each independently selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, said aryl and heteroaryl The hydrogen atoms on each independently can be substituted by Rc, the adjacent two groups in the R 12 -R 14 can be connected to form a ring, and the R 16 and R 17 can be connected to form a ring;
A选自C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代；
A is selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc;
Y选自O、S、CR
18R
19，R
18和R
19各自独立地选自C
1-C
6的烷基、C
5-C
20的环烷基、C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代，所述R
18和R
19能够连接成环；
Y is selected from O, S, CR 18 R 19 , R 18 and R 19 are each independently selected from C 1 -C 6 alkyl, C 5 -C 20 cycloalkyl, C 6 -C 30 aryl or The heteroaryl group of C 3 -C 30 , the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc, and the R 18 and R 19 can be connected to form a ring;
X
1-X
4各自独立地选自CR
20或N，R
20选自氢、氘、C
1-C
6的烷基、C
6-C
30的芳基或C
3-C
30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代，且相邻的R
20能够连接成环；
X 1 -X 4 are each independently selected from CR 20 or N, and R 20 is selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl , the hydrogen atoms on the aryl group and the heteroaryl group can be substituted by Rc independently, and the adjacent R 20 can be connected to form a ring;
L
1和L
2各自独立地选自化学键、C
6-C
30的亚芳基或C
3-C
30的亚杂芳基，所述亚芳基和亚杂芳基上的氢原子各自独立地可以被Rc取代；
L 1 and L 2 are each independently selected from a chemical bond, a C 6 -C 30 arylene group, or a C 3 -C 30 heteroarylene group, and the hydrogen atoms on the arylene group and the heteroarylene group are each independently Can be replaced by Rc;
所述杂芳基或所述亚杂芳基上的杂原子各自独立地选自O、S、N；The heteroatoms on the heteroaryl group or the heteroarylene group are each independently selected from O, S, N;
所述Rc各自独立地选自氘、卤素、硝基、氰基、C
1-C
4的烷基、苯基、联苯基、三联苯基或萘基。
The Rcs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl.
例如，所述通式(III)的化合物可以选自以下化合物：For example, the compound of general formula (III) may be selected from the following compounds:
在本申请中，对于有机电致发光器件的种类和结构没有特别限制，可以为本领域公知的各种类型和结构的有机电致发光器件。In the present application, there is no particular limitation on the type and structure of the organic electroluminescence device, which may be organic electroluminescence devices of various types and structures known in the art.
本申请的有机电致发光器件，可以是顶部发光结构的发光器件，可以举出在基板上依次包含阳极电极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、透明或半透明阴极以及光提取层结构。The organic electroluminescence device of the present application may be a light-emitting device with a top emission structure, and may include an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, Transparent or translucent cathodes and light extraction layer structures.
本申请的有机电致发光器件，可以是底部发光结构的发光器件，可以举出在基板上依 次包含光提取层、透明或半透明阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层及阴极电极。The organic electroluminescent device of the present application may be a light-emitting device with a bottom-emitting structure, which may include a light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron Transport layer, electron injection layer and cathode electrode.
本申请的有机电致发光器件，还可以是双侧发光结构的发光器件，可以举出在基板上依次包含光提取层、透明或半透明阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、透明或半透明阴极以及光提取层。The organic electroluminescent device of the present application may also be a light-emitting device with a double-sided light-emitting structure, which may include a light extraction layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, and a light-emitting layer on the substrate in this order. , electron transport layer, electron injection layer, transparent or semi-transparent cathode and light extraction layer.
在本申请的一些实施方式中，还可以在空穴传输层和发光层之间设置有电子阻挡层，在发光层与电子传输层之间设置有空穴阻挡层，本领域技术人员可以根据实际情况增加或省略上述各层，只要满足本申请目的即可。In some embodiments of the present application, an electron blocking layer may also be provided between the hole transport layer and the light-emitting layer, and a hole blocking layer may be provided between the light-emitting layer and the electron transport layer. The above-mentioned layers may be added or omitted as long as the purpose of the present application is satisfied.
图1示出了本申请一种实施方式的有机电致发光器件示意图，其中，从下到上，依次设置基板1、阳极电极2、空穴注入层3、空穴传输层4、发光层5、电子传输层6、电子注入层7、阴极电极8和光提取层9。1 shows a schematic diagram of an organic electroluminescent device according to an embodiment of the present application, wherein, from bottom to top, a substrate 1, an anode electrode 2, a hole injection layer 3, a hole transport layer 4, and a light-emitting layer 5 are arranged in sequence. , an electron transport layer 6 , an electron injection layer 7 , a cathode electrode 8 and a light extraction layer 9 .
可以理解，图1仅示意性地示出了一种典型的有机电致发光器件的结构，本申请并不限于这种结构。It can be understood that FIG. 1 only schematically shows the structure of a typical organic electroluminescence device, and the present application is not limited to this structure.
为了方便起见，以下参照图1对本申请的有机电致发光器件进行说明，但这并不意味着对本申请保护范围的任何限定。For convenience, the organic electroluminescent device of the present application will be described below with reference to FIG. 1 , but this does not imply any limitation on the protection scope of the present application.
在本申请中，所述基板1没有特别限制，可以使用现有技术中有机电致发光器件所用的常规基板，例如，玻璃、聚合物材料、带有TFT元器件的玻璃和聚合物材料等。In this application, the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the prior art can be used, such as glass, polymer materials, glass and polymer materials with TFT components, and the like.
在本申请中，所述阳极电极2没有特别限制，可以选自现有技术中已知的阳极电极。例如，金属、合金或导电化合物具有高功函数(4eV或大于4eV)。其中，金属可以为Au、Ag等金属。导电透明材料可以选自CuI、氧化铟锡(ITO)、SnO
2和ZnO等材料，或者使用可以形成透明导电膜的非晶形材料如IDIXO(In
2O
3-ZnO)。阳极的厚度在10到1,000nm的范围内。其中，阳极电极的厚度根据所用材料而变化。
In the present application, the anode electrode 2 is not particularly limited, and can be selected from known anode electrodes in the prior art. For example, metals, alloys or conductive compounds have a high work function (4 eV or greater). The metal may be metals such as Au and Ag. The conductive transparent material can be selected from materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO, or an amorphous material such as IDIXO (In 2 O 3 -ZnO) that can form a transparent conductive film is used. The thickness of the anode is in the range of 10 to 1,000 nm. Here, the thickness of the anode electrode varies depending on the material used.
在本申请中，所述空穴注入层3的材料没有特别限制，可以使用本领域公知的空穴注入层材料制成，例如选用空穴传输材料(HTM)作为空穴注入材料。In this application, the material of the hole injection layer 3 is not particularly limited, and can be made of hole injection layer materials known in the art, for example, hole transport material (HTM) is selected as the hole injection material.
在一种优选的实施方案中，所述空穴注入层3还可以包括p型掺杂剂，所述p型掺杂剂的种类没有特别限制，可以采用本领域已知的各种p型掺杂剂，例如可以采用以下p型掺杂剂：In a preferred embodiment, the hole injection layer 3 may further include a p-type dopant. The type of the p-type dopant is not particularly limited, and various p-type dopants known in the art can be used. Dopants such as the following p-type dopants can be used:
在本申请中，所述p型掺杂剂用量没有特别限制，可以为本领域技术人员公知的用量。In the present application, the amount of the p-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
在本申请中，所述空穴传输层4没有任何限制，可以使用本领域技术人员公知的空穴传输材料。在一个优选的实施方案中，空穴传输层4可以包含本申请的空穴传输材料中的至少一种，或者包含本申请的空穴传输材料中的至少一种与以下已知空穴传输材料HT-1至HT-32中的至少一种的组合。In the present application, the hole transport layer 4 is not limited, and hole transport materials known to those skilled in the art can be used. In a preferred embodiment, the hole transport layer 4 may comprise at least one of the hole transport materials of the present application, or at least one of the hole transport materials of the present application and the following known hole transport materials A combination of at least one of HT-1 to HT-32.
例如，用于空穴注入层主体的材料和用于空穴传输层的材料可以选自以下HT-1至HT-32化合物中的至少一种：For example, the material for the host of the hole injection layer and the material for the hole transport layer may be selected from at least one of the following HT-1 to HT-32 compounds:
在本申请中，所述发光层5可以包含蓝光发光层、绿光发光层或红光发光层，所述发光层5中的发光材料没有特别限制，可以使用本领域技术人员公知的各种发光材料，例如，所述发光材料可以包含主体材料和发光染料。In this application, the light-emitting layer 5 may include a blue light-emitting layer, a green light-emitting layer or a red light-emitting layer. The light-emitting material in the light-emitting layer 5 is not particularly limited, and various light-emitting materials known to those skilled in the art can be used. Materials, for example, the luminescent material may comprise a host material and a luminescent dye.
在一个优选的实施方案中，蓝光主体材料可以选自以下BH-1至BH-36化合物中的至少一种：In a preferred embodiment, the blue light host material may be selected from at least one of the following BH-1 to BH-36 compounds:
在一个优选的实施方案中，绿光主体材料可以选自以下GPH-1至GPH-82化合物中的至少一种：In a preferred embodiment, the green host material may be selected from at least one of the following GPH-1 to GPH-82 compounds:
在一个优选的实施方案中，红光主体材料可以选自以下RH-1至RH-10化合物中的至少一种：In a preferred embodiment, the red host material may be selected from at least one of the following RH-1 to RH-10 compounds:
在本申请的一个优选的实施方案中，所述发光层5采用电致发光的技术。其发光层5中的发光染料为荧光或磷光掺杂剂，所述掺杂剂可以选自但不限于以下蓝光染料BD01至BD04化合物中的至少一种、绿光染料GD01至GD04化合物中的至少一种或红光染料RPD-1至RPD-28化合物中的至少一种。所述掺杂剂的用量没有特别限制，可以为本领域技术人员公知的用量。In a preferred embodiment of the present application, the light-emitting layer 5 adopts electroluminescence technology. The luminescent dye in its luminescent layer 5 is a fluorescent or phosphorescent dopant, and the dopant can be selected from, but not limited to, at least one of the following blue-light dyes BD01 to BD04 compounds, and at least one of green dyes GD01 to GD04 compounds. One or at least one of the red dyes RPD-1 to RPD-28 compounds. The amount of the dopant used is not particularly limited, and can be the amount known to those skilled in the art.
在本申请中，所述电子传输层6没有特别限制，可以使用本领域技术人员公知的电子传输材料。在一个优选的实施方案中，电子传输层6包含本申请的电子传输材料中的至少一种，在另一个优选的实施方案中，电子传输层6也可以包含本申请的电子传输材料中的至少一种与以下已知电子传输材料ET-1至ET-58中的至少一种的组合：In the present application, the electron transport layer 6 is not particularly limited, and electron transport materials known to those skilled in the art can be used. In a preferred embodiment, the electron transport layer 6 contains at least one of the electron transport materials of the present application, and in another preferred embodiment, the electron transport layer 6 may also contain at least one of the electron transport materials of the present application A combination with at least one of the following known electron transport materials ET-1 to ET-58:
在一个优选的实施方案中，所述电子传输层6还可以包括n型掺杂剂，所述n型掺杂剂 的种类没有特别限制，可以采用本领域已知的各种n型掺杂剂，例如可以采用以下n型掺杂剂：In a preferred embodiment, the electron transport layer 6 may further include n-type dopants, the types of the n-type dopants are not particularly limited, and various n-type dopants known in the art can be used , for example the following n-type dopants can be used:
在本申请中，所述n型掺杂剂用量没有特别限制，可以为本领域技术人员公知的用量。In the present application, the amount of the n-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
在本申请中，所述电子注入层7没有特别限制，可以使用本领域公知的电子注入材料，例如，可以包括但不限于现有技术中LiQ、LiF、NaCl、CsF、Li
2O、Cs
2CO
3、BaO、Na、Li、Ca等材料中的至少一种。
In the present application, the electron injection layer 7 is not particularly limited, and electron injection materials known in the art can be used, for example, including but not limited to LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 in the prior art At least one of CO 3 , BaO, Na, Li, Ca and other materials.
在本申请中，所述阴极电极8没有特别限制，可以选自但不限于镁银混合物、LiF/Al、ITO、Al等金属、金属混合物、氧化物等材料。In this application, the cathode electrode 8 is not particularly limited, and can be selected from, but not limited to, magnesium-silver mixture, LiF/Al, ITO, Al and other metals, metal mixtures, oxides and other materials.
在本申请中，所述光提取层9包含本申请的光提取层中的至少一种，所述光提取层9也可以包含本申请的光提取层中的至少一种与已知光提取层的组合。目前已知的光提取层主要为包含芳族胺化合物的光提取层。其中，为了提高出光率，本申请的光提取层设置在出光侧的透明电极上。要求光提取层的折射率大于电极的折射率，并且可以透过可见光。本申请的光提取层具有较高的折射率，因此可以提供高的出光率。优选地，本申请的光提取层的折射率＞1.85。In the present application, the light extraction layer 9 includes at least one of the light extraction layers of the present application, and the light extraction layer 9 may also include at least one of the light extraction layers of the present application and known light extraction layers. The combination. Currently known light extraction layers are mainly light extraction layers containing aromatic amine compounds. Wherein, in order to improve the light extraction rate, the light extraction layer of the present application is arranged on the transparent electrode on the light extraction side. It is required that the refractive index of the light extraction layer is larger than that of the electrode and can transmit visible light. The light extraction layer of the present application has a higher refractive index, and thus can provide a high light extraction rate. Preferably, the refractive index of the light extraction layer of the present application is >1.85.
在本申请的一些实施方式中，上述光提取层的红光折射率≥1.85，绿光折射率≥1.90，蓝光折射率≥2.00。In some embodiments of the present application, the refractive index of red light of the above-mentioned light extraction layer is greater than or equal to 1.85, the refractive index of green light is greater than or equal to 1.90, and the refractive index of blue light is greater than or equal to 2.00.
在本申请的一些实施方式中，所述光提取层的厚度为50-90nm，优选为60-80nm。In some embodiments of the present application, the thickness of the light extraction layer is 50-90 nm, preferably 60-80 nm.
本申请还提供一种显示装置，其中包含本申请的有机电致发光器件。所述显示装置包括但不限于显示器、电视、移动通信终端、平板电脑等。The present application also provides a display device comprising the organic electroluminescent device of the present application. The display device includes, but is not limited to, a display, a television, a mobile communication terminal, a tablet computer, and the like.
制备本申请的有机电致发光器件的方法没有特别限制，可以采用本领域公知的任何方法，例如，本申请可以采用如下制备方法制备：The method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art can be used. For example, the present application can be prepared by the following preparation method:
(1)清洗顶发光用OLED器件基板1上的阳极电极2，在清洗机中分别通过药洗、水洗、毛刷、高压水洗、风刀等步骤，然后再加热处理；(1) Cleaning the anode electrode 2 on the substrate 1 of the OLED device for top light emission, in the cleaning machine, the steps of washing with medicine, washing with water, brushing, high-pressure washing, air knife, etc. are respectively performed, and then heat treatment;
(2)在反射阳极电极2上真空蒸镀空穴注入层3，空穴注入层3中包含主体材料和p型掺杂剂；(2) vacuum-evaporating a hole injection layer 3 on the reflective anode electrode 2, and the hole injection layer 3 contains a host material and a p-type dopant;
(3)在空穴注入层3上真空蒸镀空穴传输材料作为空穴传输层4；(3) vacuum evaporation of a hole transport material on the hole injection layer 3 as the hole transport layer 4;
(4)在空穴传输层4上真空蒸镀发光层5，发光层5中包含主体材料和发光染料；(4) vacuum-evaporating a light-emitting layer 5 on the hole transport layer 4, and the light-emitting layer 5 contains a host material and a light-emitting dye;
(5)在发光层5上真空蒸镀电子传输材料作为电子传输层6，电子传输层6中包含主体材料和n型掺杂剂；(5) vacuum-evaporating an electron transport material on the light-emitting layer 5 as the electron transport layer 6, and the electron transport layer 6 contains a host material and an n-type dopant;
(6)在电子传输层6上真空蒸镀电子注入材料作为电子注入层7，电子注入材料选自LiQ、LiF、NaCl、CsF、Li
2O、Cs
2CO
3、BaO、Na、Li、Ca等材料中的至少一种；
(6) An electron injection material is vacuum-evaporated on the electron transport layer 6 as the electron injection layer 7, and the electron injection material is selected from LiQ, LiF, NaCl, CsF, Li 2 O, Cs 2 CO 3 , BaO, Na, Li, Ca at least one of the other materials;
(7)在电子注入层7上真空蒸镀阴极材料作为阴极电极8；(7) vacuum evaporation cathode material is used as cathode electrode 8 on electron injection layer 7;
(8)最后在阴极电极8上蒸镀光提取材料作为光提取层9。(8) Finally, a light extraction material is evaporated on the cathode electrode 8 as the light extraction layer 9 .
以上仅描述一种典型的有机电致发光器件的结构及其制备方法，应当理解，本申请并不限于这种结构。The above only describes the structure of a typical organic electroluminescent device and its preparation method, and it should be understood that the present application is not limited to this structure.
合成实施例1：化合物LEM-1的合成Synthesis Example 1: Synthesis of Compound LEM-1
在反应瓶中加入100mmol的2-溴-三亚苯、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml四氢呋喃(THF)和200ml水，并加入1mol％的四(三苯基膦)钯(Pd(PPh
3)
4)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-三亚苯的1mol％。
100 mmol of 2-bromo-triphenylene, 100 mmol of 4-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of tetrahydrofuran (THF) and 200 ml of water were added to the reaction flask, and 1 mol% of tetrakis(triphenylphosphine) was added. ) palladium (Pd(PPh 3 ) 4 ). The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-triphenylene.
在反应瓶中加入100mmol的M1、100mmol的4-(联苯基)-4-联苯胺、28.8g叔丁醇钠(300mmol)、800ml二甲苯，并加入1mol％的(二亚苄基丙酮)钯(Pd(dba))。在120℃下 反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-1。其中，Pd(dba)的加入量为M1的1mol％。100 mmol of M1, 100 mmol of 4-(biphenyl)-4-benzidine, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene were added to the reaction flask, and 1 mol% of (dibenzylideneacetone) was added. Palladium (Pd(dba)). The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, and the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder LEM-1. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
1H NMR(400MHz,Chloroform)δ9.55(s,1H),9.25(s,1H),8.51–8.28(m,3H),7.75-7.68(m,7H),7.64(s,2H),7.57–7.46(m,11H),7.39(d,J＝10.0Hz,7H).
1 H NMR (400MHz, Chloroform) δ9.55(s,1H), 9.25(s,1H), 8.51-8.28(m,3H), 7.75-7.68(m,7H), 7.64(s,2H), 7.57 –7.46(m,11H),7.39(d,J=10.0Hz,7H).
M/Z：实验值，623.1；理论值，623.2。M/Z: experimental value, 623.1; theoretical value, 623.2.
合成实施例2：化合物LEM-3的合成Synthesis Example 2: Synthesis of Compound LEM-3
在反应瓶中加入100mmol的2-溴-三亚苯、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-三亚苯的1mol％。
100 mmol of 2-bromo-triphenylene, 100 mmol of 4-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-triphenylene.
在反应瓶中加入100mmol的M1、100mmol的双[4-(2-萘基)苯基]胺、28.8g叔丁醇钠(300mmol)、800ml二甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-3。其中，Pd(dba)的加入量为M1的1mol％。Into the reaction flask were added 100 mmol of M1, 100 mmol of bis[4-(2-naphthyl)phenyl]amine, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene, and 1 mol% of Pd(dba). The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, and the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder LEM-3. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
1H NMR(400MHz,Chloroform)δ9.48(s,1H),8.92(s,1H),8.35(d,J＝10.0Hz,2H),8.30(s,2H),8.11(dd,J＝12.0,8.0Hz,7H),7.70(s,1H),7.63(d,J＝8.0Hz,6H),7.60–7.40(m,12H),7.38(d,J＝8.4Hz,6H).
1 H NMR (400MHz, Chloroform) δ 9.48 (s, 1H), 8.92 (s, 1H), 8.35 (d, J=10.0 Hz, 2H), 8.30 (s, 2H), 8.11 (dd, J=12.0 ,8.0Hz,7H),7.70(s,1H),7.63(d,J=8.0Hz,6H),7.60–7.40(m,12H),7.38(d,J=8.4Hz,6H).
M/Z：实验值，723.1；理论值，723.3。M/Z: experimental value, 723.1; theoretical value, 723.3.
合成实施例3：化合物LEM-10的合成Synthesis Example 3: Synthesis of Compound LEM-10
在反应瓶中加入100mmol的2-溴-三亚苯、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-三亚苯的1mol％。
100 mmol of 2-bromo-triphenylene, 100 mmol of 4-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-triphenylene.
在反应瓶中加入100mmol的M1、100mmol的苯胺、28.8g叔丁醇钠(300mmol)、800ml甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M2。其中，Pd(dba)的加入量为M1的1mol％。Into the reaction flask were added 100 mmol of M1, 100 mmol of aniline, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of toluene, and 1 mol% of Pd(dba). The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder M2. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
在反应瓶中加入100mmol的2-氯苯并噁唑、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M3。其中，Pd(PPh
3)
4的加入量为2-氯苯并噁唑的1mol％。
100 mmol of 2-chlorobenzoxazole, 100 mmol of 4-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the reaction was completed, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-chlorobenzoxazole.
在反应瓶中加入100mmol的M2、100mmol的M3、28.8g叔丁醇钠(300mmol)、800ml甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-10。其中，Pd(dba)的加入量为M2的1mol％。100 mmol of M2, 100 mmol of M3, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of toluene, and 1 mol% of Pd(dba) were added to the reaction flask. The reaction was carried out at 120°C for 12h. After the reaction was completed, the reaction was stopped, and the reactant was cooled to room temperature, added with water, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain LEM-10 as a white powder. Wherein, the addition amount of Pd(dba) is 1 mol% of M2.
1H NMR(400MHz,Chloroform)δ9.50(s,1H),9.24(s,1H),8.50–8.37(m,3H),7.76–7.68(m,6H),7.64(s,2H),7.54(d,J＝12.0Hz,5H),7.38(d,J＝8.4Hz,6H),7.24(s,2H),7.08 (s,2H),7.00(s,1H).
1 H NMR (400MHz, Chloroform) δ9.50(s,1H), 9.24(s,1H), 8.50-8.37(m,3H), 7.76-7.68(m,6H), 7.64(s,2H), 7.54 (d,J=12.0Hz,5H),7.38(d,J=8.4Hz,6H),7.24(s,2H),7.08(s,2H),7.00(s,1H).
M/Z：实验值，588.3；理论值，588.2。M/Z: experimental value, 588.3; theoretical value, 588.2.
合成实施例4：化合物LEM-15的合成Synthesis Example 4: Synthesis of Compound LEM-15
在反应瓶中加入100mmol的2-溴-三亚苯、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-三亚苯的1mol％。
100 mmol of 2-bromo-triphenylene, 100 mmol of 4-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-triphenylene.
在反应瓶中加入100mmol的M1、100mmol的4-联苯胺、28.8g叔丁醇钠(300mmol)、800ml甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M2。其中，Pd(dba)的加入量为M1的1mol％。Into the reaction flask were added 100 mmol of M1, 100 mmol of 4-benzidine, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of toluene, and 1 mol% of Pd(dba). The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder M2. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
在反应瓶中加入100mmol的2-溴(9,9-二甲基芴)、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M3。其中，Pd(PPh
3)
4的加入量为2-溴(9,9-二甲基芴)的1mol％。
100 mmol of 2-bromo(9,9-dimethylfluorene), 100 mmol of 4-chlorophenylboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd was added. (PPh 3 ) 4 . The reaction was carried out at 120°C for 12h. After the reaction was completed, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Wherein, the added amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo(9,9-dimethylfluorene).
在反应瓶中加入100mmol的M2、100mmol的M3、28.8g叔丁醇钠(300mmol)、800ml 甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-10。其中，Pd(dba)的加入量为M2的1mol％。Into the reaction flask were added 100 mmol of M2, 100 mmol of M3, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of toluene, and 1 mol% of Pd(dba). The reaction was carried out at 120°C for 12h. After the reaction was completed, the reaction was stopped, and the reactant was cooled to room temperature, added with water, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain LEM-10 as a white powder. Wherein, the addition amount of Pd(dba) is 1 mol% of M2.
1H NMR(400MHz,Chloroform)δ9.60(s,1H),9.26(s,1H),8.51–8.17(m,3H),8.09(s,1H),8.02(s,1H),7.90(s,1H),7.77(d,J＝12.0Hz,4H),7.85–7.67(m,5H),7.63(ddd,J＝14.4,10.0,8.0Hz,12H),7.41(s,1H),7.36(d,J＝13.6Hz,6H),7.24(s,1H),1.69(s,6H).
1 H NMR (400MHz, Chloroform) δ9.60(s,1H), 9.26(s,1H), 8.51-8.17(m,3H), 8.09(s,1H), 8.02(s,1H), 7.90(s ,1H),7.77(d,J＝12.0Hz,4H),7.85–7.67(m,5H),7.63(ddd,J＝14.4,10.0,8.0Hz,12H),7.41(s,1H),7.36( d, J=13.6Hz, 6H), 7.24(s, 1H), 1.69(s, 6H).
M/Z：实验值，739.4；理论值，739.3。M/Z: experimental value, 739.4; theoretical value, 739.3.
合成实施例5：化合物LEM-18的合成Synthesis Example 5: Synthesis of Compound LEM-18
在反应瓶中加入100mmol的三亚苯-2-频那醇酯、100mmol的2-溴-5-氯吡啶、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-5-氯吡啶的1mol％。
100 mmol of triphenylene-2-pinacol ester, 100 mmol of 2-bromo-5-chloropyridine, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd ( PPh 3 ) 4 . The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-5-chloropyridine.
在反应瓶中加入100mmol的M1、100mmol的双[4-(2-萘基)苯基]胺、28.8g叔丁醇钠(300mmol)、800ml二甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-18。其中，Pd(dba)的加入量为M1的1mol％。Into the reaction flask were added 100 mmol of M1, 100 mmol of bis[4-(2-naphthyl)phenyl]amine, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene, and 1 mol% of Pd(dba). The reaction was carried out at 120°C for 12h. After the reaction was completed, the reaction was stopped, and the reactant was cooled to room temperature, added with water, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder LEM-18. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
1H NMR(400MHz,Chloroform)δ9.60(s,1H),9.18(s,1H),8.54(s,1H),8.32(d,J＝12.0Hz,2H),8.08(d,J＝12.0Hz,3H),7.91(d,J＝10.0Hz,5H),7.70(s,1H),7.63(t,J＝8.0Hz,6H),7.60–7.39(m,10H),7.38(d,J＝8.0Hz,6H),6.82(s,1H).
1 H NMR (400MHz, Chloroform) δ 9.60(s, 1H), 9.18(s, 1H), 8.54(s, 1H), 8.32(d, J=12.0Hz, 2H), 8.08(d, J=12.0 Hz, 3H), 7.91(d, J＝10.0Hz, 5H), 7.70(s, 1H), 7.63(t, J＝8.0Hz, 6H), 7.60–7.39(m, 10H), 7.38(d, J =8.0Hz,6H),6.82(s,1H).
M/Z：实验值，724.4；理论值，724.3。M/Z: experimental value, 724.4; theoretical value, 724.3.
合成实施例6：化合物LEM-19的合成Synthesis Example 6: Synthesis of Compound LEM-19
在反应瓶中加入100mmol的三亚苯-2-频那醇酯、100mmol的2-溴-5-氯吡啶、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-5-氯吡啶的1mol％。
100 mmol of triphenylene-2-pinacol ester, 100 mmol of 2-bromo-5-chloropyridine, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd ( PPh 3 ) 4 . The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-5-chloropyridine.
在反应瓶中加入100mmol的M1、100mmol的4-(2-萘基)苯胺、28.8g叔丁醇钠(300mmol)、800ml甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M2。其中，Pd(dba)的加入量为M1的1mol％。Into the reaction flask were added 100 mmol of M1, 100 mmol of 4-(2-naphthyl)aniline, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of toluene, and 1 mol% of Pd(dba). The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder M2. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
在反应瓶中加入100mmol的2-萘硼酸、100mmol的2-溴-5-氯吡啶、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M3。其中，Pd(PPh
3)
4的加入量为2-溴-5-氯吡啶的1mol％。
100 mmol of 2-naphthaleneboronic acid, 100 mmol of 2-bromo-5-chloropyridine, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the reaction was completed, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was purified by recrystallization with toluene to obtain a white powder M3. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-5-chloropyridine.
在反应瓶中加入100mmol的M2、100mmol的M3、28.8g叔丁醇钠(300mmol)、800ml甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-19。其中，Pd(dba)的加入量为M2的1mol％。100 mmol of M2, 100 mmol of M3, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of toluene, and 1 mol% of Pd(dba) were added to the reaction flask. The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, and the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain LEM-19 as a white powder. Wherein, the addition amount of Pd(dba) is 1 mol% of M2.
1H NMR(400MHz,Chloroform)δ9.60(s,1H),9.17(s,1H),8.85(s,1H),8.55(t,J＝6.4Hz,1H),8.45(d,J＝12.0Hz,3H),8.32(d,J＝10.0Hz,4H),8.08(d,J＝12.0Hz,4H),7.94(t,J＝10.0Hz,4H),7.70(d,J＝8.8Hz,1H),7.60–7.40(m,12H),7.38(d,J＝8.0Hz,2H),6.82(s,1H).
1 H NMR (400MHz, Chloroform) δ 9.60(s, 1H), 9.17(s, 1H), 8.85(s, 1H), 8.55(t, J=6.4Hz, 1H), 8.45(d, J=12.0 Hz,3H),8.32(d,J＝10.0Hz,4H),8.08(d,J＝12.0Hz,4H),7.94(t,J＝10.0Hz,4H),7.70(d,J＝8.8Hz, 1H), 7.60–7.40(m, 12H), 7.38(d, J=8.0Hz, 2H), 6.82(s, 1H).
M/Z：实验值，725.1；理论值，725.3。M/Z: experimental value, 725.1; theoretical value, 725.3.
合成实施例7：化合物LEM-24的合成Synthesis Example 7: Synthesis of Compound LEM-24
在反应瓶中加入100mmol的2-溴-三亚苯、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-三亚苯的1mol％。
100 mmol of 2-bromo-triphenylene, 100 mmol of 4-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-triphenylene.
在反应瓶中加入200mmol的M1、100mmol的4-联苯胺、28.8g叔丁醇钠(300mmol)、800ml二甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-24。其中，Pd(dba)的加入量为M1的1mol％。200 mmol of M1, 100 mmol of 4-benzidine, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene were added to the reaction flask, and 1 mol% of Pd(dba) was added. The reaction was carried out at 120°C for 12h. After the reaction was completed, the reaction was stopped, and the reactant was cooled to room temperature, added with water, filtered, washed with water, and the obtained solid was purified by recrystallization with toluene to obtain a white powder LEM-24. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
1H NMR(400MHz,Chloroform)δ9.60(s,1H),8.50–8.26(m,3H),7.94(s,2H),7.88–7.66(m,12H),7.57–7.46(m,6H),7.38–7.16(m,12H),7.09(d,J＝10.0Hz,3H).
1 H NMR (400MHz, Chloroform)δ9.60(s,1H),8.50-8.26(m,3H),7.94(s,2H),7.88-7.66(m,12H),7.57-7.46(m,6H) ,7.38–7.16(m,12H),7.09(d,J＝10.0Hz,3H).
M/Z：实验值，773.2；理论值，773.3。M/Z: experimental value, 773.2; theoretical value, 773.3.
合成实施例8：化合物LEM-27的合成Synthesis Example 8: Synthesis of Compound LEM-27
在反应瓶中加入100mmol的2-溴-三亚苯、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-三亚苯的1mol％。
100 mmol of 2-bromo-triphenylene, 100 mmol of 4-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-triphenylene.
在反应瓶中加入100mmol的M1、100mmol的4-联苯胺、28.8g叔丁醇钠(300mmol)、800ml二甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M2。其中，Pd(dba)的加入量为M1的1mol％。100 mmol of M1, 100 mmol of 4-benzidine, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene were added to the reaction flask, and 1 mol% of Pd(dba) was added. The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder M2. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
在反应瓶中加入100mmol的M2、100mmol的五氟溴苯、28.8g叔丁醇钠(300mmol)、800ml二甲苯，并加入1mol％的Pd(dba)。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-27。其中，Pd(dba)的加入量为M2的1mol％。100 mmol of M2, 100 mmol of pentafluorobromobenzene, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene were added to the reaction flask, and 1 mol% of Pd(dba) was added. The reaction was carried out at 120°C for 12h. After the reaction is completed, the reaction is stopped, the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder LEM-27. Wherein, the addition amount of Pd(dba) is 1 mol% of M2.
1H NMR(400MHz,Chloroform)δ9.60(s,1H),9.23(s,1H),8.50–8.17(m,6H),7.75-7.64(m,4H),7.57–7.46(m,6H),7.39(d,J＝10.0Hz,6H).
1 H NMR (400MHz, Chloroform) δ9.60(s,1H), 9.23(s,1H), 8.50-8.17(m,6H), 7.75-7.64(m,4H), 7.57-7.46(m,6H) ,7.39(d,J＝10.0Hz,6H).
M/Z：实验值，637.1；理论值，637.2。M/Z: experimental value, 637.1; theoretical value, 637.2.
合成实施例9：化合物LEM-28的合成Synthesis Example 9: Synthesis of Compound LEM-28
在反应瓶中加入100mmol的2-溴-三亚苯、100mmol的4-氯苯硼酸、41.4g碳酸钾(300mmol)、800ml的THF和200ml水，并加入1mol％的Pd(PPh
3)
4。在120℃下反应12h。反应完毕后停止反应，并将反应物冷却至室温，加水，有机相浓缩得到白色固体，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M1。其中，Pd(PPh
3)
4的加入量为2-溴-三亚苯的1mol％。
100 mmol of 2-bromo-triphenylene, 100 mmol of 4-chlorobenzeneboronic acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water were added to the reaction flask, and 1 mol% of Pd(PPh 3 ) 4 was added. The reaction was carried out at 120°C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Wherein, the addition amount of Pd(PPh 3 ) 4 is 1 mol% of 2-bromo-triphenylene.
在反应瓶中加入100mmol的M1、100mmol的4-氨基对联三苯、28.8g叔丁醇钠(300mmol)、1000ml二甲苯，并加入1mol％的Pd(dba)。在120℃下反应18h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末M2。其中，Pd(dba)的加入量为M1的1mol％。Into the reaction flask were added 100 mmol of M1, 100 mmol of 4-amino-terphenyl, 28.8 g of sodium tert-butoxide (300 mmol), 1000 ml of xylene, and 1 mol% of Pd(dba). The reaction was carried out at 120°C for 18h. After the reaction is completed, the reaction is stopped, the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain a white powder M2. Wherein, the addition amount of Pd(dba) is 1 mol% of M1.
在反应瓶中加入100mmol的M2、100mmol的五氘代溴苯、28.8g叔丁醇钠(300mmol)、800ml二甲苯，并加入1mol％的Pd(dba)。在120℃下反应18h。反应完毕后停止反应，并将反应物冷却至室温，加水，过滤，水洗，所得到的固体用甲苯进行重结晶纯化，得到白色粉末LEM-28。其中，Pd(dba)的加入量为M2的1mol％。100 mmol of M2, 100 mmol of pentadeuteriobromobenzene, 28.8 g of sodium tert-butoxide (300 mmol), 800 ml of xylene were added to the reaction flask, and 1 mol% of Pd(dba) was added. The reaction was carried out at 120°C for 18h. After the reaction is completed, the reaction is stopped, the reactant is cooled to room temperature, water is added, filtered, and washed with water. The obtained solid is purified by recrystallization with toluene to obtain LEM-28 as a white powder. Wherein, the addition amount of Pd(dba) is 1 mol% of M2.
1H NMR(400MHz,Chloroform)δ9.60(s,1H),9.23(s,1H),8.50-8.27(m,3H),7.75-7.56(m,6H),7.52–7.44(m,3H),7.37-7.28(d,8H).
1 H NMR (400MHz, Chloroform) δ9.60(s,1H), 9.23(s,1H), 8.50-8.27(m,3H), 7.75-7.56(m,6H), 7.52-7.44(m,3H) ,7.37-7.28(d,8H).
M/Z：实验值，631.1；理论值，631.3。M/Z: experimental value, 631.1; theoretical value, 631.3.
实施例1Example 1
在玻璃基板上设置反射阳极电极，该阳极电极为ITO电极，该电极厚度为130nm；A reflective anode electrode is arranged on the glass substrate, the anode electrode is an ITO electrode, and the thickness of the electrode is 130 nm;
然后，在阳极电极上真空蒸镀10nm厚度的空穴注入层，空穴注入层的材料为HT-11和质量比为3％的p型掺杂剂p-1，其中，蒸镀速率为0.1nm/s，选用的空穴注入层的材料和p型掺杂剂分别为以下材料：Then, a hole injection layer with a thickness of 10 nm was vacuum evaporated on the anode electrode. The material of the hole injection layer was HT-11 and a p-type dopant p-1 with a mass ratio of 3%, wherein the evaporation rate was 0.1 nm/s, the selected hole injection layer materials and p-type dopants are the following materials:
然后，在空穴注入层上真空蒸镀112nm的空穴传输层，空穴传输层的材料为上述HT-32，其中，蒸镀速率为0.1nm/s；Then, a hole transport layer with a thickness of 112 nm was vacuum evaporated on the hole injection layer, and the material of the hole transport layer was the above-mentioned HT-32, wherein the evaporation rate was 0.1 nm/s;
然后，在空穴传输层之上真空蒸镀发光层，发光层包括主体材料BH-1和发光染料BD-1，利用多源共蒸的方法进行蒸镀，其中，调节主体材料BH-1的蒸镀速率为0.1nm/s，染料BD-1蒸镀速率为主体材料蒸镀速率的3％，蒸镀总膜厚为20nm，主体材料和发光染料分别为以下材料：Then, a light-emitting layer is vacuum-evaporated on the hole transport layer, and the light-emitting layer includes a host material BH-1 and a light-emitting dye BD-1, and is vapor-deposited by a multi-source co-evaporation method, wherein the host material BH-1 is adjusted The evaporation rate is 0.1nm/s, the evaporation rate of dye BD-1 is 3% of the evaporation rate of the host material, the total film thickness of evaporation is 20nm, the host material and the luminescent dye are the following materials:
然后，在发光层上真空蒸镀厚度为35nm的电子传输层，电子传输层包含电子传输材料ET-58和n型掺杂剂n-1，其中n型掺杂剂的含量为50mol％，所用的电子传输材料和n型掺杂剂分别为以下材料：Then, an electron transport layer with a thickness of 35 nm was vacuum-evaporated on the light-emitting layer. The electron transport layer contained an electron transport material ET-58 and an n-type dopant n-1, wherein the content of the n-type dopant was 50 mol%. The electron transport materials and n-type dopants are the following materials:
然后，在电子传输层上真空蒸镀厚度为40nm的电子注入层，电子注入层的材料为Liq(8-羟基喹啉-锂)，其中，蒸镀速度为0.1nm/s；Then, an electron injection layer with a thickness of 40 nm is vacuum-evaporated on the electron transport layer, and the material of the electron injection layer is Liq (8-hydroxyquinoline-lithium), and the evaporation rate is 0.1 nm/s;
然后，在电子注入层上真空蒸镀厚度为18nm的阴极电极，阴极电极由Mg:Ag摩尔比为1:9的阴极材料构成，蒸镀速率为1nm/s；Then, a cathode electrode with a thickness of 18 nm is vacuum-evaporated on the electron injection layer, and the cathode electrode is composed of a cathode material with a Mg:Ag molar ratio of 1:9, and the evaporation rate is 1 nm/s;
最后，在阴极电极上真空蒸镀厚度为50nm的光提取层，光提取层的材料为LEM-1。Finally, a light extraction layer with a thickness of 50 nm was vacuum evaporated on the cathode electrode, and the material of the light extraction layer was LEM-1.
本实施例的有机电致发光器件发出蓝光。The organic electroluminescent device of this embodiment emits blue light.
实施例2-5Example 2-5
除了如表1所示改变光提取层的厚度以外，其余与实施例1相同。Except that the thickness of the light extraction layer was changed as shown in Table 1, the rest was the same as that of Example 1.
实施例6Example 6
除了将发光主体材料和发光染料分别替换为GPH-82、GD01以外，其余与实施例1相同。Except for replacing the luminescent host material and luminescent dye with GPH-82 and GD01, respectively, the rest is the same as that of Example 1.
本实施例的有机电致发光器件发出绿光。The organic electroluminescent device of this embodiment emits green light.
实施例7-10Examples 7-10
除了如表1所示改变光提取层厚度以外，其余与实施例6相同。Except that the thickness of the light extraction layer was changed as shown in Table 1, the rest was the same as that of Example 6.
实施例11Example 11
除了将发光主体材料和发光染料分别替换为RH-10、RPD-1以外，其余与实施例1相同。The rest is the same as Example 1, except that the light-emitting host material and the light-emitting dye are replaced by RH-10 and RPD-1, respectively.
本实施例的有机电致发光器件发出红光。The organic electroluminescent device of this embodiment emits red light.
实施例12-15Examples 12-15
除了如表1所示改变光提取层的厚度以外，其余与实施例11相同。Except that the thickness of the light extraction layer was changed as shown in Table 1, the rest was the same as that of Example 11.
实施例16-39Examples 16-39
除了用LEM-3、LEM-10、LEM-15、LEM-18、LEM-19、LEM-24、LEM-27、LEM-28分别代替LEM-1以外，其余与提取层厚度为70nm的相应的上述实施例相同，具体见表1。Except for replacing LEM-1 with LEM-3, LEM-10, LEM-15, LEM-18, LEM-19, LEM-24, LEM-27, and LEM-28, respectively, the rest are corresponding to the extraction layer thickness of 70 nm. The above-mentioned embodiments are the same, see Table 1 for details.
实施例40-42Examples 40-42
除了如表1所示将空穴传输材料分别替换为B6、B9、B23以外，其余与实施例3相同。Except for replacing the hole transport material with B6, B9, and B23 as shown in Table 1, the rest is the same as that of Example 3.
实施例43-45Examples 43-45
除了如表1所示将电子传输材料分别替换为C12、C27、C28以外，其余与实施例3相同。Except having replaced the electron transport material with C12, C27, and C28, respectively, as shown in Table 1, the rest was the same as that of Example 3.
实施例46Example 46
除了如表1所示将空穴传输材料替换为B6、电子传输材料替换为C27以外，其余与实施例31相同。The same as in Example 31, except that the hole transport material was replaced by B6 and the electron transport material was replaced by C27 as shown in Table 1.
实施例1-46的数据和测试结果具体见表1和表2。The data and test results of Examples 1-46 are specifically shown in Table 1 and Table 2.
对比例1Comparative Example 1
除了用化合物1-1代替LEM-1以外，其余与实施例1相同。The procedure was the same as in Example 1, except that Compound 1-1 was used instead of LEM-1.
对比例2-5Comparative Examples 2-5
除了如表1所示改变光提取层厚度以外，其余与对比例1相同。Except for changing the thickness of the light extraction layer as shown in Table 1, the rest is the same as that of Comparative Example 1.
对比例6Comparative Example 6
除了用化合物1-1代替LEM-1以外，其余与实施例6相同。The procedure was the same as in Example 6, except that Compound 1-1 was used instead of LEM-1.
对比例7-10Comparative Examples 7-10
除了如表1所示改变光提取层厚度以外，其余与对比例6相同。Except that the thickness of the light extraction layer was changed as shown in Table 1, the rest was the same as that of Comparative Example 6.
对比例11Comparative Example 11
除了用化合物1-1代替LEM-1以外，其余与实施例11相同。The procedure was the same as in Example 11, except that Compound 1-1 was used instead of LEM-1.
对比例12-15Comparative Example 12-15
除了如表1所示改变光提取层厚度以外，其余与对比例11相同。Except that the thickness of the light extraction layer was changed as shown in Table 1, the rest was the same as that of Comparative Example 11.
对比例16-18Comparative Examples 16-18
除了用化合物1-2代替化合物1-1以外，其余与提取层厚度为70nm的相应的上述对比例相同。Except that compound 1-2 was used instead of compound 1-1, the rest was the same as the corresponding above-mentioned comparative example with an extraction layer thickness of 70 nm.
对比例1-18的数据和测试结果具体见表1和表2。The data and test results of Comparative Examples 1-18 are shown in Table 1 and Table 2.
折射率的测定Determination of Refractive Index
测量仪器为_Radiation technology公司的Version-1.0.1.4光谱型椭偏仪；玻璃基板大小为200mm×200mm，材料薄膜厚度为80nm。测定在不同波长下化合物的折射率。The measuring instrument is Version-1.0.1.4 spectroscopic ellipsometer of _Radiation technology company; the size of the glass substrate is 200mm×200mm, and the thickness of the material film is 80nm. The refractive index of the compound was measured at different wavelengths.
有机电致发光器件的性能检测Performance Testing of Organic Electroluminescent Devices
具体采用BJV测试系统来测试有机电致发光器件的电流效率和CIE色坐标。Specifically, the BJV test system was used to test the current efficiency and CIE color coordinates of the organic electroluminescent device.
对于蓝光器件，使用蓝光指数(BI)考察其发光效率，而CIEy值主要评价蓝光颜色 的饱和度，蓝光指数为蓝光器件的电流效率除以CIEy值得到，CIEy值变大表明蓝光颜色发生红移，CIEy值变小表明蓝光颜色发生蓝移；使用电流效率来评价绿光和红光器件发光效率；对绿光和红光器件颜色变化，主要用CIEx值来评价，CIEx变大表明发光红移，CIEx变小，表明发光蓝移。For blue light devices, the blue light index (BI) is used to investigate the luminous efficiency, and the CIEy value mainly evaluates the saturation of the blue light color. The blue light index is obtained by dividing the current efficiency of the blue light device by the CIEy value. The larger the CIEy value, the red shift of the blue color. , the decrease of CIEy value indicates the blue shift of blue color; the current efficiency is used to evaluate the luminous efficiency of green and red devices; the color change of green and red devices is mainly evaluated by the CIEx value, and the increase of CIEx indicates the red shift of luminescence , CIEx becomes smaller, indicating a blue-shift of luminescence.
表1实施例和对比例中元器件性能对比Table 1 Performance comparison of components in the embodiment and the comparative example
注：表1中的“-”表示无对应参数。Note: "-" in Table 1 means there is no corresponding parameter.
化合物1-1的蓝光器件，当光提取层厚度从50nm增大到90nm后，蓝光指数从92变成76，下降了16，CIEy从0.050变成0.070，增大了0.020，表明蓝光发生了红移，意味着蓝光颜色变浅；化合物LEM-1的蓝光器件，当光提取层厚度从50nm增大到90nm后，蓝光指数从96变成83，下降了7，CIEy从0.051变成0.063，增大了0.012；并且，当光提取层厚度相同时，化合物1-1的蓝光指数均小于化合物LEM-1，化合物1-1的CIEy均大于化合物LEM-1，表明LEM-1的蓝光器件的蓝光颜色饱和度更高。For the blue light device of compound 1-1, when the thickness of the light extraction layer increased from 50 nm to 90 nm, the blue light index changed from 92 to 76, which decreased by 16, and the CIEy changed from 0.050 to 0.070, which increased by 0.020, indicating that the blue light changed to red. When the thickness of the light extraction layer increases from 50nm to 90nm, the blue light index changes from 96 to 83, a decrease of 7, and the CIEy changes from 0.051 to 0.063, an increase of 7. When the thickness of the light extraction layer is the same, the blue light index of compound 1-1 is smaller than that of compound LEM-1, and the CIEy of compound 1-1 is larger than that of compound LEM-1, indicating that the blue light of the blue light device of LEM-1 Color saturation is higher.
化合物1-1的绿光器件，光提取层厚度从50nm增大到90nm，电流效率从97cd/A变成101cd/A，增大了4cd/A，CIEx从0.235变成0.250，增大了0.015；而化合物LEM-1的绿光器件，电流效率从99cd/A变成106cd/A，增大了7cd/A，CIEx从0.234变成0.243，增大了0.009。For the green light device of compound 1-1, the thickness of the light extraction layer is increased from 50nm to 90nm, the current efficiency is changed from 97cd/A to 101cd/A, an increase of 4cd/A, and the CIEx is changed from 0.235 to 0.250, an increase of 0.015 For the green light device of compound LEM-1, the current efficiency changed from 99cd/A to 106cd/A, an increase of 7cd/A, and the CIEx changed from 0.234 to 0.243, an increase of 0.009.
化合物1-1的红光器件，光提取层厚度从50nm增大到90nm，电流效率从46cd/A变成53cd/A，增大了7cd/A，CIEx从0.665变成0.675，增大了0.010；而化合物LEM-1的红光器件，电流效率从48cd/A变成61cd/A，增大了13cd/A，CIEx从0.665变成0.676，增大了0.011。For the red light device of compound 1-1, the thickness of the light extraction layer increased from 50nm to 90nm, the current efficiency increased from 46cd/A to 53cd/A, an increase of 7cd/A, and the CIEx increased from 0.665 to 0.675, an increase of 0.010 For the red light device of compound LEM-1, the current efficiency changed from 48cd/A to 61cd/A, an increase of 13cd/A, and the CIEx changed from 0.665 to 0.676, an increase of 0.011.
从以上化合物1-1和LEM-1不同厚度、相同发光颜色器件的对比中可以看出，相比于化合物1-1作为光提取材料，化合物LEM-1作为光提取材料，能够使器件的发光颜色饱和度更高、电流效率更大。It can be seen from the comparison of the devices with different thicknesses and the same emission color between compound 1-1 and LEM-1 above, compared with compound 1-1 as a light extraction material, compound LEM-1 as a light extraction material can make the device emit light. Higher color saturation and greater current efficiency.
实施例40-46分别使用了本申请提供的化合物作为空穴注入材料和电子传输材料，使用这些材料的蓝光器件，与相同光提取层厚度的对比例比较，可以看出，蓝光指数明显增大，CIEy减小。Examples 40-46 used the compounds provided in this application as hole injection materials and electron transport materials, respectively. The blue light devices using these materials were compared with the comparative examples with the same thickness of the light extraction layer. It can be seen that the blue light index increased significantly. , CIEy decreases.
表2相对折射率(n)对比Table 2 Relative refractive index (n) comparison
从表2可以看出，相较于化合物1-1、1-2，本申请提供的化合物用于有机电致发光器件的光提取层，蓝光、绿光和红光的折射率得到明显提高，因此能够更加有效地促进光取出，可以提供高的出光率，使有机电致发光器件的发光效率得到大幅度提升。As can be seen from Table 2, compared with compounds 1-1 and 1-2, the compounds provided by the present application are used in the light extraction layer of organic electroluminescent devices, and the refractive indices of blue light, green light and red light are significantly improved, Therefore, light extraction can be more effectively promoted, a high light extraction rate can be provided, and the luminous efficiency of the organic electroluminescent device can be greatly improved.
以上所述仅为本申请的较佳实施例，并非用于限定本申请的保护范围。凡在本申请的精神和原则之内所作的任何修改、等同替换、改进等，均包含在本申请的保护范围内。The above descriptions are only preferred embodiments of the present application, and are not intended to limit the protection scope of the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of this application are included in the protection scope of this application.
Claims (11)
- 一种有机电致发光器件，包括：An organic electroluminescent device, comprising:基板、阳极电极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、阴极电极和光提取层；Substrate, anode electrode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer, cathode electrode and light extraction layer;所述光提取层包括通式(I)的化合物：The light extraction layer includes a compound of general formula (I):
其中，Ar 1和Ar 2各自独立地选自H原子、氘原子、卤素、C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Ra取代，所述杂芳基上的杂原子各自独立地选自O、S和N，所述Ra各自独立地选自氘、卤素、C 1-C 6的烷基、苯基、联苯基、三联苯基或萘基； Wherein, Ar 1 and Ar 2 are each independently selected from H atom, deuterium atom, halogen, C 6 -C 30 aryl group or C 3 -C 30 heteroaryl group, the hydrogen on the aryl group and the heteroaryl group Each atom can be independently substituted with Ra, the heteroatoms on the heteroaryl group are each independently selected from O, S and N, and the Ra is each independently selected from deuterium, halogen, C 1 -C 6 alkyl, phenyl, biphenyl, terphenyl or naphthyl;L 1、L 2和L 3各自独立地选自亚苯基或亚吡啶基。 L 1 , L 2 and L 3 are each independently selected from phenylene or pyridylene. - 根据权利要求1所述的有机电致发光器件，其中，所述L 1、L 2和L 3各自独立地选自以下基团： The organic electroluminescent device of claim 1 , wherein the L 1 , L 2 and L 3 are each independently selected from the following groups:
图中*表示连接位点。* in the figure indicates the ligation site. - 根据权利要求1所述的有机电致发光器件，其中，所述Ar 1和Ar 2各自独立地选自以下基团： The organic electroluminescent device of claim 1, wherein the Ar 1 and Ar 2 are each independently selected from the following groups:
其中，in,R 1和R 2各自独立地选自C 1-C 6的烷基、C 6-C 12的芳基或C 3-C 12的杂芳基。 R 1 and R 2 are each independently selected from C 1 -C 6 alkyl, C 6 -C 12 aryl, or C 3 -C 12 heteroaryl. - 根据权利要求1所述的有机电致发光器件，其中，所述化合物可以选自以下化合物：The organic electroluminescent device according to claim 1, wherein the compound can be selected from the following compounds:
- 根据权利要求1所述的有机电致发光器件，其中，所述光提取层的折射率＞1.85。The organic electroluminescent device of claim 1, wherein the light extraction layer has a refractive index >1.85.
- 根据权利要求1所述的有机电致发光器件，其中，所述光提取层的红光折射率≥1.85，绿光折射率≥1.90，蓝光折射率≥2.00。The organic electroluminescent device according to claim 1, wherein the light extraction layer has a refractive index of red light≥1.85, a refractive index of green light≥1.90, and a refractive index of blue light≥2.00.
- 根据权利要求1所述的有机电致发光器件，其中，所述光提取层的厚度为50-90nm。The organic electroluminescent device of claim 1, wherein the light extraction layer has a thickness of 50-90 nm.
- 根据权利要求1所述的有机电致发光器件，其中，所述光提取层的厚度为60-80nm。The organic electroluminescent device of claim 1, wherein the light extraction layer has a thickness of 60-80 nm.
- 根据权利要求1所述的有机电致发光器件，其中，所述空穴传输层包括通式(II)的化合物：The organic electroluminescent device of claim 1, wherein the hole transport layer comprises a compound of general formula (II):
其中，in,Ar 3和Ar 4各自独立地选自C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代； Ar 3 and Ar 4 are each independently selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group may each independently be substituted by Rb;R 3-R 6各自独立地选自氢、氘、C 1-C 10的烷基、C 3-C 6的环烷基、C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代，所述R 3-R 6中相邻的两个基团能够连接成环； R 3 -R 6 are each independently selected from hydrogen, deuterium, C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl base, the hydrogen atoms on the aryl group and the heteroaryl group can be independently substituted by Rb, and the two adjacent groups in the R 3 -R 6 can be connected to form a ring;R 7和R 8各自独立地选自C 1-C 10的烷基、C 3-C 6的环烷基、C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代，所述R 7和R 8能够连接成环； R 7 and R 8 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 aryl, or C 3 -C 30 heteroaryl, said The hydrogen atoms on the aryl group and the heteroaryl group can each independently be replaced by Rb, and the R7 and R8 can be connected to form a ring;X选自O、S、CR 9R 10、NR 11，R 9和R 10各自独立地选自C 1-C 10的烷基、C 3-C 6的环烷基、C 6-C 30的芳基或C 3-C 30的杂芳基，所述R 11选自C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rb取代，所述R 9和R 10能够连接成环； X is selected from O, S, CR 9 R 10 , NR 11 , R 9 and R 10 are each independently selected from C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, C 6 -C 30 alkyl Aryl or C 3 -C 30 heteroaryl, the R 11 is selected from C 6 -C 30 aryl or C 3 -C 30 heteroaryl, the aryl and the hydrogen atom on the heteroaryl Each independently can be substituted by Rb, and said R 9 and R 10 can be linked to form a ring;L选自化学键、C 6-C 30的亚芳基或C 3-C 30的亚杂芳基，所述亚芳基和亚杂芳基上的氢原子各自独立地可以被Rb取代； L is selected from a chemical bond, a C 6 -C 30 arylene group or a C 3 -C 30 heteroarylene group, and each of the hydrogen atoms on the arylene group and the heteroarylene group independently may be substituted by Rb;所述杂芳基或亚杂芳基上的杂原子各自独立地选自O、S、N；The heteroatoms on the heteroaryl or heteroarylene are each independently selected from O, S, N;所述Rb各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基或萘基。 The Rbs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl. - 根据权利要求1所述的有机电致发光器件，其中，所述电子传输层包含通式(III)的化合物：The organic electroluminescent device of claim 1, wherein the electron transport layer comprises a compound of general formula (III):
其中，in,R 12-R 17各自独立地选自氢、氘、C 1-C 6的烷基、C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代，所述R 12-R 14中相邻的两个基团能够连接成环，所述R 16和R 17能够连接成环； R 12 -R 17 are each independently selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl, said aryl and heteroaryl The hydrogen atoms on each independently can be substituted by Rc, the adjacent two groups in the R 12 -R 14 can be connected to form a ring, and the R 16 and R 17 can be connected to form a ring;A选自C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代； A is selected from a C 6 -C 30 aryl group or a C 3 -C 30 heteroaryl group, and the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc;Y选自O、S、CR 18R 19，R 18和R 19各自独立地选自C 1-C 6的烷基、C 5-C 20的环烷基、C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代，所述R 18和R 19能够连接成环； Y is selected from O, S, CR 18 R 19 , R 18 and R 19 are each independently selected from C 1 -C 6 alkyl, C 5 -C 20 cycloalkyl, C 6 -C 30 aryl or The heteroaryl group of C 3 -C 30 , the hydrogen atoms on the aryl group and the heteroaryl group can each independently be substituted by Rc, and the R 18 and R 19 can be connected to form a ring;X 1-X 4各自独立地选自CR 20或N，R 20选自氢、氘、C 1-C 6的烷基、C 6-C 30的芳基或C 3-C 30的杂芳基，所述芳基和杂芳基上的氢原子各自独立地可以被Rc取代，且相邻的R 20能够连接成环； X 1 -X 4 are each independently selected from CR 20 or N, and R 20 is selected from hydrogen, deuterium, C 1 -C 6 alkyl, C 6 -C 30 aryl or C 3 -C 30 heteroaryl , the hydrogen atoms on the aryl group and the heteroaryl group can be substituted by Rc independently, and the adjacent R 20 can be connected to form a ring;L 1和L 2各自独立地选自化学键、C 6-C 30的亚芳基或C 3-C 30的亚杂芳基，所述亚芳基和亚杂芳基上的氢原子各自独立地可以被Rc取代； L 1 and L 2 are each independently selected from a chemical bond, a C 6 -C 30 arylene group, or a C 3 -C 30 heteroarylene group, and the hydrogen atoms on the arylene group and the heteroarylene group are each independently Can be replaced by Rc;所述杂芳基或所述亚杂芳基上的杂原子各自独立地选自O、S、N；The heteroatoms on the heteroaryl group or the heteroarylene group are each independently selected from O, S, N;所述Rc各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基或萘基。 The Rcs are each independently selected from deuterium, halogen, nitro, cyano, C1 - C4 alkyl, phenyl, biphenyl, terphenyl, or naphthyl. - 一种显示装置，其包含权利要求1-10任一项所述的有机电致发光器件。A display device comprising the organic electroluminescence device of any one of claims 1-10.
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| CN112687797B (en) | 2023-03-24 |
| CN112687797A (en) | 2021-04-20 |
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