CN114106054A - Organic electrophosphorescent luminescent material and device using same - Google Patents
Organic electrophosphorescent luminescent material and device using same Download PDFInfo
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- CN114106054A CN114106054A CN202111420040.8A CN202111420040A CN114106054A CN 114106054 A CN114106054 A CN 114106054A CN 202111420040 A CN202111420040 A CN 202111420040A CN 114106054 A CN114106054 A CN 114106054A
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- -1 phenylpyridyl group Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 33
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- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 3
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- 229910052769 Ytterbium Inorganic materials 0.000 description 1
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- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical group O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention relates to the technical field of organic electroluminescent display, and particularly discloses an organic electrophosphorescent luminescent material and an organic electroluminescent device adopting the organic electrophosphorescent luminescent material. The light-emitting material of the present invention has the following structure. The electroluminescent device prepared by the organic electrophosphorescent material has excellent performances of high purity, high brightness and high efficiency.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent display, and particularly discloses an organic electrophosphorescent luminescent material and an organic electroluminescent device adopting the electrophosphorescent luminescent material.
Background
The research of organic electroluminescent devices started in the 60 th 19 th century, and Pope first realized electroluminescence on anthracene single crystal, but at the time, the driving voltage was as high as 100V, and the quantum efficiency was very low. In 1987, Tang and VanSlyke used a double-layer thin film structure in which 8-hydroxyquinoline aluminum complex (Alq3) was used as a light-emitting layer and an electron-transporting layer, and TAPC was used as a hole-transporting layer, and an ITO electrode and an Mg: Ag electrode were used as an anode and a cathode, respectively, to produce high luminance (>1000cd/m2) The driving voltage of the green organic electroluminescent thin-film device with high efficiency (1.5lm/W) is reduced to below 10V. In 1990, polymer thin film electroluminescent devices made from poly (p-phenylene vinylene) (PPV) by Burroughes et al gave blue-green light output with quantum efficiency of 0.05% and driving voltage of less than 14V. In 1991, Braun et al produced green and orange light outputs with quantum efficiencies of 1% using derivatives of PPV, with drive voltages of about 3V. These research advances have immediately attracted considerable attention from scientists of various countries, and research on organic electroluminescence has been widely conducted worldwide and has gradually started to move to the market.
The organic electroluminescent display device has a structure including an anode formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode sequentially formed on the anode. The hole transport layer, the light emitting layer, and the electron transport layer are organic thin films composed of organic compounds. The light emitting materials in the organic thin film are classified into two groups according to the light emitting mechanism, one group is a fluorescent material using singlet excitons, and the other group is a phosphorescent material using triplet excitons. The phosphorescent material has higher luminous efficiency than the fluorescent material because the phosphorescent material can utilize 75% of triplet excitons and 25% of singlet excitons, whereas the fluorescent material utilizes only 25% of singlet excitons. The phosphorescent material is generally an organometallic compound containing a heavy metal, and forms a light emitting layer composed of a host material and a dopant material that emits light by transferring energy from the host material.
Organic electroluminescent devices using organic compounds having phosphorescent emission, Ir (ppy)3Is a commonly used Ir complex, but such compounds have serious problems of low phosphorescence efficiency, poor stability and lifetime, thus hindering the possibility of commercialization thereof.
Disclosure of Invention
The invention aims to develop a novel organic electrophosphorescent luminescent material, and develop an organic electroluminescent device adopting the luminescent material, so as to improve the luminescent purity, the luminescent brightness and the luminescent efficiency of the electroluminescent device.
Firstly, the invention provides an organic electrophosphorescent luminescent material, which has a structure shown as a general formula (I):
in formula (I): r2、R3、R4Each represents a substituent group ranging from single substitution to the maximum allowable number of substitutions;
R2、R3、R4each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms;
R3、R4can be connected in a ring, or R3、R4Each independently and the linked ring structure may form a fused ring structure by bridging, and when the fused ring structure is formed, the fused ring structure may be any one of a substituted or unsubstituted five-membered aromatic ring, a substituted or unsubstituted six-membered aromatic ring, a substituted or unsubstituted five-membered heteroaromatic ring, a substituted or unsubstituted six-membered heteroaromatic ring, or a six-membered heteroaromatic ringAt least one heteroatom in the heteroaromatic ring, wherein the heteroatom is selected from oxygen atom, nitrogen atom or sulfur atom;
R1one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms;
r is as defined above1、R2、R3、R4Wherein when each of the substituted or unsubstituted groups has a substituent group, the substituent group is selected from one or a combination of two of deuterium, halogen, cyano, chain alkyl of C1-C10, cycloalkyl of C3-C10, heterocycloalkyl of C3-C10, aryl of C6-C30 and heteroaryl of C3-C30, and R is as defined above3、R4When the ring structures connected with each other have a substituent group, the substituent group is one or a combination of two of deuterium, halogen, cyano, chain alkyl of C1-C10, cycloalkyl of C3-C10, heterocycloalkyl of C3-C10, aryl of C6-C30 and heteroaryl of C3-C30;
Z1～Z7independently selected from a nitrogen atom or a carbon atom; preferably, Z is1～Z6One or two of which are nitrogen atoms and the others are carbon atoms, and Z7Is a carbon atom;
still more preferably, Z is1～Z4One or two of which are nitrogen atoms and the others are carbon atoms, and Z5～Z7Are all carbon atoms; or preferably, said Z1、Z3、Z4One or two of which are nitrogen atoms and the others are carbon atoms, and Z5～Z7Are all carbon atoms; or preferably, said Z1Is a nitrogen atom, Z2～Z7Are all carbon atoms.
L is a monovalent, bidentate anion wherein the linking atoms X, Y are each independently selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms;
n is 1, 2 or 3.
As a preferred embodiment of the present invention, L is a monovalent bidentate anionic ligand, preferably L is one of substituted or unsubstituted phenylpyridyl group and substituted or unsubstituted acetylacetonate group, and when L has a substituent group, the substituent group is selected from one or a combination of two of deuterium, halogen, cyano group, nitro group, hydroxyl group, amino group, aldehyde group, ester group, chain alkyl group of C1 to C30, alkoxy group of C1 to C30, cycloalkyl group of C3 to C20, heterocycloalkyl group of C3 to C20, aryl group of C6 to C60, and heteroaryl group of C3 to C60.
Further preferably, L is a group represented by the formula L-1 or the formula L-2:
in L-1, R5～R12Each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted deuterated alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted deuterated aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 0 to 20 carbon atoms, substituted or unsubstituted alkyl substituted with carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atoms, and substituted or unsubstituted aryl substituted with carbon atoms, One of substituted or unsubstituted arylalkylsilyl groups having 6 to 20 carbon atoms, R5～R12Adjacent two of them may form a parallel ring structure by bridging;
wherein, in the formula L-2, R13～R19Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cyclic carbon having 3 to 20 carbon atomsOne of cycloalkyl of atoms, substituted or unsubstituted heteroalkyl of 1 to 20 carbon atoms, substituted or unsubstituted aralkyl of 6 to 30 carbon atoms, substituted or unsubstituted alkoxy of 1 to 20 carbon atoms, substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl of 0 to 20 carbon atoms, substituted or unsubstituted arylalkylsilyl of 6 to 20 carbon atoms, R13～R19Adjacent two of them may form a parallel ring structure by bridging;
r is as defined above5～R12、R13～R19When each of the substituted or unsubstituted groups in (1) has a substituent group, the substituent group is one or a combination of two selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C20, heterocycloalkyl of C3-C20, aryl of C6-C60, and heteroaryl of C3-C60.
Further preferably, R is5～R12、R13～R19Independently selected from one or two of hydrogen, deuterium, halogen, cyano, chain alkyl of C1-C30, chain alkyl of deuterated C1-C30, cycloalkyl of C3-C20, cycloalkyl of deuterated C3-C20, alkylsilyl of C0-C20, heterocycloalkyl of C3-C20, heterocycloalkyl of deuterated C3-C20, aryl of C6-C60, aryl of deuterated C6-C60, heteroaryl of C3-C60 and heteroaryl of deuterated C3-C60;
still further preferably, said R5～R12、R13～R19Each independently selected from the group consisting of hydrogen, deuterium, cyano, fluorine atom, trifluoromethyl, trifluoroethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, phenyl, substituted phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylcyclohexyl, 4-methylcyclopentyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, pyridylOne or two of methyl substituted pyridyl, deuterated methyl substituted pyridyl, methoxy, methylamino and ethylamino.
As a more preferred embodiment of the present invention, L is arbitrarily selected from the following groups:
as a preferred embodiment of the present invention, the phosphorescent light-emitting material is a compound represented by any one of general formula (I-1), general formula (I-2) or general formula (I-3):
wherein n is 1 or 2; r1、R2、R3、R4Are as defined in formula (I); r5～R12、R13～R19Are as defined in formula L1 and formula L2.
As a further preferred embodiment of the present invention, in the general formula (I-2), R is as described above5～R12Independently and optionally selected from one or two of hydrogen, deuterium, cyano, fluorine atom, trifluoromethyl, methyl, silicon methyl, trimethylsilyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isobutyl, deuterated tert-butyl, phenyl, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl;
as a further preferred embodiment of the present invention, in the above general formula (I-3), said R13～R19Independently selected from hydrogen, deuterium, fluorine atom, trifluoromethyl, methyl, ethyl, propyl, butyl, tertiary butyl and benzeneOne or two of the group, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylcyclohexyl, 4-methylcyclopentyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, naphthyl, anthracenyl, deuterated phenyl, deuterated naphthyl, deuterated anthracenyl and pyridyl are combined.
As a preferred embodiment of the present invention, in the above general formula (I), general formula (I-1), general formula (I-2) or general formula (I-3):
R1one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms;
R2、R3、R4each independently selected from one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms.
More preferably, R1One or two of methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 4-isopropyl cyclopentyl, deuterated methyl, deuterated ethyl, deuterated propyl, phenyl, biphenyl, benzo, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl; r2、R3、R4Each independently selected from one or two of hydrogen, deuterium, fluorine atom, cyano, trifluoromethyl, methyl, ethyl, propyl, butyl, tertiary butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated butyl, deuterated tertiary butyl, phenyl, biphenyl, acenyl, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl.
In the present specification, the expression of Ca to Cb represents that the group has carbon atoms a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified. In the present invention, unless otherwise specified, the expressions of chemical elements generally include the concept of chemically identical isotopes, for example, the expression of "hydrogen" also includes the concept of chemically identical "deuterium" and "tritium", and carbon (C) includes 12C and 13C, and the description thereof is omitted.
Heteroaryl in this specification refers to an aromatic cyclic group containing a heteroatom, typically selected from N, O, S, P, Si and Se, preferably N, O, S.
In the present specification, the aryl group having 6 to 60 carbon atoms and the heteroaryl group having 3 to 60 carbon atoms are aromatic groups satisfying pi conjugated system unless otherwise specified, and include both monocyclic rings and condensed rings. The monocyclic ring means that at least one phenyl group is contained in the molecule, and when at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are linked by a single bond, such as phenyl, biphenylyl, terphenylyl, and the like, for example; the condensed ring means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are condensed with each other, illustratively, naphthyl, anthryl, phenanthryl, etc.; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl means fused from at least one phenyl group and at least one heteroaryl group, or fused from at least two heteroaryl groups, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like
In the present specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a C6 to C30 aryl group, and exemplary preferred is an aryl group in the group consisting of a phenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a pyrenyl group, a celtyl group, a perylenyl group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, an idophenyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis-or trans-indenofluorenyl group, a trimeric indenyl group, an isotridecyl group, a spirotrimeric indenyl group, and a spiroisotridemic indenyl group. The aryl group having C6 to C60 in the present invention may be a group in which the above groups are bonded by a single bond or/and condensed.
In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, and may be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like. Preferred examples of the heterocyclic ring in the present invention include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole. The heteroaryl group having C3-C60 in the present invention may be a group in which the above groups are bonded by a single bond or/and condensed.
In the present specification, alkyl is not particularly specified, and includes straight-chain alkyl and branched-chain alkyl as well as the concept of cycloalkyl. Examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, pentafluoroethyl, 2,2, 2-trifluoroethyl and the like.
In the present specification, cycloalkyl groups include monocycloalkyl groups and polycycloalkyl groups, and there may be mentioned: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
In the present specification, examples of the C1 to C20 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, more preferably methoxy.
In the present specification, examples of the aryloxy group having C6 to C60 include groups in which each group listed in the above substituted or unsubstituted aryl group having C6 to C60 is linked to oxygen, and specific examples thereof are given by reference to the above examples and are not described herein again.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
As a preferred embodiment of the present invention, the organic phosphorescent light-emitting material is optionally selected from compounds represented by the following structural formula:
the invention provides an organic electrophosphorescent material, which is an imidazopyridine ligand-supported phosphorescent material with a brand-new structure, namely an imidazopyridine structural unit ligand-supported iridium-containing material. The phosphorescent material provided by the invention can effectively solve the problems of low phosphorescent efficiency, poor stability and short service life of the conventional phosphorescent material, improves the phosphorescent quantum efficiency and electroluminescent efficiency of the material, and improves the stability of the material and the service life of devices. The electroluminescent device prepared by the phosphorescent material has the advantages of high purity, high brightness and high efficiency. The material can be used as green phosphorescent luminescent material.
The organic electrophosphorescent material has the following advantages:
the complex is not a traditional common phenylpyridine compound, but introduces an imidazole structure, and introduces a branched chain, wherein the branched chain enables molecules to be in a plane, so that certain distortion exists among ligand molecules, and the distortion of the molecules can effectively slow down efficiency roll-off caused by overhigh doping concentration.
In a second aspect, the present invention provides an organic electroluminescent device prepared using the above phosphorescent material.
The organic electrophosphorescent material is used as a luminescent dye doped in a luminescent main material in a luminescent layer in an organic electroluminescent device. The electroluminescent device prepared by the phosphorescent material has the advantages of high purity, high brightness and high efficiency.
Further preferably, the doping concentration of the phosphorescent material in the host material is 3-12%, more preferably 5-10%, and more preferably 6-8%. When the doping concentration of the phosphorescent light-emitting material in the host material is about 7%, the performance of the device is best. Wherein, the doping concentration is mass percentage concentration.
The organic electroluminescent device comprises a substrate, and an anode layer, a plurality of light-emitting unit layers and a cathode layer which are sequentially formed on the substrate; the light-emitting unit layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a plurality of light-emitting layers are arranged between the hole transport layer and the electron transport layer. The luminescent material of the luminescent layer is the iridium-containing phosphorescent material provided by the invention.
In a third aspect, the invention further provides a display device comprising the organic electroluminescent device.
In a fourth aspect, the invention further provides a lighting device comprising the organic electroluminescent device.
Detailed Description
The technical solution of the present invention will be described in detail by specific examples. The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. The synthesis product is structurally validated and characterized using one or more equipment conventional in the art (including, but not limited to, agilent liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, princeton's electrochemical workstation, haikan's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Nanjing Mike, an optical test system manufactured by Fushida, Suzhou, an optical life test system, an ellipsometer manufactured by Wuhan Yingguan technology), in a manner well known to those skilled in the art.
According to the method for synthesizing the compound and the method for manufacturing the organic electroluminescent device provided by the present invention, a person skilled in the art can use known common means to realize the method, and the present invention is not particularly limited thereto. If not specifically stated, the starting materials for the preparation of solvents, catalysts, bases, etc. may be obtained by published commercial routes or by methods known in the art.
The synthesis of the compounds of the present invention is briefly described below. The compounds represented by the general formula (I) of the present invention can be synthesized by a known organic synthesis method. An exemplary synthetic route is given below, and the synthesis of the compounds of general formula (I) according to the invention can be achieved by the following synthetic methods of the ligands P1-P6 of the compounds of the invention. The synthesis can also be carried out by other known methods, such as further selecting suitable catalyst and solvent, and determining suitable reaction temperature, time, material ratio, etc.
Example 1: ligand P1
Synthesis of (2)
The synthetic route is as follows:
the specific experimental steps are as follows:
under the protection of nitrogen, 120mL of toluene and 60mL of ethanol are added into a 500mL three-necked flask equipped with a condenser tube, a thermometer and a magneton, then aqueous solutions (60mL) of 1-bromo-3-methyl-imidazo [1,5-a ] pyridine (21.1g, 0.1mol), 4-dibenzofuranboronic acid (21.2g, 0.1mol), tetrakis (triphenylphosphine) palladium (1.15g, 1.0mmol) and anhydrous potassium carbonate (27.6g, 0.2mol) are sequentially added, nitrogen is used for protection, then reflux reaction is carried out for 8 hours, after the reaction is finished, toluene is directly used for extraction, water washing is carried out for three times, an organic phase is dried by anhydrous sodium sulfate, the organic phase is directly passed through a silica gel column, and after the column liquid is dried by spin drying, a toluene/ethanol mixed solution is used for crystallization, so that 18.0g P2 is obtained, yield: 60.2 percent.
Elemental analysis (C)20H14N2O): theoretical value C: 80.52%, H: 4.73%, N: 9.39 percent; found value C: 80.48%, H: 4.80%, N: 9.41 percent.
Example 2: ligand P2
Synthesis of (2)
The synthetic route is as follows:
the specific experimental steps are as follows:
to a 500mL three-necked flask equipped with a condenser, a thermometer and a magneton, 300mL of toluene was added under nitrogen, followed by the addition of 1-bromo-3-ethyl-imidazo [1,5-a ] pyridine (22.5g, 0.1mol), 2-methyl-8- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzofuran [2,3-b ] pyridine (30.9g, 0.1mol), tris (dibenzylideneacetone) dipalladium (0.92g, 2.0mmol), tri-tert-butylphosphine (0.8g,4.0mmol), sodium tert-butoxide (14.4g,0.15mol), protected with nitrogen, and then refluxed overnight, concentrated and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and then further purified by column chromatography using a hexane solution of ethyl acetate to give 23.6g P1, yield: 72.2 percent.
Elemental analysis (C)21H17N3O): theoretical value C: 77.04%, H: 5.23%, N: 12.84 percent; found value C: 77.03%, H: 5.23%, N: 12.86 percent.
Example 3: ligand P3
Synthesis of (2)
The synthetic route is as follows:
the specific experimental steps are as follows:
referring to the synthetic procedure of example 1 except for using 1-bromo-3-isopropylimidazo [1,5-a ] pyridine instead of 1-bromo-3-methylimidazo [1,5-a ] pyridine, the other starting materials and procedures were the same as in example 1, yielding ligand P3.
Elemental analysis (C)22H19N3O): theoretical value C: 77.40%, H: 5.61%, N: 12.31 percent; found value C: 77.42%, H: 5.58%, N: 12.30 percent.
Example 4: ligand P4
Synthesis of (2)
The synthetic route is as follows:
the specific experimental steps are as follows:
(1) adding 200mL of N, N-dimethylformamide into a 500mL three-necked flask provided with a condenser, a thermometer and a magneton, then adding 3-cyclohexyl imidazo [1,5-a ] pyridine (20.2g and 0.1mol), dissolving N-bromosuccinimide (17.8g and 0.1mol) in 100mL of DMF, adding into a constant pressure dropping funnel, stirring after nitrogen replacement, cooling to-10 ℃, then dropwise adding DMF solution of N-bromosuccinimide at the temperature of below 0 ℃, finishing dropwise adding, naturally heating and stirring for 2 hours after dropwise adding, then adding 200mL of water, directly carrying out suction filtration to obtain a crude product, fully dissolving the obtained crude product in toluene, concentrating the column solution to obtain 20.4g of P4-1, wherein the yield is as follows: 73.2 percent.
(2) Referring to the synthetic procedure of example 1, except for using P4-1 instead of 1-bromo-3-methylimidazo [1,5-A ] pyridine, the other raw materials and procedures were the same as in example 1, to obtain ligand P4.
Elemental analysis (C)25H23N3O): theoretical value C: 78.71%, H: 6.08%, N: 11.02 percent; found value C: 78.69%, H: 6.10%, N: 11.05 percent.
Example 5: ligand P5
Synthesis of (2)
The synthetic route is as follows:
the specific experimental steps are as follows:
referring to the synthetic procedure of example 1, except for using 1-bromo-3-phenylimidazo [1,5-A ] pyridine instead of 1-bromo-3-methylimidazo [1,5-A ] pyridine, the other starting materials and procedures were the same as in example 1, yielding ligand P5.
Elemental analysis (C)25H17N3O): theoretical value C: 79.98%, H: 4.56%, N: 11.19 percent; found value C: 79.95%, H: 4.56%, N: 11.21 percent.
Example 6: synthesis of Compound I-1
The reaction formula is as follows:
the specific experimental steps are as follows:
into a 250ml three-necked flask equipped with a magnetic stirring and reflux condenser, Ir (acac)3(10mmol, 4.9g), ligand P1(40mmol, 11.93g), glycerol 150mL, N2Heated in an oil bath at 190 ℃ under protection and refluxed for one night. Naturally cooling to room temperature, filtering, washing with water and ethanol in sequence, and drying to obtain a yellow crude product. By CH2Cl2Column separation after dissolution, CH2Cl2Eluting, column passing liquid spin-drying to obtain 4.17g yellow solid with the yield of 38.5%.
Elemental analysis (C)60H39IrN6O3): theoretical value C: 66.47%, H: 3.63%, N: 7.75 percent; found value C: 66.48%, H: 3.72%, N: 7.74 percent.
Example 7: synthesis of Compound I-16
The reaction formula is as follows:
compound I-16 was obtained by following the synthetic procedure of example 6 except that P2 was used in place of P1 and the other starting materials and procedures were the same as those of example 5.
Elemental analysis (C)63H48IrN9O3): theoretical value C: 64.60%, H: 4.13%, N: 10.76 percent; found value C: 64.57%, H: 4.17%, N: 10.81 percent.
Example 8: synthesis of Compound II-51
The reaction formula is as follows:
the specific experimental steps are as follows:
(1) in a 100mL three-necked flask equipped with mechanical stirring, a reflux condenser and a nitrogen gas protector, 5-methyl-2- (4-tolyl) pyridine (15mmol, 2.75g), iridium trichloride hydrate (6mmol, 2.1g), 45mL of ethylene glycol monoethyl ether and 15mL of water were sequentially added. Heated to 110 ℃ under nitrogen for 24 hours at reflux. After natural cooling, 10mL of water is added, the mixture is stirred for 10min, then is filtered, and is washed by water and ethanol in sequence. Drying in vacuo afforded 2.93g of crude M1 as a yellow solid in 82.5% yield.
(2) In a 500mL three-necked flask equipped with a nitrogen blanket, dichloro-bridged intermediate M7(2.93g,2.5mmol) was sequentially added, 50mL of dichloromethane was added, and the mixture was sufficiently stirred, then a 50mL methanol solution of silver trifluoromethanesulfonate (1.6g, 6.25mmol) was added, and the mixture was stirred for 24 hours in the dark, cooled to room temperature, and then filtered with celite, and the filtrate was dried by spinning to obtain a yellowish solid powder M2. The solid was used in the next reaction without further treatment.
(3) In a 250ml three-necked flask, M2(2.0g, 2.6mmol) and ligand P3(2.66g, 7.8mmol) were added followed by 100ml ethanol, the mixture was heated to reflux for 36 hours, the reaction was cooled to room temperature, the resulting yellow solid was filtered, the solid was dissolved in dichloromethane and isolated by column chromatography to give 0.79g of yellow solid in 32.8% yield.
Elemental analysis (C)50H49IrN5O): theoretical value C: 64.70%, H: 5.32%, N: 7.55 percent; found value C: 64.72%, H: 5.29%, N: 7.55 percent.
Example 9: synthesis of Compound II-73
The reaction formula is as follows:
compound II-73 was obtained by following the synthetic procedure of example 8 except that P4 was used in place of P3 and the other starting materials and procedures were the same as those of example 8.
Elemental analysis (C)53H53IrN5O2): theoretical value C: 65.75%, H: 5.52%, N: 7.23 percent; found value C: 65.73%, H: 5.54%, N: 7.25 percent.
Example 10: synthesis of Compound II-129
The reaction formula is as follows:
the specific experimental steps are as follows:
(1) a250 mL three-neck flask equipped with a mechanical stirring device, a reflux condenser and a nitrogen protection device was charged with ligand P5(25mmol,9.4g), iridium trichloride hydrate (10mmol,3.53g), 90mL of ethylene glycol monoethyl ether and 30mL of distilled water in this order. Heated to 110 ℃ under nitrogen for 24 hours at reflux. After natural cooling, 50mL of water is added, the mixture is stirred for 10min, then is filtered, and is washed by water and ethanol in sequence. Drying in vacuo afforded 6.5g of crude M3 as a yellow solid in 73.8% yield.
(2) In a 500mL three-necked flask equipped with a nitrogen blanket, dichloro-bridged intermediate M3(5.28g,3mmol) was sequentially added, 50mL of dichloromethane was added, and the mixture was sufficiently stirred, then a 50mL methanol solution of silver trifluoromethanesulfonate (1.92g, 7.5mmol) was added, and the mixture was stirred for 24 hours in the dark, cooled to room temperature, and then filtered with celite, and the filtrate was dried by spinning to obtain a yellowish solid M4. The solid was used in the next reaction without further treatment.
(3) In a 100ml three-necked flask, M4(2.3g, 2.0mmol) and 5-methyl-2- (4-tolyl) pyridine (6mmol, 1.1g) were added followed by 50ml ethanol, the mixture was heated under reflux for 36 hours, the reaction was cooled to room temperature, the resulting yellow solid was filtered, this solid was dissolved in dichloromethane, and column chromatography gave 0.79g of a yellow-green solid in 35.2% yield.
Elemental analysis (C)63H44IrN7O2): theoretical value C: 67.36%, H: 3.95%, N: 8.73 percent; found value C: 67.28%, H: 4.05%, N: 8.80 percent.
Example 11: synthesis of Compound III-38
The reaction formula is as follows:
the specific experimental steps are as follows:
to a 250mL three-necked flask equipped with a magnetic stirring and reflux condenser were added intermediate M3(3mmol, 5.28g), 2,2,6, 6-tetramethyl-3, 5-heptanedione (9mmol, 1.65g), anhydrous sodium carbonate (12mmol, 1.3g), and 100mL of ethylene glycol monoethyl ether in this order. N is a radical of2Heated to reflux for 24 hours in an oil bath at 120 ℃ under protection. Naturally cooling to room temperature, filtering, washing with ethanol, and drying to obtain a yellow crude product. By CH2Cl2Column separation after dissolution, eluent CH2Cl2Washing and solvent suction drying gave 1.81g of yellow powder, 28.2% yield.
Elemental analysis (C)61H51IrN6O4): theoretical value C: 65.16%, H: 4.57%, N: 7.47%; found value C: 65.12%, H: 4.62%, N: 7.52 percent.
Other specific phosphorescent compounds listed in the present invention were synthesized with reference to the above synthesis method.
The organic electroluminescent device has a structure consistent with that of the organic electroluminescent device in the prior art, and comprises an anode layer, a plurality of light-emitting functional layers and a cathode layer; the plurality of light-emitting functional layers at least comprise a light-emitting layer, and the light-emitting functional layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer and an electron transport layer, wherein the light-emitting layer contains the organic compound of the invention.
In embodiments in which organic electroluminescent devices are specifically prepared, a substrate may be used either below the anode or above the cathode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The anode electrode may be formed by sputtering or depositing a material serving as an anode on a substrate. An oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The following are examples of organic electroluminescent devices prepared according to the invention using representative compounds of the invention:
device example 1
The embodiment provides an OLED green light device, the structure of which is as follows: ITO/HATCN (2nm)/HT01(60nm)/TAPC (40nm)/DIC-TRZ: 7% phosphorescent light-emitting material of the invention (40nm)/TPBI (5nm) ET: QLi (1:1) (30nm)/LiF (1 nm)/Al.
Wherein: 2nm, 60nm, 40nm, 30nm, etc. represent the thickness of the functional layer; the luminescent dye material in the EML layer used the compound i-1 of the present invention prepared in the above synthesis example 1.
The molecular structure of each functional layer material is as follows:
the specific preparation process of the OLED green device in this embodiment is as follows:
(1) carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1:1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 5 × 10-5～9×10-3Pa, carrying out vacuum evaporation on the anode layer film to form HATCN as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 2 nm; then, evaporating a first hole layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 60 nm; then evaporating a second hole transport layer TAPC (tantalum polycarbonate), wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
(3) the EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material DIC-TRZ and a dye material I-1 of the invention, the doping concentration is 7%, an organic light emitting layer of the device is formed, the evaporation rate is 0.2nm/s, and the total evaporation film thickness is 40 nm; then 5nm of TPBI is evaporated to form a hole blocking layer, and the evaporation rate is 0.1 nm/s;
(4) then evaporating ET: QLi with the mass ratio of 1:1 on the hole blocking layer as an electron transport material of an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm;
(5) LiF with the thickness of 1nm is sequentially subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
An organic electroluminescent device numbered as OLED-1 was prepared according to the above procedure.
Device example 2 to device example 6:
the specific preparation method is the same as that of the device example 1, and only the luminescent dye material in the step (3) is replaced by the compounds I-16, II-51, II-73, II-129 and III-38 of the invention respectively, and the details are shown in the following table 1, so that the organic electroluminescent devices numbered as OLED-2 to OLED-6 are prepared respectively.
Device comparative example 1:
following the same procedure as described above for device example 1, except that the light-emitting layer dye material in step (3) was replaced with a prior art compound GD-01 of similar structure, comparative devices OLED-9, GD-01 were prepared having the following structural formula:
the data of the performance test of the organic electroluminescent devices prepared in the above examples 1 to 6 and comparative example 1 of the present invention are detailed in the following table 1.
Table 1:
from the above results, it is seen that the luminous efficiency of the corresponding device is improved compared to GD-01, and that compounds of different ligand modes: on one hand, the colors of the emitted light can be adjusted, the photoelectric properties of the corresponding devices can be obviously influenced, the light emitting properties of the compound and the wide adjustability of device data are shown, and solutions can be provided according to different customer requirements. The organic electroluminescent device prepared by the phosphorescent material has the advantages of high purity, high brightness and high efficiency.
The present invention is illustrated in detail by the above examples, but the present invention is not limited to the above detailed methods. It is obvious to those skilled in the art that any modification of the present invention, equivalent substitution of each raw material and addition of auxiliary components, selection of specific modes, etc., of the product of the present invention fall within the protection scope of the present invention.
Claims (10)
1. An organic electrophosphorescent material has a structure shown as the following formula (I):
in formula (I): r2、R3、R4Each represents a substituent group ranging from single substitution to the maximum allowable number of substitutions;
R2、R3、R4each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms;
R3、R4can be connected in a ring, or R3、R4Each independently and the connected ring structure can form a fused ring structure through bridging, when the fused ring structure is formed, the fused ring structure can be any one of a substituted or unsubstituted five-membered aromatic ring, a substituted or unsubstituted six-membered aromatic ring, a substituted or unsubstituted five-membered heteroaromatic ring and a substituted or unsubstituted six-membered heteroaromatic ring, the heteroatom in the five-membered heteroaromatic ring or the six-membered heteroaromatic ring is at least one, and the heteroatom is selected from an oxygen atom, a nitrogen atom or a sulfur atom;
R1one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms;
r is as defined above1、R2、R3、R4Wherein each substituted or unsubstituted group hasWhen the substituent group is selected from deuterium, halogen, cyano, chain alkyl of C1-C10, cycloalkyl of C3-C10, heterocycloalkyl of C3-C10, aryl of C6-C30 and heteroaryl of C3-C30, or the combination of two of the above R3、R4When the ring structures connected with each other have a substituent group, the substituent group is one or a combination of two of deuterium, halogen, cyano, chain alkyl of C1-C10, cycloalkyl of C3-C10, heterocycloalkyl of C3-C10, aryl of C6-C30 and heteroaryl of C3-C30;
Z1～Z7independently selected from a nitrogen atom or a carbon atom;
l is a monovalent, bidentate anion wherein the linking atoms X, Y are each independently selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms;
n is 1, 2 or 3.
2. The organic electrophosphorescent material of claim 1, wherein Z is1～Z6One or two of which are nitrogen atoms and the others are carbon atoms, and Z7Is a carbon atom;
preferably, Z is1～Z4One or two of which are nitrogen atoms and the others are carbon atoms, and Z5～Z7Are all carbon atoms;
or preferably, said Z1、Z3、Z4One or two of which are nitrogen atoms and the others are carbon atoms, and Z5～Z7Are all carbon atoms;
or preferably, said Z1Is a nitrogen atom, Z2～Z7Are all carbon atoms.
3. The organic electrophosphorescent material of claim 1, wherein L is one of a substituted or unsubstituted phenylpyridyl group, a substituted or unsubstituted acetylacetonate group; when L has a substituent group, the substituent group is one or the combination of two of deuterium, halogen, cyano, amino, chain alkyl of C1-C30, alkoxy of C1-C30, cycloalkyl of C3-C20, heterocycloalkyl of C3-C20, aryl of C6-C60 and heteroaryl of C3-C60;
preferably, L is a group of formula L-1 or formula L-2:
in L-1, R5～R12Each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted deuterated alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted deuterated aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 0 to 20 carbon atoms, substituted or unsubstituted alkyl substituted with carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atoms, and substituted or unsubstituted aryl substituted with carbon atoms, One of substituted or unsubstituted arylalkylsilyl groups having 6 to 20 carbon atoms, R5～R12Adjacent two of them may form a parallel ring structure by bridging;
in the formula L-2, R13～R19Each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 0 to 20 carbon atoms, substituted or unsubstituted arylalkylsilyl having 6 to 20 carbon atoms, R is independently selected from13～R19Adjacent two of them may form a parallel ring structure by bridging;
r is as defined above5～R12、R13～R19When each of the substituted or unsubstituted groups in (1) has a substituent group, the substituent group is one or a combination of two selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C20, heterocycloalkyl of C3-C20, aryl of C6-C60, and heteroaryl of C3-C60.
4. The organic electrophosphorescent material of claim 3, wherein R is an alkyl group5～R12、R13～R19Independently selected from one or two of hydrogen, deuterium, halogen, cyano, chain alkyl of C1-C30, chain alkyl of deuterated C1-C30, cycloalkyl of C3-C20, cycloalkyl of deuterated C3-C20, alkylsilyl of C0-C20, heterocycloalkyl of C3-C20, heterocycloalkyl of deuterated C3-C20, aryl of C6-C60, aryl of deuterated C6-C60, heteroaryl of C3-C60 and heteroaryl of deuterated C3-C60;
preferably, said R is5～R12、R13～R19Each independently selected from one or two of hydrogen, deuterium, cyano, fluorine atom, trifluoromethyl, trifluoroethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, phenyl, substituted phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylcyclohexyl, 4-methylcyclopentyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, pyridyl, methyl-substituted pyridyl, deuterated methyl-substituted pyridyl, methoxy, methylamino and ethylamino.
5. The organic electrophosphorescent material of claim 1, wherein L is selected from one of the following groups:
6. the organic electrophosphorescent material of claim 1, wherein the phosphorescent material is a compound represented by any one of general formula (i-1), general formula (i-2) or general formula (i-3):
wherein n is 1 or 2; r1、R2、R3、R4Are as defined in formula (I); r5～R12、R13～R19Are as defined in formula L1 and formula L2;
preferably, in the formula (I-2), R is5～R12Independently and optionally selected from one or two of hydrogen, deuterium, cyano, fluorine atom, trifluoromethyl, methyl, silicon methyl, trimethylsilyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isobutyl, deuterated tert-butyl, phenyl, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl;
preferably, in the formula (I-3), R is13～R19Independently selected from hydrogen, deuterium, fluorine atom, trifluoromethyl, methyl, ethyl, propyl, butyl, tert-butyl, phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylcyclohexyl, 4-methylcyclopentyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl, deuterated anthrylOr a combination of two of them.
7. The organic electrophosphorescent material according to claim 1 or 6, wherein in the formula (I), the formula (I-1), the formula (I-2) or the formula (I-3):
R1one selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms;
R2、R3、R4each independently selected from one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms.
Preferably, R1One or two of methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, 4-isopropyl cyclopentyl, deuterated methyl, deuterated ethyl, deuterated propyl, phenyl, biphenyl, benzo, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl; r2、R3、R4Each independently selected from one or two of hydrogen, deuterium, fluorine atom, cyano, trifluoromethyl, methyl, ethyl, propyl, butyl, tertiary butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated butyl, deuterated tertiary butyl, phenyl, biphenyl, acenyl, naphthyl, anthryl, deuterated phenyl, deuterated naphthyl and deuterated anthryl.
8. The organic electrophosphorescent material of claim 1, having a structural formula shown below:
9. an organic electroluminescent device comprising an anode, a cathode and one or more light-emitting functional layers interposed between the anode and the cathode, wherein the light-emitting functional layers contain therein the organic electrophosphorescent luminescent material according to any one of claims 1 to 8;
preferably, the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the light-emitting layer comprises a host material and a dye material, the dye material is the organic electrophosphorescent material according to any one of claims 1 to 8, and the doping percentage of the organic electrophosphorescent material in the host material is 3 to 12%;
preferably, the doping percentage of the organic electrophosphorescent luminescent material in the main material is 5-10%;
more preferably, the doping percentage of the organic electrophosphorescent luminescent material in the main material is 6-8%;
most preferably, the doping percentage of the organic electrophosphorescent material in the host material is 7%.
10. A display device characterized by comprising the organic electroluminescent device according to claim 9.
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| US20060224007A1 (en) * | 2005-03-31 | 2006-10-05 | Eastman Kodak Company | Synthesis of organometallic cyclometallated transition metal complexes |
| US20060223997A1 (en) * | 2005-03-31 | 2006-10-05 | Eastman Kodak Company | Synthesis of organometallic cyclometallated transition metal complexes |
| US20160380216A1 (en) * | 2015-06-25 | 2016-12-29 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
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