CN113501824A - Fused heterocyclic organic compound and organic photoelectric element using same - Google Patents
Fused heterocyclic organic compound and organic photoelectric element using same Download PDFInfo
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- CN113501824A CN113501824A CN202110646005.1A CN202110646005A CN113501824A CN 113501824 A CN113501824 A CN 113501824A CN 202110646005 A CN202110646005 A CN 202110646005A CN 113501824 A CN113501824 A CN 113501824A
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- -1 heterocyclic organic compound Chemical class 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000004826 dibenzofurans Chemical class 0.000 claims description 3
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 239000010410 layer Substances 0.000 abstract description 47
- 239000002346 layers by function Substances 0.000 abstract description 6
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 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 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 150000002894 organic compounds Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- BFXLJWUGRPGMFU-UHFFFAOYSA-N dipropoxyphosphinothioyl n,n-diethylcarbamodithioate;sulfane Chemical compound S.CCCOP(=S)(OCCC)SC(=S)N(CC)CC BFXLJWUGRPGMFU-UHFFFAOYSA-N 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 2
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- GSUCEGNAROQSGU-UHFFFAOYSA-N 2-bromodibenzo-p-dioxin Chemical compound C1=CC=C2OC3=CC(Br)=CC=C3OC2=C1 GSUCEGNAROQSGU-UHFFFAOYSA-N 0.000 description 1
- NEKRENTXSQBYTN-UHFFFAOYSA-N 3-bromo-2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC(Br)=C1NC1=CC=CC=C1 NEKRENTXSQBYTN-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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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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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a fused heterocyclic organic compound and an organic light-emitting device using the same, wherein the structural formula of the fused heterocyclic organic compound is shown as 1:
Ar1、Ar2、R1to R4Understood by reference to the detailed description provided herein; the fused heterocyclic organic compound is applied to a functional layer of an organic electroluminescent diode, and is particularly used as a main material of a light-emitting layer, so that the current efficiency of a light-emitting element is improved, the service life of the light-emitting element is prolonged, and the light-emitting element has good commercial prospect.
Description
Technical Field
The present invention relates to a fused heterocyclic organic compound and an organic light emitting tube device using the same, and more particularly, to a soluble organic compound having excellent color purity and high luminance and light emitting efficiency and an OLED device using the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. The OLED has a series of advantages of autonomous light emission, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, is widely noticed due to potential application in new-generation displays and lighting technologies, and has a very wide application prospect. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from positive and negative electrodes and then migrate, recombine and attenuate in an organic material to generate light emission. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high-efficiency electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
Luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have been commercially used due to their excellent properties, but as host materials in organic electroluminescent devices, it is more important to have good hole transport properties in addition to the triplet energy level higher than that of the guest materials, which prevents the energy reverse transfer of exciton transition release. Currently, materials having both high triplet energy levels and good hole mobility in the host material are still lacking. Therefore, how to design a new main material with better performance is a problem to be solved urgently by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide a fused heterocyclic organic compound and an organic light emitting device using the same, the organic light emitting device using the fused heterocyclic organic compound of the present invention having excellent pure chromaticity, high luminance and excellent light emitting efficiency.
The invention provides a fused heterocyclic organic compound, the structural formula of which is shown as 1,
in the above structural formula, Ar1Selected from substituted or unsubstituted C6-C90 heteroaryl, heterocyclic group or amine series containing more than two nitrogen atoms; ar (Ar)2Is a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted arylcarbazole;
R1、R2、R3and R4Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring, and substituted or unsubstituted C4-C30 heteroaryl (wherein, at least one of R1 and R2, R2 and R3, R3 and R4 must form a ring or a heterocyclic ring).
Preferably, the fused heterocyclic organic compound has a structural formula shown in formula 1-1 to formula 1-18:
wherein Ar is1Selected from the group consisting of substituted or unsubstituted C6-C90 heteroaryl, heterocyclyl, or amine series containing two or more nitrogen atoms; ar (Ar)2Is a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted arylcarbazole;
R5、R6and Ar3Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C4-C30 heteroaryl；
X1Represents oxygen (O), sulfur (S), (NR 7); wherein R7 is substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl.
Further preferred is a fused heterocyclic organic compound having the structure of Ar1Selected from the following structures:
wherein, X2、X3And X4Represents nitrogen (N) or carbon (CR7), and at least two of which are N; l is1Is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative; r7、R8、R9And R10Independently selected from one of hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof
In a further preferred mode, the fused heterocyclic organic compound is independently selected from the following compounds, but does not represent that the present invention is limited thereto:
the invention also provides application of the organic compound in an organic light-emitting device.
Preferably, the organic light emitting device comprises an anode, a cathode and a plurality of organic functional layers positioned between the anode and the cathode, wherein the organic functional layers contain the compound containing the carbazole series.
The invention has the beneficial effects that:
the invention provides a carbazole series-containing compound, which has a structure shown in a formula 1, wherein an electron-rich structure in the carbazole series compound has great influence on the photoelectric property of the whole compound molecule, so that unnecessary vibration energy loss is reduced, and high-efficiency luminous performance is realized. By adjusting substituent groups, the compound has better thermal stability and chemical properties. The compound containing carbazole series has the advantages of simple preparation method and easily obtained raw materials, and can meet the industrial requirements.
The carbazole series compounds are prepared into devices, particularly used as main materials, the devices have the advantages of low driving voltage and high luminous efficiency, and are superior to the conventional common OLED devices.
In the present invention, the organic electroluminescent device preferably includes an anode, a cathode, and several organic layers located between the anode and the cathode, and the "organic layer" refers to a term of all layers disposed between the anode and the cathode in the organic electroluminescent device. The organic layer may be a layer having a hole characteristic and a layer having an electron characteristic. For example, the organic layer includes one or more of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a functional layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the hole transport layer may be formed of a conventional hole injection material, a hole transport material, or a material having both hole injection and hole transport functions, in addition to the electron-generating material.
For example, the organic layer includes a light emitting layer, and the light emitting layer includes one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. In the present invention, the compound for an organic electroluminescent device can be used as a fluorescent host, as a fluorescent dopant, and as both a fluorescent host and a fluorescent dopant.
In the present invention, the light emitting layer may be a red, yellow or blue light emitting layer. In the present invention, when the light-emitting layer is a light-emitting layer, an organic electroluminescent device having high efficiency, high resolution, high luminance and long life can be obtained by using the above-mentioned compound for an organic electroluminescent device as a host.
In the present invention, the organic electroluminescent diode device of the organic compound is characterized in that the organic electroluminescent diode device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode, which are sequentially deposited, and the organic compound is used as a host material of the light emitting layer.
The present invention is not particularly limited in the method for preparing the organic electroluminescent device, and may be prepared by using a method and materials for preparing a light emitting device, which are well known to those skilled in the art, in addition to the organic compound of formula 1.
Detailed Description
In order to make the technical means, the creation characteristics, the achievement purposes and the effects of the invention easy to understand, the invention is further described with the specific embodiments.
Example 1: synthesis of Compound 295
(1) Synthesis of intermediate 295-1
A500 mL reaction flask was charged with benzaldehyde (2.12g,20mmol), 6-bromo-N1-phenylbenzene-1, 2-diamine (5.27g,20mmol), tetrakis (triphenylphosphine) palladium (5 mol%), sodium metabisulfite (5.70g,30mmol), and dichloroethane (200 mL). Reflux for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was passed through silica gel column to obtain intermediate 295-1(5.94g, yield 85%). LC-MS: M/Z348.03 (M +).
(2) Synthesis of intermediate 295-3
A500 mL reaction flask was charged with intermediate 295-1(21.44g,61.4mmol), 295-2(12.36g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 90 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was passed through silica gel column to obtain intermediate 295-3(18.30g, yield 70%). LC-MS: M/Z425.09 (M +).
(3) Synthesis of intermediate 295-4
295-3(2.13g,5.00mmol), triethyl phosphite (1.25g,7.35mmol) were added to a 250ml reaction flask and reacted overnight at 145 ℃ under nitrogen. The reaction was stopped, cooled and 2M HCl was added, stirred to a full white color and extracted with a small amount of DCM. The organic phase was taken out by liquid separation and turned to oil. Silica funnel, DCM: PE ═ 1: and 3, flushing. The solvent was dried by spinning and recrystallized to obtain 295-4(1.62g, yield 82%) as a white powdery solid. LC-MS: M/Z393.10(M +).
(4) Synthesis of intermediate 295-5
To a 500mL reaction flask were added intermediate 295-4 (24.18g,61.4mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (17.63g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was passed through silica gel column to obtain intermediate 295-5(3.97g, yield 65%). LC-MS: M/Z600.23(M +).
(5) Synthesis of Compound 295
A250 mL three-necked flask was charged with intermediate 295-5(12.01g, 20mmo1), 2-chloro-4-phenylquinazoline 4.81g, 20mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After the reaction was completed, the reaction solution was cooled to room temperature, and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then subjected to silica gel column to obtain 295(8.53g, yield 53%). LC-MS: M/Z804.30(M +).
Example 2: synthesis of Compound 297
Compound 297 was synthesized by the method of reference example 1 to obtain compound 297(8.85g, yield 55%). LC-MS: M/Z804.28 (M +).
Example 3: synthesis of Compound 313
Compound 313 was synthesized by the method of reference example 1 to give compound 313(8.69g, yield 54%). LC-MS: M/Z804.30(M +).
Example 4: synthesis of Compound 315
Compound 315 was synthesized by the method of reference example 1 to obtain compound 315(7.40g, yield 46%). LC-MS: M/Z804.31 (M +).
Example 5: synthesis of Compound 317
Compound 317 was synthesized by the method of reference example 1 to obtain compound 317(7.00g, yield 48%). LC-MS: M/Z729.24(M +).
Example 6: synthesis of Compound 325
(1) Synthesis of intermediate 325-1
A500 mL reaction flask was charged with intermediate 2-bromodibenzo [ b, e ] [1,4] dioxin (16.15g,61.4mmol), 295-2(12.36g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 90 ℃ and reacts for 12 hours under the protection of nitrogen. After the reaction was completed, the reaction solution was cooled to room temperature, and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain intermediate 325-1(13.56g, yield 65%). LC-MS: M/Z339.03 (M +).
(2) Synthesis of intermediate 325-2
302-1(1.70g,5.00mmol), triethyl phosphite (1.25g,7.35mmol) were added to a 250ml reaction flask and reacted overnight at 145 ℃ under nitrogen. The reaction was stopped, cooled and 2M HCl was added, stirred to a full white color and extracted with a small amount of DCM. The organic phase was taken out by liquid separation and turned to oil. Silica funnel, DCM: PE ═ 1: and 3, flushing. The solvent was dried by spinning and recrystallized to give 325-2(1.20g, yield 78%) as a white powdery solid. LC-MS: M/Z307.04 (M +).
(3) Synthesis of intermediate 325-3
A500 mL reaction flask was charged with intermediate 302-2(18.89g,61.4mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (17.63g,61.4mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol), 1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After the reaction was completed, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain intermediate 325-3(19.90g, yield 63%). LC-MS: M/Z514.17 (M +)
(4) Synthesis of Compound 325
A250 mL three-necked flask was charged with intermediate 302-3(10.29) g,20mmol), 2-chloro-4-phenylquinazoline 4.81g, 20mmol, tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8g,33.6mmol) and o-xylene (80 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After the reaction was completed, the reaction solution was cooled to room temperature, and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then subjected to silica gel column to obtain compound 302(7.19g, yield 50%). LC-MS: M/Z718.24 (M +).
Implementation 7: synthesis of compound 326
Compound 326 was synthesized by the method of reference example 1 to obtain compound 326(6.46g, yield 45%). LC-MS: M/Z718.23 (M +).
Example 8: synthesis of compound 327
Compound 327 was synthesized by the method of reference example 1 to obtain compound 327(5.92g, yield 46%). LC-MS: M/Z643.19 (M +).
Example 9: synthesis of Compound 328
Compound 328 was synthesized by the method of reference example 1 to give compound 328(6.30g, yield 49%). LC-MS: M/Z643.18 (M +).
Device embodiments
(I) Evaluation of luminescent Material devices
The compounds of the respective organic layers used in the device examples are as follows:
1. first embodiment
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate is then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set at 1X 10-6 Torr. Thereafter on an ITO substrate
Compound (I)
And
the sequence of (a) and (b) forming layers of organic material.
2. Second embodiment
An organic light-emitting device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound 297 from the compound 295 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 313 instead of compound 295 of the first embodiment.
4. Fourth embodiment
An organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 315 instead of compound 295 of the first embodiment.
5. Fifth embodiment
Method 295, which is the same as described above with respect to the first embodiment, is replaced with compound 317.
6. Sixth embodiment
An organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound 325 from the compound 295 of the first embodiment.
7. Seventh embodiment
An organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 326 from compound 295 of the first embodiment.
8. Eighth embodiment
In the same manner as in the first embodiment described above, 295 was replaced with 327.
9. Ninth embodiment
An organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 328 from compound 295 of the first embodiment.
10. Comparative example 1
An organic light-emitting device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH1 from the compound 295 of the first embodiment.
11. Comparative example 2
An organic light-emitting device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH2 from the compound 295 of the first embodiment.
12. Comparative example 3
An organic light-emitting device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH3 from the compound 295 of the first embodiment.
13. Comparative example 4
An organic light-emitting device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH4 from the compound 295 of the first embodiment.
14. Comparative example 5
An organic light-emitting device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH5 from the compound 295 of the first embodiment.
15. Comparative example 6
An organic light-emitting device of a comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH6 from the compound 295 of the first embodiment.
The fabricated organic light emitting device was tested for voltage, efficiency and lifetime under a current condition of 10mA/cm 2.
Table 1 shows the performance test results of the organic light emitting devices prepared in the examples of the present invention and the comparative examples.
TABLE 1
As shown in table 1, the device also operated efficiently at the same voltage. And compared with the comparative example, the current efficiency of the embodiment is greatly improved and the service life is obviously prolonged.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (10)
1. A fused heterocyclic organic compound, wherein the fused heterocyclic organic compound has a structural formula shown in formula 1:
in the above structural formula, Ar1Selected from the group consisting of substituted or unsubstituted C6-C90 heteroaryl, heterocyclyl, or amine series containing two or more nitrogen atoms; ar (Ar)2Is a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted arylcarbazole;
R1、R2、R3and R4Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring, and substituted or unsubstituted C4-C30 heteroaryl (wherein, at least one of R1 and R2, R2 and R3, R3 and R4 must form a ring or a heterocyclic ring).
2. A fused heterocyclic organic compound having a structural formula shown in formula 1-1 to formula 1-18:
wherein Ar is1Selected from the group consisting of substituted or unsubstituted C6-C90 heteroaryl, heterocyclyl, or amine series containing two or more nitrogen atoms; ar (Ar)2Is a substituted or unsubstituted dibenzothiophene, dibenzofuran or carbazole series of substances;
R5、R6and Ar3Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl;
X1represents oxygen (O), sulfur (S), (NR 7); wherein R7 is substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl.
3. A fused heterocyclic organic compound according to claim 1 or 2, wherein Ar in the structural formula1One selected from the following structures:
wherein, X2、X3And X4Represents nitrogen (N) or carbon (CR7), and at least two of which are N; l is1Is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative; r7、R8、R9And R10Independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof.
4. A fused heterocyclic organic compound according to any one of claims 1 to 3, characterized in that said fused heterocyclic organic compound is independently selected from the following compounds:
5. an organic photoelectric element, wherein the organic photoelectric element is an organic electroluminescent device, the light-emitting device comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, and the fused heterocyclic organic compound according to any one of claims 1 to 5 is used as a host material of the light-emitting layer.
6. The organic photoelectric element according to claim 5, wherein the fused heterocyclic organic compound according to any one of claims 1 to 4 is used alone or in combination with other compounds.
7. The organic photoelectric element according to claim 5, wherein the fused heterocyclic organic compound according to any one of claims 1 to 4 is used as a light-emitting layer or an active layer.
8. The organic photoelectric element according to claim 5, wherein the fused heterocyclic organic compound according to any one of claims 1 to 4 is used as a hole-blocking layer.
9. The organic photoelectric element according to claim 5, wherein the fused heterocyclic organic compound according to any one of claims 1 to 4 is used as an electron transporting layer.
10. A display or lighting device comprising the organic electroluminescent element according to any one of claims 5 to 9.
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