CN114057706A - Organic compound containing triazine structure and application thereof - Google Patents
Organic compound containing triazine structure and application thereof Download PDFInfo
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- CN114057706A CN114057706A CN202010764904.7A CN202010764904A CN114057706A CN 114057706 A CN114057706 A CN 114057706A CN 202010764904 A CN202010764904 A CN 202010764904A CN 114057706 A CN114057706 A CN 114057706A
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- 150000002894 organic compounds Chemical class 0.000 title claims description 34
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims description 30
- 239000000463 material Substances 0.000 claims abstract description 141
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- -1 triazine compound Chemical class 0.000 claims abstract description 16
- 238000002347 injection Methods 0.000 claims description 34
- 239000007924 injection Substances 0.000 claims description 34
- 230000000903 blocking effect Effects 0.000 claims description 29
- 230000005525 hole transport Effects 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 15
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000005561 phenanthryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 16
- 238000001704 evaporation Methods 0.000 abstract description 14
- 230000008020 evaporation Effects 0.000 abstract description 14
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 13
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 12
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract description 12
- 230000009477 glass transition Effects 0.000 abstract description 9
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 150000003918 triazines Chemical class 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 209
- 239000000758 substrate Substances 0.000 description 26
- 239000010408 film Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 18
- 238000012360 testing method Methods 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 125000004986 diarylamino group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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- 125000005259 triarylamine group Chemical group 0.000 description 3
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- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical class CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- 101100072645 Arabidopsis thaliana IPS3 gene Proteins 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- WBXRMTQYTFJLRN-UHFFFAOYSA-N N-[4-(3-dibenzofuran-4-ylphenyl)phenyl]-4-phenyl-N-(4-phenylphenyl)aniline Chemical compound O1C2=C(C=CC=C2)C2=C1C(=CC=C2)C1=CC=CC(=C1)C1=CC=C(C=C1)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 WBXRMTQYTFJLRN-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 101710110702 Probable chorismate pyruvate-lyase 1 Proteins 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
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- 150000001448 anilines Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
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- 125000005266 diarylamine group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- 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]
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Abstract
The invention discloses a triazine compound and application thereof, belonging to the technical field of semiconductor materials. The compound takes dibenzofuran or dibenzothiophene connected triazine derivatives as a core, and has the characteristics of higher glass transition temperature, molecular thermal stability, good electron mobility, lower evaporation temperature, proper HOMO/LUMO energy level and the like. When the compound is used as a material of an organic electroluminescent device, the driving voltage, the current efficiency and the service life of the device are obviously improved.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to an organic compound containing a triazine structure and application thereof in an organic electroluminescent device.
Background
The Organic Light Emission Diodes (OLED) technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED device has a sandwich-like structure and comprises electrode material film layers and organic functional materials sandwiched between different electrode film layers, and various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting device and an electric field acts on positive and negative charges in the organic layer functional material film layer, the positive and negative charges are further compounded in the light-emitting layer, and OLED electroluminescence is generated.
Currently, the OLED display technology has been applied in the fields of smart phones, tablet computers, and the like, and further will be expanded to the large-size application fields of televisions and the like. However, compared with the actual product application requirements, the performances of the OLED device, such as light emitting efficiency and service life, need to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material. In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, and the like are required, and as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, and the like are required. For OLED devices, electrons are injected from the cathode and then transferred through the electron transport layer to the host material where they recombine with holes, generating excitons. Therefore, the injection capability and the transmission capability of the electron transport layer are improved, the driving voltage of the device is favorably reduced, and high-efficiency electron-hole recombination efficiency is obtained. Therefore, the electron transport layer is very important, and it is required to have a high electron injection ability, a transport ability, and high durability of electrons.
The heat resistance and film stability of the material are also important for device lifetime. A material having low heat resistance is not only easily decomposed at the time of material evaporation, but also thermally decomposed by heat generated from the device at the time of device operation, and causes material deterioration. Under the condition of poor phase stability of the material film, the material is also subjected to film crystallization in a short time, so that the organic film layer is directly subjected to layer separation, and the device is degraded. Therefore, the material used is required to have high heat resistance and good film stability.
With the remarkable progress of OLED devices, the required performance of materials is increasing, and not only is good material stability required, but also good efficiency and lifetime are required at low driving voltage. However, the heat resistance stability of the current electron transport materials is insufficient, and the electron resistance of the materials is defective, so that the materials are separated or decomposed in phase when the device is operated.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides an organic compound containing a triazine structure and applications thereof.
An object of the present invention is an organic compound having a triazine structure, which has a structure represented by general formula (1):
in the general formula (1), Ar1～Ar3Is represented as C6-C30The aryl group of (a), preferably represented by one of phenyl, biphenyl, naphthyl, phenanthryl or anthracyl, may be the same or different;
r is independently hydrogen or C6-C30Aryl of (2), preferablyOptionally represented by phenyl;
x represents O or S;
n represents 0 or 1.
It is another object of the present invention to provide a method for preparing an organic compound having a triazine structure according to the present invention.
It is a further object of the present invention to provide the use of the organic compounds according to the invention containing triazine structures as electron transport layer materials in organic electroluminescent devices.
It is a further object of the present invention to provide the use of the organic compounds containing triazine structures according to the invention as host materials for the light-emitting layer in organic electroluminescent devices.
It is still another object of the present invention to provide an organic electroluminescent device comprising the organic compound having a triazine structure according to the present invention.
It is a further object of the present invention to provide a display element comprising an organic electroluminescent device according to the present invention.
Technical effects
The compound takes specific sites of dibenzofuran or dibenzothiophene connected with triazine as a core, has higher glass transition temperature, electron tolerance, molecular thermal stability and proper HOMO/LUMO energy level, and has lower evaporation temperature and good electron mobility, so that when the compound is used as a main body material or an electron transport material of an OLED functional layer, the photoelectric property of an OLED device can be effectively improved, and the service life of the device can be effectively prolonged.
Compounds formed by linking specific sites of triazine and dibenzofuran or dibenzothiophene as a parent nucleus exhibit excellent performance. Due to the connection of specific sites of triazine and dibenzofuran or dibenzothiophene, the LUMO electron cloud distribution of the material can be further delocalized, the electron-resistant property of the material can be improved, and the electron stability of the material can be effectively improved. In addition, the parent nucleus can increase the weak interaction in molecules, effectively reduce the vapor deposition temperature of the molecules and improve the thermal durability of the material. Furthermore, the parent nucleus can inhibit pi-pi accumulation among molecules, so that the electron mobility of the molecules is obviously improved, and the driving voltage of the device is reduced. In addition, due to the existence of the electricity absorption conjugation effect of the parent nucleus, the glass transition temperature of the material is raised, and the film stability of the material is effectively raised. Therefore, the triazine and the compound formed as a mother nucleus are connected with the specific site of the dibenzofuran or dibenzothiophene, so that the driving voltage of the device can be effectively reduced, the efficiency of the device can be improved, and the service life of the device can be prolonged.
The compound adopted by the invention is connected as a mother nucleus through a specific site of triazine and dibenzofuran or dibenzothiophene. As can be understood from the examples (described later), the compound having the above structure has a high glass transition point Tg (e.g., 120 ℃ or higher), a low evaporation temperature (e.g., less than 360 ℃), and a high electron mobility (more than 5.0. multidot. E-4 cm)2Vs) having stable film stability, excellent heat resistance and higher electron mobility.
In addition, compared with the LUMO energy level (2.9-3.0 eV) of a common electron transport material, the compound has a deeper LUMO energy level (> 3.1 eV). Under the action of an electric field or heat energy, the compound can easily reduce and dissociate lithium ions in the lithium complex due to the strong electricity absorption and conjugation effects, so that the electron injection capability is improved. Therefore, the compound as an electron transport material has excellent electron transport capability and good electron injection property, can effectively reduce the driving voltage of a device, improves the efficiency of the device and prolongs the service life of the device.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention. In the figure, 1 is a transparent substrate layer, and 2 is a first electrode layer, i.e. an anode layer; 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is an electron transport layer, 8 is an electron injection layer, and 9 is a second electrode layer, i.e., a cathode layer.
Detailed Description
The technical solution of the present invention will be described in detail with reference to the embodiments below.
In one embodiment of the present application, there is provided an organic compound having a triazine structure, characterized in that the structure of the compound is represented by general formula (1):
in the general formula (1), Ar1～Ar3Is represented as C6-C30The aryl group of (a), preferably represented by one of phenyl, biphenyl, naphthyl, phenanthryl or anthracyl, may be the same or different;
r is independently hydrogen or C6-C30Preferably represents hydrogen or phenyl;
x represents O or S;
n represents 0 or 1.
In the triazine structure-containing compound provided herein, the compound may also be represented by a structure represented by general formula (2) or general formula (3):
in the general formulae (2) and (3), Ar1～Ar3Is represented as C6-C30The aryl group of (a), preferably represented by one of phenyl, biphenyl, naphthyl, phenanthryl or anthracyl, may be the same or different;
r is independently hydrogen or C6-C30Preferably represents hydrogen or phenyl;
x represents O or S.
In the triazine structure-containing compound provided herein, the compound may also be represented by any one of structures represented by general formulae (4) to (11):
ar in general formula (4) to general formula (11)1～Ar3Is represented as C6-C30Aryl of (2), preferablyIs represented by one of phenyl, biphenyl, naphthyl, phenanthryl or anthryl, which may be the same or different.
In another embodiment of the present application, the triazine structure-containing compound of the present invention may be represented by any one of general formulae (12) to (25);
ar in general formula (12) to general formula (25)1～Ar3Is represented as C6-C30The aryl groups of (a) preferably represent one of phenyl, biphenyl, naphthyl, phenanthryl or anthracyl groups, which may be the same or different.
In a specific embodiment of the present application, the present invention provides organic compounds containing a triazine structure, any one or more of the following compounds:
in this application, unless otherwise indicated, HOMO means the highest occupied orbital of a molecule and LUMO means the lowest unoccupied orbital of a molecule. Further, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between the energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level is, the lower the energy of the energy level is.
Any numerical range recited herein is intended to include all sub-ranges subsumed within the range with the same numerical precision. For example, "1.0 to 10.0" is intended to include all sub-ranges between (and including 1.0 and 10.0) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, all sub-ranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0. Any maximum numerical limitation recited herein is intended to include all smaller numerical limitations subsumed therein, and any minimum numerical limitation recited herein is intended to include all larger numerical limitations subsumed therein. Accordingly, applicants reserve the right to modify the specification, including the claims, to specifically describe any sub-ranges that fall within the ranges specifically described herein.
In the drawings, the size of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like reference numerals refer to like elements throughout.
In the present application, when describing electrodes and organic electroluminescent devices, and other structures, terms such as "upper" and "lower" used to indicate orientation only in a certain specific state do not mean that the related structures can exist only in the above-described orientation; conversely, if the structure is repositioned, e.g., inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "lower" side of the electrode means the side of the electrode closer to the substrate during the manufacturing process, and the opposite side away from the substrate is the "upper" side.
As used herein C6-30Aryl refers to a monovalent group comprising a carbocyclic aromatic system having from 6 to 30 carbon atoms as ring-forming atoms. C6-30Non-limiting examples of aryl groups can include phenyl, biphenyl, phenanthryl, anthracyl, terphenyl, naphthyl, and the like.
Process for the preparation of compounds
The compound according to the present invention is generally obtained by subjecting a raw material a (arylboronic acid ester) and a raw material B (aryl halide) to a SUZUKI coupling reaction in a solvent (e.g., DMF) in the presence of a catalyst such as palladium acetate under an alkaline environment such as potassium phosphate, and purifying the product to obtain the compound of the present invention with a purity of 99% or more.
Organic electroluminescent device
In another embodiment of the present application, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and a plurality of organic thin film layers between the first electrode and the second electrode, wherein at least one organic thin film layer contains the organic compound having a triazine structure.
In a preferred embodiment of the present application, the organic thin film layer comprises an electron transport layer, wherein the electron transport layer comprises an organic compound comprising a triazine structure according to the present invention. Preferably, the electron transport layer comprises, in addition to the organic compound of the invention, other electron transport materials, such as Liq (see examples for specific chemical structures).
In a preferred embodiment of the present application, the organic thin film layer comprises a light-emitting layer, wherein a host material of the light-emitting layer comprises the organic compound containing a triazine structure according to the present invention. Preferably, the light-emitting layer host material contains, in addition to the organic compound of the present invention, other light-emitting layer host materials, such as H1, H2 (see examples for specific chemical structures), and the like.
In a preferred embodiment of the present invention, the organic electroluminescent device according to the present invention comprises a substrate, a first electrode layer, an organic thin film layer, a second electrode layer, wherein the organic thin film layer includes, but is not limited to, a light emitting layer and a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron blocking layer and/or an electron injection layer.
The preferred device structure of the present invention is in the form of top emitting light (top emitting). Preferably, the anode of the organic electroluminescent device of the present invention employs an electrode having a high reflectivity, preferably ITO/Ag/ITO; the cathode adopts a transparent electrode, preferably a mixed electrode of Mg: Ag ═ 1:9, so that a microcavity resonance effect is formed, and the light emission of the device is emitted from the side of the Mg: Ag electrode.
In a preferred embodiment of the present invention, there is provided an organic electroluminescent device comprising a substrate, an anode, a cathode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode layer, wherein the anode is on the substrate, the hole injection layer is on the anode, the hole transport layer is on the hole injection layer, the electron blocking layer is on the hole transport layer, the light emitting layer is on the hole transport layer, the electron transport layer is on the light emitting layer, the electron injection layer is on the electron transport layer and the cathode layer is on the electron injection layer.
Hereinafter, the structure of an organic electroluminescent device according to one embodiment of the present application will be described in detail with reference to fig. 1.
As shown in fig. 1, according to one embodiment of the present application, the present invention provides an organic electroluminescent device, which comprises a substrate 1, a first electrode layer, and a second electrode layer; 2. a hole injection layer; 3. a hole transport layer; 4. an electron blocking layer; 5. a light emitting layer; 6. an electron transport layer; 7. an electron injection layer; 8. a second electrode layer.
As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples are transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; flexible PI film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use varies depending on the nature of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
A first electrode is formed on the substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode or a cathode. The anode material is preferably a material having a high work function so that holes are easily injected into the organic functional material layer. Non-limiting examples of the anode material include, but are not limited to, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin oxide (SnO)2) Zinc oxide (ZnO), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The first electrode may have a single layer structure or a multi-layer structure including two or more layers. For example, the anode may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. In addition, the thickness of the anode depends on the material used, and is generally 50 to 500nm, preferably 70 to 300nm and more preferably 100 to 200 nm.
The hole injection layer 3, the hole transport layer 4, and the electron blocking layer 5 may be disposed between the first electrode 2 and the light emitting layer 6.
The hole injection layer structure is such that a hole injection layer material, which may be, for example, a P dopant, is uniformly or non-uniformly dispersed in the hole transport layer. The P dopant may be selected from at least one compound selected from the group consisting of: quinone derivatives, such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; or cyano-containing compounds, such as compounds P1, NDP and F4-TCNQ shown below:
according to the invention, P1 is preferably used as the P dopant. The ratio of the hole transport layer to the P dopant used in the present invention is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the hole injection layer of the present invention may be 1 to 100nm, preferably 2 to 50nm and more preferably 5 to 20 nm.
The material of the hole transport layer is preferably a material having a high hole mobility, which enables holes to be transferred from the anode or the hole injection layer to the light-emitting layer. The hole transporting material may be a phthalocyanine derivative, a triazole derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative, an oxadiazole derivative, a hydrazone derivative, a stilbene derivative, a pyridoline derivative, a polysilane derivative, an imidazole derivative, a phenylenediamine derivative, an amino-substituted quinone derivative, a styrene compound such as a styrylanthracene derivative or a styrylamine derivative, a fluorene derivative, a spirofluorene derivative, a silazane derivative, an aniline copolymer, a porphyrin compound, a carbazole derivative, a polyarylalkane derivative, a polyphenyleneethylene derivative or a derivative thereof, a polythiophene or a derivative thereof, a poly-N-vinylcarbazole derivative, a conductive polymer oligomer such as a thiophene oligomer, an aromatic tertiary amine compound, a styrene amine compound, a triamine, a tetraamine, a benzidine, a propynenediamine derivative, a propynediamine derivative, a substituted aromatic amine, a substituted aniline derivative, an imidazole derivative, a derivative, or a derivative thereof, a styrene compound, a derivative, or a derivative, P-phenylenediamine derivatives, m-phenylenediamine derivatives, 1 '-bis (4-diarylaminophenyl) cyclohexane, 4,4' -bis (diarylamine) biphenyls, bis [4- (diarylamino) phenyl ] methanes, 4,4 '-bis (diarylamino) terphenyls, 4,4' -bis (diarylamino) quaterphenyls, 4,4 '-bis (diarylamino) diphenyl ethers, 4,4' -bis (diarylamino) diphenylsulfanes, bis [4- (diarylamino) phenyl ] dimethylmethanes, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes, or 2, 2-diphenylethylene compounds, and the like.
The thickness of the hole transport layer of the present invention may be 5 to 200nm, preferably 10 to 180nm and more preferably 20 to 150 nm.
The triplet state (T1) energy level of the material required by the electron blocking layer is higher than the T1 energy level of the host material in the light-emitting layer, and the electron blocking layer can play a role in blocking energy loss of the material of the light-emitting layer; the HOMO energy level of the material of the electron blocking layer is between the HOMO energy level of the material of the hole transport layer and the HOMO energy level of the material of the main body of the light-emitting layer, which is beneficial for injecting holes into the light-emitting layer from the positive electrode, and meanwhile, the material of the electron blocking layer is required to have high hole mobility, which is beneficial to hole transport and reduces the application power of the device; the LUMO level of the electron blocking layer material is higher than that of the light emitting layer host material, and plays a role of electron blocking, that is, the electron blocking layer material is required to have a wide forbidden band width (Eg). The electron blocking layer material satisfying the above conditions may be a triarylamine derivative, a fluorene derivative, a spirofluorene derivative, a dibenzofuran derivative, a carbazole derivative, or the like. Among them, triarylamine derivatives such as N4, N4-bis ([1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1, 1': 4',1 "-terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4' -diamine; spirofluorene derivatives, such as N- ([1,1 '-diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9' -spirobifluoren-2-amine; dibenzofuran derivatives such as N, N-bis ([1,1' -biphenyl ] -4-yl) -3' - (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, but not limited thereto.
According to the invention, the electron blocking layer may have a thickness of 1 to 200nm, preferably 5 to 150nm and more preferably 10 to 100 nm.
According to the present invention, the light emitting layer is located between the first electrode and the second electrode. The material of the light emitting layer is a material that can emit visible light by receiving holes from the hole transport region and electrons from the electron transport region, respectively, and combining the received holes and electrons. The light emitting layer may include a host material and a dopant material. As a host material and a guest material of the light-emitting layer of the organic electroluminescent device, the host material can be one or two of anthracene derivatives, quinoxaline derivatives, triazine derivatives, xanthone derivatives, diphenyl ketone derivatives, carbazole derivatives, pyridine derivatives or pyrimidine derivatives. The guest material can be pyrene derivatives, boron derivatives, chrysene derivatives, spirofluorene derivatives, iridium complexes or platinum complexes.
Preferably, the light emitting layer includes the organic compound having a triazine structure of the present invention as a light emitting layer host material. In a particularly preferred embodiment, the light-emitting layer consists of the organic compounds having a triazine structure of the invention and further light-emitting layer host materials (for example H1, see examples for specific chemical structures) and dopant materials (for example GD-1, see examples for specific chemical structures).
According to the present invention, in the light-emitting layer host material, the ratio of the organic compound of the present invention and the other light-emitting layer host material is 1:9 to 9:1, preferably 2:8 to 8:2, more preferably 4:6 to 6:4, and most preferably 5: 5.
According to the present invention, the ratio of the host material to the guest material is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the light-emitting layer of the present invention may be 5 to 60nm, preferably 10 to 50nm, more preferably 20 to 45 nm.
The hole blocking layer may be disposed over the light emitting layer. The triplet state (T1) energy level of the hole barrier layer material is higher than the T1 energy level of the luminescent layer host material, and the hole barrier layer material can play a role in blocking energy loss of the luminescent layer material; the HOMO energy level of the material is lower than that of the host material of the light-emitting layer, so that the hole blocking effect is achieved, and meanwhile, the material of the hole blocking layer is required to have high electron mobility, so that the electron transmission is facilitated, and the application power of the device is reduced; the hole-blocking layer material satisfying the above conditions may be a triazine derivative, an azabenzene derivative, or the like. Among them, triazine derivatives are preferable; but is not limited thereto.
The thickness of the light-emitting layer of the present invention may be 5 to 60nm, preferably 5 to 30nm, and more preferably 5 to 20 nm.
An electron transport layer may be disposed over the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. The electron transport layer comprises or consists of one or more triazine-containing organic compounds according to the invention. Preferably, the electron transport layer consists of the organic compound of the present invention and other electron transport layer materials. More preferably, the other electron transport layer material is an electron transport material commonly used in the art. Most preferably, the electron transport layer is composed of the organic compound of the present invention and Liq.
In the electron transport layer of the organic electroluminescent device according to the invention, the ratio of the organic compound according to the invention to the other electron transport layer material is 1:9 to 9:1, preferably 2:8 to 8:2, more preferably 4:6 to 6:4, most preferably 5: 5.
As the electron transport compound of the present invention, one or more of the compounds 1 to 19, 21, 24, 26, 29, 31, 34, 37, 39, 44, 47, 49, 55, 57, 70, 78, 83, 86, 91, 94, 99, 101, 105, 107, 110 are preferably used.
The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45 nm.
In a preferred embodiment of the present invention, the electron injection layer material is preferably a metal Yb having a low work function, so that electrons are easily injected into the organic functional material layer. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5 nm.
In one embodiment of the present invention, the second electrode may be a cathode or an anode, as previously described. In the present invention, the second electrode is preferably used as a cathode. The material used to form the cathode may be a material having a low work function, such as a metal, an alloy, a conductive compound, or a mixture thereof. Non-limiting examples of cathode materials may include lithium (Li), ytterbium (Yb), magnesium (Mg), aluminum (Al), calcium (Ca), and aluminum-lithium (Al-Li), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The thickness of the cathode depends on the material used and is generally in the range 5-100nm, preferably 7-50nm and more preferably 10-25 nm.
In a preferred embodiment of the organic electroluminescent device of the present invention, a light extraction layer (i.e. a capping layer or CPL layer) may be further added on the second electrode (i.e. cathode) of the device in order to improve the light extraction efficiency of the organic electroluminescent device. According to the principle of optical absorption and refraction, the CPL cover layer material should have a higher refractive index as well as a better refractive index, and the absorption coefficient should be smaller as well. Any material known in the art may be used as the CPL layer material, such as Alq3. The CPL capping layer is typically 5-300nm, preferably 20-100nm and more preferably 40-80nm thick.
Optionally, the organic electroluminescent device may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layers of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
Preparation method of organic electroluminescent device
The present invention also relates to a method of manufacturing the above organic electroluminescent device, which comprises sequentially laminating a first electrode, a plurality of organic thin film layers, and a second electrode on a substrate. The multilayer organic thin film layer is formed by sequentially laminating a hole transport region, a light emitting layer and an electron transport region from bottom to top on the first electrode, wherein the hole transport region is formed by sequentially laminating a hole injection layer, a hole transport layer and an electron blocking layer from bottom to top on the first electrode, and the electron transport region is formed by sequentially laminating a hole blocking layer, an electron transport layer and an electron injection layer from bottom to top on the light emitting layer. In addition, it is preferable to laminate a CPL layer on the second electrode to improve the light extraction efficiency of the organic electroluminescent device.
As for the lamination, a method of vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, LITI, or the like may be used, but is not limited thereto. Vacuum evaporation, among others, means heating and plating a material onto a substrate in a vacuum environment.
In the present invention, it is preferable to form the respective layers using a vacuum evaporation method, in which the respective layers may be formed at a temperature of about 100-500 ℃ and at a temperature of about 10 DEG C-8-10-2Vacuum degree of tray and its combination
Vacuum evaporation at a rate of (2). Preferably, the temperature is 200-. The degree of vacuum is preferably 10-6-10-2Torr, more preferably 10-5-10-3And (5) Torr. The rate is about
More preferably about
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, may be used as a single layer by forming a film in admixture with another material, or may be used as a laminated structure of layers formed alone, layers formed in admixture with each other, or a laminated structure of layers formed alone and layers formed in admixture with each other.
Display device
The invention also relates to a display device, in particular a flat panel display device, comprising the organic electroluminescent device. In a preferred embodiment, the display device may include one or more of the above-described organic electroluminescent devices, and in the case of including a plurality of the devices, the devices are stacked in combination in a lateral or longitudinal direction. The display device may further include at least one thin film transistor. The thin film transistor may include a gate electrode, source and drain electrodes, a gate insulating layer, and an active layer, wherein one of the source and drain electrodes may be electrically connected to a first electrode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, but is not limited thereto.
Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used in a generic and descriptive sense only and not for purposes of limitation. In some instances, features, characteristics and/or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics and/or elements described in connection with other embodiments, unless specifically indicated otherwise, as will be apparent to one of ordinary skill in the art upon submission of the present application. Accordingly, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
Examples
I. Examples of preparation of Compounds
The present invention will be described in detail with reference to the accompanying drawings and examples.
All of the raw materials and reactants in the following examples were purchased from energy saving, Inc.
Example 1: synthesis of Compound 1:
introducing nitrogen into a three-neck flask, adding 0.022mol of intermediate A-1, 100ml of DMF, 0.02mol of intermediate B-1 and 0.0002mol of palladium acetate, stirring, and adding 0.03mol of K3PO4The aqueous solution was heated to reflux for 12 hours, and the reaction was completed by sampling the sample. And naturally cooling, pouring the reaction solution into a 500ml beaker, adding 200ml of distilled water, mechanically stirring for 10min, then carrying out suction filtration on the mixed solution, leaching the filter cake for 1 time by using 100ml of distilled water, and then leaching by using 100ml of ethanol to obtain light yellow solid powder. Finally, the pale yellow solid powder was purified with dichloromethane: purifying the eluent with petroleum ether at a ratio of 1:3 by a silica gel column to obtain a compound 1, wherein the HPLC purity is 99.76 percent, and the yield is 63 percent; elemental analysis Structure (C)48H30N6O) theoretical value: c, 81.57; h, 4.28; n, 11.89; test values are: c, 81.72; h, 4.40; n, 11.70. MS (M/z) (M)+) Theoretical value is 706.25, found 706.19.
The procedure of example 1 was repeated to synthesize the following compounds; wherein the reaction conditions were similar except that intermediate I and intermediate II listed in table 1 below were used:
TABLE 1
The nmr hydrogen spectra data for the compounds prepared in the examples herein are shown in table 2:
TABLE 2
The organic compound of the present invention is used in a light-emitting device, and can be used as a host material or an electron-transporting material of a light-emitting layer. The HOMO level, the glass transition temperature Tg, the decomposition temperature Td, the S1 level, the T1 level, the evaporation temperature and the electron mobility of the compound of the present invention and the comparative compound were measured, respectively, and the results are shown in Table 3. Wherein the comparative compounds ET-1, ET-2, ET-3, ET-4, ET-5 have the following structures:
TABLE 3
Note 1: the triplet energy level T1 was measured by Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10-5mol/ml sh in toluene. The glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter from Chi-Di-Nash Co., Ltd.), with a heating rate of 10 ℃/min. The thermogravimetric temperature Td was a temperature at which 1% weight loss was observed in a nitrogen atmosphere, and was measured by a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate was 20 mL/min. The highest occupied molecular orbital HOMO energy level was tested by the ionization energy testing system (IPS3) in an atmospheric environment. The vapor deposition temperature was 10-4Pa, and the vapor deposition rate was 1A/S. The electron mobility was measured using time of flight (TOF) with a test apparatus, CMM-250 from japanese spectroscopy. S1 and T1 were tested using a Horiba (Fluorolog-3) fluorescence spectrometer, where the test environment for S1 was room temperature and the test environment for T1 was-77K. Eg, and LUMO ═ HOMO + Eg, were measured by a two-beam uv-vis spectrophotometer (model: TU-1901, beijing pros).
As can be seen from the data of Table 3, the HOMO energy level of the organic compound according to the present invention is about 6.0-7.0eV, preferably 6.2-6.9 eV; the LUMO energy level is about 3.0-4.0eV, preferably 3.2-3.6 eV; s1 is about 2.5-3.5eV, preferably 2.9-3.4 eV; tg of about 135-170 deg.C, preferably 140-165 deg.C; td is about 400 ℃ minus 470 ℃, preferably 410 ℃ minus 460 ℃; the evaporation temperature is about 320-340 ℃; electron mobility of about 5.0-7.0 × 10E-4cm2/Vs, preferably 5.1 to 6.6X 10E-4cm2/Vs。
It can also be seen from table 3 that compared to the comparative compound, the HOMO and LUMO energy levels, as well as the S1 energy level and the triplet energy level (T1 ≧ 2.4eV) of the present invention are comparable to the comparative compound, while Tg, Td are significantly higher than the comparative compound, but the evaporation temperature is significantly lower than the comparative compound, so that the thermal stability as well as the evaporation stability of the compound of the present invention are significantly better than the comparative compound. In addition, the electron mobility of the compound of the present invention is significantly higher than that of the comparative compound, which indicates that the compound of the present invention is more suitable for use in devices requiring electron transport, such as an electron transport material and a host material of a light emitting layer in an organic electroluminescent device.
In addition, the organic compound has more appropriate HOMO and LUMO energy levels and triplet state energy levels (T1 is more than or equal to 2.4eV), can be used as a main material of a light-emitting layer of an organic electroluminescent device or an electron transport material, has good carrier mobility, and can effectively reduce the driving voltage of the device. The glass transition temperature of the material is more than 130 ℃, which shows that the material has good film stability and inhibits the crystallization of the material. Compared with a comparison material, the material has higher glass transition temperature and decomposition temperature, so that the evaporation thermal stability of the material is improved, and the working stability of a device prepared from the material is improved. Finally, the material has lower evaporation temperature, and the difference between the evaporation temperature and the decomposition temperature is further increased, so that the evaporation stability of the material can be effectively improved, and the industrial window of evaporation of the material is improved.
Device preparation examples
The effects of the compounds synthesized according to the present invention as host materials for light emitting layers and electron transport materials in devices are explained in detail below by device examples 1 to 45 and device comparative examples 1 to 5. Device examples 2-45 and device comparative examples 1-5 compared with device example 1, the manufacturing process of the device was completely the same, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept the same, except that the host material or electron transport material of the light emitting layer in the device was changed. The device stack structure is shown in table 4, and the performance test results of each device are shown in table 5.
The molecular structural formula of the related material is shown as follows:
the structures of the comparative compounds ET-1, ET-2, ET-3, ET-4 and ET-5 are as described above. The above materials are all commercially available.
Device example 1
The preparation process comprises the following steps:
as shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, the anode is ITO (15nm)/Ag (150nm)/ITO (15nm), and the anode layer 2 is washed, i.e., sequentially washed with alkali, washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the anode layer. HT-1 and P-1 having a film thickness of 10nm were deposited on the anode layer 2 after the above washing as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to P-1 was 97: 3. HT-1 was then evaporated to a thickness of 138nm as hole transport layer 4. EB-1 was then evaporated to a thickness of 42nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, and the method comprises the following steps of H1: h2 was 1:1 (mass ratio of H1 and H2 was 1:1 as host material, GD-1 as dopant, doping ratio of dopant was 6% by weight, and thickness of light-emitting layer was 40 nm.) after the above light-emitting layer 6, vacuum evaporation of compounds 1 and Liq was continued, mass ratio of compounds 1 and Liq was 1:1, and thickness was 35nm, this layer was electron transport layer 7, on electron transport layer 7, a Yb layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this Yb layer was an electron injection layer 8, on the electron injection layer 8, the film thickness of Mg was 15 nm: and the mass ratio of Mg to Ag is 1:9, the Ag electrode layer is a cathode layer 9, and CPL-1 with the thickness of 80nm is evaporated on the basis of the cathode layer to be used as a light extraction layer 10.
Device examples 2-45 and device comparative examples 1-5 were prepared in a similar manner to device example 1, and the transparent PI films were used for both substrates, and ITO (15nm)/Ag (150nm)/ITO (15nm) was used for the anode, except that the parameters in table 4 below were used.
TABLE 4
Device test examples
The device prepared in II was tested for driving voltage, current efficiency, CIEx, CIEy, and LT95 lifetimes. Voltage, Current efficiency, CIEx, CIEy were tested using the IVL (Current-Voltage-Brightness) test System (Fushida scientific instruments, Suzhou) at a current density of 10mA/cm2. LT95 refers to the time taken for the luminance of the device to decay to 95% of the initial luminance, and the current density at the time of testing was 20mA/cm2(ii) a The life test system is an EAS-62C type OLED device life tester of Japan System research company.
The test results are shown in Table 5 below.
TABLE 5
From the results of the device test data in Table 5 above, it can be seen that the devices prepared using the compounds of the present invention as electron transport layer materials have significantly lower driving voltages, while at the same time the current efficiencies are significantly improved and the device lifetimes are substantially extended, e.g., by more than 1.5 times that of the comparative devices 1-5, as compared to the comparative devices using ET-1, ET-2, ET-3, ET-4 and ET-5 as electron transport layer materials.
Compared with the comparative device 1 prepared by using H1 and H2 as the light-emitting layer host materials, the device of the invention prepared by using H1 and the compound of the invention as the light-emitting layer host materials has the advantages of obviously reduced driving voltage, obviously improved current efficiency and greatly prolonged service life which is basically prolonged by more than 1.5 times.
The comparative compounds ET-1, ET-2, ET-3, ET-4 and ET-5 used in the comparative examples have structural formulas close to those of the present invention with only slight differences, such as only differences in the bonding position and the number of nitrogen atoms, however, unexpectedly, the compounds of the present invention achieve better technical effects as electron transport materials and light emitting layer materials than the comparative compounds.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. An organic compound having a triazine structure, wherein the structure of the compound is represented by general formula (1):
in the general formula (1), Ar1～Ar3Is represented as C6-C30Preferably one of phenyl, biphenyl, naphthyl, phenanthryl or anthracylMay be the same or different;
r is independently hydrogen or C6-C30Preferably represented by phenyl;
x represents O or S;
n represents 0 or 1.
2. The triazine structure-containing compound according to claim 1, which is represented by one of general formulae (12) to (25);
in general formulae (12) to (25), Ar1～Ar3Is represented as C6-C30The aryl groups of (a) preferably represent one of phenyl, biphenyl, naphthyl, phenanthryl or anthracyl groups, which may be the same or different.
3. The triazine structure-containing organic compound according to claim 1, wherein the specific structure of the organic compound is any one of the following structures:
4. an organic electroluminescent device comprising a first electrode, a second electrode and a plurality of organic thin film layers between the first electrode and the second electrode, wherein the organic thin film layers comprise a light-emitting layer and one or more of a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and the organic thin film layers preferably comprise an electron transport layer, characterized in that at least one of the organic thin film layers comprises one or more organic compounds according to any one of claims 1 to 3.
5. The organic electroluminescent device as claimed in claim 4, wherein the light-emitting layer comprises one or more organic compounds as claimed in any one of claims 1 to 3.
6. The organic electroluminescent device as claimed in claim 5, wherein the light-emitting layer further comprises other light-emitting layer materials.
7. The organic electroluminescent device as claimed in claim 4, wherein the electron transport layer comprises one or more organic compounds as claimed in any one of claims 1 to 3.
8. The organic electroluminescent device of claim 7, wherein the electron transport layer further comprises other electron transport materials, preferably further comprises a compound
9. Use of the organic compound containing a triazine structure according to any one of claims 1 to 3 as an electron transport layer material or a light-emitting layer host material in an organic electroluminescent device.
10. A display element comprising the organic electroluminescent device containing an organic compound of triazine structure as described in any one of claims 1 to 3.
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| CN109980112A (en) * | 2017-12-27 | 2019-07-05 | 三星Sdi株式会社 | Composition, organic optoelectronic device and display device |
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| CN109312230A (en) * | 2016-07-12 | 2019-02-05 | 三星Sdi株式会社 | Compound for organic photoelectric device, the constituent for organic photoelectric device and organic photoelectric device and display device |
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