CN114249715A - Organic compound containing xanthone and triazine structure and application thereof - Google Patents
Organic compound containing xanthone and triazine structure and application thereof Download PDFInfo
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 22
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 7
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 title claims description 12
- -1 xanthene ketone Chemical class 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000000463 material Substances 0.000 claims description 32
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 10
- 229910052722 tritium Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000002346 layers by function Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000001975 deuterium Chemical group 0.000 claims description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 125000005557 thiazolylene group Chemical group 0.000 claims 1
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 6
- 230000009477 glass transition Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000005281 excited state Effects 0.000 abstract description 2
- 238000005457 optimization Methods 0.000 abstract description 2
- 230000006798 recombination Effects 0.000 abstract description 2
- 238000005215 recombination Methods 0.000 abstract description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004065 semiconductor Substances 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 50
- 239000000543 intermediate Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002994 raw material Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000002390 rotary evaporation Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052760 oxygen 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
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102100037373 DNA-(apurinic or apyrimidinic site) endonuclease Human genes 0.000 description 1
- 101710109420 DNA-(apurinic or apyrimidinic site) endonuclease Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 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
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Abstract
The invention discloses an organic compound containing a structure of xanthene ketone and triazine, belonging to the technical field of semiconductors; the structure of the organic compound is shown as a general formula (1); the compound contains a structure of xanthone triazine, has higher glass transition temperature and molecular thermal stability, proper HOMO (highest occupied molecular orbital), LUMO (lowest unoccupied molecular orbital) energy level and T1 energy level, high chemical bond energy and excited state recombination energy and high carrier mobility, can effectively improve the efficiency of an OLED (organic light emitting diode) device through structural optimization of the device, can reduce the voltage of the OLED device, and can prolong the service life of the OLED device, especially the high-temperature service life of the OLED device.
Description
Technical Field
The invention belongs to the field of organic photoelectric materials, and relates to an organic compound containing a xanthone and triazine structure, application of the organic compound as an organic light-emitting functional material, and an organic electroluminescent device with a light-emitting layer containing the structural material.
Background
The Organic Light Emission Diodes (OLED) device 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 light-emitting device is of a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and the various different functional materials are mutually overlapped together according to the application to form the OLED light-emitting device. When voltage is applied to two end electrodes of the OLED light-emitting device as a current device, positive and negative charges in the organic layer functional material film layer are acted through an electric field, and the positive and negative charges are further compounded in the light-emitting layer, namely OLED electroluminescence is generated.
The development and the use of the light-emitting layer material of the OLED are carried out in three main stages, wherein the first stage mainly adopts a fluorescence light-emitting mechanism, the second stage mainly adopts a phosphorescence light-emitting mechanism, and the third stage adopts a TADF material as the light-emitting layer material, so that triplet excitons are effectively utilized, and the light-emitting efficiency of the device is improved. The TADF material is developed to the present, has abundant application in a luminescent layer, has controllable structure, stable property and low price, does not need precious metal, and has wide application prospect in the field of OLEDs.
In view of the actual demand of the current OLED display lighting industry, the development of TADF materials is far from sufficient, and a great deal of manpower and material resources are still required to be invested, so as to solve the problem that the efficiency and the service life development of the materials in the commercialization process are delayed.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides an organic compound containing a xanthone and triazine structure and application thereof. The compound contains a structure of xanthone triazine, has higher glass transition temperature and molecular thermal stability, proper HOMO (highest occupied molecular orbital), LUMO (lowest unoccupied molecular orbital) energy level and T1 energy level, high chemical bond energy and excited state recombination energy and high carrier mobility, can effectively improve the efficiency of an OLED (organic light emitting diode) device through structural optimization of the device, can reduce the voltage of the OLED device, and can prolong the service life of the OLED device, especially the high-temperature service life of the OLED device.
An organic compound containing a xanthone with triazine structure, wherein the structure of the organic compound is shown as a general formula (1)
Z is represented by C-R;
L1、L2each independently represents a single bond, substituted or unsubstituted C6-30Arylene of (a), substituted or unsubstituted C2-30One of the heteroaryl groups of (a);
ar is represented by C6-30Aryl of (C)2-30A heteroaryl group of the general formula (2) or the general formula (3):
x represents an oxygen atom, a sulfur atom, N-R1Or C (R)2)(R3)；
R is represented by hydrogen atom, halogen atom, deuterium atom, cyano, C, the same or different at each occurrence1-10Alkyl of (C)6-30Aryl of (C)2-30One of the heteroaryl groups of (a); two adjacent R on the same aromatic ring may also be bonded to substituted or unsubstituted C2-30Heteroaryl, substituted or unsubstituted C6-30Any one of the aryl groups of (a);
R1、R2、R3are each independently represented by C1-10Alkyl or C6-30Aryl of (a); r2、R3May also be joined to form a 4-, 5-or 6-membered ring;
the substituent for the substituent group is selected from deuterium, tritium, hydroxyl, cyano, amino, C1-10Alkyl, deuterium or tritium substituted C1-10Alkyl radical, C6-30Aryl, deuterium or tritium substituted C6-30Aryl of (C)2-30Heteroaryl, deuterium or tritium substituted C of2-30Any one of the heteroaryl groups of (a).
Preferred embodiment, L1、L2Each independently represents a single bond or a substitutionOr an unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted benzophenanthrylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenylcarbazolyl group, a substituted or unsubstituted dibenzofuranylene group; the substituent for the substituent group is any one selected from deuterium, tritium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, benzophenanthryl, pyridyl, pyrimidyl, quinolyl, imidazolyl, thiazolyl, furyl, benzimidazolyl, benzofuryl, benzothiazolyl, carbazolyl, phenylcarbazolyl and dibenzofuryl.
Preferably, the general formula (2) is specifically represented by any one of the following structures:
the general formula (3) is represented by any one of the following structures:
in a preferred embodiment, the structure of the compound is shown in any one of general formula (I-1) to general formula (I-4):
wherein L is1、L2Each independently represents a single bond, phenylene or biphenylene;
wherein Ar represents a hydrogen atom, a phenyl group, a biphenyl group, a naphthyl group, a structure represented by general formula (2) or general formula (3).
Preferably, the specific structure of the compound is any one of the following structures:
an organic electroluminescent device comprising an anode and a cathode, and an organic light-emitting functional layer therebetween, said organic light-emitting functional layer containing said organic compound.
Preferably, the host material of the organic light-emitting functional layer contains the organic compound.
Preferably, the guest material of the organic light-emitting functional layer contains the organic compound.
Compared with the prior art, the invention has the beneficial technical effects that:
the compound of the invention contains the combination of xanthone triazine, so that the molecule has proper LUMO energy level and the conjugated delocalization degree of the extension of the acceptor fragment, thereby not only having stronger electron transmission capability, but also effectively reducing the local aggregation of electrons in the process of transmitting electrons, enhancing the stability of the structure and further effectively prolonging the service life of the device. In addition, the carbazole in the structure is connected with the carbon and nitrogen of the acceptor structure, so that the material has certain hole bearing capacity. The material has certain hole bearing capacity on the basis of mainly transmitting electrons when being used as an electron type main body in a luminescent layer main body, and can effectively prolong the service life of a device.
The intramolecular chemical bonds of the compound have higher bond energy, can effectively inhibit the decomposition of molecules under the action of an electric field and illumination, and improve the stability of a device.
After the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a transparent substrate layer, 2 is 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 a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a covering layer.
Detailed Description
Definition of
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, C as used herein6-30Arylene refers to a divalent 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, terphenyl, naphthyl, and the like. C6-30Non-limiting examples of arylene groups can include phenylene, biphenylene, phenanthrylene, biphenylene, naphthylene, and the like. When C is present6-30Aryl radicalsAnd/or C6-30When the arylene group includes two or more rings, the rings may be fused to each other.
C as used herein2-30Heteroaryl group, C2-30Heteroarylene, heteroaryl having 5 to 30 ring atoms means a monovalent group including a carbocyclic aromatic system having at least one hetero atom selected from N, O, P and S as a ring atom and 2 to 30 carbon atoms. As used herein, a 5-3 membered heteroarylene refers to a divalent group comprising a carbocyclic aromatic system having as ring-forming atoms at least one heteroatom selected from N, O, P and S and 3 to 30 carbon atoms. Non-limiting examples of the 5-30 membered heteroaryl group may include pyridyl, dibenzofuranyl, benzoxazolyl, bisbenzoxazolyl, carbazolyl, N-phenylcarbazolyl, and the like. Non-limiting examples of the 5-30 membered heteroarylene group may include divalent groups of the above groups. When the 5-30 membered heteroaryl and 5-30 membered heteroarylene include two or more rings, these rings may be fused to each other.
As used herein C1-10Alkyl refers to a monovalent group comprising a straight or branched chain alkyl group having 1 to 10 carbon atoms. C1-10Non-limiting examples of alkyl groups may include methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl.
Synthesis example
The raw materials involved in the synthesis examples of the present invention were purchased from Zhongjieyanwang Limited.
EXAMPLE 1 Synthesis of Compound 1
Adding 0.01mol of intermediate 1 and 0.012mol of raw material 2-1 in a three-neck flask under the protection of nitrogen, adding 0.02mol of K after uniformly stirring in 150mL of toluene2CO3Adding 5 × 10 of water solution-5mol of Pd (PPh)3)4Heating to 120 deg.C for 24 hr, naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation to the filtrate (-0.09MPa, 85 deg.C), and passing through neutral silica gel column to obtain compoundObject 1. Elemental analysis Structure (molecular formula C)40H24N4O2): theoretical value C, 81.07; h, 4.08; n, 9.45; test values are: c, 81.08; h, 4.07; and N, 9.46. LC-MS: theoretical value is 592.19, found 592.75.1HNMR(400MHz,Chloroform-d)δ8.24(d,1H),8.02(s,2H),7.97(dd,1H),7.82–7.77(m,1H),7.74(ddd,1H),7.64(dd,2H),7.55(d,1H),7.52–7.41(m,5H),7.41–7.32(m,6H),7.19–7.12(m,3H),7.10–7.04(m,1H).
The synthesis of examples 2-19 was performed similarly to example 1, except that the intermediates and starting materials used were different. The intermediates, starting materials and test results used are shown in table 1 below.
TABLE 1
The nuclear magnetic properties of the synthesized materials in the tables of the synthesis examples are shown in table 2 below:
TABLE 2
The synthesis of the intermediate bodies referred to in table 1 was carried out as follows:
synthesis of intermediate 1
Adding 0.01mol of raw material 1-1, 0.012mol of raw material 1-2, 150m in a three-mouth bottle under the protection of nitrogenL toluene is stirred and mixed, and 0.02mol of K is added after the mixture is stirred evenly2CO3Adding 5 × 10 of water solution-5mol of Pd (PPh)3)4Heating to 120 ℃ for reaction for 24h, naturally cooling to room temperature after the reaction is finished, filtering, carrying out reduced pressure rotary evaporation on the filtrate (-0.09MPa, 85 ℃), and passing through a neutral silica gel column to obtain an intermediate 1.
Synthesis of intermediate 3
Adding 0.01mol of 3-1 of raw material, 0.012mol of 3-2 of raw material and 150mL of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, adding 0.03mol of sodium tert-butoxide and 5 multiplied by 10-5Heating the mol of palladium acetate to 120 ℃, and reacting for 24 hours; naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain a target product intermediate 3;
synthesis of intermediate 6
Adding 0.012mol of 6-1 of raw material, 0.012mol of 6-2 of raw material and 150mL of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, adding 0.02mol of potassium carbonate aqueous solution after stirring uniformly, and finally adding 5 multiplied by 10-5mol of Pd (PPh)3)4And heating to 120 ℃ for reaction for 24 hours. Naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain an intermediate 6-1;
adding 0.012mol of intermediate 6-1, 0.012mol of raw material 6-3 and 150mL of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, adding 0.02mol of potassium carbonate aqueous solution after stirring uniformly, and finally adding 5 multiplied by 10-5mol of Pd (PPh)3)4And heating to 120 ℃ for reaction for 24 hours. Naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtainIntermediate 6;
synthesis of intermediate 9
Adding 0.012mol of 9-1 of raw material, 0.012mol of 9-2 of raw material and 150mL of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, adding 0.02mol of potassium carbonate aqueous solution after stirring uniformly, and finally adding 5 multiplied by 10-5mol of Pd (PPh)3)4And heating to 120 ℃ for reaction for 24 hours. Naturally cooling to room temperature, filtering, and performing reduced pressure rotary evaporation on the filtrate (0.09 MPa, 85 ℃), and passing through a neutral silica gel column to obtain an intermediate 9-1;
adding 0.012 mole of intermediate 9-1, 0.01 mole of raw material 9-3, 150mL of toluene in a three-neck flask under the protection of nitrogen, stirring uniformly, adding 0.03 mole of cesium carbonate and 5X 10-5Heating the mol of palladium acetate to 120 ℃, reacting for 24 hours, naturally cooling to room temperature after the reaction is finished, filtering, carrying out reduced pressure rotary evaporation on the filtrate (-0.09MPa, 85 ℃), and passing through a neutral silica gel column to obtain a compound intermediate 9;
the synthesis steps of intermediates 2, 5 and 11 are similar to the synthesis method of intermediate 6, except that the raw materials used are different; the synthesis steps of intermediates 4, 10 are similar to the synthesis step of intermediate 3, except that the starting materials used are different. The synthesis steps for intermediates 7, 8 are similar to the synthesis step for intermediate 9, except that the starting materials used are different. The required starting materials for the specific synthesis of intermediates are shown in table 3 below.
TABLE 3
II basic Property test
The compound of the present invention is used in a light-emitting device, and can be used as a material for a light-emitting layer. The compounds prepared in the above examples of the present invention were tested for energy level, thermal stability and spectrum, and the test results are shown in table 4:
TABLE 4
| Compound (I) | HOMO | LUMO | Eg | T1 | Tg(℃) |
| 1 | 6.12 | 3.08 | 3.04 | 2.8 | 131.8 |
| 5 | 6.13 | 3.16 | 2.97 | 2.73 | 133.1 |
| 20 | 6.05 | 3.01 | 3.04 | 2.79 | 136.1 |
| 46 | 6.21 | 3.1 | 3.11 | 2.96 | 141.3 |
| 49 | 6.12 | 3.14 | 2.98 | 2.85 | 142.7 |
| 57 | 6.05 | 2.98 | 3.07 | 2.82 | 138.6 |
| 72 | 6.07 | 3.17 | 2.9 | 2.74 | 134.4 |
| 86 | 6.04 | 2.96 | 3.08 | 2.79 | 133.3 |
| 91 | 6 | 3.11 | 2.89 | 2.84 | 136.1 |
| 101 | 6.06 | 3.04 | 3.02 | 2.71 | 143.2 |
| 110 | 6.01 | 3.19 | 2.82 | 2.99 | 137.3 |
| 122 | 6.18 | 3.19 | 2.99 | 2.98 | 144.9 |
| 137 | 6.04 | 2.91 | 3.13 | 2.86 | 130.9 |
| 139 | 6.09 | 2.93 | 3.16 | 2.88 | 146.8 |
| REF-1 | 6.18 | 2.87 | 3.31 | 2.76 | 150 |
| REF-2 | 6.23 | 2.95 | 3.28 | 2.75 | 139.2 |
| REF-3 | 6.15 | 2.99 | 3.16 | 2.77 | 141.2 |
| REF-4 | 6.18 | 3.06 | 3.12 | 2.79 | 136.5 |
Note: the triplet energy level T1 was measured by Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10-5A toluene solution of mol/L; highest occupied scoreThe sub-orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is in an atmospheric environment; eg is tested by a double-beam ultraviolet-visible spectrophotometer (model: TU-1901); the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi-resistant company) at a temperature rise rate of 10 ℃/min.
As can be seen from the data in the above table, the organic compound of the present invention has a suitable energy level and a suitable triplet energy, and can be applied to the light emitting layer of the OLED device as a host.
III device preparation examples
The application effect of the synthesized OLED material of the present invention in the device is detailed by device examples 1-28 and device comparative examples 1-8. Compared with the device example 1, the device examples 2 to 28 and the device comparative examples 1 to 8 of the invention have the same manufacturing process, adopt the same substrate material and electrode material, and keep the film thickness of the electrode material consistent, except that the luminescent layer material in the device is replaced.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, washed with a detergent (SemiClean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 were deposited by a vacuum deposition apparatus as the hole injection layer 3, and the film thickness was 10nm, and the mass ratio of HT-1 to P-1 was 97: 3. HT-1 was then evaporated as a hole transport layer 4 to a thickness of 130 nm. EB-1 was subsequently evaporated as an electron blocking layer 5 with a thickness of 40 nm. After the evaporation of the electron barrier layer material is finished, the light-emitting layer 6 of the OLED light-emitting device is manufactured, and the structure of the light-emitting layer 6 comprises that the compound 1 used by the OLED light-emitting layer 6 is used as a main body material, GD-1 is used as a doping material, the doping proportion of the doping material is 6% (mass ratio), and the thickness of the light-emitting layer is 40 nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 35nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a Yb layer having a film thickness of 1nm was formed by a vacuum deposition apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce a 15 nm-thick Mg: the Ag electrode layer is used as a cathode layer 10, and the mass ratio of Mg to Ag is 1: 9. On the cathode layer 10, CP-1 was vacuum-deposited as the CPL layer 11, and the thickness was 70 nm.
The organic electroluminescent device 1 is obtained.
After the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the voltage, current efficiency, light emission spectrum, and lifetime of the device were measured. Device examples 1-26 and comparative examples 1-8 prepared in the same manner are shown in Table 5; the obtained device has a current of 10mA/cm2Voltage at, current efficiency, color and 20mA/cm2The results of the following tests for life LT95 are shown in Table 5.
TABLE 5
Note: the voltage, current efficiency and color coordinates were measured at a current density of 10mA/cm2Tested under conditions using an IVL (current-voltage-brightness) test system (frastd scientific instruments ltd, su); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to a linear vibration at 20mA/cm2The time it takes for the device luminance to decay to 95%.
As can be seen from the device data results in table 5, the organic light emitting device of the present invention has a greater improvement in device efficiency and device lifetime compared to the OLED devices of known materials, as compared to comparative devices 1-8. At the same time, the voltage of the organic light emitting device of the present invention is reduced compared to OLED devices of known materials.
Furthermore, the OLED device prepared by the invention has stable service life when working at high temperature and longer service life at high temperature; device examples 15-28 and comparative examples 5-8 were subjected to a lifetime test at 85 ℃ and compared with an ambient lifetime, and the results are shown in table 6.
TABLE 6
| Numbering | Life LT95(Hr)/25 deg.C | Life LT95(Hr)/80 deg.C | High rate of life at high temperature |
| Device example 15 | 231.4 | 72.3 | 3.2 |
| Device example 16 | 203.9 | 88.7 | 2.3 |
| Device example 17 | 231.8 | 100.8 | 2.3 |
| Device example 18 | 209.6 | 65.5 | 3.2 |
| Device example 19 | 224.5 | 77.4 | 2.9 |
| Device example 20 | 203.8 | 65.7 | 3.1 |
| Device example 21 | 213.4 | 68.8 | 3.1 |
| Device example 22 | 207.3 | 98.7 | 2.1 |
| Device example 23 | 223.2 | 74.4 | 3 |
| Device example 24 | 237 | 112.9 | 2.1 |
| Device example 25 | 225 | 80.4 | 2.8 |
| Device embodiments26 | 210.7 | 78.0 | 2.7 |
| Device example 27 | 217.8 | 62.2 | 3.5 |
| Device example 28 | 222.5 | 67.4 | 3.3 |
| Device comparative example 5 | 102.2 | 15.7 | 6.5 |
| Device comparative example 6 | 139.9 | 26.9 | 5.2 |
| Device comparative example 7 | 100.3 | 17.6 | 5.7 |
| Device comparative example 8 | 117.2 | 23.0 | 5.1 |
Note: high temperature life in Table 6 aboveThe life ratio refers to the ratio of the device life at 25 ℃ to the device life at 80 ℃; the service life of the device is controlled at the current density of 20mA/cm2Under the conditions of (1).
As shown in table 6 above, it can be found that the device using the material of the present application as the electronic host has a longer device lifetime and a significantly smaller high temperature lifetime rate than the comparative example at a higher temperature, indicating that the device using the material of the present application has better high temperature stability.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. An organic compound containing a xanthone with triazine structure is characterized in that the structure of the organic compound is shown as a general formula (1)
Z is represented by C-R;
L1、L2each independently represents a single bond, substituted or unsubstituted C6-30Arylene of (a), substituted or unsubstituted C2-30One of the heteroaryl groups of (a);
ar is represented by C6-30Aryl of (C)2-30A heteroaryl group of the general formula (2) or the general formula (3):
x represents an oxygen atom, a sulfur atom, N-R1Or C (R)2)(R3)；
R is represented by hydrogen atom, halogen atom, deuterium atom, cyano, C, the same or different at each occurrence1-10Alkyl of (2)、C6-30Aryl of (C)2-30One of the heteroaryl groups of (a); two adjacent R on the same aromatic ring may also be bonded to substituted or unsubstituted C2-30Heteroaryl, substituted or unsubstituted C6-30Any one of the aryl groups of (a);
R1、R2、R3are each independently represented by C1-10Alkyl or C6-30Aryl of (a); r2、R3May also be joined to form a 4-, 5-or 6-membered ring;
the substituent for the substituent group is selected from deuterium, tritium, hydroxyl, cyano, amino, C1-10Alkyl, deuterium or tritium substituted C1-10Alkyl radical, C6-30Aryl, deuterium or tritium substituted C6-30Aryl of (C)2-30Heteroaryl, deuterium or tritium substituted C of2-30Any one of the heteroaryl groups of (a).
2. The organic compound of claim 1, wherein L is1、L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted benzophenanthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted thiazolylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenylcarbazolyl group, a substituted or unsubstituted dibenzofuranylene group; the substituent for the substituent group is selected from deuterium, tritium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, benzophenanthryl, pyridyl, pyrimidyl, quinolyl, imidazolyl, thiazoleAny one of a furyl group, a benzimidazolyl group, a benzofuryl group, a benzothiazolyl group, a carbazolyl group, a phenylcarbazolyl group and a dibenzofuryl group.
3. The organic compound according to claim 1, wherein the general formula (2) is specifically represented by any one of the following structures:
the general formula (3) is represented by any one of the following structures:
4. the organic compound according to claim 1, wherein the structure of the compound is represented by any one of general formula (I-1) to general formula (I-4):
wherein L is1、L2Each independently represents a single bond, phenylene or biphenylene;
wherein Ar represents a hydrogen atom, a phenyl group, a biphenyl group, a naphthyl group, a structure represented by general formula (2) or general formula (3).
5. The organic compound according to claim 1, wherein the specific structure of the compound is any one of the following structures:
6. an organic electroluminescent device comprising an anode and a cathode, and an organic luminescent functional layer therebetween, wherein the organic luminescent functional layer contains the organic compound according to any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the host material of the organic light-emitting functional layer contains the organic compound according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 6, wherein the guest material of the organic light-emitting functional layer contains the organic compound according to any one of claims 1 to 5.
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