CN115304575B - Organic compound and organic electroluminescent device - Google Patents

Organic compound and organic electroluminescent device Download PDF

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CN115304575B
CN115304575B CN202210937845.8A CN202210937845A CN115304575B CN 115304575 B CN115304575 B CN 115304575B CN 202210937845 A CN202210937845 A CN 202210937845A CN 115304575 B CN115304575 B CN 115304575B
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CN115304575A (en
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邓东阳
刘营
高威
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Wuhan Tianma Microelectronics Co Ltd
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Abstract

The invention provides an organic compound, which has a structure shown in a formula I. The compound takes the O hetero-macrocyclic structure as a central skeleton, fluoranthene is condensed with the O hetero-macrocyclic structure in a specific form, and can be used as a blue light doping material to be applied to an organic photoelectric device through the limitation of substituent groups, so that the driving voltage of the device can be reduced, the luminous efficiency and the service life of the device can be improved, and the compound can be well applied to the technical field of electroluminescence.

Description

Organic compound and organic electroluminescent device
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic compound and an organic electroluminescent device.
Background
As a new generation display technology, the organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminescence, wide viewing angle, quick response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption and the like, and is widely applied to industries of flat panel display, flexible display, solid-state lighting, vehicle-mounted display and the like.
Organic electroluminescent materials can be classified into two types, namely, electrofluorescence, which is a radiative decay transition of singlet excitons, and electrophosphorescence, which is light emitted from triplet excitons, which is a radiative decay to the ground state, according to a luminescence mechanism. According to the spin quantum statistical theory, the formation probability ratio of singlet excitons and triplet excitons is 1:3. The internal quantum efficiency of the fluorescent material is not more than 25%, and the external quantum efficiency is generally lower than 5%; the internal quantum efficiency of the electrophosphorescent material reaches 100% theoretically, and the external quantum efficiency can reach 20%. In 1998, the university of Jilin's horses in China and the university of Prlington's Forrest in U.S. reported the use of osmium complexes and platinum complexes as dyes doped into the light-emitting layer, respectively, were successful for the first time and explained the phosphorescent electroluminescence phenomenon, and the prepared phosphorescent materials were applied to electroluminescent devices at the beginning.
Since phosphorescent heavy metal materials have a long lifetime (μs) and can cause triplet-triplet annihilation and concentration quenching at high current densities, resulting in reduced device performance, heavy metal phosphorescent materials are typically doped into suitable host materials to form a host-guest doped system that optimizes energy transfer, maximizes luminous efficiency and lifetime.
The existing blue light doped material has the problems of insufficient service life, insufficient efficiency and higher driving voltage.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide an organic compound and an organic electroluminescent device, which can effectively improve the efficiency and lifetime of an OLED device and reduce the driving voltage thereof.
The invention provides an organic compound, which has a structure shown in a formula I:
wherein L is 1 、L 2 、L 3 、L 4 Independently selected from single bond, substituted or unsubstituted aryl;
R 1 、R 2 、R 3 、R 4 independently selected from substituted or unsubstituted aryl, heteroaryl, or arylamine groups;
n 1 、n 2 、n 3 、n 4 independently selected from 0, 1 or 2, and are not simultaneously 0.
The invention provides application of the organic compound as a blue light doping material.
The invention provides an organic light-emitting device, which comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one organic compound.
The invention provides a display panel comprising the organic light-emitting device.
Compared with the prior art, the invention provides an organic compound which has a structure shown in a formula I. The compound takes an O heterospiro-type macrocyclic structure as a central skeleton, fluoranthene is condensed with the O heteromacrocyclic structure in a specific form, and the compound has a structure of intersecting each other, and the structure has strong rigidity, large steric hindrance and difficult rotation; l (L) X -R X The introduction of the compound increases the asymmetry of molecules, can reduce the crystallinity and the planeness of the molecules, prevents the molecules from moving on the plane, and ensures that the three-dimensional structure of the compound is more stable; l (L) X -R X The introduction of the material can also improve the glass transition temperature of the material, passivate active C-H bonds and improve the stability of the material. By adjustingThe whole substituent group type can adjust the energy level of molecules, so that the molecule can be used as a blue light doping material to be applied to an organic photoelectric device, the driving voltage of a device can be reduced, the luminous efficiency and the service life of the device can be improved, and the molecule can be well applied to the technical field of electroluminescence.
Drawings
Fig. 1 is a schematic structural view of an organic light emitting device according to the present invention.
Detailed Description
The invention provides an organic compound, which has a structure shown in a formula I:
wherein L is 1 、L 2 、L 3 、L 4 Independently selected from single bond, substituted or unsubstituted aryl;
R 1 、R 2 、R 3 、R 4 independently selected from substituted or unsubstituted aryl, heteroaryl, or arylamine groups;
n 1 、n 2 、n 3 、n 4 independently selected from 0, 1 or 2, and are not simultaneously 0.
Optionally, the L 1 、L 2 、L 3 、L 4 Independently selected from single bond, phenyl, and groups formed by connecting or fusing 2 to 3 phenyl groups through single bond.
Optionally, the L 1 、L 2 、L 3 、L 4 Independently selected from single bond, phenyl, biphenyl, naphthyl or anthracenyl.
Optionally, the R 1 、R 2 、R 3 、R 4 Independently selected from the group consisting of substituted or unsubstituted phenyl, fused aromatic groups formed by 2 to 5 phenyl groups linked by single bonds or fused, monocyclic heteroaryl, fused ring heteroaryl formed by 2 to 5 phenyl groups fused with monocyclic heteroaryl, fluorenyl, spirofluorenyl, NR 5 R 6 ；
The heteroatoms in the monocyclic heteroaryl are selected from one or more of N, O, S, si;
the R is 5 、R 6 Independently selected from phenyl groups, groups formed by 2 to 3 phenyl groups through single bond connection or fusion.
Alternatively, the fused aromatic group is formed by 2, 3, 4 or 5 phenyl groups linked by single bonds or fused.
Alternatively, the fused ring heteroaryl is formed by 2, 3, 4 or 5 phenyl groups and a monocyclic heteroaryl group being fused.
Optionally, the R 5 、R 6 Independently selected from phenyl, biphenyl, naphthyl, anthryl, phenanthryl.
Optionally, the R 1 、R 2 、R 3 、R 4 Independently selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyranyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, benzophenanthryl, silafluorenyl, spirosilafluorenyl, benzofurocarbazolyl, benzofurophenyl, fluorenyl, spirofluorenyl, N-diphenylamino, N-dinaphthylamino, any of the structures represented by formulas a-c:
X 1 、X 2 、X 3 、X 4 independently selected from C, N, O, S or Si;
X 5 is N.
The R is 1 、R 2 、R 3 、R 4 May be attached to the corresponding L through any carbon or heteroatom thereof.
Optionally, the R 1 、R 2 、R 3 、R 4 Independently selected from any one of the following structures:
# denotes a connection position.
Optionally, the R 1 、R 2 、R 3 、R 4 Independently selected from one or more of deuterium, halogen, C1-C10 alkyl, halogen substituted C1-C10 alkyl, trimethylsilyl, five-membered or six-membered cycloalkyl, aryl, alkyl substituted aryl, halogen substituted aryl, heteroaryl, alkyl substituted heteroaryl, halogen substituted heteroaryl, arylamine.
Optionally, the R 1 、R 2 、R 3 、R 4 The substituent groups of (C) are independently selected from deuterium, F, cl, br, C-C6 alkyl, fluoro-C1-C6 alkyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, C1-C6 alkyl substituted phenyl, fluoro-phenyl, N-diphenylamino and N, N-dinaphthylamino.
Optionally, the R 1 、R 2 、R 3 、R 4 Independently selected from the group consisting of deuterium, F, cl, br, methyl, fluoromethyl, ethyl, fluoroethyl, N-propyl, isopropyl, N-butyl, isobutyl, t-butyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, methylphenyl, fluorophenyl, N-diphenylamino, N-dinaphthylamino.
Optionally, the n 1 、n 2 、n 3 、n 4 Any 1 to 3 of them are 1, and the rest are 0.
Optionally, the n 1 、n 2 、n 3 、n 4 Any 1, 2 or 3 of them are 1, and the rest are 0.
Optionally, the organic compound has any one of the following structures:
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the single bond in the above formula represents a methyl group.
The blue light doped material provided by the invention has good thermal stability and film forming property, and proper glass transition temperature Tg, is favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduces phase separation, and maintains the stability of a device. The device has higher carrier transmission rate and balanced carrier transmission performance, is favorable for balancing hole and electron transmission in the device, and simultaneously obtains a wider carrier composite region and improves the luminous efficiency.
Based on this, the present invention provides the use of the above-mentioned organic compound as a blue light doped material.
The invention provides an organic light-emitting device, which comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one organic compound.
The invention provides a display panel comprising the organic light-emitting device.
The organic light-emitting device provided by the invention can be an organic light-emitting device well known to a person skilled in the art, and optionally comprises a substrate, an ITO anode, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light-emitting layer, a first electron transport layer, a second electron transport layer, a cathode (magnesium-silver electrode, magnesium-silver mass ratio of 1:9) and a capping layer (CPL).
Alternatively, the anode material of the organic light-emitting device may be selected from metal-copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., and alloys thereof; such as metal oxide-indium oxide, zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; such as the conductive polymers polyaniline, polypyrrole, poly (3-methylthiophene), and the like, include materials known to be suitable as anodes in addition to facilitating hole injection materials and combinations thereof.
The cathode material of the organic light-emitting device can be selected from metal-aluminum, magnesium, silver, indium, tin, titanium and the like and alloys thereof; such as multi-layer metal material LiF/Al, liO 2 /Al、BaF 2 Al, etc.; materials that contribute to electron injection in addition to the aboveCombinations, also including materials known to be suitable as cathodes.
The organic optoelectronic device, such as an organic light emitting device, has at least one light emitting layer (EML), and may further include other functional layers including a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL).
According to the invention, the organic light-emitting device is prepared according to the following method:
an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer.
Alternatively, the organic thin layer may be formed by known film forming methods such as evaporation, sputtering, spin coating, dipping, ion plating, and the like.
The invention provides a display device which comprises the display panel.
In the present invention, an organic light emitting device (OLED device) may be used in a display apparatus, wherein the organic light emitting display apparatus may be a mobile phone display screen, a computer display screen, a television display screen, a smart watch display screen, a smart car display panel, a VR or AR helmet display screen, display screens of various smart devices, or the like.
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Intermediate preparation
The intermediate of the organic compound with the structure shown as H51, H52 and H56 can be prepared by the following synthetic route:
1) Intermediate products1, preparation: into a 1L three-necked flask, 0.20mol of reactant 1,0.21mol of reactant 2,0.40mol of potassium carbonate, 165.6g of water, 1.0mmol of Pd (PPh 3 ) 4 400mL of toluene, 100mL of absolute ethanol, N 2 Protecting, heating to reflux, preserving heat for 8 hours, stopping reaction, cooling to 25 ℃, separating liquid, collecting an organic phase, washing to be neutral, decompressing the organic phase to remove a solvent, purifying by adopting a pure toluene column chromatography, and recrystallizing toluene and absolute ethyl alcohol to obtain an intermediate 1.
2) Preparation of intermediate 2 in a 1L three-necked flask, 0.15mol of intermediate 1,0.375mol of sodium hydroxide, 400mL of absolute ethanol, N 2 Protecting, heating to reflux, reacting for 3 hours at a temperature of 25 ℃, dropwise adding 0.375mol of 10% diluted hydrochloric acid solution, stirring for 0.5 hours, extracting by ethyl acetate, passing an organic phase through a silica gel column, decompressing and removing a solvent to obtain a crude intermediate 2, and recrystallizing by toluene and absolute ethyl alcohol to obtain a fine intermediate 2.
3) Preparation of intermediate 3 in a 500mL three-necked flask, 0.10mol of intermediate 2, 240g of methanesulfonic acid, N 2 And (3) protecting, heating to 70-75 ℃, preserving heat, reacting for 6 hours, cooling to 25 ℃, slowly pouring the reaction solution into 250g of crushed ice, stirring, filtering, leaching with 50mL of water, obtaining a crude product intermediate 3, and recrystallizing toluene to obtain a fine product.
4) Preparation of intermediate 4: in a 500mL three-necked flask, 0.05mol of intermediate 3,0.50mol of phenol, 100g of methanesulfonic acid, N 2 And (3) protecting, heating to 140-145 ℃, carrying out heat preservation reaction for 15 hours, stirring and cooling to 25 ℃ after the reaction is finished, adding 100g of water and 100g of dichloromethane, stirring, separating liquid, washing with water, passing an organic phase through a silica gel column, removing a solvent under reduced pressure to obtain a crude product compound 4, and recrystallizing with ethyl acetate to obtain an intermediate 4.
Example 1
Synthesis of H51:
in a 500mL three-necked flask, 5mmol of intermediate 4-51,5mmol of reactant G51, 20mmol of potassium carbonate, 0.25mmol of Pd (PPh 3 ) 4 300mL of dichloroethane, N 2 And (3) protecting, carrying out heat preservation reaction for 6 hours at 75-80 ℃, stopping the reaction, cooling to 25 ℃, adding 150mL of deionized water, stirring and separating liquid, collecting an organic phase, and removing a solvent to obtain the H51 compound.
MALDI-TOF: m/z: calculated values: c (C) 53 H 32 O684.25, found: 684.63.
compound elemental analysis results: calculated values: c (C) 53 H 32 O (%) is C,92.95; h,4.71; o,2.34; test value: c,92.97; h,4.70; o,2.33.
Example 2
Synthesis of H52:
the synthesis of compound H52 is similar to that of H51, except that G51 in the reaction is replaced with an equimolar amount of G52.
MALDI-TOF: m/z: calculated values: c (C) 47 H 29 No. 623.22, found: 623.45.
compound elemental analysis results: calculated values: c (C) 47 H 29 NO (%) C,90.50; h,4.69; n,2.25; o,2.57; test value: c,90.49; h,4.68; n,2.26; o,2.57.
Example 3
Synthesis of H56:
the synthesis of compound H56 is similar to that of H51, except that intermediate 4-51, G51 in the reaction is replaced with equimolar amounts of intermediate 4-56, G56, respectively.
MALDI-TOF: m/z: calculated values: c (C) 53 H 31 No. 697.24, found: 697.47.
compound elemental analysis results: calculated values: c (C) 53 H 31 NO(％):C,91.22；H,4.48；N,2.01; o,2.29; test value: c,91.23; h,4.47; n,2.02; o,2.29.
Intermediate of the organic compounds with structures shown in the compounds H33, H65 and H105 can be prepared by the following synthetic routes:
1) Preparation of intermediate 1': into a 1L three-necked flask, 0.20mol of reactant 1,0.21mol of reactant 2',0.40mol of potassium carbonate, 165.6g of water, 1.0mmol of Pd (PPh 3 ) 4 400mL of toluene, 100mL of absolute ethanol, N 2 Protecting, heating to reflux, preserving heat for 8 hours, stopping reaction, cooling to 25 ℃, separating liquid, collecting an organic phase, washing to be neutral, decompressing the organic phase to remove a solvent, purifying by adopting a pure toluene column chromatography, and recrystallizing toluene and absolute ethyl alcohol to obtain an intermediate 1'.
2) Preparation of intermediate 2 'in a 1L three-necked flask, 0.15mol of intermediate 1',0.375mol of sodium hydroxide, 400mL of absolute ethanol, N 2 Protecting, heating to reflux, reacting for 3 hours at a temperature of 25 ℃, dropwise adding 0.375mol 10% diluted hydrochloric acid solution, stirring for 0.5 hours, extracting by ethyl acetate, passing an organic phase through a silica gel column, decompressing and removing a solvent to obtain a crude intermediate 2', recrystallizing by toluene and absolute ethyl alcohol to obtain a fine intermediate 2'.
3) Preparation of intermediate 3 'in a 500mL three-necked flask, 0.10mol of intermediate 2',240g of methanesulfonic acid, N 2 And (3) protecting, heating to 70-75 ℃, preserving heat, reacting for 6 hours, cooling to 25 ℃, slowly pouring the reaction solution into 250g of crushed ice, stirring, filtering, leaching with 50mL of water, obtaining a crude intermediate 3', and recrystallizing toluene to obtain a fine product.
4) Preparation of intermediate 4': in a 500mL three-necked flask, 0.05mol of intermediate 3',0.50mol of phenol, 100g of methanesulfonic acid, N 2 Protecting, heating to 140-145 ℃, reacting for 15 hours while maintaining the temperature, stirring and cooling to 25 ℃ after the reaction is finished, adding 100g of water and 100g of dichloromethane, stirring, separating liquid, washing with water, passing the organic phase through a silica gel column, and removing the solvent under reduced pressure to obtain crude productCompound 4 'was recrystallized from ethyl acetate to afford intermediate 4'.
Example 4
Synthesis of H33:
50mol of intermediate 4',300g of dichloroethane are added into a 500mL three-port bottle, the temperature is reduced to 0-5 ℃ by an ice-water bath, bromine is slowly added dropwise, the temperature is kept at 0-5 ℃ for reaction for 8 hours, sodium sulfite solution is added for quenching reaction, liquid separation and water washing are carried out, an organic phase passes through a silica gel column, the solvent is removed under reduced pressure, and toluene is recrystallized, thus obtaining intermediate 4' -1.
In a 500mL three-necked flask, 5mmol of intermediate 4' -1,5mmol of reactant G33, 20mmol of potassium carbonate, and 0.25mmol of Pd (PPh 3 ) 4 300mL of dichloroethane, N 2 And (3) protecting, carrying out heat preservation reaction for 6 hours at 75-80 ℃, stopping the reaction, cooling to 25 ℃, adding 150mL of deionized water, stirring and separating liquid, collecting an organic phase, and removing a solvent to obtain the H33 compound.
MALDI-TOF: m/z: calculated values: c (C) 45 H 32 O588.25, found: 588.49.
compound elemental analysis results: calculated values: c (C) 45 H 32 O (%) is C,91.80; h,5.48; o,2.72; test value: c,91.81; h,5.47; o,2.72.
Example 5
Synthesis of H65:
the synthesis of compound H65 was similar to that of H33, except that G33 in the reaction was replaced with an equimolar amount of G65.
MALDI-TOF: m/z: calculated values: c (C) 50 H 32 O648.25, found: 648.63.
compound elemental analysis results: calculated values: c (C) 50 H 32 O(％):C,92.56；H,4.97；O,2.47; test value: c,92.57; h,4.96; o,2.47.
Example 6
Synthesis of H105:
the synthesis of compound H105 was similar to that of H33, except that G33 in the reaction was replaced with an equimolar amount of G105.
MALDI-TOF: m/z: calculated values: c (C) 59 H 34 O758.26, found: 758.55.
compound elemental analysis results: calculated values: c (C) 59 H 34 O (%) is C,93.38; h,4.52; o,2.11; test value: c,93.36; h,4.53; o,2.11.
Example 7
Synthesis of H63:
1) In a 500mL three-necked flask, 5mmol of intermediate 4-51,5mmol of reactant G63, 20mmol of potassium carbonate, 0.25mmol of Pd (PPh 3 ) 4 300mL of dichloroethane, N 2 And (3) protecting, carrying out heat preservation reaction for 6 hours at 75-80 ℃, stopping the reaction, cooling to 25 ℃, adding 150mL of deionized water, stirring and separating liquid, collecting an organic phase, and removing a solvent to obtain the H63-1 compound.
2) 50mol of compound H63-1 and 300g of dichloroethane are added into a 500mL three-necked flask, the temperature is reduced to 0-5 ℃ by an ice-water bath, bromine is slowly added dropwise, the temperature is kept at 0-5 ℃ for reaction for 8 hours, sodium sulfite solution is added for quenching reaction, liquid separation and water washing are carried out, an organic phase passes through a silica gel column, the solvent is removed under reduced pressure, and toluene is recrystallized, thus obtaining an intermediate H63-2.
3) In a 500mL three-necked flask, 5mmol of intermediate H63-2, 10mmol of reactant G63-1, 20mmol of potassium carbonate, 0.25mmol of Pd (PPh 3 ) 4 300mL of dichloroethane, N 2 Protecting, reacting at 75-80 deg.c for 6 hr, stopping reaction and lowering reaction rateHeating to 25 ℃, adding 150mL of deionized water, stirring and separating liquid, collecting an organic phase, and removing a solvent to obtain the H63 compound.
MALDI-TOF: m/z: calculated values: c (C) 65 H 41 No. 851.32, found: 851.78.
compound elemental analysis results: calculated values: c (C) 65 H 41 NO (%) C,91.63; h,4.85; n,1.64; o,1.88; test value: c,91.63; h,4.85; n,1.64; o,1.88.
The organic compounds with structures shown as the compounds H120, H143 and H186 can be prepared by the following synthetic routes:
the synthesis of intermediate 4a is similar to that of intermediate 4, except that reactant 1 and reactant 2 in reaction 1) are replaced with equimolar amounts of reactant 1a and reactant 2a, respectively.
Example 8
Synthesis of H120:
in a 500mL three-necked flask, 5mmol of intermediate 4a,5mmol of reactant G120, 20mmol of potassium carbonate, 0.25mmol of Pd (PPh 3 ) 4 300mL of dichloroethane, N 2 And (3) protecting, carrying out heat preservation reaction for 6 hours at 75-80 ℃, stopping the reaction, cooling to 25 ℃, adding 150mL of deionized water, stirring and separating liquid, collecting an organic phase, and removing a solvent to obtain the H120 compound.
MALDI-TOF: m/z: calculated values: c (C) 61 H 36 N 2 O812.28, found: 812.63.
compound elemental analysis results: calculated values: c (C) 61 H 36 N 2 O (%) is C,90.12; h,4.46; n,3.45; o,1.97; test value: c,90.10; h,4.47; n,3.45; o,1.97.
Example 9
Synthesis of H143:
the synthesis of compound H143 is similar to that of H120, except that G120 in the reaction is replaced with an equimolar amount of G143.
MALDI-TOF: m/z: calculated values: c (C) 59 H 34 OSi 786.24, found: 786.24.
compound elemental analysis results: calculated values: c (C) 59 H 34 OSi (%) C,90.04; h,4.35; o,2.03; si,3.57; test value: c,90.06; h,4.34; o,2.03; si,3.57.
Example 10
Synthesis of H186
The synthesis of compound H186 is similar to that of H120, except that G120 in the reaction is replaced with an equimolar amount of G186.
MALDI-TOF: m/z: calculated values: c (C) 57 H 31 No. 745.24, found: 745.69.
compound elemental analysis results: calculated values: c (C) 57 H 31 NO (%) C,91.79; h,4.19; n,1.88; o,2.15; test value: c,91.77; h,4.19; n,1.88; o,2.15.
Device example 1
The present embodiment provides an organic light emitting device. As shown in fig. 1, the organic light emitting device includes: the substrate 1, the ITO anode 2, the first hole transport layer 3, the second hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the first electron transport layer 7, the second electron transport layer 8, the cathode 9 (magnesium silver electrode, magnesium silver mass ratio is 9:1) and the cap layer (CPL) 10, wherein the thickness of the ITO anode 2 is 15nm, the thickness of the first hole transport layer 3 is 10nm, the thickness of the second hole transport layer 4 is 95nm, the thickness of the electron blocking layer 5 is 30nm, the thickness of the light emitting layer 6 is 30nm, the thickness of the first electron transport layer 7 is 30nm, the thickness of the second electron transport layer 8 is 5nm, the thickness of the magnesium silver electrode 9 is 15nm and the thickness of the cap layer (CPL) 10 is 100nm.
The OLED device was prepared as follows:
1) Cutting the glass substrate 1 into 50mm×50mm×0.7mm sizes, respectively sonicating in isopropyl alcohol and deionized water for 30min, and then exposing to ozone for about 10 min for cleaning; mounting the obtained glass substrate with the ITO anode 2 onto a vacuum deposition apparatus;
2) Evaporating a hole buffer layer material compound a and a compound b on the ITO anode 2 by a vacuum evaporation mode, wherein the mass ratio of the compound a to the compound b is 2:98, so as to obtain a layer with the thickness of 10nm, and the layer is used as a first hole transport layer 3;
3) Vacuum evaporating a material compound b of the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with a thickness of 95nm as the second hole transport layer 4;
4) Evaporating a material compound c on the second hole transport layer 4 to obtain a layer with a thickness of 30nm, which serves as an electron blocking layer 5;
5) Co-depositing a light-emitting layer 6 on the electron blocking layer 5, wherein a compound d is used as a host material, an organic compound H51 provided in example 1 of the present invention is used as a doping material, the mass ratio of the organic compound d to H51 is 97:3, and the thickness is 30nm; the method comprises the steps of carrying out a first treatment on the surface of the
6) Vacuum evaporating a first electron transport layer 7 compound e on the light-emitting layer 6 to obtain a first electron transport layer 7 with a thickness of 30nm;
7) Vacuum evaporating material LiF of the second electron transport layer 8 on the first electron transport layer 7 to obtain a second electron transport layer 8 with a thickness of 5 nm;
8) Vacuum evaporating magnesium and silver on the second electron transport layer 8 to obtain a cathode 9 with the thickness of 15nm, wherein the mass ratio of Mg to Ag is 9:1;
9) The high refractive index hole-type material compound f was vacuum deposited on the cathode 9 to a thickness of 100nm, and used as a cathode coating layer (cap layer or CPL) 10.
The structural formulae of the material compounds a to f mentioned in the above steps are shown below, respectively:
device example 2
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H52 provided by the present invention; the other preparation steps were identical.
Device example 3
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H56 provided by the present invention; the other preparation steps were identical.
Device example 4
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H33 provided by the present invention; the other preparation steps were identical.
Device example 5
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H65 provided by the present invention; the other preparation steps were identical.
Device example 6
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H105 provided by the present invention; the other preparation steps were identical.
Device example 7
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H63 provided by the present invention; the other preparation steps were identical.
Device example 8
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H120 provided by the present invention; the other preparation steps were identical.
Device example 9
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H143 provided by the present invention; the other preparation steps were identical.
Device example 10
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H186 provided by the present invention; the other preparation steps were identical.
Device example 11
The present device example differs from device example 1 only in that the organic compound H51 in step (5) is replaced with an equivalent amount of the organic compound H176 provided by the present invention; the other preparation steps were identical.
Device comparative example 1
The device comparative example differs from device example 1 only in that the organic compound H51 in step (5) was treated with an equivalent amount of the comparative compound HAReplacement; the other preparation steps were identical.
Device comparative example 2
The device comparative example differs from device example 1 only in that the organic compound H51 in step (5) was treated with an equivalent amount of the comparative compound HBReplacement; the other preparation steps were identical.
Performance evaluation of OLED device:
testing the currents of the OLED device under different voltages by using a Keithley 2365A digital nano-volt meter, and dividing the currents by the light emitting areas to obtain the current densities of the OLED device under different voltages; testing the brightness and radiant energy density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; at different electrical levels according to OLED devicesCurrent density and brightness under pressure, giving a voltage of 10mA/cm at the same current density 2 ) Is the luminance 1Cd/m 2 A lower turn-on voltage; lifetime LT95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance 2 Under test conditions).
Von, CE, and LT95 of device examples 1 to 5 are ratios of the respective test data to the test data of comparative example, i.e., relative values compared to comparative example 1, based on 100% of the test data of the on-luminance voltage Von, current efficiency CE, and lifetime LT95 of device comparative example (REF); the specific data are shown in table 1.
TABLE 1
As can be seen from the data of table 1, the electroluminescent device using the organic compound of the present invention has a lower turn-on voltage, which is reduced by about 4%, compared with the device comparative example, thus reducing the power consumption of the device; the device using the organic compound has higher current efficiency, which is improved by about 4% compared with the comparative example; the device using the organic compound of the present invention has a longer lifetime, which is prolonged by about 5% compared to the device of the comparative example. This is probably because the compound of the present invention has a specific core structure, a more steric space structure, a larger HOMO-LUMO gap, a narrower half-width, and a higher color purity. And the aggregation among molecules can be effectively inhibited by introducing substituent groups, the fluorescence weakening caused by aggregation induction is avoided, the luminous efficiency of the device is improved, and meanwhile, the triplet state energy level of the molecules can be effectively regulated and controlled, and the service life of the device is effectively prolonged.
The applicant states that the organic compounds of the present invention and their use are illustrated by the above examples, but the present invention is not limited to, i.e. it is not meant that the present invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.

Claims (10)

1. An organic compound having the structure of formula i:
wherein n is 1 、n 2 、n 3 、n 4 Independently selected from 0, 1 or 2, and not simultaneously 0;
the L is 1 、L 2 、L 3 、L 4 Independently selected from single bond, phenyl, and groups formed by connecting or fusing 2 to 3 phenyl groups through single bond;
the R is 1 、R 2 、R 3 、R 4 Independently selected from the group consisting of substituted or unsubstituted phenyl, fused aromatic groups formed by singly bonding or fusing 2 to 5 phenyl groups, monocyclic heteroaryl groups, fused ring heteroaryl groups formed by fusing 2 to 5 phenyl groups and monocyclic heteroaryl groups, fluorenyl, spirofluorenyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, silafluorenyl, spirosilafluorenyl, NR 5 R 6 ；
The heteroatoms in the monocyclic heteroaryl are selected from one or more of N, O, S, si;
the R is 5 、R 6 Independently selected from phenyl, groups formed by 2 to 3 phenyl groups linked by single bonds or condensed;
the R is 1 、R 2 、R 3 、R 4 The substituent groups of (C) are independently selected from deuterium, F, cl, br, C-C6 alkyl, fluoro-C1-C6 alkyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, C1-C6 alkyl substituted phenyl, fluoro-phenyl, N-diphenylamino and N, N-dinaphthylamino.
2. The organic compound according to claim 1, wherein,the L is 1 、L 2 、L 3 、L 4 Independently selected from single bond, phenyl, biphenyl, naphthyl or anthracenyl.
3. The organic compound according to claim 1, wherein R 1 、R 2 、R 3 、R 4 Independently selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyranyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, benzophenanthryl, silafluorenyl, spirosilafluorenyl, benzofurocarbazolyl, benzofurophenyl, fluorenyl, spirofluorenyl, N-diphenylamino, N-dinaphthylamino, any of the structures represented by formulas a-c:
X 1 、X 2 、X 3 、X 4 independently selected from O or S;
X 5 selected from N.
4. The organic compound according to claim 1, wherein R 1 、R 2 、R 3 、R 4 Independently selected from any one of the following structures:
# denotes a connection position.
5. The organic compound according to claim 1, wherein R 1 、R 2 、R 3 、R 4 Is independently selected from deuterium, F, cl, br, methyl, fluoromethylA group, ethyl group, fluoroethyl group, N-propyl group, isopropyl group, N-butyl group, isobutyl group, t-butyl group, trimethylsilyl group, cyclopentyl group, cyclohexyl group, phenyl group, naphthyl group, methylphenyl group, fluorophenyl group, N-diphenylamino group, N-dinaphthylamino group.
6. The organic compound according to claim 1, wherein n 1 、n 2 、n 3 、n 4 Any 1 to 3 of them are 1, and the rest are 0.
7. An organic compound characterized by having any one of the following structures:
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8. use of an organic compound according to any one of claims 1-7 as blue light doped material.
9. An organic light-emitting device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer comprising a light-emitting layer containing at least one organic compound according to any one of claims 1 to 7.
10. A display panel comprising the organic light emitting device of claim 9.
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