CN109928936B - Organic electroluminescent compounds and use thereof - Google Patents
Organic electroluminescent compounds and use thereof Download PDFInfo
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Abstract
The invention relates to an organic electroluminescent compound, the structural formula of which is shown as formula (1):
wherein L is1、L2Each independently represents a covalent single bond, phenyl, biphenyl, or trans-distyryl; x1、X2Are respectively and independently selected from hydrogen, aromatic hydrocarbon group with 6-40 ring atoms, aromatic hetero group or aromatic amine group; y is one of formulae W-1 to W-21:
the compound provided by the invention can be used as a fluorescent light-emitting object material, and an electroluminescent device prepared by using the material has the advantages of low driving voltage, high light-emitting efficiency, high spectral color purity and the like.
Description
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to an organic electroluminescent compound and application thereof.
Background
Organic electroluminescent devices have gained much attention since the first report by kodak c.w.tang et al in 1987 of a two-layer light emitting device prepared by vacuum evaporation. Due to their inherent advantages such as ultra-thin, wide viewing angle, and fast response, they have found practical applications in flat panel displays and solid state lighting. However, the development of red/deep red/near infrared luminescent materials is relatively laggard, and they have irreplaceable roles in emerging fields such as security display, night vision device, information security storage, optical communication, biological probe, etc. Therefore, the research and development of novel efficient red/deep red/near infrared luminescent materials have become a hotspot and difficulty in the research of the organic photoelectric field in recent years.
Currently, red/deep red/near infrared luminescent materials are mainly divided into two main categories: transition metal complexes and purely organic conjugated materials having a donor-acceptor (D-A) structure. Wherein, iridium (Ir)3+) Platinum (Pt)2+) The complex of noble metal has been receiving much attention because it can emit light by triplet excitons. However, since such materials have long triplet lifetimes, phosphorescent devices have a large roll-off in efficiency at high luminance. In addition, the red/deep red/near infrared metal complexes need to have large conjugated groups, but at the same time, the molecular weight of the complexes cannot be too large in order to be evaporated, so that the molecular design of the complexes has certain limitations. As another major class of red/deep red/near infrared luminescent materials, traditional fluorescent materials have also been extensively studied because of their cost advantages and easily tunable spectra compared to phosphorescent materials. However, the conventional red fluorescent materials with D-A configuration have the following disadvantages: (1) according to the band gap law, when the spectrum is expanded to a near infrared region, the non-radiative transition efficiency is increased; (2) only 25% of the singlet excitons are available.
Therefore, there remains a significant challenge to realize efficient red/deep red/near infrared fluorescent devices. Although great progress has been made in the field of red/deep red/near infrared organic electroluminescent devices in recent years, the efficiency thereof is still not high. In addition, most of the currently efficient deep red/near infrared light emitting devices do not reach the true deep red/near infrared region.
Disclosure of Invention
In order to solve the above technical problems, an object of the present invention is to provide an organic electroluminescent compound and an application thereof, wherein the organic electroluminescent compound of the present invention can be used as a light-emitting object of a light-emitting layer of an organic electroluminescent device, and has high color purity and high light-emitting efficiency, and the prepared electroluminescent device exhibits superior properties such as low driving voltage.
The first object of the present invention is to provide an organic electroluminescent compound having a structural formula represented by formula (1):
L1、L2each independently represents a covalent single bond, phenyl, biphenyl, or trans-distyryl;
X1、X2are respectively and independently selected from hydrogen, aromatic hydrocarbon group with 6-40 ring atoms, aromatic hetero group or aromatic amine group;
y is one of formulae W-1 to W-21:
when X is present1、X2When it is hydrogen, L1And/or L2Is a covalent single bond.
Further, X1、X2Each independently selected from hydrogen or one of formulae Ar-1 to Ar-26:
wherein the content of the first and second substances,
represents phenyl or substituted phenyl, the substituted phenyl contains at least one substituent selected from halogeno, boranyl and C1-C12Straight chain alkyl、C1-C12Cycloalkyl radical, C1-C12Alkoxy radical, C1-C12Alkylthio, aryl with 6-30 ring atoms, heteroaryl with 6-30 ring atoms or arylamine with 6-30 ring atoms.
Further, C1-C12Straight chain alkyl or C1-C12At least one halo group is present in the cycloalkyl group.
Further, L1、L2Each independently represents a covalent single bond or a phenyl group; x1、X2Each independently selected from phenyl, alkyl or alkoxy substituted benzene, carbazolyl, alkyl or alkoxy substituted carbazole, dianilino, alkyl or alkoxy substituted diphenylamine, phenoxazine, alkyl or alkoxy substituted phenoxazine, phenothiazine, alkyl or alkoxy substituted phenothiazine, spiroacridine, alkyl or alkoxy substituted spiroacridine, oxacyclotriphenylamine or thiacyclotriphenylamine.
Preferably, the organic electroluminescent compounds are preferably of the formula n-1 to n-170; wherein n is an integer of 1 to 21. Wherein the formulas 1-1 to 1-170 are respectively as follows:
in the formulae 2-1 to 2-170, the electron-withdrawing group in 1-1 to 1-170 (corresponding to the group Y in the general formula (1), the same applies hereinafter) is replaced with W-1 to W-2. And the like, in the formulas a-1 to a-170(a is an integer of 3 to 21), the electron-withdrawing group in the formulas 1-1 to 1-170 is replaced by W-1 to W-3 to W-21 respectively.
Preferably, the organic electroluminescent compound is a compound of the formula n ' -1 to n ' -170, n ' being any integer of 1 to 21. Wherein the formula n '-1 to n' -170 is such that the double-sided donor in n-1 to n-170 is changed to a single-sided donor (i.e. the group X in formula (1))1And X2One of which is hydrogen).
In addition to n ' -1 to n ' -170, the compound also comprises n ' -171 to n ' -195, and n ' is any integer of 1 to 21. Wherein formulae 1 '-171 to 1' -195 are as follows:
in the formulae 2 '-171 to 2' -195, the electron-withdrawing group in 1 '-171 to 1' -195 (corresponding to the group Y in the general formula (1), the same applies hereinafter) is replaced with W-1 to W-2. In the formulae a ' -171 to a ' -195(a ' is an integer of 3 to 21), the electron-withdrawing group in 1' -171 to 1' -15 is replaced by W-1 to W-3 to W-21, respectively.
More preferably, the organic electroluminescent compound has a structural formula as shown in formula (2) to formula (4):
the organic electroluminescent compound is connected with different strong electron withdrawing and donating groups on a dibenzo [ a, c ] phenazine intermediate, and molecules have small band gaps and red/deep red/near infrared emission due to strong intramolecular charge transfer; the intermediate has a rigid planar configuration, and can effectively reduce the vibration and rotation of molecules to achieve high radiation transition rate; the Thermally Activated Delayed Fluorescence (TADF) material does not require the use of noble metals such as platinum and iridium, and it can achieve a theoretical 100% exciton utilization rate through an efficient inter-inversion system crossover process.
The preparation method of the organic electroluminescent compound comprises the following steps:
(1) reacting the molecule shown in the formula (A) and the molecule shown in the formula (B) in an organic solution at 125 ℃ to obtain the compound shown in the formula (C) after the reaction is completed, wherein the reaction route is as follows:
wherein, X1、X2、L1、L2And X in the general formula (1)1、X2、L1、L2The groups represented are the same;
x represents a halogen;
(2) reacting the compound shown in the formula (C) with a compound containing a Y group in an organic solution at 90-200 ℃ to obtain the organic electroluminescent compound shown in the general formula (1).
The second purpose of the invention is to disclose the application of the organic electroluminescent compound in the invention as a luminescent material or in the preparation of an organic electroluminescent device.
It is a third object of the present invention to provide an organic electroluminescent device comprising a cathode, an anode and an organic thin film layer disposed between the cathode and the anode, the organic thin film layer comprising at least one organic light emitting layer (EML) containing the above organic electroluminescent compound of the present invention.
Further, the organic light-emitting compound of the present invention is a fluorescent light-emitting guest material.
Further, the organic light emitting layer is composed of a host material and a fluorescent doping material, the fluorescent doping material comprises the organic electroluminescent compound, and the doping proportion of the organic electroluminescent compound is 2 wt.% to 15 wt.%. In the present invention, the doping ratio refers to a mass ratio of the organic electroluminescent compound to the organic light-emitting layer, unless otherwise specified.
Preferably, the doping ratio of the organic electroluminescent compound is preferably 2 wt.%, 5 wt.%, 10 wt.% and 15 wt.%.
Further, the organic thin film layer further includes a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL), and the organic electroluminescent device is sequentially provided with the anode, the HIL, the HTL, the EBL, the EML, the ETL, the EIL, and the cathode in a height direction.
Further, the organic electroluminescent device is an infrared, deep infrared or near infrared electroluminescent device.
Preferably, the anode is ITO.
By the scheme, the invention at least has the following advantages:
the invention provides a luminescent material and can be used for preparing organic electroluminescent devices (such as OLED), the manufacturing cost can be reduced, the organic electroluminescent compound has higher color purity and higher efficiency in the electroluminescent devices, and the organic material can overcome the technical material defects, such as low efficiency and high driving voltage.
The organic electroluminescent compound has smaller band gap, excellent luminescent property and capability of generating redder emission; the composite material has rigid and stable plane configuration and higher color purity, can effectively reduce the vibration and rotation of molecules to achieve high radiation transition rate, and can effectively improve the efficiency of devices. Meanwhile, the organic electroluminescent compound has the advantages of simple synthesis method, flexible and changeable derivation modes and lower preparation cost.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following detailed description is given with reference to the preferred embodiments of the present invention and the accompanying drawings.
Drawings
FIGS. 1, 2 and 3 show a room temperature fluorescence spectrum (PL) and a low temperature phosphorescence spectrum (Phos) of the compounds represented by formulae 1 to 57, 6 to 57 and 10 to 57, respectively;
FIG. 4 is an ultraviolet absorption spectrum (UV-Vis) of the compounds represented by formulas 1-57, 6-57, and 10-57;
FIGS. 5, 6 and 7 are device performance spectra of devices OLED1-OLED4, OLED5 and OLED6, respectively;
FIGS. 8 and 9 are the organic electroluminescence spectra of OLED10-OLED12 and OLED16-OLED18, respectively;
the fluorescence, phosphorescence and ultraviolet absorption spectra of the invention are diluted solution (1X 10) in toluene-5mol/L) in the reaction mixture.
Detailed Description
The following detailed description of embodiments of the present invention is provided in connection with the accompanying drawings and examples. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1:
this example provides methods for the preparation of compounds of formulae 1-57, the synthetic routes and methods are as follows:
(1) intermediate C1(4,4' - (3, 6-dibromodibenzo [ a, c))]Synthesis of phenazine-11, 12-diyl) bis (N, N-diphenylaniline):
to a Schlenk flask containing a mixed solution of 1, 4-dioxane and water (100mL, 1, 4-dioxane/water-10/1, V/V) was added 4, 5-dibromoo-phenylenediamine (1g, 3.76mmol), 4-triphenylamine borate (2.72g, 9.4mmol), and K/V in this order under nitrogen2CO3(2.08g, 15.04mmol) and Pd (PPh)3)4(87mg, 0.075mmol), heated with stirring, and reacted at 90 ℃ overnight. After the reaction is finished, cooling to room temperature, pouring the reaction liquid into 100mL of water, adding Dichloromethane (DCM) for extraction (3X 100mL), collecting an organic layer, drying the organic layer by using anhydrous sodium sulfate, evaporating the solvent, and purifying by column chromatography (petroleum ether/ethyl acetate, 2/1, V/V) to obtain a light yellow solid, namely N4,N4,N4”,N4”Tetraphenyl [1,1':2', 1' -terphenyl]-4,4', 5' -tetramine (formula A in the above scheme)1Compound shown, 1.79g, 80%).1H NMR(400MHz,CDCl3)δ7.21(t,J＝7.7Hz,8H),7.07(d,J＝7.8Hz,8H),6.99(d,J＝8.0Hz,8H),6.92(d,J＝8.3Hz,4H),6.79(s,2H).MALDI-TOF-MS:m/z:calcd for C42H34N4:594.76,found:594.15。
Under nitrogen, add A to a reaction flask containing 50mL of acetic acid1(1.6g，2.69mmol)，B1(3, 6-dibromophenanthrene-9, 10-dione) (820mg, 2.24mmol), and the reaction mixture was heated and stirred at 125 ℃ for 24 hours. Cooling the reaction liquid to room temperature, pouring the solution into ice water, continuously stirring, carrying out vacuum filtration, washing a yellow filter cake with a small amount of ethanol, collecting and recrystallizing to obtain a yellow solid C1(1.62g，78％)。1H NMR(400MHz,CDCl3)δ9.15(d,J＝8.5Hz,2H),8.51(s,2H),8.27(s,2H),7.81(d,J＝8.5Hz,2H),7.32–7.26(m,8H),7.20(d,J＝8.1Hz,4H),7.14(d,J＝7.7Hz,8H),7.04(d,J＝8.0Hz,8H).MALDI-TOF-MS:m/z:calcd for C56H36Br2N4:924.74,found:924.43。
(2) Synthesis of compounds represented by formulas 1-57:
in a glove box, the intermediate C is put into1(500mg,0.54mmol), cuprous cyanide (CuCN) (120mg, 1.35mmol), 25mL of anhydrous N-methylpyrrolidone (NMP) were added to a 55mL microwave tube and reacted with a microwave at 180 ℃ for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added, the separated liquid was extracted with DCM (3 × 100mL), the combined organic phases were dried over anhydrous magnesium sulfate to remove the organic phase solvent, and the crude product was purified by column chromatography using petroleum ether/dichloromethane (PE/DCM, 2/1, V/V) as an eluent to give 1 to 57(353mg, 80%) as a red solid.1H NMR(400MHz,CDCl3)δ9.48(d,J＝8.3Hz,2H),8.77(s,2H),8.35(s,2H),8.00(d,J＝8.4Hz,2H),7.29(t,J＝7.8Hz,8H),7.21(d,J＝8.4Hz,4H),7.15(d,J＝7.8Hz,8H),7.10-7.03(m,8H).MALDI-TOF-MS:m/z:calcd for C58H36N6:816.97,found:816.58。
In the present invention, the synthesis of other intermediates can be performed according to the same procedure as described for the intermediate C1The synthesis is carried out in the same or similar manner. First of all, the corresponding starting materials are reacted with the corresponding donors to form the corresponding starting materials A1(ii) a Corresponding starting materials A1Then mixing with the raw material B1Ring closing reaction to obtain corresponding intermediate C1. Corresponding intermediate C1And reacting with a compound W containing a Y group to produce a final product (a compound represented by the general formula (1)). The difference lies in the difference of the used raw material substrates, the structures of the used raw materials and intermediate compounds are shown in Table 1, wherein, X1、X2、L1、L2And X in the general formula (1)1、X2、L1、L2The groups represented are the same; x represents a halogen:
TABLE 1 structural formulae of the starting materials and intermediates
Example 2:
this example provides methods for the preparation of compounds of formulae 6-57, the synthetic routes and methods are as follows:
to a Schlenk flask containing a mixed solution of 1, 4-dioxane and water (100mL, 1, 4-dioxane/water-10/1, V/V) under nitrogen, the intermediate C prepared in example 1 was added in sequence1(500mg,0.54mmol), 4-pyridineboronic acid (266mg, 2.16mmol), K2CO3(600mg, 4.32mmol) and Pd (PPh)3)4(31mg, 0.027mmol), heated with stirring, and reacted at 90 ℃ overnight. After completion of the reaction, it was cooled to room temperature, the reaction solution was poured into 100mL of water, extracted with Dichloromethane (DCM) (3 × 100mL), the collected organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated, purified by DCM column chromatography, and recrystallized from chloroform to give a yellow orange solid (323mg, 65%).1H NMR(600MHz,CDCl3)δ9.37(d,J＝8.2Hz,2H),8.78(d,J＝5.1Hz,4H),8.67(s,2H),8.27(s,2H),7.92(d,J＝8.3Hz,2H),7.69(d,J＝5.5Hz,4H),7.28(t,J＝7.6Hz,8H),7.18(d,J＝8.3Hz,4H),7.15(d,J＝8.2Hz,8H),7.08-7.02(m,8H).MALDI-TOF-MS:m/z:calcd for C66H44N6:921.12,found:920.3。
Example 3:
this example provides methods for the preparation of compounds of formulae 10-57, the synthetic routes and methods are as follows:
compounds 10-57 reference compounds 6-57 were synthesized except that 4-pyridineboronic acid was replaced with equimolar 5-pyrimidineboronic acid to give a red orange solid (346mg, 75%).1H NMR(400MHz,CDCl3)δ9.54(d,J＝8.3Hz,2H),9.33(s,2H),9.19(s,4H),8.72(s,2H),8.37(s,2H),8.02–7.92(m,2H),7.30(d,J＝7.8Hz,8H),7.22(d,J＝8.4Hz,4H),7.15(d,J＝7.8Hz,8H),7.06(t,J＝7.1Hz,8H).MALDI-TOF-MS:m/z:calcd for C64H42N8:923.10,found:922.36。
Example 4:
the electroluminescent device OLED1-OLED18 taking the compound as a fluorescent guest material comprises: substrate/anode/hole injection layer/hole transport layer/electron blocking layer/organic light emitting layer/electron transport layer/electron injection layer/cathode. The luminescent layer is formed by doping the organic electroluminescent compound in a host material, and the doping proportion is 2 wt.%, 5 wt.%, 10 wt.% and 15 wt.%.
The manufacturing steps of the electroluminescent device are as follows: 1) cleaning a glass substrate with an etched ITO pattern, cleaning the glass substrate with a detergent, performing ultrasonic treatment on the glass substrate with acetone and ethanol for 3 times respectively, performing ultrasonic treatment on the glass substrate with deionized water for one time, and drying the glass substrate in an oven for 20 minutes; 2) treating for 15 minutes by using an ultraviolet ozone machine; 3) placing the ITO substrate, the used metal and organic material into a vacuum cavity, and vacuumizing to less than 4.6 multiplied by 10-6Torr; 4) performing thin film evaporation according to the device structure, wherein the evaporation rate of the hole/electron injection layer is 0.02nm/s, the evaporation rate of the organic material is 0.2nm/s, and the evaporation rate of the metal electrode is 0.6 nm/s; 5) and after the evaporation is finished, the cooling cavity encapsulates the device.
It is to be noted that, although the device is fabricated by the thermal evaporation method as described above, the organic electroluminescent compound of the present application is not limited to the thermal evaporation method or the spin coating method for fabricating the device. Electroluminescent device OLED1 the light-emitting layer structure and device performance of OLED18 are shown in table 2.
Among them, the electroluminescent devices OLED1-OLED4, OLED7-OLED10, and OLED13-OLED16 were doped with different concentrations of red dyes using the compounds represented by formulas 1 to 57, 6 to 57, and 10 to 57 prepared in examples 1 to 3, respectively, and were red organic light emitting diodes using CBP as a host. The materials and thicknesses used for the devices prepared were as follows:
ITO/HAT-CN (10nm)/TAPC (40nm)/TCTA (10 nm)/luminescent layer (20nm)/TmPyPB (55nm)/Liq (2nm)/Al (120 nm).
The OLED5, the OLED11 and the OLED17 are deep red devices which take a radical excited compound formed by CBP and PO-T2T as a host material (the mass ratio of the host material to the host material is 1: 1) and respectively use the compounds shown in the formulas 1-57, 6-57 and 10-57 as guest materials. The materials and thicknesses used for the devices prepared were as follows:
ITO/HAT-CN (10nm)/TAPC (40nm)/TCTA (10 nm)/luminescent layer (20nm)/TmPyPB (55nm)/Liq (2nm)/Al (120 nm).
The OLED6, the OLED12, and the OLED18 are near-infrared organic light emitting diodes having pure films of the compounds represented by the formulae 1 to 57, 6 to 57, and 10 to 57 as light emitting layers, respectively. The materials and thicknesses used for the devices prepared were as follows:
ITO/HAT-CN (10nm)/TAPC (40nm)/TCTA (10 nm)/luminescent layer (20nm)/TmPyPB (55nm)/Liq (2nm)/Al (120 nm).
Wherein the HAT-CN is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene; TAPC is 4,4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ]; TCTA is 4,4' -tris (carbazol-9-yl) triphenylamine; POT2T is ((1,3, 5-triazine-2, 4, 6-triyl) tris (benzene-3, 1-diyl)) tris (diphenylphosphine oxide); TmPyPB is 1,3, 5-tris [ (3-pyridyl) -3-phenyl ] benzene; liq is 8-hydroxyquinoline-lithium; CBP is 4,4' -bis (9-carbazole) biphenyl; 1-57, 6-57 and 10-57 are used red light objects respectively.
TABLE 2 light emitting layer Structure and device Properties of electroluminescent device OLED1-OLED18
The specific performance curves of the devices OLED1-OLED4 are detailed in FIG. 5; the specific performance curve of the OLED5 is detailed in fig. 6; the specific performance curve of the OLED6 is detailed in fig. 7; the electroluminescence spectra of the OLEDs 10-12 and 16-18 are shown in FIGS. 8 and 9, FIGS. 8a-c are the electroluminescence spectra of OLEDs 10,11 and 12, respectively, and FIGS. 9a-c are the electroluminescence spectra of OLEDs 16, 17 and 18, respectively. It is noteworthy that for devices OLED4, OLED5, and OLED6, the external quantum efficiency is higher than for similar device structures that exist today. From the above parameters, the organic light emitting material provided by the present invention has great advantages in application of organic light emitting diodes.
Since the organic electroluminescent compounds represented by the formula (1) all have similar structures, they include an electron donor X1And X2And an electron withdrawing group Y, and therefore, such compounds have similar electrochemical properties.
In summary, the following steps: the organic electroluminescent compound shown in the formula (1) is used as a fluorescent guest material of an organic electroluminescent device, and has excellent luminescent characteristics, a stable structure, high color purity and low preparation cost by modifying other different chemical groups. And the red/deep red/near infrared organic electroluminescent device adopting the compound has higher luminous efficiency and excellent performance.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (8)
1. An organic electroluminescent compound, characterized in that the structural formula is as shown in formula (1):
L1and L2Selected from the same group, X1And X2Selected from the same group;
L1、L2represents a covalent single bond, phenyl, biphenyl or trans-distyryl;
y is one of formulae W-1 to W-21:
X1、X2selected from hydrogen or one of the formulae Ar-1 to Ar-26:
wherein the content of the first and second substances,
represents phenyl or substituted phenyl, the substituted phenyl contains at least one substituent selected from halogeno, boranyl and C1-C12Straight chain alkyl, C1-C12Cycloalkyl radical, C1-C12Alkoxy radical, C1-C12Alkylthio, aryl with 6-30 ring atoms, heteroaryl with 6-30 ring atoms or arylamine with 6-30 ring atoms.
2. The organic electroluminescent compound according to claim 1, wherein: l is1、L2Each independently represents a covalent single bond or a phenyl group; x1、X2Each independently selected from phenyl and C1-C12Straight chain alkyl, C1-C12Cycloalkyl or C1-C12Alkoxy-substituted phenyl, carbazolyl, C1-C12Straight chain alkyl, C1-C12Cycloalkyl or C1-C12Alkoxy-substituted carbazolyl,Diphenylamino group, C1-C12Straight chain alkyl, C1-C12Cycloalkyl or C1-C12Alkoxy-substituted dianilino, phenoxazinyl, C1-C12Straight chain alkyl, C1-C12Cycloalkyl or C1-C12Alkoxy-substituted phenoxazinyl, phenothiazinyl, C1-C12Straight chain alkyl, C1-C12Cycloalkyl or C1-C12Alkoxy-substituted phenothiazinyl, spiroacridinyl, C1-C12Straight chain alkyl, C1-C12Cycloalkyl or C1-C12Alkoxy-substituted spiroacridinyl, oxacyclotriphenylaminyl or thiacyclotriphenylaminyl groups.
3. The organic electroluminescent compound according to claim 1, wherein: the structural formula is shown as formula (2) -formula (4):
4. use of the organic electroluminescent compounds as claimed in any of claims 1 to 3 as light-emitting materials or for the production of organic electroluminescent devices.
5. An organic electroluminescent device, characterized in that: comprising a cathode, an anode and an organic thin film layer disposed between the cathode and the anode, the organic thin film layer comprising at least one organic light-emitting layer containing the organic electroluminescent compound as claimed in any one of claims 1 to 3.
6. The organic electroluminescent device according to claim 5, wherein: the organic light emitting layer is composed of a host material and a fluorescent dopant material including the organic electroluminescent compound according to any one of claims 1 to 3.
7. The organic electroluminescent device according to claim 6, wherein: a doping proportion of the organic electroluminescent compound of 2-15 wt. -% ]
8. The organic electroluminescent device according to claim 5, wherein: the organic electroluminescent device is an infrared, deep infrared or near infrared electroluminescent device.
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| CN107827879B (en) * | 2017-09-14 | 2021-06-04 | 奥来德(上海)光电材料科技有限公司 | Material for flexible display, preparation method thereof and organic electroluminescent device |
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