CN109705132A - A kind of hot activation delayed fluorescence compound and its application - Google Patents
A kind of hot activation delayed fluorescence compound and its application Download PDFInfo
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 7
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- 238000006467 substitution reaction Methods 0.000 claims description 3
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Abstract
The present invention relates to electroluminescent organic material technical field, a kind of hot activation delayed fluorescence compound and its application are disclosed.Hot activation delayed fluorescence compound provided by the present invention, singlet and triplet difference are smaller, are conducive to raising triplet excitons to the backlass of singlet exciton and alter more probability；In addition, while keeping lower singlet and triplet difference, hot activation delayed fluorescence compound S1 also with higher provided by the present invention is to S0 electron transition a period of time intensity, so that this kind of hot activation delayed fluorescence compound light radiation transfer rate with higher, is conducive to the luminous efficiency for improving compound.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent devices, in particular to a thermally activated delayed fluorescence compound and application thereof.
Background
Organic electroluminescent materials are classified into fluorescent electroluminescent materials and phosphorescent electroluminescent materials. Among them, the phosphorescent electroluminescent material can utilize the energy of all excitons through the heavy metal effect, and thus has greater advantages. In 2009, a thermally activated delayed fluorescence compound, namely, a tadf (thermally activated delayed fluorescence) material, was proposed and applied to the technical field of organic electroluminescent devices. The fluorescent compound can obtain 100% singlet excitons by utilizing reverse gap crossing of triplet excitons under thermal excitation, thereby avoiding the use of expensive heavy metal complexes and ensuring that the device efficiency can be comparable with that of phosphorescent devices. Since then, fluorescent materials have attracted renewed attention from researchers.
However, the existing thermally activated delayed fluorescence compound and the device prepared by the compound have many defects, such as limited material types, and the stability of the device to be improved. In the related art, to design thermally activated delayed fluorescence compounds and achieve lower Δ ESTIt is necessary to achieve a strict and complete separation of the HOMO and LUMO orbitals in a molecule by a technique that achieves this separationAnd a barrier unit design is adopted between the electron pushing unit and the electron withdrawing unit in the molecule. Such conventional molecular design has achieved the desired Δ ESTThe value, but complete HOMO-LUMO orbital separation and insertion of the blocking unit, results in electron exchange integrals in the HOMO and LUMO molecules approaching 0, i.e., the radiative transition rate constant Kr @ S1->S becomes small, which is not beneficial to improving the luminous efficiency of molecules. In addition, the middle blocking unit causes the molecular structure to be more flexible, so that the light radiation transition constant and the strength of the array during transition of the molecule are reduced (Kr is proportional to the strength f of the array).
Therefore, it is necessary to provide a thermally activated delayed fluorescence compound which not only has a low Δ EST, but also maintains a better luminescence efficiency and a higher intensity of the light-emitting transition lattice of the molecule.
Disclosure of Invention
The invention aims to overcome the defects and provide a thermal activation delayed fluorescence compound and application thereof, wherein delta E of the thermal activation delayed fluorescence compoundST(singlet and triplet energy level difference) is low, and has high intensity of S1 to S0 electron transition and high optical radiation transition rate.
In order to solve the above technical problems, embodiments of the present invention provide a thermally activated delayed fluorescence compound having a structure represented by formula (i) or formula (II):
wherein,
X1、X2is also O or X1、X2The same is S;
R1、R2each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C,Substituted or unsubstituted C5-C36 heteroaryl, substituted or unsubstituted amino;
d has a structure represented by formula (III):
in the formula (III), the compound represented by the formula (III),
R3、R4、R5、R6each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C36 heteroaryl group, a substituted or unsubstituted amino group, and R3、R4、R5、R6Each independently is 1-4;
X3selected from C or Si.
Alternatively, in the structure of the thermally activated delayed fluorescence compound provided by the embodiment of the present invention, the substitution in the substituted or unsubstituted C1-C8 alkyl group, substituted or unsubstituted C6-C36 aryl group, substituted or unsubstituted C5-C36 heteroaryl group, and substituted or unsubstituted amino group means: the C1-C8 alkyl, C6-C30 aryl, C5-C30 heteroaryl and amino are respectively and independently substituted by a substituent selected from one of the following groups:
wherein R is1’、R2' are each independently selected from substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C30 aryl.
Alternatively, the thermally activated delayed fluorescence compound provided by the embodiments of the present invention has a structure，R1、R2Each independently selected from a hydrogen atom, a substituted or unsubstituted C1-C8 alkyl group.
Alternatively, the thermally activated delayed fluorescence compound provided by the embodiment of the present invention has a structure in which R is3、R4、R5、R6Each independently selected from hydrogen atom, deuterium atom, C1-C8 alkyl, phenyl, carbazolyl, phenyl substituted amino.
Alternatively, the thermally activated delayed fluorescence compound provided by the embodiment of the present invention has a structure in which R is3、R4、R5、R6Each independently is 1-2.
Alternatively, embodiments of the invention provide thermally activated delayed fluorescence compounds having a structure selected from one of L1-L38:
embodiments of the present invention also provide the use of the thermally activated delayed fluorescence compounds described above in OLED, OFT, OPV, QLED devices.
Embodiments of the present invention also provide an organic light emitting diode including the thermally activated delayed fluorescence compound described above.
Preferably, the thermally activated delayed fluorescence compound is included in a light emitting layer of the organic light emitting diode.
The thermal activation delayed fluorescence compound provided by the invention adopts furyl benzofuran functional group (or thienyl benzothiophene functional group) and spiral [ acridine-9, 9' fluorene]The molecular structure design with vertical functional groups. Spiro [ acridine-9, 9' fluorene as electron donating unit in its molecular structure]The functional group forms the HOMO of the molecule, and the furanylbenzofuran functional group (or thiophenylbenzothiophene functional group) as an electron-withdrawing unit forms the LUMO of the molecule, both vertically and partially overlapping in spatial position. The molecular structure design enables the compound provided by the invention to have the following beneficial effects in the application process of the compound as an organic electroluminescent material: (1) delta E of the Compounds provided by the inventionST(difference between singlet state and triplet state energy level) less than 300meV, and minimum even only 6meV, and lower Delta E when the material is used as a luminescent layer material in an organic electroluminescent deviceSTThe reverse gap crossing probability from the triplet excitons to the singlet excitons is improved; (2) the partial overlapping of the HOMO and LUMO spatial positions enables the compound molecules provided by the invention to keep the Delta E lowerSTAt the same time, at S1->The transition process of S0 has higher S1->S0 electron transition oscillator intensity: f @ S1->S0>0.3, so that the material has higher optical radiation transition rate, and the luminous efficiency of the material is favorably improved; (3) furanylbenzofuran functional groups (or thienylbenzothiophene functional groups) and spiro [ acridine-9, 9' fluorene]The functional groups are rigid structures, no intermediate barrier unit is adopted in the whole molecular structure of the compound, and the molecular structure has very high rigidity, thereby further ensuring that the compound provided by the invention has very high S1->S0 electron transition oscillator intensity.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, embodiments of the present invention will be described in detail below. However, it will be appreciated by those of ordinary skill in the art that numerous technical details are set forth in order to provide a better understanding of the present invention in its various embodiments. However, the technical solutions claimed in the claims of the present invention can be implemented without these technical details and with various changes and modifications based on the following embodiments.
Compound (I)
A specific embodiment of the present invention provides a thermally activated delayed fluorescence compound having a structure represented by formula (I) or formula (II):
wherein,
X1、X2is also O or X1、X2The same is S;
R1、R2each independently selected from a hydrogen atom, a deuterium atom, a halogen, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C36 heteroaryl group, a substituted or unsubstituted amino group;
d has a structure represented by formula (III):
in the formula (III), the compound represented by the formula (III),
R3、R4、R5、R6each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C36 heteroaryl group, a substituted or unsubstituted amino group, and R3、R4、R5、R6Each independently is 1-4;
X3selected from C or Si.
In some embodiments of the invention, the substitution in the substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C5-C36 heteroaryl, substituted or unsubstituted amino means: the C1-C8 alkyl, C6-C30 aryl, C5-C30 heteroaryl and amino are respectively and independently substituted by a substituent selected from one of the following groups:
wherein R is1’、R2' are each independently selected from substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C30 aryl.
In some embodiments of the invention, R1、R2Each independently selected from a hydrogen atom, a substituted or unsubstituted C1-C8 alkyl group.
In some embodiments of the invention, R3、R4、R5、R6Each independently selected from hydrogen atom, deuterium atom, C1-C8 alkyl, phenyl, carbazolyl, phenyl substituted amino.
In some embodiments of the invention, R3、R4、R5、R6Each independently is 1-2.
In some embodiments of the invention, a thermally activated delayed fluorescence compound is provided having a structure selected from one of L1-L38:
general synthetic route
The following sections disclose methods for preparing the compounds provided by the present invention. The present disclosure is not intended to be limited to any one of the methods recited herein. One skilled in the art can readily modify the methods described or utilize different methods to prepare one or more of the provided compounds. The following aspects are merely exemplary and are not intended to limit the scope of the present disclosure. The temperature, catalyst, concentration, reactant composition, and other process conditions may vary, and one skilled in the art to which this disclosure pertains may readily select appropriate reactants and conditions for the desired complex.
CDCl on a Varian Liquid State NMR instrument3Or DMS0-d6Recording at 400MHz in solution1H spectrum, recorded at 100MHz13C NMR spectrum, chemical shift referenced to residual deuterated solvent. If CDCl3As a solvent, tetramethylsilane (δ ═ 0.00ppm) was used as an internal standard for recording1H NMR spectrum using DMSO-d6(δ 77.00ppm) is reported as an internal standard13C NMR spectrum. If H is present2When O (delta. 3.33ppm) is used as solvent, residual H is used2O (δ ═ 3.33ppm) was recorded as an internal standard1H NMR spectrum; using DMSO-d6(delta. 39.52ppm) is recorded as internal standard13C NMR spectrum. The following abbreviations (or combinations thereof) are used for explanation1Multiplicity of H NMR: s is singleplex, d is doublet, t is triplet, q is quartet, P is quintuple, m is multiplet, br is wide.
The general synthetic route of the compound provided by the invention is as follows:
wherein,
X1、X2is also O or X1、X2The same is S;
R1、R2each independently selected from a hydrogen atom, a deuterium atom, a halogen, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C36 heteroaryl group, a substituted or unsubstituted amino group;
R3、R4、R5、R6each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C36 heteroaryl group, a substituted or unsubstituted amino group, and R3、R4、R5、R6Each independently is 1-4;
X3selected from C or Si.
In addition, Pd2(dba)3Tris (dibenzylideneacetone) dipalladium; HPtBu3BF4Is a kind of phosphor.
Synthesis example:
(1) compound L1
Adding A1 and B1 into a flask under the protection of inert gas argon, then fully refluxing and reacting for 30-60 minutes through a dry toluene solution, and slowly adding Pd2(dba)3/HPtBu3BF4As catalystReacting for 30-60 min, and slowly adding NaO under the protection of Ar gastAnd heating the Bu solution to 100-120 ℃, and stirring for reacting for 24 hours. After the reaction, the mixture is filtered by suction, washed by toluene and ethanol, and then purified by using a column, wherein the organic solvent is CH2Cl2N-hexane, and purifying to obtain powder with purity of more than 99%.
In order to further improve the purity of the L1, the L1 product with the purity of more than 99.5 percent can be obtained by one or more times of sublimation by a vacuum sublimation apparatus, and the yield is 28 percent.
Using CDCl3As solvent tetramethylsilane (δ ═ 0.00ppm) was recorded as internal standard1H NMR spectrum.
1H NMR(400MHZ,DMSO-d6)：
6.34ppm(4H,d),6.50ppm(4H,q),6.81-6.82ppm(8H,t),7.06ppm(2H,s),7.28ppm(4H,t),7.38ppm(4H,4H,t),7.53-7.55ppm(6H,t),7.84ppm(4H,d)。
(2) Compound L2
Adding A2 and B2 into a flask under the protection of inert gas argon, then fully refluxing and reacting for 30-60 minutes through a dry toluene solution, and slowly adding Pd2(dba)3/HPtBu3BF4Fully reacting for 30-60 minutes as a catalyst, and slowly adding NaO under the protection of Ar gastAnd heating the Bu solution to 100-120 ℃, and stirring for reacting for 24 hours. After the reaction, the mixture is filtered by suction, washed by toluene and ethanol, and then purified by using a column, wherein the organic solvent is CH2Cl2N-hexane, and purifying to obtain powder with the purity of more than 99 percent, namely L2.
In order to further improve the purity of the L2, the L2 product with the purity of more than 99.5 percent can be obtained by one or more times of sublimation by a vacuum sublimation apparatus, and the yield is 28 percent.
Using CDCl3As solvent tetramethylsilane (δ ═ 0.00ppm) was recorded as internal standard1H NMR spectrum.
1H NMR(400MHZ,DMSO-d6)：
6.33-6.34ppm(6H,d),6.50ppm(4H,t),6.62ppm(2H,s),6.81-6.82ppm(8H,t),7.24-7.28ppm(6H,q),6.38p pm(4H,t),7.55ppm(4H,d),7.84ppm(4H,d)。
(3) Compound L10
Adding A10 and B10 into a flask under the protection of argon inert gas, then fully refluxing and reacting for 30-60 minutes by a dry toluene solution, and then slowly adding Pd2(dba)3/HPtBu3BF4Fully reacting for 30-60 min as catalyst, and slowly adding NaO under the protection of Ar gastAnd heating the Bu solution to 100-120 ℃, and stirring for reacting for 24 hours. After reaction, the mixture is filtered, washed by toluene and ethanol, and then purified by using a column, wherein the organic solvent is CH2Cl2N-hexane, and purifying to obtain powder with the purity of more than 99%, namely L10, and the yield is 28%.
In order to further improve the purity of the L10, the L10 product with the purity of more than 99.5 percent can be obtained by one or more times of sublimation by a vacuum sublimation apparatus.
Using CDCl3As solvent tetramethylsilane (δ ═ 0.00ppm) was recorded as internal standard1H NMR spectrum.
1H NMR(400MHZ,DMSO-d6)：
2.35ppm(12H,s),6.34ppm(4H,d),6.50-6.53ppm(6H,q),6.81-6.82ppm(8H,t),7.06-7.08ppm(6H,d),7.43ppm(4H,d),7.53ppm(2H,d),7.64ppm(4H,d)。
It should be noted that, in addition to the above-mentioned compounds of L1, L2 and L10, the synthetic routes of other compounds provided by the present invention follow the same methods and procedures as those of the above-mentioned examples of the synthesis of compounds of L1, L2 and L10.
Photophysical information:
when the electronic structure of a fluorescent small-molecule compound is researched, the mutual influence among electrons is very important, the Density Functional Theory (DFT) is widely used for researching a pi conjugated system, and the result of researching the photoelectric property of the compound provided by the invention by adopting a DFT method is more accurate than that of other methods. The geometric structure of the compound molecules in the ground state, the cation state and the anion state is optimized by adopting the method of DFT// B3LYP/6-31G (d), and the geometric structure of the excited state of the compound is obtained by adopting the method of DFT// B3LYP/6-31G (d). The absorption and emission spectra of these compounds were calculated using the time-density functional theory (TDDFT) method on the basis of the ground state and excited state geometries. By the above calculation methods, various properties of the compound under study can be obtained, including ionization energy IP, electron affinity EA, recombination energy λ, highest occupied orbital HOMO, lowest occupied orbital LUMO, and energy gap Eg.
It is very important for organic light emitting devices that holes and electrons can be injected and transported in an efficient balance. The ionization energy and electron affinity of a molecule are used to evaluate the injection capability of holes and electrons, respectively. Table 2 below lists the calculated vertical ionization energy IP (v) and adiabatic ionization energy IP (A), vertical electron affinity EA (v) and adiabatic electron affinity EA (A), hole extraction energy HEP and electron extraction energy EEP for a portion of the compounds. Vertical ionization energy ip (v) refers to the energy difference of the cation and the molecule in neutral molecular geometry; adiabatic ionization energy ip (a) refers to the difference in energy in neutral and cationic geometries; the vertical electron affinity ea (v) refers to the difference in energy in neutral and anionic geometries; adiabatic electron affinity, ea (a), refers to the difference in energy in neutral and anionic geometries; the hole extraction energy HEP refers to the energy difference between a molecule and a cation in the cation geometry; electron extraction energy, EEP, refers to the difference in energy between a molecule and an anion in anion geometry. Generally, for small molecule organic materials, the smaller the ionization energy, the easier the injection of holes; the greater the electron affinity, the easier the electron injection.
From a microscopic perspective, the transport mechanism of charges in organic thin films can be described as a process of self-transport. Wherein an electron or hole is transferred from one charged electron molecule to an adjacent neutral molecule. According to Marcus theory, the mobility of the charge can be expressed as:
wherein T represents temperature; v represents a pre-exponential factor and is a coupling matrix element between two types of particles; λ is the recombination energy; kb is boltzmann's constant. It is clear that λ and V are the decisions KetImportant factors of the value. Generally, the range of charge transfer in the amorphous state is limited, and the variation in V value is small. Therefore, the magnitude of mobility is mainly determined by λ in the index. The smaller λ, the greater the mobility. For convenience of study, the influence of external environment is ignored, and the main discussion is the internal recombination energy.
According to computational derivation, the recombination energy can be finally expressed as:
λh。le＝IP(v)-HEP
λelectron＝EEP-EA(v)
in general, in organic materials, S is caused by the difference in the degree of self-rotation1Excited state and T1Excited state energy is different, and ES1Energy ratio of ET1The energy is 0.5-1.0 ev larger, which causes the low luminous efficiency of the pure organic fluorescent material. The thermal delayed fluorescence TADF material separates the HOMO-LUMO orbitals due to unique molecular design, reduces the electron exchange energy of the HOMO-LUMO orbitals and can theoretically realize Delta EST0-0. To effectively evaluate the thermally delayed fluorescence effect of the materials of the present invention, Δ E was performedSTEvaluation, the TDDFT method is used to obtain the lowest singlet excitation energy Es and the lowest singlet excitation energy Es of the compound provided by the inventionDifference Δ E of triplet excitation energy ETST。
f @ S1-S0, defined as the intensity of the transition matrix of the exciton at S1- > S0, and has the following meaning: the larger f @ S1-S0 means the larger transition radiation rate Kr of the exciton at S1- > S0; conversely, a smaller f @ S1-S0 means a smaller transition radiation rate Kr of the exciton at S1- > S0. If the transition radiation rate Kr of the exciton at S1- > S0 is larger, the transition non-radiation rate Knr of the exciton at S1- > S0 is reduced, which is advantageous in improving the light emitting efficiency of the material, and the exciton is either used for light radiation or is annihilated by non-radiation (e.g., thermally inactivated). See Table 1, this embodiment also evaluates the f @ S1-S0 constants.
The HOMO level, LUMO level, electron cloud distribution of HOMO and LUMO, f @ S1-S0 constant, and Δ E of the compound provided by the present invention were calculated as aboveSTAnd a T1 level, and table 1 below gives specific photophysical information data, for example, compounds L1-L6:
TABLE 1 photophysical information data
Based on the above calculation results, it is demonstrated that the structure of the thermally activated delayed fluorescence compound provided by the embodiment of the present invention includes a thienylbenzothiophene (furan) functional group and spiro [ acridine-9, 9' fluorene ]]The C-N bonds between the functional groups form a specific 90 degree space angle, thereby providing compounds having a lower Δ ESTA proper T1 energy level, and ensures proper orbital overlap between HOMO-LUMO to obtain a higher radiation transition rate constant, and the photoelectric properties are favorable for obtaining higher photoelectric properties of the provided compound.
Another advantage of thermally activated delayed fluorescence organic compounds provided by embodiments of the present invention is that all compounds have very high f @ S1-S0 constants, e.g., f @ S1-S0-0.4296 for L1, f @ S1-S0-0.5304 for L2, f @ S1-S0-S0.4531 for L3, f @ S1-S0 for L4-0.5326. The f @ S1-S0 constants are defined as: the larger the transition lattice intensity of the exciton at S1- > S0, f @ S1-S0, means that the transition radiation rate Kr of the exciton at S1- > S0 is larger; the smaller f @ S1-S0 means the smaller transition radiation rate Kr of the exciton at S1- > S0. If the transition radiation rate Kr of the exciton at S1- > S0 is larger, the transition non-radiation rate Knr of the exciton at S1- > S0 is reduced, which is advantageous for improving the luminous efficiency of the material, meaning that the exciton is either used for light radiation or is annihilated by non-radiation (e.g., thermally inactivated). It is reasonably expected from the common general knowledge in the art that the thermally activated delayed fluorescence compound provided by the embodiments of the present invention has very good luminous efficiency.
Another advantage of the thermally activated delayed fluorescence organic compound provided by the embodiments of the present invention is that the provided compound achieves a higher hole transporting property or electron transporting property characteristic with a very simple molecular design. Table 2 below gives, by way of example, the detailed calculation tables for IPV, IPA, EAV, EAA, HEP, EEP,. lambda.h,. lambda.e, in the case of compounds L1-L6.
TABLE 2 IPV, IPA, EAV, EAA, HEP, EEP, λ h, λ e calculation Table
Judging from the calculated hole recombination energy and electron recombination energy, for the L1 molecule: [ electron recombination energy λ e-hole recombination energy λ h ] ═ 0.22eV, and therefore, the molecule L1 is a thermally activated delayed fluorescence organic material having a highly desirable hole-bias transport property.
For the L6 molecule: [ electron recombination energy λ e — hole recombination energy λ h ] ═ 0.15eV, and therefore, the L2 molecule is a thermally activated delayed fluorescence organic material with a hole transport ability slightly stronger than an electron transport ability. Compared with L1, the L6 molecule obviously improves the matching of hole/electron transport capability of the L6 material due to the addition of four diphenylamine compounds on the HOMO, and is beneficial to balancing the transport balance of hole/electron carriers of an OLED device, thereby improving the luminous efficiency and the service life of the OLED.
Device with a metal layer
Embodiments of the present invention also provide the use of the thermally activated delayed fluorescence compounds of the above examples in devices.
In some embodiments of the invention, the device may be an OLED, OFT, OPV, QLED device.
Embodiments of the present invention also provide an organic light emitting diode device comprising the thermally activated delayed fluorescence compound of the above examples.
In some embodiments of the present invention, the thermally activated delayed fluorescence compound is a material of a light emitting layer in the organic light emitting diode device.
In some embodiments of the present invention, there is provided an organic light emitting diode device comprising: the light-emitting layer is a thermally activated delayed fluorescence compound in the invention.
Organic light emitting diode device example
(1) As guest materials
And constructing a multilayer device structure of ITO/HIL/HTL/light-emitting layer/ETL/EIL/cathode. To facilitate the understanding of the technical advantages and device principles of the present invention, the present invention is described in terms of the simplest device structure.
ITO/HIL(10nm)/HTL(30nm)/HTL(30nm)/HOST：L5,6wt％,30nm/ETL(30nm)/LiF(1nm)/Al。
TABLE 3 partial comparison of device Performance
Efficiency roll off, defined herein as 0.1mA/cm2Efficiency to 100mA/cm2Rate of change of performance.
As can be seen from the data in Table 3, the performance roll-off of the OLED device using the compound provided by the invention is small, and the maximum EQE is more than 5%.
Finally, it will be understood by those skilled in the art that the foregoing embodiments are specific examples of the invention, and that various changes in form and detail may be made therein without departing from the spirit and scope of the invention in practice.
Claims (9)
1. A thermally activated delayed fluorescence compound having a structure represented by formula (I) or formula (II):
wherein,
X1、X2is also O or X1、X2The same is S;
R1、R2each independently selected from hydrogen atom, deuterium atomHalogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C5-C36 heteroaryl, substituted or unsubstituted amino;
d has a structure represented by formula (III):
in the formula (III), the compound represented by the formula (III),
R3、R4、R5、R6each independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C8 alkyl group, a substituted or unsubstituted C6-C36 aryl group, a substituted or unsubstituted C5-C36 heteroaryl group, a substituted or unsubstituted amino group, and R3、R4、R5、R6Each independently is 1-4;
X3selected from C or Si.
2. A thermally activated delayed fluorescence compound according to claim 1, wherein the substitution in the substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C5-C36 heteroaryl, substituted or unsubstituted amino is: the C1-C8 alkyl, C6-C30 aryl, C5-C30 heteroaryl and amino are respectively and independently substituted by a substituent selected from one of the following groups:
wherein R is1’、R2' are each independently selected from substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C6-C30 aryl.
3. A thermally activated delayed fluorescence compound according to claim 1, wherein R is1、R2Each independently selected from a hydrogen atom, a substituted or unsubstituted C1-C8 alkyl group.
4. A thermally activated delayed fluorescence compound according to claim 1, wherein R is3、R4、R5、R6Each independently selected from hydrogen atom, deuterium atom, C1-C8 alkyl, phenyl, carbazolyl, phenyl substituted amino.
5. A thermally activated delayed fluorescence compound according to claim 1, wherein R is3、R4、R5、R6Each independently is 1-2.
6. A thermally activated delayed fluorescence compound according to claim 1, having a structure selected from one of L1-L38:
7. use of a thermally activated delayed fluorescence compound according to any of claims 1 to 6 in OLED, OFT, OPV, QLED devices.
8. An organic light emitting diode comprising the thermally activated delayed fluorescence compound of any one of claims 1 to 6.
9. The oled according to claim 8, wherein the thermally activated delayed fluorescence compound is contained in a light-emitting layer of the oled.
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| CN112142666A (en) * | 2019-06-27 | 2020-12-29 | 关东化学株式会社 | Spiroacridine compound, hole transport material containing same, and organic electronic device containing same in hole transport layer |
| KR20210125639A (en) * | 2020-04-08 | 2021-10-19 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| JP2009246140A (en) * | 2008-03-31 | 2009-10-22 | Hiroshima Univ | Light-emitting element |
| JP2009246139A (en) * | 2008-03-31 | 2009-10-22 | Hiroshima Univ | Light-emitting element |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2009246140A (en) * | 2008-03-31 | 2009-10-22 | Hiroshima Univ | Light-emitting element |
| JP2009246139A (en) * | 2008-03-31 | 2009-10-22 | Hiroshima Univ | Light-emitting element |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112142666A (en) * | 2019-06-27 | 2020-12-29 | 关东化学株式会社 | Spiroacridine compound, hole transport material containing same, and organic electronic device containing same in hole transport layer |
| KR20210125639A (en) * | 2020-04-08 | 2021-10-19 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR102344802B1 (en) * | 2020-04-08 | 2021-12-30 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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