CN113956235B - Thermally activated delayed fluorescence material, application thereof, electroluminescent device and display device - Google Patents
Thermally activated delayed fluorescence material, application thereof, electroluminescent device and display device Download PDFInfo
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Abstract
A thermal activation delayed fluorescence material and application thereof, an electroluminescent device and a display device are disclosed, wherein the thermal activation delayed fluorescence material has a D-L-A structure shown as a formula I, and the meanings of a substituent group and a group in the formula I are the same as the description. The thermally activated delayed fluorescence material disclosed by the embodiment of the disclosure has smaller singlet state-triplet state splitting energy, can promote the singlet state-triplet state splitting energy process, and realizes the TADF effect.
Description
Technical Field
The disclosed embodiments relate to, but are not limited to, the field of display technologies, and in particular, to a thermally activated delayed fluorescence material, an application thereof, an electroluminescent device, and a display apparatus.
Background
In recent years, a Thermally Activated Delayed Fluorescence (TADF) polymer having a Charge Transfer (CT) emission has been attracting attention because it can convert triplet excitons into singlet excitons through a Reverse Intersystem Crossing (RISC) process, thereby achieving 100% Internal Quantum Efficiency (IQE), providing a promising approach for the development of solution-processed organic electroluminescent devices without a noble metal complex.
To ensure an efficient RISC process, TADF materials need to have a small singlet-triplet splitting energy (Δ Est), corresponding to an efficient separation of their highest occupied molecular orbital level-lowest unoccupied molecular orbital level (HOMO-LUMO). In the initial phase of TADF studies, even now, HOMO-LUMO separation is usually achieved by covalent bonding of electron donor and acceptor units. Conventional TADF emitters have a large oscillator intensity (f) and a high Photoluminescence Quantum Yield (PLQY) due to strong electron coupling between the donor and acceptor. However, due to their strong electron coupling, TADF emitter molecules have a relatively large Δ Est, which is detrimental to RISC processes.
By spatially acting HOMO and LUMO on the donor (D) and acceptor (a) parts of the TADF emitter molecule of the D-a structure, respectively, electron exchange integral of the leading molecular orbital is minimized, resulting in an excessive decrease of the oscillator intensity (f). This strategy may result in a reduction in PLQY for TADF emitters due to a transient reduction in oscillator intensity (f), which corresponds to a slower rate of radiation decay. Therefore, a balance needs to be struck between adjusting Δ Est, f and slow non-radiative decay to produce efficient TADF emitters and Organic electroluminescent devices (OLEDs).
Disclosure of Invention
The following is a summary of the subject matter described in detail herein. This summary is not intended to limit the scope of the present disclosure.
The embodiment of the present disclosure provides a thermally activated delayed fluorescence material, which has a D-L-a structure as shown in formula I:
wherein, L is any one of substituted or unsubstituted arylene, heteroarylene, norbornenyl, polynorbornenyl and triptycenyl; here, substituted arylene, substituted heteroarylene, substituted naphthylene, substituted phenanthrylene, substituted dibenzothiophenylene, substituted dibenzofuranylene, substituted carbazolyl, substituted fluorenylene, substituted spirofluorenylene, substituted norbornenyl, substituted polynorbornenyl, substituted triptycenyl, substituted acenaphthylene are substituted with one or more of the following groups: aryl, heteroaryl, naphthyl, phenanthryl, dibenzothienyl, dibenzofuranyl, carbazolyl, fluorenyl, spirofluorenyl, norbornenyl, polynorbornenyl, triptycenyl, acenaphthenyl;
d is a group which can provide charge and has donor properties, and is any one of substituted C3 to C60 monocyclic heteroaryl, substituted C3 to C60 fused ring heteroaryl, substituted C6 to C60 monocyclic aryl and substituted C9 to C60 fused ring aryl; here, substituted C3 to C60 monocyclic heteroaryl, substituted C3 to C60 fused ring heteroaryl means substituted with one or more of the following groups: c3 to C60 monocyclic heteroaryl, C3 to C60 fused ring heteroaryl, C6 to C60 monocyclic aryl, C9 to C60 fused ring aryl, substituted amine; substituted C6 to C60 monocyclic aryl, substituted C9 to C60 fused ring aryl means substituted with one or more of the following groups: monocyclic heteroaryl of C3 to C60, fused ring heteroaryl of C3 to C60, substituted amine; substituted amine groups refer to substitution with one or more of the following groups: substituted C6 to C60 monocyclic aryl, substituted C6 to C60 monocyclic arylene, substituted C9 to C60 fused ring aryl, substituted C9 to C60 fused ring arylene, wherein substituted C6 to C60 monocyclic aryl, substituted C6 to C60 monocyclic arylene, substituted C9 to C60 fused ring aryl, substituted C9 to C60 fused ring arylene means substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C60 monocyclic aryl, C9 to C60 fused ring aryl;
a is a group with acceptor properties capable of accepting the charge provided by D.
In exemplary embodiments, D may be any one of the groups represented by formula II-1, formula II-2, formula II-3:
in formula II-1, Z1 is any one of C, N, O, S, P, B and Se, R1 to R4 are each independently any one of hydrogen, deuterium, C1 to C12 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C3 to C30 heteroaryl, and substituted or unsubstituted C3 to C30 heteroarylene; r5 is any one of a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 heteroarylene group; here, substituted C6 to C30 aryl, substituted C6 to C30 arylene, substituted C3 to C30 heteroaryl, substituted C3 to C30 heteroarylene means substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C30 aryl, C3 to C30 heteroaryl; ar1 is combined on the benzo five-membered ring in a substituted or fused manner, and Ar1 is any one of substituted or unsubstituted C6-C20 aryl, arylene, heteroaryl, heteroarylene, biphenyl and naphthyl; here, substituted C6 to C20 aryl, substituted C6 to C20 arylene, substituted C6 to C20 heteroaryl, substituted C6 to C20 heteroarylene, substituted biphenyl, substituted naphthalene means substituted with one or more of the following groups: c6 to C20 aryl, C6 to C20 heteroaryl, biphenyl, naphthyl; and when Z1 is C, at least one of R1 to R5 and Ar1 contains a heteroaryl or heteroarylene group;
in formula II-2, Z2 is any one of C, N, O, S, P, B and Se, R6 to R13, R15 and R16 are each independently any one of hydrogen, deuterium, C1 to C12 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C3 to C30 heteroarylene; r14 is substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C3 to C30 heteroarylene; here, substituted C6 to C30 aryl, substituted C3 to C30 heteroaryl, substituted C6 to C30 arylene, substituted C3 to C30 heteroarylene means substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C30 aryl, C3 to C30 heteroaryl; and when Z2 is C, at least one of R6 to R16 contains a heteroaryl or heteroarylene group;
in formula II-3, ar2, ar23, ar4 are each independently any one of hydrogen, deuterium, C1 to C12 alkyl, substituted C6 to C60 monocyclic aryl, substituted C6 to C60 monocyclic arylene, substituted C9 to C60 fused ring aryl, substituted C9 to C60 fused ring arylene, and at least one of Ar2, ar23, ar4 is substituted C6 to C60 monocyclic aryl, substituted C6 to C60 monocyclic arylene, substituted C9 to C60 fused ring aryl, or substituted C9 to C60 fused ring arylene; here, the substituted C6 to C60 monocyclic aryl group, the substituted C6 to C60 monocyclic arylene group, the substituted C9 to C60 fused ring aryl group, the substituted C9 to C60 fused ring arylene group means being substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C60 monocyclic aryl, C9 to C60 fused ring aryl.
In an exemplary embodiment, L may be any one of a norbornenyl group, a fluorenylidene group, a naphthylidene group, and an acenaphthylene group.
In exemplary embodiments, D may be any one of the following groups:
in exemplary embodiments, a may be a group containing a triazine structure.
In exemplary embodiments, a may be any one of the following groups:
in an exemplary embodiment, the thermally activated delayed fluorescence material may be any one of the following compounds:
in an exemplary embodiment, D and A are both connected on the same side of L, and the plane of the segment in D and the plane of A present a face-to-face alignment with an angle of inclination, θ, wherein 5 ° < θ < 50 °.
In an exemplary embodiment, 10 ° < θ < 30 °.
In an exemplary embodiment, the distance between the center of the segment in D and the center of A
In the exemplary embodiment, it is contemplated that,
in an exemplary embodiment, the thermally activated delayed fluorescence material has a singlet-triplet splitting energy Δ Est < 0.15eV.
In an exemplary embodiment, the thermally activated delayed fluorescence material has an inter-inversion cross-over rate k RISC ＞10 5 ·s -1 。
The disclosed embodiment also provides the application of the thermal activation delayed fluorescence material as the luminescent material.
Embodiments of the present disclosure also provide an electroluminescent device comprising a light-emitting layer comprising a thermally activated delayed fluorescence material as described above.
In an exemplary embodiment, the electroluminescent device may further include: an electron blocking layer and a hole blocking layer, and the triplet excited state energy of the material of the electron blocking layer and the triplet excited state energy of the material of the hole blocking layer are both higher than the triplet excited state energy of the light emitting material.
The embodiment of the disclosure also provides a display device, which comprises the electroluminescent device.
Additional features and advantages of the disclosure will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by the practice of the disclosure. Other advantages of the disclosure may be realized and attained by the instrumentalities and combinations particularly pointed out in the specification and the drawings.
Drawings
The accompanying drawings are included to provide an understanding of the disclosed embodiments and are incorporated in and constitute a part of this specification, illustrate embodiments of the disclosure and together with the example serve to explain the principles of the disclosure and not to limit the disclosure.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an exemplary embodiment of the present disclosure;
FIG. 2 is a single crystal structural view of Compound A2.
The reference symbols in the drawings have the following meanings:
100-a cathode; 200-a hole injection layer; 300-hole transport layer; 400-an electron blocking layer; 500-a light emitting layer; 600-a hole blocking layer; 700-electron transport layer; 800-electron injection layer; 900-cathode; 1000-a cover layer; 1100-encapsulation layer.
Detailed Description
To make the objects, technical solutions and advantages of the present application more apparent, embodiments of the present application will be described in detail below with reference to the accompanying drawings. It should be noted that the embodiments and features of the embodiments in the present application may be arbitrarily combined with each other without conflict.
The embodiments herein may be embodied in many different forms. Those skilled in the art can readily appreciate the fact that the present implementations and teachings can be modified into a variety of forms without departing from the spirit and scope of the present disclosure. Therefore, the present disclosure should not be construed as being limited to the contents described in the following embodiments. The embodiments and features of the embodiments in the present disclosure may be arbitrarily combined with each other without conflict.
In the drawings, the size of constituent elements, the thickness of layers, or regions may be exaggerated for clarity. Thus, any one implementation of the present disclosure is not necessarily limited to the dimensions shown in the figures, and the shapes and sizes of the components in the figures are not intended to reflect actual proportions. Further, the drawings schematically show ideal examples, and any one implementation of the present disclosure is not limited to the shapes, numerical values, or the like shown in the drawings.
The disclosed embodiments provide a thermally activated delayed fluorescence material having a D-L-a structure as shown in formula I:
wherein, L is any one of substituted or unsubstituted arylene, heteroarylene, norbornenyl, polynorbornenyl and triptycenyl; here, substituted arylene, substituted heteroarylene, substituted naphthylene, substituted phenanthrylene, substituted dibenzothiophenylene, substituted dibenzofuranylene, substituted carbazolyl, substituted fluorenylene, substituted spirofluorenylene, substituted norbornenyl, substituted polynorbornenyl, substituted triptycenyl, substituted acenaphthylene are substituted with one or more of the following groups: aryl, heteroaryl, naphthyl, phenanthryl, dibenzothienyl, dibenzofuranyl, carbazolyl, fluorenyl, spirofluorenyl, norbornenyl, polynorbornenyl, triptycenyl, acenaphthylenyl;
d is a group which can provide charge and has donor properties, and is any one of substituted C3 to C60 monocyclic heteroaryl, substituted C3 to C60 fused ring heteroaryl, substituted C6 to C60 monocyclic aryl and substituted C9 to C60 fused ring aryl; here, substituted C3 to C60 monocyclic heteroaryl, substituted C3 to C60 fused ring heteroaryl means substituted with one or more of the following groups: monocyclic heteroaryl of C3 to C60, fused ring heteroaryl of C3 to C60, monocyclic aryl of C6 to C60, fused ring aryl of C9 to C60, substituted amine; substituted C6 to C60 monocyclic aryl, substituted C9 to C60 fused ring aryl means substituted with one or more of the following groups: monocyclic heteroaryl of C3 to C60, fused ring heteroaryl of C3 to C60, substituted amine; substituted amine groups are meant to be substituted with one or more of the following groups: substituted C6 to C60 monocyclic aryl, substituted C6 to C60 monocyclic arylene, substituted C9 to C60 fused ring aryl, substituted C9 to C60 fused ring arylene, wherein substituted C6 to C60 monocyclic aryl, substituted C6 to C60 monocyclic arylene, substituted C9 to C60 fused ring aryl, substituted C9 to C60 fused ring arylene means substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C60 monocyclic aryl, C9 to C60 fused ring aryl;
a is a group with acceptor properties capable of accepting the charge provided by D.
In exemplary embodiments, L and D, a may be connected by a single bond or may be connected by sharing an atom (e.g., carbon atom) (e.g., compounds A3, A4, A5).
In exemplary embodiments, D is any one of the groups represented by formula II-1, formula II-2, formula II-3:
in formula II-1, Z1 is any one of C, N, O, S, P, B and Se, R1 to R4 are each independently any one of hydrogen, deuterium, C1 to C12 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C3 to C30 heteroaryl, and substituted or unsubstituted C3 to C30 heteroarylene; r5 is any one of a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heteroaryl group, and a substituted or unsubstituted C3 to C30 heteroarylene group; here, substituted C6 to C30 aryl, substituted C6 to C30 arylene, substituted C3 to C30 heteroaryl, substituted C3 to C30 heteroarylene means substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C30 aryl, C3 to C30 heteroaryl; ar1 is combined on the benzo five-membered ring in a substituted or fused manner, and Ar1 is any one of substituted or unsubstituted C6-C20 aryl, arylene, heteroaryl, heteroarylene, biphenyl and naphthyl; here, substituted C6 to C20 aryl, substituted C6 to C20 arylene, substituted C6 to C20 heteroaryl, substituted C6 to C20 heteroarylene, substituted biphenyl, substituted naphthalene means substituted with one or more of the following groups: c6 to C20 aryl, C6 to C20 heteroaryl, biphenyl, naphthyl; and when Z1 is C, at least one of R1 to R5 and Ar1 contains a heteroaryl or heteroarylene group;
in formula II-2, Z2 is any one of C, N, O, S, P, B and Se, R6 to R13, R15 and R16 are each independently any one of hydrogen, deuterium, C1 to C12 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C6 to C30 arylene and substituted or unsubstituted C3 to C30 heteroarylene; r14 is substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C3 to C30 heteroarylene; here, substituted C6 to C30 aryl, substituted C3 to C30 heteroaryl, substituted C6 to C30 arylene, substituted C3 to C30 heteroarylene means substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C30 aryl, C3 to C30 heteroaryl; and when Z2 is C, at least one of R6 to R16 contains a heteroaryl or heteroarylene group;
in formula II-3, ar2, ar23, ar4 are each independently any one of hydrogen, deuterium, a C1 to C12 alkyl group, a substituted C6 to C60 monocyclic aryl group, a substituted C6 to C60 monocyclic arylene group, a substituted C9 to C60 fused ring aryl group, a substituted C9 to C60 fused ring arylene group, and at least one of Ar2, ar23, ar4 is a substituted C6 to C60 monocyclic aryl group, a substituted C6 to C60 monocyclic arylene group, a substituted C9 to C60 fused ring aryl group, or a substituted C9 to C60 fused ring arylene group; here, the substituted C6 to C60 monocyclic aryl group, the substituted C6 to C60 monocyclic arylene group, the substituted C9 to C60 fused ring aryl group, the substituted C9 to C60 fused ring arylene group means being substituted with one or more of the following groups: hydrogen, deuterium, C1 to C12 alkyl, C6 to C60 monocyclic aryl, C9 to C60 fused ring aryl.
Generally, TADF materials exhibit a distorted thermally-activated delayed fluorescence-acceptor structure. Partial segments of the donor and the acceptor of the TADF material of the embodiments of the present disclosure are arranged face to face, which can achieve space charge transfer and space separation effects, and can enhance the light emission performance of the TADF material. The donor D and acceptor A are connected by a rigid linker L, which can be confined to a close-packed coplanar structure. The conjugate interruption can avoid large frequency shift of the emission spectrum, which is beneficial to blue light emission; moreover, partial fragments of the donor and the acceptor are arranged in a face-to-face mode, so that electron cloud overlapping between the donor and the acceptor can be reduced, delta Est of the TADF material can be reduced, a RISC process is promoted, and a TADF effect is realized.
In embodiments of the present disclosure, the aryl group includes, but is not limited to, phenyl, naphthyl, anthracenyl, acenaphthenyl, indenyl, phenanthryl, azulenyl, pyrenyl, fluorenyl, peryleneyl, spirofluorenyl, spirobifluorenyl,
phenyl, benzophenanthryl, benzanthryl, fluoranthryl, picene, tetracene, and indacenyl.
The term "hetero" as used in heteroarylene, heteroaryl means that at least one carbon atom in the aromatic ring is substituted with a heteroatom selected from any one or more of a nitrogen atom (N), an oxygen atom (O), a sulfur atom (S), a phosphorus atom (P), a boron atom (B), and a selenium (Se) atom.
In embodiments of the present disclosure, the heteroaryl group includes, but is not limited to, benzoxazolyl, benzothiazolyl, indolyl, benzimidazolyl, pyrrolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, carbazolyl, thienyl, thiazolyl, benzocarbazolyl, dibenzocarbazolyl, indobenzocarbazolyl, indenocarbazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl, phthalazinyl, benzoquinolinyl, benzisoquinolinyl, benzoquinazolinyl, benzoquinoxalinyl, acridinyl, phenanthrolinyl, furanyl, pyranyl, oxazinyl, oxazolyl, oxadiazolyl (oxazolyl), triazolyl, dioxanyl (dioxanyl), benzofuranyl, dibenzofuranyl, dibenzothiophenyl, thiazinyl, thiophenyl, and N-substituted spirofluorenyl.
In an exemplary embodiment, L may be any one of a norbornenyl group, a fluorenylidene group, a naphthylidene group, and an acenaphthylene group.
In exemplary embodiments, D may be any one of a substituted C3 to C60 monocyclic heteroaryl group containing at least one nitrogen atom, a substituted C3 to C60 fused ring heteroaryl group containing at least one nitrogen atom, and the heteroatoms in the monocyclic heteroaryl group, the fused ring heteroaryl group further include at least one of an oxygen atom, a sulfur atom, and a selenium atom.
In exemplary embodiments, D may be any one of the following groups:
in exemplary embodiments, a may be a group containing a triazine structure.
In exemplary embodiments, a may be any one of the following groups:
in an exemplary embodiment, the thermally activated delayed fluorescence material may be any one of the following compounds:
in an exemplary embodiment, D and A are both connected on the same side of L, and the plane of the segment in D and the plane of A present a face-to-face alignment with an angle of inclination, θ, wherein 5 ° < θ < 50 °.
In an exemplary embodiment, 10 ° < θ < 30 °, for example, θ may be 11 °,15 °, 20 °, 25 °, 29 °.
In an exemplary embodiment, the distance between the center of the segment in D and the center of A
In the exemplary embodiment, it is contemplated that,
for example, d can be { [ MEANS ]>
The TADF material of the embodiments of the present disclosure can overcome the problem of non-uniform D-a distance of the emitter.
In an exemplary embodiment, the thermally activated delayed fluorescence material has a singlet-triplet splitting energy Δ Est < 0.15eV.
In an exemplary embodiment, the thermally activated delayed fluorescence material has an intersystem crossing rate k RISC ＞10 5 ·s -1 。
In the description of the present disclosure, a thermally activated delayed fluorescence material may be understood as the use of the compound represented by formula I, and the present disclosure provides a novel use of the compound represented by formula I as a thermally activated delayed fluorescence material.
The disclosed embodiment also provides the application of the thermal activation delayed fluorescence material as the luminescent material.
Embodiments of the present disclosure also provide a light emitting layer material including a host material and a guest light emitting material including the thermally activated delayed fluorescence material as described above.
In an exemplary embodiment, the thermally activated delayed fluorescence material may be included in the light emitting layer material in an amount of 0.1 to 50% by weight.
In an exemplary embodiment, the host material may include any one or more of a single host, a co-host, and an exciplex material.
In an exemplary embodiment, the host material has a highest occupied molecular orbital energy level HOMO | > 5.5eV.
Embodiments also provide an electroluminescent device including a light emitting layer including the thermally activated delayed fluorescence material as described above.
In an exemplary embodiment, the electroluminescent device may further include: an electron blocking layer and a hole blocking layer, and the triplet excited state energy T1 of the material of the electron blocking layer and the material of the hole blocking layer are both higher than the triplet excited state energy T1 of the light emitting material. At this time, confinement of excitons in the TADF emitter is facilitated.
In an exemplary embodiment, the electroluminescent device may include: an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a light Emitting Layer (EML), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), a cathode, a Capping Layer (CPL), and an encapsulation Layer, which are disposed on the substrate.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an exemplary embodiment of the present disclosure. As shown in fig. 1, the electroluminescent device may include: an anode 100, a hole injection layer 200, a hole transport layer 300, an electron blocking layer 400, a light emitting layer 500, a hole blocking layer 600, an electron transport layer 700, an electron injection layer 800, a cathode 900, and an encapsulation layer 1000 disposed on a substrate. The hole injection layer 200 is disposed on a surface of the anode 100 side, the hole transport layer 300 is disposed on a surface of the hole injection layer 200 on a side away from the anode 100, the electron blocking layer 400 is disposed on a surface of the hole transport layer 300 on a side away from the anode 100, the light emitting layer 500 is disposed on a surface of the electron blocking layer 400 on a side away from the anode 100, the hole blocking layer 600 is disposed on a surface of the light emitting layer 500 on a side away from the anode 100, the electron transport layer 700 is disposed on a surface of the hole blocking layer 600 on a side away from the anode 100, the electron injection layer 800 is disposed on a surface of the electron transport layer 700 on a side away from the anode 100, the cathode 900 is disposed on a surface of the electron injection layer 800 on a side away from the anode 100, the capping layer 1000 is disposed on a surface of the cathode 900 on a side away from the anode 100, and the encapsulation layer 1100 is disposed on a surface of the capping layer 1000 on a side away from the anode 100.
In an exemplary embodiment, the anode may be a material having a high work function. For example, for a bottom emission device, a transparent Oxide material such as Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) may be used for the anode. Alternatively, for a top emission device, the anode may be a composite structure of metal and transparent Oxide, such as Ag/ITO (Indium Tin Oxide), ag/IZO (Indium Zinc Oxide), al/ITO, al/IZO, or ITO/Ag/ITO, which can ensure good reflectivity.
In an exemplary embodiment, the material of the hole injection layer may include a transition metal oxide, for example, any one or more of molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
In another exemplary embodiment, the material of the hole injection layer may include a p-type dopant of a strong electron-withdrawing system and a hole transport material;
the p-type dopant may include any one or more of 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene, 2,3,5, 6-tetrafluoro-7, 7', 8' -tetracyano-p-benzoquinone (F4 TCNQ), 1,2, 3-tris [ (cyano) (4-cyano-2, 3,5, 6-tetrafluorophenyl) methylene ] cyclopropane;
the hole transport material can comprise any one or more of arylamine hole transport materials, dimethyl fluorene hole transport materials and carbazole hole transport materials; for example, the hole transport material may include any one or more of 4,4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N' -bis (3-methylphenyl) -N, N '-diphenyl- [1,1' -biphenyl ] -4,4 '-diamine (TPD), 4-phenyl-4' - (9-phenylfluoren-9-yl) triphenylamine (BAFLP), 4 '-bis [ N- (9, 9-dimethylfluoren-2-yl) -N-phenylamino ] biphenyl (lddfpbi), 4' -bis (9-Carbazolyl) Biphenyl (CBP), and 9-phenyl-3- [4- (10-phenyl-9-anthracenyl) phenyl ] -9H-carbazole (PCzPA).
In an exemplary embodiment, the hole transport layer may be formed by evaporation.
In an exemplary embodiment, the material of the electron blocking layer may include any one or more of an arylamine-based electron blocking material, a dimethylfluorene-based electron blocking material, and a carbazole-based electron blocking material; for example, the material of the electron blocking layer may include any one or more of 4,4 '-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), N' -bis (3-methylphenyl) -N, N '-diphenyl- [1,1' -biphenyl ] -4,4 '-diamine (TPD), 4-phenyl-4' - (9-phenylfluoren-9-yl) triphenylamine (BAFLP), 4 '-bis [ N- (9, 9-dimethylfluoren-2-yl) -N-phenylamino ] biphenyl (DFLDPBi), 4' -bis (9-Carbazolyl) Biphenyl (CBP), and 9-phenyl-3- [4- (10-phenyl-9-anthracenyl) phenyl ] -9H-carbazole (PCzPA).
In an exemplary embodiment, the electron blocking layer may be formed by evaporation.
In an exemplary embodiment, the light emitting layer may be formed by evaporation.
In an exemplary embodiment, the material of the hole blocking layer may include an aromatic heterocyclic-based hole blocking material, and for example, may include any one or more of a benzimidazole derivative-based hole blocking material, an imidazopyridine derivative-based hole blocking material, a benzimidazole phenanthridine derivative-based hole blocking material, a pyrimidine derivative-based hole blocking material, a triazine derivative-based hole blocking material, a quinoline derivative-based hole blocking material, an isoquinoline derivative-based hole blocking material, and a phenanthroline derivative-based hole blocking material.
For another example, the hole blocking layer material may include any one or more of 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (PBD), 1, 3-bis [5- (p-tert-butylphenyl) -1,3, 4-oxadiazol-2-yl ] benzene (OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4-biphenyl) -1,2, 4-Triazole (TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenyl) -1,2, 4-triazole (p-etaz), bathophenanthroline (BPhen), (BCP), 4' -bis (5-methylbenzoxazol-2-yl) stilbene (BzOs).
In an exemplary embodiment, the hole blocking layer may be formed by evaporation.
In an exemplary embodiment, the material of the electron transport layer may include an aromatic heterocyclic-based electron transport material, and for example, may include any one or more of a benzimidazole derivative-based electron transport material, an imidazopyridine derivative-based electron transport material, a benzimidazole phenanthridine derivative-based electron transport material, a pyrimidine derivative-based electron transport material, a triazine derivative-based electron transport material, a quinoline derivative-based electron transport material, an isoquinoline derivative-based electron transport material, and a phenanthroline derivative-based electron transport material.
As another example, the material of the electron transport layer may include any one or more of 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (PBD), 1, 3-bis [5- (p-tert-butylphenyl) -1,3, 4-oxadiazol-2-yl ] benzene (OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4-biphenyl) -1,2, 4-Triazole (TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenyl) -1,2, 4-triazole (p-etaz), bathophenanthroline (BPhen), (BCP), 4' -bis (5-methylbenzoxazol-2-yl) stilbene (BzOs).
In an exemplary embodiment, the electron transport layer may be formed by evaporation.
In an exemplary embodiment, the material of the electron injection layer may include any one or more of an alkali metal electron injection material and a metal electron injection material.
For example, the electron injection layer material may include any one or more of LiF, yb, mg, ca.
In an exemplary embodiment, the electron injection layer may be formed by evaporation.
In exemplary embodiments, the cathode may be formed using a metal having a relatively low work function, such as Al, ag, mg, or the like, or an alloy containing a metal material having a low work function.
In an exemplary embodiment, the cover layer may be formed by evaporation using an organic small molecule material having a refractive index greater than 1.8.
In an exemplary embodiment, the Encapsulation layer may be a glass UV Encapsulation layer, and may also be a Thin-Film Encapsulation (TFE) layer.
The embodiment of the disclosure also provides a display device, which comprises the electroluminescent device.
In an exemplary embodiment, the display apparatus may include a plurality of the electroluminescent devices. For example, the electroluminescent device may be a blue electroluminescent device, a green electroluminescent device, or a red electroluminescent device, and the display apparatus may include a blue electroluminescent device, a green electroluminescent device, and a red electroluminescent device.
The display device can be any product or component with a display function, such as a mobile phone, a tablet computer, a television, a display, a notebook computer, a digital photo frame, a navigator, a vehicle-mounted display, an intelligent watch and an intelligent bracelet.
The following are the fabrication procedures and performance tests and comparisons of electroluminescent devices of some exemplary embodiments of the present disclosure.
Example 1
(1) Under a vacuum of 1X 10 -5 Depositing an Ag/ITO (90 nm/10 nm) film on a glass substrate by a vacuum evaporation method under the condition of Pa to form an anode;
(2) Forming a Hole Injection Layer (HIL) on the anode by evaporation;
(3) Forming a Hole Transport Layer (HTL) on the Hole Injection Layer (HIL) by evaporation;
(4) Forming an Electron Blocking Layer (EBL) on the Hole Transport Layer (HTL) by evaporation;
(5) Co-evaporating a compound H and a compound A2 on the Electron Blocking Layer (EBL) to form an emitting layer (EML) with a thickness of 30 nm; wherein, the weight percentage content of the compound H in the luminescent layer is 95 percent, and the weight percentage content of the compound A2 is 5 percent;
(6) Forming a Hole Blocking Layer (HBL) on the luminescent layer (EML) by evaporation;
(7) Forming an Electron Transport Layer (ETL) on the Hole Blocking Layer (HBL) by evaporation;
(8) Evaporating a Liq film on the Electron Transport Layer (ETL) to form an Electron Injection Layer (EIL) with the thickness of 1 nm;
(9) A metal Mg: ag (weight ratio of 9: 1) film was evaporated on the Liq film to form a metal cathode having a thickness of 15 nm;
(10) A capping layer (CPL) was deposited on the metal cathode to a thickness of 60 nm.
Example 2
(1) Under vacuum of 1X 10 -5 Depositing an Ag/ITO (90 nm/10 nm) film on a glass substrate by a vacuum evaporation method under the condition of Pa to form an anode;
(2) Forming a Hole Injection Layer (HIL) on the anode by evaporation;
(3) Forming a Hole Transport Layer (HTL) on the Hole Injection Layer (HIL) by evaporation;
(4) Forming an Electron Blocking Layer (EBL) on the Hole Transport Layer (HTL) by evaporation;
(5) Co-evaporating a compound H and a compound A5 on the Electron Blocking Layer (EBL) to form an emitting layer (EML) with the thickness of 30 nm; wherein, the weight percentage content of the compound H in the luminescent layer is 80 percent, and the weight percentage content of the compound A5 is 20 percent;
(6) Forming a Hole Blocking Layer (HBL) on the luminescent layer (EML) by evaporation;
(7) Forming an Electron Transport Layer (ETL) on the Hole Blocking Layer (HBL) by evaporation;
(8) Evaporating a Liq film on the Electron Transport Layer (ETL) to form an Electron Injection Layer (EIL) with the thickness of 1 nm;
(9) A metal Mg: ag (weight ratio of 9: 1) film was evaporated on the Liq film to form a metal cathode having a thickness of 15 nm;
(10) A capping layer (CPL) was deposited on the metal cathode to a thickness of 60 nm.
Comparative example 1
(1) Under vacuum of 1X 10 -5 Depositing an Ag/ITO (90 nm/10 nm) film on a glass substrate by a vacuum evaporation method under the condition of Pa to form an anode;
(2) Forming a Hole Injection Layer (HIL) on the anode by evaporation;
(3) Forming a Hole Transport Layer (HTL) on the Hole Injection Layer (HIL) by evaporation;
(4) Forming an Electron Blocking Layer (EBL) on the Hole Transport Layer (HTL) by evaporation;
(5) Co-evaporating a compound H and a compound B1 on the Electron Blocking Layer (EBL) to form an emitting layer (EML) with the thickness of 30 nm; wherein, the weight percentage content of the compound H in the luminescent layer is 90 percent, and the weight percentage content of the compound B is 20 percent;
(6) Forming a Hole Blocking Layer (HBL) on the luminescent layer (EML) by evaporation;
(7) Forming an Electron Transport Layer (ETL) on the Hole Blocking Layer (HBL) by evaporation;
(8) Evaporating a Liq film on the Electron Transport Layer (ETL) to form an Electron Injection Layer (EIL) with the thickness of 1 nm;
(9) A metal Mg: ag (weight ratio of 9: 1) film was evaporated on the Liq film to form a metal cathode having a thickness of 15 nm;
(10) A capping layer (CPL) was vapor-deposited on the metal cathode to a thickness of 60 nm.
The compound H is a host material in the luminescent layer, the compounds A2, A5 and B1 are three different materials with TADF characteristics, and the chemical structures of the compounds H, A2, A5 and B1 are as follows:
synthesis of Compound A2
Under argon atmosphere, 2, 4-diphenyl-6- [4- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl]-1,3, 5-triazine (8.5g, 19.5mmol), 9- (4-iodophenyl) -carbazole (5.5g, 15.0 mmol), potassium carbonate (5.4g, 39.0 mmol) and 2, 5-norbornadiene (6.1mL, 60.0 mmol) were added to a mixture consisting of tetrahydrofuran THF (80 mL) and water (40 mL) and heated to 60 ℃. Pd (OAc) in dry THF (6 mL) was then added 2 (0.13g, 0.60mmol) and triphenylphosphine PPh3 (0.39g, 1.50mmol) were added to the reaction mixture and stirred at 60 ℃ for 24 h. After cooling to room temperature, the mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography (eluent cyclohexane: dichloromethane = 8. The solid was then recrystallized from a mixture of dichloromethane and cyclohexane (1/7, v/v) to give compound A2 in 55% overall yield (5.3 g).
Synthesis of Compound A5
Under a nitrogen atmosphere, 3, 5-bis (9, 9-dimethylfluorenyl) -1-chlorotriazine (4.25 mmol), a solution of 9, 9-diphenyl-9H-fluoren-2-ylboronic acid (5.52 mmol) and CsF (12.74 mmol) were added to 10To 0ml of an anhydrous toluene solution, pd (PPh 3) was added 4 (0.21 mmol) and heated at 90 ℃ for 12h. After the mixture was cooled, it was diluted with dichloromethane (300 mL), the salts were washed off with water (200 mL), and the aqueous layer was extracted with dichloromethane. After removal of the solvent under vacuum, the crude product was purified by silica gel column chromatography (hexane: dichloromethane = 7. After column separation, the product was dissolved in THF, and the mixture solution was mixed with a 10 mass% aqueous NaOH solution. The mixture solution was refluxed for 1 hour. After cooling, dichloromethane was added to the solution and washed with water. After removal of the organic solvent, compound A5 is obtained.
FIG. 2 is a single crystal structural view of Compound A2. As can be seen from FIG. 2, compound A2 is of the structure D-L-A, both D and A are attached to the same side of L, and fragment D-1 in D is in face-to-face alignment with A.
The properties of some of the materials used in the electroluminescent device are shown in table 1. Where the T1 data is from the phosphorescence spectrum at 77K.
TABLE 1
It can be seen that both compounds A2, A5 have a Δ Est of less than 0.15eV and an inter-system cross-over rate k RISC Are all greater than 10 5 ·s -1 Δ Est and k RISC The value of (a) is appropriate, so whether the balance among the delta Est, the oscillator strength (f) and the non-radiative decay can be obtained; the distance between D and A (i.e. the distance between the center of the segment D-1 in D and the center of A) D is all within the range
To/is>
Within the range of D-A dihedral angles (i.e. the angle of inclination between the plane of segment D-1 in D and the plane of A) theta are all 10 DEG toIn the range of 30 deg. and has a triplet excited state energy T1 less than T1 of the HBL and EBL materials.
The properties of the electroluminescent device are shown in table 2.
TABLE 2
It can be seen that the efficiency of the electroluminescent device of the embodiments of the present disclosure is significantly higher than that of the comparative example.
Although the embodiments disclosed in the present disclosure are described above, the descriptions are only for the convenience of understanding the present disclosure, and are not intended to limit the present disclosure. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the disclosure, and that the scope of the disclosure is to be limited only by the terms of the appended claims.
Claims (5)
1. A thermally activated delayed fluorescence material is characterized by comprising the following compounds:
compound A6
2. Use of a thermally activated delayed fluorescence material according to claim 1 as a luminescent material.
3. An electroluminescent device comprising a light-emitting layer comprising the thermally activated delayed fluorescence material according to claim 1.
4. The electroluminescent device of claim 3, further comprising: an electron blocking layer and a hole blocking layer, and both the triplet excited state energy of the material of the electron blocking layer and the triplet excited state energy of the material of the hole blocking layer are higher than the triplet excited state energy of the material of the light emitting layer.
5. A display device comprising an electroluminescent device according to claim 3 or 4.
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