Organic electroluminescent device
Patent Information
- Application Number
- CN202180064334.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2021-07-20
- Filing Date
- 2021-09-17
- Publication Date
- 2026-10-30
- Estimated Expiration
- 2041-09-17
AI Technical Summary
然而,这些方法仍然没有提供结合所有上述期望特征(即:良好的效率、长寿命和良好的色纯度)的有机电致发光器件
Smart Images

Figure QLYQS_1 
Figure QLYQS_2 
Figure QLYQS_3
Abstract
Description
Technical Field
[0001] This invention relates to organic electroluminescent devices comprising one or more light-emitting layers B, each of the one or more light-emitting layers B comprising one or more sublayers, wherein the one or more sublayers of each light-emitting layer B as a whole comprise at least one host material H. B At least one phosphorescent material P B At least one small FWHM emitter S B and optionally at least one TADF material E B , wherein at least one S B (Preferably, each S) B It emits light having a full width at half maximum (FWHM) of less than or equal to 0.25 eV. Furthermore, the present invention relates to a method for generating light by means of an organic electroluminescent device according to the invention. Background Technology
[0002] Organic electroluminescent devices (OLEDs), which incorporate one or more organic-based light-emitting layers (such as organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors), are gaining increasing importance. Specifically, OLEDs are promising devices for electronic products, such as screens, displays, and lighting devices. Unlike most electroluminescent devices that are essentially inorganic, organic-based OLEDs are generally quite flexible and can be fabricated as particularly thin layers. Currently available OLED screens and displays exhibit good efficiency and long lifespan, or good color purity and long lifespan, but none combine all three properties (i.e., good efficiency, long lifespan, and good color purity).
[0003] The color purity, or color point, of an OLED is typically provided by CIEx and CIEy coordinates, while the color gamut for next-generation displays is provided by so-called BT-2020 and DCPI3 values. Generally, to achieve these color coordinates, a top-emitting device is needed to adjust the color coordinates by changing the cavity. To achieve high efficiency in a top-emitting device while targeting these color gamuts, a narrow emission spectrum in a bottom-emitting device is required.
[0004] Existing phosphorescent emitters exhibit a fairly broad emission spectrum, typically greater than 0.25 eV, in the broad emission of phosphorescent OLEDs (PHOLEDs). The broad emission spectrum of PHOLEDs in bottom-emitting devices leads to a high loss of external coupling efficiency for top-emitting device structures while targeting the BT-2020 and DCPI3 color gamuts.
[0005] Furthermore, phosphorescent materials are typically based on transition metals such as iridium. Due to their generally low abundance, transition metals are quite expensive materials within OLED stacks. Therefore, transition metal-based materials have the greatest potential for reducing OLED costs. Consequently, reducing the amount of transition metals within OLED stacks is a key performance indicator for pricing OLED applications.
[0006] Recently, some fluorescent or thermally activated delayed fluorescence (TADF) emitters have been developed that exhibit fairly narrow emission spectra, typically with a free wave size (FWHM) of less than or equal to 0.25 eV, making them more suitable for achieving the BT-2020 and DCPI3 color gamuts. However, such fluorescent and TADF emitters generally suffer from low efficiency due to reduced efficiency at higher brightness (i.e., the roll-off behavior of OLEDs) and low lifetime due to, for example, exciton-polaron annihilation or exciton-exciton annihilation.
[0007] These drawbacks can be overcome to some extent by applying so-called super-methods. The latter relies on energy pumps that transfer energy to a fluorescent emitter that preferably exhibits the narrow emission spectrum described above. The energy pump can be, for example, a TADF material exhibiting reverse intersystem crossing (RISC) or a transition metal complex exhibiting effective intersystem crossing (ISC). However, these methods still do not provide an organic electroluminescent device that combines all the aforementioned desired characteristics (i.e., good efficiency, long lifetime, and good color purity).
[0008] The central element of an organic electroluminescent device used to generate light is typically at least one light-emitting layer placed between the anode and the cathode. When voltage (and current) are applied to the organic electroluminescent device, holes and electrons are injected from the anode and cathode, respectively. Summary of the Invention
[0009] Typically, a hole transport layer is located between the emitting layer and the anode, and an electron transport layer is typically located between the emitting layer and the cathode. These different layers are arranged sequentially. High-energy excitons are then generated through recombination of holes and electrons in the emitting layer. The decay of this excited state (e.g., a singlet state such as S1 and / or a triplet state such as T1) to the ground state (S0) presumptuously results in the emission of light.
[0010] Surprisingly, it has been found that the emissive layer of an organic electroluminescent device, consisting of one or more layers including phosphorescent materials, small half-peak full width (FWHM) emitters, host materials, and optionally TADF materials, provides an ideal organic electroluminescent device with long lifetime, high quantum yield, and narrow emission for achieving the BT-2020 and DCPI3 color gamuts.
[0011] Here, phosphorescent materials and / or optionally TADF materials can transfer energy to a small half-peak full width (FWHM) emitter for displaying light emission.
[0012] This invention relates to an organic electroluminescent device comprising at least one light-emitting layer B composed of one or more sublayers, wherein the one or more sublayers are adjacent to each other and, as a whole, comprise the following components:
[0013] (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0014] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0015] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and optionally...
[0016] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ),
[0017] One or more sublayers located on the outer surface of the light-emitting layer B contain materials selected from phosphorescent material P. B Small FWHM emitter S B and TADF material E B At least one (emitter) material in the group.
[0018] One aspect of the present invention relates to an organic electroluminescent device comprising at least one light-emitting layer B containing one or more sublayers, wherein the one or more sublayers are adjacent to each other and, as a whole, comprise the following components:
[0019] (i) Main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0020] (ii) Phosphorescent materials P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0021] (iii) Small half-peak full width (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and optionally...
[0022] (iv) Thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(S1) E ),
[0023] One or more sublayers located on the outer surface of the light-emitting layer B contain materials selected from phosphorescent material P. B Small FWHM emitter S B and TADF material E B At least one (emitter) material in the group.
[0024] In one embodiment of the present invention, at least one of one or more sublayers of at least one light-emitting layer B comprises the following components:
[0025] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ).
[0026] In one embodiment of the invention, the organic electroluminescent device includes at least one light-emitting layer B composed of one or more sublayers, wherein the one or more sublayers of the light-emitting layer B include the following components:
[0027] (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0028] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P) and the lowest excited triplet energy level E(T1) P );and
[0029] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and optionally...
[0030] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ).
[0031] In one embodiment of the invention, the organic electroluminescent device includes at least one light-emitting layer B composed of one or more sublayers, wherein the one or more sublayers of the light-emitting layer B include the following components:
[0032] (i) Main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0033] (ii) Phosphorescent materials P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0034] (iii) Small half-peak full width (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0035] (iv) Thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ).
[0036] In one embodiment of the invention, the organic electroluminescent device includes at least one light-emitting layer B composed of one or more sublayers, wherein the one or more sublayers of the light-emitting layer B include the following components:
[0037] (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0038] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0039] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0040] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ).
[0041] In one embodiment of the invention, the organic electroluminescent device includes at least one light-emitting layer B, said at least one light-emitting layer B comprising the following components:
[0042] (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0043] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0044] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0045] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ).
[0046] In one embodiment of the invention, the organic electroluminescent device includes a light-emitting layer B consisting of exactly one layer, said light-emitting layer B comprising the following components:
[0047] (i) Main material H B ;and
[0048] (ii) Phosphorescent materials P B ;and
[0049] (iii) Small half-peak full width (FWHM) emitter S B ; and optionally
[0050] (iv) TADF material E B .
[0051] In a preferred embodiment, the organic electroluminescent device includes a light-emitting layer B consisting of exactly one layer, said light-emitting layer B comprising the following components:
[0052] (i) at least one main material H B ;and
[0053] (ii) at least one phosphorescent material P B ;and
[0054] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B ;as well as
[0055] (iv) At least one thermally activated delayed fluorescence (TADF) material E B . Detailed Implementation
[0056] Combination of sub-layers
[0057] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B consisting of exactly one (sub)layer. In a preferred embodiment of the invention, each light-emitting layer B in the electroluminescent device according to the invention consists of exactly one (sub)layer. In a preferred embodiment of the invention, the electroluminescent device according to the invention includes exactly one light-emitting layer B consisting of exactly one (sub)layer.
[0058] In another embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of more than one sublayer. In another embodiment of the invention, each light-emitting layer B included in the electroluminescent device according to the invention includes more than one sublayer. In another embodiment of the invention, each light-emitting layer B included in the electroluminescent device according to the invention is composed of more than one sublayer.
[0059] In another embodiment of the invention, the electroluminescent device according to the invention includes exactly one light-emitting layer B composed of more than one sublayer. In another embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of exactly two sublayers.
[0060] In another embodiment of the invention, each light-emitting layer B in the electroluminescent device according to the invention comprises exactly two sublayers. In another embodiment of the invention, the electroluminescent device according to the invention comprises exactly one light-emitting layer B comprising exactly two sublayers.
[0061] In another embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of more than two sublayers. In another embodiment of the invention, each light-emitting layer B included in the electroluminescent device according to the invention comprises more than two sublayers.
[0062] In another embodiment of the invention, the electroluminescent device according to the invention includes exactly one light-emitting layer B consisting of more than two sublayers.
[0063] In one embodiment of the invention, each light-emitting layer B of the organic electroluminescent device according to the invention includes exactly one, exactly two, or exactly three sublayers.
[0064] It is understood that the different sublayers of the luminescent layer B do not necessarily all contain the same material or even contain the same material in the same proportion.
[0065] The understanding is that the different sublayers of the luminescent layer B are adjacent to each other.
[0066] In one embodiment of the invention, at least one sublayer comprises exactly one TADF material E B And exactly one phosphorescent material P B .
[0067] In one embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of more than one sublayer, wherein the at least one sublayer does not include TADF material E. B Phosphorescent materials P B or small FWHM emitter S B .
[0068] In one embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes at least one host material H. B Exactly one phosphorescent material P B And exactly one small FWHM emitter S B .
[0069] In one embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes at least one host material H. B Exactly one TADF material E B Exactly one phosphorescent material P B And exactly one small FWHM emitter S B .
[0070] In one embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B Exactly one TADF material E B Exactly one phosphorescent material P B And exactly one small FWHM emitter S B .
[0071] In one embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B Exactly one phosphorescent material P B And exactly one small FWHM emitter S B .
[0072] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B .
[0073] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one TADF material E. B .
[0074] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one phosphorescent material P. B .
[0075] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one small FWHM emitter S. B .
[0076] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B And exactly one TADF material E B .
[0077] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B And exactly one phosphorescent material P B .
[0078] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B And exactly one small FWHM emitter S B .
[0079] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one TADF material E. B And exactly one small FWHM emitter S B .
[0080] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one TADF material E. B And exactly one phosphorescent material P B .
[0081] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one phosphorescent material P. B And exactly one small FWHM emitter S B .
[0082] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B Exactly one TADF material EB And exactly one small FWHM emitter S B .
[0083] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B Exactly one TADF material E B And exactly one phosphorescent material P B .
[0084] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B Exactly one phosphorescent material P B And exactly one small FWHM emitter S B .
[0085] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one phosphorescent material P. B Exactly one TADF material E B And exactly one small FWHM emitter S B .
[0086] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein the at least one sublayer includes exactly one host material H. B Exactly one TADF material E B Exactly one phosphorescent material P B And exactly one small FWHM emitter S B .
[0087] In a preferred embodiment of the invention, the sublayer comprises exactly one TADF material E B And the sublayer (preferably, another sublayer) comprises exactly one phosphorescent material P B And exactly one small FWHM emitter S B .
[0088] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B, said at least one light-emitting layer B comprising three or more sublayers (or composed of three or more sublayers), wherein the first sublayer B1 comprises exactly one TADF material E. B The second sublayer B2 includes exactly one phosphorescent material P BFurthermore, the third sublayer B3 includes exactly one small FWHM emitter S. B .
[0089] It is understood that the sublayers of the luminescent layer B can be manufactured in different orders (e.g., B1-B2-B3, B1-B3-B2, B2-B1-B3, B2-B3-B1, B3-B2-B1, B3-B1-B2) and have one or more different sublayers between them.
[0090] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B, said at least one light-emitting layer B comprising two or more sublayers (or composed of two or more sublayers), wherein the first sublayer B1 comprises exactly one TADF material E. B And exactly one phosphorescent material P B And the second sublayer B2 includes exactly one small FWHM emitter S B .
[0091] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B, said at least one light-emitting layer B comprising two or more sublayers (or composed of two or more sublayers), wherein the first sublayer B1 comprises exactly one TADF material E. B Furthermore, the second sublayer B2 includes exactly one phosphorescent material P. B And exactly one small FWHM emitter S B .
[0092] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B, said at least one light-emitting layer B comprising two or more sublayers (or composed of two or more sublayers), wherein the first sublayer B1 comprises exactly one phosphorescent material P. B And the second sublayer B2 includes exactly one TADF material E B And exactly one small FWHM emitter S B .
[0093] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B, said at least one light-emitting layer B comprising two or more sublayers (or composed of two or more sublayers), wherein the first sublayer B1 includes exactly one small FWHM emitter S. B And the second sublayer B2 includes exactly one TADF material E B And exactly one phosphorescent material P B In a preferred embodiment, sublayers B1 and B2 are (directly) adjacent to each other, in other words, they are (directly) in contact with each other.
[0094] It is understood that the organic electroluminescent device according to the invention may optionally include one or more light-emitting layers that do not meet the requirements given for the light-emitting layer B in the context of the invention. In other words, the organic electroluminescent device according to the invention includes at least one light-emitting layer B as defined herein, and may optionally include one or more additional light-emitting layers to which the requirements given herein for the light-emitting layer B need not apply. In another embodiment of the invention, at least one, but not all, of the light-emitting layers included in the organic electroluminescent device according to the invention is the light-emitting layer B as defined in the specific embodiments of the invention.
[0095] In a preferred embodiment of the invention, each light-emitting layer included in the organic electroluminescent device according to the invention is a light-emitting layer B as defined in a specific embodiment of the invention.
[0096] Composition of (multiple) light-emitting layers (EML) B
[0097] (at least one) main material H B (At least one) phosphorescent material P B and (at least one) small FWHM emitter S B It can be included in organic electroluminescent devices in any amount and in any proportion.
[0098] In a preferred embodiment, (at least one) main material H B (At least one) phosphorescent material P B (At least one) thermally activated delayed fluorescence (TADF) material E B and (at least one) small FWHM emitter S B It can be included in organic electroluminescent devices in any amount and in any proportion.
[0099] In a preferred embodiment of the invention, the electroluminescent device according to the invention comprises at least one light-emitting layer B consisting of one or more sublayers, wherein, by weight, each of the at least one sublayer comprises an emitter S smaller than (at least one) FWHM. B More (at least) of the main materials H B (More specifically: H) P and / or H N and / or H BP ).
[0100] In a preferred embodiment of the invention, the electroluminescent device according to the invention comprises at least one light-emitting layer B consisting of one or more sublayers, wherein, by weight, each of the at least one sublayer comprises more than one phosphorescent material P. B More (at least) of the main materials H B (More specifically: H) P and / or H Nand / or H BP ).
[0101] In a preferred embodiment of the invention, the electroluminescent device according to the invention includes at least one light-emitting layer B composed of one or more sublayers, wherein, by weight, each of the at least one sublayer comprises more than one TADF material E. B More (at least) of the main materials H B (More specifically: H) P and / or H N and / or H BP ).
[0102] In a preferred embodiment of the invention, each of at least one light-emitting layer B in the organic electroluminescent device according to the invention comprises an emitter S with a smaller FWHM than at least one, depending on weight. B At least one TADF material E B .
[0103] In a preferred embodiment, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or consists of) the following components as a whole:
[0104] (i) 30% to 99.8% by weight of one or more main materials H B ;
[0105] (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ;and
[0106] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ; and optionally
[0107] (v) 0% to 69.8% by weight of one or more solvents.
[0108] In a preferred embodiment, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or consists of) the following components as a whole:
[0109] (i) 30% to 99.8% by weight (preferably 60% to 99.8% by weight) of one or more main materials H B ;
[0110] (ii) 0.1 wt% to 50 wt% (preferably 0.1 wt% to 30 wt%) of one or more phosphorescent materials P B ;and
[0111] (iii) 0.1% to 20% by weight (preferably 0.1% to 10% by weight) of one or more small FWHM emitters S B ; and optionally
[0112] (v) 0% to 3% by weight of one or more solvents.
[0113] In a preferred embodiment, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or consists of) the following components as a whole:
[0114] (i) 30% to 99.8% by weight of one or more main materials H B ;
[0115] (ii) 0.1% to 20% by weight of one or more phosphorescent materials P B ;and
[0116] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ; and optionally
[0117] (v) 0% to 69.8% by weight of one or more solvents.
[0118] In a preferred embodiment, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or consists of) the following components as a whole:
[0119] (i) 30% to 99.8% by weight (preferably 70% to 99.8% by weight) of one or more main materials H B ;
[0120] (ii) 0.1% to 20% by weight of one or more phosphorescent materials P B ;and
[0121] (iii) 0.1% to 50% by weight (preferably 0.1% to 10% by weight) of one or more small FWHM emitters S B ; and optionally
[0122] (v) 0% to 3% by weight of one or more solvents.
[0123] In a preferred embodiment, E BOptionally, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or is composed of) the following components:
[0124] (i) 30% to 99.8% by weight of one or more main materials H B ;
[0125] (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ;and
[0126] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ; and optionally
[0127] (iv) 0% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0128] (v) 0% to 69.8% by weight of one or more solvents.
[0129] In a preferred embodiment, E B Optionally, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or is composed of) the following components:
[0130] (i) 30% to 99.8% by weight of one or more main materials H B ;
[0131] (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ;and
[0132] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ; and optionally
[0133] (iv) 0% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0134] (v) 0% to 3% by weight of one or more solvents.
[0135] In a preferred embodiment, E BOptionally, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or is composed of) the following components:
[0136] (i) 30% to 99.8% by weight of one or more main materials H B ;
[0137] (ii) 0.1% to 20% by weight of one or more phosphorescent materials P B ;and
[0138] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ; and optionally
[0139] (iv) 0% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0140] (v) 0% to 69.8% by weight of one or more solvents.
[0141] In a preferred embodiment, E B Optionally, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or is composed of) the following components:
[0142] (i) 30% to 99.8% by weight of one or more main materials H B ;
[0143] (ii) 0.1% to 20% by weight of one or more phosphorescent materials P B ;and
[0144] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ; and optionally
[0145] (iv) 0% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0146] (v) 0% to 3% by weight of one or more solvents.
[0147] In even more preferred embodiments, wherein E BIt is necessary that, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or is composed of) the following components as a whole:
[0148] (i) 30% to 87.8% by weight of one or more main materials H B ;
[0149] (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ;and
[0150] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;and
[0151] (iv) 12% to 40% by weight of one or more TADF materials E B ; and optionally (v) 0% to 57.8% by weight of one or more solvents.
[0152] In even more preferred embodiments, wherein E B It is necessary that, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or is composed of) the following components as a whole:
[0153] (i) 30% to 87.8% by weight of one or more main materials H B ;
[0154] (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ;and
[0155] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;and
[0156] (iv) 12% to 40% by weight of one or more TADF materials E B ; and optionally (v) 0% to 3% by weight of one or more solvents.
[0157] In even more preferred embodiments, wherein E B It is necessary that, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or is composed of) the following components as a whole:
[0158] (i) 30% to 87.8% by weight of one or more main materials H B (Also known as the host compound H) B );
[0159] (ii) 0.1% to 20% by weight of one or more phosphorescent materials P B ;and
[0160] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;and
[0161] (iv) 12% to 40% by weight of one or more TADF materials E B ; and optionally (v) 0% to 57.8% by weight of one or more solvents.
[0162] In even more preferred embodiments, wherein E B It is necessary that, in the organic electroluminescent device according to the present invention, at least one light-emitting layer B (consisting of or including more than one sub-layer) comprises (or consists of) the following components as a whole:
[0163] (i) 30% to 87.8% by weight of one or more main materials H B (Also known as the host compound H) B );
[0164] (ii) 0.1% to 20% by weight of one or more phosphorescent materials P B ;and
[0165] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;and
[0166] (iv) 12% to 40% by weight of one or more TADF materials E B ; and optionally (v) 0% to 3% by weight of one or more solvents.
[0167] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises less than or equal to 5% by weight of one or more phosphorescent materials P. B .
[0168] In one embodiment of the invention, the organic electroluminescent device includes at least one light-emitting layer B, said at least one light-emitting layer B comprising the following components:
[0169] (i) at least one main material H BIt has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );
[0170] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0171] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0172] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ),
[0173] The relationship represented by the following equations (1) and (2) applies:
[0174] E(T1 H )>E(T1 P (1)
[0175] E(T1 P )>E(S1 S (2), and
[0176] Wherein, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises less than or equal to 5% by weight of one or more phosphorescent materials P. B .
[0177] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0178] (i) 30% to 96.8% by weight of one or more main materials H B (Also known as the host compound H) B );
[0179] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0180] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;
[0181] (iv) 3% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0182] (v) 0% to 66.8% by weight of one or more solvents.
[0183] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0184] (i) 30% to 96.8% by weight of one or more main materials H B (Also known as the host compound H) B );
[0185] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0186] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;
[0187] (iv) 3% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0188] (v) 0% to 3% by weight of one or more solvents.
[0189] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0190] (i) 30% to 89.8% by weight of one or more of the main material H B ;
[0191] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0192] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;
[0193] (iv) 10% to 40% by weight of one or more TADF materials E B ; and optionally (v) 0% to 59.8% by weight of one or more solvents.
[0194] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0195] (i) 30% to 89.8% by weight of one or more main materials H B ;
[0196] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0197] (iii) 0.1% to 10% by weight of one or more small FWHM emitters S B ;
[0198] (iv) 10% to 52% by weight of one or more TADF materials E B ; and optionally (v) 0% to 3% by weight of one or more solvents.
[0199] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0200] (i) 30% to 96.8% by weight of one or more main materials H B ;
[0201] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0202] (iii) 0.1% to 5% by weight of one or more small FWHM emitters S B ;
[0203] (iv) 3% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0204] (v) 0% to 66.8% by weight of one or more solvents.
[0205] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0206] (i) 30% to 96.8% by weight of one or more main materials H B ;
[0207] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0208] (iii) 0.1% to 5% by weight of one or more small FWHM emitters S B ;
[0209] (iv) 3% to 69.8% by weight of one or more TADF materials E B ; and optionally
[0210] (v) 0% to 3% by weight of one or more solvents.
[0211] In a particularly preferred embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0212] (i) 30% to 87.8% by weight of one or more main materials H B ;
[0213] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0214] (iii) 0.1% to 5% by weight of one or more small FWHM emitters S B ;
[0215] (iv) 12% to 40% by weight of one or more TADF materials E B ; and optionally (v) 0% to 57.8% by weight of one or more solvents.
[0216] In a particularly preferred embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises or is composed of the following components:
[0217] (i) 30% to 87.8% by weight of one or more main materials H B ;
[0218] (ii) 0.1% to 5% by weight of one or more phosphorescent materials P B ;and
[0219] (iii) 0.1% to 5% by weight of one or more small FWHM emitters S B ;
[0220] (iv) 12% to 57% by weight of one or more TADF materials E B ; and optionally (v) 0% to 3% by weight of one or more solvents.
[0221] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises less than or equal to 3% by weight of phosphorescent material P. B .
[0222] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises less than or equal to 1% by weight of phosphorescent material P. B .
[0223] In one embodiment of the invention, at least one light-emitting layer B (preferably, each light-emitting layer B) comprises 10% to 40% by weight of one or more TADF materials E. B .
[0224] In one embodiment of the invention, (at least one) small half-peak full width (FWHM) emitter S B With (at least one) phosphorescent material P B mass ratio (S) B :P B )≥1.
[0225] In one embodiment of the invention, at least one small half-peak full width (FWHM) emitter S is present in at least one light-emitting layer B. B With at least one phosphorescent material P B mass ratio (S) B :P B ≥1. In one embodiment of the invention, in each emitting layer B, at least one small half-peak full width (FWHM) emitter S B With at least one phosphorescent material P B mass ratio (S) B :P B )≥1.
[0226] In one embodiment of the invention, (at least one) small half-peak full width (FWHM) emitter S B With (at least one) phosphorescent material P B mass ratio (S) B :P B )<1.
[0227] In one embodiment of the invention, at least one small half-peak full width (FWHM) emitter S is present in at least one light-emitting layer B. B With at least one phosphorescent material P B mass ratio (S) B :P B <1. In one embodiment of the invention, in each emitting layer B, at least one small half-peak full width (FWHM) emitter S B With at least one phosphorescent material P B mass ratio (S)B :P B )<1.
[0228] In one embodiment of the invention, the mass ratio S B :P B Within the range of 1:1 to 30:1, 1.5:1 to 25:1, 2:1 to 20:1, 4:1 to 15:1, 5:1 to 12:1, or 10:1 to 11:1. For example, the mass ratio S B :P B Within the range of (approximately) 20:1, 15:1, 12:1, 10:1, 8:1, 5:1, 4:1, 2:1, 1.5:1, or 1:1.
[0229] In one embodiment of the invention, (at least one) small half-peak full width (FWHM) emitter S B With (at least one) phosphorescent material P B mass ratio (S) B :P B )<1.
[0230] In one embodiment of the invention, the mass ratio P B :S B Within the range of 1:1 to 30:1, 1.5:1 to 25:1, 2:1 to 20:1, 4:1 to 15:1, 5:1 to 12:1, or 10:1 to 11:1. For example, the mass ratio S B :P B Within the range of (approximately) 20:1, 15:1, 12:1, 10:1, 8:1, 5:1, 4:1, 2:1, 1.5:1, or 1:1.
[0231] As mentioned earlier, it is understood that the different sublayers of the luminescent layer B do not necessarily all consist of the same material or even consist of the same material in the same proportion.
[0232] S1-T1 energy relationship
[0233] In one embodiment of the invention, the relationship represented by the following equations (1) and (2) applies:
[0234] E(T1 H )>E(T1 P (1)
[0235] E(T1 P )>E(S1 S (2),
[0236] Therefore, each main material HB The lowest excited triplet state T1 H It has higher energy than each phosphorescent material P B The lowest excited triplet state T1 P And each phosphorescent material P B The lowest excited triplet state T1 P Energy higher than that of each small FWHM emitter S B The lowest excited singlet state S1 S .
[0237] In one embodiment, the above relationships represented by equations (1) and (2) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0238] An organic electroluminescent device is provided, comprising at least one light-emitting layer B, wherein the at least one light-emitting layer B comprises the following components:
[0239] (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0240] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0241] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0242] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ),
[0243] The relationship represented by the following equations (1) and (2) applies:
[0244] E(T1 H )>E(T1 P (1)
[0245] E(T1P )>E(S1 S (2).
[0246] In one embodiment, the above relationships represented by equations (1) and (2) apply to materials included in any one of the light-emitting layers B of the organic electroluminescent device according to the invention.
[0247] In a preferred embodiment of the invention, the relationship represented by the following equations (3) and (4) applies.
[0248] E(T1 H )>E(T1 E (3)
[0249] E(T1 E )>E(T1 P (4),
[0250] Therefore, each main material H B The lowest excited triplet state T1 H It is higher in energy than each TADF material E B The lowest excited triplet state T1 E And each TADF material E B The lowest excited triplet state T1 E It has higher energy than each phosphorescent material P B The lowest excited triplet state T1 P .
[0251] In one embodiment, the relationships expressed by equations (3) and (4) apply to materials included in any one of the at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationships expressed by equations (3) and (4) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0252] In an alternative embodiment of the invention, the relationship represented by the following equations (5) and (6) applies.
[0253] E(T1 P )>E(T1 E (5)
[0254] E(S1 E )>E(S1 S (6),
[0255] Therefore, each phosphorescent material P B The lowest excited triplet state T1 P It is higher in energy than each TADF material E B The lowest excited triplet state T1 EAnd each TADF material E B The lowest excited singlet state S1 E Energy higher than that of each small FWHM emitter S B The lowest excited singlet state S1 S .
[0256] In one embodiment, the relationships expressed by equations (5) and (6) apply to materials included in any one of the light-emitting layers B of the organic electroluminescent device according to the invention. In one embodiment, the relationships expressed by equations (5) and (6) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0257] In a preferred embodiment of the invention, the relationships represented by the following equations (1) to (4) apply:
[0258] E(T1 H )>E(T1 P (1)
[0259] E(T1 P )>E(S1 S (2)
[0260] E(T1 H )>E(S1 E (3)
[0261] E(T1 E )>E(T1 P (4).
[0262] In one embodiment, the relationships expressed by equations (1) to (4) apply to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationships expressed by equations (1) to (4) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0263] In one embodiment of the invention, each phosphorescent material P B The lowest excited triplet state T1 P With each TADF material E B The lowest excited triplet state T1 E The energy difference between them is less than 0.3 eV: E(T1) P )-E(T1 E )<0.3eV, and E(T1) E )-E(T1 P <0.3eV.
[0264] In one embodiment of the invention, in at least one of one or more light-emitting layers B, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P With at least one TADF material E B (Preferably, each TADF material E) B The lowest excited triplet state T1 E The energy difference between them is less than 0.3 eV: E(T1) P )-E(T1 E )<0.3eV, and E(T1) E )-E(T1 P <0.3eV.
[0265] In one embodiment of the invention, in each of one or more light-emitting layers B, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P With at least one TADF material E B (Preferably, each TADF material E) B The lowest excited triplet state T1 E The energy difference between them is less than 0.3 eV: E(T1) P )-E(T1 E )<0.3eV, and E(T1) E )-E(T1 P <0.3eV.
[0266] In one embodiment of the invention, the relationship represented by the following equation (4) applies:
[0267] E(T1 E )>E(T1 P (4).
[0268] In one embodiment, the relationship expressed by equation (4) applies to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In another embodiment, the relationship expressed by equation (4) applies to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0269] In a preferred embodiment of the invention, at least one TADF material E B (Preferably, each TADF material E) B The lowest excited triplet state T1 E With at least one phosphorescent material P B (Preferably, each phosphorescent material P)B The lowest excited triplet state T1 P The energy difference between them is less than 0.2 eV: E(T1) E )-E(T1 P <0.2eV.
[0270] In a preferred embodiment of the invention, in at least one of one or more light-emitting layers B, at least one TADF material E B (Preferably, each TADF material E) B The lowest excited triplet state T1 E With at least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P The energy difference between them is less than 0.2 eV: E(T1) E )-E(T1 P <0.2eV.
[0271] In a preferred embodiment of the invention, in each of one or more light-emitting layers B, at least one TADF material E B (Preferably, each TADF material E) B The lowest excited triplet state T1 E With at least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P The energy difference between them is less than 0.2 eV: E(T1) E )-E(T1 P <0.2eV.
[0272] In a preferred embodiment of the invention, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P With at least one small half-peak full width (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest excited singlet state S1 S (Energy level E(S1) S The energy difference between E(T1) and T1 is less than 0.3 eV: E(T1) P )-E(S1 S <0.3eV.
[0273] In a preferred embodiment of the invention, in at least one of one or more light-emitting layers B, at least one phosphorescent material P B (Preferably, each phosphorescent material P) BThe lowest excited triplet state T1 P With at least one small half-peak full width (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest excited singlet state S1 S The energy difference between them is less than 0.3 eV: E(T1) P )-E(S1 S <0.3eV.
[0274] In a preferred embodiment of the invention, in each of one or more light-emitting layers B, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P With at least one small half-peak full width (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest excited singlet state S1 S The energy difference between them is less than 0.3 eV: E(T1) P )-E(S1 S <0.3eV.
[0275] In a preferred embodiment of the invention, each phosphorescent material P B The lowest excited triplet state T1 P With each small half-peak full width (FWHM) emitter S B The lowest excited singlet state S1 S (Energy level E(S1) S The energy difference between E(T1) and T1 is less than 0.2 eV: E(T1) P )-E(S1 S <0.2eV.
[0276] In a preferred embodiment of the invention, in at least one of one or more light-emitting layers B, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P With at least one small half-peak full width (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest excited singlet state S1 S The energy difference between them is less than 0.2 eV: E(T1) P )-E(S1 S <0.2eV.
[0277] In a preferred embodiment of the invention, in each of one or more light-emitting layers B, at least one phosphorescent material PB (Preferably, each phosphorescent material P) B The lowest excited triplet state T1 P With at least one small half-peak full width (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest excited singlet state S1 S The energy difference between them is less than 0.2 eV: E(T1) P )-E(S1 S <0.2eV.
[0278] HOMO-LUMO Energy
[0279] In a preferred embodiment of the invention, the following requirements are met:
[0280] (i) Each main material H B It has energy E HOMO (H B The highest occupied molecular orbital (HOMO) of H B );and
[0281] (ii) Each phosphorescent material P B It has energy E HOMO (P B The highest occupied molecular orbital (HOMO) of P) B );as well as
[0282] (iii) Full width at half maximum (FWHM) of each emitter S B It has energy E HOMO (S B The highest occupied molecular orbital (HOMO) of ) B );
[0283] The following relationships, represented by equations (10) and (11), apply:
[0284] E HOMO (P B E HOMO (H B (10)
[0285] E HOMO (P B E HOMO (S B (11).
[0286] In one embodiment, the above-described relationship represented by formulas (10) and (11) applies to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the above-described relationship represented by formulas (10) and (11) applies to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0287] In one embodiment of the invention, energy E is present. HOMO (S B The full width at half maximum (FWHM) of each emitter S B The highest occupied molecular orbital HOMO (S B It is higher in energy than one with energy E. HOMO (H B Each main material H) B The highest occupied molecular orbital HOMO (H B ):
[0288] E HOMO (S B E HOMO (H B ).
[0289] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B It is higher in energy than one with energy E. HOMO (H B At least one main material H B (Preferably, each main material H) B The highest occupied molecular orbital (HOMO) of H B ):
[0290] E HOMO (S B E HOMO (H B ).
[0291] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of )B It is higher in energy than one with energy E. HOMO (H B At least one main material H B (Preferably, each main material H) B The highest occupied molecular orbital (HOMO) of H B ):
[0292] E HOMO (S B E HOMO (H B ).
[0293] In one embodiment of the invention, energy E is present. HOMO (S B The full width at half maximum (FWHM) of each emitter S B The highest occupied molecular orbital HOMO (S B It is higher in energy than one with energy E. HOMO (E B Each TADF material E B The highest occupied molecular orbital HOMO (E B ):
[0294] E HOMO (S B E HOMO (E B ).
[0295] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B It is higher in energy than one with energy E. HOMO (E B At least one TADF material E B (Preferably, each TADF material E) B The highest occupied molecular orbital (HOMO) of ) B ):
[0296] E HOMO (S B E HOMO (E B ).
[0297] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E HOMO (SB At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B It is higher in energy than one with energy E. HOMO (E B At least one TADF material E B (Preferably, each TADF material E) B The highest occupied molecular orbital (HOMO) of ) B ):
[0298] E HOMO (S B E HOMO (E B ).
[0299] In one embodiment of the invention, energy E is present. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (E B At least one TADF material E B (Preferably, each TADF material E) B The highest occupied molecular orbital (HOMO) of ) B ):
[0300] E HOMO (P B E HOMO (E B ).
[0301] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (E B At least one TADF material E B (Preferably, each TADF material E) B The highest occupied molecular orbital (HOMO) of ) B ):
[0302] EHOMO (P B E HOMO (E B ).
[0303] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (E B At least one TADF material E B (Preferably, each TADF material E) B The highest occupied molecular orbital (HOMO) of ) B ):
[0304] E HOMO (P B E HOMO (E B ).
[0305] In one embodiment of the invention, energy E is present. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (H B At least one main material H B (Preferably, each main material H) B The highest occupied molecular orbital (HOMO) of H B ):
[0306] E HOMO (P B E HOMO (H B ).
[0307] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (H BAt least one main material H B (Preferably, each main material H) B The highest occupied molecular orbital (HOMO) of H B ):
[0308] E HOMO (P B E HOMO (H B ).
[0309] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (H B At least one main material H B (Preferably, each main material H) B The highest occupied molecular orbital (HOMO) of H B ):
[0310] E HOMO (P B E HOMO (H B ).
[0311] In one embodiment of the invention, energy E is present. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B ):
[0312] E HOMO (P B E HOMO (S B ).
[0313] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (P BAt least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B ):
[0314] E HOMO (P B E HOMO (S B ).
[0315] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B It is higher in energy than one with energy E. HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B ):
[0316] E HOMO (P B E HOMO (S B ).
[0317] In one embodiment of the invention, energy E is present. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is less than 0.3 eV.
[0318] E HOMO (P B )-E HOMO (S B <0.3eV.
[0319] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is less than 0.3 eV:
[0320] E HOMO (P B )-E HOMO (S B <0.3eV.
[0321] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is less than 0.3 eV:
[0322] E HOMO (P B )-E HOMO (S B <0.3eV.
[0323] In one embodiment of the invention, energy E is present. HOMO (P B Each phosphorescent material P BThe highest occupied molecular orbital HOMO (P B ) and has energy E HOMO (S B The full width at half maximum (FWHM) of each emitter S B The highest occupied molecular orbital HOMO (S B The energy difference between them is less than 0.2 eV: E HOMO (P B )-E HOMO (S B <0.2eV.
[0324] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is less than 0.2 eV.
[0325] E HOMO (P B )-E HOMO (S B <0.2eV.
[0326] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is less than 0.2 eV.
[0327] E HOMO (P B )-E HOMO (SB <0.2eV.
[0328] In a preferred embodiment of the invention, it has energy E HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is greater than 0.0 eV and less than 0.3 eV:
[0329] 0.0eV <E HOMO (P B )-E HOMO (S B <0.3eV.
[0330] In a preferred embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is greater than 0.0 eV and less than 0.3 eV:
[0331] 0.0eV <E HOMO (P B )-E HOMO (S B <0.3eV.
[0332] In a preferred embodiment of the invention, each of at least one light-emitting layer B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P)B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is greater than 0.0 eV and less than 0.3 eV:
[0333] 0.0eV <E HOMO (P B )-E HOMO (S B <0.3eV.
[0334] In one embodiment of the invention, energy E is present. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is greater than or equal to 0.1 eV and less than or equal to 0.8 eV.
[0335] 0.1eV≤E HOMO (P B )-E HOMO (S B )≤0.8eV.
[0336] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) BThe energy difference between them is greater than or equal to 0.1 eV and less than or equal to 0.8 eV:
[0337] 0.1eV≤E HOMO (P B )-E HOMO (S B )≤0.8eV.
[0338] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. HOMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The highest occupied molecular orbital (HOMO) of P) B ) and has energy E HOMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The highest occupied molecular orbital (HOMO) of ) B The energy difference between them is greater than or equal to 0.1 eV and less than or equal to 0.8 eV:
[0339] 0.1eV≤E HOMO (P B )-E HOMO (S B )≤0.8eV.
[0340] In a preferred embodiment of the invention, the following requirements are met:
[0341] (i) Each main material H B It has energy E LUMO (H B The lowest unoccupied molecular orbital LUMO (H) B );and
[0342] (ii) Each phosphorescent material P B It has energy E LUMO (P B The lowest unoccupied molecular orbital LUMO (P) B );and
[0343] (iii) Full width at half maximum (FWHM) of each emitter S B It has energy E LUMO (S B The lowest unoccupied molecular orbital (LUMO) of ) B );as well as
[0344] (iv) Each thermally activated delayed fluorescence (TADF) material E B It has energy E LUMO (E B The lowest unoccupied molecular orbital LUMO (E) B ),
[0345] The relationship represented by equations (12) and (13) below applies:
[0346] E LUMO (E B ) <E LUMO (H B (12)
[0347] E LUMO (E B ) <E LUMO (P B (13).
[0348] In one embodiment, the above-described relationship represented by equations (12) and (13) applies to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the above-described relationship represented by equations (12) and (13) applies to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0349] In one embodiment of the invention, the electroluminescent device includes a light-emitting layer B composed of one or more sublayers, wherein the one or more sublayers of the light-emitting layer B include the following components:
[0350] (i) Main material H B It has energy E LUMO (H B The lowest unoccupied molecular orbital LUMO (H) B );and
[0351] (ii) Phosphorescent materials P B It has energy E LUMO (P B The lowest unoccupied molecular orbital LUMO (P) B );and
[0352] (iii) Small half-peak full width (FWHM) emitter S B It has energy E LUMO (S B The lowest unoccupied molecular orbital (LUMO) of ) B );as well as
[0353] (iv) Thermally activated delayed fluorescence (TADF) material E B It has energy ELUMO (E B The lowest unoccupied molecular orbital LUMO (E) B ),
[0354] Among them, the relationships represented by the following equations (12) to (14) apply:
[0355] E LUMO (E B ) <E LUMO (H B (12)
[0356] E LUMO (E B ) <E LUMO (P B (13)
[0357] E LUMO (E B ) <E LUMO (S B (14).
[0358] In one embodiment, the relationships expressed by equations (12) to (14) apply to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationships expressed by equations (12) to (14) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0359] In one embodiment of the invention, the relationships represented by the following equations (10) to (13) apply:
[0360] E HOMO (P B E HOMO (H B (10)
[0361] E HOMO (P B E HOMO (S B (11)
[0362] E LUMO (E B ) <E LUMO (H B (12)
[0363] E LUMO (E B ) <E LUMO (P B (13).
[0364] In one embodiment, the relationships expressed by formulas (10) to (13) apply to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationships expressed by formulas (10) to (13) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0365] In one embodiment of the invention, the relationships represented by the following equations (10) to (14) apply:
[0366] E HOMO (P B E HOMO (H B (10)
[0367] E HOMO (P B E HOMO (S B (11)
[0368] E LUMO (E B ) <E LUMO (H B (12)
[0369] E LUMO (E B ) <E LUMO (P B (13)
[0370] E LUMO (E B ) <E LUMO (S B (14).
[0371] In one embodiment, the relationships expressed by equations (10) to (14) apply to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationships expressed by equations (10) to (14) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0372] In one embodiment of the invention, energy E is present. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B It is higher in energy than one with energy E. LUMO (E BAt least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0373] E LUMO (S B E LUMO (E B ).
[0374] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B It is higher in energy than one with energy E. LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0375] E LUMO (S B E LUMO (E B ).
[0376] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B It is higher in energy than one with energy E. LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0377] E LUMO (S B E LUMO (E B ).
[0378] In one embodiment of the invention, energy E is present. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is less than 0.3 eV:
[0379] E LUMO (S B )–E LUMO (E B <0.3eV.
[0380] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is less than 0.3 eV:
[0381] E LUMO (S B )–E LUMO (E B <0.3eV.
[0382] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E BAt least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is less than 0.3 eV:
[0383] E LUMO (S B )–E LUMO (E B <0.3eV.
[0384] In one embodiment of the invention, energy E is present. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is less than 0.2 eV.
[0385] E LUMO (S B )–E LUMO (E B <0.2eV.
[0386] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is less than 0.2 eV.
[0387] E LUMO (S B )–E LUMO (E B <0.2eV.
[0388] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is less than 0.2 eV.
[0389] E LUMO (S B )–E LUMO (E B <0.2eV.
[0390] In one embodiment of the invention, energy E is present. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is greater than 0.0 eV and less than 0.3 eV:
[0391] 0.0eV <E LUMO (S B )–E LUMO (E B <0.3eV.
[0392] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is greater than 0.0 eV and less than 0.3 eV:
[0393] 0.0eV <E LUMO (S B )–E LUMO (E B <0.3eV.
[0394] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. LUMO (S B At least one small half-peak full width at half maximum (FWHM) emitter S B (Preferably, each small half-peak full width (FWHM) emitter S) B The lowest unoccupied molecular orbital (LUMO) of ) B ) and has energy E LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B The energy difference between them is greater than 0.0 eV and less than 0.3 eV:
[0395] 0.0eV <E LUMO (S B )–E LUMO (E B <0.3eV.
[0396] In one embodiment of the invention, energy E is present. LUMO (P B Each phosphorescent material P B The lowest unoccupied molecular orbital LUMO (P B It is higher in energy than one with energy E. LUMO (E B Each TADF material E B The lowest unoccupied molecular orbital LUMO (E B ):
[0397] E LUMO (P B E LUMO (E B ).
[0398] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. LUMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest unoccupied molecular orbital LUMO (P) B It is higher in energy than one with energy E. LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0399] E LUMO (P B E LUMO (E B ).
[0400] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. LUMO (P B At least one phosphorescent material P B (Preferably, each phosphorescent material P) B The lowest unoccupied molecular orbital LUMO (P) B It is higher in energy than one with energy E. LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0401] E LUMO (P B E LUMO (E B ).
[0402] In one embodiment of the invention, energy E is present. LUMO (H B At least one main material H B (Preferably, each main material H) B The lowest unoccupied molecular orbital LUMO (H) B It is higher in energy than one with energy E. LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0403] E LUMO (H B E LUMO (E B ).
[0404] In one embodiment of the invention, at least one of one or more light-emitting layers B has an energy E. LUMO (H B At least one main material H B (Preferably, each main material H) B The lowest unoccupied molecular orbital LUMO (H) B It is higher in energy than one with energy E. LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0405] E LUMO (H B E LUMO (E B ).
[0406] In one embodiment of the invention, each of at least one light-emitting layer B has an energy E. LUMO (H B At least one main material H B (Preferably, each main material H) B The lowest unoccupied molecular orbital LUMO (H) B It is higher in energy than one with energy E. LUMO (E B At least one TADF material E B (Preferably, each TADF material E) B The lowest unoccupied molecular orbital LUMO (E) B ):
[0407] E LUMO (H B E LUMO (E B ).
[0408] Relationship to maximum emission value
[0409] In one embodiment of the invention, the relationship represented by equations (16) and (17) applies:
[0410] |E λmax (P B )-E λmax(S B )|<0.30eV (16),
[0411] |E λmax (E B )-E λmax (S B )|<0.30eV (17),
[0412] This means that, in the context of this invention, the phosphorescent material P is given in electron volts (eV). B The maximum energy E emitted λmax (P B ) and, in the context of this invention, a small FWHM emitter S given in electron volts (eV). B The maximum energy E emitted λmax (S B The energy difference between them is less than 0.30 eV. And this means that, in the context of this invention, the TADF material E given in electron volts (eV) B The maximum energy E emitted λmax (E B ) and, in the context of this invention, a small FWHM emitter S given in electron volts (eV). B The maximum energy E emitted λmax (S B The energy difference between them is less than 0.30 eV.
[0413] In one embodiment, the above-described relationships represented by equations (16) and (17) apply to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the above-described relationships represented by equations (16) and (17) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0414] An organic electroluminescent device is provided, comprising at least one light-emitting layer B composed of one or more sublayers, wherein the one or more sublayers are adjacent to each other and, as a whole, comprise the following components:
[0415] (i) at least one main material H B ;and
[0416] (ii) at least one phosphorescent material P B It has energy E λmax (P B The maximum emission value λ max (P B );and
[0417] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has energy E λmax (S B The maximum emission value λ max (S B ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0418] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has energy E λmax (E B The maximum emission value λ max (E B ),
[0419] One or more sublayers located on the outer surface of the light-emitting layer B contain materials selected from phosphorescent material P. B Small FWHM emitter S B and TADF material E B At least one (emitter) material in the group, wherein the relationship expressed by the following equations (16) and (17) applies:
[0420] |E λmax (P B )-E λmax (S B )|<0.30eV (16),
[0421] |E λmax (E B )-E λmax (S B )|<0.30eV (17).
[0422] In a preferred embodiment of the invention, the relationship represented by equations (18) and (19) applies:
[0423] |E λmax (P B )-E λmax (S B )|<0.20eV (18),
[0424] |E λmax (E B )-E λmax (S B )|<0.20eV (19),
[0425] This means that, in the context of this invention, the phosphorescent material P is given in electron volts (eV). BThe maximum energy E emitted λmax (P B ) and, in the context of this invention, a small FWHM emitter S given in electron volts (eV). B The maximum energy E emitted λmax (S B The energy difference between them is less than 0.20 eV. And this means that, in the context of this invention, the TADF material E given in electron volts (eV) B The maximum energy E emitted λmax (E B ) and, in the context of this invention, a small FWHM emitter S given in electron volts (eV). B The maximum energy E emitted λmax (S B The energy difference between them is less than 0.20 eV.
[0426] In one embodiment, the above-described relationships represented by equations (18) and (19) apply to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the above-described relationships represented by equations (18) and (19) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0427] One embodiment of the invention relates to an organic electroluminescent device, wherein,
[0428] (ii) at least one phosphorescent material P B It has energy E λmax (P B The maximum emission value λ max (P B );and
[0429] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has energy E λmax (S B The maximum emission value λ max (S B ), where S B It emits light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0430] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has energy E λmax (E B The maximum emission value λ max (E B ),
[0431] Among them, equations (18) and (19) are applicable:
[0432] |E λmax (P B )-E λmax (S B )|<0.20eV (18),
[0433] |E λmax (E B )-E λmax (S B )|<0.20eV (19).
[0434] In even more preferred embodiments of the invention, the relationship represented by equations (20) and (21) applies:
[0435] |E λmax (P B )-E λmax (S B )|<0.1eV (20),
[0436] |E λmax (E B )-E λmax (S B )|<0.10eV (21),
[0437] This means that, in the context of this invention, the phosphorescent material P is given in electron volts (eV). B The maximum energy E emitted λmax (P B ) and, in the context of this invention, a small FWHM emitter S given in electron volts (eV). B The maximum energy E emitted λmax (S B The energy difference between them is less than 0.10 eV. And this means that, in the context of this invention, the TADF material E given in electron volts (eV) B The maximum energy E emitted λmax (E B ) and, in the context of this invention, a small FWHM emitter S given in electron volts (eV). B The maximum energy E emitted λmax (S B The energy difference between them is less than 0.10 eV.
[0438] In one embodiment, the above-described relationship represented by formulas (20) and (21) applies to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the above-described relationship represented by formulas (20) and (21) applies to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0439] In one embodiment of the invention, the relationship represented by equation (22) applies:
[0440] E λmax (P B E λmax (S B ) (twenty two),
[0441] This means that the phosphorescent material P, given in electron volts (eV) below in this invention, B The maximum energy E emitted λmax (P B The small FWHM emitter S, given in electron volts (eV) in the context of this invention, is greater than that of the small FWHM emitter S. B The maximum energy E emitted λmax (S B ).
[0442] In one embodiment, the relationship expressed by formula (22) applies to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationship expressed by formula (22) applies to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0443] In one embodiment of the invention, the relationship represented by equation (22-a) applies:
[0444] E λmax (E B E λmax (S B (22-a),
[0445] This means that, in the context of this invention, the TADF material E is given in electron volts (eV). B The maximum energy E emitted λmax (E B The small FWHM emitter S, given in electron volts (eV) in the context of this invention, is greater than that of the small FWHM emitter S. B The maximum energy E emitted λmax (S B ).
[0446] In one embodiment, the relationship expressed by formula (22-a) applies to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationship expressed by formula (22-a) applies to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0447] Device color and performance
[0448] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED) that emits light at different color points. According to the present invention, the electroluminescent device (e.g., an OLED) emits light having a narrow emission band (small half-peak full width (FWHM)). In a preferred embodiment, the electroluminescent device (e.g., an OLED) according to the invention emits light with an FWHM having a main emission peak below 0.25 eV (more preferably below 0.20 eV, even more preferably below 0.15 eV, or even below 0.13 eV).
[0449] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency of greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 18%, or even greater than 20%) at (nits) and exhibits a maximum emission value between 500 nm and 560 nm.
[0450] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 18%, or even greater than 20%) and shows a maximum emission value between 510 nm and 550 nm.
[0451] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 18%, or even greater than 20%) and shows a maximum emission value between 515 nm and 540 nm.
[0452] In a preferred embodiment, the electroluminescent device (e.g., OLED) operates at a constant current density J0 = 15 mA / cm². 2The LT95 value exhibits a value greater than 100 hours (preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or even greater than 1000 hours).
[0453] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED) that emits light at different color points. According to the invention, the electroluminescent device (e.g., an OLED) emits light having a narrow emission band (small half-peak full width (FWHM)). In a preferred embodiment, the electroluminescent device (e.g., an OLED) according to the invention emits light with an FWHM having a main emission peak below 0.25 eV (more preferably below 0.20 eV, even more preferably below 0.15 eV, or even below 0.13 eV).
[0454] Another embodiment of the invention relates to an electroluminescent device (e.g., an OLED) that emits light having CIEx and CIEy color coordinates close to CIEx (= 0.170) and CIEy (= 0.797), which are the primary color green (CIEx = 0.170 and CIEy = 0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020). Therefore, the electroluminescent device (e.g., the OLED) can be used in ultra-high definition (UHD) displays (e.g., UHD-TVs). In this context, the term "close to" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting devices (where the top electrode is typically transparent) are typically used, while the test device used throughout this application represents a bottom-emitting device (where both the bottom electrode and substrate are transparent). Therefore, another aspect of the present invention relates to an electroluminescent device (e.g., an OLED) whose emission exhibits CIEx color coordinates between 0.15 and 0.45 (preferably between 0.15 and 0.35, more preferably between 0.15 and 0.30, or even more preferably between 0.15 and 0.25, or even more preferably between 0.15 and 0.20) and / or CIEy color coordinates between 0.60 and 0.92 (preferably between 0.65 and 0.90, more preferably between 0.70 and 0.88, or even more preferably between 0.75 and 0.86, or even more preferably between 0.79 and 0.84).
[0455] Another embodiment of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to CIEx (=0.265) and CIEy (=0.65), which are used as the primary color green (CIEx=0.265 and CIEy=0.65) as defined by DCIP3. In this context, the term "close to" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting devices (where the top electrode is typically transparent) are typically used, while the test devices used throughout this application represent bottom-emitting devices (where both the bottom electrode and substrate are transparent). Therefore, another aspect of the present invention relates to an OLED whose bottom emission exhibits CIEx color coordinates between 0.2 and 0.45 (preferably between 0.2 and 0.35, or more preferably between 0.2 and 0.30, or even more preferably between 0.24 and 0.28, or even more preferably between 0.25 and 0.27) and / or CIEy color coordinates between 0.60 and 0.9 (preferably between 0.6 and 0.8, more preferably between 0.60 and 0.70, or even more preferably between 0.62 and 0.68, or even more preferably between 0.64 and 0.66).
[0456] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 18%, or even greater than 20%) and shows a maximum emission value between 420 nm and 500 nm.
[0457] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 18%, or even greater than 20%) and shows a maximum emission value between 440 nm and 480 nm.
[0458] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 18%, or even greater than 20%) and shows a maximum emission value between 450 nm and 470 nm.
[0459] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 18%, or even greater than 20%), and / or exhibits a maximum emission value between 420 nm and 500 nm (preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm), and / or at 500 cd / m 2 The LT80 value exhibits a value greater than 100 hours (preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or even greater than 1000 hours).
[0460] Another embodiment of the present invention relates to an electroluminescent device (e.g., an OLED) that emits light at different color points. According to the invention, the electroluminescent device (e.g., an OLED) emits light having a narrow emission band (small half-peak full width (FWHM)). In a preferred embodiment, the electroluminescent device (e.g., an OLED) according to the invention emits light with an FWHM having a main emission peak below 0.25 eV (more preferably below 0.20 eV, even more preferably below 0.15 eV, or even below 0.13 eV).
[0461] Another aspect of the invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to CIEx (=0.131) and CIEy (=0.046), which are the primary color blue (CIEx=0.131, CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and therefore the OLED is suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). In commercial applications, top-emitting devices (with a transparent top electrode) are typically used, while the test device used throughout this application represents a bottom-emitting device (with a transparent bottom electrode and substrate). When the emitter is changed from bottom to top, the CIEy color coordinates of the blue device can be reduced by up to two times, while the CIEx remains almost unchanged (Okinaka et al., Society for Information Display International Symposium Digest of Technical Papers, 2015, 46(1):312-313, DOI:10.1002 / sdtp.10480). Therefore, another aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates between 0.02 and 0.3 (preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20, or even more preferably between 0.08 and 0.18, or even more preferably between 0.10 and 0.15) and / or CIEy color coordinates between 0.00 and 0.45 (preferably between 0.01 and 0.3, more preferably between 0.02 and 0.20, or even more preferably between 0.03 and 0.15, or even more preferably between 0.04 and 0.10).
[0462] Another aspect of the present invention relates to an electroluminescent device (e.g., an OLED), wherein the electroluminescent device (e.g., an OLED) has a light emission rate of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 8% (more preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even greater than 20%), and / or exhibits a maximum emission value between 590 nm and 690 nm (preferably between 610 nm and 665 nm, even more preferably between 620 nm and 640 nm), and / or at 500 cd / m 2The OLED exhibits an LT80 value greater than 100 hours (preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or even more preferably greater than 1000 hours). Therefore, another aspect of the invention relates to an OLED whose emission exhibits a CIEy color coordinate greater than 0.25 (preferably greater than 0.27, more preferably greater than 0.29, or even more preferably greater than 0.30).
[0463] Another embodiment of the invention relates to an electroluminescent device (e.g., an OLED) that emits light having CIEx and CIEy color coordinates close to those of CIEx (=0.708) and CIEy (=0.292), which are the primary color red (CIEx=0.708, CIEy=0.292) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and thus the electroluminescent device (e.g., the OLED) is suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TVs). In this context, the term "close to" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting (top electrode is transparent) devices are typically used, while the test device used throughout this application represents a bottom-emitting device (bottom electrode and substrate are transparent). Therefore, another aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates between 0.60 and 0.88 (preferably between 0.61 and 0.83, more preferably between 0.63 and 0.78, or even more preferably between 0.66 and 0.76, or even more preferably between 0.68 and 0.73) and / or CIEy color coordinates between 0.25 and 0.70 (preferably between 0.26 and 0.55, more preferably between 0.27 and 0.45, or even more preferably between 0.28 and 0.40, or even more preferably between 0.29 and 0.35).
[0464] Therefore, another aspect of the present invention relates to an electroluminescent device (e.g., an OLED) with a light emission intensity of 14500 cd / m². 2 It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 17%, or even greater than 20%) and / or exhibits a maximum emission value between 590 nm and 690 nm (preferably between 610 nm and 665 nm, even more preferably between 620 nm and 640 nm).
[0465] One of the purposes of interest for organic electroluminescent devices is the generation of light. Therefore, the present invention also relates to a method for generating light within a desired wavelength range, the method comprising the step of providing an organic electroluminescent device according to any one of the present invention.
[0466] Therefore, another aspect of the present invention relates to a method for generating light within a desired wavelength range, the method comprising the following steps:
[0467] (i) providing an organic electroluminescent device according to the present invention; and
[0468] (ii) Apply current to the organic electroluminescent device.
[0469] Another aspect of the present invention relates to a process for manufacturing an organic electroluminescent device by assembling the aforementioned components. The present invention also relates to a method for generating green light, specifically a method for generating green light using the organic electroluminescent device.
[0470] Another aspect of the present invention relates to an organic electroluminescent device, wherein at least one (preferably exactly one) of the relationships represented by the following formulas (23) to (25) applies to materials included in the same light-emitting layer B:
[0471] 440nm<λ max (S B )<470nm (23)
[0472] 510nm<λ max (S B <550nm (24)
[0473] 610nm<λ max (S B <665nm (25),
[0474] Where, λ max (S B ) is at least one small FWHM emitter S B (Preferably, each small FWHM emitter S) B The maximum emission value is given in nanometers (nm).
[0475] In one embodiment of the invention, at least one (preferably exactly one) of the relationships represented by formulas (23) to (25) above applies to the material included in any one of the light-emitting layers B of the organic electroluminescent device according to the invention.
[0476] Another aspect of the invention relates to a method for generating light, the method comprising the steps of:
[0477] (i) providing an organic electroluminescent device according to the present invention; and
[0478] (ii) Apply current to the organic electroluminescent device.
[0479] Another aspect of the invention relates to a method for generating light, the method comprising the steps of:
[0480] (i) providing an organic electroluminescent device according to the present invention; and
[0481] (ii) Apply current to the organic electroluminescent device.
[0482] The method is used to generate light in a wavelength range selected from one of the following wavelength ranges:
[0483] (i) 510nm to 550nm; or
[0484] (ii) 440nm to 470nm, or
[0485] (iii) 610nm to 665nm.
[0486] Those skilled in the art will understand that at least one TADF material E B and at least one phosphorescent material P B (See below) can be used as an emitter in an organic electroluminescent device. However, preferably, in the organic electroluminescent device according to the invention, at least one TADF material E B and at least one phosphorescent material P B Its primary function is not to emit light. In a preferred embodiment, the organic electroluminescent device according to the invention emits light when a voltage (and current) is applied, wherein the emission is primarily (i.e., to a degree greater than 50% (preferably greater than 60%, more preferably greater than 70%, even more preferably greater than 80%, or even greater than 90%) attributable to at least one small FWHM emitter S B The emitted fluorescence. Therefore, the organic electroluminescent device according to the invention preferably also exhibits a narrow emission characterized by a small FWHM of a main emission peak below 0.25 eV (more preferably below 0.20 eV, even more preferably below 0.15 eV, or even below 0.13 eV).
[0487] In a preferred embodiment of the invention, the relationship represented by the following equation (26) applies:
[0488]
[0489] in,
[0490] FWHMD The full width at half maximum (FWHM) of the main emission peak of the organic electroluminescent device according to the present invention is expressed in electron volts (eV); and
[0491] FWHM SB Indicates that it is used in the case of FWHM D In FWHM's organic electroluminescent devices, one or more host materials H B One or more small FWHM emitters S B The photoluminescence spectrum (fluorescence spectrum, measured at room temperature (i.e., approximately 20°C)) of the spin-coated film exhibits an electron volt (eV) FWHM. In other words, it is used to determine the FWHM. SB The spin-coated film preferably comprises the same small FWHM emitter S in the same weight ratio as the light-emitting layer B of the organic electroluminescent device. B or multiple small FWHM emitters S B .
[0492] For example, if the emitting layer B comprises two small FWHM emitters S, each having a concentration of 1% by weight. B The spin-coated film preferably also includes two small FWHM emitters S, each accounting for 1% by weight. B Each of the components. In this exemplary case, the matrix material of the spin-coated film will account for 98% by weight of the spin-coated film. The matrix material of the spin-coated film can be selected to reflect the host material H included in the light-emitting layer B of the organic electroluminescent device. B The weight ratio. In the example above, if the light-emitting layer B comprises a single host material H B In this case, the host material will preferably be the sole matrix material of the spin-coated film. However, if, in the above example, the luminescent layer B comprises two host materials H... B One has a content of 60% by weight and the other has a content of 20% by weight (i.e., in a 3:1 ratio), then the spin-coated film (containing 1% by weight of the two small FWHM emitters S) B The matrix material described above for each of the components in the EML will preferably be one of the two host materials H present in the EML. B A 3:1 mixture.
[0493] If more than one light-emitting layer B is included in the organic electroluminescent device according to the invention, the relationship represented by the above formula (26) preferably applies to all light-emitting layers B included in the device.
[0494] In one embodiment, for at least one light-emitting layer B of the organic electroluminescent device according to the present invention, the above-mentioned ratio FWHM D :FWHM SBIt is equal to or less than 1.50, preferably 1.40, even more preferably 1.30, even more preferably 1.20 or even 1.10.
[0495] In one embodiment, for each light-emitting layer B of the organic electroluminescent device according to the present invention, the above-mentioned ratio FWHM D :FWHM SB It is equal to or less than 1.50, preferably 1.40, even more preferably 1.30, even more preferably 1.20 or even 1.10.
[0496] It should be noted that, for the small FWHM emitter S used in the context of this invention B The selection of the fluorescent emitter, the FWHM value, can be determined as described in the subsections below (in short: see below, preferably by spin-coating a film of the corresponding emitter in poly(methyl methacrylate) PMMA having a concentration of 1% to 5% by weight (specifically, 2% by weight), or by solution). That is, the exemplary small FWHM emitters S listed in Table 1S B The FWHM value should not be interpreted as FWHM in the context of equation (26) and the relevant preferred embodiments of the present invention. SB value.
[0497] The examples and claims further illustrate the invention.
[0498] (Multiple) Main Materials H B
[0499] According to the invention, it includes one or more host materials H in any one of at least one light-emitting layer B. B Any one of them can be a p-body H exhibiting high hole mobility. P The n-substrate H exhibits high electron mobility N Or a bipolar host material H exhibiting both high hole mobility and high electron mobility. BP .
[0500] In the context of this invention, the n-body exhibiting high electron mobility preferably has a LUMO energy E equal to or less than -2.50 eV. LUMO (H N (E) LUMO (H N (≤–2.50 eV). Preferably, E LUMO (H N )≤–2.60eV, more preferably, E LUMO (H N )≤–2.65eV, or even more preferably, E LUMO (H N≤–2.70 eV. LUMO is the lowest unoccupied molecular orbital. The energy of LUMO is determined as described in a later subsection of this paper.
[0501] In the context of this invention, p-body exhibiting high hole mobility preferably has a HOMO energy E equal to or greater than -6.30 eV. HOMO (H P (E) HOMO (H P (≥–6.30 eV), preferably, E HOMO (H P )≥–5.90eV, more preferably, E HOMO (H P )≥–5.70eV, or even more preferably, E HOMO (H P ≥–5.40 eV, or even E HOMO (H P ≥–2.60 eV. HOMO is the highest occupied molecular orbital. The energy of HOMO is determined as described in a later subsection of this paper.
[0502] In one embodiment of the invention, each body material H B It is the main body H P p main body H P It has a HOMO energy E equal to or greater than -6.30 eV. HOMO (H P (E) HOMO (H P (≥–6.30 eV), preferably, E HOMO (H P )≥–5.90eV, more preferably, E HOMO (H P )≥–5.70eV, or even more preferably, E HOMO (H P ≥–5.40 eV. HOMO is the highest occupied molecular orbital. The energy of HOMO is determined as described in a later subsection of this paper.
[0503] In one embodiment of the invention, at least one p-body H P (Preferably, each p body H) P It has a HOMO energy E less than -5.60 eV. HOMO (H P ).
[0504] In one embodiment of the invention, the organic electroluminescent device includes at least one light-emitting layer B composed of one or more sublayers, wherein the one or more sublayers are adjacent to each other and, as a whole, comprise the following components:
[0505] (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );
[0506] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0507] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and optionally...
[0508] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ),
[0509] One or more sublayers located on the outer surface of the light-emitting layer B contain materials selected from phosphorescent material P. B Small FWHM emitter S B and TADF material E B At least one (emitter) material in the group,
[0510] Among them, at least one main material H B It has an energy E of less than -5.60 eV HOMO (H B The highest occupied molecular orbital (HOMO) of H B Preferably, each main material H B It has an energy E of less than -5.60 eV HOMO (H B The highest occupied molecular orbital (HOMO) of H B ).
[0511] In the context of this invention, bipolar hosts exhibiting high electron mobility preferably have a LUMO energy E equal to or less than -2.50 eV. LUMO (H BP (E) LUMO (HBP (≤-2.50eV). Preferably, E LUMO (H BP )≤–2.60eV, more preferably, E LUMO (H BP )≤–2.65eV, or even more preferably, E LUMO (H BP ≤–2.70 eV. LUMO is the lowest unoccupied molecular orbital. The energy of LUMO is determined as described in a later subsection of this paper.
[0512] In the context of this invention, bipolar hosts exhibiting high hole mobility preferably have a HOMO energy E equal to or greater than -6.30 eV. HOMO (H BP (E) HOMO (H BP (≥-6.30eV), preferably, E HOMO (H BP )≥-5.90eV. More preferably, E HOMO (H BP )≥-5.70eV, or even more preferably, E HOMO (H BP ≥-5.40 eV. HOMO is the highest occupied molecular orbital. The energy of HOMO is determined as described in the subsections later in this paper.
[0513] In one embodiment of the invention, the bipolar host material H BP (Preferably, each bipolar host material H) BP The following two requirements must be met:
[0514] (i) It has a LUMO energy E equal to or less than -2.50 eV. LUMO (H BP (E) LUMO (H BP (≤–2.50 eV). Preferably, E LUMO (H BP )≤–2.60eV, more preferably, E LUMO (H BP )≤–2.65eV, or even more preferably, E LUMO (H BP ≤–2.70 eV. LUMO is the lowest unoccupied molecular orbital. The energy of LUMO is determined as described in a later subsection of this paper.
[0515] (ii) It has a HOMO energy E equal to or greater than -6.30 eV. HOMO (H BP (E) HOMO (HBP )≥–6.30eV, preferably, E HOMO (H BP )≥–5.90eV. More preferably, E HOMO (H BP )≥–5.70eV, or even more preferably, E HOMO (H BP ≥–5.40 eV. HOMO is the highest occupied molecular orbital. The energy of HOMO is determined as described in a later subsection of this paper.
[0516] Those skilled in the art will know which materials are suitable host materials for use in organic electroluminescent devices such as the organic electroluminescent devices of the present invention. See, for example: Y. Tao, C. Yang, J. Quin, Chemical Society Reviews 2011, 40, 2943, DOI:10.1039 / C0CS00160K; K. S. O., J. Lee, The Chemical Record 2015, 16(1), 159, DOI:10.1002 / tcr.201500221; T. Chatterjee, K.-T. Wong, Advanced Optical Materials 2018, 7(1), 1800565, DOI:10.1002 / adom.201800565; Q. Wang, Q.-S. Tian, Y.-L. Zhang, X. Tang, L.-S. Liao, Journal of Materials Chemistry C2019,7,11329,DOI:10.1039 / C9TC03092A.
[0517] In addition, for example, US2006006365(A1), US2006208221(A1), US2005069729(A1), EP1205527(A1), US2009302752(A1), US20090134784(A1), US2009302742(A1), US2010187977(A1), US2012068170(A1), US2012097899(A1), US2006121308(A1), US2006121308(A1), US2009167166(A1), US2007176147(A1), US2015322091(A1), U US2011105778(A1), US2011201778(A1), US2011121274(A1), US2009302742(A1), US2010187977(A1), US2010244009(A1), US2009136779(A1), EP2182040(A2), US2012202997(A1), US2019393424(A1), US2019393425(A1), US2020168819(A1), US2020079762(A1) and US2012292576(A1) disclose host materials that can be used in organic electroluminescent devices according to the present invention. It is understood that this does not imply that the invention is limited to organic electroluminescent devices containing the host materials disclosed in the cited references. It is also understood that any host material used in the prior art can be a suitable host material in the context of this invention. B .
[0518] In one embodiment of the invention, each light-emitting layer B of the organic electroluminescent device according to the invention includes one or more p-body Hs. P In one embodiment of the invention, each light-emitting layer B of the organic electroluminescent device according to the invention comprises only a single host material, and said host material is a p-host H. P .
[0519] In one embodiment of the invention, each light-emitting layer B of the organic electroluminescent device according to the invention includes one or more n-body H. N In another embodiment of the invention, each light-emitting layer B of the organic electroluminescent device according to the invention comprises only a single host material, and said host material is n host H. N .
[0520] In one embodiment of the invention, each light-emitting layer B of the organic electroluminescent device according to the invention includes one or more bipolar bodies H. BPIn one embodiment of the invention, each light-emitting layer B of the organic electroluminescent device according to the invention comprises only a single host material, and said host material is a bipolar host H. BP .
[0521] In another embodiment of the invention, at least one light-emitting layer B of the organic electroluminescent device according to the invention comprises at least two different host materials H. B In this case, more than one host material H exists in the corresponding luminescent layer B. B It can all be p main body H P Or all of them are n-subject H N Or all of them are bipolar entities H BP However, it can also be a combination of them.
[0522] It is understood that if the organic electroluminescent device according to the invention comprises more than one light-emitting layer B, then any one of them may independently comprise a host material H as defined above, independent of one or more other light-emitting layers B. B or greater than one main material H B It is also understood that the different light-emitting layers B included in the organic electroluminescent device according to the invention need not all comprise the same material or even comprise the same material at the same concentration.
[0523] It is understood that if the light-emitting layer B of the organic electroluminescent device according to the invention consists of more than one sublayer, then any one of them may independently comprise a host material H as defined above, independent of one or more other sublayers. B or greater than one main material H B It is also understood that the different sublayers of the light-emitting layer B included in the organic electroluminescent device according to the invention need not all comprise the same material or even comprise the same material at the same concentration.
[0524] If included in the same light-emitting layer B of the organic electroluminescent device according to the invention, then at least one p-body H P and at least one n-body H N An excitocomplex can be optionally formed. Those skilled in the art know how to select the H group that forms the excitocomplex. P and H N To and including H P and H N The selection criteria for HOMO and / or LUMO energy level requirements. That is, under conditions where excitocomplex formation is expected, the p-host material H... P The highest occupied molecular orbital (HOMO) can be more energetically advanced than the n-host material H. N The HOMO value is at least 0.20 eV, and the p-based host material HP The lowest unoccupied molecular orbital (LUMO) can be more energetically advanced than that of the host material H. N The LUMO is at least 0.20 eV higher.
[0525] In a preferred embodiment of the invention, at least one main material H B (For example, H) P H N and / or H BP H is an organic host material, which, in the context of the invention, means that it does not contain any transition metals. In a preferred embodiment of the invention, all host materials H in the electroluminescent device of the present invention... B (H P H N and / or H BP () are organic host materials, which, in the context of the invention, means that they do not contain any transition metals. Preferably, at least one host material H B (More preferably, all main materials H) B (H P H N and / or H BP It is mainly composed of the elements hydrogen (H), carbon (C) and nitrogen (N), but may also include, for example, oxygen (O), boron (B), silicon (Si), fluorine (F) and bromine (Br).
[0526] In one embodiment of the invention, each body material H B It is the main body H P .
[0527] In a preferred embodiment of the invention, the p-body H is optionally included in any one of at least one light-emitting layer B as a whole (consisting of one (sub)layer or including more than one sub)layer. P Includes or is composed of the following components:
[0528] A first chemical part, including according to formula H P -I, Formula H P -II, Formula H P -III, Formula H P -IV, Formula H P -V, Formula H P -VI, Formula H P -VII, Equation H P -VIII, Formula H P -IX and H P The structure of any one of -X, or by means of equation H P -I, Formula H P -II, Formula H P -III, Formula H P-IV, Formula H P -V, Formula H P -VI, Formula H P -VII, Equation H P -VIII, Formula H P -IX and H P The structure of any one of -X:
[0529]
[0530] as well as
[0531] One or more second chemical parts, each comprising, according to formula H P -XI, Formula H P -XII, Formula H P -XIII, formula H P -XIV, Formula H P -XV, Formula H P -XVI, Formula H P -XVII, Formula H P -XVIII and H P The structure of any one of -XIX, or by means of equation H P -XI, Formula H P -XII, Formula H P -XIII, formula H P -XIV, Formula H P -XV, Formula H P -XVI, H P -XVII, Formula H P -XVIII and H P The structure of any one of -XIX:
[0532]
[0533]
[0534] Among them, the p-based main material H P Each of at least one of the second chemical parts is connected to the first chemical part via a single bond represented by the dashed line in the above formula;
[0535] in,
[0536] Z 1 Each time they appear, they are independently selected from the direct connection key, C(R) II 2. C = C(R) II 2. C=O, C=NR II NR II O, Si(R) II)2, a group consisting of S, S(O) and S(O)2;
[0537] R I Each time it appears, it is an independent bonding site that connects the first chemical part to the second chemical part, or is selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: Me; i Pr; t Bu; and Ph;
[0538] Among them, at least one R I These are the bonding sites that connect the first chemical part to the single bond of the second chemical part;
[0539] R II Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: Me; i Pr; t Bu; and Ph;
[0540] Wherein, two or more adjacent substituents R II Optionally, an aliphatic, aromatic, or heteroaromatic carbocyclic or heterocyclic system can be formed, such that, according to formula H... P -XI, Formula H P -XII, Formula H P -XIII, formula H P -XIV, Formula H P -XV, Formula H P -XVI, H P -XVII, Formula H P -XVIII and H P -XIX fused ring systems consisting of structures of any one of them and optionally adjacent substituents R II The additional rings formed comprise a total of 3 to 60 carbon atoms, preferably 12 to 60 carbon atoms, and more preferably 14 to 32 carbon atoms.
[0541] In even more preferred embodiments of the invention, Z 1 Each time it appears, it is a direct bond, and the adjacent substituent R II They do not combine to form additional ring systems.
[0542] In even more preferred embodiments of the invention, p-body H may optionally be included in the organic electroluminescent device according to the invention. P Selected from the group consisting of the following structures:
[0543]
[0544]
[0545]
[0546] In a preferred embodiment of the invention, the n-body H is optionally included in any one of at least one light-emitting layer B (consisting of one (sub)layer or including more than one sub) as a whole. N Including according to formula H N -I, Formula H N -II and H N -The structure of any one of -III, or by means of formula H N -I, Formula H N -II and H N The structural composition of any one of -III:
[0547]
[0548] Among them, R III and R IV Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; Ph, optionally substituted with one or more substituents independently selected from the group consisting of: Me; i Pr; tBu; and Ph; and from formula H N -IV, Formula H N -V, Formula H N -VI, Formula H N -VII, Equation H N -VIII, Formula H N -IX, Formula H N -X, Formula H N -XI, Formula H N -XII, Formula H N -XIII and H N The structure of any representation of -XIV:
[0549]
[0550] in,
[0551] The dashed line indicates that it will be based on formula H N-IV, Formula H N -V, Formula H N -VI, Formula H N -VII, Equation H N -VIII, Formula H N -IX, Formula H N -X, Formula H N -XI, Formula H N -XII, Formula H N -XIII and H N The structure of any one of -XIV is connected according to formula H N -I, Formula H N -II and H N The binding site of the single bond in the structure of any of -III;
[0552] X 1 Is it oxygen (O), sulfur (S), or carbon (R)? V )2;
[0553] R V Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: Me; i Pr; t Bu; and Ph;
[0554] Wherein, two or more adjacent substituents R V Optionally, an aliphatic, aromatic, or heteroaromatic carbocyclic or heterocyclic system can be formed, such that, according to formula H... N -IV, Formula H N -V, Formula H N -VI, Formula H N -VII, Equation H N -VIII, Formula H N -IX, Formula H N -X, Formula H N -XI, Formula H N -XII, Formula H N -XIII and H N A fused ring system consisting of the structure of any one of the -XIVs and optionally of adjacent substituents R V The additional rings formed comprise a total of 8 to 60 carbon atoms, preferably 12 to 40 carbon atoms, and more preferably 14 to 32 carbon atoms; and
[0555] Among them, in equation H N -I and formula H NIn -II, at least one substituent R III It's CN.
[0556] In even more preferred embodiments of the invention, an n-body H may optionally be included in the organic electroluminescent device according to the invention. N Selected from the group consisting of the following structures:
[0557]
[0558]
[0559] In one embodiment of the invention, the n-body H is included in any light-emitting layer B of the organic electroluminescent device according to the invention. N It does not contain any phosphine oxide groups, and specifically, n-body H N It is not bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO).
[0560] (Multiple) TADF materials E B
[0561] According to the invention, thermally activated delayed fluorescence (TADF) material E B The characteristic is that it exhibits a ΔE of less than 0.4 eV (preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, or even less than 0.05 eV). ST The value, the ΔE ST The value is the same as the lowest excited singlet state energy level E(S1). E ) and the lowest excited triplet energy level E(T1) E The energy difference between them corresponds to this. Therefore, according to the invented TADF material E B ΔE ST Small enough to allow the lowest excited singlet state S1 at room temperature (RT, i.e., approximately 20 °C). E From the lowest excited triplet state T1 E Thermal repopulation (also known as upward intersystem crossing or reverse intersystem crossing, RISC).
[0562] Preferably, in the context of this invention, the TADF material reaches emission S1 E Transient fluorescence is observed in the T1 state due to recombination of charge carriers (holes and electrons), and fluorescence is also observed via thermally activated RISC from T1. E State reaches launch S1 E Delayed fluorescence is observed in the state.
[0563] It is understood that the small FWHM emitter S included in the light-emitting layer B of the organic electroluminescent device according to the inventionB It can also optionally have a ΔE of less than 0.4 eV. ST The value is high, and it exhibits thermally activated delayed fluorescence (TADF). However, for any small FWHM emitter S in the context of the invention... B This is only an optional feature.
[0564] In a preferred embodiment of the invention, (when measuring two spectra under comparable conditions) in at least one TADF material E B The emission spectrum of the at least one small FWHM emitter S B There is spectral overlap between the absorption spectra. In this case, at least one TADF material E B Energy can be transferred to at least one small FWHM emitter S B .
[0565] According to the invention, TADF material E B It exhibits maximum emission in the visible wavelength range of 380 nm to 800 nm, typically at room temperature (i.e., approximately 20 °C) using 10% by weight of TADF material in poly(methyl methacrylate) PMMA. B Measurement.
[0566] In one embodiment of the invention, each TADF material E B It exhibits a maximum emission in the deep blue wavelength range of 380 nm to 470 nm (preferably 400 nm to 470 nm), typically at room temperature (i.e., approximately 20 °C) using 10% by weight of TADF material in poly(methyl methacrylate) PMMA. B Measurement.
[0567] In one embodiment of the invention, each TADF material E B It exhibits a maximum emission in the green wavelength range of 480 nm to 560 nm (preferably 500 nm to 560 nm), typically at room temperature (i.e., approximately 20 °C) using 10% by weight of TADF material in poly(methyl methacrylate) PMMA. B Measurement.
[0568] In one embodiment of the invention, each TADF material E B It exhibits a maximum emission in the red wavelength range of 600 nm to 665 nm (preferably 610 nm to 665 nm), typically at room temperature (i.e., approximately 20 °C) using 10% by weight of TADF material in poly(methyl methacrylate) PMMA. B Measurement.
[0569] In a preferred embodiment of the invention, within the context of this invention, the TADF material EB The maximum emission value (peak emission) is lower than that of the smaller FWHM emitter S B The maximum emission (peak emission) is at a shorter wavelength.
[0570] In a preferred embodiment of the invention, each TADF material E B It is an organic TADF material, which, in the context of the invention, means that it does not contain any transition metals. Preferably, each TADF material E according to the invention B It is mainly composed of the elements hydrogen (H), carbon (C) and nitrogen (N), but may also include, for example, oxygen (O), boron (B), silicon (Si), fluorine (F) and bromine (Br).
[0571] In a preferred embodiment of the invention, each TADF material E B It has a molecular weight equal to or less than 800 g / mol.
[0572] In one embodiment of the invention, TADF material E B Exhibiting a photoluminescent quantum yield (PLQY) equal to or greater than 30%, typically at room temperature (i.e., approximately 20 °C) in poly(methyl methacrylate) PMMA using 10% by weight of TADF material E B Measurement.
[0573] In a preferred embodiment of the invention, the TADF material E B Exhibiting a photoluminescent quantum yield (PLQY) equal to or greater than 50%, typically at room temperature (i.e., approximately 20 °C) in poly(methyl methacrylate) PMMA using 10% by weight of TADF material E B Measurement.
[0574] In even more preferred embodiments of the invention, the TADF material E B Exhibiting a photoluminescent quantum yield (PLQY) equal to or greater than 70%, typically at room temperature (i.e., approximately 20 °C) in poly(methyl methacrylate) PMMA using 10% by weight of TADF material E B Measurement.
[0575] In one embodiment of the invention, at least one TADF material E B (Preferably, each TADF material E) B ):
[0576] (i) Characterized by exhibiting a ΔE less than 0.4 eV. ST The value, the ΔE ST The value is the same as the lowest excited singlet state energy level E(S1). E ) and the lowest excited triplet energy level E(T1) EThe energy difference between them corresponds to; and
[0577] (ii) Shows a photoluminescence quantum yield (PLQY) greater than 30%.
[0578] In one embodiment of the invention, each TADF material E B The lowest unoccupied molecular orbital LUMO (E B Energy E LUMO (E B It is less than -2.6 eV.
[0579] Those skilled in the art know how to design TADF material E according to the invention. B And the structural features typically exhibited by such molecules. In short, to promote reverse intersystem crossing (RISC), ΔE is usually reduced. ST In the context of this invention, as described above, ΔE ST Less than 0.4 eV. This is typically achieved by designing TADF materials. B This is achieved by spatially separating the HOMO and LUMO on the (electron) donor and (electron) acceptor groups, respectively. These groups are typically bulky or connected via helical linkages, causing them to twist and reducing the spatial overlap between the HOMO and LUMO. However, minimizing the spatial overlap between the HOMO and LUMO also leads to a decrease in the photoluminescence quantum yield (PLQY) of the TADF material, which is detrimental. Therefore, in practice, both effects are considered to achieve ΔE ST The reduction and high PLQY.
[0580] A common method for designing TADF materials is to covalently attach one or more (electron) donor portions with HOMO distributed thereon and one or more (electron) acceptor portions with LUMO distributed thereon to the same bridge, referred to here as a linking group. TADF material E B It may also include, for example, two or three linking groups that bind to the same receptor moiety, and additional donor and receptor moieties may bind to each of the two or three linking groups.
[0581] One or more donor portions and one or more acceptor portions can also bind directly to each other (in the absence of a linker group).
[0582] Typical donor moieties are diphenylamine, carbazole, acridine, phenoxazine, and derivatives of related structures.
[0583] Benzene derivatives, biphenyl derivatives, and to some extent terphenyl derivatives are common linking groups.
[0584] Nitrile groups are very common acceptor moieties in TADF materials, and known examples include the following components:
[0585] (i) Carbazole dicyanobenzene compounds
[0586] Such as 2CzPN (4,5-bis(9H-carbazole-9-yl)phthalonitrile), DCzIPN (4,6-bis(9H-carbazole-9-yl)isophthalonitrile), 4CzPN (3,4,5,6-tetra(9H-carbazole-9-yl)phthalonitrile), 4CzIPN (2,4,5,6-tetra(9H-carbazole-9-yl)isophthalonitrile), 4CzTPN (2,4,5,6-tetra(9H-carbazole-9-yl)terephthalonitrile) and their derivatives;
[0587] (ii) Carbazolylcyanopyridine compounds
[0588] Such as 4CzCNPy (2,3,5,6-tetra(9H-carbazole-9-yl)-4-cyanopyridine) and its derivatives;
[0589] (iii) Carbazole-cyanobiphenyl compounds
[0590] Such as CNBPCz(4,4',5,5'-tetra(9H-carbazole-9-yl)-[1,1'-biphenyl]-2,2'-dicarboxylonitrile), CzBPCN(4,4',6,6'-tetra(9H-carbazole-9-yl)-[1,1'-biphenyl]-3,3'-dicarboxylonitrile), DDCzIPN(3,3',5,5'-tetra(9H-carbazole-9-yl)-[1,1'-biphenyl]-2,2',6,6'-tetracarboxylonitrile) and their derivatives;
[0591] In these materials, one or more nitrile groups can be replaced by fluorine (F) or trifluoromethyl (CF3) as the acceptor moiety.
[0592] Nitrogen heterocycles such as triazine derivatives, pyrimidine derivatives, triazole derivatives, oxadiazole derivatives, thiadiazole derivatives, heptaazine derivatives, 1,4-diazabenzo[9,10]phenanthrene derivatives, benzothiazole derivatives, benzoxazole derivatives, quinoxaline derivatives, and diazafluorene derivatives are also known acceptor moieties used to construct TADF materials. Known examples of TADF materials, including, for example, triazine receptors, include PIC-TRZ(7,7'-(6-([1,1'-biphenyl]-4-yl)-1,3,5-triazine-2,4-diyl)bis(5-phenyl-5,7-dihydroindolo[2,3-b]carbazole)), mBFCzTrz(5-(3-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)-5H-benzofurano[3,2-c]carbazole) and DCzTrz(9,9'-(5-(4,6-diphenyl-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole)).
[0593] Another group of TADF materials includes diaryl ketones such as benzophenone or (heteroaryl)aryl ketones such as 4-benzoylpyridine, 9,10-anthraquinone, 9H-xanthon-9-one and their derivatives as the acceptor moiety, and a donor moiety (usually carbazole-substituent) bound to the acceptor moiety. Examples of such TADF materials include BPBCz(bis(4-(9'-phenyl-9H,9'H-[3,3'-dicarbazole]-9-yl)phenyl) ketone), mDCBP((3,5-bis(9H-carbazole-9-yl)phenyl)(pyridin-4-yl) ketone), AQ-DTBu-Cz(2,6-bis(4-(3,6-di-tert-butyl-9H-carbazole-9-yl)phenyl)anthracene-9,10-dione) and MCz-XT(3-(1,3,6,8-tetramethyl-9H-carbazole-9-yl)-9H-xanthone-9-one).
[0594] Sulfoxide (specifically, diphenyl sulfoxide) is also commonly used as the acceptor moiety for constructing TADF materials, and known examples include 4-PC-DPS (9-phenyl-3-(4-(phenylsulfonyl)phenyl)-9H-carbazole), DitBu-DPS (9,9'-(sulfonylbis(4,1-phenylene))bis(9H-carbazole)) and TXO-PhCz (2-(9-phenyl-9H-carbazole-3-yl)-9H-thioxanthone-9-one 10,10-dioxide).
[0595] Exemplarily, all groups of the above-described TADF materials can provide suitable TADF materials E for use according to the present invention. B Assuming a specific material meets the above basic requirements, that is, ΔE ST The value is less than 0.4 eV.
[0596] Those skilled in the art will understand that, in the context of this invention, not only the above-described structure, but also other materials can be suitable TADF materials. B Those skilled in the art are familiar with the design principles of such molecules and also know how to design such molecules with a specific emission color (e.g., blue, green, or red emission).
[0597] Information: H. Tanaka, K. Shizu, H. Nakanotani, C. Adachi, Chemistry of Materials2013,25(18),3766,DOI:10.1021 / cm402428a;J.Li,T.Nakagawa,J.MacDonald,Q.Zhang,H.Nomura,H.Miyazaki,C.Adachi,Advanced Materials2013,25(24),3319,DOI:10.1002 / adma.201300575;K.Nasu,T.Nakagawa,H.Nomura,C.-J.Lin,C.-H.Cheng,M.-R.Tseng,T.Yasudaad,C.Adachi,Chemical Communications 2013,49(88),10385,DOI:10.1039 / c3cc44179b;Q.Zhang,B.Li1,S.Huang,H.Nomura,H.Tanaka,C.Adachi,Nature Photonics2014,8(4),326,DOI:10.1038 / nphoton.2014.12;B.Wex,BRKafarani,Journal ofMaterials Chemistry C 2017,5,8622,DOI:10.1039 / c7tc02156a;Y.Im,M.Kim,YJCho,J.-A.Seo,KSYook,JYLee,Chemistry of Materials 2017,29(5),1946,DOI:10.1021 / acs.chemmater.6b05324;T.-T.Bui,F.Goubard,M.Ibrahim-Ouali,D.Gigmes,F.Dumur,Beilstein Journal of Organic Chemistry 2018,14,282,DOI:10.3762 / bjoc.14.18;X.Liang,Z.-L.Tu,Y.-X.Zheng,Chemistry–A European Journal 2019,25(22),5623;
[0598] Furthermore, for example, US2015105564(A1), US2015048338(A1), US2015141642(A1), US2014336379(A1), US2014138670(A1), US2012241732(A1), EP3315581(A1), EP3483156(A1), and US2018053901(A1) disclose TADF materials E that can be used in organic electroluminescent devices according to the present invention. B It is understood that this does not imply that the invention is limited to the organic electroluminescent devices comprising TADF materials disclosed in the cited references. It is also understood that any TADF material used in the prior art can be a suitable TADF material in the context of this invention. B .
[0599] In one embodiment of the invention, each TADF material E B It includes one or more chemical moieties that are independently selected from the group consisting of CN, CF3 and optionally substituted 1,3,5-triazine groups.
[0600] In one embodiment of the invention, each TADF material E B It includes one or more chemical moieties selected independently from the group consisting of CN and optionally substituted 1,3,5-triazine groups.
[0601] In one embodiment of the invention, each TADF material E B Includes one or more optionally substituted 1,3,5-triazine groups.
[0602] In one embodiment of the invention, each TADF material E B It includes one or more chemical moieties independently selected from amino, indolyl, carbazole and their derivatives (all of which may optionally be substituted), wherein these groups may be attached to the core structure of the corresponding TADF material via nitrogen (N) or via carbon (C) atoms, and wherein the substituents attached to these groups may form monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic systems.
[0603] In a preferred embodiment of the invention, at least one TADF material E B (Preferably, each TADF material E) B It includes the following components:
[0604] One or more first chemical moieties, independently selected from amino, indole, carbazole, and their derivatives (all of which may optionally be substituted), wherein these groups may be incorporated into the core structure of the corresponding TADF material via nitrogen (N) or via carbon (C) atoms, and wherein the substituents incorporated into these groups may form monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic systems; and
[0605] One or more second chemical moieties, independently selected from the group consisting of CN, CF3 and optionally substituted 1,3,5-triazine groups.
[0606] In even more preferred embodiments of the invention, at least one TADF material E B (Preferably, each TADF material E) B It includes the following components:
[0607] One or more first chemical moieties, independently selected from amino, indole, carbazole, and their derivatives (all of which may optionally be substituted), wherein these groups may be incorporated into the core structure of the corresponding TADF material via nitrogen (N) or via carbon (C) atoms, and wherein the substituents incorporated into these groups may form monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic systems; and
[0608] One or more second chemical moieties, independently selected from the group consisting of CN and optionally substituted 1,3,5-triazine groups.
[0609] In even more preferred embodiments of the invention, at least one TADF material E B (Preferably, each TADF material E) B It includes the following components:
[0610] One or more first chemical moieties, independently selected from amino, indole, carbazole, and their derivatives (all of which may optionally be substituted), wherein these groups may be incorporated into the core structure of the corresponding TADF material via nitrogen (N) or via carbon (C) atoms, and wherein the substituents incorporated into these groups may form monocyclic or polycyclic aliphatic or aromatic, carbocyclic or heterocyclic systems; and
[0611] One or more optionally substituted 1,3,5-triazine groups.
[0612] Those skilled in the art will know that the expression "its derivatives" means that the corresponding parent structure can be optionally substituted, or that any atom within the corresponding parent structure can be replaced, for example, by an atom of another element.
[0613] In one embodiment of the invention, the organic electroluminescent device includes at least one light-emitting layer B, said at least one light-emitting layer B comprising the following components:
[0614] (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H );and
[0615] (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P );and
[0616] (iii) At least one small half-peak full width at half maximum (FWHM) emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and
[0617] (iv) At least one thermally activated delayed fluorescence (TADF) material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ),
[0618] The relationship represented by the following equations (1) and (2) applies:
[0619] E(T1 H )>E(T1 P (1)
[0620] E(T1 H )>E(T1 E (2),
[0621] Among them, each TADF material E B It comprises the following components: one or more first chemical moieties, independently selected from amino, indolyl, carbazolyl and their derivatives (all of which may optionally be substituted), wherein these groups may be attached to the core structure of the corresponding TADF material via nitrogen (N) or via carbon (C) atoms, and wherein the substituents attached to these groups may form a monocyclic or polycyclic aliphatic or aromatic, carbocyclic or heterocyclic system; and one or more second chemical moieties, independently selected from the group consisting of CN and optionally substituted 1,3,5-triazine groups.
[0622] In one embodiment of the invention, each TADF material E B Includes the following components:
[0623] One or more first chemical parts, each comprising or consisting of a structure according to formula DI:
[0624]
[0625] and
[0626] Optionally, one or more second chemical moieties are each independently selected from CN, CF3, and structures according to any one of Formula AI, Formula A-II, Formula A-III, and Formula A-IV:
[0627]
[0628] as well as
[0629] A third chemical part comprises a structure according to any one of formula LI, formula L-II, formula L-III, formula L-IV, formula LV, formula L-VI, formula L-VII, and formula L-VIII, or consists of a structure according to any one of formula LI, formula L-II, formula L-III, formula L-IV, formula LV, formula L-VI, formula L-VII, and formula L-VIII:
[0630]
[0631]
[0632] in,
[0633] One or more first chemical parts and one or more second chemical parts are covalently bonded to a third chemical part via single bonds;
[0634] In formula DI:
[0635] # indicates the binding site where the corresponding first chemical part of formula DI is connected to the single bond of the third chemical part;
[0636] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C = CR 1 R 2 C=O, C=NR 1 NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0637] R a R b R d R 1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 3 )2; OR 3 ;Si(R) 3 )3;B(OR 3 )2; OSO2R 3 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 3 And wherein, one or more non-adjacent CH2 groups are optionally R 3 C = CR 3 C≡C, Si(R) 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 、P(=O)(R 3 SO, SO2, NR 3 O, S or CONR 3 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 3 And wherein, one or more non-adjacent CH2 groups are optionally R 3 C = CR 3 C≡C, Si(R) 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 P(=O)(R) 3 SO, SO2, NR 3 O, S or CONR 3 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 3 And wherein, one or more non-adjacent CH2 groups are optionally R 3 C = CR 3 C≡C, Si(R) 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 P(=O)(R) 3SO, SO2, NR 3 O, S or CONR 3 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 3 And wherein, one or more non-adjacent CH2 groups are optionally R 3 C = CR 3 C≡C, Si(R) 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 P(=O)(R) 3 SO, SO2, NR 3 O, S or CONR 3 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 3 And wherein, one or more non-adjacent CH2 groups are optionally R 3 C = CR 3 C≡C, Si(R) 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 P(=O)(R) 3 SO, SO2, NR 3 O, S or CONR 3 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 3 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 3 ;
[0638] R 3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 4 )2; OR 4 ;Si(R) 4 )3;B(OR 4 )2; OSO2R 4 ;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 4 And wherein, one or more non-adjacent CH2 groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 P(=O)(R) 4 SO, SO2, NR 4 O, S or CONR 4 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 4 And wherein, one or more non-adjacent CH2 groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 P(=O)(R) 4 SO, SO2, NR 4 O, S or CONR 4 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 4 And wherein, one or more non-adjacent CH2 groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 P(=O)(R) 4 SO, SO2, NR 4 O, S or CONR 4 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 4 And wherein, one or more non-adjacent CH2 groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 P(=O)(R) 4 SO, SO2, NR 4 O, S or CONR 4 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 4And wherein, one or more non-adjacent CH2 groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 P(=O)(R) 4 SO, SO2, NR 4 O, S or CONR 4 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 4 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 4 ;
[0639] Optionally, any substituent R a R b R d R 1 R 2 R 3 and R 4 Independent of each other and selected from R a R b R d R 1 R 2 R 3 and R 4 One or more adjacent substituents form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic carbocyclic or heterocyclic and / or benzofused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents R. 5 ;
[0640] R 4 and R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C6-C 18Aryl group, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, C1-C5 alkyl, Ph, or CN; C3-C 17 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, Ph or C1-C5 alkyl; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);
[0641] a is an integer and is either 0 or 1;
[0642] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0643] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0644] Among them, in formulas A-1, A-2, A-3, and A-4:
[0645] The dashed line represents a single bond that connects the corresponding second chemical part to the third chemical part according to formula AI, formula A-II, formula A-III or formula A-IV;
[0646] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1 It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1 At least one of them is CR 7 ;
[0647] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0648] R 6 and R 8 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 9 )2; OR 9 ;Si(R) 9 )3;B(OR 9)2; OSO2R 9 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 9 And wherein, one or more non-adjacent CH2 groups are optionally R 9 C = CR 9 C≡C, Si(R) 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 P(=O)(R) 9 SO, SO2, NR 9 O, S or CONR 9 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 9 And wherein, one or more non-adjacent CH2 groups are optionally R 9 C = CR 9 C≡C, Si(R) 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 P(=O)(R) 9 SO, SO2, NR 9 O, S or CONR 9 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 9 And wherein, one or more non-adjacent CH2 groups are optionally R 9 C = CR 9 C≡C, Si(R) 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 P(=O)(R) 9 SO, SO2, NR 9 O, S or CONR 9 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 9 And wherein, one or more non-adjacent CH2 groups are optionally R 9 C = CR 9 C≡C, Si(R) 9 )2、Ge(R 9)2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 P(=O)(R) 9 SO, SO2, NR 9 O, S or CONR 9 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 9 And wherein, one or more non-adjacent CH2 groups are optionally R 9 C = CR 9 C≡C, Si(R) 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 P(=O)(R) 9 SO, SO2, NR 9 O, S or CONR 9 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 9 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 9 ;
[0649] R 9 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 10 )2; OR 10 ;Si(R) 10 )3;B(OR 10 )2; OSO2R 10 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 10 And wherein, one or more non-adjacent CH2 groups are optionally R 10 C = CR 10 C≡C, Si(R) 10 )2、Ge(R 10 )2、Sn(R 10 )2. C=O, C=S, C=Se, C=NR 10 P(=O)(R) 10 SO, SO2, NR 10 O, S or CONR 10 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 10And wherein, one or more non-adjacent CH2 groups are optionally R 10 C = CR 10 C≡C, Si(R) 10 )2、Ge(R 10 )2、Sn(R 10 )2. C=O, C=S, C=Se, C=NR 10 P(=O)(R) 10 SO, SO2, NR 10 O, S or CONR 10 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 10 And wherein, one or more non-adjacent CH2 groups are optionally R 10 C = CR 10 C≡C, Si(R) 10 )2、Ge(R 10 )2、Sn(R 10 )2. C=O, C=S, C=Se, C=NR 10 P(=O)(R) 10 SO, SO2, NR 10 O, S or CONR 10 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 10 And wherein, one or more non-adjacent CH2 groups are optionally R 10 C = CR 10 C≡C, Si(R) 10 )2、Ge(R 10 )2、Sn(R 10 )2. C=O, C=S, C=Se, C=NR 10 P(=O)(R) 10 SO, SO2, NR 10 O, S or CONR 10 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 10 And wherein, one or more non-adjacent CH2 groups are optionally R 10 C = CR 10 C≡C, Si(R) 10 )2、Ge(R 10 )2、Sn(R 10 )2. C=O, C=S, C=Se, C=NR 10 P(=O)(R) 10 SO, SO2, NR10 O, S or CONR 10 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 10 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 10 ;
[0650] R 10 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally independently substituted with deuterium, CN, CF3 or F; C6-C 18 Aryl group, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, C1-C5 alkyl, Ph, or CN; C3-C 17 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, Ph or C1-C5 alkyl; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);
[0651] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0652]
[0653] Among them, R X For example, R 6 The definition is based on the premise that at least one group R in formula EWG-I is present. X It is CN or CF3;
[0654] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, one or more substituents R are substituted. 10Aromatic rings; wherein, optionally, the fused ring system thus formed comprises a total of 9 to 18 ring atoms;
[0655] Among them, in formulas LI, L-II, L-III, L-IV, LV, L-VI, L-VII, and L-VIII:
[0656] Q 3 Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0657] R 11 Each occurrence is independently a bonding site that connects the first or second chemical part to the third chemical part via a single bond, or independently selected from the group consisting of: hydrogen; deuterium; F; Cl; Br; I; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; and C6-C 18 aryl, wherein one or more hydrogen atoms are optionally independently surrounded by deuterium, C1-C5 alkyl, C6-C 18 Aryl, F, Cl, Br and I substitution;
[0658] R 12 For example, R 6 Defined;
[0659] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11 The quantity of each TADF material is limited, under the above conditions. B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0660] In a preferred embodiment of the invention,
[0661] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C = CR 1 R 2 C=O, C=NR 1 NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0662] R a R b R d R1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 3 )2; OR 3 ;Si(R) 3 )3;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 3 And wherein, one or more non-adjacent CH2 groups are optionally R 3 C = CR 3 C≡C, Si(R) 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 P(=O)(R) 3 SO, SO2, NR 3 O, S or CONR 3 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 3 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 3 ;
[0663] R 3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 4 )2; OR 4 ;Si(R) 4 )3;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 4 And wherein, one or more non-adjacent CH2 groups are optionally R 4 C = CR 4 C≡C, Si(R) 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 P(=O)(R) 4 SO, SO2, NR 4 O, S or CONR 4 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 4 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R4 ;
[0664] Optionally, the substituent R a R b R d R 1 R 2 R 3 and R 4 Each of them independently of each other and selected from R a R b R d R 1 R 2 R 3 and R 4 One or more adjacent substituents form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic carbocyclic or heterocyclic and / or benzofused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents R. 5 ;
[0665] R 4 and R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C6-C 18 Aryl group, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, C1-C5 alkyl, Ph, or CN; C3-C 17 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, C1-C5 alkyl, or Ph; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);
[0666] a is an integer and is either 0 or 1;
[0667] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0668] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0669] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1 At least one of them is CR 7 ;
[0670] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0671] R 6 and R 8 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 9 )2; OR 9 ;Si(R) 9 )3;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 9 And wherein, one or more non-adjacent CH2 groups are optionally R 9 C = CR 9 C≡C, Si(R) 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 P(=O)(R) 9 SO, SO2, NR 9 O, S or CONR 9 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 9 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 9 ;
[0672] R 9 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 10 )2; OR 10 ;Si(R) 10 )3;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 10 And wherein, one or more non-adjacent CH2 groups are optionally R 10 C = CR10 C≡C, Si(R) 10 )2、Ge(R 10 )2、Sn(R 10 )2. C=O, C=S, C=Se, C=NR 10 P(=O)(R) 10 SO, SO2, NR 10 O, S or CONR 10 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 10 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 10 ;
[0673] R 10 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C6-C 18 Aryl group, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, C1-C5 alkyl, Ph, or CN; C3-C 17 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, C1-C5 alkyl, or Ph; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);
[0674] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0675]
[0676] Among them, R X For example, R 6 The definition presupposes that at least one group R X It is CN or CF3;
[0677] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, one or more substituents R are substituted. 10 Aromatic rings; wherein, optionally, the fused ring system thus formed comprises a total of 9 to 18 ring atoms;
[0678] Q3 Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0679] R 11 Each time it appears, it is independently a bonding site that connects the first or second chemical part to the third chemical part via a single bond, or independently selected from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; and C6-C 18 aryl, wherein one or more hydrogen atoms are optionally independently surrounded by deuterium, C1-C5 alkyl and C6-C 18 Aryl substitution;
[0680] R 12 For example, R 6 Defined;
[0681] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11 The quantity) is limited (preferably, under the above conditions, the quantity of each TADF material E B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0682] In even more preferred embodiments of the invention,
[0683] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C = CR 1 R 2 C=O, C=NR 1 NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0684] R a R b R d R 1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 3 )2; OR 3 ;Si(R) 3 )3; CF3; CN; F; Cl; Br; I; C1-C5 alkyl, optionally substituted with one or more substituents R 3C6-C 18 aryl, optionally substituted with one or more substituents R 3 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 3 ;
[0685] R 3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 4 )2;Si(R 4 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 4 C6-C 18 aryl, optionally substituted with one or more substituents R 4 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 4 ;
[0686] Optionally, the substituent R a R b R d R 1 R 2 and R 3 Each of them independently of each other and selected from R a R b R d R 1 R 2 and R 3 One or more adjacent substituents form a monocyclic or polycyclic aliphatic, aromatic, or heteroaromatic carbocyclic or heterocyclic and / or benzofused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents R. 5 ;
[0687] R 4 and R 5 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; CF3; CN; F; Me; i Pr; t Bu; N(Ph)2; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0688] a is an integer and is either 0 or 1;
[0689] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0690] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0691] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1 It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1 At least one of them is CR 7 ;
[0692] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0693] R 6 and R 8 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 9 )2; OR 9 ;Si(R) 9 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 9 C6-C 18 aryl, optionally substituted with one or more substituents R 9 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 9 ;
[0694] R 9 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 10 )2; OR 10 ;Si(R) 10 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 10 C6-C 18 aryl, optionally substituted with one or more substituents R 10 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 10 ;
[0695] R 10Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CF3; CN; F; N(Ph)2; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu, Ph, CN, CF3 or F can be substituted.
[0696] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0697]
[0698] Among them, R X For example, R 6 The definition presupposes that at least one group R X It is CN or CF3;
[0699] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, one or more substituents R are substituted. 10 Aromatic rings; wherein, optionally, the fused ring system thus formed comprises a total of 9 to 18 ring atoms;
[0700] Q 3 Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0701] R 11 Each time it appears, it is independently a bonding site that connects the first or second chemical part to the third chemical part via a single bond, or independently selected from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; and C6-C 18 Aryl group, optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; i Pr; t Bu; and Ph;
[0702] R 12 For example, R 6 Defined;
[0703] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11The quantity) is limited (preferably, under the above conditions, the quantity of each TADF material E B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0704] In even more preferred embodiments of the invention,
[0705] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C=O, NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0706] R a R b R d R 1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 3 )2; OR 3 ;Si(R) 3 )3; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 3 C6-C 18 aryl, optionally substituted with one or more substituents R 3 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 3 ;
[0707] R 3 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; CF3; CN; F; Me; i Pr; t Bu; N(Ph)2; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0708] Optionally, the substituent R a R b R d R 1 and R 2 Each of them independently of each other and selected from R a R b R d R 1 and R 2One or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic and / or benzofused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents, said one or more substituents being independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; F; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0709] The fused ring system, optionally formed by the structure according to formula DI and the attached ring formed by adjacent substituents, comprises a total of 13 to 30 ring atoms, preferably 16 to 30 ring atoms.
[0710] a is an integer and is either 0 or 1;
[0711] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0712] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0713] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1 It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1 At least one of them is CR 7 ;
[0714] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0715] R 6 and R 8 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 9 )2; OR 9 ;Si(R) 9)3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 9 C6-C 18 aryl, optionally substituted with one or more substituents R 9 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 9 ;
[0716] R 9 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CF3; CN; F; N(Ph)2; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu, Ph, CN, CF3 or F are substitutes;
[0717] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0718]
[0719] Among them, R X For example, R 6 The definition presupposes that at least one group R X It is CN or CF3;
[0720] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, an aromatic ring with one or more substituents is substituted, wherein the one or more substituents are independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CF3; CN; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Replace with Bu, Ph, CN or CF3;
[0721] The fused ring system formed in this way can optionally include a total of 9 to 18 ring atoms;
[0722] Q 3 Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0723] R 11Each time they appear, they are independently bond sites that connect the first or second chemical part to the third chemical part, or independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; i Pr; t Bu; and Ph;
[0724] R 12 For example, R 6 Defined;
[0725] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11 The quantity) is limited (preferably, under the above conditions, the quantity of each TADF material E B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0726] In even more preferred embodiments of the invention,
[0727] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C=O, NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0728] R a R b and R d Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 3 )2; OR 3 ;Si(R) 3 )3; CF3; CN; Me; i Pr; t Bu;Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph substitution; carbazoyl group, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr、 t Bu and Ph substitution; triazine group, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr、 tBu and Ph substitution; pyrimidinyl group, wherein one or more hydrogen atoms are optionally and independently replaced by deuterium, Me, i Pr、 t Bu and Ph substitutions; and pyridyl groups, wherein one or more hydrogen atoms are optionally and independently replaced by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0729] R 1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 3 )2; OR 3 ;Si(R) 3 )3; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 3 C6-C 18 aryl, optionally substituted with one or more substituents R 3 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 3 ;
[0730] R 3 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; CF3; CN; F; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0731] Optionally, the substituent R a R b R d R 1 and R 2 Each of them independently of each other and selected from R a R b R d R 1 and R 2 One or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic and / or benzofused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents, said one or more substituents being independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; F; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me,i Pr、 t Bu and Ph are replaced;
[0732] The fused ring system, optionally formed by the structure according to formula DI and the attached ring formed by adjacent substituents, comprises a total of 13 to 30 ring atoms, preferably 16 to 30 ring atoms.
[0733] a is an integer and is either 0 or 1;
[0734] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0735] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0736] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1 It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1 At least one of them is CR 7 ;
[0737] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0738] R 6 and R 8 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 9 )2; OR 9 ;Si(R) 9 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 9 C6-C 18 aryl, optionally substituted with one or more substituents R 9 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R 9 ;
[0739] R 9Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CF3; CN; F; N(Ph)2; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu, Ph, CN, CF3 or F can be substituted.
[0740] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0741]
[0742] Among them, R X For example, R 6 The definition presupposes that at least one group R X It is CN or CF3;
[0743] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, an aromatic ring with one or more substituents is substituted, wherein the one or more substituents are independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0744] The fused ring system formed in this way can optionally include a total of 9 to 18 ring atoms;
[0745] Q 3 Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0746] R 11 Each time they appear, they are independently bond sites that connect the first or second chemical part to the third chemical part, or independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; i Pr; t Bu; and Ph;
[0747] R 12 For example, R 6 Defined;
[0748] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11 The quantity) is limited (preferably, under the above conditions, the quantity of each TADF material E B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0749] In even more preferred embodiments of the invention,
[0750] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C=O, NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0751] R a R b and R d Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 3 )2; OR 3 ;Si(R) 3 )3; CF3; CN; Me; i Pr; t Bu;Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph substitutions; and a carbazoyl group, wherein one or more hydrogen atoms are optionally and independently replaced by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0752] R 1 and R 2 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; OR 3 ;Si(R) 3 )3; C1-C5 alkyl, optionally substituted with one or more substituents R 3 ; and C6-C 18 aryl, optionally substituted with one or more substituents R 3 ;and
[0753] R 3Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; CF3; CN; F; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0754] Optionally, the substituent R a R b R d R 1 and R 2 Each of them independently of each other and selected from R a R b R d R 1 and R 2 One or more substituents form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic and / or benzo[a] fused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents, said one or more substituents being independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; F; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0755] The fused ring system, optionally formed by the structure according to formula DI and the attached ring formed by adjacent substituents, comprises a total of 13 to 30 ring atoms, preferably 16 to 30 ring atoms.
[0756] a is an integer and is either 0 or 1;
[0757] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0758] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0759] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1 It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1At least one of them is CR 7 ;
[0760] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0761] R 6 and R 8 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; OPh; N(Ph)2; Si(Me)3; Si(Ph)3; CF3; CN; F; Me; i Pr; t Bu;Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph substitutions; and a carbazoyl group, wherein one or more hydrogen atoms are optionally and independently replaced by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0762] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0763]
[0764] Among them, R X For example, R 6 The definition presupposes that at least one group R X It is CN or CF3;
[0765] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, an aromatic ring with one or more substituents is substituted, said one or more substituents being: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0766] The fused ring system formed in this way can optionally include a total of 9 to 18 ring atoms;
[0767] Q 3Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0768] R 11 Each time they appear, they are independently bond sites that connect the first or second chemical part to the third chemical part, or independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; i Pr; t Bu; and Ph;
[0769] R 12 For example, R 6 Defined;
[0770] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11 The quantity) is limited (preferably, under the above conditions, the quantity of each TADF material E B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0771] In even more preferred embodiments of the invention,
[0772] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C=O, NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0773] R a R b and R d Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; Si(Me)₃; Si(Ph)₃; CF₃; CN; Me; i Pr; t Bu;Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph substitutions; and a carbazoyl group, wherein one or more hydrogen atoms are optionally and independently replaced by deuterium, Me, i Pr、t Bu and Ph are replaced;
[0774] R 1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0775] Optionally, the substituent R a R b R d R 1 and R 2 Each of them independently of each other and selected from R a R b R d R 1 and R 2 One or more substituents form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic and / or benzo[a] fused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents, said one or more substituents being independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; F; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0776] The fused ring system, optionally formed by the structure according to formula DI and the attached ring formed by adjacent substituents, comprises a total of 13 to 30 ring atoms, preferably 16 to 30 ring atoms.
[0777] a is an integer and is either 0 or 1;
[0778] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0779] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0780] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1 At least one of them is CR 7 ;
[0781] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0782] R 6 and R 8 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; Si(Me)₃; Si(Ph)₃; Me; i Pr; t Bu;Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph substitutions; and a carbazoyl group, wherein one or more hydrogen atoms are optionally and independently replaced by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0783] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0784]
[0785] Among them, R X For example, R 6 As defined, but can also be CN or CF3, provided that at least one group R is present. X It is CN or CF3;
[0786] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, an aromatic ring with one or more substituents is substituted, said one or more substituents being: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0787] The fused ring system formed in this way can optionally include a total of 9 to 18 ring atoms;
[0788] Q 3 Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0789] R 11 Each time they appear, they are independently bond sites that connect the first or second chemical part to the third chemical part, or independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; i Pr; t Bu; and Ph;
[0790] R 12 For example, R 6 Defined;
[0791] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11 The quantity) is limited (preferably, under the above conditions, the quantity of each TADF material E B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0792] In a particularly preferred embodiment of the invention,
[0793] Z 2 Each time it appears, it is independently selected from the direct connection key and CR. 1 R 2 C=O, NR 1 O, SiR 1 R 2 A group consisting of S, S(O) and S(O)2;
[0794] R a R b and R d Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; CF3; CN; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0795] R 1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0796] Optionally, the substituent R a R b R d R 1 and R 2 Each of them independently of each other and selected from R a R b R d R 1 and R 2 One or more substituents form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic and / or benzo[a] fused ring system; wherein, optionally, the ring system thus formed may optionally be substituted with one or more substituents, said one or more substituents being independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0797] The fused ring system, optionally formed by the structure according to formula DI and the attached ring formed by adjacent substituents, comprises a total of 13 to 30 ring atoms, preferably 16 to 30 ring atoms.
[0798] a is an integer and is either 0 or 1;
[0799] b is an integer and is either 0 or 1 each time it appears, where two bs are always the same;
[0800] Wherein, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0;
[0801] Q 1 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 and CR 7 The prerequisite is that in formula AI, two adjacent groups Q 1It cannot all be nitrogen (N); where, if the group Q in formula AI... 1 If neither of them is nitrogen (N), then group Q 1 At least one of them is CR 7 ;
[0802] Q 2 Each time it appears, it is independently selected from nitrogen (N) and CR. 6 The prerequisite is that in formulas A-II and A-III, at least one group Q 2 It is nitrogen (N) and has two adjacent groups Q. 2 It cannot all be nitrogen (N);
[0803] R 6 and R 8 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; Me; i Pr; t Bu;Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph substitutions; and a carbazoyl group, wherein one or more hydrogen atoms are optionally and independently replaced by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0804] R 7 Each occurrence is independently selected from the group consisting of CN, CF3, and the structure according to EWG-I:
[0805]
[0806] Among them, R X For example, R 6 As defined, but can also be CN or CF3, provided that at least one group R is present. X It is CN or CF3;
[0807] In formula A-IV, the two adjacent groups R 8 Optionally, a structure fused to formula A-IV is formed and optionally, an aromatic ring with one or more substituents is substituted, said one or more substituents being: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr、 t Bu and Ph are replaced;
[0808] The fused ring system formed in this way can optionally include a total of 9 to 18 ring atoms;
[0809] Q 3 Each time it appears, it is independently selected from nitrogen (N) and CR. 12 The prerequisite is that there is at least one Q 3 It is nitrogen (N);
[0810] R 11 Each time they appear, they are independently bond sites that connect the first or second chemical part to the third chemical part, or independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, optionally substituted with one or more substituents independently selected from the group consisting of: deuterium; Me; i Pr; t Bu; and Ph;
[0811] R 12 For example, R 6 Defined;
[0812] The maximum number of first and second chemical parts attached to the third chemical part is only limited by the number of available binding sites on the third chemical part (in other words: substituent R). 11 The quantity) is limited (preferably, under the above conditions, the quantity of each TADF material E B It includes at least one first chemical component, at least one second chemical component, and exactly one third chemical component.
[0813] In a preferred embodiment of the invention, a is always 1 and b is always 0.
[0814] In a preferred embodiment of the invention, Z 2 It is a direct connection key every time it appears.
[0815] In a preferred embodiment of the invention, R a It is hydrogen each time it appears.
[0816] In a preferred embodiment of the invention, R a and R d It is hydrogen each time it appears.
[0817] In a preferred embodiment of the invention, Q 3 It appears as nitrogen (N) each time.
[0818] In embodiments of the invention, at least one group R in formula EWG-I X It's CN.
[0819] In a preferred embodiment of the invention, EWG-I contains exactly one R group. X It's CN.
[0820] In a preferred embodiment of the invention, EWG-I contains exactly one R group. X It is CN, and there is no R group in formula EWG-I. X It's CF3.
[0821] Examples of the first chemical part according to the invention are shown below, which of course do not imply that the invention is limited to these examples:
[0822]
[0823]
[0824]
[0825] The above definition applies to this.
[0826] Examples of the second chemical part according to the invention are shown below, which of course do not imply that the invention is limited to these examples:
[0827]
[0828]
[0829] The above definition applies to this.
[0830] In a preferred embodiment of the invention, each TADF material E B Having E B -I, formula E B -II, Formula E B -III, Formula E B -IV, Formula E B -V, Equation E B -VI, Formula E B -VII, Equation E B -VIII, Equation E B -IX, Equation E B -X and E B The structure of any representation in -XI:
[0831]
[0832]
[0833]
[0834]
[0835] in,
[0836] R 13For example, R 11 The defined prerequisite is R 13 It cannot be a bonding site that connects the first or second chemical part to a single bond of the third chemical part;
[0837] R Y Selected from CN and CF3, or R Y Includes structures according to formula BN-I or consists of structures according to formula BN-I:
[0838]
[0839] The formula BN-I is bonded to formula E via a single bond indicated by a dashed line. B -I, formula E B -II, Formula E B -III, Formula E B -IV, Formula E B -V, Equation E B -VI, Formula E B -VII, Equation E B -VIII or E B The structure is -IX, and in which exactly one R BN The group is CN, while the other two are R. BN All the radicals are hydrogen (H);
[0840] In addition to the above definitions, the above definitions also apply.
[0841] In a preferred embodiment of the invention, R 13 It is hydrogen each time it appears.
[0842] In one embodiment of the invention, R Y It appears as CN each time.
[0843] In one embodiment of the invention, R Y It appears as CF3 each time.
[0844] In one embodiment of the invention, R Y Each time it appears, it is represented by the structure BN-I.
[0845] In a preferred embodiment of the invention, R Y Each occurrence is independently selected from CN and the structure represented by formula BN-I.
[0846] In a preferred embodiment of the invention, each TADF material E B Having E B -I, formula E B -II, Formula E B -III, Formula E B -IV, Formula EB -V, Equation E B -VI, Formula E B -VII and Equation E B -X represents any structure, where the above definition applies.
[0847] In a preferred embodiment of the invention, each TADF material E B Having E B -I, formula E B -III, Formula E B -V, Equation E B -VI and E B -X represents any structure, where the above definition applies.
[0848] The following lists the TADF material E used in the organic electroluminescent device according to the invention. B Examples are provided, however, this does not imply that the examples shown are suitable TADF materials in the context of this invention. B .
[0849] The following shows the formula E B -I's TADF material E B Non-restrictive examples:
[0850]
[0851]
[0852]
[0853]
[0854]
[0855] The following shows the formula E B -II's TADF material E B Non-restrictive examples:
[0856]
[0857]
[0858]
[0859]
[0860] The following shows the formula E B -III's TADF material E B Non-restrictive examples:
[0861]
[0862]
[0863]
[0864] The following shows the formula E B -IV's TADF material E B Non-restrictive examples:
[0865] The following shows the formula E B -V TADF material E B Non-restrictive examples:
[0866]
[0867] The following shows the formula E B -VI's TADF material E B Non-restrictive examples:
[0868]
[0869] The following shows the formula E B -VII's TADF material E B Non-restrictive examples:
[0870]
[0871] The following shows the formula E B -VIII's TADF material E B Non-restrictive examples:
[0872] The following shows the formula E B -IX's TADF material E B Non-restrictive examples:
[0873]
[0874]
[0875] The following shows the formula E B -X TADF material E B Non-restrictive examples:
[0876]
[0877]
[0878] The following shows the formula E B -XI's TADF material E B Non-restrictive examples:
[0879]
[0880] TADF material E B The synthesis can be carried out via standard reactions and reaction conditions known to those skilled in the art. Typically, in the first step, the synthesis according to formula E can be performed as exemplarily shown below. B -III, Formula E B -IV and E B -V any of the TADF materials E B The coupling reaction (preferably, a palladium-catalyzed coupling reaction):
[0881]
[0882] E1 can be any boric acid (R B =H) or equivalent borate ester (R) B =alkyl or aryl), specifically, two R B A ring can be formed to obtain, for example, pinacol borate. E2 is used as the second reactant, where Hal refers to a halogen and can be I, Br, or Cl, but is preferably Br. The reaction conditions for this palladium-catalyzed coupling reaction are known to those skilled in the art (e.g., by WO2017 / 005699), and it is known that the reactive groups of E1 and E2 can be interchanged as follows to optimize the reaction yield:
[0883]
[0884] In the second step, the TADF material is obtained via a reaction of a nitrogen heterocycle with an aryl halide (preferably an aryl fluoride E3) in a nucleophilic aromatic substitution process. Typical conditions include the use of, for example, a base (such as tripotassium phosphate or sodium hydride) in an aprotic polar solvent (such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF)).
[0885]
[0886] Specifically, the donor molecule E4 is a 3,6-substituted carbazole (e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g., 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1,8-di-tert-butylcarbazole), a 1-substituted carbazole (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a 2-substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole, 2-tert-butylcarbazole), or a 3-substituted carbazole (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).
[0887] Alternatively, halogen-substituted carbazole (specifically, 3-bromocarbazole) can be used as E4.
[0888] In subsequent reactions, borate or boric acid functional groups can be introduced, exemplarily, at the positions of one or more halogen substituents introduced via E4 (e.g., via reaction with bis(pinacol)diboron (CAS No. 73183-34-3)) to generate the corresponding carbazole-3-yl-borate or carbazole-3-yl-boronic acid. Subsequently, the corresponding halogenated reactants (e.g., R) can be introduced. a -Hal, preferably R a -Cl and R a The coupling reaction of -Br) introduces one or more substituents R. a R b Or R d Replaces borate ester groups or boric acid groups.
[0889] Optionally, the halogen substituent introduced via DH can be located at the position of one or more halogen substituents via a reaction with substituent R. a [R a -B(OH)2]、R b [R b -B(OH)2] or R d [R d The boric acid or its corresponding borate ester of [-B(OH)2] is reacted to introduce one or more substituents R. a R b Or R d .
[0890] Other TADF materials can be obtained similarly. B TADF material E B It can also be obtained through any alternative synthetic route suitable for this purpose.
[0891] Alternative synthetic routes may include introducing nitrogen heterocycles into aryl halides or aryl pseudohalides via copper or palladium-catalyzed coupling, preferably aryl bromides, aryl iodides, aryl trifluoromethanesulfonates, or aryl toluenesulfonates.
[0892] (Multiple) Phosphorescent materials P B
[0893] In the context of this invention, phosphorescent material P B Light emission from the triplet state is obtained by utilizing the intramolecular spin-orbit interaction (heavy atom effect) caused by metal atoms.
[0894] Generally, it is understood that all phosphorescent complexes used in organic electroluminescent devices in the prior art can also be used in the organic electroluminescent devices according to the present invention.
[0895] As is known to those skilled in the art, phosphorescent materials P used in organic electroluminescent devices B Typically, these are complexes of Ir, Pt, Pd, Au, Os, Eu, Ru, Re, Ag, and Cu. In the context of this invention, complexes of Ir, Pt, and Pd are preferred, and more preferably, complexes of Ir and Pt. Those skilled in the art know which materials are suitable as phosphorescent materials in organic electroluminescent devices and how to synthesize them. Furthermore, those skilled in the art are familiar with the design principles of phosphorescent complexes for organic electroluminescent devices and know how to modulate the emission of the complexes by means of structural changes.
[0896] See for example: C.-L. Ho, H. Li, W.-Y. Wong, Journal of Organometallic Chemistry 2014, 751, 261, DOI: 10.1016 / j.jorganchem.2013.09.035; T. Fleetham, G. Li, J. Li, Advanced Science News 2017, 29, 1601861, DOI: 10.1002 / adma.201601861; A. R. B. M. Yusoff, A. J. Huckaba, M. K. Nazeeruddin, Topics in Current Chemistry (Z) 2017, 375:39, 1, DOI: 10.1007 / s41061-017-0126-7; T.-Y. Li, J. Wu, Z.-G. Wu, Y.-X. Zheng, J.-L. Zuo, Y. Pan, Coordination Chemistry Reviews 2018, 374, 55, DOI: 10.1016 / j.ccr.2018.06.014.
[0897] For example, US2020274081(A1), US20010019782(A1), US20020034656(A1), US20030138657(A1), US2005123791(A1), US20060065890(A1), US20060134462( A1), US20070034863(A1), US20070111026(A1), US2007034863(A1), US200 7138437(A1), US20080020237(A1), US20080297033(A1), US2008210930(A 1), US20090115322(A1), US2009104472(A1), US20100244004(A1), US201 0105902(A1), US20110057559(A1), US2011215710(A1), US2012292601(A1 ), US2013165653(A1), US20140246656(A1), US20030068526(A1), US20050 123788(A1), US2005260449(A1), US20060127696(A1), US20060202194(A1 ), US20070087321(A1), US20070190359(A1), US2007104979(A1), US2007224450(A1), US20080233410(A1), US200805851(A1), US20090039776(A1) , US20090179555(A1), US20100090591(A1), US20100295032(A1), US20030 072964(A1), US20050244673(A1), US20060008670(A1), US20060134459(A 1), US20060251923(A1), US20070103060(A1), US20070231600(A1), US200 7104980(A1), US2007278936(A1), US20080261076(A1), US2008161567(A1 ), US20090108737(A1), US2009085476(A1), US20100148663(A1), US20101 02716(A1), US2010270916(A1), US20110204333(A1), US2011285275(A1),US2013033172(A1), US2013334521(A1), US2014103305(A1), US2003068536(A1), US2003085646(A1), US2006228581(A1), US2006197077(A1), US2011114922(A1), US2003054198(A1), and EP2730583(A1) disclose P, which can be used as a phosphorescent material in the context of this invention. B Phosphorescent materials. It is understood that this does not imply that the invention is limited to organic electroluminescent devices incorporating phosphorescent materials described in one of the cited references.
[0898] Examples of phosphorescent complexes for use in organic electroluminescent devices such as those described in US2020274081(A1) include the complexes shown below. Furthermore, it is understood that the invention is not limited to these examples.
[0899]
[0900]
[0901]
[0902]
[0903]
[0904]
[0905]
[0906]
[0907]
[0908]
[0909] As will be appreciated by those skilled in the art as described above, any phosphorescent complex used in the prior art can be suitable as the phosphorescent material P in the context of this invention. B .
[0910] In one embodiment of the invention, each phosphorescent material P B Including iridium (Ir).
[0911] In one embodiment of the invention, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B) are organometallic complexes that include iridium (Ir) or platinum (Pt).
[0912] In one embodiment of the invention, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B ) is an organometallic complex that includes iridium (Ir).
[0913] In one embodiment of the invention, at least one phosphorescent material P B (Preferably, each phosphorescent material P) B ) is an organometallic complex that includes platinum (Pt).
[0914] Phosphorescent materials P B Non-restrictive examples also include those by the following formula P B -I indicates compounds,
[0915]
[0916] In formula P B In -I, M is selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu;
[0917] n is an integer from 1 to 3; and
[0918] X 2 and Y 1 Each time they appear, they independently form bidentate monoanion ligands together.
[0919] In one embodiment of the invention, each phosphorescent material P B Including according to formula P B -I's structure or is derived from formula P B The structural composition of -I
[0920]
[0921] M is selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu;
[0922] n is an integer from 1 to 3; and
[0923] X 2 and Y 1 Each time they appear, they independently form bidentate monoanion ligands together.
[0924] From formula P B Examples of compounds represented by -I include those derived from the following formula P B -II or P B Compounds represented by -III:
[0925]
[0926] In formula P B -II and P B In -III, X' is an aromatic ring in which carbon (C) is bonded to M, and Y′ is a ring in which nitrogen (N) is coordinated to M to form a ring.
[0927] X' and Y' combine, and X' and Y' can form a new loop. In equation P... B In -III, Z 3 It is a bidentate ligand with two oxygen (O) atoms. In formula P... B -II and P B In -III, from the viewpoint of high efficiency and long lifespan, M is preferred over Ir.
[0928] In formula P B -II and P B In -III, the aromatic ring X' is, for example, C6-C. 30 Aryl, preferably C6-C 16 Aryl, or even more preferably C6-C 12 Aryl, particularly preferably C6-C 10 Aryl, wherein X' optionally substitutes one or more substituents R each time it appears. E .
[0929] In formula P B -II and P B In -III, Y' is, for example, C2-C 30 heteroaryl, preferably C2-C 25 Heteroaryl, more preferably C2-C 20 heteroaryl, or even more preferably C2-C 15 heteroaryl, particularly preferably C2-C 10 Heteroaryl, wherein Y' optionally substitutes one or more substituents R each time it appears. E Furthermore, Y' can optionally replace one or more substituents R. E C1-C5 heteroaryl groups.
[0930] In formula P B -II and P B In -III, the bidentate ligand Z has two oxygen (O) atoms. 3 For example, a C2-C with two oxygen atoms. 30 Didentate ligand, C2-C with two oxygen atoms 25 Didentate ligands, more preferably C2-C having two oxygen atoms. 20 Didentate ligands, or even more preferably C2-C with two oxygen atoms. 15Didentate ligands, particularly preferably C2-C having two oxygen atoms. 10 Didentate ligands, of which Z 3 Each time it appears, one or more substituents R may be replaced. E In addition, Z 3 It is possible, for example, to optionally replace one or more substituents R. E It has two oxygen atoms and is a C2-C5 bidentate ligand.
[0931] R E Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 5E )2; OR 5E ;SR 5E ;Si(R) 5E )3; CF3; CN; Halogen; C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 5E And wherein, one or more non-adjacent CH2 groups are optionally R 5E C = CR 5E C≡C, Si(R) 5E )2、Ge(R 5E )2、Sn(R 5E )2. C=O, C=S, C=Se, C=NR 5E 、P(=O)(R 5E SO, SO2, NR 5E O, S or CONR 5E Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 5E And wherein, one or more non-adjacent CH2 groups are optionally R 5E C = CR 5E C≡C, Si(R) 5E )2、Ge(R 5E )2、Sn(R 5E )2. C=O, C=S, C=Se, C=NR 5E P(=O)(R) 5E SO, SO2, NR 5E O, S or CONR 5E Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 5E ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 5E .
[0932] R 5EEach time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 6E )2; OR 6E ;SR 6E ;Si(R) 6E )3; CF3; CN; F; C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 6E And wherein, one or more non-adjacent CH2 groups are optionally R 6E C = CR 6E C≡C, Si(R) 6E )2、Ge(R 6E )2、Sn(R 6E )2. C=O, C=S, C=Se, C=NR 6E P(=O)(R) 6E SO, SO2, NR 6E O, S or CONR 6E Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 6E ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 6E .
[0933] R 6E Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C6-C 18 Aryl group, optionally substituted with one or more C1-C5 alkyl substituents; C3-C 17 Heteroaryl groups, optionally substituted with one or more C1-C5 alkyl substituents; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 Aryl).
[0934] Substituent R E R 5E Or R 6E They can optionally be independently of each other with one or more substituents R. E R 5E R6E and / or with X', Y' and Z 3 Forming monocyclic or polycyclic aliphatic, aromatic, heteroaromatic and / or benzo[a] fused ring systems.
[0935] From formula P B Examples of compounds represented by -II include Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), faceted tris(2-(3-p-xylyl)phenyl)pyridinium(III), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fiq) )2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(2-phq)3, Ir(BT)2(acac), Ir(DMP)3, Ir(Mpq)3, Ir(phq)2tpy, surface type- Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, etc.
[0936] From formula P B Other examples of compounds represented by -II include those derived from the following formula P B -II-1 to Formula P B -II-11 represents the compound. In the structural formula, "Me" represents the methyl group.
[0937]
[0938] From formula P B Other examples of compounds represented by -III include those derived from the following formula P B -III-1 to Formula P B -III-6 represents the compound. In the structural formula, "Me" represents the methyl group.
[0939]
[0940] In addition, iridium complexes described in US2003017361(A1), US2004262576(A1), WO2010027583(A1), US2019245153(A1), US2013119354(A1), and US2019233451(A1) can be used. From the viewpoint of high efficiency of phosphorescent materials, Ir(ppy)3 and Hex-Ir(ppy)3 are commonly used for green light emission.
[0941] (Multiple) Small FWHM Emitters S B
[0942] In the context of this invention, a small half-peak full width (FWHM) emitter S B It is any emitter having an emission spectrum exhibiting an FWHM of less than or equal to 0.25 eV (≤0.25 eV), typically measured by spin-coating a film of the emitter in poly(methyl methacrylate) PMMA at room temperature (i.e., approximately 20 °C) using 1 wt% to 5 wt% (specifically, 2 wt%) of the emitter. Alternatively, a small FWHM emitter S B The emission spectrum can be measured in solution at room temperature (i.e., approximately 20°C), typically in dichloromethane or toluene using an emitter S at concentrations ranging from 0.001 mg / mL to 0.2 mg / mL. B .
[0943] In a preferred embodiment of the invention, the small FWHM emitter S B It is any emitter having an emission spectrum that exhibits the characteristics of an emitter S when used in PMMA at room temperature with 1 wt% to 5 wt% (specifically, 2 wt%) of the emitter S. B The spin-coated film measured an FWHM of ≤0.24 eV (more preferably ≤0.23 eV, even more preferably ≤0.22 eV, ≤0.21 eV, or ≤0.20 eV). Optionally, a small FWHM emitter S B The emission spectrum can be measured in solution at room temperature (i.e., approximately 20°C), typically in dichloromethane or toluene using an emitter S at concentrations ranging from 0.001 mg / mL to 0.2 mg / mL. B In other embodiments of the invention, each small FWHM emitter S B FWHM exhibiting values of ≤0.19eV, ≤0.18eV, ≤0.17eV, ≤0.16eV, ≤0.15eV, ≤0.14eV, ≤0.13eV, ≤0.12eV, or ≤0.11eV.
[0944] In one embodiment of the invention, each small FWHM emitter S BEmission at room temperature in PMMA (using 1% to 5% by weight (specifically, 2% by weight) of emitter S B The light with the maximum emission value in the wavelength range of 400 nm to 470 nm was measured.
[0945] In one embodiment of the invention, each small FWHM emitter S B Emission at room temperature in PMMA (using 1% to 5% by weight (specifically, 2% by weight) of emitter S B The light with the maximum emission value in the wavelength range of 500nm to 560nm was measured.
[0946] In one embodiment of the invention, each small FWHM emitter S B Emission at room temperature in PMMA (using 1% to 5% by weight (specifically, 2% by weight) of emitter S B The light with the maximum emission value in the wavelength range of 610 nm to 665 nm was measured.
[0947] In one embodiment of the invention, each small FWHM emitter S B Emission was carried out at room temperature (i.e., approximately 20°C) in dichloromethane or toluene using an emitter S at a concentration of 0.001 mg / mL to 0.2 mg / mL. B The measured light has the maximum emission value in the wavelength range of 400 nm to 470 nm.
[0948] In one embodiment of the invention, each small FWHM emitter S B Emission was carried out at room temperature (i.e., approximately 20°C) in dichloromethane or toluene using an emitter S at a concentration of 0.001 mg / mL to 0.2 mg / mL. B The measured light has the maximum emission value in the wavelength range of 500 nm to 560 nm.
[0949] In one embodiment of the invention, each small FWHM emitter S B Emission was carried out at room temperature (i.e., approximately 20°C) in dichloromethane or toluene using an emitter S at a concentration of 0.001 mg / mL to 0.2 mg / mL. B The measured light has the maximum emission value in the wavelength range of 610 nm to 665 nm.
[0950] It is understood that the TADF material E included in the light-emitting layer B of the organic electroluminescent device according to the invention BAlternatively, it may be an emitter having an emission spectrum exhibiting an FWHM of less than or equal to 0.25 eV (≤0.25 eV). Optionally, TADF material E may be included in the light-emitting layer B of the organic electroluminescent device according to the invention. B It can also exhibit maximum emission within the above wavelength range (i.e., 400nm to 470nm, 500nm to 560nm, 610nm to 665nm).
[0951] In one embodiment of the invention, one of the relationships represented by the following equations (23) to (25) applies:
[0952] 440nm<λ max (S B )<470nm (23)
[0953] 510nm<λ max (S B <550nm (24)
[0954] 610nm<λ max (S B <665nm (25),
[0955] Where, λ max (S B () refers to the small FWHM emitter S in the context of this invention. B The maximum value of the launch.
[0956] In one embodiment, the relationships expressed by equations (23) to (25) apply to materials included in any one of at least one light-emitting layer B of the organic electroluminescent device according to the invention. In one embodiment, the relationships expressed by equations (23) to (25) apply to materials included in the same light-emitting layer B of the organic electroluminescent device according to the invention.
[0957] In a preferred embodiment of the invention, each small FWHM emitter S B It is an organic emitter, which, in the context of the invention, means that it does not contain any transition metals. Preferably, each small FWHM emitter S according to the invention B It is mainly composed of the elements hydrogen (H), carbon (C), nitrogen (N) and boron (B), but may also include, for example, oxygen (O), silicon (Si), fluorine (F) and bromine (Br).
[0958] In a preferred embodiment of the invention, each small FWHM emitter S B It is a fluorescent emitter, which in the context of this invention means that when electronically excited (e.g., in an optoelectronic device according to the invention), the emitter is capable of emitting light at room temperature, wherein the emitted excited state is a singlet state.
[0959] In one embodiment of the invention, the small FWHM emitter S B Exhibiting at room temperature in PMMA (using 1 wt% to 5 wt% (specifically, 2 wt%) of emitter S B The measured photoluminescent quantum yield (PLQY) is equal to or greater than 50%.
[0960] In a preferred embodiment of the invention, the small FWHM emitter S B Exhibiting at room temperature in PMMA (using 1 wt% to 5 wt% (specifically, 2 wt%) of emitter S B The measured photoluminescent quantum yield (PLQY) is equal to or greater than 60%.
[0961] In even more preferred embodiments of the invention, the small FWHM emitter S B Exhibiting at room temperature in PMMA (using 1 wt% to 5 wt% (specifically, 2 wt%) of emitter S B The measured photoluminescent quantum yield (PLQY) is equal to or greater than 70%.
[0962] In even more preferred embodiments of the invention, the small FWHM emitter S B Exhibiting at room temperature in PMMA (using 1 wt% to 5 wt% (specifically, 2 wt%) of emitter S B The measured photoluminescent quantum yield (PLQY) is equal to or higher than 80%.
[0963] In a particularly preferred embodiment of the invention, the small FWHM emitter S B Exhibiting at room temperature in PMMA (using 1 wt% to 5 wt% (specifically, 2 wt%) of emitter S B The measured photoluminescent quantum yield (PLQY) is equal to or greater than 90%.
[0964] In one embodiment of the invention, the small FWHM emitter S B It showed that at room temperature (i.e., approximately 20°C) in dichloromethane or toluene, using emitter S at concentrations ranging from 0.001 mg / mL to 0.2 mg / mL... B The measured photoluminescence quantum yield (PLQY) is equal to or greater than 50%.
[0965] In a preferred embodiment of the invention, the small FWHM emitter S B It showed that at room temperature (i.e., approximately 20°C) in dichloromethane or toluene, using emitter S at concentrations ranging from 0.001 mg / mL to 0.2 mg / mL... BThe measured photoluminescence quantum yield (PLQY) is equal to or greater than 60%.
[0966] In even more preferred embodiments of the invention, the small FWHM emitter S B It showed that at room temperature (i.e., approximately 20°C) in dichloromethane or toluene, using emitter S at concentrations ranging from 0.001 mg / mL to 0.2 mg / mL... B The measured photoluminescence quantum yield (PLQY) is equal to or greater than 70%.
[0967] In even more preferred embodiments of the invention, the small FWHM emitter S B It showed that at room temperature (i.e., approximately 20°C) in dichloromethane or toluene, using emitter S at concentrations ranging from 0.001 mg / mL to 0.2 mg / mL... B The measured photoluminescence quantum yield (PLQY) is equal to or greater than 80%.
[0968] In a particularly preferred embodiment of the invention, the small FWHM emitter S B It showed that at room temperature (i.e., approximately 20°C) in dichloromethane or toluene, using emitter S at concentrations ranging from 0.001 mg / mL to 0.2 mg / mL... B The measured photoluminescence quantum yield (PLQY) is equal to or greater than 90%.
[0969] Those skilled in the art know how to design small FWHM emitters that meet the above requirements or preferred features. B .
[0970] In the context of this invention, it is suitable to provide a small FWHM emitter S B One class of molecules is the well-known 4,4-difluoro-4-boron-3a,4a-diaza-s-indarin (BODIPY) type material. The structural characteristics of this material and its applications in organic electroluminescent devices have been extensively reviewed and are common knowledge to those skilled in the art. The prior art also reveals how to synthesize this material and how to obtain emitters with specific emission colors.
[0971] See for example: J.Liao, Y.Wang, Y.Xu, H.Zhao, X.Xiao, 2020,32(1),56–70,DOI:10.1080 / 10610278.2019.1691727; M.Poddar,R.Misra,Coordination Chemistry Reviews 2020,421,213462–213483; DOI:10.1016 / j.ccr.2020.213462.
[0972] Those skilled in the art will also be familiar with the fact that the BODIPY base structure is shown below:
[0973]
[0974] For example, it is not ideally suited as an emitter in organic electroluminescent devices due to intermolecular π-π interactions and associated self-quenching.
[0975] It is common knowledge to those skilled in the art that by attaching bulky groups as substituents to the BODIPY core structure shown above, more suitable emitter molecules for organic electroluminescent devices can be obtained. These bulky groups can be, for example, aryl, heteroaryl, alkyl, or alkoxy substituents, or condensed polycyclic aromatic compounds or heteroaromatic compounds, all of which can optionally be substituted. The choice of suitable substituents at the BODIPY core is obvious to those skilled in the art and can be readily derived from the prior art. This also applies to the numerous synthetic routes already established for the synthesis and subsequent modification of these molecules.
[0976] See, for example: BM Squeo, M. Pasini, Supramolecular Chemistry 2020, 32(1), 56–70, DOI:10.1080 / 10610278.2019.1691727; M. Poddar, R. Misra, Coordination Chemistry Reviews 2020, 421, 213462–213483; DOI:10.1016 / j.ccr.2020.213462.
[0977] The following shows a small FWHM emitter S that can be used in the context of this invention.B Example of a BODIPY class emitter:
[0978]
[0979]
[0980]
[0981] It is understood that this does not imply that BODIPY derivatives having structural features other than those shown above are unsuitable as small FWHM emitters in the context of this invention. B .
[0982] For example, the BODIPY derivative structures or their derivatives disclosed in US2020251663(A1), EP3671884(A1), US20160230960(A1) and US20150303378(A1) can be suitable small FWHM emitters for use according to the present invention. B .
[0983] Furthermore, those skilled in the art will know that emitters for organic electroluminescent devices can also be obtained by replacing one or two fluorine substituents attached to the central boron atom of the BODIPY core structure with alkoxy or aryloxy groups attached via oxygen atoms, which can optionally be substituted, preferably with electron-withdrawing substituents (such as fluorine (F) or trifluoromethyl (CF3)). Such molecules are disclosed, for example, in US2012037890 (A1), and those skilled in the art will understand that these BODIPY-related compounds can also be suitable small FWHM emitters in the context of this invention. B An example of such an emitter molecule is shown below, which does not imply that the structure shown may be a suitable small FWHM emitter S in the context of this invention. B :
[0984]
[0985] Furthermore, the boron-containing emitter configuration related to BODIPY disclosed in US20190288221(A1) can provide a suitable small FWHM emitter S for use according to the present invention. B A group of emitters.
[0986] Small FWHM emitter S suitable for providing the context of the invention B Another type of molecule is the near-range charge transfer (NRCT) emitter.
[0987] Typical NRCT emitters are described in the literature to exhibit a delayed component in time-resolved photoluminescence spectra and to demonstrate near-range HOMO-LUMO separation. See, for example: T. Hatakeyama, K. Shiren, K. Nakajima, S. Nomura, S. Nakatsuka, K. Kinoshita, J. Ni, Y. Ono, and T. Ikuta, Advanced Materials 2016, 28(14), 2777, DOI:10.1002 / adma.201505491.
[0988] A typical NRCT emitter shows only one emission band in its emission spectrum, whereas a typical fluorescent emitter shows several different emission bands due to vibrational processes.
[0989] Those skilled in the art know how to design and synthesize small FWHM emitters suitable for use in the context of this invention. B NRCT emitters. For example, the emitter disclosed in EP3109253(A1) can be used as a small FWHM emitter in the context of this invention. B .
[0990] In addition, for example, US2014058099(A1), US2009295275(A1), US2012319052(A1), EP2182040(A2), US2018069182(A1), US2019393419(A1), US2020006671(A1), US2020098991(A1), US2020176 Patents 684(A1), US2020161552(A1), US2020227639(A1), US2020185635(A1), EP3686206(A1), WO2020217229(A1), WO2020208051(A1), and US2020328351(A1) disclose methods suitable for use as small FWHM emitters according to the present invention. B The material of the launcher.
[0991] Small FWHM emitter S can be used in the context of this invention. B A group of emitters comprises a boron (B) emitter consisting of a structure according to formula DABNA-I or a structure according to formula DABNA-I:
[0992]
[0993] in,
[0994] Each of rings A', B', and C' independently represents an aromatic or heteroaromatic ring comprising 5 to 24 ring atoms, wherein, in the case of a heteroaromatic ring, 1 to 3 ring atoms are heteroatoms independently selected from N, O, S, and Se; wherein,
[0995] One or more hydrogen atoms in each of the aromatic or heteroaromatic rings A', B', and C' are optionally and independently substituented by a substituent R. DABNA-1 Substitution, the substituent R DABNA-1 Each occurrence is independently selected from the group consisting of: deuterium; N(R) DABNA-2 )2; OR DABNA-2 ;SR DABNA-2 ;Si(R) DABNA-2 )3;B(OR DABNA-2 )2; OSO2R DABNA-2 ; CF3; CN; Halogens (F, Cl, Br, I); C1-C 40 Alkyl groups, optionally substituted with one or more substituents R DABNA-2 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-2 C = CR DABNA-2 C≡C, Si(R) DABNA-2 )2、Ge(R DABNA-2 )2、Sn(R DABNA-2 )2. C=O, C=S, C=Se, C=NR DABNA-2 P(=O)(R) DABNA-2 SO, SO2, NR DABNA-2 O, S or CONR DABNA-2 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R DABNA-2 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-2 C = CR DABNA-2 C≡C, Si(R) DABNA-2 )2、Ge(R DABNA-2 )2、Sn(R DABNA-2 )2. C=O, C=S, C=Se, C=NR DABNA-2 、P(=O)(R DABNA-2 SO, SO2, NR DABNA-2 O, S or CONR DABNA-2 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R DABNA-2 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-2 C = CR DABNA-2C≡C, Si(R) DABNA-2 )2、Ge(R DABNA-2 )2、Sn(R DABNA-2 )2. C=O, C=S, C=Se, C=NR DABNA-2 、P(=O)(R DABNA-2 SO, SO2, NR DABNA-2 O, S or CONR DABNA-2 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R DABNA-2 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-2 C = CR DABNA-2 C≡C, Si(R) DABNA-2 )2、Ge(R DABNA-2 )2、Sn(R DABNA-2 )2. C=O, C=S, C=Se, C=NR DABNA-2 、P(=O)(R DABNA-2 SO, SO2, NR DABNA-2 O, S or CONR DABNA-2 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. DABNA-2 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-2 C = CR DABNA-2 Si(R) DABNA-2 )2、Ge(R DABNA-2 )2、Sn(R DABNA-2 )2. C=O, C=S, C=Se, C=NR DABNA-2 、P(=O)(R DABNA-2 SO, SO2, NR DABNA-2 O, S or CONR DABNA-2 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R DABNA-2 C3-C 57 Heteroaryl, optionally substituted with one or more substituents R DABNA-2 ; and aliphatic cyclic amines, comprising 4 to 18 carbon atoms and 1 to 3 nitrogen atoms;
[0996] R DABNA-2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-6 )2; OR DABNA-6 ;SR DABNA-6 ;Si(R) DABNA-6 )3;B(OR DABNA-6 )2; OSO2RDABNA-6 ; CF3; CN; Halogen (F, Cl, Br, I); C1-C5 alkyl, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C1-C5 alkoxy group, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C1-C5 thioalkoxy, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C2-C5 alkenyl, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C2-C5 ynyl group, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Replacement; C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-6 C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-6 ; and aliphatic cyclic amines, comprising 4 to 18 carbon atoms and 1 to 3 nitrogen atoms;
[0997] Among them, selected from R DABNA-1 and R DABNA-2 Two or more adjacent substituents may optionally form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic system fused to an adjacent ring A', ring B' or ring C', wherein the fused ring system formed optionally in this way (i.e., the corresponding ring A', ring B' or ring C' and the additional rings optionally fused to it comprise a total of 8 to 30 ring atoms)
[0998] Y a and Y b Independently selected from direct (single) key, NR DABNA-3 O, S, C(R) DABNA-3 2. Si(R) DABNA-3 )2、BR DABNA-3 and Se;
[0999] R DABNA-3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-4 )2; OR DABNA-4 ;SR DABNA-4 ;Si(R) DABNA-4 )3;B(OR DABNA-4 )2; OSO2R DABNA-4 ; CF3; CN; Halogens (F, Cl, Br, I); C1-C40 Alkyl groups, optionally substituted with one or more substituents R DABNA-4 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-4 C = CR DABNA-4 C≡C, Si(R) DABNA-4 )2、Ge(R DABNA-4 )2、Sn(R DABNA-4 )2. C=O, C=S, C=Se, C=NR DABNA-4 P(=O)(R) DABNA-4 SO, SO2, NR DABNA-4 O, S or CONR DABNA-4 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R DABNA-4 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-4 C = CR DABNA-4 C≡C, Si(R) DABNA-4 )2、Ge(R DABNA-4 )2、Sn(R DABNA-4 )2. C=O, C=S, C=Se, C=NR DABNA-4 P(=O)(R) DABNA-4 SO, SO2, NR DABNA-4 O, S or CONR DABNA-4 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R DABNA-4 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-4 C = CR DABNA-4 C≡C, Si(R) DABNA-4 )2、Ge(R DABNA-4 )2、Sn(R DABNA-4 )2. C=O, C=S, C=Se, C=NR DABNA-4 P(=O)(R) DABNA-4 SO, SO2, NR DABNA-4 O, S or CONR DABNA-4 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R DABNA-4 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-4 C = CR DABNA-4 C≡C, Si(R) DABNA-4 )2、Ge(R DABNA-4 )2、Sn(R DABNA-4 )2. C=O, C=S, C=Se, C=NRDABNA-4 P(=O)(R) DABNA-4 SO, SO2, NR DABNA-4 O, S or CONR DABNA-4 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. DABNA-4 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-4 C = CR DABNA-4 Si(R) DABNA-4 )2、Ge(R DABNA-4 )2、Sn(R DABNA-4 )2. C=O, C=S, C=Se, C=NR DABNA-4 P(=O)(R) DABNA-4 SO, SO2, NR DABNA-4 O, S or CONR DABNA-4 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R DABNA-4 C3-C 57 Heteroaryl, optionally substituted with one or more substituents R DABNA-4 ; and aliphatic cyclic amines, comprising 4 to 18 carbon atoms and 1 to 3 nitrogen atoms;
[1000] R DABNA-4 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-5 )2; OR DABNA-5 ;SR DABNA-5 ;Si(R) DABNA-5 )3;B(OR DABNA-5 )2; OSO2R DABNA-5 ; CF3; CN; Halogens (F, Cl, Br, I); C1-C 40 Alkyl groups, optionally substituted with one or more substituents R DABNA-5 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-5 C = CR DABNA-5 C≡C, Si(R) DABNA-5 )2、Ge(R DABNA-5 )2、Sn(R DABNA-5 )2. C=O, C=S, C=Se, C=NR DABNA-5 P(=O)(R) DABNA-5 SO, SO2, NR DABNA-5 O, S or CONR DABNA-5 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R DABNA-5And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-5 C = CR DABNA-5 C≡C, Si(R) DABNA-5 )2、Ge(R DABNA-5 )2、Sn(R DABNA-5 )2. C=O, C=S, C=Se, C=NR DABNA-5 P(=O)(R) DABNA-5 SO, SO2, NR DABNA-5 O, S or CONR DABNA-5 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R DABNA-5 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-5 C = CR DABNA-5 C≡C, Si(R) DABNA-5 )2、Ge(R DABNA-5 )2、Sn(R DABNA-5 )2. C=O, C=S, C=Se, C=NR DABNA-5 P(=O)(R) DABNA-5 SO, SO2, NR DABNA-5 O, S or CONR DABNA-5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R DABNA-5 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-5 C = CR DABNA-5 C≡C, Si(R) DABNA-5 )2、Ge(R DABNA-5 )2、Sn(R DABNA-5 )2. C=O, C=S, C=Se, C=NR DABNA-5 P(=O)(R) DABNA-5 SO, SO2, NR DABNA-5 O, S or CONR DABNA-5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. DABNA-5 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-5 C = CR DABNA-5 Si(R) DABNA-5 )2、Ge(R DABNA-5 )2、Sn(R DABNA-5 )2. C=O, C=S, C=Se, C=NR DABNA-5 P(=O)(R) DABNA-5 SO, SO2, NRDABNA-5 O, S or CONR DABNA-5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R DABNA-5 C3-C 57 Heteroaryl, optionally substituted with one or more substituents R DABNA-5 ; and aliphatic cyclic amines, comprising 4 to 18 carbon atoms and 1 to 3 nitrogen atoms;
[1001] R DABNA-5 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-6 )2; OR DABNA-6 ;SR DABNA-6 ;Si(R) DABNA-6 )3;B(OR DABNA-6 )2; OSO2R DABNA-6 ; CF3; CN; Halogen (F, Cl, Br, I); C1-C5 alkyl, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C1-C5 alkoxy group, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C1-C5 thioalkoxy, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6)2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C2-C5 alkenyl, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 C≡C, Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Substitution; C2-C5 ynyl group, optionally substituted with one or more substituents R DABNA-6 And wherein, one or more non-adjacent CH2 groups are optionally R DABNA-6 C = CR DABNA-6 Si(R) DABNA-6 )2、Ge(R DABNA-6 )2、Sn(R DABNA-6 )2. C=O, C=S, C=Se, C=NR DABNA-6 P(=O)(R) DABNA-6 SO, SO2, NR DABNA-6 O, S or CONR DABNA-6 Replacement; C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-6 C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-6 ; and aliphatic cyclic amines, comprising 4 to 18 carbon atoms and 1 to 3 nitrogen atoms;
[1002] Among them, selected from R DABNA-3 R DABNA-4 and R DABNA-5 Two or more adjacent substituents may optionally form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic ring system with each other, wherein the ring system thus formed may optionally comprise a total of 8 to 30 ring atoms.
[1003] R DABNA-6Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh (Ph = phenyl); SPh; CF3; CN; F; Si(C1-C5 alkyl)3; Si(Ph)3; C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF3 or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3 or F; C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently surrounded by deuterium, CN, CF3, F, C1-C5 alkyl, SiMe3, SiPh3 or C6-C 18 Aryl substituents; C3-C 17 Heteroaryl, wherein optionally one or more hydrogen atoms are independently surrounded by deuterium, CN, CF3, F, C1-C5 alkyl, SiMe3, SiPh3 or C6-C 18 Aryl substituents; N(C6-C) 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);
[1004] Among them, in Y a and Y b One of them or Y a and Y b Both are NR DABNA-3 C(R) DABNA-3 )2、Si(R DABNA-3 )2 or BR DABNA-3 In the case of one or two substituents R DABNA-3 It can be optionally and independently of each other via a direct (single) key or via, in each case independently selected from NR DABNA-1 O, S, C(R) DABNA-1 )2、Si(R DABNA-1 )2、BR DABNA-1 The connecting atom or group of Se is bonded to the adjacent rings A' and B' (for Y). a =NR DABNA-3 C(R) DABNA-3 )2、Si(R DABNA-3 )2 or BR DABNA-3 ) or rings A' and C' (for Y)b =NR DABNA-3 C(R) DABNA-3 )2、Si(R DABNA-3 )2 or BR DABNA-3 One or two of them;
[1005] Optionally, two or more DABNA-I structures (preferably two DABNA-I structures) are conjugate to each other, and preferably, they are fused together by sharing at least one bond (more preferably, exactly one bond).
[1006] Optionally, two or more structures of formula DABNA-I (preferably two structures of formula DABNA-I) exist in the emitter and share at least one aromatic ring or heteroaromatic ring (preferably exactly one aromatic ring or heteroaromatic ring) (i.e., the ring can be part of two structures of formula DABNA-I), wherein the at least one aromatic ring or heteroaromatic ring is preferably any one of ring A', ring B' and ring C' of formula DABNA-I, but may also be selected from R DABNA-1 R DABNA-2 R DABNA-3 R DABNA-4 R DABNA-5 and R DABNA-6 Any aromatic or heteroaromatic substituent (specifically, R) DABNA-3 Or any aromatic or heteroaromatic ring formed by two or more adjacent substituents as described above, wherein the shared ring may constitute the same or different parts of two or more structures of formula DABNA-I of the shared ring (i.e., the shared ring may be, for example, ring C' of two structures of formula DABNA-I optionally included in the emitter, or the shared ring may be, for example, ring B' of one structure of formula DABNA-I and ring C' of another structure optionally included in the emitter); and
[1007] Optionally, R DABNA-1 R DABNA-2 R DABNA-3 R DABNA-4 R DABNA-5 and R DABNA-6 At least one of them is replaced by a bond attached to another chemical entity of the formula DABNA-I, and / or wherein, optionally, R DABNA-1 R DABNA-2 R DABNA-3 R DABNA-4 R DABNA-5 and R DABNA-6 At least one hydrogen atom in any of them is replaced by a bond attached to another chemical entity of the formula DABNA-I.
[1008] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them includes a structure according to formula DABNA-I.
[1009] In one embodiment of the invention, in at least one light-emitting layer B (preferably, each light-emitting layer B), each small FWHM emitter S B Including the structure according to formula DABNA-I.
[1010] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them consists of a structure according to formula DABNA-I.
[1011] In one embodiment of the invention, in at least one light-emitting layer B (preferably, each light-emitting layer B), each small FWHM emitter S B It consists of the structure according to formula DABNA-I.
[1012] In a preferred embodiment of the invention, wherein in at least one light-emitting layer B (preferably, each light-emitting layer B), one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of them includes or consists of a structure according to formula DABNA-I, wherein rings A', B' and C' are all aromatic rings having 6 ring atoms (i.e., they are all benzene rings).
[1013] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I, Y a and Y b Selected independently from NR DABNA-3 O, S, C(R) DABNA-3 )2 and Si(R DABNA-3 )2.
[1014] In a preferred embodiment of the invention, wherein in at least one light-emitting layer B (preferably, each light-emitting layer B), one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) BEach of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I, Y a and Y b Selected independently from NR DABNA-3 O and S.
[1015] In even more preferred embodiments of the invention, wherein, in at least one light-emitting layer B (preferably, each light-emitting layer B), one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I, Y a and Y b Selected independently from NR DABNA-3 And O.
[1016] In a particularly preferred embodiment of the invention, wherein in at least one light-emitting layer B (preferably, each light-emitting layer B), one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I, Y a and Y b Both are NR DABNA-3 .
[1017] In a particularly preferred embodiment of the invention, wherein in at least one light-emitting layer B (preferably, each light-emitting layer B), one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I, Y a and Y b They are the same and both are NR. DABNA-3 .
[1018] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1019] R DABNA-1 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R)DABNA-2 )2; OR DABNA-2 ;SR DABNA-2 ;Si(R) DABNA-2 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R DABNA-2 C1-C5 alkoxy groups, optionally substituted with one or more substituents R DABNA-2 ;C1-C5 thioalkoxy groups, optionally substituted with one or more substituents R DABNA-2 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-2 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-2 ;
[1020] R DABNA-2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-6 )2; OR DABNA-6 ;SR DABNA-6 ;Si(R) DABNA-6 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R DABNA-6 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-6 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-6 ;
[1021] Among them, selected from R DABNA-1 and R DABNA-2 Two or more adjacent substituents may optionally form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic system fused to an adjacent ring A', ring B' or ring C', wherein the fused ring system formed in this way (i.e., the corresponding ring A', ring B' or ring C' and the additional rings optionally fused to it) comprises a total of 8 to 30 ring atoms.
[1022] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1023] R DABNA-1Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-2 )2; OR DABNA-2 ;SR DABNA-2 ;Si(R) DABNA-2 )3; C1-C5 alkyl, optionally substituted with one or more substituents R DABNA-2 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-2 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-2 ;
[1024] R DABNA-2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-6 )2; OR DABNA-6 ;SR DABNA-6 ;Si(R) DABNA-6 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R DABNA-6 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-6 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-6 ;
[1025] Among them, selected from R DABNA-1 and R DABNA-2 Two or more adjacent substituents may optionally form a monocyclic or polycyclic aliphatic or aromatic or heterocyclic carbocyclic or heterocyclic system fused to an adjacent ring A', ring B' or ring C', wherein the fused ring system formed in this way (i.e., the corresponding ring A', ring B' or ring C' and the additional rings optionally fused to it) comprises a total of 8 to 30 ring atoms.
[1026] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1027] R DABNA-1 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-2 )2; OR DABNA-2 ;SR DABNA-2C1-C5 alkyl groups, optionally substituted with one or more substituents R. DABNA-2 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-2 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-2 ;
[1028] R DABNA-2 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; OPh; CN; Me; i Pr; t Bu; Si(Me)3; Ph, optionally substituted with one or more substituents R DABNA-6 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-6 ;
[1029] Among them, two or more adjacent R DABNA-1 A monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic system fused to an adjacent ring A', ring B', or ring C', wherein the fused ring system (i.e., the corresponding ring A', ring B', or ring C' and the (multiple) additional rings optionally fused to it) comprises a total of 8 to 30 ring atoms.
[1030] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1031] R DABNA-1 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; OPh; Me; i Pr; t Bu; Si(Me)3; Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr, t Bu, Ph, or CN are substituted; and C3-C 17 Heteroaryl groups, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr, t Replace with Bu, Ph, or CN;
[1032] Among them, two or more adjacent RDABNA-1 Optionally, a monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic system fused to an adjacent ring A', ring B', or ring C' may be formed, wherein the fused ring system (i.e., the corresponding ring A', ring B', or ring C' and the additional rings optionally fused to it) may comprise a total of 8 to 30 ring atoms.
[1033] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1034] R DABNA-1 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; Me; i Pr; t Bu;Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr, t Bu, Ph, or CN substitution; carbazoyl group, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr, t Bu, Ph, or CN are substituted; triazine group, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr, t Bu or Ph substitution; pyrimidinyl group, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr, t Bu or Ph substitution; and pyridyl, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr, t Bu or Ph can be substituted;
[1035] Among them, two or more adjacent R DABNA-1 Optionally, a monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic system fused to an adjacent ring A', ring B', or ring C' may be formed, wherein the fused ring system (i.e., the corresponding ring A', ring B', or ring C' and the additional rings optionally fused to it) may comprise a total of 8 to 30 ring atoms.
[1036] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). BAt least one of them (preferably one or more small FWHM emitters S) B Each of the following includes or consists of a structure according to formula DABNA-I, selected from R DABNA-1 and R DABNA-2 The adjacent substituents do not form a monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic system that fuses to the adjacent ring A', ring B', or ring C'.
[1037] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1038] R DABNA-3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; C1-C4 alkyl, optionally substituted with one or more substituents R. DABNA-4 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-4 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-4 ;
[1039] R DABNA-4 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) DABNA-5 )2; OR DABNA-5 ;SR DABNA-5 ; Si(C1-C5 alkyl)3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R DABNA-5 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-5 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-5 ;
[1040] R DABNA-5 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; OPh; Si(Me)₃; CF₃; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium; C6-C 18 aryl, wherein one or more hydrogen atoms are optionally independently of each other deuterium, Me,i Pr, t Bu, Ph, or CN are substituted; and C3-C 17 Heteroaryl groups, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr, t Replace with Bu, Ph, or CN;
[1041] Among them, selected from R DABNA-3 R DABNA-4 and R DABNA-5 Two or more adjacent substituents may optionally form a monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic system with a total of 8 to 30 ring atoms.
[1042] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1043] R DABNA-3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; C1-C4 alkyl, optionally substituted with one or more substituents R. DABNA-4 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-4 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-4 ;
[1044] R DABNA-4 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; OPh; Si(Me)₃; CF₃; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium; C6-C 18 aryl, wherein one or more hydrogen atoms are optionally independently of each other deuterium, Me, i Pr, t Bu, Ph, or CN are substituted; and C3-C 17 Heteroaryl groups, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr, t Replace with Bu, Ph, or CN;
[1045] Among them, selected from RDABNA-3 and R DABNA-4 Two or more adjacent substituents in a system do not form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic systems with each other.
[1046] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1047] R DABNA-3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; C1-C4 alkyl, optionally substituted with one or more substituents R. DABNA-4 C6-C 18 aryl, optionally substituted with one or more substituents R DABNA-4 ; and C3-C 17 Heteroaryl, optionally substituted with one or more substituents R DABNA-4 ;
[1048] R DABNA-4 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium; C6-C 18 aryl, wherein one or more hydrogen atoms are optionally independently of each other deuterium, Me, i Pr, t Bu, Ph, or CN are substituted; and C3-C 17 Heteroaryl groups, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr, t Replace with Bu, Ph, or CN;
[1049] Among them, selected from R DABNA-3 and R DABNA-4 Two or more adjacent substituents in a system do not form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic systems with each other.
[1050] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1051] R DABNA-3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and C6-C 18 aryl, wherein one or more hydrogen atoms are optionally independently of each other deuterium, Me, i Pr, t Replace with Bu, Ph, or CN;
[1052] Among them, selected from R DABNA-3 Two or more adjacent substituents in a system do not form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic systems with each other.
[1053] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1054] R DABNA-3 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally independently of each other by deuterium, Me, i Pr, t Replace with Bu, Ph, or CN;
[1055] Among them, selected from R DABNA-3 Two or more adjacent substituents in a system do not form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic carbocyclic or heterocyclic systems with each other.
[1056] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1057] R DABNA-6Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh (Ph = phenyl); SPh; CF3; CN; F; Si(C1-C5 alkyl)3; Si(Ph)3; C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF3 or F; C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently surrounded by deuterium, CN, CF3, F, C1-C5 alkyl, SiMe3, SiPh3 or C6-C 18 Aryl substituents; C3-C 17 Heteroaryl, wherein optionally one or more hydrogen atoms are independently surrounded by deuterium, CN, CF3, F, C1-C5 alkyl, SiMe3, SiPh3 or C6-C 18 Aryl substituents; N(C6-C) 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 Aryl).
[1058] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1059] R DABNA-6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; OPh (Ph = phenyl); SPh; CF₃; CN; F; Si(Me)₃; Si(Ph)₃; C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF₃ or F; C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently converted by deuterium, CN, CF3, F, Me, i Pr、 t Bu, SiMe3, SiPh3 or Ph substitution; and C3-C 17 Heteroaryl groups, wherein optionally one or more hydrogen atoms are independently converted by deuterium, CN, CF3, F, Me, i Pr、 t Bu, SiMe3, SiPh3, or Ph substitution.
[1060] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1061] R DABNA-6 Each occurrence is independently selected from the group consisting of: hydrogen; deuterium; N(Ph)₂; CN; F; Me; i Pr; t Bu;Ph, wherein, optionally, one or more hydrogen atoms are independently controlled by deuterium, CN, Me, i Pr、 t Bu or Ph substitution; and C3-C 17 Heteroaryl groups, wherein optionally one or more hydrogen atoms are independently converted by deuterium, CN, Me, i Pr、 t Bu or Ph can be substituted.
[1062] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I.
[1063] R DABNA-6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein, optionally, one or more hydrogen atoms are independently controlled by deuterium, Me, i Pr、 t Bu or Ph can be substituted.
[1064] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula DABNA-I or is composed of a structure according to formula DABNA-I, when Y a and / or Y b It is NR DABNA-3 C(R) DABNA-3 )2、Si(R DABNA-3)2 or BR DABNA-3 In the case of one or two substituents R DABNA-3 Not bound to adjacent rings A' and B' (for Y) a =NR DABNA-3 C(R) DABNA-3 )2、Si(R DABNA-3 )2 or BR DABNA-3 ) or rings A' and C' (for Y) b =NR DABNA-3 C(R) DABNA-3 )2、Si(R DABNA-3 )2 or BR DABNA-3 One or two of them.
[1065] In one embodiment, the small FWHM emitter S in the context of the present invention B Alternatively, it can be a polymer (e.g., a dimer) of the above-described formula DABNA-I, meaning that its structure comprises more than one subunit, each of which has a structure according to formula DABNA-I. In this case, those skilled in the art will understand that two or more subunits according to formula DABNA-I can, for example, be conjugated, preferably fused together (i.e., sharing at least one bond, wherein the corresponding substituents attached to the atoms forming said bond may no longer be present). The two or more subunits can also share at least one aromatic ring or heteroaromatic ring, preferably exactly one aromatic ring or heteroaromatic ring. This means, for example, small FWHM emitters S B It may include two or more subunits, each having the structure of formula DABNA-I, wherein the two subunits share an aromatic ring or heteroaromatic ring (i.e., the corresponding ring is part of both subunits). Therefore, because the shared ring exists only once, the corresponding polymeric (e.g., dimeric) emitter S B It may not contain two complete subunits according to formula DABNA-I. However, those skilled in the art will understand that, here, such an emitter is still considered a polymer of formula DABNA-I (e.g., a dimer if it includes two subunits having the structure of formula DABNA-I). This also applies to polymers sharing more than one ring. Preferably, the polymer is a dimer comprising two subunits, each having the structure of formula DABNA-I.
[1066] In one embodiment of the invention, at least one small FWHM emitter S is present in at least one light-emitting layer B (preferably, each light-emitting layer B). B (Preferably, each small FWHM emitter S) B) is a dimer of the formula DABNA-I as described above, which means that the emitter comprises two subunits, each having a structure according to the formula DABNA-I.
[1067] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes two or more structures (i.e., sub-units) according to DABNA-I (preferably exactly two structures (i.e., sub-units) according to DABNA-I, or is composed of two or more structures (i.e., sub-units) according to DABNA-I (preferably exactly two structures (i.e., sub-units) according to DABNA-I).
[1068] These subunits share at least one aromatic ring or heteroaromatic ring (preferably exactly one aromatic ring or heteroaromatic ring) (i.e., the ring may be part of two structures of formula DABNA-I), and the shared ring (multiple rings) may be any one of rings A', B', and C' of formula DABNA-I, but may also be selected from R DABNA-1 R DABNA -2 R DABNA-3 R DABNA-4 R DABNA-5 and R DABNA-6 Any aromatic or heteroaromatic substituent (specifically, R) DABNA-3 ), or any aromatic or heteroaromatic ring formed by two or more adjacent substituents as described above, wherein the shared ring may constitute the same or different parts of two or more structures of the shared ring of formula DABNA-I (i.e., the shared ring may be, for example, ring C' of two structures of formula DABNA-I optionally included in the emitter, or the shared ring may be, for example, ring B' of one structure of formula DABNA-I and ring C' of another structure optionally included in the emitter).
[1069] In one embodiment of the invention, one or more small FWHM emitters S are located in at least one light-emitting layer B (preferably, each light-emitting layer B). B At least one of them (preferably one or more small FWHM emitters S) BEach of the following includes two or more structures (i.e., sub-units) according to DABNA-I (preferably exactly two structures (i.e., sub-units) according to DABNA-I, or is composed of two or more structures (i.e., sub-units) according to DABNA-I (preferably exactly two structures (i.e., sub-units) according to DABNA-I).
[1070] Among them, R DABNA-1 R DABNA-2 R DABNA-3 R DABNA-4 R DABNA-5 and R DABNA-6 At least one of them is replaced by a bond attached to another chemical entity of the formula DABNA-I, and / or wherein R DABNA-1 R DABNA-2 R DABNA-3 R DABNA-4 R DABNA-5 and R DABNA-6 At least one hydrogen atom in any of them is replaced by a bond attached to another chemical entity of the formula DABNA-I.
[1071] The following lists the small FWHM emitters S that can be used according to the present invention. B Non-limiting examples of emitters including structures according to Formula DABNA-I or structures composed of Formula DABNA-I.
[1072]
[1073]
[1074]
[1075]
[1076]
[1077]
[1078]
[1079]
[1080]
[1081]
[1082]
[1083]
[1084]
[1085]
[1086]
[1087]
[1088]
[1089]
[1090]
[1091]
[1092] Small FWHM emitter S can be used as a context in this invention. B A group of emitters comprises a structure according to formula BNE-1 or a polymer thereof, or an emitter composed of a structure according to formula BNE-1 or a polymer thereof:
[1093]
[1094] in,
[1095] c and d are both integers and are independently selected from 0 and 1;
[1096] e and f are both integers and are selected from 0 and 1, where e and f are (always) the same (i.e., both are 0 or both are 1);
[1097] g and h are both integers and are selected from 0 and 1, where g and h are (always) the same (i.e., either both are 0 or both are 1);
[1098] If d is 0, then both e and f are 1; if d is 1, then both e and f are 0.
[1099] If c is 0, then both g and h are 1; if c is 1, then both g and h are 0.
[1100] V 1 Selected from nitrogen (N) and CR BNE-V ;
[1101] V 2 Selected from nitrogen (N) and CR BNE-I ;
[1102] X 3 Selected from direct-connect key, CR BNE-3 R BNE-4 C = CRBNE-3 R BNE-4 C=O, C=NR BNE-3 NR BNE-3 O, SiR BNE -3 R BNE-4 A group consisting of S, S(O) and S(O)2;
[1103] Y 2 Selected from direct-connect key, CR BNE-3′ R BNE-4′ C = CR BNE-3′ R BNE-4′ C=O, C=NR BNE-3′ NR BNE-3′ O, SiR BNE-3′ R BNE-4′ A group consisting of S, S(O) and S(O)2;
[1104] R BNE-1 R BNE-2 R BNE-1′ R BNE-2′ R BNE-3 R BNE-4 R BNE-3′ R BNE-4′ R BNE-I R BNE-II R BNE-III R BNE-IV and R BNE-V Each of these elements is independently selected from the group consisting of: hydrogen; deuterium; N(R) BNE-5 )2; OR BNE-5 ;Si(R) BNE-5 )3;B(OR BNE -5 )2;B(R BNE-5 )2; OSO2R BNE-5 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE -5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C1-C40 Alkoxy, optionally substituted with one or more substituents R BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE -5 )2、Ge(R BNE-5 )2、Sn(R BNE-5)2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R BNE-5 ; and C2-C 57 Heteroaryl, optionally substituted with one or more substituents R BNE-5 ;
[1105] R BNE-d R BNE-d′ and R BNE-e They are selected independently from the group consisting of: hydrogen; deuterium; N(R) BNE-5 )2; OR BNE-5 ;Si(R) BNE-5 )3;B(OR BNE-5 )2;B(R BNE-5 )2; OSO2R BNE-5 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R BNE-a And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE -5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R BNE-a And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C1-C 40Thioalkoxy groups, optionally substituted with one or more substituents R BNE-a And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R BNE-a And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. BNE-a And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE -5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R BNE-a ; and C2-C 57 Heteroaryl, optionally substituted with one or more substituents R BNE-a ;
[1106] R BNE-a Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) BNE-5 )2; ORBNE-5 ;Si(R) BNE-5 )3;B(OR BNE-5 )2;B(R BNE-5 )2; OSO2R BNE-5 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE -5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R BNE-5And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE-5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. BNE-5 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-5 C = CR BNE -5 C≡C, Si(R) BNE-5 )2、Ge(R BNE-5 )2、Sn(R BNE-5 )2. C=O, C=S, C=Se, C=NR BNE-5 P(=O)(R) BNE-5 SO, SO2, NR BNE-5 O, S or CONR BNE-5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R BNE-5 ; and C2-C 57 Heteroaryl, optionally substituted with one or more substituents R BNE-5 ;
[1107] R BNE-5 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) BNE-6 )2; OR BNE-6 ;Si(R) BNE-6 )3;B(OR BNE-6 )2;B(R BNE-6 )2; OSO2R BNE-6 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R BNE-6 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-6 C = CR BNE-6 C≡C, Si(R) BNE-6 )2、Ge(R BNE-6 )2、Sn(R BNE-6 )2. C=O, C=S, C=Se, C=NR BNE-6P(=O)(R) BNE -6 SO, SO2, NR BNE-6 O, S or CONR BNE-6 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R BNE-6 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-6 C = CR BNE-6 C≡C, Si(R) BNE-6 )2、Ge(R BNE-6 )2、Sn(R BNE-6 )2. C=O, C=S, C=Se, C=NR BNE-6 P(=O)(R) BNE-6 SO, SO2, NR BNE-6 O, S or CONR BNE-6 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R BNE-6 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-6 C = CR BNE-6 C≡C, Si(R) BNE-6 )2、Ge(R BNE-6 )2、Sn(R BNE-6 )2. C=O, C=S, C=Se, C=NR BNE-6 P(=O)(R) BNE-6 SO, SO2, NR BNE-6 O, S or CONR BNE-6 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R BNE-6 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-6 C = CR BNE-6 C≡C, Si(R) BNE-6 )2、Ge(R BNE-6 )2、Sn(R BNE-6 )2. C=O, C=S, C=Se, C=NR BNE-6 P(=O)(R) BNE-6 SO, SO2, NR BNE-6 O, S or CONR BNE-6 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. BNE-6 And wherein, one or more non-adjacent CH2 groups are optionally R BNE-6 C = CR BNE-6 C≡C, Si(R) BNE-6 )2、Ge(R BNE-6 )2、Sn(R BNE-6 )2. C=O, C=S, C=Se, C=NR BNE-6 P(=O)(R) BNE-6 SO, SO2, NR BNE-6 O, S or CONR BNE-6 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R BNE-6 ; and C2-C 57 Heteroaryl, optionally substituted with one or more substituents R BNE-6 ;
[1108] R BNE-6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3, Ph or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C6-C 18 Aryl group, optionally substituted with one or more C1-C5 alkyl substituents; C2-C 17 Heteroaryl groups, optionally substituted with one or more C1-C5 alkyl substituents; N(C6-C 18 Aryl)2; N(C2-C 17 (heteroaryl)2; and N(C2-C 17 (C6-C) 18 (Aromatic);
[1109] Among them, R BNE-III and R BNE-e Optionally, they can be combined to form a direct-connected single bond; and
[1110] Among them, substituent R BNE-a R BNE-d R BNE-d′ R BNE-e R BNE-3′ R BNE-4′ and R BNE-5Two or more of them may optionally form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzofused ring system;
[1111] Among them, substituent R BNE-1 R BNE-2 R BNE-1′ R BNE-2′ R BNE-3 R BNE-4 R BNE-5 R BNE-I R BNE-II R BNE-III R BNE-IV and R BNE-V Two or more of them may optionally form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzofused ring system;
[1112] Optionally, two or more BNE-1 structures (preferably two BNE-1 structures) are conjugate to each other, and preferably, they are fused together by sharing at least one bond (more preferably, exactly one bond);
[1113] Optionally, two or more structures of formula BNE-1 (preferably two structures of formula BNE-1) exist in the emitter and share at least one aromatic ring or heteroaromatic ring (preferably exactly one aromatic ring or heteroaromatic ring) (i.e., the ring can be part of two structures of formula BNE-1), wherein the at least one aromatic ring or heteroaromatic ring is preferably any one of ring a, ring b, and ring c' of formula BNE-1, but may also be selected from R BNE-1 R BNE-2 R BNE-1′ R BNE-2′ R BNE -3 R BNE-4 R BNE-3′ R BNE-4′ R BNE-5 R BNE-6 R BNE-I R BNE-II R BNE-III R BNE-IV R BNE-V R BNE-a R BNE-e R BNE-d and R BNE-d′Any aromatic or heteroaromatic substituent, or any aromatic or heteroaromatic ring formed by two or more substituents as described above, wherein the shared ring may constitute the same or different parts of two or more structures of formula BNE-1 with the shared ring (i.e., the shared ring may be, for example, ring c' of two structures of formula BNE-1 optionally included in the emitter, or the shared ring may be, for example, ring b of one structure and ring c' of another structure of formula BNE-1 optionally included in the emitter); and
[1114] Optionally, R BNE-1 R BNE-2 R BNE-1′ R BNE-2′ R BNE-3 R BNE-4 R BNE-5 R BNE-3′ R BNE-4′ R BNE-6 R BNE-I R BNE-II R BNE-III R BNE-IV R BNE-V R BNE-a R BNE-e R BNE-d and R BNE-d′ At least one of them is replaced by a bond attached to another chemical entity of formula BNE-1, and / or wherein, optionally, R BNE-1 R BNE-2 R BNE-1′ R BNE-2′ R BNE-3 R BNE -4 R BNE-5 R BNE-3’ R BNE-4’ R BNE-6 R BNE-I R BNE-II R BNE-III R BNE-IV R BNE-V R BNE-a R BNE-e R BNE-d and R BNE-d’ At least one hydrogen atom in any of them is replaced by a bond attached to another chemical entity of formula BNE-1.
[1115] In one embodiment of the invention, one or more small FWHM emitters S B At least one of them includes a structure according to formula BNE-1.
[1116] In one embodiment of the invention, each small FWHM emitter SB Including the structure according to formula BNE-1.
[1117] In one embodiment of the invention, one or more small FWHM emitters S B At least one of them consists of a structure according to formula BNE-1.
[1118] In one embodiment of the invention, each small FWHM emitter S B It consists of the structure according to formula BNE-1.
[1119] In one embodiment of the invention, one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula BNE-1 or is composed of a structure according to formula BNE-1, V 1 It is CR BNE-V And V 2 It is CR BNE-I .
[1120] In one embodiment of the invention, one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula BNE-1 or is composed of a structure according to formula BNE-1, V 1 and V 2 Both are nitrogen (N).
[1121] In one embodiment of the invention, one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula BNE-1 or is composed of a structure according to formula BNE-1, V 1 It is nitrogen (N), and V 2 It is CR BNE-I .
[1122] In one embodiment of the invention, one or more small FWHM emitters S B At least one of them (preferably one or more small FWHM emitters S) B Each of the following includes a structure according to formula BNE-1 or is composed of a structure according to formula BNE-1, V 1 It is CR BNE-V And V 2 It is nitrogen (N). ...
Claims
1. An organic electroluminescent device, said organic electroluminescent device comprising at least one light-emitting layer B composed of one or more sublayers, wherein, The one or more sublayers are adjacent to each other and, as a whole, contain the following components (i), (ii), and (iii) or, as a whole, contain the following components (i), (ii), (iii), and (iv): (i) at least one main material H B It has the lowest excited singlet state energy level E(S1) H ) and the lowest excited triplet energy level E(T1) H ); (ii) at least one phosphorescent material P B It has the lowest excited singlet state energy level E(S1) P ) and the lowest excited triplet energy level E(T1) P ); (iii) At least one small half-peak full-width emitter S B It has the lowest excited singlet state energy level E(S1) S ) and the lowest excited triplet energy level E(T1) S ), where S B Emitting light with a full width at half maximum (FWHM) of less than or equal to 0.25 eV; and (iv) At least one thermally activated delayed fluorescent material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ), The one or more sublayers located on the outer surface of the light-emitting layer B contain materials selected from phosphorescent materials P. B Small half-peak full-width emitter S B and thermally activated delayed fluorescent material E B At least one material in the group, Wherein, the at least one main material H B It has an energy E of less than -5.60 eV HOMO (H B The highest occupied molecular orbital (HOMO) of H B ), The relationship represented by the following equation (2) applies: E(T1 P ) > E(S1 S ) (2), Wherein, the at least one H B It is the main body H P The p-body H P Includes or consists of the following parts: A first chemical part, including according to formula H P -I, Formula H P -II, Formula H P -III, Formula H P -IV, Formula H P -V, Formula H P -VI, Formula H P -VII, Equation H P -VIII, Formula H P -IX and H P The structure of any one of -X, or according to formula H P -I, Formula H P -II, Formula H P -III, Formula H P -IV, Formula H P -V, Formula H P -VI, Formula H P -VII, Equation H P -VIII, Formula H P -IX and H P The structure of any one of -X: Formula H P -I Formula H P -II Formula H P -III Formula H P -IV Formula H P -V type H P -VI H P -VII Formula H P -VIII formula H P -IX H P -X; as well as One or more second chemical parts, each comprising, according to formula H P -XI, Formula H P -XII, Formula H P -XIII, formula H P -XIV, Formula H P -XV, Formula H P -XVI, H P -XVII, Formula H P -XVIII and H P The structure of any one of -XIX, or by means of equation H P -XI, Formula H P -XII, Formula H P -XIII, formula H P -XIV, Formula H P -XV, Formula H P -XVI, H P -XVII, Formula H P -XVIII and H P The structure of any one of -XIX: Formula H P -XI formula H P -XII Formula H P -XIII Formula H P -XIV formula H P -XV formula H P -XVI Formula H P -XVII Formula H P -XVIII Formula H P -XIX, Among them, it exists in the p-body H P Each of the at least one second chemical part is connected to the first chemical part via a single bond, which is represented by a dashed line in the above formula; wherein, Z 1 Each time they appear, they are independently selected from the direct connection key, C(R) II 2. C = C(R) II 2. C=O, C=NR II NR II O, Si(R) II )2, a group consisting of S, S(O) and S(O)2; R I Each time it appears, it is an independent bonding site that connects the first chemical part to the single bond of the second chemical part, or is selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, unsubstituted or substituted with one or more substituents independently selected from the group consisting of: Me; i Pr; t Bu; and Ph; Among them, at least one R I It is the binding site that connects the first chemical part to the single bond of the second chemical part; R II Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, unsubstituted or substituted with one or more substituents independently selected from the group consisting of: Me; i Pr; t Bu; and Ph.
2. The organic electroluminescent device according to claim 1, wherein, At least one of the one or more sublayers of the at least one light-emitting layer B comprises the following components: (iv) At least one thermally activated delayed fluorescent material E B It has the lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet energy level E(T1) E ).
3. The organic electroluminescent device according to claim 1, wherein, The at least one thermally activated delayed fluorescence material E B : (i) Characterized by exhibiting a ΔE less than 0.4 eV. ST The value, the ΔE ST The value corresponds to the lowest excited singlet state energy level E(S1). E ) and the lowest excited triplet energy level E(T1) E The energy difference between them; and (ii) It exhibits a photoluminescence quantum yield of more than 30%.
4. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The following relationships, represented by equations (1) and (3), apply: E(T1 H ) > E(T1 P ) (1) E(T1 H ) > E(T1 E ) (3).
5. The organic electroluminescent device according to any one of claims 1 to 3, wherein, At least one sublayer includes exactly one thermally activated delayed fluorescent material E B And exactly one phosphorescent material P B .
6. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The sublayer includes exactly one thermally activated delayed fluorescent material E B And the sublayer includes exactly one phosphorescent material P B And exactly one half-peak full-width emitter S B .
7. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The following relationships, represented by equations (3) and (4), apply: E(T1 H ) > E(T1 E ) (3) E(T1 E ) > E(T1 P ) (4).
8. The organic electroluminescent device according to any one of claims 1 to 3, wherein: (i) the at least one host material H B It has energy E HOMO (H B The highest occupied molecular orbital (HOMO) of H B ); (iii) The at least one phosphorescent material P B It has energy E HOMO (P B The highest occupied molecular orbital (HOMO) of P) B );and (iv) The at least one small half-peak full-width emitter S B It has energy E HOMO (S B The highest occupied molecular orbital (HOMO) of ) B ); The relationship represented by the following equations (10) and (11) applies: E HOMO (P B ) > E HOMO (H B ) (10) AND HOMO (P B ) > E HOMO (S B ) (11)。 9. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The relationship expressed by equation (4) applies: E(T1 E ) > E(T1 P ) (4).
10. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The at least one small half-peak full-width emitter S B At least one of the following requirements must be met: (i) It is a boron-containing emitter, which means that the full width at half maximum (FWHM) of each small half-peak emitter S B At least one atom in it is boron; and (ii) It includes a polycyclic aromatic or heterocyclic aromatic core structure, wherein at least two aromatic rings are fused together.
11. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The one or more sublayers as a whole comprise or consist of the following components: (i) 60% to 99.8% by weight of one or more main materials H B ; (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ;and (iii) 0.1 wt% to 10 wt% of one or more small half-peak full-width emitters S B .
12. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The one or more sublayers as a whole comprise or consist of the following components: (i) 60% to 99.8% by weight of one or more main materials H B ; (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ; (iii) 0.1 wt% to 10 wt% of one or more small half-peak full-width emitters S B ;as well as (iv) 0% to 69.8% by weight of one or more thermally activated delayed fluorescent materials E B .
13. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The one or more sublayers as a whole comprise or consist of the following components: (i) 60% to 99.8% by weight of one or more main materials H B ; (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ; (iii) 0.1 wt% to 10 wt% of one or more small half-peak full-width emitters S B ;as well as (v) 0% to 69.8% by weight of one or more solvents.
14. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The one or more sublayers as a whole comprise or consist of the following components: (i) 60% to 99.8% by weight of one or more main materials H B ; (ii) 0.1% to 30% by weight of one or more phosphorescent materials P B ; (iii) 0.1 wt% to 10 wt% of one or more small half-peak full-width emitters S B ; (iv) 0% to 69.8% by weight of one or more thermally activated delayed fluorescent materials E B ;as well as (v) 0% to 69.8% by weight of one or more solvents.
15. The organic electroluminescent device according to any one of claims 1 to 3, wherein, The at least one light-emitting layer B consists of exactly one layer.
16. A method for generating light, the method comprising the steps of: (i) Providing an organic electroluminescent device according to any one of claims 1 to 15; and (ii) Apply current to the organic electroluminescent device.
17. The method according to claim 16, wherein, The method is used to generate light in a wavelength range selected from one of the following wavelength ranges: (i) 510nm to 550nm; or (ii) 440nm to 470nm; or (iii) 610nm to 665nm.
Citation Information
Patent Citations
Organic electroluminescence device
EP1205527A1
Aromatic compounds and organic electronic device using the same
EP2182040A2
Organic electroluminescent element
EP2690681A1
Iridium complexes with aza-benzo fused ligands
EP2730583A1
Polycyclic aromatic compound
EP3109253A1
