Green light emitting organic electroluminescent element
By integrating a TADF material with a small FWHM emitter and an exciton management layer in OLEDs, the devices achieve narrow emission and long lifetime, addressing the limitations of broad spectra and high brightness challenges, and reducing transition metal reliance.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2021-09-17
- Publication Date
- 2026-04-08
AI Technical Summary
Existing organic electroluminescent devices, particularly OLEDs, face challenges in achieving high efficiency, long lifetime, and excellent color purity due to broad emission spectra and the use of expensive transition metal-based phosphorescent materials, which are not effective at higher brightness levels and suffer from exciton-polaron annihilation.
Incorporating a TADF material with a small full width at half maximum (FWHM) emitter and an exciton management layer containing a triplet-triplet annihilation material in the light-emitting layer, which transfers excitation energy to a narrow emission spectrum emitter, achieving long lifetime and high quantum yield.
The solution enables organic electroluminescent devices to exhibit narrow emission suitable for BT-2020 and DCPI3 color regions, enhancing efficiency and longevity while reducing the need for expensive transition metals.
Smart Images

Figure 0007842743000001 
Figure 0007842743000002 
Figure 0007842743000003
Abstract
Description
[Technical Field]
[0001] This invention relates to TADF material E B A small FWHM emitter S that emits green light and has a FWHM of 0.25 eV or less. B , and host material H B The present invention relates to an organic electroluminescent element including a light-emitting layer B containing a triplet-triplet annihilation material. Furthermore, the organic electroluminescent element according to the present invention includes an exciton management layer adjacent to the light-emitting layer B, which contains a triplet-triplet annihilation material. The present invention also relates to a method for manufacturing an organic electroluminescent element and a method for generating green light using the organic electroluminescent element according to the present invention. [Overview of the project] [Problems that the invention aims to solve]
[0002] For example, organic electroluminescent devices that include one or more light-emitting layers using organic materials, such as organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors, are becoming increasingly important. OLEDs, in particular, are promising devices for electronic products such as screens, displays, and lighting devices. In contrast to most electroluminescent devices that use substantially inorganic materials, organic electroluminescent devices that use organic materials can usually be produced in a flexible and especially thin film. Screens and displays using OLEDs already available today offer excellent efficiency and long lifespan, or excellent color purity and long lifespan, but they do not possess all three characteristics.
[0003] While the color purity or color point of an OLED is generally provided by CIEx and CIEy coordinates, the color gamut of next-generation displays is provided by so-called BT-2020 and DCPI3 values. Generally, obtaining such color coordinates requires modifying the cavity of a top-emission element and adjusting the color coordinates. To achieve high efficiency in a top-emission element while targeting such a color gamut, a narrow emission spectrum is required in a bottom-emission element.
[0004] Modern phosphorescent emitters exhibit somewhat broad emission, which is reflected in the broad emission of phosphorescent-based OLEDs (PHOLEDs), which generally have a full width at half maximum (FWHM) of emission spectra greater than 0.25 eV. The broad emission spectrum of PHOLEDs in the bottom element results in a significant loss of outcoupling efficiency for top-emission element structures targeting the BT-2020 and DCPI three-color regions.
[0005] Furthermore, phosphorescent materials typically utilize transition metals, such as iridium, which are generally not abundant and therefore very expensive materials within OLED stacks. Consequently, transition metal-based materials offer the greatest potential for cost reduction in OLEDs. Reducing the transition metal content within OLED stacks is a key performance indicator for determining the value of OLED application products.
[0006] In recent years, some fluorescent emitters or TADF (thermally-activated-delayed-fluorescence) emitters exhibiting somewhat narrow emission spectra have been developed. These generally exhibit FWHM with emission spectra below 0.25 eV and are therefore suitable for achieving the BT-2020 and DCPI three-color regions. However, such fluorescent emitters and TADF emitters generally have short lifetimes due to exciton-polaron annihilation or exciton-exciton annihilation, and are not effective at higher brightness levels. Due to the rate of change (i.e., the roll-off behavior of the OLED), it suffers from the problem of low efficiency.
[0007] Such disadvantages can be overcome to some extent by applying a so-called hyper-approach. The latter, as mentioned above, preferably relies on the use of an energy pump that transfers energy to a fluorescent emitter exhibiting a narrow emission spectrum. The energy pump may be, for example, a TADF material exhibiting reverse-intersystem crossing (RISC) or a transition metal complex exhibiting efficient intersystem crossing (ISC). However, such an approach still cannot provide an organic electroluminescent device that possesses all of the aforementioned desirable characteristics, namely, excellent efficiency, long lifetime, and excellent color purity.
[0008] The central element of an organic electroluminescent element for generating light is typically at least one light-emitting layer located between the positive and negative electrodes. When a voltage (and current) is applied to the organic electroluminescent element, holes are injected from the positive electrode and electrons are injected from the negative electrode. Typically, the hole transport layer is located between the light-emitting layer and the positive electrode, and the electron transport layer is typically located between the light-emitting layer and the negative electrode. Different layers are arranged sequentially. High-energy excitons are generated in the light-emitting layer by the recombination of holes and electrons. Light emission is preferably induced by decaying such excited states (e.g., singlet states such as S1 and / or triplet states such as T1) to a ground state (S0). [Means for solving the problem]
[0009] Surprisingly, TADF material E B A small FWHM emitter S that emits green light and has a FWHM of 0.25 eV or less. B , and host material H BAn organic electroluminescence device including a light-emitting layer containing [substance], and an exciton management layer EXL adjacent to the light-emitting layer, has been found to be ideally suitable for achieving a long lifetime, high quantum yield, and narrow emission in the green BT-2020 and DCPI3 color regions.
[0010] Here, the TADF material E B can transfer excitation energy to a small FWHM (full width at half maximum) emitter S B that emits light.
Embodiments for Carrying out the Invention
[0011] The present invention relates to an organic electroluminescence device including a light-emitting layer B including the following: (i) A TADF material E E having a lowest excited singlet state energy level E(S1 E ) and a lowest excited triplet state energy level E(T1 B ), (ii) A small full width at half maximum (FWHM) emitter S S having a lowest excited singlet state energy level E(S1 S ) and a lowest excited triplet state energy level E(T1 B ) and emitting light having a maximum emission at 510 nm to 550 nm and a full width at half maximum (FWHM) of <0.25 eV, and (iii) A host material H H having a lowest excited singlet state energy level E(S1 H ) and a lowest excited triplet state energy level E(T1 B ), where the organic electroluminescence device includes an exciton management layer EXL adjacent to the light-emitting layer B and containing a triplet-triplet annihilation (TTA) material.
[0012] If the aforementioned requirements are met, an organic electroluminescent element can be obtained that exhibits a long lifetime, high quantum yield, and narrow emission, making it ideally suited for achieving the green BT-2020 and DCPI three-color regions.
[0013] Throughout this specification, we will refer to the relationships between the energies of the excited states, orbitals, and maximum luminescence of the components in the light-emitting layer B of the organic electroluminescent element according to the present invention. It will be understood that a relationship involving the energies of two specific components applies only to a light-emitting layer B that contains both of those specific components. Furthermore, the fact that a relationship applies to an element according to the present invention does not mean that all elements of the present invention must contain all the components mentioned in that relationship. Such general matters are applicable to all embodiments of the present invention.
[0014] element structure Those skilled in the art will see that the light-emitting layer B is typically included in the organic electroluminescent element of the present invention. Preferably, the organic electroluminescent element includes at least the following layers: At least one light-emitting layer B, at least one anode layer A, and at least one cathode layer C.
[0015] Preferably, the light-emitting layer B is located between the anode layer A and the cathode layer C. Therefore, a common configuration is preferably ABC. This, of course, does not rule out the presence of one or more selective additional layers. They may be present on each side of A, B, and / or C.
[0016] Preferably, the anode layer A is located on the surface of the substrate. The substrate may be formed of any material or a composition of such material. Most often, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver, or aluminum film), or a plastic film or plastic slide may be used. It can allow for an even higher level of flexibility. At least one of the two electrodes must be (essentially) transparent so as to emit light from the electroluminescent element (e.g., OLED). Typically, the anode layer A is composed of a material from which a nearly (essentially) transparent film can be obtained. Preferably, the anode layer A contains or is composed of a large amount of transparent conductive oxide (TCO).
[0017] Such an anode layer A may include, for example, indium tin oxide, aluminum zinc oxide, fluorine tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene, and mixtures of two or more of these.
[0018] Particularly preferred is that the anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO3) 0.9 (SnO2) 0.1The anode layer A is composed of a transparent conductive oxide (TCO). The roughness of the anode layer A due to the transparent conductive oxide (TCO) may be mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of similar charge carriers (i.e., holes) from the TCO to the hole transport layer (HTL). The hole injection layer (HIL) may contain poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonic acid (PSS), MoO2, V2O5, CuPC, or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent the diffusion of metal from the anode layer A to the hole transport layer (HTL). For example, the HIL is poly-3,4-ethylenedioxythiophene:polystyrene sulfonic acid (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine n(mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-nis-(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N It may also consist of N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonnitrile (HAT-CN), and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).
[0019] Adjacent to the anode layer A or hole injection layer (HIL), generally, a hole transport layer (HTL) is located. Here, any hole transport compound can be used. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles may be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer B (which acts as the light-emitting layer (EML)). The hole transport layer (HTL) may also be an electron-barrier layer (EBL). Preferably, the hole transport compound has a triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) is tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4'-cyclohexyllidene-bis[N,N-bis(4-methylphenyl)benzeneamine] (TAPC), 4,4',4”-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN and / or 9,9'-diphenyl-6-(9-phenyl-9H The HTL may also contain a star-shaped heterocycle such as -carbazole-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also contain a p-doped layer which may be composed of inorganic or organic dopants within the organic hole transport matrix. Examples of inorganic dopants include transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide. Examples of organic dopants include tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoic acid (Cu(I)pFBz), or transition metal complexes.
[0020] The electron barrier layer (EBL) is, for example, 1,3-bis(carbazole-9-yl)benzene (mCP), TCTA, 2-TNATA, 3,3-di(9H-carbazole-9-yl)biphenyl (mCBP), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, tris-Pcz, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi) and / or It may also contain N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).
[0021] The composition of one or more light-emitting layers B has been described above. Any one or more light-emitting layers B according to the present invention preferably have a thickness of 1 mm or less, more preferably 0.1 mm or less, even more preferably 10 μm or less, still more preferably 1 μm or less, and particularly preferably 0.1 μm or less.
[0022] Any electron transporter can be used in the electron transport layer (ETL). For example, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone can be used. For example, the electron transporter ETM (i.e., electron transport material) is also a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)phenyl (TPBi). ETM may include, for example, 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq3), diphenyl-4-triphenylsilylphenylphosphine oxide (TSPO1), 2,7-di(2,2'-bipyridine-5-yl)triphenyl (BPyTP2), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene (BmPyPhB) and / or 4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl (BTB). Selectively, the electron transport layer may also be doped with a material such as 8-hydroxyquinolinolatritium (Liq). Selectively, a second electron transport layer may be located between the electron transport layer and the cathode layer C. The electron transport layer (ETL) can also block holes. Alternatively, a hole blocking layer (HBL) may be introduced.
[0023] HBL is, for example, HBM1: JPEG0007842743000001.jpg3031, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=basocupproine (BCP), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline)(Alq3), diphenyl-4-triphenylsilylphenylphosphine oxide (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3, It may also contain 5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifloren-2-yl)-1,3,5-triazine (TST), 2,4-diphenyl-6-(3'-triphenylsilylphenyl)-1,3,5-triazine (DTST), 2,8-bis(4,6-diphenyl-1,3,5-triazinyl)dibenzofuran (DTDBF) and / or 1,3,5-tris(N-carbazol)benzol / 1,3,5-tris(carbazole)-9-yl)benzene (TCB / TCP).
[0024] Adjacent to the electron transport layer (ETL), a cathode layer C may be located. The cathode layer C may contain, or be composed of, a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer C may be composed of an (essentially) opaque metal such as Mg, Ca, or Al. Alternatively, or even further, the cathode layer C may also contain graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also be composed of nanoscale silver wire.
[0025] In a preferred embodiment, the organic electroluminescent element includes at least the following layers: A) Anode layer A comprising at least one component selected from the group consisting of indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped silicon, doped germanium, doped GaAs, doped polyaniline, doped polypyrrole, doped polythiophene, and mixtures of two or more thereof. EXL) Exciton management layer EXL according to the present invention as described herein, B) The light-emitting layer B according to the present invention as described herein, and C) Cathode layer C comprising at least one component selected from the group consisting of Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd, LiF, Ca, Ba, Mg and mixtures or alloys of two or more thereof, Here, the light-emitting layer B is located between the anode layer A and the cathode layer C.
[0026] In a preferred embodiment, the organic electroluminescent element includes at least the following layers: A) Anode layer A comprising at least one component selected from the group consisting of indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped silicon, doped germanium, doped GaAs, doped polyaniline, doped polypyrrole, doped polythiophene, and mixtures of two or more thereof. B) The light-emitting layer B according to the present invention as described in this application, EXL) Exciton management layer EXL according to the present invention as described herein, and C) Cathode layer C comprising at least one component selected from the group consisting of Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd, LiF, Ca, Ba, Mg and mixtures or alloys of two or more thereof, Here, the light-emitting layer B is located between the anode layer A and the cathode layer C.
[0027] In a preferred embodiment, the organic electroluminescent element is an OLED having the following layer structure: A) For example, an anode layer A containing indium tin oxide (ITO), HTL) Hole transport layer HTL, EXL) Exciton management layer EXL according to the present invention as described herein, B) The light-emitting layer B according to the present invention as described in this application, ETL (Electron Transport Layer), C) For example, a cathode layer C containing Al, Ca and / or Mg.
[0028] Preferably, the order of the layers here is A-HTL-EXL-B-ETL-C.
[0029] In one embodiment, the organic electroluminescent element is an OLED having the following layer structure: A) For example, an anode layer A containing indium tin oxide (ITO), HTL) Hole transport layer HTL, B) The light-emitting layer B according to the present invention as described in this application, EXL) Exciton management layer EXL according to the present invention as described herein, ETL (Electron Transport Layer), C) For example, a cathode layer C containing Al, Ca and / or Mg.
[0030] Preferably, the order of the layers here is A-HTL-B-EXL-ETL-C.
[0031] In one embodiment, the exciton management layer EXL has a thickness of less than 15 nm.
[0032] In a preferred embodiment, the exciton control layer EXL has a thickness of less than 10 nm.
[0033] In a preferred embodiment, the exciton control layer EXL has a thickness of 5 nm or less.
[0034] In a preferred embodiment, the exciton control layer EXL has a thickness of less than 5 nm.
[0035] As is known to those skilled in the art, TTA material is used as host material H B It can be used as such. TTA material enables triplet-triplet annihilation. Triplet-triplet annihilation can preferably cause photon upconversion. Thus, two, three or more photons can be converted into TTA material H TTA The lowest excited triplet state (T1 TTA ) to the first excited singlet state (S1 TTA Facilitates photon upconversion to ). In a preferred embodiment, two photons TTA From S1 TTA This facilitates photon upconversion to triplet. Therefore, triplet-triplet annihilation may be a process that can couple two (or, selectively, more than two) low-frequency photons into one high-frequency photon via a number of energy transfer steps.
[0036] Selectively, the TTA material may also include an absorbent substructure, a sensitizer substructure, and a luminescent substructure (or a desensitizer substructure). In this regard, the luminescent substructure may be a polycyclic aromatic substructure such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, or azulene. In a preferred embodiment, the polycyclic aromatic substructure includes an anthracene substructure or a derivative thereof. The sensitizer substructure and the luminescent substructure may be located in two different chemical compounds (i.e., separate chemical entities) or may be two substructures contained within a single compound.
[0037] According to the present invention, the TTA material is in the lowest excited triplet state (T1 N ) shows triplet-triplet vanishing from T1 N S1 is a triplet-triplet annihilated first excited singlet state with up to twice the energy of the first excited state. N It is characterized by forming a structure.
[0038] According to the present invention, triplet-triplet annihilation (TTA) materials undergo triplet-triplet annihilation to reach the first excited triplet state T1 N From the first excited singlet state S1 N It converts energy into [something].
[0039] In one embodiment of the present invention, the TTA material is T1 N From there, we can show the triplet-triplet annihilation of S1 N It is characterized by generating, where S1 N T1 N It has 1.01 to 2 times, 1.1 to 1.9 times, 1.2 to 1.5 times, 1.4 to 1.6 times, or 1.5 to 2 times the energy of the original.
[0040] In this application, the terms "TTA material" and "TTA compound" are interchangeable and can be used interchangeably.
[0041] Typical "TTA materials" can be found in the latest technologies related to blue fluorescent OLEDs, as described by Kondakov (Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences, 2015, 373: 20140321). Such blue fluorescent OLEDs use aromatic hydrocarbons, such as anthracene derivatives, as the main component (host) of the EML.
[0042] In a preferred embodiment, the TTA material enables sensitized triplet-triplet annihilation. Selectively, the TTA material may contain one or more polycyclic aromatic structures. In a preferred embodiment, the TTA material contains at least one polycyclic aromatic structure and a few It contains at least one additional aromatic residue.
[0043] In a preferred embodiment of the present invention, TTA material H TTA It is an anthracene derivative.
[0044] In one embodiment, TTA material H TTA It is an anthracene derivative with the following chemical formula TTA. [ka] ···Chemical formula TTA
[0045] Here, Each Ar is independently selected from the group consisting of the following: C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C6-C 60 Aryl, and C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C3-C 57 Heteroaryl, Each A1 is independently selected from the following group: hydrogen, deuterium, C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C6-C 60 Ariel, C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C3-C 57 Heteroaryls, and C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40C1-C 40 (Hetero)alkyl.
[0046] In one embodiment, TTA material H TTA It is an anthracene derivative with the following chemical formula TTA, where, Each Ar is independently selected from the group consisting of the following: C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C6-C 60 Aryl, and C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C3-C 57 Heteroaryl, Each A1 is independently selected from the following group: hydrogen, deuterium, C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C6-C 60 Ariel, C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 C3-C 57 Heteroaryls, and C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40C1-C 40 (Hetero)alkyl.
[0047] In one embodiment, H TTA is an anthracene derivative of the following chemical formula TTA, where at least one A1 is hydrogen. In one embodiment, H TTA is an anthracene derivative of the following chemical formula TTA, where at least two A1s are hydrogen. In one embodiment, H TTA is an anthracene derivative of the following chemical formula TTA, where at least three A1s are hydrogen. In one embodiment, H TTA It is an anthracene derivative with the following chemical formula TTA, where all A1s are hydrogen atoms.
[0048] In one embodiment, H TTA It is an anthracene derivative with the following chemical formula TTA, where one Ar is C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40 These are residues selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, triphenylenyl, dibenzoanthracenyl, fluorenyl, benzofluorenyl, anthracenyl, phenantrenyl, benzonaphthofuranil, benzonaphthothiophenyl, dibenzofuranil, and dibenzothiophenyl, each selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups.
[0049] In one embodiment, H TTA It is an anthracene derivative with the following chemical formula TTA, where the two Ar groups are independently C6-C 60 Ariel, C3-C 57 Heteroaryls, halogens, and C1-C 40A residue selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, triphenylenyl, dibenzoanthracenyl, fluorenyl, benzofluorenyl, anthracenyl, phenanthrenyl, benzonaphthofuranyl, benzonaphthothiophenyl, dibenzofuranyl, dibenzothiophenyl, each selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl.
[0050] In one embodiment, the TTA material H TTA is an anthracene derivative selected from the following:
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
Chemical formula
change
change
change
change
change
change
change
change
change
change
change
change
change
change
[0051] In one embodiment, the exciton control layer EXL includes a TTA material and an additional emitter.
[0052] In a preferred embodiment, the exciton control layer EXL comprises a TTA material and an additional emitter, where the additional emitter in the adjacent layer EXL is a small FWHM emitter S B This emits light with a full width at half maximum (FWHM) of 0.25 eV or less and a maximum emission in the 510-550 nm range.
[0053] Furthermore, the organic electroluminescent element may selectively include one or more protective layers to protect the element from damage exposure to harmful substances in the environment, such as moisture, vapor, and / or gases.
[0054] An electroluminescent device (e.g., an OLED) may optionally further include a protective layer (also called an electron injection layer (EIL)) between the electron transport layer (ETL) D and the cathode layer C. This layer may contain lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatritium (Liq), Li2O, BaF2, MgO, and / or NaF.
[0055] Unless otherwise specified, any layer including any sublayers of the various embodiments is deposited by any suitable method. Layers in the context of the present invention that consist of at least one light-emitting layer B (composed of a single (sub)layer or including one or more sublayers) and / or one or more sublayers thereof are selectively fabricated via liquid processing (also known as “film processing,” “fluid processing,” “solution processing,” or “solvent processing”). This means that the components contained in each layer are applied in a liquid state to a portion of the surface of the device.
[0056] Preferably, the layer in the context of the present invention comprises at least one light-emitting layer B and / or one or more sublayers thereof, and may be produced by spin coating. Thin and (essentially) uniform layers and / or sublayers can be obtained by such methods, which are well known to those skilled in the art.
[0057] Alternatively, the layers in the context of the present invention, which include at least one luminescent layer B and / or one or more sublayers thereof, may also be manufactured by other liquid-based methods such as casting (e.g., drop casting), rolling methods, and printing methods (e.g., inkjet printing, gravure printing, blade coating). This is selectively carried out in an inert atmosphere (e.g., a nitrogen atmosphere).
[0058] In other preferred embodiments, the layers in the context of the present invention, which include at least one light-emitting layer B and / or one or more sublayers thereof, may be manufactured by any other method well known to those skilled in the art, including, but not limited to, vacuum processing methods such as thermal (co)deposition, organic vapor deposition (OVPD), and organic vapor jet printing (OVJP).
[0059] One of the objectives of organic electroluminescent devices may be the production of organic electroluminescent devices via vacuum deposition.
[0060] Therefore, other aspects of the present invention relating to a method for generating an organic electroluminescent element include the following: (i) Deposition of the light-emitting layer B via vacuum deposition, and (ii) Deposition of the exciton control layer EXL via vacuum deposition, Here, steps (i) and (ii) are performed sequentially, The order of steps (i) and (ii) can be reversed.
[0061] In a preferred embodiment, an organic electroluminescent element is generated, where the light-emitting layer B is deposited via vacuum deposition, and then the exciton control layer EXL is deposited via vacuum deposition. In this embodiment, it will be understood that the exciton control layer EXL is preferably deposited on the light-emitting layer B via vacuum deposition. That is, it is preferable that the exciton control layer EXL is in direct contact with the light-emitting layer B. Therefore, the exciton control layers EXL are adjacent.
[0062] In a preferred embodiment, an organic electroluminescent element is generated, where an exciton control layer EXL is deposited via vacuum deposition, and then an emissive layer B is deposited via vacuum deposition. In this embodiment, it will be understood that the emissive layer B is preferably deposited on the exciton control layer EXL via vacuum deposition. That is, it is preferable that the exciton control layer EXL is in direct contact with the emissive layer B. Therefore, the exciton control layers EXL are adjacent.
[0063] When a layer containing one or more sublayers is produced by liquid processing, the components of the (sub)layer (i.e., one or more TADF materials E for the light-emitting layer B of the present invention) B , selectively one or more excitation energy transfer components EET-2, and one or more small FWHM emitters S B , and selectively one or more host materials H BThe solution containing may further contain a volatile organic solvent. Such a volatile organic solvent may be selectively one selected from the group consisting of tetrahydrofuran, dioxane, chlorobenzene, diethylene glycol diethyl ether, 2-(2-ethoxyethoxy)ethanol, γ-butyrolactone, N-methylpyrrolidinone, ethoxyethanol, xylene, toluene, anisole, phenetole, acetonitrile, tetrahydrothiophene, benzonitrile, pyridine, trihydrofuran, triarylamine, cyclohexanone, acetone, propylene carbonate, ethyl acetate, benzene, and propylene glycol monoethyl ether acetate (PGMEA). Also, a combination of two or more solvents may be used. After being applied in a liquid state, the layer is then dried and / or cured by any means in the art, for example, under atmospheric conditions, at an elevated temperature (e.g., about 50 °C or about 60 °C), or under reduced pressure.
[0064] The organic electroluminescent device can form a thin film with a thickness of 5 mm or less, 2 mm or less, 1 mm or less, 0.5 mm or less, 0.25 mm or less, 100 μm or 10 μm or less as a whole.
[0065] The organic electroluminescent device (e.g., OLED) may be small (e.g., having a surface area of 5 mm 2 or less, and even further 1 mm 2 or less), medium-sized (e.g., having a surface area in the range of 0.5 cm 2 to 20 cm 2 ), or large-sized (e.g., having a surface area larger than 20 cm 2 ). The organic electroluminescent device (e.g., OLED) according to the present invention may be selectively a large-area lighting device, a light-emitting wallpaper, a light-emitting window frame or glass, a light-emitting label, a light-emitting poster, or a flexible screen or display They can be used to generate screens. Beyond common applications, organic electroluminescent elements (e.g., OLEDs) may be used, for example, as light-emitting films, "smart packaging" labels, or innovative design elements. They can also be used for cell detection and inspection (e.g., biolabeling).
[0066] Composition of the Emitting Layer (EML) B In describing the composition of the light-emitting layer B of the organic electroluminescent element according to the present invention in more detail below, the content of specific materials will be shown as a percentage where appropriate. Unless otherwise specified for a particular embodiment, all percentages refer to weight percentages, which have the same meaning as weight percent or weight % ((weight / weight), (w / w), wt.%). For example, in a particular composition, one or more small FWHM emitters S B When the content is mentioned as 1% exemplarily, this refers to one or more small FWHM emitters S B (That is, all S B The sum of the molecules accounts for 1% by weight, i.e., 1% of the total weight of each luminescent layer B. Whenever the composition of luminescent layer B is specified by providing a preferred content of its components in weight percent, it is understood that the sum of the total content of all components will equal 100% by weight (i.e., the total weight of each luminescent layer B).
[0067] Host material H B , TADF material E B and small FWHM emitter S B This is included in the organic electroluminescent element according to the present invention in any amount and proportion.
[0068] In one embodiment, in the organic electroluminescent element according to the present invention, the light-emitting layer B includes or is composed of the following: (i) 12-60% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2, 0.0 to 30 wt% (iii) Small FWHM emitter S of 0.1-10% by weight B , (iv) 30-87.9% by weight of host material H B , and selectively (v) 0-57.9% by weight of 1 or more solvents, and selectively (vi) A material selected from the group consisting of TADF material, phosphorescent material, host material and small FWHM emitter, in an amount of 0 to 57.8% by weight (preferably different from the components (i) to (iv) described above).
[0069] In one embodiment, in the organic electroluminescent element according to the present invention, the light-emitting layer B includes or is composed of the following: (i) 12-60% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2, 0.0 to 30 wt% (iii) Small FWHM emitter S of 0.1-10% by weight B , (iv) 30-87.9% by weight of host material H B , and selectively (v) 0 to 57.9% by weight of 1 or more solvents.
[0070] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 12-60% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2, 0.0 to 30 wt% (iii) Small FWHM emitter S of 0.1-10% by weight B , (iv) 30-87.9% by weight of host material H B , and selectively (v) 0-3% by weight of 1 or more solvents
[0071] In one embodiment, in the organic electroluminescent element according to the present invention, the light-emitting layer B includes or is composed of the following: (i) 12-60% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2, 0.1 to 30% by weight (iii) Small FWHM emitter S of 0.1-10% by weight B , (iv) 30-87.8% by weight of host material H B , and selectively (v) 0 to 57.8% by weight of 1 or more solvents.
[0072] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 12-60% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2, 0.1 to 30% by weight (iii) Small FWHM emitter S of 0.1-10% by weight B , (iv) 30-87.8% by weight of host material H B , and selectively (v) 0-3% by weight of 1 or more solvents
[0073] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 15-50% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-15 wt%, (iii) Small FWHM emitter S of 0.1-5% by weight B , (iv) 30-84.8% by weight of host material H B , and selectively (v) 1 or more solvents in an amount of 0 to 54.8% by weight.
[0074] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 15-50% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-15 wt%, (iii) Small FWHM emitter S of 0.1-5% by weight B , (iv) 30-84.8% by weight of host material H B , and selectively (v) 0-3% by weight of 1 or more solvents
[0075] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 20-50% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-10 wt%, (iii) Small FWHM emitter S of 0.1-3% by weight B , (iv) 40-79.8% by weight of host material H B , and selectively (v) 0 to 39.8% by weight of 1 or more solvents.
[0076] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 20-50% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-10 wt%, (iii) Small FWHM emitter S of 0.1-3% by weight B , (iv) 40-79.8% by weight of host material H B , and selectively (v) 0-3% by weight of 1 or more solvents
[0077] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 20-45% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-5 wt%, (iii) Small FWHM emitter S of 0.1-3% by weight B , (iv) 40-79.8% by weight of host material H B , and selectively (v) 0 to 39.8% by weight of 1 or more solvents.
[0078] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 20-45% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-5 wt%, (iii) Small FWHM emitter S of 0.1-3% by weight B , (iv) 40-79.8% by weight of host material H B , and selectively (v) 0-7% by weight of 1 or more solvents
[0079] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 20-45% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-3 wt%, (iii) Small FWHM emitter S of 0.1-3% by weight B , (iv) 40-79.8% by weight of host material H B , and selectively (v) 0 to 39.8% by weight of 1 or more solvents.
[0080] In a preferred embodiment, the organic electroluminescent element according to the present invention comprises or is composed of the following: (i) 20-45% by weight of TADF material E B , (ii) Excitation energy transfer component EET-2 of 0.1-3 wt%, (iii) Small FWHM emitter S of 0.1-3% by weight B , (iv) 40-79.8% by weight of host material H B , and selectively (v) 0-9% by weight of 1 or more solvents
[0081] In a preferred embodiment of the present invention, the light-emitting layer B contains an excitation energy transfer component EET-2 of 5% by weight or less based on the total weight of the light-emitting layer B (meaning that the total content of EET-2 in each light-emitting layer B is 5% by weight or less).
[0082] In a preferred embodiment of the present invention, the light-emitting layer B contains an excitation energy transfer component EET-2 of 5% by weight or less based on the total weight of the light-emitting layer B (meaning that the total content of EET-2 in each light-emitting layer B is 5% by weight or less).
[0083] In a preferred embodiment of the present invention, the light-emitting layer B contains 3% by weight or less of the excitation energy transfer component EET-2 based on the total weight of the light-emitting layer B (meaning that the total content of EET-2 in each light-emitting layer B is 3% by weight or less).
[0084] In one embodiment of the present invention, the light-emitting layer B comprises a small FWHM emitter S of 5% by weight or less based on the total weight of the light-emitting layer B. B (In each light-emitting layer B, S B (This means the total content is 5% by weight or less.)
[0085] In a preferred embodiment of the present invention, the light-emitting layer B comprises small FWHM emitters S of 3% by weight or less based on the total weight of the light-emitting layer B. B (In each light-emitting layer B, S B (This means the total content is 3% by weight or less.)
[0086] In one embodiment of the present invention, the light-emitting layer B comprises a small FWHM emitter S of 1% by weight or less based on the total weight of the light-emitting layer B. B (In each light-emitting layer B, S B (The total content is less than 1% by weight.)
[0087] In a preferred embodiment of the present invention, the light-emitting layer B is made up of 15 to 50% by weight of TADF material E based on the total weight of the light-emitting layer B. B (In each light-emitting layer B, E B (This means the total content is in the range of 15-50% by weight.)
[0088] In a preferred embodiment of the present invention, the light-emitting layer B is made up of 20 to 50% by weight of TADF material E based on the total weight of the light-emitting layer B. B (In each light-emitting layer B, E B (This means the total content is in the range of 20-50% by weight.)
[0089] In a preferred embodiment of the present invention, the light-emitting layer B is made up of 20 to 45% by weight of TADF material E based on the total weight of the light-emitting layer B. B (In each light-emitting layer B, E B (This means the total content is in the range of 20-45% by weight.)
[0090] S1-T1 Energy Relationship In the context of the present invention, (i) TADF material E B This is the energy level E(S1 E ) Lowest excited singlet state S1 E , and energy level E(T1 E ) Lowest excited triplet state T1 E It has, (ii) Small Half-width (FWHM) emitter S B This is the energy level E(S1 S ) Lowest excited singlet state S1 S , and energy level E(T1 S ) Lowest excited triplet state T1 S It has, (iii) Host material H B This is the energy level E(S1 H ) Lowest excited singlet state S1 H , and energy level E(T1 H ) Lowest excited triplet state T1 H It has, (iv) The selective energy transfer component EET-2 has an energy level of E(S1 EET-2 ) Lowest excited singlet state S1 EET-2 , and energy level E(T1 EET-2 ) Lowest excited triplet state T1 EET-2 It holds.
[0091] In one embodiment of the present invention, the relationships represented by the following formulas (7) to (9) apply to the material contained in the light-emitting layer B: E(S1 H )>E(S1 E ) (7) E(S1 H )>E(S1 EET-2 ) (8) E(S1 H )>E(S1 S ) (9).
[0092] Therefore, host material H B The lowest excited singlet state S1 H Preferably, TADF material E B The lowest excited singlet state S1 E The lowest excited singlet state S1 of the excitation energy transfer component EET-2 is higher in energy (Equation 7). EET-2 Higher energy (Equation 8), small FWHM emitter S B The lowest excited singlet state S1 S It has higher energy (Equation 9).
[0093] In one embodiment, the aforementioned relationships represented by formulas (7) to (9) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0094] In one embodiment of the present invention, one or both of the relationships represented by the following formulas (10) and (11) apply to the same material contained in the light-emitting layer B: E(S1 E )>E(S1 S ) (10) E(S1 EET-2 )>E(S1 S ) (11).
[0095] Therefore, TADF material E B The lowest excited singlet state S1 E (Equation 10) and / or the lowest excited singlet state S1 of the selective excitation energy transfer component EET-2 EET-2 (Equation 11) preferably represents a small FWHM emitter S B The lowest excited singlet state S1 S More energy It's expensive.
[0096] In one embodiment, one or both of the aforementioned relationships represented by formulas (10) and (11) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0097] In a preferred embodiment of the present invention, the relationships represented by the following formulas (7) to (11) apply to materials contained in the same light-emitting layer B: E(S1 H )>E(S1 E ) (7) E(S1 H )>E(S1 EET-2 ) (8) E(S1 H )>E(S1 S ) (9) E(S1 E )>E(S1 S ) (10) E(S1 EET-2 )>E(S1 S ) (11).
[0098] In one embodiment, the aforementioned relationships represented by formulas (7) to (11) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0099] In a preferred embodiment of the present invention, the relationships represented by the following formulas (13) and (14) apply to the material contained in the light-emitting layer B: E(T1 H )>E(T1 E ) (13) E(T1 E )≧E(T1 EET-2 ) (14).
[0100] Therefore, host material H B The lowest excited triplet state T1 H Preferably, TADF material E B The lowest excited triplet state T1 E Higher energy (Equation 13). Also, TADF material E B The lowest excited triplet state T1 E Preferably, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2 The energy is the same as or higher than (Equation 14).
[0101] In one embodiment, the aforementioned relationship represented by formulas (13) and (14) applies to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0102] In a preferred embodiment of the present invention, the relationships represented by the following formulas (14) to (16) apply to materials contained in the same light-emitting layer B: E(T1 E )≧E(T1 EET-2 ) (14) E(T1 EET-2 )>E(S1 S ) (15) E(T1 EET-2 )>E(T1 S ) (16).
[0103] Therefore, TADF material EB The lowest excited triplet state T1 E Preferably, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2 The lowest excited triplet state T1 of the selective excitation energy transfer component EET-2 has the same energy as or higher than (Equation 14). EET-2 Preferably, a small FWHM emitter S B The lowest excited singlet state S1 S The lowest excited triplet state T1 of the selective excitation energy transfer component EET-2, which has a higher energy (Equation 15). EET-2 Preferably, a small FWHM emitter S B The lowest excited triplet state T1 S It has higher energy (Equation 16).
[0104] In one embodiment, the aforementioned relationships represented by formulas (14) to (16) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0105] In a preferred embodiment of the present invention, the relationships represented by the following formulas (7) to (10) and (15) apply: E(S1 H )>E(S1 E ) (7) E(S1 H )>E(S1 EET-2 ) (8) E(S1 H )>E(S1 S ) (9) E(S1 E )>E(S1 S ) (10) E(T1 EET-2 )>E(S1 S ) (15).
[0106] In one embodiment, the aforementioned relationships represented by formulas (7) to (10) and formula (15) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0107] In an alternative embodiment of the present invention, the relationship represented by the following formulas (17) and (10) applies to the material contained in the light-emitting layer B: E(T1 EET-2 )>E(T1 E ) (17) E(S1 E )>E(S1 S ) (10).
[0108] Therefore, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2 EET-2 is TADF material E B The lowest excited triplet state T1 E The energy is higher than (Equation 17), and TADF material E B The lowest excited singlet state S1 E This is a small FWHM emitter S B The lowest excited singlet state S1 S It has higher energy (Equation 10).
[0109] In an alternative embodiment, the aforementioned relationships represented by formulas (17) and (10) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0110] In a preferred embodiment of the present invention, the relationships represented by the following formulas (18), (15), (19), and (20) apply to the material contained in the light-emitting layer B: E(T1 H )>E(T1 EET-2 ) (18) E(T1 EET-2 )>E(S1 S ) (15) E(T1 H )>E(S1 E ) (19) E(T1 E )>E(T1 EET-2 ) (20).
[0111] Therefore, host material H B The lowest excited triplet state T1 HPreferably, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2 The lowest excited triplet state T1 of the selective excitation energy transfer component EET-2, which has a higher energy (Equation 18). EET-2 Preferably, a small FWHM emitter S B The lowest excited singlet state S1 S The energy is higher (Equation 15), and the host material H B The lowest excited triplet state T1 H Preferably, TADF material E B The lowest excited singlet state S1 E Higher energy (Equation 19), TADF material E B The lowest excited triplet state T1 E Preferably, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2 It has higher energy (Equation 20).
[0112] In one embodiment, the aforementioned relationships represented by formulas (18), (15), (19), and (20) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0113] In one embodiment of the present invention, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2 EET-2 is TADF material E B The lowest excited triplet state T1 E The energy is the same as or higher than, E(T1 EET-2 )≧E(T1 E ) Lowest excited triplet state T1 of selective excitation energy transfer component EET-2 EET-2 and small FWHM emitter S B The lowest excited singlet state S1 S Energy difference E(T1 EET-2 )-E(S1 S ) is less than or equal to 0.3 eV: E(T1 EET-2 )-E(S1 S )≦0.3eV.
[0114] In one embodiment of the present invention, TADF material E B The lowest excited triplet state T1 E This is the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2 The energy is the same as or higher than, E(T1 E )≧E(T1 EET-2 ) TADF material E B The lowest excited triplet state T1 E and small FWHM emitter S B The lowest excited singlet state S1 S Energy difference E(T1 E )-E(S1 S ) is less than or equal to 0.3 eV: E(T1 E )-E(S1 S )≦0.3eV.
[0115] In one embodiment of the present invention, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2 EET-2 is TADF material E B The lowest excited triplet state T1 E The energy is the same as or higher than, E(T1 EET-2 )≧E(T1 E ) Lowest excited triplet state T1 of selective excitation energy transfer component EET-2 EET-2 and small FWHM emitter S B The lowest excited singlet state S1 S Energy difference E(T1 EET-2 )-E(S1 S ) is less than or equal to 0.2 eV: E(T1 EET-2 )-E(S1 S ) ≤ 0.2eV.
[0116] In one embodiment of the present invention, TADF material E B The lowest excited triplet state T1 E This is the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2The energy is the same as or higher than, E(T1 E )≧E(T1 EET-2 ) TADF material E B The lowest excited triplet state T1 E and small FWHM emitter S B The lowest excited singlet state S1 S Energy difference E(T1 E )-E(S1 S ) is less than or equal to 0.2 eV: E(T1 E )-E(S1 S ) ≤ 0.2eV.
[0117] In one embodiment of the present invention, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2 EET-2 is TADF material E B The lowest excited triplet state T1 E The energy is the same as or higher than, E(T1 EET-2 )≧E(T1 E ) Lowest excited triplet state T1 of selective excitation energy transfer component EET-2 EET-2 and small FWHM emitter S B The lowest excited triplet state T1 S Energy difference E(T1 EET-2 )-E(T1 S ) is less than or equal to 0.3 eV: E(T1 EET-2 )-E(T1 S )≦0.3eV.
[0118] In one embodiment of the present invention, TADF material E B The lowest excited triplet state T1 E This is the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2 The energy is the same as or higher than, E(T1 E )≧E(T1 EET-2 ) TADF material E B The lowest excited triplet state T1E and small FWHM emitter S B The lowest excited triplet state T1 S Energy difference E(T1 E )-E(T1 S ) is less than or equal to 0.3 eV: E(T1 E )-E(T1 S )≦0.3eV.
[0119] In one embodiment of the present invention, the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2 EET-2 is TADF material E B The lowest excited triplet state T1 E The energy is the same as or higher than, E(T1 EET-2 )≧E(T1 E ) Lowest excited triplet state T1 of selective excitation energy transfer component EET-2 EET-2 and small FWHM emitter S B The lowest excited triplet state T1 S Energy difference E(T1 EET-2 )-E(T1 S ) is less than or equal to 0.2 eV: E(T1 EET-2 )-E(T1 S ) ≤ 0.2eV.
[0120] In one embodiment of the present invention, TADF material E B The lowest excited triplet state T1 E This is the lowest excited triplet state T1 of the selective excitation energy transfer component EET-2. EET-2 The energy is the same as or higher than, E(T1 E )≧E(T1 EET-2 ) TADF material E B The lowest excited triplet state T1 E and small FWHM emitter S B The lowest excited triplet state T1 S Energy difference E(T1 E )-E(T1 S ) is less than or equal to 0.2 eV: E(T1 E )-E(T1 S ) ≤ 0.2eV.
[0121] HOMO-, LUMO- energy relationship In the context of the present invention, (i) TADF material E B is energy E HOMO (E B ) has the highest occupied orbit HOMO(E B ), and energy E LUMO (E B ) has the lowest airspace orbit LUMO(E B ) has, (ii) Small Half-width (FWHM) emitter S B is energy E HOMO (S B ) has the highest occupied orbit HOMO(S B ), and energy E LUMO (S B ) has the lowest airspace orbit LUMO(S B ) has, (iii) Host material H B is energy E HOMO (H B ) has the highest occupied orbit HOMO(H B ), and energy E LUMO (H B ) has the lowest airspace LUMO(H B ) has, (iv) The selective excitation energy transfer component EET-2 has energy E HOMO The highest occupied orbit HOMO (EET-2) having (EET-2), and energy E LUMO It has a lowest-spaced orbit LUMO (EET-2) with (EET-2).
[0122] In a preferred embodiment, the relationships represented by the following formulas (1) to (3) apply to the material contained in the light-emitting layer B: E LUMO (E B ) <E LUMO (H B ) (1) E LUMO (EB ) <E LUMO (EET-2) (2) E LUMO (E B ) <E LUMO (S B ) (3).
[0123] In a preferred embodiment, the relationships represented by the following formulas (4) to (6) apply to materials contained in the same light-emitting layer B: E HOMO (EET-2)≧E HOMO (H B ) (4) E HOMO (EET-2)≧E HOMO (E B ) (5) E HOMO (EET-2)≧E HOMO (S B ) (6).
[0124] In a preferred embodiment, the relationships represented by the above formulas (1) to (6) apply to the material contained in the light-emitting layer B.
[0125] In one embodiment of the present invention, energy E HOMO (S B ) Small FWHM emitter S B The highest occupied orbital HOMO(S B ) is energy E HOMO (H B ) Host material H B The highest occupied orbit HOMO(H B ) has higher energy: E HOMO (S B )>E HOMO (H B ).
[0126] In one embodiment of the present invention, energy E HOMO (S B ) Small FWHM emitter S B The highest occupied orbital HOMO(S B ) is energy E HOMO (EB ) TADF material E B The highest occupied orbit HOMO(E) B ) has higher energy: E HOMO (S B )>E HOMO (E B ).
[0127] In one embodiment of the present invention, energy E HOMO The highest occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), is energy E HOMO (E B ) TADF material E B The highest occupied orbit HOMO(E) B ) has higher energy: E HOMO (EET-2)>E HOMO (E B ).
[0128] In one embodiment of the present invention, energy E HOMO The highest occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), is energy E HOMO (H B ) Host material H B The highest occupied orbit HOMO(H B ) has higher energy: E HOMO (EET-2)>E HOMO (H B ).
[0129] In one embodiment of the present invention, energy E HOMO The highest occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), is energy E HOMO (S B ) Small FWHM emitter S B The highest occupied orbital HOMO(S B ) has higher energy: E HOMO (EET-2)>E HOMO (SB ).
[0130] In one embodiment of the present invention, TADF material E B The highest occupied orbit HOMO(E) B ) is a small FWHM emitter S B The highest occupied orbital HOMO(S B ) has the same energy as or lower than: E HOMO (E B )≦E HOMO (S B ).
[0131] In one embodiment of the present invention, energy E HOMO The most occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), and energy E HOMO (S B ) Small FWHM emitter S B The highest occupied orbital HOMO(S B The energy difference between ) and is less than 0.3 eV: E HOMO (EET-2)-E HOMO (S B ) < 0.3eV.
[0132] In one embodiment of the present invention, energy E HOMO The most occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), and energy E HOMO (S B ) Small FWHM emitter S B The highest occupied orbital HOMO(S B The energy difference with ) is less than 0.2 eV: E HOMO (EET-2)-E HOMO (S B ) < 0.2eV.
[0133] In one embodiment of the present invention, energy E HOMOThe most occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), and energy E HOMO (S B ) Small FWHM emitter S B The highest occupied orbital HOMO(S B The energy difference between this and ) is greater than 0.0 eV and less than 0.8 eV: 0.0eV <E HOMO (EET-2)-E HOMO (S B ) < 0.8 eV.
[0134] In a preferred embodiment of the present invention, energy E HOMO The most occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), and energy E HOMO (S B ) Small FWHM emitter S B The highest occupied orbital HOMO(S B The energy difference with ) is greater than 0 eV (E HOMO (EET-2)-E HOMO (S B (E) > 0eV, preferably greater than 0.1eV HOMO (EET-2)-E HOMO (S B (E) > 0.1eV, more preferably greater than 0.2eV HOMO (EET-2)-E HOMO (S B ) > 0.2eV), and furthermore, greater than 0.3eV (E HOMO (EET-2)-E HOMO (S B )>0.3eV).
[0135] In a preferred embodiment of the present invention, energy E HOMO The most occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), and energy E HOMO (E B ) TADF material E B The highest occupied orbit HOMO(E) BThe energy difference with ) is greater than 0 eV (E HOMO (EET-2)-E HOMO (E B (E) > 0eV, preferably greater than 0.1eV HOMO (EET-2)-E HOMO (E B (E) > 0.1eV, more preferably greater than 0.2eV HOMO (EET-2)-E HOMO (E B )>0.2eV), more preferably greater than 0.3eV (E HOMO (EET-2)-E HOMO (E B (E) > 0.3eV, more preferably greater than 0.4eV HOMO (EET-2)-E HOMO (E B )>0.4eV), especially greater than 0.5eV (E HOMO (EET-2)-E HOMO (E B )>0.5eV).
[0136] In a preferred embodiment of the present invention, energy E HOMO The most occupied orbital HOMO(EET-2) of the selective excitation energy transfer component EET-2, which has (EET-2), and energy E HOMO (H B ) Host material H B The highest occupied orbit HOMO(H B The energy difference with ) is greater than 0 eV (E HOMO (EET-2)-E HOMO (H B (E) > 0eV, preferably greater than 0.1eV HOMO (EET-2)-E HOMO (H B (E) > 0.1eV, more preferably greater than 0.2eV HOMO (EET-2)-E HOMO (H B )>0.2eV), more preferably greater than 0.3eV (E HOMO (EET-2)-E HOMO (H B(E) > 0.3eV, more preferably greater than 0.4eV HOMO (EET-2)-E HOMO (H B )>0.4eV), especially greater than 0.5eV (E HOMO (EET-2)-E HOMO (H B )>0.5eV).
[0137] In one embodiment of the present invention, energy E LUMO (S B ) Small FWHM emitter S B Lowest altitude orbit LUMO(S B ) and energy E LUMO (E B ) TADF material E B Lowest orbital LUMO(E B The energy difference between this and ) is greater than 0.0 eV and less than 0.3 eV: 0.0eV <E LUMO (S B )-E LUMO (E B ) < 0.3eV.
[0138] In a preferred embodiment of the present invention, energy E LUMO (S B ) Small FWHM emitter S B Lowest altitude orbit LUMO(S B ) and energy E LUMO (E B ) TADF material E B Lowest orbital LUMO(E B The energy difference with ) is greater than 0 eV (E LUMO (S B )-E LUMO (E B (E) > 0eV, preferably greater than 0.1eV LUMO (S B )-E LUMO (E B (E) > 0.1eV, more preferably greater than 0.2eV LUMO (S B )-E LUMO (E B)>0.2eV), particularly preferably greater than 0.3eV (E LUMO (S B )-E LUMO (E B )>0.3eV).
[0139] In a preferred embodiment of the present invention, energy E LUMO The lowest unoccupied orbital LUMO(EET-2) of the selective excitation energy transfer component EET-2, and energy E LUMO (E B ) TADF material E B Lowest orbital LUMO(E B The energy difference with ) is greater than 0 eV (E LUMO (EET-2)-E LUMO (E B (E) > 0eV, preferably greater than 0.1eV LUMO (EET-2)-E LUMO (E B (E) > 0.1eV, more preferably greater than 0.2eV LUMO (EET-2)-E LUMO (E B )>0.2eV), more preferably greater than 0.3eV (E LUMO (EET-2)-E LUMO (E B (E) > 0.3eV, more preferably greater than 0.4eV LUMO (EET-2)-E LUMO (E B )>0.4eV), especially greater than 0.5eV (E LUMO (EET-2)-E LUMO (E B )>0.5eV).
[0140] In a preferred embodiment of the present invention, at least one, preferably each host material H B Energy E LUMO (E B ) has the lowest airspace LUMO(H B ) and energy E LUMO (H B ) Lowest airspace track LUMO (EB The energy difference with ) is greater than 0 eV (E LUMO (H B )-E LUMO (E B (E) > 0eV, preferably greater than 0.1eV LUMO (H B )-E LUMO (E B (E) > 0.1eV, more preferably greater than 0.2eV LUMO (H B )-E LUMO (E B )>0.2eV), more preferably greater than 0.3eV (E LUMO (H B )-E LUMO (E B (E) > 0.3eV, more preferably greater than 0.4eV LUMO (H B )-E LUMO (E B )>0.4eV), especially greater than 0.5eV (E LUMO (H B )-E LUMO (E B )>0.5eV).
[0141] Relationship with maximum emission In one embodiment of the present invention, one or both of the relationships represented by formulas (21) and (22) apply to the material contained in the light-emitting layer B: |E λmax (EET-2)-E λmax (S B )|<0.30eV (21) |E λmax (E B )-E λmax (S B )|<0.30eV (22).
[0142] This means the following: In the luminescent layer B, the maximum luminescence energy E of the selective excitation energy transfer component EET-2 given by electron volts (eV) λmax (EET-2) and a small FWHM emitter S given in electron volts (eV) BMaximum luminous energy E λmax (S B The energy difference with ) is less than 0.30 eV (Equation 21), and / or the TADF material E given in electron volts (eV) B Maximum luminous energy E λmax (E B ) and a small FWHM emitter S given in electron volts (eV) B Maximum luminous energy E λmax (S B The energy difference between ( ) and ( ) is less than 0.30 eV (Equation 22).
[0143] In one embodiment of the present invention, one or both of the aforementioned relationships represented by formulas (21) and (22) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0144] In a preferred embodiment of the present invention, one or both of the relationships represented by formulas (23) and (24) apply to the material contained in the light-emitting layer B: |E λmax (EET-2)-E λmax (S B )|<0.20eV (23) |E λmax (E B )-E λmax (S B )|<0.20eV (24).
[0145] This means the following: In the luminescent layer B, the maximum luminescence energy E of the selective excitation energy transfer component EET-2 given by electron volts (eV) λmax (EET-2) and a small FWHM emitter S given in electron volts (eV) B Maximum luminous energy E λmax (S B The energy difference with ) is less than 0.20 eV (Equation 23), and / or the TADF material E given in electron volts (eV) B Maximum luminous energy E λmax (E B ) and a small FWHM emitter S given in electron volts (eV)B Maximum luminous energy E λmax (S B The energy difference between ( ) and ( ) is less than 0.20 eV (Equation 24).
[0146] In one embodiment of the present invention, one or both of the aforementioned relationships represented by formulas (23) and (24) apply to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0147] In a more preferred embodiment of the present invention, one or both of the relationships represented by formulas (25) and (26) apply to the material contained in the light-emitting layer B: |E λmax (EET-2)-E λmax (S B )|<0.10eV (25) |E λmax (E B )-E λmax (S B )|<0.10eV (26).
[0148] This means the following: In the luminescent layer B, the maximum luminescence energy E of the selective excitation energy transfer component EET-2 given by electron volts (eV) λmax (EET-2) and a small FWHM emitter S given in electron volts (eV) B Maximum luminous energy E λmax (S B The energy difference with ) is less than 0.10 eV (Equation 25), and / or the TADF material E given in electron volts (eV) B Maximum luminous energy E λmax (E B ) and a small FWHM emitter S given in electron volts (eV) B Maximum luminous energy E λmax (S B The energy difference between ( ) and ( ) is less than 0.10 eV (Equation 26).
[0149] In one embodiment of the present invention, the aforementioned relationship represented by formulas (25) and (26) applies to the material contained in the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0150] In one embodiment of the present invention, the relationship represented by formula (27) applies to the material contained in the light-emitting layer B: E λmax (EET-2)>E λmax (S B ) (27).
[0151] This is the maximum emission energy E of the selective excitation energy transfer component EET-2 given by electron volts (eV) within the emissive layer B. λmax (EET-2) is a small FWHM emitter S given in electron volts (eV). B Maximum luminous energy E λmax (S B This means it is greater than ).
[0152] In one embodiment of the present invention, the relationship represented by formula (28) applies to the material contained in the light-emitting layer B: E λmax (E B )>E λmax (S B ) (28).
[0153] This is because, within the light-emitting layer B, the TADF material E is given an electron volt (eV) B Maximum luminous energy E λmax (E B ) is given in electron volts (eV) as a small FWHMS B Maximum luminous energy E λmax (S B This means it is greater than ).
[0154] Element hue and performance A further embodiment of the present invention is 1000 cd / m². 2This relates to an electroluminescent element (e.g., OLED) that exhibits an external quantum efficiency of more than 10%, preferably more than 13%, more preferably more than 15%, even more preferably 18% or more, and even more preferably 20% or more, and that exhibits maximum light emission in the 500nm to 560nm range.
[0155] A further embodiment of the present invention is 1000 cd / m². 2 This relates to an electroluminescent element (e.g., OLED) that exhibits an external quantum efficiency of more than 10%, preferably more than 13%, more preferably more than 15%, even more preferably 18% or more, and even more preferably 20% or more, and that exhibits maximum light emission in the 510nm to 550nm range.
[0156] A further embodiment of the present invention is 1000 cd / m². 2 This relates to an electroluminescent element (e.g., OLED) that exhibits an external quantum efficiency of more than 10%, preferably more than 13%, more preferably more than 15%, even more preferably 18% or more, and even more preferably 20% or more, and that exhibits maximum light emission in the range of 515 nm to 540 nm.
[0157] In a preferred embodiment, the electroluminescent element (e.g., OLED) has a constant current density J0 = 15 mA / cm². 2 In this case, the LT95 value is greater than 100 hours, preferably greater than 200 hours, more preferably greater than 300 hours, even more preferably greater than 400 hours, even more preferably greater than 750 hours, and even more preferably greater than 1000 hours.
[0158] Further embodiments of the present invention relate to an electroluminescent element (e.g., an OLED) that emits light in distinct color points. According to the present invention, the electroluminescent element (e.g., an OLED) emits light in a narrow emission band (small half-width (FWHM)). In a preferred embodiment, the electroluminescent element (e.g., an OLED) according to the present invention emits light having an FWHM of a main emission peak of less than 0.25 eV, preferably less than 0.20 eV, more preferably less than 0.15 eV, and even more preferably less than 0.13 eV. Further embodiments of the present invention relate to an electroluminescent element (e.g., OLED) that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of primary green (CIEx=0.170 and CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (Ultra High Definition) displays, such as UHD-TVs. In this paragraph, the term “close” refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emission elements (with a transparent top electrode) are typically used, while the test elements used throughout the present invention represent bottom-emission elements (with a transparent bottom electrode and substrate). Therefore, a further aspect of the present invention relates to an electroluminescent element (e.g., OLED) whose light emission exhibits CIEx color coordinates of 0.15 to 0.45, preferably 0.15 to 0.35, more preferably 0.15 to 0.30, even more preferably 0.15 to 0.25, and even further, 0.15 to 0.20, and / or CIEy color coordinates of 0.60 to 0.92, preferably 0.65 to 0.90, more preferably 0.70 to 0.88, even more preferably 0.75 to 0.86, and even further, 0.79 to 0.84.
[0159] Further embodiments of the present invention relate to an OLED that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.265) and CIEy (=0.65) color coordinates of primary green (CIEx=0.265 and CIEy=0.65) as defined in DCIP3. In this paragraph, the term “close” refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emission elements (with a transparent top electrode) are typically used, while the test elements used throughout the present invention represent bottom-emission elements (with a transparent bottom electrode and substrate). A further aspect of the present invention relates to an OLED in which the bottom emission exhibits CIEx color coordinates of 0.2 to 0.45, preferably 0.2 to 0.35, more preferably 0.2 to 0.30, even more preferably 0.24 to 0.28, and even more preferably 0.25 to 0.27, and / or CIEy color coordinates of 0.60 to 0.9, preferably 0.6 to 0.8, more preferably 0.60 to 0.70, even more preferably 0.62 to 0.68, and even more preferably 0.64 to 0.66.
[0160] Further embodiments of the present invention relate to an electroluminescent element (e.g., an OLED) that emits light at distinct color points. According to the present invention, the electroluminescent element (e.g., an OLED) emits light having a narrow emission band (small half-width (FWHM)). In a preferred embodiment, the electroluminescent element (e.g., an OLED) according to the present invention emits light having an FWHM of a main emission peak of less than 0.25 eV, preferably less than 0.20 eV, more preferably less than 0.15 eV, and even more preferably less than 0.13 eV.
[0161] One of the objectives of organic electroluminescent devices is the generation of light. Therefore, the present invention also provides any organic electroluminescent device according to the present invention. This relates to a method for generating light in a desired wavelength range, including the step of [doing something].
[0162] Therefore, another aspect of the present invention relates to a method for generating light in a desired wavelength range, comprising the following steps: (i) To provide an organic electroluminescent element according to the present invention, and (ii) Applying an electric current to the organic electroluminescent element.
[0163] Another aspect of the present invention relates to a method for manufacturing an organic electroluminescent element by constructing the aforementioned elements. The present invention also relates to a method for generating green light, in particular by using an organic electroluminescent element.
[0164] Another aspect of the present invention relates to an organic electroluminescent element to which the following formula (29) is applied to a material containing the light-emitting layer B: 510nm ≤ λ max (S B ) ≤ 550nm (29)
[0165] Here, .'' max (S B ) is a small FWHM emitter S B This represents the maximum luminescence, given in nanometers (nm).
[0166] A further aspect of the present invention relates to a method for generating light, comprising the following steps: (i) To provide an organic electroluminescent element according to the present invention, and (ii) Applying an electric current to the organic electroluminescent element.
[0167] A further aspect of the present invention relates to a method for generating light, comprising the following steps: (i) To provide an organic electroluminescent element according to the present invention, and (ii) Applying an electric current to the organic electroluminescent element, Here, the method is for generating light in the wavelength range of 510 nm to 550 nm.
[0168] A further aspect of the present invention relates to a method for generating light, comprising the following steps: (i) To provide an organic electroluminescent element according to the present invention, and (ii) Applying an electric current to the organic electroluminescent element, Here, the method is for generating light in the wavelength range of 515 nm to 540 nm.
[0169] A further aspect of the present invention relates to a method for generating light, comprising the following steps: (i) To provide an organic electroluminescent element according to the present invention, and (ii) Applying an electric current to the organic electroluminescent element, Here, the method described above is for generating light in the wavelength range of 515 nm to 540 nm.
[0170] Those skilled in the art will see that, by their structure, TADF material E B (See below) and the excitation energy transfer component EET-2 (See below) can be used as emitters in organic electroluminescent devices. However, preferably, in the organic electroluminescent device according to the present invention, the TADF material E B The primary function of the excitation energy transfer component EET-2 is not to emit light. In a preferred embodiment, when a voltage (and current) is applied, the organic electroluminescent element according to the present invention emits light, and this light emission is mainly (i.e., more than 50%, preferably more than 60%, more preferably more than 70%, even more preferably more than 80%, and even more than 90%) from the small FWHM emitter S B This is due to fluorescence emitted by the . As a result, the organic electroluminescent element according to the present invention preferably has a voltage of less than 0.25 eV, more preferably, It exhibits narrow emission represented by a small FWHM of a main emission peak with a voltage of less than 0.20 eV, more preferably less than 0.15 eV, and even more preferably less than 0.13 eV.
[0171] In a preferred embodiment of the present invention, the relationship represented by the following formula (32) applies:
number
[0172] For example, two small FWHM emitters S, each having a light-emitting layer B with a concentration of 1% by weight. B If it includes, the spin coating film preferably has two types of small FWHM emitters S B Each is present in 1% by weight. In an exemplary case, the matrix material of the spin-coated film would amount to 98% by weight of the spin-coated film. The matrix material of such a spin-coated film is the host material H contained in the light-emitting layer B of the organic electroluminescent element. B The weight ratio may be selected to reflect the weight ratio. In the example above, the light-emitting layer B is a single host material H B If it includes, the host material may preferably be the sole matrix material of the spin-coated film. However, in the above example, if the light-emitting layer B is made of two types of host material H BIf it contains, one having a content of 60% by weight and the other having a content of 20% by weight (i.e., a ratio of 3:1), then the aforementioned matrix material of the spin coating film (two types of small FWHM emitters S B (Containing 1% by weight of each) preferably two host materials H present in the EML B A 3:1 mixture may also be used.
[0173] When the organic electroluminescent element according to the present invention includes one or more light-emitting layers B, the relationship represented by formula (32) preferably applies to all light-emitting layers B included in the element.
[0174] In one embodiment, the light-emitting layer B of the organic electroluminescent element according to the present invention is the FWHM described above. D :FWHM SB The ratio is 1.50 or less, preferably 1.40 or less, more preferably 1.30, even more preferably 1.20, and even more preferably 1.10.
[0175] In the context of the present invention, small FWHM emitter S B For the selection of fluorescent emitters for use, it should be noted that the FWHM value is determined as described in the subsections below (briefly, preferably from the spin-coated film of each emitter in poly(methyl methacrylate) PMMA having a concentration of 1-5% by weight, particularly 2% by weight, or from the solution, see below). That is, exemplary small FWHM emitters S shown in Table 1S B The FWHM value is given in the context of formula (32) and preferred embodiments related to the present invention. SB It is not understood as a value.
[0176] The examples and claims further illustrate the present invention.
[0177] Host material H B According to the present invention, any one or more host materials H contained in any one or more light-emitting layers B Bp-host H exhibits high hole mobility. P n-host H exhibits high electron mobility N , or bipolar host material H exhibiting both high hole mobility and high electron mobility BP That's fine.
[0178] In the context of the present invention, n-host H exhibiting high electron mobility N Preferably, -2.50 eV or less (E LUMO (H N )≦-2.50eV), comfortable, E LUMO (H N )≦-2.60eV, more preferably E LUMO (H N ) ≤ -2.65eV, more preferably E LUMO (H N LUMO energy E ) ≤ -2.70 eV LUMO (H N ) has. The LUMO is the lowest unsaturated orbit. The energy of the LUMO is determined as described in the subsection below.
[0179] In the context of the present invention, p-host H exhibiting high hole mobility P Preferably, -6.30 eV or higher (E HOMO (H P )≧-6.30eV), comfortably, E HOMO (H P )≧-5.90eV, more preferably E HOMO (HP)≧-5.70eV, more preferably E HOMO (H P HOMO energy E ≥ -5.40 eV HOMO (H P ) has. The HOMO is the highest occupied orbital. The energy of the HOMO is determined as described in the subsections below this text.
[0180] In a preferred embodiment of the present invention, each light-emitting layer B of the organic electroluminescent element according to the present invention contains at least one, preferably each, host material H B is -6.30 eV or higher (EHOMO (H P )≧-6.30eV), preferably E HOMO (H P )≧-5.90eV, comfortably, E HOMO (H P )≧-5.70eV, more preferably E HOMO HOMO energy E (HP) ≥ -5.40 eV HOMO (H P ) possessing p-host H P Therefore, the HOMO is the highest occupied orbit. The energy of the HOMO is determined as described in the subsections below this text.
[0181] In one embodiment of the present invention, within each light-emitting layer B, at least one, preferably each p-host H, is contained in the light-emitting layer B. P This is a HOMO energy E smaller than -5.60 eV. HOMO (H P ) has.
[0182] In the context of the present invention, bipolar host H exhibiting high electron mobility BP Preferably, -2.50 eV or less (E LUMO (H BP )≦-2.50eV), comfortable, E LUMO (H BP )≦-2.60eV, more preferably E LUMO (H BP ) ≤ -2.65eV, more preferably E LUMO (H BP LUMO energy E ) ≤ -2.70 eV LUMO (H BP ) has. The LUMO is the lowest unsaturated orbit. The energy of the LUMO is determined as described in the subsection below.
[0183] In the context of the present invention, bipolar host H exhibiting high hole mobility BP Preferably, -6.30 eV or higher (E HOMO (H BP )≧-6.30eV), comfortably, E HOMO (HBP )≧-5.90eV, more preferably E HOMO (H BP )≧-5.70eV, more preferably E HOMO (H BP HOMO energy E ≥ -5.40 eV HOMO (H BP ) has. The HOMO is the highest occupied orbital. The energy of the HOMO is determined as described in the subsections below this text.
[0184] In one embodiment of the present invention, a bipolar host material H BP Preferably, both poles Sex host material H BP It satisfies all of the following requirements: (i) -2.50eV or less (E LUMO (H BP )≦-2.50eV), preferably E LUMO (H BP ) ≤ -2.60 eV, comfortable, E LUMO (H BP ) ≤ -2.65eV, more preferably E LUMO (H BP LUMO energy E ) ≤ -2.70 eV LUMO (H BP ) has, (ii) -6.30eV or more (E HOMO (H BP )≧-6.30eV), preferably E HOMO (H BP )≧-5.90eV, comfortably, E HOMO (H BP )≧-5.70eV, more preferably E HOMO (H BP HOMO energy E ≥ -5.40 eV HOMO (H BP ) has.
[0185] Those skilled in the art will know what materials are suitable host materials for use in the organic electroluminescent elements according to the present invention. See the following examples: Y.Tao, C.Yang, J.Quin, Chemical Society Reviews 2011, 40, 2943, DOI: 10.1039 / C0CS00160K; KSYook, JYLee, 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.
[0186] Also, for example, US2006006365(A1), US2006208221(A1), US2005069729(A1), EP1205527(A1), US2009302752(A1), US20090134784(A1), US2009302742(A1), US2010187977(A 1), US2010187977(A1), US2012068170(A1), US2012097899(A1), US2006121308(A1) ), US2006121308(A1), US2009167166(A1), US2007176147(A1), US2015322091(A1) 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 usable in organic electroluminescent elements according to the present invention. This is understood not to mean that the present invention is limited to organic electroluminescent elements comprising host materials disclosed in the cited reference documents. Furthermore, any host material used in the latest technology may be a suitable host material H in the context of the present invention. B It is understood that this is the case.
[0187] In a preferred embodiment of the present invention, each light-emitting layer B of the organic electroluminescent element according to the present invention comprises one or more p-host H P Includes. In one embodiment of the present invention, each light-emitting layer B of the organic electroluminescent element according to the present invention is a single host material H B It contains only, and the host material is p-host H P That is the case.
[0188] In one embodiment of the present invention, each light-emitting layer B of the organic electroluminescent element according to the present invention comprises one or more n-host H N This includes. In other embodiments of the present invention, each light-emitting layer B of the organic electroluminescent element according to the present invention is a single host material. H B It contains only n-host H N That is the case.
[0189] In one embodiment of the present invention, each light-emitting layer B of the organic electroluminescent element according to the present invention comprises one or more bipolar host H BP Includes. In one embodiment of the present invention, each light-emitting layer B of the organic electroluminescent element according to the present invention is a single host material H B It contains only, and the host material is bipolar host H BP That is the case.
[0190] In another embodiment of the present invention, at least one light-emitting layer B of the organic electroluminescent element according to the present invention comprises at least two different host materials H B This includes one or more host materials H present in each light-emitting layer B. B These are all p-host H P Either they are n-host H N Either they are bipolar host H BP However, combinations of these are also acceptable.
[0191] If the organic electroluminescent element according to the present invention includes one or more light-emitting layers B, then any one of them is independent of the other one or more light-emitting layers B and is made of one or more host materials H to which the above definition applies. B It is understood that this includes [the specified material]. Furthermore, it is understood that the different light-emitting layers B contained in the organic electroluminescent element according to the present invention are not necessarily all made of the same material, nor do they necessarily contain the same material in the same concentration or proportion.
[0192] When the light-emitting layer B of the organic electroluminescent element according to the present invention is composed of one or more sublayers, any of these sublayers may be independent of the other one or more sublayers and may be one or more host materials H to which the above definition applies. B It is understood that this includes [the specified material]. Furthermore, it is understood that the different sublayers of the light-emitting layer B contained in the organic electroluminescent element according to the present invention are not necessarily all made of the same material, nor do they necessarily contain the same material in the same concentration or proportion.
[0193] When included in the same light-emitting layer B of the organic electroluminescent element according to the present invention, at least one p-host H P and at least one n-host H N H can selectively form excyplexes. Those skilled in the art will know that H can form excyplexes. P and H N A method for selecting a pair of H P and H N The selection criteria, including the HOMO- and / or LUMO-energy level requirements, are known. That is, if excyplex formation is required, the p-host material H P The highest occupied orbital (HOMO) is in the n-host material H N The energy of the HOMO is at least 0.20 eV higher, and the p-host material H P The lowest unoccupied orbital (LUMO) is the n-host material H N Its energy is at least 0.20 eV higher than the LUMO.
[0194] In a preferred embodiment of the present invention, at least one host material H B (For example, H P H N and / or H BP ) is an organic host material, which in the context of the present invention means that it does not contain any transition metals. In a preferred embodiment of the present invention, all host materials H of the electroluminescent element of the present invention B (H P H N and / or HBP ) are organic host materials, which in the context of the present invention means that they do not contain any transition metals. Preferably, at least one host material H B , more preferably, all host material H B (H P H N and / or H BP ) is mainly composed of hydrogen (H), carbon (C), and nitrogen (N), but may also contain, for example, oxygen (O), boron (B), silicon (Si), fluorine (F), and bromine (Br).
[0195] In one embodiment of the present invention, each host material H B p-host H P That is the case.
[0196] In one embodiment of the organic electroluminescent element according to the present invention, at least one, preferably each light-emitting layer B, each host material H B p-host H P That is the case.
[0197] In a preferred embodiment of the present invention, p-host H is selectively included in any at least one light-emitting layer B (which consists of one (lower) layer or includes one or more sublayers) as a whole. P This includes, or consists of:
[0198] Chemical formula H P -I, H P -II, H P -III, H P -IV, H P -V, H P -VI, H P -VII, H P -VIII, H P -IX and H P - A first chemical substructure that includes or is composed of any one of X, and [ka] ··· Chemical formula H P -I
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
Chem.
[0199] Each is Chemical formula H P -XI, H P -XII, H P -XIII, H P -XIV, H P -XV, HP -XVI, H P -XVII, H P -XVIII and H P -Containing a structure by any one of -XIX, or one or more second chemical substructures composed thereof,
Chemical formula
Chemical formula
Chemical formula
Chemical formula
[0201] In a more preferred embodiment of the present invention, Z 1 In each case, the bond is direct, and the adjacent substituent R II They do not bond to form an additional ring system.
[0202] In a more preferred embodiment of the present invention, p-host H is selectively included in the organic electroluminescent element according to the present invention. P The following group is selected from the structures listed below: [ka] [ka] [ka] [ka] [ka] [ka]
[0203] In a preferred embodiment of the present invention, n-host H is selectively included in any one or more light-emitting layers B (which consist of one (sub) layer or include one or more sub) as a whole.N is composed of or contains a structure formed by any one of chemical formulas H N -I, H N -II, and H N -III: [Chemical formula] ··· Chemical formula H N -I [Chemical formula] ··· Chemical formula H N -II [Chemical formula] ··· Chemical formula H N -III
[0204] Here, R III and R IV are each independently selected from the group consisting of, in each case, one or more substituents selectively substituted with substituents independently selected from the group consisting of hydrogen, deuterium, Me, hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, Me, i Pr, t Bu, and Ph selectively substituted with one or more substituents independently selected from the group consisting of Ph and chemical formula H N -IV, H N -V, H N -VI, H N -VII, H N -VIII, H N -IX, H N -X, H N -XI, H N -XII, H N -XIII, and H N -XIV, represented by any one of: [Chemical formula] ··· Chemical formula H N -IV [Chemical formula] ...Chemical formula H N -V [ka] ...Chemical formula H N -VI [ka] ...Chemical formula H N -VII [ka] ...Chemical formula H N -VIII [ka] ...Chemical formula H N -IX [ka] ...Chemical formula H N -X [ka] ...Chemical formula H N -XI [ka] ...Chemical formula H N -XII [ka] ...Chemical formula H N -XIII [ka] ...Chemical formula H N -XIV Here, The dotted line represents the chemical formula H N -IV, H N -V, H N -VI, H N -VII, HN -VIII, H N -IX, HN-X, H N -XI, H N -XII, H N -XIII and H N - A structure consisting of any one of XIV is H N -I, H N -II and H N -III indicates the bonding position of the single bond that connects to the structure, X 1 These are oxygen (O), sulfur (S), or C(R). V )2, R V In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, and Me, i Pr, t Ph is selectively substituted with one or more substituents independently selected from the group consisting of Bu and Ph. Here, two or more adjacent substituents R V It selectively forms monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, and has the chemical formula H N -IV, H N -V, H N -VI, H N -VII, H N -VIII, H N -IX, H N -X, H N -XI, H N -XII, H N -XIII and H N - Not only structures consisting of any one of XIV, but also adjacent substituents R V The fused ring system, composed of additional rings selectively formed by this process, contains a total of 8 to 60 carbon atoms, preferably 12 to 40 carbon atoms, more preferably 14 to 32 carbon atoms. Here, the chemical formula H N -I and H N -II has at least one substituent R IIIis CN.
[0205] In a more preferred embodiment of the present invention, n-host H is selectively included in the organic electroluminescent element according to the present invention. N The following group is selected from the structures listed below: [ka] [ka] [ka]
[0206] In one embodiment of the present invention, n-host H included in any light-emitting layer B of the organic electroluminescent element according to the present invention N It does not contain any phosphine oxide groups, and in particular, n-host H N It is not bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO).
[0207] Excitation energy transfer component EET-2 A small FWHM emitter S is included in the same light-emitting layer B of the organic electroluminescent element according to the present invention. B To transfer excitation energy to the TADF material E B And a selective excitation energy transfer component EET-2 is preferably selected.
[0208] To enable such energy transfer, preferably, the emission spectrum at room temperature (i.e., (about) 20°C) (e.g., TADF material E) B (Fluorescence spectrum of E) and B The small FWHM emitter S must transfer energy. B There is spectral superposition between the absorption spectrum at room temperature (i.e., approximately 20°C). Therefore, in a preferred embodiment, within the light-emitting layer B, the TADF material EB The emission spectrum at room temperature (i.e., (approximately) 20°C) and the small FWHM emitter S B There is spectral superposition between the absorption spectrum and the emission spectrum. The absorption and emission spectra are recorded as described in the subsections later in the text.
[0209] In a preferred embodiment of the present invention, within the light-emitting layer B, the selective excitation energy transfer component EET-2 reduces the excitation energy of the FWHM emitter S B Move it.
[0210] To enable such energy transfer, preferably, the emission spectrum of the selectively excited energy transfer component EET-2 at room temperature (i.e., about 20°C) (for example, EET-2 is TADF material E B In this case, the fluorescence spectrum and EET-2 are phosphorescent material P B In this case, the phosphorescence spectrum (described later) and the small FWHM emitter S that EET-2 must transfer energy from B There is spectral superposition between the absorption spectrum of the small FWHM emitter S at room temperature (i.e., approximately 20°C) and the emission spectrum of the small FWHM emitter S in the light-emitting layer B. B There is spectral superposition between the absorption spectrum at room temperature (i.e., approximately 20°C). The absorption and emission spectra are recorded as described in the subsections later in the text.
[0211] In a more preferred embodiment of the present invention, within the light-emitting layer B, not only the selective excitation energy transfer component EET-2 contained in the light-emitting layer B, but also the TADF material E B This is a small FWHM emitter S B Transfer energy to it.
[0212] In a preferred embodiment of the present invention, the following two conditions are met within the light-emitting layer B: (i) TADF material E BThe emission spectrum at room temperature (i.e., (approximately) 20°C) and the small FWHM emitter S B There is spectral superposition between the absorption spectrum at room temperature (i.e., approximately 20°C) and the other spectrum. (ii) Emission spectrum of the selective excitation energy transfer component EET-2 at room temperature (i.e., approximately 20°C) and small FWHM emitter S B There is spectral superposition between the absorption spectrum at room temperature (i.e., approximately 20°C) and the other spectrum.
[0213] Here, the absorption and emission spectra are recorded as described in the subsections later in the text.
[0214] In a preferred embodiment, the light-emitting layer B and the TADF material E B Lowest orbital LUMO(E B ) is an energy E less than -2.3 eV LUMO (E B ) has: E LUMO (E B ) <-2.3eV.
[0215] In a preferred embodiment, the light-emitting layer B and the TADF material E B Lowest orbital LUMO(E B ) is an energy E less than -2.6 eV LUMO (E B ) has: E LUMO (E B ) <-2.6eV.
[0216] In a preferred embodiment, within the light-emitting layer B, TADF material E B The highest occupied orbit HOMO(E) B ) has an energy E greater than -6.3 eV HOMO (E B ) has: E HOMO (E B )>-6.3eV.
[0217] In a preferred embodiment, the following two conditions are met within the light-emitting layer B: (i) TADF material E BLowest orbital LUMO(E B ) is an energy E less than -2.6 eV LUMO (E B ) has: E LUMO (E B ) <-2.6eV, and (ii) TADF material E B The highest occupied orbit HOMO(E) B ) has an energy E greater than -6.3 eV HOMO (E B ) has: E HOMO (E B )>-6.3eV.
[0218] In one embodiment of the present invention, within the light-emitting layer B, the selective excitation energy transfer component EET-2 satisfies at least one, preferably exactly one, of the following two conditions: (i) 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, and even more preferably less than 0.05 eV, E(S1 EET-2 ) and E(T1 EET-2 ΔE corresponds to the energy difference with ) ST Shows a value and / or (ii) containing at least one, preferably exactly one, transition metal with a standard atomic weight greater than 40 (meaning that at least one atom in EET-2 is a (transition) metal with an atomic weight greater than 40, where the transition metal may be in any oxidation state).
[0219] In a preferred embodiment, within the light-emitting layer B, TADF material E B The lowest excited singlet state energy level E(S1) is 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, and even more preferably less than 0.05 eV. E ) and the lowest excited triplet state energy level E(T1 E ΔE corresponding to the energy difference with ) ST Show the value.
[0220] In a preferred embodiment, within the light-emitting layer B, the selective excitation energy transfer component EET-2 comprises at least one, preferably exactly one, transition metal with a standard atomic weight greater than 40 (i.e., EET-2 is a (transition) metal having an atomic weight greater than 40, where the transition metal may be in any oxidation state).
[0221] In a preferred embodiment of the present invention, the following two conditions are met within each light-emitting layer B: (i) TADF material E B The lowest excited singlet state energy level E(S1) is 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, and even more preferably less than 0.05 eV. E ) and the lowest excited triplet state energy level E(T1 E ΔE corresponding to the energy difference with ) ST Show the value, and (ii) The selective excitation energy transfer component EET-2 comprises at least one, preferably exactly one, transition metal with a standard atomic weight greater than 40 (i.e., EET-2 is a (transition) metal having an atomic weight greater than 40, where the transition metal may be in any oxidation state).
[0222] In a preferred embodiment of the present invention, in the light-emitting layer B, the selective excitation energy transfer component EET-2 satisfies at least one, preferably exactly one, of the following two conditions: (i) 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, and even more preferably less than 0.05 eV, E(S1 EET-2 ) and E(T1 EET-2 ΔE corresponds to the energy difference with ) ST The values are shown (see below), and / or (ii) Containing iridium (Ir), palladium (Pd), or platinum (Pt) (meaning that at least one atom in EET-2 is iridium (Ir), palladium (Pd), or platinum (Pt), where Ir, Pd, and Pt may be in any oxidation state, see below).
[0223] In a preferred embodiment, at least one, preferably within each light-emitting layer B, at least one, preferably each selective excitation energy transfer component EET-2, comprises iridium (Ir) or platinum (Pt) (meaning that at least one atom of each EET-2 is iridium (Ir) or platinum (Pt), where Ir and Pt may be in any oxidation state, see below).
[0224] As described above, in the context of the present invention, the light-emitting layer B is TADF material E B and a selective excitation energy transfer component EET-2, where they are not identical (i.e., they do not have the same chemical formula). This is the TADF material E within each light-emitting layer B of the organic electroluminescent element according to the present invention. B And the excitation energy transfer component EET-2, for example, independently of each other, TADF material E B This means that it is possible to select from a group consisting of, but the chemical structures are not identical in any case. That is, within the light-emitting layer B, E B It does not have the same chemical formula (or structure) as EET-2.
[0225] In a particularly preferred embodiment, the selective excitation energy transfer component EET-2 selectively included in the organic electroluminescent element according to the present invention is a phosphorescent material P as defined herein. B That is the case.
[0226] In a particularly preferred embodiment, the selective excitation energy transfer component EET-2 selectively included in the organic electroluminescent element according to the present invention is a TADF material E as defined herein. BThis is a TADF material that can have structural properties as defined for [the specified value].
[0227] If the excitation energy transfer component is selected to be a TADF material, then TADF material E B It should be understood that any preferred features, characteristics, and examples described later are also applicable to the selective excitation energy transfer component EET-2.
[0228] Furthermore, the excitation energy transfer component is phosphorescent material P B If selected as such, phosphorescent material P B It should be understood that any preferred features, characteristics, and examples described later are also applicable to the selective excitation energy transfer component EET-2.
[0229] TADF material E B As is known to those skilled in the art, for example, in an organic light-emitting diode (OLED), the light emitted from the emitter material (i.e., the light-emitting dopant) includes fluorescence from an excited singlet state (generally the lowest excited singlet state S1) and phosphorescence from an excited triplet state (generally the lowest excited triplet state T1).
[0230] In the context of the present invention, a fluorescent emitter can emit light upon electronic excitation at room temperature (i.e., about 20°C) (for example, in an organic electroluminescent device), where the luminescent excited state is a singlet state (generally, the lowest excited singlet state S1). A fluorescent emitter generally exhibits immediate (i.e., direct) fluorescence on a nanosecond timescale when the initial electronic excitation (e.g., by electron-hole recombination) provides the excited singlet state of the emitter.
[0231] In the context of the present invention, a delayed fluorescence material is a material that can reach an excited singlet state (generally the lowest excited singlet state S1) from an excited triplet state (generally the lowest excited singlet state S1) via reverse intersystem crossing (RISC; i.e., up-system crossing or reverse intersystem crossing), and can emit light when returning from the excited singlet state (generally S1) to the electronic ground state. The timescale (generally in the microsecond range) at which fluorescence emission occurs after RISC from the excited triplet state (generally T1) to the excited singlet state (generally S1) is slower than the timescale (generally in the nanosecond range) at which direct (i.e., immediate) fluorescence occurs, and is therefore called delayed fluorescence (DF). When RISC from the excited triplet state (generally from T1) to the excited singlet state (generally up to S1) occurs via thermal activation, and the thus filled excited singlet state emits light (delayed fluorescence emission), the process is called thermally activated delayed fluorescence (TADF). Therefore, TADF material is a material that can emit TADF as described above. The energy difference ΔE between the lowest excited singlet state energy level E(S1) and the lowest excited triplet state energy level E(T1) of the fluorescent emitter. ST When ΔE decreases, the transition from the lowest excited triplet state to the lowest excited singlet state by RISC can occur with high efficiency. Therefore, TADF materials generally have a small ΔE. ST Having a value constitutes part of the general knowledge of those skilled in the art (see below).
[0232] The generation of (thermally activated) delayed fluorescence is analyzed, for example, based on decay curves obtained from time-resolved (i.e., transient) photoluminescence (PL) measurements. PL emission from TADF materials can be divided into two components: one from the excited singlet state (generally S1) generated by initial excitation, and another from the excited singlet state (generally S1) generated via RISC through the excited triplet state (generally T1). Generally, there is a considerable time difference between the emission from the excited singlet state (generally S1) formed by initial excitation and the emission from the excited singlet state (generally S1) reached via RISC from the excited triplet state (generally T1).
[0233] TADF materials are preferably related to full decay dynamics and satisfy the following two conditions: (i) Damping dynamics exhibit two time domains, one generally in the nanosecond (ns) range and the other generally in the microsecond (μs) range, and (ii) The morphology of the emission spectrum is identical in the two time domains.
[0234] Here, some of the light emitted in the first decay region is considered immediate fluorescence, and in the second decay region... Some of the light emitted in the region is considered delayed fluorescence. PL measurements can be performed using a spin-coated film of 1–10 wt%, particularly 10 wt%, of each emitter (i.e., assumed TADF material) in poly(methyl methacrylate) (PMMA).
[0235] To assess whether the preferred criterion (i) is met (i.e., the damping dynamics exhibit two time domains, one generally in the nanosecond (ns) range and the other generally in the microsecond (μs) range), TCSPC (Time-correlated single-photon counting) is commonly used (see below), and the overall damping dynamics are generally analyzed as described later. Alternatively, transient photoluminescence measurements using spectral resolution can be performed (see below).
[0236] To assess whether the preferred criterion (ii) is met (i.e., the morphology of the emission spectrum matches in two time domains), transient photoluminescence measurements using spectral resolution can commonly be performed (see below).
[0237] Experimental details regarding such measurements are provided in a subsection later in the text.
[0238] The ratio of delayed fluorescence to immediate fluorescence (n-value) can be calculated by integrating the respective photoluminescence decay over time, as described in the subsections later in this text.
[0239] In the context of the present invention, the TADF material preferably exhibits an n value (i.e., the ratio of delayed fluorescence to immediate fluorescence) greater than 0.05 (n>0.05), more preferably greater than 0.15 (n>0.15), more preferably greater than 0.25 (n>0.25), more preferably greater than 0.35 (n>0.35), more preferably greater than 0.45 (n>0.45), more preferably greater than 0.55 (n>0.55), more preferably greater than 0.65 (n>0.65), more preferably greater than 0.75 (n>0.75), more preferably greater than 0.85 (n>0.85), and even more preferably greater than 0.95 (n>0.95).
[0240] According to the present invention, a thermally activated delayed fluorescence (TADF) material E B The lowest excited singlet state energy level E(S1) is 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, and even more preferably less than 0.05 eV. E ) and the lowest excited triplet state energy level E(T1 E ΔE corresponds to the energy difference with ) ST It is characterized by showing a value. Therefore, the TADF material E according to the present invention B ΔE ST This is the lowest excited triplet state T1 at room temperature (RT, i.e., (approximately) 20°C). E From the lowest excited singlet state S1 E It is small enough to allow thermal repopulation (also known as up-term crossing or reverse-term crossing, or RISC).
[0241] Preferably, in the context of the present invention, TADF material E B (Immediate fluorescence and (luminescence S1) E The status is T1 E Both exhibit delayed fluorescence (when accessed from the state via thermally activated RISC).
[0242] A small FWHM emitter S contained in the light-emitting layer B of the organic electroluminescent element according to the present invention B This is a selective ΔE less than 0.4eV. ST It is understood that it can have a value and exhibit thermally activated delayed fluorescence (TADF). However, in the context of the present invention, any small FWHM emitter S B In contrast, this is merely a selective feature.
[0243] In a preferred embodiment of the present invention, at least one TADF material E B The emission spectrum of and at least one small FWHM emitter S B There is spectral superposition between the absorption spectra of (when both spectra are measured under similar conditions). In this case, the TADF material E B This is at least one small FWHM emitter S B It can transfer energy to it.
[0244] According to the present invention, TADF material E B It has maximum emission in the green wavelength range of 500 nm to 545 nm, preferably 510 nm to 535 nm, and generally, 10 wt% of TADF material E in poly(methyl methacrylate) PMMA at room temperature (i.e., (approximately) 20°C). B Measurements are taken from spin-coated films.
[0245] In a preferred embodiment of the present invention, TADF material E B The maximum emission (peak emission) of the small FWHM emitter S is defined in the context of the present invention. B It is at a wavelength shorter than the maximum emission (peak emission).
[0246] In a preferred embodiment of the present invention, each TADF material E B This is an organic TADF material, which in the context of the present invention means that it does not contain any transition metals. Preferably, each TADF material E according to the present invention BIt is mainly composed of hydrogen (H), carbon (C), and nitrogen (N), but may also contain, for example, oxygen (O), boron (B), silicon (Si), fluorine (F), and bromine (Br).
[0247] In a preferred embodiment of the present invention, each TADF material E B It has a molecular weight of 800 g / mol or less.
[0248] In one embodiment of the present invention, TADF emitter E B Generally, 10 wt% TADF material E in poly(methyl methacrylate) PMMA at room temperature (i.e., (approximately) 20°C) B It exhibits a photoluminescence quantum yield (PLQY) of over 30%, as measured from spin-coated films.
[0249] In a preferred embodiment of the present invention, TADF emitter E B Generally, 10 wt% TADF material E in poly(methyl methacrylate) PMMA at room temperature (i.e., (approximately) 20°C) B It exhibits a photoluminescence quantum yield (PLQY) of over 50%, as measured from spin-coated films.
[0250] In a more preferred embodiment of the present invention, TADF emitter E B Generally, 10 wt% TADF material E in poly(methyl methacrylate) PMMA at room temperature (i.e., (approximately) 20°C) B It exhibits a photoluminescence quantum yield (PLQY) of over 70%, as measured from spin-coated films.
[0251] In one embodiment of the present invention, TADF material E B teeth, (i) Lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ΔE corresponds to the energy difference with ) ST It is characterized by a value of less than 0.4eV, (ii) Exhibits a photoluminescence quantum yield (PLQY) greater than 30%.
[0252] In one embodiment of the present invention, each TADF material E B Lowest orbital LUMO(E B Energy E LUMO (E B ) is less than -2.6eV.
[0253] Generally, it is possible to emit fluorescence and (thermally activated) delayed fluorescence, but the TADF material E included in the organic electroluminescent element of the present invention B It should be noted that, preferably, it primarily functions as an "energy pump" and does not function as an emitter material. That is, the phosphorescent material P contained in the light-emitting layer B B This mainly involves small FWHM emitters S with excitation energies of 1 or more. B They are moved to the main emitter material, which then takes on the role of the main emitter material. Phosphorescent material P in the light-emitting layer B B It is preferable that its primary function is not to emit light. However, it can emit light to some extent.
[0254] Those skilled in the art will know the TADF material (molecule) E according to the present invention. B The method for designing it and the typical structural characteristics of the molecule are known. Simply put, to facilitate reverse intersystem crossing (RISC), ΔE ST Generally decreases, and in the context of the present invention, ΔE ST As mentioned above, this is less than 0.4 eV. This is because the TADF molecule E is used to frequently separate the HOMO and LUMO spatially by the (electron) donor group and (electron) acceptor group, respectively. BThis is achieved by designing the group to be large in volume or twisted via spirojunctions, which reduces the spatial overlap of the HOMO and LUMO. However, minimizing the spatial overlap of the HOMO and LUMO has the disadvantage of also lowering the PLQY (Photoluminescence Quantum Yield) of the TADF material. Therefore, both of these effects must be considered in practice, and ΔE ST Reduce and achieve high PLQY.
[0255] One common approach to designing TADF materials is to covalently bond one or more (electron) donor substructures with distributed HOMOs and one or more (electron) acceptor substructures with distributed LUMOs to the same bridge, which is referred to in this application as a linker group. B For example, it includes two or three linker groups bonded to the same acceptor substructure, and further donor and acceptor substructures may be bonded to each of those two or three linker groups.
[0256] Furthermore, one or more donor substructures and one or more acceptor substructures can be directly bonded to each other (without the presence of a linker group).
[0257] Typical donor substructures include diphenylamine, carbazole, acridine, phenoxazine, and derivatives of related structures.
[0258] Benzene, biphenyl groups, and derivatives of terphenyl groups to a certain extent are common linker groups.
[0259] Nitrile groups are very common acceptor substructures in TADF molecules, and well-known examples include: (i) Carbazolyl dicyanobenzene compounds such as 2CzPN (4,5-di(9H-carbazole-9-yl)phthalonitrile), DCzIPN (4,6-di(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, (ii) Carbazolylcyanopyridine compounds such as 4CzCNPy(2,3,5,6-tetra(9H-carbazole-9-yl)-4-cyanopyridine) and its derivatives, (iii) Carbazolylcyanobiphenyl compounds such as CNBPCz (4,4',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2'-dicarbonitrile), CzBPCN (4,4',6,6'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-3,3'-dicarbonitrile), DDCzIPN (3,3',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2',6,6'-tetracarbonitrile) and their derivatives, Here, in these materials, one or more nitrile groups can be replaced with fluorine (F) or trifluoromethyl (CF3) as acceptor substructures.
[0260] Furthermore, nitrogen heterocycles such as triazines, pyrimidines, triazoles, oxadiazoles, thiadiazoles, heptadine, 1,4-diazatriphenylene, benzothiazoles, benzoxazoles, quinoxalines, and diazafluorene derivatives are well-known acceptor substructures used in the composition of TADF molecules. For example, known examples of TADF molecules containing a triazine acceptor include PIC-TRZ(7,7'-(6-([1,1'-biphenyl]-4-yl)-1,3,5-triazine-2,4-diyl)bis(5-phenyl-5,7-dihydroindoro[2,3-b]carbazole)), mBFCzTrz(5-(3-(4,6-diphenyl-1,3,5-triazine-2-yl))phenyl)-5H-benzofl[3,2-c]carbazole), and DCzTrz(9,9'-(5-(4,6-diphenyl-1,3,5-triazine-2-yl)-1,3-phenylene)bis(9H-carbazole)).
[0261] Another group of TADF materials includes diaryl ketones such as benzophenone, or (heteroaryl)aryl ketones and their derivatives such as 4-benzoylpyridine, 9,10-anthraquinone, and 9H-xanthene-9-one, as acceptor substructures to which donor substructures (mainly carbazolyl substituents) are attached. Examples of such TADF molecules include BPBCz (bis(4-(9'-phenyl-9H,9'H-[3,3'-bicarbazole]-9-yl)phenyl)methanone), mDCBP ((3,5-di(9H-carbazole-9-yl)phenyl)(pyridine-4-yl)methanone), 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-xanthene-9-one), respectively.
[0262] Furthermore, sulfoxides, particularly diphenyl sulfoxides, are commonly used as acceptor substructures for the composition of TADF materials. Well-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-xanthene-9-one 10,10-dioxide).
[0263] The specific material meets the aforementioned basic requirements, namely ΔE ST Considering that the value is less than 0.4 eV, exemplarily, all of the aforementioned groups of TADF molecules are suitable TADF material E for use in the present invention. B We can provide this.
[0264] Those skilled in the art will see that, in addition to the aforementioned named structure, a greater number of materials are suitable TADF material E in the context of the present invention. B It is known that this is the case. Those skilled in the art are familiar with the design principles of such molecules and also know how to design such molecules having a specific emission hue (e.g., blue, green, or red emission).
[0265] Other contributions include: H. Tanaka, K. Shizu, H. Nakanotani, C. Adachi, Chemistry of Materials 2013, 25(18), 3766, DOI: 10.1021 / cm402428a; Advanced Materials 2013, 25(24), 3319, Advanced Materials 2013, 25(24), 3319; K.Nasu, T.Nakagawa, H.Nomura, C.-J.Lin, C.-H.Cheng, M.-R.Tseng, T.Yasudad, C.Adachi, Chemical Communications 2013, 49(88), 10385, DOI:10 .1039 / c3cc44179b; Nature Photonics 2014, 8(4), 326, DOI: 10.1038 / nphoton.2014.12; B.Wex, BRKafarani, Journal of Materials Chemistry C 2017, 5, 2017-01-20. 8622, DOI: 10.1039 / c7tc02156a; Chemistry of Materials 2017, 29(5), 1946, DOI: 10.1021 / acs.chemmater.6b05324; 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 25(22), 5623, DOI: 10.1002 / chem.201805952.
[0266] Furthermore, for example, US2015105564(A1), US2015048338(A1), US2015141642(A1), US2014336379(A1), US2014138670(A1), US2012241732(A1), EP3315581(A1), EP3483156(A1), and US2018053901(A1) are TADF materials E that can be used in organic electroluminescent elements according to the present invention. B This is disclosed. It is understood that this does not mean that the present invention is limited to organic electroluminescent elements comprising TADF materials disclosed in the cited references. Any TADF material used in the latest technology may be a suitable TADF material in the context of the present invention. B It is understood that this is the case.
[0267] In one embodiment of the present invention, each TADF material E B It comprises one or more chemical substructures independently selected from the group consisting of CN, CF3, and selectively substituted 1,3,5-triazinyl groups.
[0268] In one embodiment of the present invention, each TADF material E B It comprises one or more chemical substructures independently selected from the group consisting of CN and selectively substituted 1,3,5-triazinyl groups.
[0269] In one embodiment of the present invention, each TADF material E B It contains one or more selectively substituted 1,3,5-triazinyl groups.
[0270] In one embodiment of the present invention, each TADF material E BIt comprises one or more chemical substructures independently selected from amino groups, indolyls, carbazolyls, and their derivatives, each of which is selectively substituted, where these groups are bonded to the core structure of each TADF molecule via a nitrogen (N) or carbon (C) atom, and the substituents bonded to these groups can form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems.
[0271] In a preferred embodiment of the present invention, at least one, preferably each, TADF material E B This includes: - Amino groups, indolyls, carbazolyls, and their derivatives are independently selected from each other, and each is selectively substituted, where these groups are bonded to the core structure of the respective TADF molecule via a nitrogen (N) or carbon (C) atom. The substituents may form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, one or more first chemical substructures, and One or more second chemical substructures independently selected from the group consisting of -CN, CF3, and selectively substituted 1,3,5-triazinyl groups.
[0272] In a more preferred embodiment of the present invention, at least one, preferably each, TADF material E B This includes: - One or more first chemical substructures, independently selected from amino groups, indolyls, carbazolyls and their derivatives, each selectively substituted, where the groups are bonded to the core structure of the respective TADF molecule via a nitrogen (N) or carbon (C) atom, and the substituents bonded to these groups can form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, and One or more second chemical substructures independently selected from the group consisting of -CN, CF3, and selectively substituted 1,3,5-triazinyl groups.
[0273] In a more preferred embodiment of the present invention, at least one, preferably each, TADF material E B This includes: - One or more first chemical substructures, independently selected from amino groups, indolyls, carbazolyls and their derivatives, each selectively substituted, where the groups are bonded to the core structure of the respective TADF molecule via a nitrogen (N) or carbon (C) atom, and the substituents bonded to these groups can form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, and -1 or more selectively substituted 1,3,5-triazinyl groups.
[0274] Those skilled in the art will understand that the expression "derivative" means that either the respective parent structure is selectively substituted, or any atom within the respective parent structure is replaced, for example, by an atom of another element.
[0275] In one embodiment of the present invention, each TADF material E B This includes: Each contains or is composed of one or more first chemical substructures represented by the chemical formula DI, [ka] ...Chemical formula DI Selectively, one or more second chemical substructures are independently selected from CN, CF3, and any one of the structures with chemical formulas AI, A-II, A-III, and A-IV, and [ka] ...Chemical formula AI [ka] ...Chemical formula A-II [ka] ...Chemical formula A-III [ka] ...Chemical formula A-IV A structure containing or composed of one of the following chemical formulas: LI, L-II, L-III, L-IV, LV, L-VI, L-VII, and L-VIII, [ka] ...Chemical formula LI [ka] ...Chemical formula L-II [ka] ...Chemical formula L-III [ka] ...Chemical formula L-IV [ka] ...chemical formula LV [ka] ...Chemical formula L-VI [ka] ...Chemical formula L-VII [ka] ...Chemical formula L-VIII Here, one or more first chemical substructures and one or more selective second chemical substructures are covalently bonded to a third chemical substructure via single bonds. In the chemical formula DI, # indicates the bond position of the single bond connecting each first chemical substructure to the third chemical substructure, according to the chemical formula DI. Z 2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=CR 1 R 2 , C=O, C=NR 1 , NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b , R d , R 1 and R 2 In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R 3 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R 3 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R 3 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R 3 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R 3 It is selectively replaced by, Here, one or more non-adjacent CH2 units are R 3 C=CR 3 , Si(R 3 )2, Ge(R 3 )2, Sn(R 3 )2, C=O, C=S, C=Se, C=NR3 , P(=O)(R 3 ), SO, SO2, NR 3 , O, S or CONR 3 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 3 It is selectively replaced by and C3-C 60 Heteroaryl, This is because it has one or more substituents R 3 It is selectively replaced by, R 3 In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R 4 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R 4 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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=NR4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R 4 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R 4 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R 4 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 4 It is selectively replaced by and C3-C 57 Heteroaryl, This is because it has one or more substituents R 4 It is selectively replaced by, Here, selectively, any substituent R a , R b , R d , R 1 , R 2 , R 3 and R 4 R is independent of each other. a , R b , R d , R 1 , R 2 , R 3 and R 4 Together with one or more adjacent substituents selected from, form a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system. R 4 In each case, a group consisting of the following is selected: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C2-C5 alkenyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C2-C5 alkynyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, C1-C5 alkyl, Ph, or CN. C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, Ph, or C1-C5 alkyl. N(C6-C 18 Ariel) 2, N(C3-C 17 Heteroaryl)2, and N(C3-C 17 (Heteroaryl)(C6-C 18 Ariel), a is an integer, and can be 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. In chemical formulas AI, A-II, A-III, and A-IV, The dotted lines indicate single bonds that connect the second chemical substructure, represented by chemical formulas AI, A-II, A-III, or A-IV, to the third chemical substructure. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1 Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1 If none of them are nitrogen (N), then group Q 1 At least one of them is CR 7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6Selected from, provided that in chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8 In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R 9 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R 9 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R 9 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R 9 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R 9 It is selectively replaced by, Here, one or more non-adjacent CH2 units are R 9 C=CR 9 , 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 9It is selectively replaced by and C3-C 60 Heteroaryl, This is because it has one or more substituents R 9 It is selectively replaced by, R 9 In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R 10 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R 10 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R10 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Select Replaced, C2-C 40 Alkenil, This is because it has one or more substituents R 10 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R 10 It is selectively replaced by, Here, one or more non-adjacent CH2 units are R 10 C=CR 10 , 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 10 It is selectively replaced by and C3-C 60 Heteroaryl, This is because it has one or more substituents R 10 It is selectively replaced by, R 10 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C2-C5 alkenyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C2-C5 alkynyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, C1-C5 alkyl, Ph, or CN. C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, Ph, or C1-C5 alkyl. N(C6-C 18 Ariel) 2, N(C3-C 17 Heteroaryl)2, and N(C3-C 17 (Heteroaryl)(C6-C 18 Ariel), R 7In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 It is defined as follows, however, in chemical formula EWG-I, at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms aromatic rings, which are condensed into a structure of chemical formula A-IV, where the selectively formed condensed ring system contains a total of 9 to 18 ring atoms. In the chemical formulas LI, L-II, L-III, L-IV, LV, L-VI, L-VII and L-VIII, Q 3 In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, provided that there is at least one Q 3 It is nitrogen (N), R 11 In each case, independently of each other, these are either the bonding positions of a single bond connecting the first or second chemical substructure to the third chemical substructure, or independently of each other, selected from the group consisting of the following: Hydrogen, deuterium, F, Cl, Br, I, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively substituted with deuterium. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently of each other: deuterium, C1-C5 alkyl, C6-C 18 Substituted with aryl groups, F, Cl, Br and I, R 12 R 6 It is defined as follows.
[0276] In a preferred embodiment of the present invention, Z2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=CR 1 R 2 , C=O, C=NR 1 , NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b , R d , R 1 and R 2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 3 )2, OR 3 , Si(R 3 )3, CF3, CN, F, Cl, Br, I, C1-C 40 Alkyl, This is because it has one or more substituents R 3 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 3 It is selectively replaced by and C3-C 60 Heteroaryl, This is because it has one or more substituents R 3 It is selectively replaced by, R 3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 4)2, OR 4 , Si(R 4 )3, CF3, CN, F, Br, I, C1-C 40 Alkyl, This is because it has one or more substituents R 4 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 4 It is selectively replaced by and C3-C 57 Heteroaryl, This is because it has one or more substituents R 4 It is selectively replaced by, Here, selectively, any substituent R a , R b , R d , R 1 , R 2 , R 3 and R 4 R is independent of each other. a , R b , R d , R 1 , R 2 , R 3 and R 4 Together with one or more adjacent substituents selected from, form a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system. R 4 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, C1-C5 alkyl, Ph, or CN. C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, C1-C5 alkyl, or Ph. N(C6-C 18 Ariel) 2, N(C3-C 17 Heteroaryl)2, and N(C3-C 17 (Heteroaryl)(C6-C 18 Ariel), a is an integer, and can be 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1 Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1 If none of them are nitrogen (N), then group Q 1 At least one of them is CR 7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6 Selected from, provided that in chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R 9 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 9 It is selectively replaced by and C3-C 60 Heteroaryl, This is because it has one or more substituents R 9 It is selectively replaced by, R 9 In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R 10 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 10 It is selectively replaced by and C3-C 60 Heteroaryl, This is because it has one or more substituents R 10 It is selectively replaced by, R 10 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, C1-C5 alkyl, Ph, or CN. C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, Ph, or C1-C5 alkyl. N(C6-C 18 Ariel) 2, N(C3-C 17 Heteroaryl)2, and N(C3-C 17 (Heteroaryl)(C6-C 18 Ariel), R 7 In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 Defined as follows, however, at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms an aromatic ring, which is condensed into a structure of chemical formula A-IV, with one or more substituents R 10 The rings are selectively substituted, and the fused ring system thus selectively formed contains a total of 9 to 18 ring atoms. Q 3 In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, but at least one Q 3 It is nitrogen (N), R 11 In each case, independently of each other, these are either the bonding positions of a single bond connecting the first or second chemical substructure to the third chemical substructure, or independently of each other, selected from the group consisting of the following: Hydrogen, deuterium, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively substituted with deuterium. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently of each other, and include deuterium, C1-C5 alkyl Lu group and C6-C 18 Substituted with an aryl group, R 12 R 6 It is defined as follows: Here, the maximum number of first and second chemical substructures bonded to the third chemical substructure is the number of available bonding positions in the third chemical substructure (i.e., substituent R 11 The number of TADF materials E is limited to only that number, and according to the aforementioned provisions, each TADF material E B It comprises at least one first chemical substructure, at least one second chemical substructure, and exactly one third chemical substructure.
[0277] In a more preferred embodiment of the present invention, Z 2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=CR 1 R 2 , C=O, C=NR 1 , NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b , R d , R 1 and R 2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 3 )2, OR 3 , Si(R 3 )3, CF3, CN, F, Cl, Br, I, C1-C 40 Alkyl, This is because it has one or more substituents R 3 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 3 It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 3 It is selectively replaced by, R 3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 4 )2, Si(R 4 )3, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R 4 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 4It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 4 It is selectively replaced by, Here, selectively, any substituent R a , R b , R d , R 1 , R 2 and R 3 R is independent of each other. a , R b , R d , R 1 , R 2 and R 3 Together with one or more adjacent substituents selected from, a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system is formed, where the ring system thus selectively formed is one or more substituents R 5 It is selectively replaced by, R 4 and R 5 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, CF3, CN, F, Me, i Pr, t Bu, N(Ph)2, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, a is an integer, and can be 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1 Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1If none of them are nitrogen (N), then group Q 1 At least one of them is CR 7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6 Selected from, however In chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 9 )2, OR 9 , Si(R 9 )3, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R 9 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 9 It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 9 It is selectively replaced by, R 9 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 10 )2, OR 10 , Si(R 10 )3, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R 10 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 10 It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 10 It is selectively replaced by, R 10 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, CF3, CN, F, N(Ph)2, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu, Ph, CN, CF3 or F, R 7 In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 Defined as follows, however, at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms aromatic rings, which are condensed into a structure of chemical formula A-IV, where the selectively formed condensed ring system contains a total of 9 to 18 ring atoms. Q 3 In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, but at least one Q 3 It is nitrogen (N), R 11 In each case, independently of each other, these are either the bonding positions of a single bond connecting the first or second chemical substructure to the third chemical substructure, or independently of each other, selected from the group consisting of the following: Hydrogen, deuterium, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively substituted with deuterium. C6-C 18 Ariel, This is deuterium, Me, i Pr, t It is selectively substituted with one or more substituents independently selected from the group consisting of Bu and Ph, R 12 R 6 It is defined as follows.
[0278] In a more preferred embodiment of the present invention, Z 2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=O, NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b , R d , R 1 and R 2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 3 )2, OR 3 , Si(R 3 )3, CF3, CN, C1-C5 alkyl, This is because it has one or more substituents R 3 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 3 It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 3 It is selectively replaced by, R 3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, CF3, CN, F, Me, i Pr, t Bu, N(Ph)2, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr,t Ph replaced by Bu and Ph, Here, selectively, any substituent R a , R b , R d , R 1 and R 2 R is independent of each other. a , R b , R d , R 1 and R 2 Together with one or more adjacent substituents selected from, a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system is formed, where the fused ring system thus selectively formed from the structure of chemical formula D-1 and the bonded rings formed by adjacent substituents contain a total of 13 to 40 ring atoms, preferably 13 to 30 ring atoms, more preferably 16 to 30 ring atoms. a is an integer, and can be 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1 Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1 If none of them are nitrogen (N), then group Q 1 At least one of them is CR 7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6 Selected from, provided that in chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 9 )2, OR 9 , Si(R 9 )3, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R 9 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 9 It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 9 It is selectively replaced by, R 9 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, CF3, CN, F, N(Ph)2, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu, Ph, CN, CF3 or F, R 7 In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 Defined as follows, however, at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms aromatic rings, which are condensed into a structure of chemical formula A-IV, where the selectively formed condensed ring system contains a total of 9 to 18 ring atoms. Q 3In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, but at least one Q 3 It is nitrogen (N), R 11 In each case, independently of each other, these are either the bonding positions of a single bond connecting the first or second chemical substructure to the third chemical substructure, or independently of each other, selected from the group consisting of the following: Hydrogen, deuterium, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, R 12 R 6 It is defined as follows.
[0279] In a more preferred embodiment of the present invention, Z 2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=O, NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b and R d In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 3 )2, OR 3 , Si(R 3 )3, CF3, CN, Me, i Pr, t Bu, Ph, where one or more hydrogen atoms are selectively and independently of each other, deuterium, Me, i Pr, t Replaced by Bu and Ph, Carbazolyl, where one or more hydrogen atoms are selectively and independently of each other, deuterium, Me, i Pr, t Replaced by Bu and Ph, Triazinyl, where one or more hydrogen atoms are selectively and independently of each other, deuterium, Me, i Pr, t Replaced by Bu and Ph, Pyrimidinyl, where one or more hydrogen atoms are selectively and independently of each other, deuterium, Me, i Pr, t Replaced by Bu and Ph, Pyridinyl, where one or more hydrogen atoms are selectively and independently of each other, deuterium, Me, i Pr, t Replaced by Bu and Ph, R 1 and R 2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 3 )2, OR 3 , Si(R 3 )3, CF3, CN, C1-C5 alkyl, This is because it has one or more substituents R 3 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 3 It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 3 It is selectively replaced by, R 3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, CF3, CN, F, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, Here, selectively, any substituent R a , R b , R d , R 1 and R 2 R is independent of each other.a , R b , R d , R 1 and R 2 Together with one or more adjacent substituents selected from, a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system is formed, where the selectively formed fused ring system composed of the structure of chemical formula D1 and the bonded rings formed by adjacent substituents contain a total of 13 to 40 ring atoms, preferably 13 to 30 ring atoms, more preferably 16 to 30 ring atoms. a is an integer, and can be 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1 Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1 If none of them are nitrogen (N), then group Q 1 At least one of them is CR 7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6 Selected from, provided that in chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 9 )2, OR 9 , Si(R 9 )3, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R 9 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 9 It is selectively replaced by and C3-C 17 Heteroaryl, This is because it has one or more substituents R 9 It is selectively replaced by, R 9 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, CF3, CN, F, N(Ph)2, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu, Ph, CN, CF3 or F, R 7 In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 Defined as follows, however, at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms aromatic rings, which are condensed into a structure of chemical formula A-IV, where the selectively formed condensed ring system contains a total of 9 to 18 ring atoms. Q 3 In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, but at least one Q 3 It is nitrogen (N), R 11 In each case, the first or second chemical substructure is tertiarily formed, independently of each other. It is either a bond site of a single bond connecting to a structural substructure, or it is selected independently from the group consisting of the following: Hydrogen, deuterium, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, R 12 R 6 It is defined as follows.
[0280] In a more preferred embodiment of the present invention, Z 2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=O, NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b and R d In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) 3 )2, OR 3 , Si(R 3 )3, CF3, CN, Me, i Pr, t Bu, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph substituted with Bu and Ph, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Carbazolyl substituted with Bu and Ph, R 1 and R 2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OR 3 , Si(R 3 )3, C1-C5 alkyl, This is because it has one or more substituents R 3 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R 3 It is selectively replaced by, R 3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, CF3, CN, F, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, Here, selectively, any substituent R a , R b , R d , R 1 and R 2 R is independent of each other. a , R b , R d , R 1 and R 2 Together with one or more adjacent substituents selected from, a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system is formed, where the selectively formed fused ring system composed of the structure of chemical formula D1 and the bonded rings formed by adjacent substituents contain a total of 13 to 40 ring atoms, preferably 13 to 30 ring atoms, more preferably 16 to 30 ring atoms. a is an integer, and can be 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1 If none of them are nitrogen (N), then group Q 1 At least one of them is CR 7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6 Selected from, provided that in chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh, N(Ph)2, Si(Me)3, Si(Ph)3, CF3, C N, F, Ho, i Pr, t Bu, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Carbazolyl substituted with Bu and Ph, R 7 In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 Defined as follows, however, at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms an aromatic ring, which is condensed into a structure of chemical formula A-IV, with one or more substituents R 10The rings are selectively substituted, and the fused ring system thus selectively formed contains a total of 9 to 18 ring atoms. Q 3 In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, but at least one Q 3 It is nitrogen (N), R 11 In each case, independently of each other, these are either the bonding positions of a single bond connecting the first or second chemical substructure to the third chemical substructure, or independently of each other, selected from the group consisting of the following: Hydrogen, deuterium, Me, i Pr, t Bu, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph is replaced by Bu and Ph. R 12 R 6 It is defined as follows.
[0281] In a more preferred embodiment of the present invention, Z 2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=O, NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b and R d In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, Si(Me)3, Si(Ph)3, CF3, CN, Me, i Pr, t Bu, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph substituted with Bu and Ph, and One or more hydrogen atoms selectively and independently form deuterium, Me, iPr, t Carbazolyl substituted with Bu and Ph, R 1 and R 2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, Here, selectively, any substituent R a , R b , R d , R 1 and R 2 R is independent of each other. a , R b , R d , R 1 and R 2 Together with one or more adjacent substituents selected from, a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system is formed, where the selectively formed fused ring system composed of the structure of chemical formula D1 and the bonded ring formed by adjacent substituents have a total of 13 to 40 ring atoms, It contains 13 to 30 ring atoms, more preferably 16 to 30 ring atoms. a is an integer, and can be 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1 Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1 If none of them are nitrogen (N), then group Q 1 At least one of them is CR7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6 Selected from, provided that in chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, Si(Me)3, Si(Ph)3, Me, i Pr, t Bu, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Carbazolyl substituted with Bu and Ph, R 7 In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 It is defined as such, but is either CN or CF3, however, it has at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms aromatic rings, which are condensed into a structure of chemical formula A-IV, where the selectively formed condensed ring system contains a total of 9 to 18 ring atoms. Q 3 In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, but at least one Q 3It is nitrogen (N), R 11 In each case, independently of each other, these are either the bonding positions of a single bond connecting the first or second chemical substructure to the third chemical substructure, or independently of each other, selected from the group consisting of the following: Hydrogen, deuterium, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph is replaced by Bu and Ph. R 12 R 6 It is defined as follows.
[0282] In a particularly preferred embodiment of the present invention, Z 2 In each case, they are independent of each other, directly coupled, CR 1 R 2 , C=O, NR 1 , O, SiR 1 R 2 Selected from the group consisting of S, S(O), and S(O)2, R a , R b and R d In each case, the following groups are selected independently from each other: Hydrogen, deuterium, CF3, CN, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, R 1 and R 2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, Here, selectively, any substituent R a , R b , R d , R 1 and R 2 R is independent of each other. a , R b , R d , R 1 and R 2 Together with one or more adjacent substituents selected from, a monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic system is formed, where the selectively formed fused ring system composed of the structure of chemical formula D1 and the bonded rings formed by adjacent substituents contain a total of 13 to 40 ring atoms, preferably 13 to 30 ring atoms, more preferably 16 to 30 ring atoms. is an integer, and is either 0 or 1. b is an integer, in each case either 0 or 1, where both b are always identical. Here, when integer a is 1, both integers b are 0, and when both integers b are 1, integer a is 0. Q 1 In each case, nitrogen (N) and CR are independent of each other. 6 and CR 7 Selected from, however, in chemical formula AI, two adjacent groups Q 1 Neither of these is nitrogen (N), and here, the base Q of the chemical formula AI. 1 If none of them are nitrogen (N), then group Q 1 At least one of them is CR 7 And, Q 2 In each case, nitrogen (N) and CR are independent of each other. 6 Selected from, provided that in chemical formulas A-II and A-III, at least one group Q 2 It is nitrogen (N), and two adjacent groups Q 2 Both are not nitrogen (N), R 6 and R 8 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, Me, i Pr, t Bu, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Ph replaced by Bu and Ph, One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr, t Carbazolyl substituted with Bu and Ph, R 7 In each case, the following are independently selected from the group consisting of structures represented by CN, CF3, and chemical formula EWG-I: [ka] ...Chemical formula EWG-I Here, R X R 6 It is defined as such, but is either CN or CF3, however, it has at least one R X The base is CN or CF3, In chemical formulas A-IV, two adjacent groups R 8 It selectively forms an aromatic ring, which is condensed into a structure of chemical formula A-IV, with one or more substituents R 10 The rings are selectively substituted, and the fused ring system thus selectively formed contains a total of 9 to 18 ring atoms. Q 3 In each case, nitrogen (N) and CR are independent of each other. 12 Selected from, but at least one Q 3 It is nitrogen (N), R 11 In each case, the first or second chemical substructure is tertiarily formed, independently of each other. It is either a bond site of a single bond connecting to a structural substructure, or it is selected independently from the group consisting of the following: Hydrogen, deuterium, Me, i Pr, t Bu, and One or more hydrogen atoms selectively and independently form deuterium, Me, i Pr,t Ph is replaced by Bu and Ph. R 12 R 6 It is defined as follows.
[0283] In a preferred embodiment of the present invention, a is always 1 and b is always 0.
[0284] In a preferred embodiment of the present invention, Z 2 In each case, it is a direct join.
[0285] In a preferred embodiment of the present invention, R a In each case, it is hydrogen.
[0286] In a preferred embodiment of the present invention, R a and R d In each case, it is hydrogen.
[0287] In a preferred embodiment of the present invention, Q 3 In each case, it is nitrogen (N).
[0288] In one embodiment of the present invention, in the chemical formula EWG-I, at least one group R X is CN.
[0289] In a preferred embodiment of the present invention, in the chemical formula EWG-I, exactly one group R X is CN.
[0290] In a preferred embodiment of the present invention, in the chemical formula EWG-I, exactly one R X The group is CN, and in the chemical formula EWG-I, R X The base is not CF3.
[0291] Examples of the first chemical substructures according to the present invention are shown below, but this does not mean that the present invention is limited to these examples: [ka]
change
change
change
change
change
change
change
change
change
change
change
change
change
change
change
[0292] Here, the aforementioned definition applies.
[0293] Examples of the second chemical substructure according to the present invention are shown below, but this does not mean that the present invention is limited to these examples: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0294] Here, the aforementioned definition applies.
[0295] In a preferred embodiment of the present invention, each TADF material E Bis the chemical formula E B -I, E B -NO B -III, E B -IV, E B -V, E B -Work, E B -Work I, E B -VIII, E B -IX, E B -X and E B -Having a structure represented by any one of XI: [ka] ...Chemical formula E B -I [ka] ...Chemical formula E B -II [ka] ...Chemical formula E B -III [ka] ...Chemical formula E B -IV [ka] ...Chemical formula E B -V [ka] ...Chemical formula E B -VI [ka] ...Chemical formula E B -VII [ka] ...Chemical formula E B -VIII [ka] ...Chemical formula E B -IX [ka] ...Chemical formula EB-X [ka] ...Chemical formula E B -XI Here, R 13 R 11 It is defined as follows, however, R 13 This is not the bonding position of a single bond that connects the first or second chemical substructure to the third chemical substructure, R Y The is selected from CN and CF3, or R Y It contains or is composed of the structure shown in the following chemical formula BN-I: [ka] ...Chemical formula BN-I This is due to a single bond represented by a dotted line, resulting in the chemical formula E B -I, E B -NO B -III, E B -IV, E B -V, E B -Work, E B -Work I, E B -VIII or E B - The structure is coupled to IX, where exactly one R BN The base is CN, and the other two R BN The base is hydrogen (H) in both cases. The definitions mentioned above apply to all other cases.
[0296] In a preferred embodiment of the present invention, R 13 In each case, it is hydrogen.
[0297] In one embodiment of the present invention, R Y In each case, it is CN.
[0298] In one embodiment of the present invention, R Y In each case, it is CF3.
[0299] In one embodiment of the present invention, R Y In each case, the structure is represented by the chemical formula BN-I.
[0300] In a preferred embodiment of the present invention, R Y In each case, the structures are selected independently from those represented by CN and the chemical formula BN-I.
[0301] In a preferred embodiment of the present invention, each TADF material E B This is the chemical formula E to which the aforementioned definition applies. B -I, E B -NO B -III, E B -IV, E B -V, E B -Work, E B -Work I and E B -X has a structure that can be represented by any chemical formula among the following:
[0302] In a preferred embodiment of the present invention, each TADF material E B This is the chemical formula E to which the aforementioned definition applies. B -I, E B -NO B -III, E B -V and E B -X has a structure that can be represented by any chemical formula among the following:
[0303] TADF material E for use in organic electroluminescent elements according to the present invention B Examples are shown below, but this is merely an example of a suitable TADF material E in the context of the present invention. B That does not mean...
[0304] Chemical formula E B -I TADF material E BA non-restrictive example is shown below: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0305] Chemical formula E B -II TADF material E B A non-restrictive example is shown below: [ka] [ka] [ka] [ka] [ka]
[0306] Chemical formula E B -III TADF material E B A non-restrictive example is shown below: [ka] [ka] [ka] [ka]
[0307] Chemical formula E B - TADF material E by IV B A non-restrictive example is shown below: [ka]
[0308] Chemical formula E B -V TADF material E B A non-restrictive example is shown below: [ka]
[0309] Chemical formula E B -VI-based TADF material E B A non-restrictive example is shown below: [ka]
[0310] Chemical formula E B -VII TADF material EB A non-restrictive example is shown below: [ka]
[0311] Chemical formula E B -TADF material E by VIII B A non-restrictive example is shown below: [ka]
[0312] Chemical formula E B - TADF material E by IX B A non-restrictive example is shown below: [ka] [ka]
[0313] Chemical formula E B -X-based TADF material E B A non-restrictive example is shown below: [ka] [ka]
[0314] Chemical formula E B - TADF material E by XI B A non-restrictive example is shown below: [ka]
[0315] TADF material E BThe synthesis of is achieved via standard reactions and reaction conditions well known to those skilled in the art. Generally, in the first step, a coupling reaction, preferably a palladium-catalyzed coupling reaction, is carried out to form chemical formula E B -III, E B -IV and E B -TADF material E using one of the following: B The following is an example illustrating the synthesis of: [ka]
[0316] E1 is any boronic acid (R B =H) or the corresponding boronic acid ester (R B = alkyl or aryl), and in particular, two R B This forms a ring, and for example, pinacol boronic acid ester can be provided. E2 is used as the second reactant, where Hal represents a halogen and may be I, Br or Cl, but preferably Br. The reaction conditions for such palladium-catalyzed coupling reactions are known to those skilled in the art, for example from WO2017 / 005699, and it is known that the reactants E1 and E2 are interchangeable as shown below to optimize the reaction yield: [ka]
[0317] In the second step, a TADF molecule is obtained via the reaction of a nitrogen heterocycle with an aryl halide, preferably an aryl fluoride E3, in an aromatic nucleophilic substitution reaction. Typical conditions include the use of a base such as tripotassium phosphate or sodium hydride, in an aprotic polar solvent such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF). [ka]
[0318] In particular, 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), or a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1,8 It may also be a 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).
[0319] Alternatively, halogen-substituted carbazoles, particularly 3-bromocarbazole, may be used as E4.
[0320] In subsequent reactions, a boronic acid ester group or boronic acid ester group is exemplary introduced at the position of one or more halogen substituents introduced via E4, and the corresponding carbazolylboronic acid or ester, such as carbazole-3-yl-boronic acid ester or carbazole-3-yl-boronic acid, can be produced, for example, by reaction with (pinacolate)diborone (CAS No. 73183-34-3). Then, the corresponding halogen Chemical reactants, for example, R a -Hal, preferably, R a -Cl and R a - Through a coupling reaction with Br, one or more substituents R are added in place of the boronic acid ester group or boronic acid group. a , R b or R d This could be introduced.
[0321] As an alternative, substituent Ra [R a -B(OH)2], R b [R b -B(OH)2] or R d [R d One or more substituents R are introduced via DH at the position of one or more halogen substituents through the reaction of -B(OH)2] with a boronic acid or corresponding boronic acid ester. a , R b or R d This could be introduced.
[0322] Also, TADF material E B It can be obtained similarly. Also, TADF material E B This can be obtained by any alternative synthesis route suitable for the purpose.
[0323] An alternative synthetic route may involve introducing a nitrogen heterocycle into an aryl halide or aryl pseudohalide, preferably an aryl bromide, aryl iodide, aryl triflate, or aryl tosylate, via copper or palladium-catalyzed coupling.
[0324] Phosphorescent material P B In the context of the present invention, phosphorescent material P B This method utilizes intramolecular spin-orbit interaction (heavy atom effect) induced by metal atoms to obtain light emission from the triplet state (i.e., the excited triplet state, generally the lowest excited triplet state T1). In other words, phosphorescent material P B It can emit phosphorescence at room temperature (i.e., about 20°C), and this is generally due to 10% by weight of P in poly(methyl methacrylate) (PMMA). B It is measured from the spin-coated film.
[0325] While phosphorescent material P can emit phosphorescence according to its definition, it is selectively included in the organic electroluminescent element of the present invention as a selective excitation energy transfer component EET-2. BPreferably, it functions as an "energy pump" that is not primarily an emitter material. That is, the phosphorescent material P contained in the light-emitting layer B B This mainly involves small FWHM emitters S with excitation energies of 1 or more. B They are moved to the next layer, and then they act as the main emitter material. Phosphorescent material P in the light-emitting layer B B It is preferable that its primary function is not to emit light. However, it can emit light to some extent.
[0326] Generally, it is understood that all phosphorescent complexes used in organic electroluminescent elements in the latest technology can also be used in organic electroluminescent elements according to the present invention.
[0327] Phosphorescent material P used in organic electroluminescent elements B It is common knowledge to those skilled in the art that the phosphorescent material is a complex of Ir, Pd, Pt, Au, Os, Eu, Ru, Re, Ag, and Cu, preferably Ir, Pt, and Pd, and more preferably Ir and Pt, according to the present invention. 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 use in organic electroluminescent devices and know how to adjust the luminescence of the complex through structural changes.
[0328] See the following examples: 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: 1 0.1002 / 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.Wuc, Z.-G.Wua, Y.-X.Zheng, J.-L.Zuo, Y.Pan, Coordination Chemistry Reviews 2018, 374, 55, DOI: 10.1016 / j.ccr.2018.06.014。
[0329] For example, US2020274081(A1), US20010019782(A1), US20020034656(A1), US20030138657(A1), US2005123791(A1), US20060065890(A1), US20060134462(A1), US20070034863(A1), US20070111026(A1), US2007034863(A1), US2007138437(A1), US20080020237(A1), US20080297033(A1), US2008210930( A1), 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), US2011114922(A1), US2003054198(A1), and EP2730583(A1) are phosphorescent materials P in the context of the present invention. B Phosphorescent materials that can be used are disclosed. This is understood not to mean that the present invention is limited to organic electroluminescent elements that include phosphorescent materials described in one of the named reference documents.
[0330] As indicated in US2020274081(A1), examples of phosphorescent complexes for use in organic electroluminescent devices such as those of the present invention include the complexes listed below. Again, it should be understood that the present invention is not limited to these examples. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0331] As mentioned above, those skilled in the art will see that any phosphorescent complex used in the latest technology is a phosphorescent material P in the context of the present invention. B They will recognize that it is suitable for that purpose.
[0332] In one embodiment of the present invention, each phosphorescent material P contained in the light-emitting layer B B It contains iridium (Ir).
[0333] In one embodiment of the present invention, at least one phosphorescent material P B Preferably, each phosphorescent material P contained in the light-emitting layer B B It is an organometallic complex containing iridium (Ir) or platinum (Pt).
[0334] In one embodiment of the present invention, at least one phosphorescent material P is included in the light-emitting layer B. B Preferably, each phosphorescent material P B It is an organometallic complex containing iridium (Ir).
[0335] In one embodiment of the present invention, at least one phosphorescent material P is included in the light-emitting layer B. B Preferably, each phosphorescent material P B It is an organometallic complex containing platinum (Pt).
[0336] Also, phosphorescent material P B A non-restrictive example is the following general chemical formula P B Includes compounds represented by -I: [ka] ...Chemical formula P B -I.
[0337] Chemical formula P B In -I, M is selected from the group consisting of Ir, Pt, Pd, Au, Eu, Ru, Re, Ag, and Cu. n is an integer between 1 and 3. X 2 and Y 1 In each case, they independently form bidentate monoanionic ligands.
[0338] In one embodiment of the present invention, each phosphorescent material P contained in the light-emitting layer B B The chemical formula P is as follows: B -Includes or is composed of a structure by -I: [ka] ...Chemical formula P B -I Here, M is selected from the group consisting of Ir, Pt, Pd, Au, Eu, Ru, Re, Ag, and Cu. n is an integer between 1 and 3. X 2 and Y 1 In each case, they independently form bidentate monoanionic ligands.
[0339] Chemical formula P B Examples of compounds represented by -I are shown below with chemical formula P B -II or chemical formula P B Includes compounds represented by -III: [ka] ...Chemical formula P B -II [ka] ...Chemical formula P B -III
[0340] Chemical formula P B -II and P B In -III, X' is an aromatic ring bonded to M by a carbon (C) bond, and Y' is a ring that forms a ring by being coordinated to M by a nitrogen (N) bond.
[0341] X' and Y' can bond together, and X' and Y' can form a new ring. Chemical formula P B -III, Z 3 P is a bidentate ligand containing two oxygen (O) atoms. Its chemical formula is P. B -II and P B In -III, M is preferably Ir from the viewpoint of high efficiency and long lifespan.
[0342] Chemical formula P B -II and P B In -III, the aromatic ring X' is, for example, C6-C 30 Aryl, preferably C6-C 16 Aaryl, more preferably C6-C 12 Aryl, particularly preferably C6-C 10 It is an aryl molecule, where X' is one or more substituents R in each case, which are selectively present. E It will be replaced by this.
[0343] Chemical 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, more preferably C2-C 15 Heteroaryl, particularly preferably C2-C 10 It is a heteroaryl compound, where Y' is selectively one or more substituents R in each case. E It is replaced by, for example, one or more substituents R. E It may also be a C1-C5 heteroaryl substituted with [the appropriate compound].
[0344] Chemical formula PB -II and P B -III contains a bidentate ligand Z with two oxygen (O) atoms. 3 For example, a C2-C molecule with two oxygen atoms. 30 Bidentate ligands, preferably C2-C having two oxygen atoms. 25 Bidentate ligands, more preferably C2-C having two oxygen atoms 20 Bidentate ligands, more preferably C2-C having two oxygen atoms. 15 Bidentate ligands, particularly preferably C2-C having two oxygen atoms. 10 It is a bidentate ligand, and here, Z 3 In each case, one or more substituents R are selectively selected. E It is replaced by Z. 3 For example, one or more substituents R selectively selected E It may also be a C2-C5 bidentate ligand having two oxygen atoms substituted by [a specific group].
[0345] R E In each case, the following groups are selected independently of each other: Hydrogen, deuterium, N(R) 5E )2, OR 5E , SR 5E , Si(R 5E )3, CF3, C N, halogen, C1-C 40 Alkyl, This is because it has one or more substituents R 5E Selectively substituted, one or more non-adjacent CH2 groups are 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 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R 5ESelectively substituted, one or more non-adjacent CH2 groups are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 5E It is selectively replaced by and C3-C 57 Heteroaryl, This is because it has one or more substituents R 5E It is selectively replaced by [this]. R 5E In each case, the following groups are selected independently of each other: Hydrogen, deuterium, N(R) 6E )2, OR 6E , SR 6E , Si(R 6E )3, CF3, CN, F, C1-C 40 Alkyl, This is because it has one or more substituents R 6E Selectively substituted, one or more non-adjacent CH2 groups are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R 6E It is selectively replaced by and C3-C 57 Heteroaryl, This is because it has one or more substituents R 6E It is selectively replaced by [this].
[0346] R 6E In each case, the following groups are selected independently of each other: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C6-C 18 Ariel, This is selectively substituted with one or more C1-C5 alkyl substituents, C3-C 17 Heteroaryl, This is selectively substituted with one or more C1-C5 alkyl substituents, N(C6-C 18 Ariel) 2, N(C3-C 17 Heteroaryl)2, and N(C3-C 17 (Heteroaryl)(C6-C 18 Ariel).
[0347] Substituent R E , R 5E or R 6E R consists of one or more substituents R that are independent of and selectively determined from each other. E , R 5E , R 6E and / or X', Y' and Z 3 Together, they can form monocyclic or polycyclic, aliphatic, aromatic, or heteroaromatic ring systems.
[0348] Chemical formula PB Non-limiting 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), fac-tris(2-(3-p-xylyl)phenyl)pyridineiridium(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, fa c-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.
[0349] Chemical formula P B Other non-limiting examples of compounds represented by -II are shown below with chemical formula P B -II-1~P B It contains compounds represented by -II-11. In the structural formula, "Me" represents a methyl group. [ka] [ka] [ka]
[0350] Chemical formula P B Other non-limiting examples of compounds represented by -III are shown below with chemical formula P B -III-1~P B It contains compounds represented by -III-6. In the structural formula, "Me" represents a methyl group. [ka]
[0351] Additionally, 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 for phosphorescent materials, Ir(ppy)3 and Hex-Ir(ppy)3 are often used for green emission.
[0352] Excyplex It has been demonstrated that TADF materials can convert an excited triplet state (preferably T1) to an excited singlet state (preferably S1) via reverse intersystem crossing (RISC). Furthermore, this generally results in a small ΔE ST A value is required, which is by definition TADF material E B In this case, it has been explicitly stated that it is less than 0.4 eV. Also, as mentioned above, this is because the TADF molecule E is spatially separated so that the HOMO and LUMO are largely separated by the (electron) donor group and (electron) acceptor group, respectively. B This is achieved by designing ΔE ST Another strategy for reaching species with small values is to form an excyplex. As those skilled in the art know, an excyplex is an excited-state charge transfer complex (i.e., an excited-state donor-acceptor complex) formed between a donor molecule and an acceptor molecule. Those skilled in the art will know that in an excyplex, the spatial separation of the HOMO (on the donor molecule) and the LUMO (on the acceptor molecule) is typically somewhat small ΔE ST It is understood that the excited triplet state (preferably T1) can be switched to the excited singlet state (preferably S1) via reverse intersystem crossing (RISC) by having a value.
[0353] In fact, as is known to those skilled in the art, TADF materials are not materials that have TADF follow-up emission, but are simply RISC-transferable from an excited triplet state to an excited singlet state on their own, as described above. Furthermore, TADF materials consist of virtually two materials, preferably two host materials H B More preferably, p-host material H P and n-host material H N It is well known to those skilled in the art that the excyplex is formed from (see below), and the host material H B (Generally, H P and H N It is understood that the material itself is TADF material.
[0354] Those skilled in the art will understand that not only any material contained in the same layer, particularly the same EML, but also materials contained in adjacent layers and in very close proximity at the interface between those adjacent layers can form an exciplex together. Those skilled in the art will understand that pairs of materials forming an exciplex, particularly p-host H P and n-host H N A method for selecting a pair of materials, and selection criteria including HOMO and / or LUMO energy level requirements for the two components of the aforementioned material pair, are known. That is, when excyplex formation is required, one component, for example, p-host material H P The highest occupied orbital (HOMO) of the n-host material H is the highest occupied orbital of the other component, for example, the n-host material H N The energy of the HOMO is at least 0.20 eV higher, and one component, for example, p-host material H P The lowest unoccupied orbital (LUMO) is the other component, for example, the n-host material H N Its energy is at least 0.20 eV higher than the LUMO.
[0355] It is common knowledge to those skilled in the art that when an exciplex is present in an organic electroluminescent device, particularly an OLED EML, the exciplex functions as an emitter material and can emit light when voltage and current are applied to the device. As is known from the latest technology and generally, the exciplex is non-radiative and, for example, when included in the EML of an organic electroluminescent device, can transfer excitation energy to the emitter material.
[0356] Host material H capable of forming an excyplex together B A non-restrictive example is shown below, where the donor molecule (i.e., p-host H) is the donor molecule. P ) is selected from the following structures: [ka]
[0357] Acceptor molecule (i.e., n-host H) N ) is selected from the following structures: [ka] [ka] [ka] [ka]
[0358] In the context of the present invention, excyplex refers to any material included in the light-emitting layer B, for example, a material with different excitation energy transfer components (E B And / or EET-2), as well as the excitation energy transfer component (E B and / or EET-2) and small FWHM emitter S B , or host material H Band excitation energy transfer component E B Or EET2 or small FWHM emitter S B It is understood that they are formed from different host materials H, preferably, however, they are different from each other as described above. B It is formed from this. It is also understood that an excyplex may be formed, and the excitation energy transfer component itself may not act.
[0359] Small FWHM Emitter S B The present invention provides a small half-width (FWHM) emitter S B This may generally be any emitter having an emission spectrum in which the FWHW measured from a spin-coated film having 1-5% by weight, particularly 2% by weight, of emitters in poly(methyl methacrylate) PMMA at room temperature (i.e., approximately 20°C) is 0.25 eV or less (≤0.25). As an alternative, a small FWHM emitter S B The emission spectrum is generally observed at room temperature (i.e., approximately 20°C) with 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene. B It can be measured in a solution containing [the specified value].
[0360] In a preferred embodiment of the present invention, a small FWHM emitter S B This is 1-5% by weight, particularly 2% by weight, of the emitter S in PMMA at room temperature (i.e., (approximately) 20°C). B Any emitter having an emission spectrum exhibiting FWHM of ≤0.24eV, more preferably ≤0.23eV, even more preferably ≤0.22eV, ≤0.21eV, or ≤0.20eV, measured from a spin-coated film having the above characteristics. Alternatively, a small FWHM emitter. S B The emission spectrum is generally observed at room temperature (i.e., approximately 20°C) with 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene. B It can be measured in a solution containing the following. In another embodiment of the present invention, each small FWHM emitter S BThis indicates FWHM for ≤0.19eV, ≤0.18eV, ≤0.17eV, ≤0.16eV, ≤0.15eV, ≤0.14eV, ≤0.13eV, ≤0.12eV, or ≤0.11eV.
[0361] In one embodiment of the present invention, each small FWHM emitter S B This is achieved at room temperature with (1-5 wt%, especially 2 wt% emitter S B When measured with PMMA, it emits maximum emission in the wavelength range of 510nm to 550nm.
[0362] In one embodiment of the present invention, each small FWHM emitter S B This is 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene at room temperature (i.e., (approximately) 20°C). B When measured, it emits maximum light in the wavelength range of 510nm to 550nm.
[0363] TADF material E included in the light-emitting layer B of the organic electroluminescent element according to the present invention B This is also an emitter having an emission spectrum that selectively exhibits an FWHM of 0.25 eV or less (≤0.25 eV). Selectively, the TADF material E included in the light-emitting layer B of the organic electroluminescent element according to the present invention B Furthermore, it can exhibit maximum emission within the aforementioned wavelength range (i.e., 510 nm to 550 nm).
[0364] In one embodiment of the present invention, the relationship represented by the following formula (29) applies: 510nm ≤ λ max (S B ) ≤ 550nm (29) Here, .'' max (S B ) is a small FWHM emitter S in the context of the present invention. B This shows the maximum light emission.
[0365] In one embodiment, the aforementioned relationship represented by formula (29) applies to the material constituting the light-emitting layer B of the organic electroluminescent element according to the present invention.
[0366] In a preferred embodiment of the present invention, a small FWHM emitter S B This is an organic emitter, which in the context of the present invention means that it does not contain any transition metals. Preferably, the small FWHM emitter S according to the present invention B It is mainly composed of hydrogen (H), carbon (C), nitrogen (N), and boron (B), but may also contain, for example, oxygen (O), silicon (Si), fluorine (F), and bromine (Br).
[0367] In a preferred embodiment of the present invention, a small FWHM emitter S B This is a fluorescent emitter, which, in the context of the present invention, means that the emitter can emit light at room temperature when electronically excited (for example, in the photoelectronic device according to the present invention), and here the luminescence excited state is a singlet state.
[0368] In one embodiment of the present invention, a small FWHM emitter S B This is achieved at room temperature with (1-5 wt%, especially 2 wt% emitter S B When measured with PMMA, it exhibits a photoluminescence quantum yield (PLQY) of 50% or higher.
[0369] In a preferred embodiment of the present invention, a small FWHM emitter S B This is achieved at room temperature with (1-5 wt%, especially 2 wt% emitter S B When measured with PMMA, it exhibits a photoluminescence quantum yield (PLQY) of 60% or higher.
[0370] In a more preferred embodiment of the present invention, a small FWHM emitter S B This is achieved at room temperature with (1-5 wt%, especially 2 wt% emitter S B When measuring with PMMA, more than 70% of photos This shows the luminescence quantum yield (PLQY).
[0371] In a more preferred embodiment of the present invention, a small FWHM emitter S B This is achieved at room temperature with (1-5 wt%, especially 2 wt% emitter S B When measured with PMMA, it exhibits a photoluminescence quantum yield (PLQY) of 80% or higher.
[0372] In a particularly preferred embodiment of the present invention, a small FWHM emitter S B This is achieved at room temperature with (1-5 wt%, especially 2 wt% emitter S B When measured with PMMA, it exhibits a photoluminescence quantum yield (PLQY) of over 90%.
[0373] In one embodiment of the present invention, a small FWHM emitter S B This is 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene at room temperature (i.e., (approximately) 20°C). B When measured, it exhibits a photoluminescence quantum yield (PLQY) of 50% or more.
[0374] In a preferred embodiment of the present invention, a small FWHM emitter S B This is 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene at room temperature (i.e., (approximately) 20°C). B When measured, it exhibits a photoluminescence quantum yield (PLQY) of 60% or higher.
[0375] In a more preferred embodiment of the present invention, a small FWHM emitter S B This is 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene at room temperature (i.e., (approximately) 20°C). B When measured, it exhibits a photoluminescence quantum yield (PLQY) of over 70%.
[0376] In a more preferred embodiment of the present invention, a small FWHM emitter S B This is 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene at room temperature (i.e., (approximately) 20°C).B When measured, it exhibits a photoluminescence quantum yield (PLQY) of over 80%.
[0377] In a particularly preferred embodiment of the present invention, a small FWHM emitter S B This is 0.001-0.2 mg / mL of emitter S in dichloromethane or toluene at room temperature (i.e., (approximately) 20°C). B When measured, it exhibits a photoluminescence quantum yield (PLQY) of over 90%.
[0378] A person skilled in the art will find a small FWHM emitter S that satisfies the aforementioned requirements or preferred characteristics. B I know how to design it.
[0379] In the context of the present invention, small FWHM emitter S B Another type of molecule suitable for providing this is the NRCT (near-range-charge-transfer) emitter.
[0380] Typical NRCT emitters are described in the literature as exhibiting delayed components in time-resolved photoluminescence spectra and showing near-range HOMO-LUMO separation. See the following 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.
[0381] Typical NRCT emitters exhibit only one emission band in their emission spectrum, and The fluorescent emitter exhibits multiple unique emission bands due to vibrational progression.
[0382] Those skilled in the art will understand that in the context of the present invention, a small FWHM emitter S BMethods for designing and synthesizing NRCT emitters suitable for this purpose are known. For example, the emitter disclosed in EP3109253(A1) is a small FWHM emitter S in the context of the present invention. B It may also be used as such.
[0383] Also, for example, US2014058099(A1), US2009295275(A1), US2012319052(A1), EP2182040(A2), US2018069182(A1), US2019393419(A1), US2020006671(A1), US2020098991(A1), US2020176684(A1 ), US2020161552(A1), US2020227639(A1), US2020185635(A1), EP3686206(A1), EP3686206(A1), WO2020217229(A1), WO2020208051(A1) and US2020328351(A1) are small FWHM emitters S for use according to the present invention. B We disclose an emitter material suitable for this purpose.
[0384] In the context of the present invention, small FWHM emitter S B A group of emitters usable as such are boron (B)-containing emitters containing or composed of the structure shown by the chemical formula DABNA-I below: [ka] ...Chemical formula DABNA-I Here, Each of the rings A', B', and C' independently represents an aromatic or heteroaromatic ring containing 5 to 24 ring atoms, of which 1 to 3 are heteroatoms independently selected from N, O, S, and Se. Here, in each aromatic ring or heteroaromatic ring A', B', and C', one or more hydrogen atoms are selectively and independently substituent R DABNA-1 It is replaced by, which in each case is independently selected from the following group: 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, halogen (F, Cl, Br, I), C1-C 40 Alkyl, This selectively involves one or more substituents R DABNA-2 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C1-C 40 Alkoxy, This selectively involves one or more substituents R DABNA-2 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C1-C 40 Thioalkoxy, This selectively involves one or more substituents R DABNA-2 Replaced by, Here, one or more non-adjacent CH2 groups are selectively R DABNA-2 C=CR DABNA-2 , C≡C, Si(R DABNA-2 )2, Ge(R DABNA-2 )2, Sn(RDABNA-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 Replaced by, C2-C 40 Alkenil, This selectively involves one or more substituents R DABNA-2 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C2-C 40 Alkinil, This selectively involves one or more substituents R DABNA-2 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C6-C 60 Ariel, This selectively involves one or more substituents R DABNA-2 Replaced by, C3-C 57 Heteroaryl, This selectively involves one or more substituents R DABNA-2 Replaced by, and Aliphatic cyclic amines containing 4 to 18 carbon atoms and 1 to 3 nitrogen atoms, RDABNA-2 In each case, the following groups are selected independently from each other: 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, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C1-C5 alkoxy, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C1-C5 thioalkoxy, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C2-C5 alkenyl, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C2-C5 alkynyl, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-6 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-6 Replaced by, and Aliphatic cyclic amines containing 4 to 18 carbon atoms and 1 to 3 nitrogen atoms, Here, R DABNA-1 and RDABNA-2 Two or more adjacent substituents selected from the above selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems condensed to adjacent rings A', B', or C', where the selectively formed condensed ring systems (i.e., each ring A', B', or C' and the additional rings selectively condensed to them) contain a total of 8 to 30 ring atoms. Y a and Y b These are independent of each other, directly (single) coupled, NR DABNA-3 O, S, C(R DABNA-3 )2, Si(R DABNA-3 )2, BR DABNA-3 Selected from and Se, R DABNA-3 In each case, the following groups are selected independently from each other: 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, halogen (F, Cl, Br, I), C1-C 40 Alkyl, This selectively involves one or more substituents R DABNA-4 Replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Alkoxy, This selectively involves one or more substituents R DABNA-4 Replaced by, Here, one or more non-adjacent CH2 units are R DABNA-4 C=CRDABNA-4 , C≡C, Si(R DABNA-4 )2, Ge(R DABNA-4 )2, Sn(R DAB NA-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 Replaced by, C1-C 40 Thioalkoxy, This selectively involves one or more substituents R DABNA-4 Replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C 40 Alkenil, This selectively involves one or more substituents R DABNA-4 Replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C 40 Alkinil, This selectively involves one or more substituents R DABNA-4 Replaced by, Here, one or more non-adjacent CH2 units are R DABNA-4 C=CR DABNA-4 , C≡C, Si(RDABNA-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 Replaced by, C6-C 60 Ariel, This selectively involves one or more substituents R DABNA-4 Replaced by, C3-C 57 Heteroaryl, This selectively involves one or more substituents R DABNA-4 Replaced by, and Aliphatic cyclic amines containing 4 to 18 carbon atoms and 1 to 3 nitrogen atoms, R DABNA-4 In each case, the following groups are selected independently from each other: 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, halogen (F, Cl, Br, I), C1-C 40 Alkyl, This selectively involves one or more substituents R DABNA-5 Replaced by, Here, one or more non-adjacent CH2 units are 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 ), O, S or CONR DABNA-5 Replaced by, C1-C 40 Alkoxy, This selectively involves one or more substituents R DABNA-5 Replaced by, Here, one or more non-adjacent CH2 units are RDABNA-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 ), O, S or CONR DABNA-5 Replaced by, C1-C 40 Thioalkoxy, This selectively involves one or more substituents R DABNA-5 Replaced by, Here, one or more non-adjacent CH2 units are R DABNA-5 C=CR DABNA-5 , C≡C, Si(R DABNA-5 )2, Ge(R DABNA-5 )2, Sn(R DAB NA-5 )2, C=O, C=S, C=Se, C=NR DABNA-5 , P(=O)(R DABNA-5 ), O, S or CONR DABNA-5 Replaced by, C2-C 40 Alkenil, This selectively involves one or more substituents R DABNA-5 Replaced by, Here, one or more non-adjacent CH2 units are 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 ), O, S or CONR DABNA-5 Replaced by, C2-C 40 Alkinil, This selectively involves one or more substituents R DABNA-5 Replaced by, Here, one or more non-adjacent CH2 units are 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 ), O, S or CONR DABNA-5 Replaced by, C6-C 60 Ariel, This selectively involves one or more substituents R DABNA-5 Replaced by, C3-C 57 Heteroaryl, This selectively involves one or more substituents R DABNA-5 Replaced by, and Aliphatic cyclic amines containing 4 to 18 carbon atoms and 1 to 3 nitrogen atoms, R DABNA-5 In each case, the following groups are selected independently from each other: 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, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C1-C5 alkoxy, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively R DABNA-6 C=CR DABNA-6 , C≡C, Si(R DABNA-6 )2, Ge(RDABNA-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 Replaced by, C1-C5 thioalkoxy, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C2-C5 alkenyl, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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 Replaced by, C2-C5 alkynyl, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, one or more non-adjacent CH2 groups are selectively 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=NRDABNA-6 , P(=O)(R DABNA-6 ), SO, SO2, NR DABNA-6 , O, S or CONR DABNA-6 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-6 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-6 Replaced by, and Aliphatic cyclic amines containing 4 to 18 carbon atoms and 1 to 3 nitrogen atoms, Here, R DABNA-3 , R DABNA-4 and R DABNA-5 Two or more adjacent substituents selected from the above selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, where the selectively formed fused ring systems contain a total of 8 to 30 ring atoms. R DABNA-6 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh (Ph=phenyl), SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, Ph, CN, CF3, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C2-C5 alkenyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C2-C5 alkynyl, Here, one or more hydrogen atoms are selectively and independently substituted by deuterium, CN, CF3, or F. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, CF3, F, C1-C5 alkyl, SiMe3, SiPh3, or C6-C 18 Substituted by aryl substituents, C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, CF3, F, C1-C5 alkyl, SiMe3, SiPh3, or C6-C 18 Substituted by aryl substituents, N(C6-C 18 Ariel) 2, N(C3-C 17 Heteroaryl)2, and N(C3-C 17 (Heteroaryl)(C6-C 18 Ariel), Here, Y a and Y b one of the following, or Y a and Y b Both of them are NR DABNA-3 , C(R DABNA-3 )2, Si(R DABNA-3 )2 or BR DABNA-3 If so, the one or two substituents R DABNA-3 These are the adjacent rings A' and B'(Y a =NR DABNA-3 , C(R DABNA-3 )2, Si(R DABNA-3 )2 or BR DABNA-3 ), or A' and C'(Y b =NR DABNA-3 , C(R DABNA-3 )2, Si(R DABNA-3 )2 or BR DABNA-3 ) directly (single) coupled to one or both of NR, or independently in each case, DABNA-1 O, S, C(R DABNA-1 )2, Si(R DABNA-1 )2, BRDABNA-1 And can be bonded via a linking atom or atomic group selected from Se, Here, two or more structures of the chemical formula DABNA-I are selectively joined to each other, preferably condensed by sharing at least one, more preferably exactly one bond. Here, two or more structures of the chemical formula DABNA-I are selectively present in the emitter, sharing at least one, preferably exactly one aromatic or heteroaromatic ring (i.e., the ring may be part of two structures of the chemical formula DABNA-I), wherein the ring is preferably one of the rings A', B', and C' of the chemical formula DABNA-I, and also R DABNA-1 , R DABNA-2 , R DABNA-3 , R DABNA-4 , R DABNA-5 and R DABNA-6 , especially R DABNA-3 The covalent ring may be any aromatic substituent or heteroaromatic substituent selected from the above, or any aromatic substituent or heteroaromatic substituent selected from any aromatic ring or heteroaromatic ring formed by the above two or more adjacent substituents, where the covalent ring can constitute identical or different substructures of two or more structures of chemical formula DABNA-I that share the ring (i.e., the covalent ring may be, for example, ring C' of two structures of chemical formula DABNA-I selectively contained in the emitter, or the covalent ring may be, for example, ring B' of one structure of chemical formula DABNA-I and ring C' of the other structure selectively contained in the emitter). Here, selectively R DABNA-1 , R DABNA-2 , R DABNA-3 , R DABNA-4 , R DABNA-5 and R DABNA-6 At least one of these is replaced by a bond to a further chemical entity of the chemical formula DABNA-I, and / or selectively R DABNA-1 , R DABNA-2 , R DABNA-3 , R DABNA-4 , R DABNA-5 and R DABNA-6At least one hydrogen atom in any one of these is replaced by a bond to a further chemical entity of the chemical formula DABNA-I.
[0385] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, one or more small FWHM emitters S B At least one of them contains a structure with the chemical formula DABNA-I.
[0386] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, each small FWHM emitter S B This includes the structure represented by the chemical formula DABNA-I.
[0387] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, one or more small FWHM emitters S B At least one of these is composed of a structure with the chemical formula DABNA-I.
[0388] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, each small FWHM emitter S B It is composed of a structure with the chemical formula DABNA-I.
[0389] In a preferred embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B It contains or consists of a structure with the chemical formula DABNA-I, and A', B' and All of the C' atoms are aromatic rings (i.e., all are benzene rings) each having six ring atoms.
[0390] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I, Y aand Y b They are independent of each other, NR DABNA-3 O, S, C(R DABNA-3 )2 and Si(R DABNA-3 ) Selected from 2.
[0391] In a preferred embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I, Y a and Y b They are independent of each other, NR DABNA-3 Selected from O and S.
[0392] In a more preferred embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I, Y a and Y b They are independent of each other, NR DABNA-3 And selected from O.
[0393] In a particularly preferred embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I, Y a and Y b Both are NR DABNA-3 That is the case.
[0394] In a particularly preferred embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I, Y a and Y b They are identical and independent of each other, and both are NRDABNA-3 That is the case.
[0395] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more M small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-1 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) DABNA-2 )2, OR DABNA-2 , SR DABNA-2 , Si(R DABNA-2 )3, CF3, CN, F, C1-C5 alkyl, This selectively involves one or more substituents R DABNA-2 Replaced by, C1-C5 alkoxy, This selectively involves one or more substituents R DABNA-2 Replaced by, C1-C5 thioalkoxy, This selectively involves one or more substituents R DABNA-2 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-2 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-2 Replaced by, R DABNA-2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) DABNA-6 )2, OR DABNA-6 , SR DABNA-6 , Si(R DABNA-6 )3, CF3, CN, F, C1-C5 alkyl, This selectively involves one or more substituents R DABNA-6 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-6 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, R DABNA-1 and R DABNA-2 Two or more adjacent substituents selected from the above selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems fused to adjacent rings A', B', or C', where the selectively formed fused ring systems (i.e., each ring A', B', or C' and the additional ring selectively fused to it) contain a total of 8 to 30 ring atoms.
[0396] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-1 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) DABNA-2 )2, OR DABNA-2 , SR DABNA-2 , Si(R DABNA-2 )3, C1-C5 alkyl, This selectively involves one or more substituents R DABNA-2 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-2 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-2 Replaced by, R DABNA-2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) DABNA-6)2, OR DABNA-6 , SR DABNA-6 , Si(R DABNA-6 )3, CF3, CN, F, C1-C5 alkyl, This selectively involves one or more substituents R DABNA-6 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-6 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, R DABNA-1 and R DABNA-2 Two or more adjacent substituents selected from the above selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems fused to adjacent rings A', B', or C', where the selectively formed fused ring systems (i.e., each ring A', B', or C' and the additional ring selectively fused to it) contain a total of 8 to 30 ring atoms.
[0397] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-1 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) DABNA-2 )2, OR DABNA-2 , SR DABNA-2 , C1-C5 alkyl, This selectively involves one or more substituents R DABNA-2 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-2 Replaced by, C3-C 17Heteroaryl, This selectively involves one or more substituents R DABNA-2 Replaced by, R DABNA-2 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, OPh, CN, Me, i Pr, t Bu, Si(Me)3, Ph, This selectively involves one or more substituents R DABNA-6 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-6 Replaced by, Here, two or more adjacent R DABNA-1 These rings form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems condensed to adjacent rings A', B', or C', where the selectively formed fused ring systems (i.e., each ring A', B', or C' and the additional ring selectively condensed to it) contain a total of 8 to 30 ring atoms.
[0398] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-1 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, OPh, Me, i Pr, t Bu, Si(Me)3, Ph, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced with Bu, Ph, or CN C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced with Bu, Ph, or CN Here, two or more adjacent substituents R DABNA-1 The rings selectively condense to adjacent rings A', B', or C' to form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, where each selectively formed ring system (i.e., each ring A', B', or C' and the additional ring selectively condensed to it) contains a total of 8 to 30 ring atoms.
[0399] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-1 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, Me, i Pr, t Bu, Ph, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced with Bu, Ph, or CN Carbazolyl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced with Bu, Ph, or CN Triazinyl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced with Bu, Ph, or CN Pyrimidinyl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, tReplaced with Bu, Ph, or CN Pyridinyl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced with Bu, Ph, or CN Here, two or more adjacent substituents R DABNA-1 The rings selectively condense to adjacent rings A', B', or C' to form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, where each selectively formed ring system (i.e., each ring A', B', or C' and the additional ring selectively condensed to it) contains a total of 8 to 30 ring atoms.
[0400] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I, and R DABNA-1 and R DABNA-2 The adjacent substituents selected from do not form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems condensed on the adjacent ring A', B', or C'.
[0401] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, C1-C4 alkyl, This selectively involves one or more substituents R DABNA-4 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-4 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-4 Replaced by, R DABNA-4 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) DABNA-5 )2, OR DABNA-5 , SR DABNA-5 Si(C1-C5 alkyl)3, CF3, CN, F, C1-C5 alkyl, This selectively involves one or more substituents R DABNA-5 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-5 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-5 Replaced by, R DABNA-5 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, OPh, Si(Me)3, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced by Bu, Ph, or CN C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced by Bu, Ph, or CN Here, R DABNA-3 , R DABNA-4 and R DABNA-5Two or more adjacent substituents selected from the set selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems, where the selectively formed ring systems contain a total of 8 to 30 ring atoms.
[0402] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, C1-C4 alkyl, This selectively involves one or more substituents R DABNA-4 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-4 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-4 Replaced by, R DABNA-4 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(Ph)2, OPh, Si(Me)3, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced by Bu, Ph, or CN C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr,t Replaced by Bu, Ph, or CN Here, R DABNA-3 and R DABNA-4 Two or more adjacent substituents selected from the set do not form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with respect to each other.
[0403] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, C1-C4 alkyl, This selectively involves one or more substituents R DABNA-4 Replaced by, C6-C 18 Ariel, This selectively involves one or more substituents R DABNA-4 Replaced by, C3-C 17 Heteroaryl, This selectively involves one or more substituents R DABNA-4 Replaced by, R DABNA-4 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced by Bu, Ph, or CN C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me,i Pr, t Replaced by Bu, Ph, or CN Here, R DABNA-3 and R DABNA-4 Two or more adjacent substituents selected from the set do not form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with respect to each other.
[0404] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced by Bu, Ph, or CN Here, R DABNA-3 Two or more adjacent substituents selected from the set do not form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with respect to each other.
[0405] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-3 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, Me, i Pr, t Bu, and Ph, Here, one or more hydrogen atoms are selectively and independently of each other, including deuterium, Me, i Pr, t Replaced by Bu, Ph, or CN Here, R DABNA-3 Two or more adjacent substituents selected from the set do not form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with respect to each other.
[0406] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-6 In each case, the following groups are selected independently of each other: Hydrogen, deuterium, OPh (Ph=phenyl), SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, Ph, CN, CF3, or F. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively identified independently as deuterium, CN, CF3, F, and C1. -C5 alkyl, SiMe3, SiPh3 or C6-C 18 Replaced with aryl, C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, CF3, F, C1-C5 alkyl, SiMe3, SiPh3, or C6-C 18 Replaced with aryl, N(C6-C 18 Ariel) 2, N(C3-C 17 Heteroaryl)2, and N(C3-C 17 (Heteroaryl)(C6-C 18 Ariel).
[0407] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-6 In each case, the following groups are selected independently of each other: Hydrogen, deuterium, N(Ph)2, OPh (Ph=phenyl), SPh, CF3, CN, F, Si(Me)3, Si(Ph)3, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, Ph, CN, CF3, or F. C6-C 18 Ariel, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, CF3, F, Me, i Pr, t Replaced with Bu, SiMe3, SiPh3, or Ph, C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently deuterium, CN, CF3, F, Me, i Pr, t It is replaced with Bu, SiMe3, SiPh3, or Ph.
[0408] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-6 In each case, the following groups are selected independently of each other: Hydrogen, deuterium, N(Ph)2, CN, F, Me, i Pr, t Bu, Ph, Here, one or more hydrogen atoms are selectively and independently of deuterium, CN, Me,i Pr, t Replaced with Bu or Ph, C3-C 17 Heteroaryl, Here, one or more hydrogen atoms are selectively and independently of deuterium, CN, Me, i Pr, t It will be replaced with Bu or Ph.
[0409] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B This includes or consists of a structure with the chemical formula DABNA-I. R DABNA-6 In each case, the following groups are selected independently of each other: Hydrogen, deuterium, Me, i Pr, t Bu, Ph, Here, one or more hydrogen atoms are selectively and independently of deuterium, Me, i Pr, t Replaced by Bu or Ph.
[0410] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B is, The structure includes or consists of the structure according to the scientific formula DABNA-I, Y a and / or Y b NR DABNA-3 , C(R DABNA-3 )2, Si(R DABNA-3 )2 or BR DABNA-3 If so, one or two substituents R DABNA-3 This is one or two adjacent rings A' and B'(Y a =NR DABNA-3 , C(R DABNA-3 )2, Si(R DABNA-3 )2 or BR DABNA-3 In the case of A' and C' (Y b=NR DABNA-3 , C(R DABNA-3 )2, Si(R DABNA-3 )2 or BR DABNA-3 It does not combine with ).
[0411] In one embodiment, in the context of the present invention, a small FWHM emitter S B These are selectively polymers (e.g., dimers) of the aforementioned chemical formula DABNA-I, meaning that their structures contain one or more subunits, each having the structure of chemical formula DABNA-I. In this case, those skilled in the art will understand that two or more subunits of chemical formula DABNA-I are, for example, bondable and preferably condensable (i.e., sharing at least one bond, where there are no further substituents bonded to the atoms forming that bond). Furthermore, two or more subunits may share at least one, preferably exactly one, aromatic or heteroaromatic ring. This is, for example, in the small FWHM emitter S B This means that each of these contains two or more subunits having the structure of the chemical formula DABNA-I, where the two subunits share one aromatic ring or heteroaromatic ring (i.e., each ring is part of the two subunits). As a result, each of the polymer (e.g., dimer) emitters S B This has only one covalent ring and does not contain two whole subunits with the chemical formula DABNA-I. Nevertheless, those skilled in the art will understand that in this application, the emitter is still considered a polymer of the chemical formula DABNA-I (for example, a dimer if it contains two subunits having the structure of the chemical formula DABNA-I). The same applies to polymers sharing one or more rings. Preferably, the polymer is a dimer containing two subunits, each having the structure of the chemical formula DABNA-I.
[0412] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, in each small FWHM emitter S BAs mentioned above, it is a dimer of the chemical formula DABNA-I, which means that the emitter contains two subunits, each having a structure according to the chemical formula DABNA-I.
[0413] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S B It comprises or consists of two or more structures (i.e., subunits) with the chemical formula DABNA-I, preferably exactly two.
[0414] Here, these subunits share at least one, preferably exactly one, aromatic or heteroaromatic ring (i.e., the ring may be part of two structures of the chemical formula DABNA-I), where the covalent ring may be any one of rings A', B', and C' of the chemical formula DABNA-I, R DABNA-1 , R DABNA-2 , R DABNA-3 , R DABNA-4 , R DABNA-5 and R DABNA-6 , especially R DABNA-3 The covalent ring may be any aromatic substituent or heteroaromatic substituent selected from the above, or any aromatic ring or heteroaromatic ring formed by two or more adjacent substituents as described above, where the covalent ring can constitute identical or different substructures of two or more structures of the chemical formula DABNA-I that share the ring (i.e., the covalent ring may be, for example, ring C' of two structures of the chemical formula DABNA-I selectively contained in the emitter, or the covalent ring may be, for example, ring B' of one structure of the chemical formula DABNA-I and ring C' of the other structure selectively contained in the emitter).
[0415] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, at least one, preferably, one or more small FWHM emitters S BIt contains or consists of two or more structures (i.e., subunits) with the chemical formula DABNA-I, preferably exactly two. Here, R DABNA-1 , R DABNA-2 , R DABNA-3 , R DABNA-4 , R DABNA-5 and R DABNA-6 At least one of these is replaced by a bond to a further chemical entity of the chemical formula DABNA-I, and / or 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 one of these is replaced by a bond to a further chemical entity of the chemical formula DABNA-I.
[0416] The small FWHM emitter S according to the present invention B A non-limiting example of an emitter containing or composed of a structure with the chemical formula DABNA-I that can be used as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0417] In the context of the present invention, small FWHM emitter S B The emitter groups that can be used are emitters containing or composed of the structure shown in the following chemical formula BNE-1: [ka] ...Chemical formula BNE-1
[0418] Here, c and d are both integers, independently selected from 0 and 1. e and f are both integers, chosen from 0 and 1, where e and f are (always) identical (i.e., both are 0 or both are 1). g and h are both integers, chosen from 0 and 1, where g and h are (always) identical (i.e., both are 0 or both are 1). If d is 0, then both e and f are 1, and if d is 1, then both e and f are 0. If c is 0, then both g and h are 1, and if c is 1, then both g and h are 0. V 1 It is nitrogen (N) and CR BNE-V Selected from, V 2 It is nitrogen (N) and CR BNE-I Selected from, X 3 This is direct bonding, CRBNE-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 Selected from the group consisting of S, S(O), and S(O)2, Y 2 This is direct bonding, 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’ Selected from the group consisting of S, S(O), and S(O)2, 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 is independently selected from the following groups: 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, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 CONRBNE-5 Replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-d , R BNE-d’ and R BNE-e These are selected independently from the following groups: 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, This is because it has one or more substituents R BNE-a It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R BNE-a It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R BNE-a It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R BNE-a It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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-5Replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R BNE-a It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-a It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-a It is selectively replaced by, R BNE-a In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C40 Alkinil, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-5 In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 Replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-6 It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-6 It is selectively replaced by, R BNE-6 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, Ph, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkenyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkynyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C6-C 18 Ariel, This is selectively substituted with one or more C1-C5 alkyl substituents, C2-C 17 Heteroaryl, This is selectively substituted with one or more C1-C5 alkyl substituents, N(C6-C 18 Ariel) 2, N(C2-C 17 Heteroaryl)2, and N(C2-C 17 (Heteroaryl)(C6-C 18 Ariel), Here, R BNE-III and R BNE-e It selectively binds to form a single bond directly. Here, substituent R BNE-a , R BNE-d , R BNE-d’ , R BNE-e , R BNE-3’ , R BNE-4’ and R BNE-5 Two or more of these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, 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 these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, two or more structures of chemical formula BNE-1 are selectively joined to each other, preferably condensed by sharing at least one, more preferably exactly one bond. Here, two or more structures of chemical formula BNE-1 are selectively present in the emitter, sharing at least one, preferably exactly one aromatic or heteroaromatic ring (i.e., the ring may be part of two structures of chemical formula BNE-1), which is preferably one of rings a, b, and c' of chemical formula BNE-1, but 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’ The covalent ring may be any aromatic substituent or heteroaromatic substituent selected from the above, or any aromatic ring or heteroaromatic ring formed by two or more substituents as described above, where the covalent ring can constitute identical or different substructures of two or more structures of chemical formula BNE-1 that share the ring (i.e., the covalent ring may be, for example, ring c' of two structures of chemical formula BNE-1 selectively contained in the emitter, or the covalent ring may be, for example, ring b of one structure of chemical formula BNE-1 and ring c' of the other structure selectively contained in the emitter). Here, selectively, 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 or R BNE-d’At least one of these is replaced by a bond to a further chemical entity of chemical formula BNE-1, and / or 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 or R BNE-d’ At least one hydrogen atom in any one of these is replaced by a bond to a further chemical entity of the chemical formula BNE-1.
[0419] In one embodiment of the present invention, in the light-emitting layer B, a small FWHM emitter S B This includes the structure represented by the chemical formula BNE-1.
[0420] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where V 1 CR BNE-V V 2 CR BNE-I That is the case.
[0421] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where V 1 and V 2 Both are nitrogen (N) ru.
[0422] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where V 1 is nitrogen (N), and V 2 CRBNE-I That is the case.
[0423] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where V 1 CR BNE-V V 2 It is nitrogen (N).
[0424] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where both c and d are 0.
[0425] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where c is 0 and d is 1.
[0426] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where c is 1 and d is 0.
[0427] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1, where both c and d are 1.
[0428] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. X 3 This is direct bonding, CR BNE-3 R BNE-4 , C=O, NR BNE-3 O, S, SiR BNE-3 R BNE-4 Selected from a group consisting of, Y 2 This is direct bonding, CR BNE-3’ R BNE-4’ , C=O, NRBNE-3’ O, S, SiR BNE-3’ R BNE-4’ It is selected from the group consisting of the following.
[0429] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. X 3 This is direct bonding, CR BNE-3 R BNE-4 , NR BNE-3 O, S, SiR BNE-3 R BNE-4 Selected from a group consisting of, Y 2 This is direct bonding, CR BNE-3’ R BNE-4’ , NR BNE-3’ O, S, SiR BNE-3’ R BNE-4’ It is selected from a group consisting of the following.
[0430] In one embodiment of the present invention, at least one, preferably, in each light-emitting layer B, one or more small FWHM emitters S B At least one of these, preferably each containing or comprising a structure according to the chemical formula BNE-1, X 3 This is direct bonding, CR BNE-3 R BNE-4 , NR BNE-3 O, S, SiR BNE-3 R BNE-4 Selected from a group consisting of, Y 2 This is a direct bond.
[0431] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. X 3 This is direct coupling or NR BNE-3 And, Y 2 This is a direct bond.
[0432] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. X 3 , NR BNE-3 And, Y 2 This is a direct bond.
[0433] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. 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 is independently selected from the following groups: 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, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40Alkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkinil, This is because it has one or more substituents RBNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-d , R BNE-d’ and R BNE-e These are selected independently from the following groups: Hydrogen, deuterium, CF3, CN, F, Cl, Br, I, C1-C 40 Alkyl, This is because it has one or more substituents R BNE-a It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-a It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-a It is selectively replaced by, R BNE-a In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-5 In each case, the following groups are selected independently from each other: 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, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Alkoxy, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C1-C 40 Thioalkoxy, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkenil, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C2-C 40 Alkinil, This is because it has one or more substituents R BNE-6 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 60 Ariel, This is because it has one or more substituents R BNE-6 It is selectively replaced by and C2-C 57 Heteroaryl, This is because it has one or more substituents R BNE-6 It is selectively replaced by, R BNE-6 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, Ph, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkenyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkynyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C6-C 18 Ariel, This is selectively substituted with one or more C1-C5 alkyl substituents, C2-C 17 Heteroaryl, This is selectively substituted with one or more C1-C5 alkyl substituents, N(C6-C 18 Ariel) 2, N(C2-C 17 Heteroaryl)2, and N(C2-C 17 (Heteroaryl)(C6-C 18 Ariel), Here, R BNE-III and R BNE-e It selectively binds to form a single bond directly. Here, substituent R BNE-a , R BNE-d , R BNE-d’ , RBNE-e , R BNE-3’ , R BNE-4’ and R BNE-5 Two or more of these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, 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 these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, two or more structures of chemical formula BNE-1 are selectively joined to each other, preferably condensed by sharing at least one, more preferably exactly one bond. Here, two or more structures of chemical formula BNE-1 are selectively present in the emitter, sharing at least one, preferably exactly one aromatic or heteroaromatic ring (i.e., the ring may be part of two structures of chemical formula BNE-1), which is preferably one of rings a, b, and c' of chemical formula BNE-1, but 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’The covalent ring may be any aromatic substituent or heteroaromatic substituent selected from the above, or any aromatic ring or heteroaromatic ring formed by two or more substituents as described above, where the covalent ring may constitute identical or different substructures of two or more structures of chemical formula BNE-1 that share the ring (i.e., the covalent ring may be, for example, ring c' of two structures of chemical formula BNE-1 selectively contained in the emitter, or the covalent ring may be, for example, ring b of one structure of chemical formula BNE-1 and ring c' of the other structure selectively contained in the emitter). Here, selectively, 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 or R BNE-d’ At least one of these is replaced by a bond to a further chemical entity of chemical formula BNE-1, and / or selectively, 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 or R BNE-d’ At least one hydrogen atom in any one of these is replaced by a bond to a further chemical entity of the chemical formula BNE-1.
[0434] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. 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 is independently selected from the following groups: Hydrogen, deuterium, N(R) BNE-5 )2, OR BNE-5 , Si(R BNE-5 )3, B(R BNE-5 )2, CF3, CN, F, Cl, Br, I, C1-C 18 Alkyl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 30 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 29 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-d , R BNE-d’ and R BNE-e These are selected independently from the following groups: Hydrogen, deuterium, CF3, CN, F, Cl, Br, I, C1-C 18 Alkyl, This is because it has one or more substituents R BNE-a It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 It is selectively replaced by, C6-C 30 Ariel, This is because it has one or more substituents R BNE-a It is selectively replaced by and C2-C 29 Heteroaryl, This is because it has one or more substituents R BNE-a It is selectively replaced by, R BNE-a In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) BNE-5 )2, OR BNE-5 , Si(R BNE-5 )3, B(R BNE-5 )2, CF3, CN, F, Cl, Br, I, C1-C 18 Alkyl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, Here, one or more non-adjacent CH2 units are 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 CONRBNE-5 It is selectively replaced by, C6-C 30 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 29 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-5 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms selectively and independently become deuterium, CN, CF3, and ta is replaced with F, C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C1-C5 thioalkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkenyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C2-C5 alkynyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C6-C 18 Ariel, This is selectively substituted with one or more C1-C5 alkyl substituents, C2-C 17 Heteroaryl, This is selectively substituted with one or more C1-C5 alkyl substituents, N(C6-C 18 Ariel) 2, N(C2-C 17 Heteroaryl)2, and N(C2-C 17(Heteroaryl)(C6-C 18 Ariel), Here, R BNE-III and R BNE-e It selectively binds to form a single bond directly. Here, substituent R BNE-a , R BNE-d , R BNE-d’ , R BNE-e , R BNE-3’ , R BNE-4’ and R BNE-5 Two or more of these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, 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 these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, two or more structures of chemical formula BNE-1 are selectively joined to each other, preferably condensed by sharing at least one, more preferably exactly one bond. Here, two or more structures of chemical formula BNE-1 are selectively present in the emitter, sharing at least one, preferably exactly one aromatic or heteroaromatic ring (i.e., the ring may be part of two structures of chemical formula BNE-1), which is preferably one of rings a, b, and c' of chemical formula BNE-1, but 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 , RBNE-III , R BNE-IV , R BNE-V , R BNE-a , R BNE-e , R BNE-d and R BNE-d’ The covalent ring may be any aromatic substituent or heteroaromatic substituent selected from the above, or any aromatic ring or heteroaromatic ring formed by two or more substituents as described above, where the covalent ring can constitute identical or different substructures of two or more structures of chemical formula BNE-1 that share the ring (i.e., the covalent ring may be, for example, ring c' of two structures of chemical formula BNE-1 selectively contained in the emitter, or the covalent ring may be, for example, ring b of one structure of chemical formula BNE-1 and ring c' of the other structure selectively contained in the emitter). Here, selectively, 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 or R BNE-d’ at least Another is replaced by bonding to a further chemical entity of chemical formula BNE-1, and / or selectively, 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 or RBNE-d’ At least one hydrogen atom in any one of these is replaced by a bond to a further chemical entity of the chemical formula BNE-1.
[0435] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. 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 is independently selected from the following groups: Hydrogen, deuterium, N(R) BNE-5 )2, OR BNE-5 , Si(R BNE-5 )3, B(R BNE-5 )2, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 17 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-d , R BNE-d’ and R BNE-e These are selected independently from the following groups: Hydrogen, deuterium, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R BNE-a It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R BNE-a It is selectively replaced by and C2-C 17 Heteroaryl, This is because it has one or more substituents R BNE-a It is selectively replaced by, R BNE-a In each case, the following groups are selected independently from each other: Hydrogen, deuterium, N(R) BNE-5 )2, OR BNE-5 , Si(R BNE-5 )3, B(R BNE-5 )2, CF3, CN, F, C1-C5 alkyl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, C6-C 18 Ariel, This is because it has one or more substituents R BNE-5 It is selectively replaced by and C2-C 17 Heteroaryl, This is because it has one or more substituents R BNE-5 It is selectively replaced by, R BNE-5 In each case, the following groups are selected independently from each other: Hydrogen, deuterium, OPh, CF3, CN, F, C1-C5 alkyl, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C1-C5 alkoxy, Here, one or more hydrogen atoms are selectively and independently substituted with deuterium, CN, CF3, or F. C6-C 18 Ariel, This is selectively substituted with one or more C1-C5 alkyl substituents, C2-C 17 Heteroaryl, This is selectively substituted with one or more C1-C5 alkyl substituents, N(C6-C 18 Ariel) 2, N(C2-C 17 Heteroaryl)2, and N(C2-C 17 (Heteroaryl)(C6-C 18 Ariel), Here, R BNE-III and R BNE-e It selectively binds to form a single bond directly. Here, substituent R BNE-a , R BNE-d , R BNE-d’ , R BNE-e , R BNE-3’ , R BNE-4’ and R BNE-5 Two or more of these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, 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 these elements selectively form monocyclic or polycyclic, aliphatic or aromatic or heteroaromatic, carbocyclic or heterocyclic systems with each other. Here, two or more structures of chemical formula BNE-1 are selectively joined to each other, preferably condensed by sharing at least one, more preferably exactly one bond. Here, two or more structures of chemical formula BNE-1 are selectively present in the emitter, sharing at least one, preferably exactly one aromatic or heteroaromatic ring (i.e., the ring may be part of two structures of chemical formula BNE-1), which is preferably one of rings a, b, and c' of chemical formula BNE-1, but R BNE-1 , R BNE-2 , R BNE-1’ , R BNE-2’ , R BNE-3 , R BNE-4 , R BNE-3’ , R BNE-4’ , RBNE-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’ The covalent ring may be any aromatic substituent or heteroaromatic substituent selected from the above, or any aromatic ring or heteroaromatic ring formed by two or more substituents as described above, where the covalent ring can constitute identical or different substructures of two or more structures of chemical formula BNE-1 that share the ring (i.e., the covalent ring may be, for example, ring c' of two structures of chemical formula BNE-1 selectively contained in the emitter, or the covalent ring may be, for example, ring b of one structure of chemical formula BNE-1 and ring c' of the other structure selectively contained in the emitter). Here, selectively, 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 or R BNE-d’ At least one of these is replaced by a bond to a further chemical entity of chemical formula BNE-1, and / or selectively, 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 , RBNE-a , R BNE-e , R BNE-d or R BNE-d’ At least one hydrogen atom in any one of these is replaced by a bond to a further chemical entity of the chemical formula BNE-1.
[0436] In one embodiment of the present invention, a small FWHM emitter S B This includes or consists of a structure with the chemical formula BNE-1. 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 is independent of the others and consist...
Claims
1. An organic electroluminescent element comprising a light-emitting layer B containing the following: (i) Lowest excited singlet state energy level E(S1) E ) and the lowest excited triplet state energy level E(T1 E ) TADF material E B , (ii) Lowest excited singlet state energy level E(S1 S ) and the lowest excited triplet state energy level E(T1 S A small FWHM emitter S has a maximum emission range of 510 nm to 550 nm and emits light with a FWHM width of 0.25 eV or less. B , and (iii) A host material H having a lowest excited singlet state energy level E(S1 H ), and a lowest excited triplet state energy level E(T1 H ). B , Here, the organic electroluminescent element includes an exciton control layer EXL adjacent to the light-emitting layer B, which contains a triplet-triplet annihilation (TTA) material. The exciton management layer EXL includes at least one additional emitter.
2. The organic electroluminescent element according to claim 1, wherein the thickness of the exciton control layer EXL is less than 15 nm.
3. The organic electroluminescent element according to claim 1 or 2, wherein the thickness of the exciton management layer EXL is less than 10 nm.
4. The TTA material comprises the structure represented by the following chemical formula 4, comprising the organic electroluminescent element according to any one of claims 1 to 3: 【Chemistry 1】 ...Chemical formula 4 Here, Each Ar is independently selected from the group consisting of the following: C 6 -C 60 Ariel, C 3 -C 57 Heteroaryls, halogens, and C 1 -C 40 C is selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups. 6 -C 60 Aryl, and C 6 -C 60 Ariel, C 3 -C 57 Heteroaryls, halogens, and C 1 -C 40 C is selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups. 3 -C 57 Heteroaryl, Each A 1 It is independently selected from the group consisting of the following: hydrogen, deuterium, C 6 -C 60 Ariel, C 3 -C 57 Heteroaryls, halogens, and C 1 -C 40 C is selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups. 6 -C 60 Ariel, C 6 -C 60 Ariel, C 3 -C 57 Heteroaryls, halogens, and C 1 -C 40 C is selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups. 3 -C 57 Heteroaryls, and C 6 -C 60 Ariel, C 3 -C 57 Heteroaryls, halogens, and C 1 -C 40 C is selectively substituted with one or more residues selected from the group consisting of (hetero)alkyl groups. 1 -C 40 (Hetero)alkyl.
5. Both the exciton management layer EXL and the emitter of the light-emitting layer B are small FWHM emitters S that emit light with a maximum emission of 510 nm to 550 nm and a FWHM of 0.25 eV or less. B The organic electroluminescent element according to any one of claims 1 to 4.
6. The aforementioned light-emitting layer B is (iv) Lowest excited singlet state energy level E(S1) EET-2 ) and the lowest excited triplet state energy level E(T1 EET-2 An organic electroluminescent element according to any one of claims 1 to 5, further comprising an excitation energy transfer component EET-2 selected from the group consisting of TADF material and phosphorescent material, having ).
7. The organic electroluminescent element according to claim 6, wherein the EET-2 is a phosphorescent material.
8. The aforementioned small FWHM emitter S B The organic electroluminescent element according to any one of claims 1 to 7, which satisfies at least one of the following requirements: (i) Boron (B) containing emitters, which are each small FWHM emitters S B This means that at least one atom in is boron (B), and / or (ii) comprising a polycyclic aromatic or heteroaromatic core structure in which at least two aromatic rings are condensed together.
9. Each TADF material E B teeth, (i) Lowest excited singlet state energy E(S1 E ) and the lowest excited triplet state energy E(T1 E ΔE corresponds to the energy difference with ) ST It is characterized by a value of less than 0.4 eV, (ii) An organic electroluminescent element according to any one of claims 1 to 8, exhibiting a photoluminescence quantum yield (PLQY) greater than 30%.
10. An organic electroluminescent element according to any one of claims 1 to 9, satisfying (13) and (30) below: E(T1) H )>E(D1 E ) (13) E (T1) E )>E(S1 S ) (30).
11. The exciton management layer EXL is located between the light-emitting layer B and the anode of the organic electroluminescent element, according to any one of claims 1 to 10.
12. (i) Deposition of the light-emitting layer B via vacuum deposition, and (ii) The process includes depositing an exciton control layer EXL via vacuum deposition, The above (i) and (ii) are executed sequentially, A method for manufacturing an organic electroluminescent element according to any one of claims 1 to 11, wherein the order of (i) and (ii) above is reversible.
13. A method for generating light, including the following steps: (i) To provide an organic electroluminescent element obtained from any one of claims 1 to 11 or from the method described in claim 12, and (ii) Applying an electric current to the organic electroluminescent element.
14. The light generation method according to claim 13, wherein the light is generated in which the maximum emission of the main emission peak is within a wavelength range of 510 nm to 550 nm.
Citation Information
Patent Citations
Organic electroluminescent device emitting blue light
JP2019204947A
Organic light emitting diode and Organic light emitting display device including the same
KR1020190071971A
Organic light emitting diode and organic light emitting device having the same
US20200194689A1