CN116744710A - Organic electroluminescent material and device - Google Patents

Organic electroluminescent material and device Download PDF

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Publication number
CN116744710A
CN116744710A CN202310234798.5A CN202310234798A CN116744710A CN 116744710 A CN116744710 A CN 116744710A CN 202310234798 A CN202310234798 A CN 202310234798A CN 116744710 A CN116744710 A CN 116744710A
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group
layer
compound
oled
electrode
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N·J·汤普森
T·费利塔姆
F·M·贾拉迪
林春
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Universal Display Corp
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Universal Display Corp
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Abstract

The present application relates to organic electroluminescent materials and devices. There is provided an OLED comprising: a first electrode; a second electrode; a first layer and an emissive layer disposed between the first electrode and the second electrode, wherein the first layer is selected from the group consisting of: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and the first layer comprises a first compound comprising a first element selected from the group consisting of D, F, CN, si, ge, P, B and Se only.

Description

Organic electroluminescent material and device
Cross reference to related applications
The present application claims priority from U.S. 119 (e) to U.S. provisional application No. 63/326,548, U.S. provisional application No. 63/318,269 to 2022, U.S. provisional application No. 63/400,416 to 2022, U.S. provisional application No. 63/329,688 to 2022, U.S. provisional application No. 63/395,173 to 2022, U.S. provisional application No. 63/329,924 to 2022, U.S. provisional application No. 63/401,800 to 2022, U.S. provisional application No. 63/342,198 to 2022, U.S. provisional application No. 63/367,818 to 2022, U.S. provisional application No. 63/329,924 to 2022, U.S. provisional application No. 63/924 to 2022, U.S. provisional application No. 29 to 2022, U.S. provisional application No. 63/342,198 to 2022, and U.S. provisional application No. 63/367,818 to 2022, 5, 7.
Technical Field
The present disclosure relates generally to OLED devices and their use in related electronic devices including consumer products.
Background
Optoelectronic devices utilizing organic materials are becoming increasingly popular for a variety of reasons. Many of the materials used to fabricate the devices are relatively inexpensive, so organic photovoltaic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) may make them more suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.
OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting and backlighting.
One application of phosphorescent emissive molecules is in full color displays. Industry standards for such displays require pixels adapted to emit a particular color (referred to as a "saturated" color). In particular, these standards require saturated red, green and blue pixels. Alternatively, the OLED may be designed to emit white light. In conventional liquid crystal displays, the emission from a white backlight is filtered using an absorbing filter to produce red, green and blue emissions. The same technique can also be used for OLEDs. The white OLED may be a single emissive layer (EML) device or a stacked structure. The colors may be measured using CIE coordinates well known in the art.
Disclosure of Invention
In one aspect, the present disclosure provides an Organic Light Emitting Device (OLED) comprising: a first electrode; a second electrode; a first layer and an emissive layer (EML) disposed between the first electrode and the second electrode, wherein the first layer is selected from the group consisting of: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL); the first layer includes a first compound including a first element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In another aspect, the present disclosure provides a consumer product comprising an OLED as described in the present disclosure.
Drawings
Fig. 1 shows an organic light emitting device.
Fig. 2 shows an inverted organic light emitting device without a separate electron transport layer.
Detailed Description
A. Terminology
Unless otherwise specified, the following terms used herein are defined as follows:
as used herein, the term "organic" includes polymeric materials and small molecule organic materials that can be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and may be substantial in nature. In some cases, the small molecule may include a repeating unit. For example, the use of long chain alkyl groups as substituents does not remove a molecule from the "small molecule" class. Small molecules may also be incorporated into the polymer, for example as pendant groups on the polymer backbone or as part of the backbone. Small molecules can also act as the core of a dendrimer, which consists of a series of chemical shells built on the core. The core moiety of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. Dendrimers may be "small molecules" and all dendrimers currently used in the OLED field are considered small molecules.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed" over "a second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed over" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photosensitive" when it is believed that the ligand contributes directly to the photosensitive properties of the emissive material. When the ligand is considered not to contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary", but the ancillary ligand may alter the properties of the photosensitive ligand.
As used herein, and as will be generally understood by those of skill in the art, if the first energy level is closer to the vacuum energy level, then the first "highest occupied molecular orbital" (Highest Occupied Molecular Orbital, HOMO) or "lowest unoccupied molecular orbital" (Lowest Unoccupied Molecular Orbital, LUMO) energy level is "greater than" or "higher than" the second HOMO or LUMO energy level. Since Ionization Potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO level corresponds to an IP with a smaller absolute value (less negative). Similarly, a higher LUMO energy level corresponds to an Electron Affinity (EA) with a smaller absolute value (less negative EA). On a conventional energy level diagram with vacuum energy level on top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. The "higher" HOMO or LUMO energy level appears closer to the top of this figure than the "lower" HOMO or LUMO energy level.
As used herein, and as will be generally understood by those of skill in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Since work function is typically measured as a negative number relative to the vacuum level, this means that the "higher" work function is more negative (more negative). On a conventional energy level diagram with the vacuum energy level on top, a "higher" work function is illustrated as being farther from the vacuum energy level in a downward direction. Thus, the definition of HOMO and LUMO energy levels follows a different rule than work function.
The terms "halo", "halogen" and "halo" are used interchangeably and refer to fluoro, chloro, bromo and iodo.
The term "acyl" refers to a substituted carbonyl (C (O) -R s )。
The term "ester" refers to a substituted oxycarbonyl (-O-C (O) -R) s or-C (O) -O-R s ) A group.
The term "ether" means-OR s A group.
The terms "thio" or "thioether" are used interchangeably and refer to-SR s A group.
The term "selenoalkyl" refers to-SeR s A group.
The term "sulfinyl" refers to-S (O) -R s A group.
The term "sulfonyl" refers to-SO 2 -R s A group.
The term "phosphino" refers to-P (R s ) 3 A group wherein each R s May be the same or different.
The term "silane group" means-Si (R s ) 3 A group wherein each R s May be the same or different.
The term "germyl" refers to-Ge (R s ) 3 A group wherein each R s May be the same or different.
The term "borane" refers to-B (R s ) 2 A group or Lewis addition product-B (R) s ) 3 A group, wherein R is s May be the same or different.
In each of the above, R s May be hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. Preferred R s Selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
The term "alkyl" refers to and includes straight and branched chain alkyl groups. Preferred alkyl groups are those containing from one to fifteen carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2-dimethylpropyl, and the like. In addition, alkyl groups may be optionally substituted.
The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo [3.1.1] heptyl, spiro [4.5] decyl, spiro [5.5] undecyl, adamantyl, and the like. In addition, cycloalkyl groups may be optionally substituted.
The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, si and Se, preferably O, S or N. In addition, heteroalkyl or heterocycloalkyl groups may be optionally substituted.
The term "alkenyl" refers to and includes both straight and branched alkenyl groups. Alkenyl is essentially an alkyl group comprising at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl is essentially cycloalkyl including at least one carbon-carbon double bond in the cycloalkyl ring. The term "heteroalkenyl" as used herein refers to an alkenyl group having at least one carbon atom replaced with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, si and Se, preferably O, S or N. Preferred alkenyl, cycloalkenyl or heteroalkenyl groups are those containing from two to fifteen carbon atoms. In addition, alkenyl, cycloalkenyl, or heteroalkenyl groups may be optionally substituted.
The term "alkynyl" refers to and includes both straight and branched chain alkynyl groups. Alkynyl is essentially an alkyl group that includes at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those containing from two to fifteen carbon atoms. In addition, alkynyl groups may be optionally substituted.
The term "aralkyl" or "arylalkyl" is used interchangeably and refers to an alkyl group substituted with an aryl group. In addition, aralkyl groups may be optionally substituted.
The term "heterocyclyl" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, si and Se, preferably O, S or N. Aromatic heterocyclic groups may be used interchangeably with heteroaryl. Preferred non-aromatic heterocyclic groups are heterocyclic groups containing 3 to 7 ring atoms including at least one heteroatom and include cyclic amines such as morpholinyl, piperidinyl, pyrrolidinyl, and the like, and cyclic ethers/sulfides such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. In addition, the heterocyclic group may be optionally substituted.
The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic ring may have two or more rings in common in which two carbons are two adjoining rings (the rings being "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. Preferred aryl groups are those containing from six to thirty carbon atoms, preferably from six to twenty carbon atoms, more preferably from six to twelve carbon atoms. Particularly preferred are aryl groups having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups may be optionally substituted.
The term "heteroaryl" refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom. Heteroatoms include, but are not limited to O, S, N, P, B, si and Se. In many cases O, S or N are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. The heteropolycyclic ring system may have two or more rings in which two atoms are common to two adjoining rings (the rings being "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. The heteropolycyclic aromatic ring system may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, diazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene (xanthene), acridine, phenazine, phenothiazine, phenoxazine, benzofurandipyridine, benzothiophene pyridine, thienodipyridine, benzoselenophene dipyridine, dibenzofuran, dibenzoselenium, carbazole, indolocarbazole, benzimidazole, triazine, 1, 2-borazine, 1-boron-nitrogen, 1-nitrogen, 4-boron-nitrogen, boron-nitrogen-like compounds, and the like. In addition, heteroaryl groups may be optionally substituted.
Of the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and their respective corresponding aza analogues, are of particular interest.
The terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclyl, aryl, and heteroaryl as used herein are independently unsubstituted or independently substituted with one or more common substituents.
In many cases, the typical substituents are selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, selenkyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In some cases, preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, germyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof.
In some cases, more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, thio, and combinations thereof.
In other cases, the most preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
The terms "substituted" and "substituted" refer to substituents other than H bonded to the relevant position, such as carbon or nitrogen. For example, when R 1 When single substitution is represented, then one R 1 It must not be H (i.e., substitution). Similarly, when R 1 When two are substituted, two R 1 It must not be H. Similarly, when R 1 R represents zero or no substitution 1 For example, it may be hydrogen of available valence number for the ring atom, such as carbon atom of benzene and nitrogen atom of pyrrole, or for having a valence number ofThe ring atoms of fully saturated valences represent no nitrogen atoms, for example in pyridine. The maximum number of substitutions possible in the ring structure will depend on the total number of available valences in the ring atom.
As used herein, "combination thereof" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl may combine to form a haloalkyl substituent; and halogen, alkyl and aryl may combine to form a haloaralkyl. In one example, the term substitution includes a combination of two to four of the listed groups. In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms other than hydrogen or deuterium, or combinations comprising up to forty atoms other than hydrogen or deuterium, or combinations comprising up to thirty atoms other than hydrogen or deuterium. In many cases, a preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium.
The term "aza" in the fragments described herein, i.e., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic ring may be replaced with a nitrogen atom, for example and without limitation, aza-triphenylene encompasses dibenzo [ f, H ] quinoxaline and dibenzo [ f, H ] quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by those of ordinary skill in the art, and all such analogs are intended to be encompassed by the terms as set forth herein.
As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. patent No. 8,557,400, patent publication No. WO 2006/095951, and U.S. patent application publication No. US 2011/0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Yan Ming (Ming Yan) et al, tetrahedron 2015,71,1425-30 and Azrote (Atzrodt) et al, germany application chemistry (Angew. Chem. Int. Ed.) (reviewed) 2007,46,7744-65, which is incorporated by reference in its entirety, describes the deuteration of methylene hydrogen in benzylamine and the efficient pathway of replacement of aromatic ring hydrogen with deuterium, respectively.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or linking fragments are considered equivalent.
In some cases, a pair of adjacent substituents may optionally be joined or fused into a ring. Preferred rings are five-, six-, or seven-membered carbocycles or heterocycles, including both cases where a portion of the ring formed by the pair of substituents is saturated and a portion of the ring formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that the two substituents involved may be located next to each other on the same ring, or on two adjacent rings having two nearest available substitutable positions (e.g., the 2, 2' positions in biphenyl or the 1, 8 positions in naphthalene) so long as they can form a stable fused ring system.
The layers, materials, regions and colors of light emitted by the device may be described herein with reference thereto. In general, as used herein, an emissive region described as producing a particular color of light may include one or more emissive layers disposed on top of each other in a stacked manner.
As used herein, a "red" layer, material, region or device refers to a layer that emits light in the range of about 580-700nm or whose emission spectrum has the highest peak in that region. Similarly, a "green" layer, material, region or device refers to one that emits or has an emission spectrum with a peak wavelength in the range of about 500-600 nm; "blue" layer, material or device refers to one that emits or has an emission spectrum with a peak wavelength in the range of about 400-500 nm; and a "yellow" layer, material, region or device refers to one having an emission spectrum with a peak wavelength in the range of about 540-600 nm. In some arrangements, separate regions, layers, materials, regions, or devices may provide separate "deep blue" and "light blue" light. As used herein, in an arrangement that provides separate "light blue" and "dark blue" components, a "dark blue" component refers to a component having a peak emission wavelength that is at least about 4nm less than the peak emission wavelength of the "light blue" component. Typically, the peak emission wavelength of the "light blue" component is in the range of about 465-500nm, and the peak emission wavelength of the "dark blue" component is in the range of about 400-470nm, although these ranges may vary for some configurations. Similarly, a color shifting layer refers to a layer that converts or modifies light of another color into light having a wavelength designated for that color. For example, a "red" filter refers to a filter that forms light having a wavelength in the range of about 580-700 nm. In general, there are two types of color shifting layers: a color filter to modify the spectrum by removing unwanted wavelengths of light, and a color shifting layer to convert higher energy photons to lower energy. "color" component refers to a component that, when activated or in use, generates or otherwise emits light having a particular color as previously described. For example, "a first emission region of a first color" and "a second emission region of a second color different from the first color" describe two emission regions that emit two different colors as previously described when activated within a device.
As used herein, emissive materials, layers, and regions may be distinguished from one another and from other structures based on light initially produced by the materials, layers, or regions, rather than light ultimately emitted by the same or different structures. Initial light generation is typically the result of a change in energy level that results in photon emission. For example, the organic emissive material may initially generate blue light, which may be converted to red or green light by a color filter, quantum dot, or other structure, such that the complete emissive stack or subpixel emits red or green light. In this case, the initial emissive material or layer may be referred to as the "blue" component, even though the subpixels are of the "red" or "green" components.
In some cases, it may be preferable to describe the color of components, such as the emissive area, sub-pixels, color shifting layers, etc., according to 1931CIE coordinates. For example, the yellow emissive material may have multiple peak emission wavelengths, one in or near the edge of the "green" region, and one within or near the edge of the "red" region, as previously described. Thus, as used herein, each color item also corresponds to a shape in the 1931CIE coordinate color space. The shape in the 1931CIE color space is constructed by following a trajectory between two color points and any other internal points. For example, the internal shape parameters of red, green, blue, and yellow may be defined as follows:
Further details regarding OLEDs and the definitions described above can be found in U.S. patent No. 7,279,704, which is incorporated herein by reference in its entirety.
B. OLED and device of the present disclosure
In one aspect, the present disclosure provides an Organic Light Emitting Device (OLED) embodiment a comprising: a first electrode; a second electrode; a first layer and an emissive layer (EML) disposed between the first electrode and the second electrode, wherein the first layer is selected from the group consisting of: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL); the first layer includes a first compound including a first element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the first compound further comprises a second element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and wherein the first element is different from the second element.
In some embodiments, the first compound further comprises a third element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and wherein the third element is different from the first element and the second element. In some embodiments, the first compound further comprises a fourth element, wherein the fourth element is selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and wherein the fourth element is different from the first element, the second element, and the third element.
In some embodiments, the first layer is selected from the group consisting of a HIL, an HTL, and an EBL; wherein the first element is selected from the group consisting of D, si, ge, P and Se.
In some embodiments, the first layer is selected from the group consisting of a HIL, an HTL, and an EBL; wherein each of the first element and the second element is independently selected from the group consisting of D, si, ge, P and Se.
In some embodiments, the first layer is selected from the group consisting of a HIL, an HTL, and an EBL; wherein each of the first element, the second element, and the third element is independently selected from the group consisting of D, si, ge, P and Se.
In some embodiments, the first layer is selected from the group consisting of HBL, ETL, and EIL; wherein the first element is selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the first layer is selected from the group consisting of HBL, ETL, and EIL; wherein each of the first element and the second element is independently selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the first layer is selected from the group consisting of HBL, ETL, and EIL; wherein each of the first element, the second element, and the third element is independently selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the EML comprises a second compound comprising at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the EML comprises a second compound comprising at least two different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the EML comprises a second compound comprising at least three different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the OLED further comprises a second layer disposed between the first electrode and the second electrode; wherein the second layer is selected from the group consisting of: HIL, HTL, EBL, HBL, ETL and EIL; the second layer is a different type of layer than the first layer; the second layer comprises a second compound; wherein the second compound comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some of the above embodiments, the second compound comprises at least two different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the second compound comprises at least three different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, chemical group a comprises a first element, chemical group B comprises a second element, chemical group C comprises a third element, and chemical group D comprises a fourth element. In some embodiments, chemical group a is attached to an unsaturated carbon atom. In some embodiments, chemical group a is attached to a saturated carbon atom. In some embodiments, chemical group a is attached to a Si or Ge atom. In some embodiments, the first compound comprises a first ring, wherein the chemical group a is attached to the first ring.
In some embodiments, chemical group a and chemical group B are attached to the first ring. In some embodiments, the first compound comprises a first fused ring system, and chemical group a and chemical group B are attached to the first fused ring system. In some embodiments, the first compound further comprises a second ring, and chemical group a is attached to the first ring, and chemical group B is attached to the second ring; wherein the first loop is different from the second loop. In some embodiments, chemical group a is attached to a first fused ring system and chemical group B is attached to a second fused ring system; wherein the first fused ring system is different from the second fused ring system. In some embodiments, chemical groups a and B are attached to the same carbon atom, the same Si atom, or the same Ge atom. In some embodiments, chemical group a is attached to an unsaturated carbon atom and chemical group B is attached to an unsaturated carbon atom. In some embodiments, chemical group a is attached to an unsaturated carbon atom and chemical group B is attached to a saturated carbon atom. In some embodiments, chemical group a is attached to a saturated carbon atom and chemical group B is attached to a saturated carbon atom.
In some embodiments, chemical group C is attached to an unsaturated carbon atom. In some embodiments, chemical group C is attached to a saturated carbon atom. In some embodiments, the chemical group C is attached to a Si or Ge atom. In some embodiments, chemical group C is attached to the first ring.
In some of the above embodiments, each of the first, second, and third rings may be independently selected from the group consisting of: benzene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, thiophene, pyrrole, oxazole, thiazole, imidazole, pyrazole, azaborane, borazine, and various carbenes derived therefrom.
In some of the above embodiments, each of the first, second, and third ring systems may be independently selected from the group consisting of: triphenylene, tetrabenzenes, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, dibenzothiophene, dibenzofuran, dibenzoselenophene, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranpyridine, furandipyridine, benzothiophenopyridine, thienodipyridine, benzoselenophenopyridine, seleno-bipyridine, benzazenoborane, benzoborazine, dibenzoborazine and dibenzoborazine.
In some embodiments, the first compound is a non-metal containing compound.
In some embodiments, the first compound is a metal-containing compound.
In some embodiments, the first compound is a hole transporting compound.
In some embodiments, the first compound is an electron transporting compound.
In some embodiments, the EML further comprises a first emitter. In some embodiments, the first emitter may be a phosphorescent or fluorescent emitter. Phosphorescence generally refers to photon emission with a change in electron spin, i.e., the initial and final states of the emission have different diversity, such as from T 1 To S 0 Status of the device. Ir and Pt complexes currently widely used in OLEDs belong to the phosphorescent emitters. In some embodiments, such exciplex may also emit phosphorescence if exciplex formation involves triplet emitters. On the other hand, fluorescent emitters generally refer to photon emission without changing the spin of electrons, e.g. from S 1 To S 0 Status of the device. The fluorescent emitter may be a delayed fluorescent or non-delayed fluorescent emitter. Depending on the spin state, the fluorescent emitter may be a singlet emitter or a doublet emitter or other multiple state emitter. It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. There are two types of delayed fluorescence, namely P-type and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA). On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the number of thermal population between triplet and singlet excited states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). The type E delayed fluorescence feature may be found in an exciplex system or in a single compound. Without being bound by theory, it is believed that TADF needs to have a singlet-triplet energy gap (Δe) of less than or equal to 300, 250, 200, 150, 100, or 50meV S-T ) A compound or exciplex of (a). There are two main types of TADF emitters, one is known as donor-acceptor TADF and the other is known as Multiple Resonance (MR) TADF. Typically, a donor-acceptor single compound is constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) and an electron acceptor moiety (e.g., containing an N six-membered aromatic ring). Can transport holes atA donor-acceptor exciplex is formed between the compound and the electron transport compound. Examples of MR-TADF include highly conjugated boron-containing compounds. In some embodiments, the reverse intersystem crossing (cross) time from T1 to S1 of the delayed fluorescence emission at 293K is less than or equal to 10 microseconds. In some embodiments, this time may be greater than 10 microseconds and less than 100 microseconds.
In some embodiments, the first emitter is capable of emitting light from a triplet excited state to a singlet ground state in the OLED at room temperature.
In some embodiments, the first emitter is a metal coordination complex having a metal-carbon bond.
In some embodiments, the first emitter is a metal coordination complex having a metal-nitrogen bond.
In some embodiments, the first emitter is a metal coordination complex having a metal-oxygen bond.
In some embodiments, the metal is selected from the group consisting of: ir, rh, re, ru, os, pt, pd, au, ag and Cu.
In some embodiments, the metal is Ir.
In some embodiments, the metal is Pt.
In some embodiments, the first emitter has the formula M (L 1 ) x (L 2 ) y (L 3 ) z The method comprises the steps of carrying out a first treatment on the surface of the Wherein L is 1 、L 2 And L 3 May be the same or different;
wherein x is 1, 2 or 3;
wherein y is 0, 1 or 2;
wherein z is 0, 1 or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein L is 1 Selected from the group consisting of the structures of the following list 1:
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wherein L is 2 And L 3 Independently selected from the group consisting of the structures of the following list 2:
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t is selected from the group consisting of B, al, ga and In;
wherein K is 1 ' is a direct bond or is selected from NR e 、PR e O, S and Se;
wherein each Y 1 To Y 13 Independently selected from the group consisting of carbon and nitrogen;
wherein Y' is selected from the group consisting of: b R e 、N R e 、P R e 、O、S、Se、C＝O、S＝O、SO 2 、CR e R f 、SiR e R f And GeR e R f ；
R e And R is f May be fused or joined to form a ring;
wherein each R is a 、R b 、R c And R is d May independently represent a single to the maximum number of possible substitutions or no substitution;
wherein the method comprises the steps ofEach R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d 、R e And R is f Independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and
wherein R is a1 、R b1 、R c1 、R d1 、R a 、R b 、R c And R is d Any two adjacent substituents of (a) may be fused or joined to form a ring or to form a multidentate ligand.
In the presence of a catalyst having the formula M (L 1 ) x (L 2 ) y (L 3 ) z In some embodiments of the heteroleptic compounds of (2), ligand L 1 Having a first substituent R I Wherein the first substituent R I Having a first atom a-I which is a ligand L 1 Is furthest from the metal M among all atoms in the group. In addition, ligand L 2 Having a second substituent R if present II Wherein the second substituent R II a-II at ligand L 2 Is furthest from the metal M among all atoms of (a). In addition, ligand L 3 Having a third substituent R if present III Wherein the third substituent R III The first atom a-III in the ligand L 3 Is furthest from the metal M among all atoms of (a).
In such heteroleptic compounds, the vector V can be defined D1 、V D2 And V D3 It is defined as follows. V (V) D1 Represents the direction from the metal M to the first atom a-I, and the vector V D1 Value D of (2) 1 Represents a metal M and a first substituent R I a-I, the first atom a-I of the group. V (V) D2 Represents the direction from the metal M to the first atom a-II and the vector V D2 Value D of (2) 2 Represents a metal M and a second substituent R II a-II, the first atom a-II. V (V) D3 Represents the direction from the metal M to the first atom a-III, and the vector V D3 Value D of (2) 3 Represents a metal M and a third substituent R III a-III, and a linear distance between the first atoms a-III.
In such heteroleptic compounds, spheres are defined having a radius R centered at the metal M and the radius R is that which allows the spheres to enclose compounds in which not substituents R I 、R II And R is III A minimum radius of all atoms of a portion of (a); and wherein D 1 、D 2 And D 3 At least one of which is larger than the radius r by at leastIn some embodiments, D 1 、D 2 And D 3 At least 2.9, 3.0, 4.3, 4.4, 5.2, 5.9, 7.3, 8.8, 10.3, 13.1, 17.6 or +.>
In some embodiments of such heteroleptic compounds, the compound has a transition dipole moment axis, and the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 The angle between which is defined, wherein the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 40 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 30 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 20. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 15 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 10 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least two angles therebetween being less than 20. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least two angles therebetween being less than 15. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least two angles therebetween being less than 10.
In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 All three angles in between are less than 20 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 All three angles in between are less than 15 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 All three angles in between are less than 10 °.
In some embodiments of such heteroleptic compounds, the compounds have a Vertical Dipole Ratio (VDR) of 0.33 or less. In some embodiments of such compounded compounds, the compounds have a VDR of 0.30 or less. In some embodiments of such compounded compounds, the compounds have a VDR of 0.25 or less. In some embodiments of such compounded compounds, the compounds have a VDR of 0.20 or less. In some embodiments of such compounded compounds, the compounds have a VDR of 0.15 or less.
The meaning of the term transition dipole moment axis of a compound and the perpendicular dipole ratio of the compound will be readily understood by those of ordinary skill in the art. However, the meaning of these terms can be found in U.S. patent No. 10,672,997, the disclosure of which is incorporated herein by reference in its entirety. U.S. patent No. 10,672,997 discusses the horizontal dipole ratio of compounds, rather than VDR. However, one skilled in the art will readily appreciate that vdr=1-HDR.
In some embodiments, the first emitter has a formula selected from the group consisting of: ir (L) A ) 3 、Ir(L A )(L B ) 2 、Ir(L A ) 2 (L B )、Ir(L A ) 2 (L C )、Ir(L A )(L B )(L C ) And Pt (L) A )(L B )；
Wherein L is A 、L B And L C In Ir compounds are different from each other;
wherein L is A And L B The Pt compounds may be the same or different; and is also provided with
Wherein L is A And L B May be linked to form a tetradentate ligand in the Pt compound.
In some embodiments, the first emitter has a formula selected from the group consisting of the formulas in list 3 below:
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wherein the method comprises the steps of
X 96 To X 99 Is independently C or N;
each Y 100 Independently selected from the group consisting of NR ", O, S and Se;
R 10a 、R 20a 、R 30a 、R 40a and R is 50a Independently represents a single substitution, up to a maximum substitution or no substitution;
R、R'、R”、R 10a 、R 11a 、R 12a 、R 13a 、R 20a 、R 30a 、R 40a 、R 50a 、R 60 、R 70 、R 97 、R 98 and R is 99 Each of which is independently hydrogen or is selected from the group consisting ofSubstituents of the group consisting of the general substituents defined.
In some embodiments, the first emitter has a formula selected from the group consisting of the formulas in list 4 below:
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wherein:
X 96 to X 99 Is independently C or N;
each Y 100 Independently selected from the group consisting of NR ", O, S and Se;
l is independently selected from the group consisting of: direct bond, BR "R '", NR ", PR", O, S, se, C = O, C = S, C =se, c=nr ", c=cr" R' ", s= O, SO 2 CR ", CR" R ' ", siR" R ' ", ger" R ' ", alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
X 100 at each occurrence selected from the group consisting of: o, S, se, NR "and CR" R' ";
each R 10a 、R 20a 、R 30a 、R 40a And R is 50a 、R A” 、R B” 、R C” 、R D” 、R E” And R is F” Independently represents mono-substituted, up to maximum substituted or unsubstituted;
R、R'、R”、R”'、R 10a 、R 11a 、R 12a 、R 13a 、R 20a 、R 30a 、R 40a 、R 50a 、R 60 、R 70 、R 97 、R 98 、R 99 、R A1' 、R A2' 、R A” 、R B” 、R C” 、R D” 、R E” 、R F” 、R G” 、R H” 、R I” 、R J” 、R K” 、R L” 、R M” and R is N” Each of which is independently hydrogen or a substituent selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, borane, seleno, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof. In some embodiments, the EML further comprises a first emitter; and wherein the first emitter is capable of acting as a delayed fluorescence emitter in an OLED at room temperature.
In some embodiments, the first emitter is capable of functioning as a heat-activated delayed fluorescence emitter in an OLED at room temperature.
In some embodiments, the first emitter comprises at least one donor group and at least one acceptor group.
In some embodiments, the first emitter is a metal complex.
In some embodiments, the first emitter is a non-metal complex.
In some embodiments, the first emitter is a Cu, ag, or Au complex.
In some embodiments, the first emitter comprises at least one of the chemical moieties selected from the group consisting of:
in some embodiments, the first emitter has the formula M (L 5 )(L 6 ) Wherein M is Cu, ag or Au, L 5 And L 6 Is different and L 5 And L 6 Independently selected from the group consisting of:
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wherein A is 1 -A 9 Each independently selected from C or N;
wherein each R is P 、R P 、R U 、R SA 、R SB 、R RA 、R RB 、R RC 、R RD 、R RE And R is RF Independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germyl, borane, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof. In some embodiments, R P 、R P 、R U 、R SA 、R SB 、R RA 、R RB 、R RC 、R RD 、R RE And R is RF At least one of (a)One containing the first element and R P 、R P 、R U 、R SA 、R SB 、R RA 、R RB 、R RC 、R RD 、R RE And R is RF Comprises a second element. In some embodiments, R P 、R P 、R U 、R SA 、R SB 、R RA 、R RB 、R RC 、R RD 、R RE And R is RF Comprises a third element.
In some embodiments, the first emitter is selected from the group consisting of the structures in the following TADF list:
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in some embodiments, the first emitter comprises at least one of the chemical moieties selected from the group consisting of:
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wherein Y is T 、Y U 、Y V And Y W Each independently selected from the group consisting of: BR, NR, PR, O, S, se, C = O, S = O, SO 2 BRR ', CRR', siRR ', and GeRR';
wherein each R is T May be the same or different, and each R T Independently a donor, an acceptor group, an organic linking group bonded to the donor, an organic linking group bonded to the acceptor group, or an end group selected from the group consisting of:alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, aryl, heteroaryl, and combinations thereof; and is also provided with
R and R' are each independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, borane, aralkyl, alkoxy, aryloxy, amino, silyl, germanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof. In some of the above embodiments, any carbon ring atom up to a maximum total of three in each phenyl ring in any of the above structures, along with its substituents, may be substituted with N. In some embodiments, the compound comprises at least one of the chemical moieties selected from the group consisting of: nitriles, isonitriles, boranes, fluorides, pyridines, pyrimidines, pyrazines, triazines, aza-carbazole, aza-dibenzothiophenes, aza-dibenzofurans, aza-dibenzoselenophenes, aza-triphenylenes, imidazoles, pyrazoles, oxazoles, thiazoles, isoxazoles, isothiazoles, triazoles, thiadiazoles, and oxadiazoles.
In some embodiments, the EML further comprises a first emitter; and wherein the first emitter is capable of acting as a fluorescent emitter in an OLED at room temperature.
In some embodiments, the first emitter comprises at least one organic group selected from the group consisting of:
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wherein Y is F 、Y G 、Y H And Y I Each independently selected from the group consisting of: BR, NR, PR, O, S, se, C = O, S = O, SO 2 BRR ', CRR', siRR ', and GeRR';
wherein X is F And Y G Each independently selected from the group consisting of C and N; and is also provided with
Wherein R is F 、R G R, and R' are each independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein.
In some of the above embodiments, any carbon ring atom up to a maximum total of three in each phenyl ring in any of the above structures, along with its substituents, may be substituted with N.
In some embodiments, the first emitter is selected from the group consisting of:
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wherein Y is F1 To Y F4 Each independently selected from O, S and NR F1 ；
Wherein R is F1 And R is 1S To R 9S Each independently represents a single substitution to the maximum number of substitutions or no substitution possible; and is also provided with
Wherein R is F1 And R is 1S To R 9S Each independently is hydrogen or a substituent selected from the group consisting of the general substituents as defined herein.
In some embodiments, the first emitter comprises a structure selected from the group consisting of the structures of the following FL list:
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wherein the compound is substituted with at least one chemical group comprising a first element. In some embodiments, the compound is further substituted with at least one other chemical group comprising a second element. In some embodiments, the compound is further substituted with at least one other chemical group comprising a third element. In some of the above embodiments, any carbon ring atom up to a maximum total of three in each phenyl ring in any of the above structures, along with its substituents, may be substituted with N.
In some embodiments, the EML further includes a first emitter and a first body; wherein the first body comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the first body comprises at least two different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the first body comprises at least three different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the EML further comprises a second body; wherein the second body comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the second body comprises at least two different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the second body comprises at least three different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments, the EML further comprises a first emitter; and wherein the first emitter comprises a lanthanide metal.
In some embodiments, the second compound as described herein may be an emissive dopant or a non-emissive dopant.
In some embodiments, the first layer and/or EML further comprises an additional host, wherein the additional host comprises a triphenylene comprising a benzofused thiophene or benzofused furan, wherein any substituent in the host is a non-fused substituent independently selected from the group consisting of: c (C) n H 2n+1 、OC n H 2n+1 、OAr 1 、N(C n H 2n+1 ) 2 、N(Ar 1 )(Ar 2 )、CH＝CH-C n H 2n+1 、C≡CC n H 2n+1 、Ar 1 、Ar 1 -Ar 2 、C n H 2n -Ar 1 Or unsubstituted, wherein n is an integer from 1 to 10; and wherein Ar is 1 With Ar 2 Independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
In some embodiments, the first layer and/or EML further comprises a further host, wherein the further host comprises at least one chemical moiety selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2 Benzo [ d ]]Benzo [4,5 ]]Imidazo [3,2-a]Imidazole, 5, 9-dioxa-13 b-boronaphtho [3,2,1-de]Anthracene, triazine, borane, silane, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ 2 Benzo [ d ]]Benzo [4,5 ]]Imidazo [3,2-a]Imidazole and aza- (5, 9-dioxa-13 b-boronaphtho [3,2, 1-de)]Anthracene).
In some embodiments, the additional subject may be selected from the group consisting of compounds in the following subject group:
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and combinations thereof.
In some embodiments, the first layer and/or the EML may further comprise a further host, wherein the further host comprises a metal complex.
According to a further embodiment, an OLED embodiment B is disclosed comprising: a first electrode; a second electrode; a first layer and an emissive layer (EML) disposed between the first electrode and the second electrode, wherein the first layer is configured as a Hole Blocking Layer (HBL) or an Electron Transport Layer (ETL). The first layer comprises a first compound comprising a first element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the first layer is an HBL. In some embodiments, the first layer is ETL.
In some embodiments of the OLED, the first compound further comprises a second element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; wherein the second element is different from the first element. In some embodiments, the first compound further comprises a third element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; wherein the third element is different from the first element and the second element.
In some embodiments of the OLED, the first compound comprises Si and B. In some embodiments, the first compound comprises Se and B. In some embodiments, the first compound comprises Se and Si. In some embodiments, the first compound comprises Ge and B. In some embodiments, the first compound comprises Se and Ge. In some embodiments, the first compound comprises Ge and Si. In some embodiments, the first compound comprises D.
In some embodiments, the first compound is selected from the group consisting of:
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wherein R is A To R K At least one of (a) comprises SiZ 1 Z 2 Z 3 Or GeZ 1 Z 2 Z 3 Wherein Z is 1 、Z 2 And Z 3 Each independently selected from hydrogen or a substituent selected from the group consisting of universal substituents as defined herein, wherein X 1 To X 3 Each independently is C or N, wherein R A To R K Is D, and wherein Y is S or Se. In some embodiments, Z 1 、Z 2 And Z 3 Is independently aryl or heteroaryl.
In some embodiments, the first layer further comprises a second compound. In some embodiments, the second compound contains at least one selected from the group consisting of: alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkaline earth metal halide, rare earth metal halide, alkali metal organic complex, alkaline earth metal organic complex, and rare earth metal organic complex. In some embodiments, the second compound comprises a first element selected from the group consisting of Li, al, yb, and Ca. In some embodiments, the second compound comprises a first element selected from the group consisting of Li and Al.
In some embodiments, the second compound comprises a first element selected from the group consisting of Li and Al. In some embodiments, the volume% of the second compound in the first layer is greater than 1%. In some embodiments, the volume% of the second compound in the first layer is greater than 5%. In some embodiments, the volume% of the second compound may be greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90%. In some, the volume% of the second compound may be 0%. In some embodiments, the OLED comprises a third compound comprising at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the third compound is the same as the first compound.
In some embodiments, the EML further comprises a third compound.
In some embodiments, the OLED further comprises a Hole Injection Layer (HIL) and/or a Hole Transport Layer (HTL) disposed between the first electrode and the second electrode, and the HIL or HTL comprises a third compound. In some embodiments, the EBL or HBL comprises a third compound. In some embodiments, the third compound comprises at least two different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the third compound comprises at least three different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments of OLED embodiment B, the EML further comprises a first emitter; and wherein the first emitter is capable of emitting light from a triplet excited state to a singlet ground state in the OLED at room temperature.
It should be appreciated that the previously described emitter or first emitter-related embodiments may be equally applicable throughout this disclosure.
In some embodiments of OLED embodiment B, the EML may further include a first emitter and a first host; wherein the first body comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments of the OLED, the EML may further include a second host; wherein the second body comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments of the OLED, the first body is selected from the group consisting of: />
And the second body is independently selected from the group consisting of: />
According to another aspect of the present disclosure, an OLED embodiment C is disclosed comprising:
a first electrode;
a second electrode;
a first layer and an EML disposed between the first electrode and the second electrode, wherein
The first layer is configured as an Electron Blocking Layer (EBL) or a Hole Transport Layer (HTL),
wherein the first layer comprises a first compound comprising a first element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments of OLED embodiment C, the first layer is an EBL. In some embodiments, the first layer is an HTL.
In some embodiments of OLED embodiment C, the first compound further comprises a second element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and wherein the second element is different from the first element.
In some embodiments, the first compound further comprises a third element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and wherein the third element is different from the first element and the second element. In some embodiments, the first compound comprises Si and B. In some embodiments, the first compound comprises Se and B. In some embodiments, the first compound comprises Se and Si. In some embodiments, the first compound comprises Ge and B. In some embodiments, the first compound comprises Se and Ge. In some embodiments, the first compound comprises Ge and Si. In some embodiments, the first compound comprises D.
In some embodiments of OLED embodiment C, the first compound may be selected from the group consisting of:
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wherein R is A To R K At least one of (a) comprises SiZ 1 Z 2 Z 3 Or GeZ 1 Z 2 Z 3 Wherein Z is 1 、Z 2 And Z 3 Each independently selected from hydrogen or substituents selected from the general substituents as defined herein; wherein X is 1 To X 3 Each independently is C or N,
wherein R is A To R K At least one of which is D,
wherein Y is S or Se.
In some of the above embodiments, Z 1 、Z 2 And Z 3 Is independently aryl or heteroaryl.
In some embodiments of OLED embodiment C, the first layer further comprises a second compound. In some embodiments, the second compound contains at least one selected from the group consisting of: alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkaline earth metal halide, rare earth metal halide, alkali metal organic complex, alkaline earth metal organic complex, and rare earth metal organic complex. In some embodiments, the second compound comprises a first element selected from the group consisting of Li, al, yb, and Ca. In some embodiments, the second compound comprises a first element selected from the group consisting of Li and Al.
In some embodiments, the second compound comprises a first element selected from the group consisting of Li and Al. In some embodiments, the volume% of the second compound in the first layer is greater than 1%. In some embodiments, the volume% of the second compound in the first layer is greater than 5%. In some embodiments, the volume% of the second compound may be greater than 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, or 90%. In some embodiments, the volume% of the second compound may be 0%. In some embodiments, the OLED comprises a third compound comprising at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the third compound is the same as the first compound.
In some embodiments, the EML further comprises a third compound.
In some embodiments, the OLED further comprises a Hole Injection Layer (HIL) and/or a Hole Transport Layer (HTL) disposed between the first electrode and the second electrode, and the HIL or HTL comprises a third compound. In some embodiments, the EBL or HBL comprises a third compound. Wherein the EBL or HBL comprises a third compound.
In some embodiments, the third compound comprises at least two different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se. In some embodiments, the third compound comprises at least three different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In some embodiments of OLED embodiment C, the EML further comprises a first emitter; and wherein the first emitter is capable of emitting light from a triplet excited state to a singlet ground state in the OLED at room temperature.
In OLED embodiment C, the first emitter may be the same first emitter compound as described above.
In OLED embodiment C, the EML may further include a first emitter and a first host; wherein the first body comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In OLED embodiment C, the EML may further include a second body; wherein the second body comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
In OLED embodiment C, the first body may be selected from the group consisting of:
and the second body is independently selected from the group consisting of: />
In some embodiments, the first compound and/or the second compound may be a sensitizer; wherein the device may further comprise a recipient; and wherein the receptor may be selected from the group consisting of: fluorescent emitters, delayed fluorescent emitters, and combinations thereof.
In yet another aspect, the OLED of the present disclosure may further comprise an emissive region comprising a compound as disclosed herein.
In some embodiments, the emissive region may comprise a compound as disclosed herein.
In some embodiments, at least one of the anode, cathode, or new layer disposed over the organic emissive layer serves as the enhancement layer. The enhancement layer includes a plasmonic material exhibiting surface plasmon resonance, the plasmonic material non-radiatively coupled to the emitter material and transferring excited state energy from the emitter material to a non-radiative mode of surface plasmon polaritons. The enhancement layer is disposed no further than a threshold distance from the organic emissive layer, wherein the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer, and the threshold distance is where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed on the enhancement layer on an opposite side of the organic emissive layer. In some embodiments, the outcoupling layer is disposed on the opposite side of the emission layer from the enhancement layer, but is still able to outcouple energy from the surface plasmon mode of the enhancement layer. The outcoupling layer scatters energy from the surface plasmon polaritons. In some embodiments, this energy is scattered into free space as photons. In other embodiments, energy is scattered from surface plasmon modes of the device into other modes, such as, but not limited to, an organic waveguide mode, a substrate mode, or another waveguide mode. If the energy is scattered to the non-free space mode of the OLED, other outcoupling schemes may be incorporated to extract the energy into free space. In some embodiments, one or more intervening layers may be disposed between the enhancement layer and the outcoupling layer. Examples of intervening layers may be dielectric materials, including organic, inorganic, perovskite, oxides, and may include stacks and/or mixtures of these materials.
The enhancement layer alters the effective properties of the medium in which the emitter material resides, causing any or all of the following: reduced emissivity, altered emission linearity, altered emission intensity with angle, altered emitter material stability, altered OLED efficiency, and reduced OLED device roll-off efficiency. Placing the enhancement layer on the cathode side, the anode side, or both sides creates an OLED device that takes advantage of any of the effects described above. In addition to the specific functional layers mentioned herein and illustrated in the various OLED examples shown in the figures, an OLED according to the present disclosure may also include any other functional layers common in OLEDs.
The enhancement layer may comprise a plasmonic material, an optically active super-structured material or a hyperbolic super-structured material. As used herein, a plasmonic material is a material in which the real part of the dielectric constant crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material comprises at least one metal. In such embodiments, the metal may include at least one of the following: ag. Al, au, ir, pt, ni, cu, W, ta, fe, cr, mg, ga, rh, ti, ru, pd, in, bi, ca, alloys or mixtures of these materials, and stacks of these materials. Generally, a metamaterial is a medium composed of different materials, wherein the overall effect of the medium is different from the sum of its material portions. In particular, we define an optically active super-structured material as a material having both negative permittivity and negative permeability. On the other hand, hyperbolic metamaterials are anisotropic media in which the permittivity or permeability has different signs for different spatial directions. Optically active and hyperbolic metamaterials are very different from many other photonic structures, such as distributed Bragg reflectors (Distributed Bragg Reflector, "DBRs"), because the medium should exhibit uniformity in the direction of propagation over the length scale of the wavelength of light. Using terms that will be understood by those skilled in the art: the dielectric constant of a metamaterial in the propagation direction can be described by an effective dielectric approximation. Plasmonic and super-structured materials provide a method for controlling light propagation that can enhance OLED performance in a variety of ways.
In some embodiments, the enhancement layer is provided as a planar layer. In other embodiments, the enhancement layer has wavelength-sized features that are periodically, quasi-periodically, or randomly arranged, or sub-wavelength-sized features that are periodically, quasi-periodically, or randomly arranged. In some embodiments, the wavelength-sized features and the sub-wavelength-sized features have sharp edges.
In some embodiments, the outcoupling layer has wavelength-sized features that are periodically, quasi-periodically, or randomly arranged, or sub-wavelength-sized features that are periodically, quasi-periodically, or randomly arranged. In some embodiments, the outcoupling layer may be composed of a plurality of nanoparticles, and in other embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed over the material. In these embodiments, the outcoupling may be adjusted by at least one of the following means: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material or an additional layer disposed on the plurality of nanoparticles, changing the thickness of the reinforcing layer, and/or changing the material of the reinforcing layer. The plurality of nanoparticles of the device may be formed from at least one of: a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or layering of one or more materials and/or a core of one type of material and a shell coated with another type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of: ag. Al, au, ir, pt, ni, cu, W, ta, fe, cr, mg, ga, rh, ti, ru, pd, in, bi, ca, alloys or mixtures of these materials, and stacks of these materials. The plurality of nanoparticles may have additional layers disposed over them. In some embodiments, the polarization of the emission may be adjusted using an outcoupling layer. Changing the size and periodicity of the outcoupling layer may select the type of polarization that preferentially outcouples to air. In some embodiments, the outcoupling layer also serves as an electrode of the device.
In yet another aspect, the present disclosure also provides a consumer product comprising an Organic Light Emitting Device (OLED) as described herein.
In some embodiments, the consumer product may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
In general, an OLED includes at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer. The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and a hole are localized on the same molecule, an "exciton" is formed, which is a localized electron-hole pair having an excited energy state. Light is emitted when the exciton relaxes through a light emission mechanism. In some cases, excitons may be localized on an excimer or exciplex. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.
Several OLED materials and configurations are described in U.S. patent nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
Initial OLEDs used emissive molecules that emitted light ("fluorescence") from a singlet state, as disclosed, for example, in U.S. patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in time frames less than 10 nanoseconds.
Recently, OLEDs have been demonstrated that have emissive materials that emit light from a triplet state ("phosphorescence"). Baldo et al, "efficient phosphorescent emission from organic electroluminescent devices (Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices)", nature, vol.395, 151-154,1998 ("Baldo-I"); and Bardo et al, "Very efficient green organic light emitting device based on electrophosphorescence (Very high-efficiency green organic light-emitting devices based on electrophosphorescence)", applied physical fast report (appl. Phys. Lett.), vol.75, stages 3,4-6 (1999) ("Bardo-II"), incorporated by reference in its entirety. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704, columns 5-6, which is incorporated by reference.
Fig. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. The device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a blocking layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 may be fabricated by depositing the layers in sequence. The nature and function of these various layers and example materials are described in more detail in U.S. Pat. No. 7,279,704 at columns 6-10, which is incorporated by reference.
Further examples of each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F in a 50:1 molar ratio 4 m-MTDATA of TCNQ, as disclosed in U.S. patent application publication No. 2003/0239980, which is incorporated by reference in its entirety. Examples of luminescent and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of cathodes are disclosed in U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, that include composite cathodes having a thin layer of metal (e.g., mg: ag) containing an overlying transparent, electrically conductive, sputter-deposited ITO layer. The theory and use of barrier layers is described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of implanted layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
Fig. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. The device 200 may be fabricated by depositing the layers in sequence. Because the most common OLED configuration has a cathode disposed above an anode, and the device 200 has a cathode 215 disposed below an anode 230, the device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. Fig. 2 provides one example of how some layers may be omitted from the structure of the apparatus 100.
The simple layered structure illustrated in fig. 1 and 2 is provided by way of non-limiting example, and it should be understood that embodiments of the present disclosure may be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be obtained by combining the various layers described in different ways, or the layers may be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it should be understood that combinations of materials may be used, such as mixtures of host and dopant, or more generally, mixtures. Further, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to fig. 1 and 2.
Structures and materials not specifically described, such as OLEDs (PLEDs) comprising polymeric materials, such as disclosed in frank (Friend) et al, U.S. patent No. 5,247,190, which is incorporated by reference in its entirety, may also be used. By way of another example, an OLED with a single organic layer may be used. The OLEDs can be stacked, for example, as described in U.S. patent No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Furster et al, and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Boolean et al, which are incorporated by reference in their entirety.
Any of the layers of the various embodiments may be deposited by any suitable method unless otherwise specified. Preferred methods for the organic layer include thermal evaporation, ink jet (as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, incorporated by reference in their entirety), organic vapor deposition (OVPD) (as described in U.S. Pat. No. 6,337,102, incorporated by reference in its entirety, furster et al), and deposition by organic vapor jet printing (OVJP, also known as Organic Vapor Jet Deposition (OVJD)), as described in U.S. Pat. No. 7,431,968, incorporated by reference in its entirety. Other suitable deposition methods include spin-coating and other solution-based processes. The solution-based process is preferably carried out under nitrogen or an inert atmosphere. For other layers, the preferred method includes thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding (as described in U.S. patent nos. 6,294,398 and 6,468,819, incorporated by reference in their entirety), and patterning associated with some of the deposition methods such as inkjet and Organic Vapor Jet Printing (OVJP). Other methods may also be used. The material to be deposited may be modified to suit the particular deposition method. For example, substituents such as alkyl and aryl groups that are branched or unbranched and preferably contain at least 3 carbons can be used in small molecules to enhance their ability to withstand solution processing. Substituents having 20 carbons or more may be used, and 3 to 20 carbons are a preferred range. A material with an asymmetric structure may have better solution processibility than a material with a symmetric structure because an asymmetric material may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
Devices fabricated according to embodiments of the present disclosure may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from harmful substances exposed to the environment including moisture, vapors and/or gases, etc. The barrier layer may be deposited on the substrate, electrode, under or beside the substrate, electrode, or on any other portion of the device, including the edge. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include a composition having a single phase and a composition having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic compounds or organic compounds or both. Preferred barrier layers comprise a mixture of polymeric and non-polymeric materials, as described in U.S. patent No. 7,968,146, PCT patent application No. PCT/US2007/023098, and PCT/US2009/042829, which are incorporated herein by reference in their entirety. To be considered as a "mixture", the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same reaction conditions and/or simultaneously. The weight ratio of polymeric material to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be produced from the same precursor material. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.
Devices manufactured in accordance with embodiments of the present disclosure may be incorporated into a wide variety of electronic component modules (or units), which may be incorporated into a wide variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices (e.g., discrete light source devices or lighting panels), etc., that may be utilized by end user product manufacturers. The electronics assembly module may optionally include drive electronics and/or a power source. Devices manufactured in accordance with embodiments of the present disclosure may be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. Disclosed is a consumer product comprising an OLED comprising a compound of the present disclosure in an organic layer in the OLED. The consumer product should include any kind of product that contains one or more light sources and/or one or more of some type of visual display. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular telephones, tablet computers, tablet phones, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays (displays with a diagonal of less than 2 inches), 3-D displays, virtual or augmented reality displays, vehicles, video walls including a plurality of tiled displays, theatre or gym screens, phototherapy devices, and signs. Various control mechanisms may be used to control devices manufactured in accordance with the present disclosure, including passive matrices and active matrices. Many of the devices are intended to be used in a temperature range that is comfortable for humans, such as 18 ℃ to 30 ℃, and more preferably at room temperature (20-25 ℃), but can be used outside this temperature range (e.g., -40 ℃ to +80 ℃).
Further details regarding OLEDs and the definitions described above can be found in U.S. patent No. 7,279,704, which is incorporated herein by reference in its entirety.
The materials and structures described herein may be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices such as organic transistors may employ the materials and structures.
In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, crimpable, collapsible, stretchable and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.
In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED includes an RGB pixel arrangement or a white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal of less than 10 inches or an area of less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of at least 50 square inches. In some embodiments, the OLED is an illumination panel.
C. OLED device of the present disclosure with other materials
The organic light emitting device of the present disclosure may be used in combination with a variety of other materials. For example, it may be used in combination with a wide variety of hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. The materials described or referenced below are non-limiting examples of materials that may be used in combination with the devices disclosed herein, and one of ordinary skill in the art may readily review the literature to identify other materials that may be used in combination.
a) Conductive dopants:
the charge transport layer may be doped with a conductive dopant to substantially change its charge carrier density, which in turn will change its conductivity. Conductivity is increased by the generation of charge carriers in the host material and, depending on the type of dopant, a change in Fermi level (Fermi level) of the semiconductor can also be achieved. The hole transport layer may be doped with a p-type conductivity dopant, and an n-type conductivity dopant is used in the electron transport layer.
Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047 and US2012146012.
b)HIL/HTL：
The hole injection/transport material used in the present disclosure is not particularly limited, and any compound may be used as long as the compound is generally used as a hole injection/transport material. Examples of materials include (but are not limited to): phthalocyanines or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; a fluorocarbon-containing polymer; a polymer having a conductive dopant; conductive polymers such as PEDOT/PSS; self-assembled monomers derived from compounds such as phosphonic acids and silane derivatives; metal oxide derivatives, e.g. MoO x The method comprises the steps of carrying out a first treatment on the surface of the p-type semiconducting organic compounds such as 1,4,5,8,9, 12-hexaazatriphenylene hexacarbonitrile; a metal complex; a crosslinkable compound.
Examples of aromatic amine derivatives for the HIL or HTL include, but are not limited to, the following general structures:
Ar 1 to Ar 9 Is selected from: a group consisting of, for example, the following aromatic hydrocarbon cyclic compounds: benzene, biphenyl, triphenylene, naphthalene, anthracene, benzene, phenanthrene, fluorene, pyrene, and the like,Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, benzimidazole, indazole, and combinations thereof, Phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from an aromatic hydrocarbon ring group and an aromatic heterocyclic group and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group. Each Ar may be unsubstituted or may be substituted with a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In one aspect, ar 1 To Ar 9 Independently selected from the group consisting of:
wherein k is an integer from 1 to 20; x is X 101 To X 108 Is C (including CH) or N; z is Z 101 Is NAr 1 O or S; ar (Ar) 1 Having the same groups as defined above.
Examples of metal complexes used in the HIL or HTL include, but are not limited to, the following general formula:
wherein Met is a metal that may have an atomic weight greater than 40; (Y) 101 -Y 102 ) Is a bidentate ligand, Y 101 And Y 102 Independently selected from C, N, O, P and S; l (L) 101 Is an auxiliary ligand; k' is an integer value of 1 to the maximum number of ligands that can be attached to the metal; and k' +k "is the maximum that can be connected to the metalLigand number.
In one aspect, (Y) 101 -Y 102 ) Is a 2-phenylpyridine derivative. In another aspect, (Y) 101 -Y 102 ) Is a carbene ligand. In another aspect, met is selected from Ir, pt, os, and Zn. In another aspect, the metal complex has a chemical structure as compared to an Fc + The minimum oxidation potential in solution of less than about 0.6V for Fc coupling.
Non-limiting examples of HIL and HTL materials that can be used in an OLED in combination with the materials disclosed herein are exemplified with references disclosing those materials as follows: CN, DE, EP EP, JP07-, JP EP, EP JP07-, JP US, US US, WO US, US WO, WO.
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c)EBL：
An Electron Blocking Layer (EBL) may be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a barrier layer in a device may result in substantially higher efficiency and/or longer lifetime than a similar device lacking such a barrier layer. Furthermore, a blocking layer may be used to limit the emission to a desired area of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to vacuum level) and/or higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecule or the same functional group as used in one of the hosts described below.
d) A main body:
the light-emitting layer of the organic EL device of the present disclosure preferably contains at least a metal complex as a light-emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is greater than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria are met.
Examples of metal complexes used as hosts preferably have the general formula:
wherein Met is a metal; (Y) 103 -Y 104 ) Is a bidentate ligand, Y 103 And Y 104 Independently selected from C, N, O, P and S; l (L) 101 Is another ligand; k' is an integer value of 1 to the maximum number of ligands that can be attached to the metal; and k' +k "is the maximum number of ligands that can be attached to the metal.
In one aspect, the metal complex is:
wherein (O-N) is a bidentate ligand having a metal coordinated to the O and N atoms.
In another aspect, met is selected from Ir and Pt. In another aspect, (Y) 103 -Y 104 ) Is a carbene ligand.
In one aspect, the host compound contains at least one selected from the group consisting of: a group consisting of, for example, the following aromatic hydrocarbon cyclic compounds: benzene, biphenyl, triphenylene, tetramethylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole Benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranopyridine, furandipyridine, benzothiophenopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from an aromatic hydrocarbon ring group and an aromatic heterocyclic group and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group. Each option in each group may be unsubstituted or may be substituted with a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In one aspect, the host compound contains in the molecule at least one of the following groups:
wherein R is 101 Selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has a similar definition as Ar mentioned above. k is an integer from 0 to 20 or from 1 to 20. X is X 101 To X 108 Independently selected from C (including CH) or N. Z is Z 101 And Z 102 Independently selected from NR 101 O or S.
Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: US, WO WO, WO-based US, WO WO, US, US and US,
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e) Other emitters:
one or more other emitter dopants may be used in combination with the compounds of the present invention. Examples of other emitter dopants are not particularly limited, and any compound may be used as long as the compound is generally used as an emitter material. Examples of suitable emitter materials include, but are not limited to, compounds that can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF, also known as E-delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.
Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: CN, EB, EP1239526, EP, JP, KR TW, US20010019782, US TW, US20010019782, US US, US US, WO US, US US, WO.
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f)HBL：
A Hole Blocking Layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a barrier layer in a device may result in substantially higher efficiency and/or longer lifetime than a similar device lacking the barrier layer. Furthermore, a blocking layer may be used to limit the emission to a desired area of the OLED. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and/or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the HBL interface.
In one aspect, the compound used in the HBL contains the same molecules or the same functional groups as used in the host described above.
In another aspect, the compound used in the HBL contains in the molecule at least one of the following groups:
wherein k is an integer from 1 to 20; l (L) 101 Is another ligand, and k' is an integer from 1 to 3.
g)ETL：
An Electron Transport Layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complex or organic compound may be used as long as it is generally used to transport electrons.
In one aspect, the compounds used in ETL contain in the molecule at least one of the following groups:
wherein R is 101 Selected from the group consisting ofA group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof, when aryl or heteroaryl, have similar definitions as for Ar described above. Ar (Ar) 1 To Ar 3 Has a similar definition to Ar mentioned above. k is an integer of 1 to 20. X is X 101 To X 108 Selected from C (including CH) or N.
In another aspect, the metal complex used in ETL contains (but is not limited to) the following formula:
wherein (O-N) or (N-N) is a bidentate ligand having a metal coordinated to atom O, N or N, N; l (L) 101 Is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal.
Non-limiting examples of ETL materials that can be used in an OLED in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,
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h) Charge Generation Layer (CGL)
In tandem or stacked OLEDs, CGL plays a fundamental role in performance, consisting of n-doped and p-doped layers for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and the electrode. Electrons and holes consumed in the CGL are refilled with electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials include n and p conductivity dopants used in the transport layer.
In any of the above mentioned compounds used in each layer of the OLED device, the hydrogen atoms may be partially or fully deuterated. The minimum amount of deuterated hydrogen in the compound is selected from the group consisting of: 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99% and 100%. Thus, any of the specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, and the like, can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (e.g., without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. The disclosure as claimed may thus include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories as to why the present invention works are not intended to be limiting.
Experimental data
To understand the effect of incorporating a compound wherein the first element is selected from the group consisting of D, F, CN, si, ge, P, B and Se, OLED devices were grown. The OLED was grown on a glass substrate pre-coated with an Indium Tin Oxide (ITO) layer having a sheet resistance of 15- Ω/sq. The substrate was degreased with a solvent before any organic layers were deposited or coated, and then treated with an oxygen plasma at 50W for 1.5 minutes and with UV ozone for 5 minutes at 100 millitorr. After manufacture, in a nitrogen glove box @<1ppm of H 2 O and O 2 ) All devices were immediately encapsulated with an epoxy-sealed glass lid and the moisture absorbent was incorporated into the package interior. The doping percentages are in volume percent.
High vacuum by thermal evaporation<10 -6 Tray) were fabricated in the apparatus of table 1. The anode electrode isIndium Tin Oxide (ITO). The device example has an organic layer consisting of, in order from the ITO surface: />Compound 1 (HIL),Compound 2 (HTL) doped with 50% of the compounds indicated in the table,>compound 3 (EBL), ->Compound 3 (EML) doped with 50% of compound 5 and 12% of compound 4, -or->Compound 4 (BL)>Compound 6 (ETL) doped with 35% of compound 7,/o >Compound 5 (EIL), followed by +.>Al (cathode).
Table 1: comparison of compounds containing elements from D, F, CN, si, ge, P, B and Se with compounds without these elements when co-doped into the HTL of a blue PHOLED.
When used as a co-dopant in a hole transport layer, compounds containing at least one of the elements from D, F, CN, si, ge, P, B and Se provide an OLED with performance equal to or better than layers made with compounds that do not contain these unusual elements. For example, we found that compounds 8 and 13 each reduced the voltage of the OLED and increased the LT of the OLED compared to compound 3 without elements D, F, CN, si, ge, P, B and Se. The data in table 1 are normalized to the performance of the comparative compound, compound 3. The improved characteristics of these OLEDs suggest that one or more important device metrics can be improved by adjusting the atomic numbers of D, F, CN, si, ge, P, B and Se in the compounds incorporated into the HTL. The incorporation of multiple elements from the list of D, F, CN, si, ge, P, B and Se can yield even greater improvements.
High vacuum by thermal evaporation<10 -6 Tray) were fabricated in the apparatus of table 2. The anode electrode isIndium Tin Oxide (ITO). The device example has an organic layer consisting of, in order from the ITO surface: / >Compound 1 (HIL),Compound 2 (HTL), ->Compound 3 (EBL), ->Compound 3 (EML) doped with 50% of compound 5 and 12% of compound 4, -or->Compound 4 (BL)>Compound 6 (ETL) doped with 50% of the compounds indicated in the table,>compound 5 (EIL), followed by +.>Al (cathode).
Table 2: comparison of compounds containing elements from D, F, CN, si, ge, P, B and Se with compounds without these elements when co-doped into ETL of blue PHOLED.
When used as a co-dopant in an electron transport layer, compounds containing these unusual elements provide the performance of an OLED as well as or better than layers made with compounds that do not contain these unusual elements. For example, we utilize a variety of compounds containing unusual elements in the ETL of a blue PHOLED. We found that the compounds were compared to compound 14 without unusual elementsEach of items 8, 9, 10, 11, and 12 increases the EQE of the OLED, decreases the voltage of the OLED, or increases the LT of the OLED. The data in table 1 were normalized to the performance of the comparative compound, compound 14. We have found that OLEDs having co-dopants containing these unusual elements are at 10mA/cm 2 The lower voltage than the comparative compound 14 is a positive benefit. We have also found that OLEDs having co-dopants containing these unusual elements are at 20mA/cm 2 The stability below is higher than that of comparative compound 14, which is a positive benefit.
The compounds used in the OLED device were:
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Claims (15)

1. an organic light emitting device OLED comprising:
a first electrode;
a second electrode;
a first layer and an emissive layer EML disposed between the first electrode and the second electrode, wherein
The first layer is selected from the group consisting of: a hole injection layer HIL, a hole transport layer HTL, an electron blocking layer EBL, a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL;
the first layer includes a first compound including a first element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
2. The OLED of claim 1, wherein the first compound further comprises a second element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and wherein the first element is different from the second element; and/or
Wherein the first compound further comprises a third element selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and wherein the third element is different from the first element and the second element.
3. The OLED of claim 1, wherein the first layer is selected from the group consisting of HIL, HTL, and EBL; wherein the first element is selected from the group consisting of D, si, ge, P and Se; and/or
The first layer is selected from the group consisting of a HIL, a HTL, and an EBL; wherein each of the first element and the second element is independently selected from the group consisting of D, si, ge, P and Se.
4. The OLED of claim 1, wherein the first layer is selected from the group consisting of HBL, ETL, and EIL; wherein the first element is selected from the group consisting of: D. f, CN, si, ge, P, B and Se; and/or
Wherein the first layer is selected from the group consisting of HBL, ETL, and EIL; wherein each of the first element and the second element is independently selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
5. The OLED of claim 1, wherein the EML comprises a second compound comprising at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
6. The OLED of claim 1, wherein the EML comprises a second compound comprising at least two different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se; or (b)
The EML includes a second compound including at least three different elements selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
7. The OLED of claim 1, wherein OLED further comprises a second layer disposed between the first electrode and the second electrode;
wherein the method comprises the steps of
The second layer is selected from the group consisting of: HIL, HTL, EBL, HBL, ETL and EIL;
the second layer is a different type of layer than the first layer;
the second layer comprises a second compound; wherein the second compound comprises at least one element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
8. The OLED of claim 1, wherein the first compound is a non-metal containing compound.
9. The OLED of claim 1, wherein the EML further comprises a first emitter; and wherein the first emitter is capable of emitting light from a triplet excited state to a singlet ground state in the OLED at room temperature.
10. The OLED of claim 9, wherein the first emitter is a metal coordination complex having a metal-carbon bond; or (b)
The first emitter is a metal coordination complex having a metal-nitrogen bond or a metal-oxygen bond,
Wherein the metal is selected from the group consisting of: ir, rh, re, ru, os, pt, pd, au, ag and Cu.
11. The OLED of claim 9, wherein the first emitter has the formula M (L 1 ) x (L 2 ) y (L 3 ) z ；
Wherein L is 1 、L 2 And L 3 May be the same or different;
wherein x is 1, 2 or 3;
wherein y is 0, 1 or 2;
wherein z is 0, 1 or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein L is 1 Selected from the group consisting of the following structures:
wherein L is 2 And L 3 Independently selected from the group consisting of:
wherein: t is selected from the group consisting of B, al, ga and In;
K 1' selected from NR e 、PR e O, S and Se;
each Y 1 To Y 13 Independently selected from the group consisting of carbon and nitrogen;
y' is selected from the group consisting of: BR (BR) e 、BR e R f 、NR e 、PR e 、P(O)R e 、O、S、Se、C＝O、C＝S、C＝Se、C＝NR e 、C＝CR e R f 、S＝O、SO 2 、CR e R f 、SiR e R f And GeR e R f ；
R e And R is f Capable of being fused or joined to form a ring;
each R a 、R b 、R c And R is d Capable of independently representing a single to the maximum number of possible substitutions or no substitution;
each R a1 、R b1 、R a 、R b 、R c 、R d 、R e And R is f Independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, germanyl, borane, seleno, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; and is also provided with
R a1 、R b1 、R a 、R b 、R c And R is d Any two adjacent substituents of (a) can be fused or joined to form a ring or form a multidentate ligand.
12. A consumer product comprising the OLED of claim 1.
13. The consumer product of claim 12, wherein the consumer product is one of: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet phones, personal digital assistants PDAs, wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
14. An organic light emitting device, comprising:
a first electrode;
a second electrode;
a first layer and an emissive layer disposed between the first electrode and the second electrode, wherein the first layer is configured as a hole blocking layer or an electron transporting layer, and wherein the first layer comprises a first compound comprising a first element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
15. An organic light emitting device, comprising:
a first electrode;
a second electrode; and
a first layer and an emissive layer disposed between the first electrode and the second electrode, wherein the first layer is configured as an electron blocking layer or a hole transporting layer, and wherein the first layer comprises a first compound comprising a first element selected from the group consisting of: D. f, CN, si, ge, P, B and Se.
CN202310234798.5A 2022-03-09 2023-03-09 Organic electroluminescent material and device Pending CN116744710A (en)

Applications Claiming Priority (11)

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US63/318,269 2022-03-09
US63/326,548 2022-04-01
US63/329,688 2022-04-11
US63/329,924 2022-04-12
US63/342,198 2022-05-16
US63/367,818 2022-07-07
US63/395,173 2022-08-04
US63/400,416 2022-08-24
US63/401,800 2022-08-29
US18/116,390 US20230292586A1 (en) 2022-03-09 2023-03-02 Organic electroluminescent materials and devices
US18/116,390 2023-03-02

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