DE102020131491B4 - Organic electroluminescent material and device - Google Patents

Abstract

A compound having a structure of H-L1-E; and the ring A, the ring B and the ring C are in each occurrence identically or differently selected from an aromatic ring of 6 to 18 carbon atoms or a heteroaromatic ring of 3 to 18 carbon atoms;Rx represents a monosubstitution, multiple substitution or non-substitution; andadjacent substituents R, Rx may optionally be joined to form a ring;wherein E has a structure represented by Formula 2:wherein Y1 to Y12 are, in each occurrence, the same or different selected from N, C or CRy; and any two of Y5 to Y8 are selected from nitrogen, the other two of Y5 to Y8 are selected from C and CRy, respectively; and any two adjacent ones from Y1 to Y4C are and with Y9 or Y12; L1 is selected from a single bond, substituted or unsubstituted arylene of 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene of 3 to 30 carbon atoms, or combinations thereof; wherein R, Rx and Ry, the same or different in each occurrence, are selected from the group consisting of from: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof.

Description

Reference to related application(s)

This application claims priority to Chinese Patent Application No. CN201911201966.0 , filed on November 29, 2019, and Chinese Patent Application No. CN202010270250.2 , filed on April 13, 2020, the disclosure of which is incorporated herein by reference in its entirety.

Technical area

The present disclosure relates to compounds for organic electronic devices, for example organic electroluminescent devices. More particularly, the present disclosure relates to a novel compound having a parent core structure formed by condensing indole and pyrrole with an azamacrocycle and bound with benzoquinazoline or benzoquinoxaline and similar structures thereof, and an organic electroluminescent device and a compound formulation containing the compound.

background

Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors , organic photoreceptors, organic field quenching devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasmon emission devices.

In 1987, Tang and Van Slyke of Eastman Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinolato aluminum layer as the electron and emissive layers (Applied Physics Letters, 1987, 51(12): 913 -915). Once a bias voltage was applied to the device, green light was emitted from the device. This device laid the foundation for the development of modern organic light-emitting diodes (OLEDs). Prior art OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emitting layers between the cathode and anode. Because the OLED is a self-emitting solid-state device, it offers enormous potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, make them well suited for certain applications, such as fabrication on flexible substrates.

The OLED can be categorized into three different types according to their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet emission. The triplets generated in the device are wasted via non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of a fluorescent OLED is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs that use triplet emission from heavy metal-containing complexes as emitters. This allowed both singlets and triplets to be obtained, achieving an IQE of 100%. The discovery and development of phosphorescent OLEDs directly led to the commercialization of active matrix OLED (AMOLED) due to their high efficiency. Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap that allows the transition from the triplet back to the singlet. In the TADF device, the triplet excitons can undergo reverse intersystem crossing to generate singlet excitons, resulting in high IQE.

OLEDs can also be classified as small molecule and polymer OLEDs, depending on the shapes of the materials used. A small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of the small molecule can be large as long as it has a well-defined structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant emitting groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

There are different methods for producing OLEDs. Small molecule OLEDs are generally produced by thermal vacuum evaporation. Polymer OLEDs are manufactured through solution processes such as spin coating, inkjet printing and slot printing. If the material can be dissolved or dispersed in a solvent, the low molecular weight OLED can also be manufactured by a solution method.

The emission color of OLED can be achieved by the design of the emitter structure. An OLED may include one or a plurality of emitting layers to achieve the desired spectrum. In the case of green, yellow and red OLEDs, phosphorescent emitters have successfully achieved commercialization. A blue phosphorescent device still suffers from unsaturated blue color, short device life, and high operating voltage. Commercial full-color OLED displays typically adopt a hybrid strategy, using fluorescent blue and phosphorescent yellow or red and green. At present, the drop in efficiency of phosphorescent OLEDs remains a problem at high brightness. In addition, a more saturated emission color, higher efficiency and longer device life are desired.

Die offengelegte Verbindung muss jedoch eine Struktureinheit von Chinazolin oder Chinoxalin aufweisen und keine organische Verbindung wurde offengelegt und gelehrt, die eine Struktureinheit von Benzochinazolin oder Benzochinoxalin und ähnliche Strukturen davon enthält.The US20180337340A1 discloses an organic electroluminescent compound and an organic electroluminescent device containing the same, comprising an organic layer containing one or more hosts, a first host being an organic optical compound having the following structure:

However, the disclosed compound must have a structural unit of quinazoline or quinoxaline, and no organic compound has been disclosed and taught containing a structural unit of benzoquinazoline or benzoquinoxaline and similar structures thereof.

However, various previously known host materials still need to be further improved. In order to meet the increasing demands of the industry, a new material needs to be further researched and developed.

Summary

The present disclosure aims to provide a new compound having a parent core having an indole and pyrrole fused azamacrocycle structure and bound with benzoquinazoline or benzoquinoxaline and similar structures thereof to solve at least part of the above problems. The new compound can serve as a host material in an electroluminescent device and provide an electroluminescent device with better device performance such as higher efficiency/life. The present disclosure discloses a bipolar compound having a novel structure, the compound having an electron-transporting moiety comprising benzoquinazoline or benzoquinoxaline and a hole-transporting moiety formed by condensing indole and pyrrole with an azamacrocycle. The compound unexpectedly shows excellent properties in the balance of hole and electron transport and higher efficiency in a device, so that the device can provide better device performance.

• wobei H eine durch die Formel 1 dargestellte Struktur aufweist:
  
• wobei in Formel 1 A_1, A₂ und A₃ bei jedem Auftreten gleich oder verschieden aus CR ausgewählt sind; und der Ring A, der Ring B und der Ring C bei jedem Auftreten gleich oder verschieden aus einem aromatischen Ring mit 6 bis 18 Kohlenstoffatomen oder einem heteroaromatischen Ring mit 3 bis 18 Kohlenstoffatomen ausgewählt sind;
• R_x eine Monosubstitution, Mehrfachsubstitution oder Nichtsubstitution darstellt; und
• benachbarte Substituenten R, R_x gegebenenfalls verbunden sein können, dass sie einen Ring ausbilden;
• wobei E eine durch die Formel 2 dargestellte Struktur aufweist:
  
• wobei Y₁ bis Y₁₂ bei jedem Auftreten gleich oder verschieden aus N, C oder CR_y ausgewählt sind;
• und beliebige zwei von Y₅ bis Y₈ aus Stickstoff ausgewählt sind, die anderen zwei von Y₅ bis Y₈ aus C bzw. CR_y ausgewählt sind; und beliebige zwei benachbarte von Y₁ bis Y₄ C sind und mit Y₉ bzw. Y₁₂ verbunden sind;
• L₁ ausgewählt ist aus einer Einfachbindung, substituiertem oder unsubstituiertem Arylen mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroarylen mit 3 bis 30 Kohlenstoffatomen oder Kombinationen davon;
• wobei R, R_x und R_y bei jedem Auftreten gleich oder verschieden sind, ausgewählt sind aus der Gruppe bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, einer Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon.

According to one embodiment of the present disclosure, a compound having a structure of HL ₁ -E is disclosed;

• where H has a structure represented by Formula 1:
  
• where in Formula 1 A _1, A ₂ and A ₃ are selected identically or differently from CR in each occurrence; and the ring A, the ring B and the ring C are in each occurrence identically or differently selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms;
• R _x represents monosubstitution, multiple substitution or non-substitution; and
• adjacent substituents R, R _x can optionally be connected so that they form a ring;
• where E has a structure represented by Formula 2:
  
• where Y ₁ to Y ₁₂ are selected identically or differently from N, C or CR _y on each occurrence;
• and any two of Y ₅ to Y ₈ are selected from nitrogen, the other two of Y ₅ to Y ₈ are selected from C and CR _y , respectively; and any two adjacent ones of Y ₁ to Y ₄ are C and connected to Y ₉ and Y ₁₂ , respectively;
• L ₁ is selected from a single bond, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or combinations thereof;
• where _R , _R substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

• eine Anode,
• eine Kathode und
• eine organische Schicht, die zwischen der Anode und der Kathode angeordnet ist, wobei die organische Schicht die Verbindung nach einer der vorausgegangenen Ausführunsformen umfasst.

According to an embodiment of the present disclosure, there is further disclosed an electroluminescent device comprising:

• an anode,
• a cathode and
• an organic layer arranged between the anode and the cathode, the organic layer comprising the compound according to one of the preceding embodiments.

According to an embodiment of the present disclosure, a compound formulation is further disclosed comprising the compound having a structure of HL ₁ -E.

The present disclosure discloses a novel compound having a parent core with an indole and pyrrole fused azamacrocycle structure and bound to benzoquinazoline or benzoquinoxaline and similar structures thereof. The novel compound can serve as a host material in the electroluminescent device and provide electroluminescent devices with better device performance such as higher efficiency/lifetime.

Brief description of the drawings

• 1 shows a schematic diagram of an organic light emitting device that may include a compound and a compound formulation disclosed by the present disclosure.
• 2 shows a schematic representation of another organic light emitting device that may include a compound and a compound formulation disclosed by the present disclosure.

Detailed description

OLEDs can be manufactured on different types of substrates, such as glass, plastic and metal foil. 1 schematically shows the organic light emitting device 100 without limitation. The figures are not necessarily shown to scale. Some of the layers in the figures can also be omitted if necessary. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emission layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in this order. The properties and functions of these different layers as well as exemplary materials are discussed in US Pat. No. 7,279,704 described in more detail in columns 6-10, which is incorporated herein by reference in its entirety.

Additional examples of each of these layers are available. For example, a flexible and transparent substrate-anode combination is used in the US Pat. No. 5,844,363 disclosed, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA, which is doped with F ₄ -TCNQ in a molar ratio of 50:1, as shown in the US Patent Application No. 2003/0230980 disclosed, which is incorporated herein by reference in its entirety. Examples of host materials are given in the US Pat. No. 6,303,238 by Thompson et al. disclosed, which is incorporated herein 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 described in U.S. Patent Application No. 2003/0230980 disclosed, which is incorporated herein by reference in its entirety. The US Pat. No. 5,703,436 and No. 5,707,745, incorporated herein by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin metal layer, such as Mg:Ag, with an overlying transparent, electrically conductive, sputtered ITO layer. The theory and use of blocking layers are described in US Pat. No. 6,097,147 and US Patent Application No. 2003/0230980 described in more detail, which are incorporated herein by reference in their entirety. Examples of injection layers are shown in US Patent Application No. 2004/0174116 provided, which is incorporated herein by reference in its entirety. A description of protective layers can be found in US Patent Application No. 2004/0174116 , which is incorporated herein by reference in its entirety.

The layered structure described above is provided by non-limiting examples. Functional OLEDs can be created by combining the various layers described below can be achieved in different ways or layers can be omitted entirely. It may also include other layers that are not specifically described. A single material or a blend of multiple materials can be used within each layer to achieve optimal performance. Each functional layer can include multiple sublayers. For example, the emitting layer can have two layers of different emitting materials in order to achieve the desired emission spectrum.

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 multiple layers.

An OLED can be encapsulated by a barrier layer. 2 schematically shows the organic light emitting device 200 without limitation. 2 differs from 1 in that the organic light emitting device includes a barrier layer 102 located above the cathode 190 to protect it from harmful environmental species such as moisture and oxygen. Any material that can provide the barrier function, such as glass and organic-inorganic hybrid layers, can be used as the barrier layer. The barrier layer should be placed directly or indirectly outside the OLED device. A multi-layer thin film encapsulation was developed US Pat. No. 7,968,146 which is incorporated herein by reference in its entirety.

Devices manufactured in accordance with embodiments of the present disclosure may be incorporated into a variety of consumer products containing one or more electronic component modules (or units) therein. Some examples of such consumer products are flat screens, monitors, medical monitors, televisions, billboards, luminaires for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablets, phablets , wearable devices, smartwatches, laptops, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, vehicle displays and vehicle taillights.

The materials and structures described herein can be used in other organic electronic devices listed above.

As used herein, “top” means furthest from the substrate while “bottom” means closest to the substrate. When a first layer is described as being “located above” a second layer, the first layer is located further away from the substrate. There may be additional layers between the first and second layers unless it is stated that the first layer is “in contact with” the second layer. For example, a cathode can be described as being “placed above” an anode, even though there are various organic layers in between.

As used herein, “solution processable” means the ability to be dissolved, dispersed or transported and/or deposited in a liquid medium in either solution or suspension form.

A ligand can be said to be “photoactive” if the ligand is believed to contribute directly to the photoactive properties of an emissive material. A ligand can be described as "helping" if the ligand is considered not to contribute to the photoactive properties of an emissive material, although an auxiliary ligand can alter the properties of a photoactive ligand.

It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the spin statistics limit of 25% through delayed fluorescence. As used herein, there are two types of delayed fluorescence, namely delayed P-type fluorescence and delayed E-type fluorescence. The delayed P-type fluorescence is generated by triplet-triplet annihilation (TTA).

On the other hand, delayed E-type fluorescence is not due to the collision of two triplets but rather to the transition between the triplet states and the singlet excited states. Compounds capable of producing delayed E-type fluorescence must have very small singlet-triplet gaps to convert between energy states. Thermal energy can do that Activate transition from triplet state back to singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A special feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing is fast enough to minimize the nonradiative decay from the triplet state, the fraction of repopulated singlet excited states can potentially reach 75%. The total singlet content can be 100% and is therefore well above 25% of the spin statistic limit for electrically generated excitons.

Delayed E-type fluorescence properties are found in an exciplex system or in a single compound. Without being bound by theory, it is believed that delayed E-type fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔES-T). Organic, nonmetal-containing, luminescent donor-acceptor materials can achieve this. The emission in these materials is often characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of HOMO and LUMO in these donor-acceptor type compounds often results in a small ΔE _ST . These conditions may include CT conditions. Often, luminescent donor-acceptor materials are prepared by combining an electron donor moiety, such as amino or carbazole derivatives, and an electron acceptor moiety, such as N-containing six-membered aromatic rings.

Definition of substituent names

Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

Alkyl - considers both straight and branched chain alkyl groups. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group , N-anon cyl group, N-Dodecyl group, N-Tridecyl group, N tetraCyl group, N-pentecyl group, N-hexadecyl group, N heptaecyl group, N-Octecyl group, neopentyl group, 1-methyl pentyl group, 1-pentylhexyl group, 1-butyl pentyl group , 1-heptyloctyl group and 3-methylpentyl group. In addition, the alkyl group may optionally be substituted. The carbons in the alkyl chain can be substituted by other heteroatoms. Of the above, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, tert-butyl group, n-pentyl group and neopentyl group are preferred.

Cycloalkyl - as used here, takes into account cyclic alkyl groups. Preferred cycloalkyl groups are those with 4 to 10 ring carbon atoms and include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, the cycloalkyl group may optionally be substituted. The carbons in the ring can be replaced by other heteroatoms.

Alkenyl - as used here, takes into account both straight and branched chain alkene groups. Preferred alkenyl groups are those with 2 to 15 carbon atoms. Examples of the alkenyl group include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1 ,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group and 3-phenyl-1-butenyl group. In addition, the alkenyl group may optionally be substituted.

Alkynyl - as used here, takes into account both straight and branched chain alkyne groups. Preferred alkynyl groups are those with 2 to 15 carbon atoms. In addition, the alkynyl group may optionally be substituted.

Aryl or aromatic group - as used herein, takes into account uncondensed and fused systems. Preferred aryl groups are those with six to sixty carbon atoms, preferably six to twenty carbon atoms, preferably six to twelve carbon atoms. Examples of the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may optionally be substituted. Examples of the unfused aryl group include phenyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, p-terphenyl-4-yl group, p-terphenyl-3-yl -group, p-terphenyl-2-yl group, m-ter phenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p-(2 -Phenylpropyl)phenyl group, 4'-methylbiphenylyl group, 4"-t-butyl-p-terphenyl-4-yl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2 ,5-xylyl group, mesityl group and m-quarterphenyl group.

Heterocyclic group or heterocycle - as used herein includes aromatic and non-aromatic cyclic groups. Hetero-aromatic also means heteroaryl. Preferred nonaromatic heterocyclic groups are those with 3 to 7 ring atoms that include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one heteroatom selected from nitrogen atom, oxygen atom, sulfur atom and selenium atom.

Heteroaryl - as used herein, includes unfused and fused heteroaromatic groups, which may contain one to five heteroatoms. Preferred heteroaryl groups are those with three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably 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, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine , pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine , phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3- Azaborine, 1,4- Azaborine, borazine and aza analogues thereof. In addition, the heteroaryl group may optionally be substituted.

Alkoxy - is represented by -O-alkyl. Examples and preferred examples thereof are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group and hexyloxy group. The alkoxy group with 3 or more carbon atoms can be linear, cyclic or branched.

Aryloxy - is represented by -O-Aryl or -O-Heteroaryl. Examples and preferred examples thereof are the same as those described above. Examples of the aryloxy group having 6 to 40 carbon atoms include phenoxy group and biphenyloxy group.

Arylalkyl - as used herein, considers an alkyl group that has an aryl substituent. In addition, the arylalkyl group may optionally be substituted. Examples of the arylalkyl group include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl tert-butyl group, alpha-naphthylmethyl group, 1-alpha-naphthylethyl group, 2-alpha-naphthylethyl group, 1-alpha- Naphthylisopropyl group, 2-alpha-naphthylisopropyl group, beta-naphthylmethyl group, 1-beta-naphthylethyl group, 2-beta-naphthylethyl group, 1-beta-naphthylisopropyl group, 2-beta-naphthylisopropyl group, p-methylbenzyl group, m-methylbenzyl group, o- Methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group and 1-chloro-2- phenylisopropyl group. Of those mentioned above, preferred are benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group and 2-phenylisopropyl group.

The term “Aza” in azadibenzofuran, azadibenzothiophene, etc. means that one or more of the C-H groups in the respective aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs with two or more nitrogens in the ring system. One skilled in the art can easily imagine other nitrogen analogues of the aza derivatives described above, and all such analogues are intended to be encompassed by the terms set forth herein.

In the present disclosure, unless otherwise defined, any term from the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted arylalkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted means Arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid group, substituted ester group, substituted sulfinyl, substituted sulfonyl and substituted phosphino is used that any group of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, Alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid group, ester group, sulfinyl, sulfonyl and phosphino may be substituted with one or more groups selected from the group consisting of deuterium, an unsubstituted alkyl with 1 to 20 carbon atoms, an unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl with 1 to 20 carbon atoms, an unsubstituted arylalkyl with 7 to 30 carbon atoms, an unsubstituted alkoxy with 1 to 20 carbon atoms, an unsubstituted aryloxy with 6 to 30 carbon atoms, an unsubstituted alkenyl with 2 to 20 carbon atoms, one unsubstituted aryl with 6 to 30 carbon atoms or preferably an unsubstituted aryl with 6 to 12 carbon atoms, an unsubstituted heteroaryl with 3 to 30 carbon atoms or preferably an unsubstituted heteroaryl with 3 to 12 carbon atoms, an unsubstituted alkylsilyl with 3 to 20 carbon atoms, an unsubstituted arylsilyl group 6 to 20 carbon atoms, an unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group and combinations thereof.

It is understood that when a molecular fragment is described as a substituent or otherwise attached to another residue, its name may be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the entire molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these various methods of designating a substituent or a bound fragment are considered equivalent.

In the compounds mentioned in this disclosure, the hydrogen atoms can be partially or completely replaced by deuterium. Other atoms, such as carbon and nitrogen, can also be replaced with their other stable isotopes. Replacement with other stable isotopes in the compounds may be preferred due to improving device efficiency and stability. In the compounds mentioned in the present disclosure, a deuterated substituent, such as deuterated methyl, refers to at least one hydrogen atom in the substituent (methyl) being replaced by deuterium.

In the compounds mentioned in this disclosure, multiple substitutions refer to a range that includes double substitution up to the maximum available substitutions. When a substitution in the compounds mentioned in this disclosure represents multiple substitutions (including di-, tri-, tetra-substitutions, etc.), i.e. the substituent can exist at a variety of available substitution positions on its compound structure, the substituents located at one There are a large number of available substitution positions that have the same structure or different structures.

In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be bonded into a ring unless expressly defined otherwise, e.g., adjacent substituents can optionally be bonded into a ring. In the compounds mentioned in the present disclosure, a case in which adjacent substituents can optionally be connected to form a ring includes a case in which adjacent substituents can be connected to form a ring and a case in which neighboring substituents are not connected so that they form a ring. When adjacent substituents can optionally be linked to form a ring, the ring formed can be monocyclic or polycyclic as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. In such an expression, adjacent substituents may refer to substituents bonded to the same atom, to substituents bonded to carbon atoms bonded directly to each other, or to substituents bonded to carbon atoms further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and to substituents bonded to carbon atoms bonded directly to each other.

The expression that two adjacent substituents can optionally be bonded to form a ring is also intended to mean that two substituents bonded to the same carbon atom ths are connected to each other via a chemical bond so that they form a ring, which can be illustrated by the following formula:

The expression that two adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents that are bonded to carbon atoms directly bonded to one another are linked to one another via a chemical bond to form a ring, which can be illustrated by the following formula:

Furthermore, the expression that two adjacent substituents can optionally be bonded to form a ring is also intended to mean that in the case that one of the two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to a position where the hydrogen atom is bonded, forming a ring. This is illustrated by the following formula:

• wobei H eine durch die Formel 1 dargestellte Struktur aufweist:
  
• wobei in Formel 1 A_1, A₂ und A₃ bei jedem Auftreten gleich oder verschieden aus CR ausgewählt sind; und der Ring A, der Ring B und der Ring C bei jedem Auftreten gleich oder verschieden aus einem aromatischen Ring mit 6 bis 18 Kohlenstoffatomen oder einem heteroaromatischen Ring mit 3 bis 18 Kohlenstoffatomen ausgewählt sind;
• R_x eine Monosubstitution, Mehrfachsubstitution oder Nichtsubstitution darstellt; und
• benachbarte Substituenten R, R_x gegebenenfalls verbunden sein können, dass sie einen Ring ausbilden;
• wobei E eine durch die Formel 2 dargestellte Struktur aufweist:
  
• wobei Y₁ bis Y₁₂ bei jedem Auftreten gleich oder verschieden aus N, C oder CR_y ausgewählt sind;
• und beliebige zwei von Y₅ bis Y₈ aus Stickstoff ausgewählt sind, die anderen zwei von Y₅ bis Y₈ aus C bzw. CR_y ausgewählt sind; und beliebige zwei benachbarte von Y₁ bis Y₄ C sind und mit Y₉ bzw. Y₁₂ verbunden sind;
• L₁ ausgewählt ist aus einer Einfachbindung, substituiertem oder unsubstituiertem Arylen mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroarylen mit 3 bis 30 Kohlenstoffatomen oder Kombinationen davon;
• wobei R, R_x und R_y bei jedem Auftreten gleich oder verschieden sind, ausgewählt sind aus der Gruppe bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, einer Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon.

According to an embodiment of the present disclosure, a compound having a structure of H-L1-E is disclosed;

• where H has a structure represented by Formula 1:
  
• where in Formula 1 A _1, A ₂ and A ₃ are selected identically or differently from CR in each occurrence; and the ring A, the ring B and the ring C are in each occurrence identically or differently selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms;
• R _x represents monosubstitution, multiple substitution or non-substitution; and
• adjacent substituents R, R _x can optionally be connected so that they form a ring;
• where E has a structure represented by Formula 2:
  
• where Y ₁ to Y ₁₂ are selected identically or differently from N, C or CR _y on each occurrence;
• and any two of Y ₅ to Y ₈ are selected from nitrogen, the other two of Y ₅ to Y ₈ are selected from C and CR _y , respectively; and any two adjacent ones of Y ₁ to Y ₄ are C and connected to Y ₉ and Y ₁₂ , respectively;
• L ₁ is selected from a single bond, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or combinations thereof;
• where _R , _R substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

In this embodiment, the expression that adjacent substituents R, R _x may optionally be connected to form a ring means that adjacent substituents R may be optionally connected to form a ring; further means that when multiple R _x are present on ring A, adjacent substituents R _x may optionally be linked to form a ring; further means that when multiple R _x are present on ring B, adjacent substituents R _x may optionally be linked to form a ring; further means that when multiple R _x are present on ring C, adjacent substituents R _x may optionally be linked to form a ring; and further means that adjacent substituents R and R _x may optionally be linked to form a ring. It is obvious to those skilled in the art that adjacent substituents R, R _x do not have to be linked to form a ring. In this case, adjacent substituents R are not connected to form a ring, and/or adjacent substituents R _x are not connected to form a ring, and/or adjacent substituents R and R _x are also not connected to form a ring Form a ring.

wobei A₁ bis A₃ bei jedem Auftreten gleich oder verschieden aus CR ausgewählt sind; und X₁ bis X₁₀ bei jedem Auftreten gleich oder verschieden aus CR_x ausgewählt sind; wobei R und R_x bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt sind, bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, einer Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon; und
wobei benachbarte Substituenten R, R_x gegebenenfalls verbunden sein können, dass sie einen Ring ausbilden.According to an embodiment of the present disclosure, H has a structure represented by Formula 1-a:

where A ₁ to A ₃ are selected equally or differently from CR on each occurrence; and X ₁ to X ₁₀ are selected equally or differently from CR _x on each occurrence; where R and _R with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, one carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and
wherein adjacent substituents R, R _x can optionally be connected to form a ring.

In this embodiment, the expression that adjacent substituents R, R _x may optionally be connected to form a ring means that adjacent substituents R may be optionally connected to form a ring; further means that adjacent substituents R _x in X ₁ to X ₃ may optionally be connected to form a ring; further means that adjacent substituents R _x in X ₄ to X ₆ may optionally be linked to form a ring; further means that adjacent substituents R _x in X ₇ to X ₁₀ may optionally be linked to form a ring; and is further intended to mean that adjacent substituents R _x , R and R _x may optionally be linked to form a ring. For example, adjacent substituents in A ₁ and X ₃ and/or A ₃ and X ₁₀ , and/or X ₆ and X ₇ may optionally be linked to form a ring. It will be apparent to those skilled in the art that adjacent substituents R and _Rx need not be linked to form a ring. In this case, adjacent substituents R are not connected to form a ring, and/or adjacent substituents R _x are not connected to form a ring, and/or adjacent substituents R and R _x are also not connected to form a ring Form a ring.

According to one embodiment of the present disclosure, R and _R Arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, substituted or unsubstituted amino of 0 to 20 carbon atoms, a cyano group, an isocyano group, a sulfanyl group, and combinations thereof; and adjacent substituents R, Rx may optionally be connected to form a ring.

In this embodiment, the expression that adjacent substituents R, R _x may optionally be connected to form a ring means that adjacent substituents R may be optionally connected to form a ring; further means that adjacent substituents R _x in X ₁ to X ₃ may optionally be connected to form a ring; further means that adjacent substituents R _x in X ₄ to X ₆ may optionally be linked to form a ring; further means that adjacent substituents R _x in X ₇ to X ₁₀ may optionally be linked to form a ring; and further means that adjacent substituents R _x , R and R _x may optionally be connected to form a ring. For example, adjacent substituents in A ₁ and X ₃ and/or A ₃ and X ₁₀ and/or X ₆ and X ₇ may optionally be linked to form a ring. It will be apparent to those skilled in the art that adjacent substituents R and _Rx need not be linked to form a ring. In this case, adjacent substituents R are not connected to form a ring, and/or adjacent substituents R _x are not connected to form a ring, and/or adjacent substituents R and R _x are also not connected to form a ring Form a ring.

According to an embodiment of the present disclosure, in Formula 1-a, at least one of R and _R

According to an embodiment of the present disclosure, in formula 1-a, at least one of R and R _x is selected from deuterium, phenyl, biphenyl or pyridyl.

According to one embodiment of the present disclosure, in formula 1-a for adjacent substituents R in A ₁ to A ₃ , adjacent substituents R _x in X ₁ to X ₃ , adjacent substituents R _x in X _a to X ₆ and adjacent substituents R _x in X ₇ to X ₁₀ at least one of these groups of adjacent substituents is connected to form a ring.

In this embodiment, the expression that at least one group of these groups of adjacent substituents is connected to form a ring means that for groups of adjacent substituents present in Formula 1-a, for example two adjacent substituents R in A ₁ and A ₂ , two adjacent Substituents R in A ₂ and A ₃ , two adjacent substituents R _x in X ₁ and X ₂ , two adjacent substituents R _x in X ₂ and X ₃ , two adjacent substituents R _x in X ₄ and X ₅ , two adjacent substituents R _x in X ₅ and X ₆ , two adjacent substituents R _x in X ₇ and X _{8 , two} adjacent substituents _{R x in X 8 and} connected to a ring.

According to an embodiment of the present disclosure, H is selected from the group consisting of the following structures:

In this embodiment, * represents the position at which H is bound to L ₁ .

wobei Y bei jedem Auftreten gleich oder verschieden aus CR_y ausgewählt ist;
wobei R_y bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt ist, bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, einer Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon.According to an embodiment of the present disclosure, E has a structure represented by one of Formulas 2-a to 2-f:

where Y is selected identically or differently from CR _y on each occurrence;
where R _y in each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

In this embodiment, * represents the position at which E is bound to L ₁ .

wobei Y bei jedem Auftreten gleich oder verschieden aus CR_y ausgewählt ist;
wobei R_y bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt ist, bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen und Kombinationen davon.According to an embodiment of the present disclosure, E has a structure represented by one of Formulas 2-a to 2-f:

where Y is selected identically or differently from CR _y on each occurrence;
where R _y in each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, and combinations thereof.

In this embodiment, * represents the position at which E is bound to L ₁ .

wobei Y bei jedem Auftreten gleich oder verschieden aus CR_y ausgewählt wird; wobei R_y bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt wird, bestehend aus: Wasserstoff, Deuterium, Halogen, Phenyl, Biphenyl, Naphthyl, 4-Cyanophenyl, Dibenzofuryl, Dibenzothienyl, Triphenylen, Carbazolyl, 9-Phenylcarbazolyl, 9,9-Dimethylfluorenyl, Pyridyl oder Phenylpyridyl.According to an embodiment of the present disclosure, E has a structure represented by one of Formulas 2-a to 2-f:

where Y is selected equally or differently from CR _y on each occurrence; where R _y is selected identically or differently at each occurrence from the group consisting of: hydrogen, deuterium, halogen, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuryl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9- Dimethylfluorenyl, pyridyl or phenylpyridyl.

In this embodiment, * represents the position at which E is bound to L ₁ .

According to one embodiment of the present disclosure, Y in the 6-membered aza ring in the structure represented by Formula 2-a to Formula 2-f is selected from CR _y and R _y is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms.

According to one embodiment of the present disclosure, Y in the 6-membered aza ring in the structure represented by Formula 2-a to Formula 2-f is selected from CR _y and R _y is selected from phenyl, biphenyl, naphthyl, 4-cyanophenyl, Dibenzofuryl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl or phenylpyridyl are selected.

According to an embodiment of the present disclosure, E is selected from the group consisting of the following structures:

In this embodiment, * represents the position at which E is bound to L ₁ .

According to one embodiment of the present disclosure, L ₁ is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene and thienylene.

According to an embodiment of the present disclosure, L ₁ is selected from the group consisting of the following structures:

In this embodiment, * represents the position where L ₁ is bound to E and H.

According to one embodiment of the present invention, the compound has a structure of HL ₁ -E, where H is selected from the group consisting of H-1 to H-95, L ₁ is selected from the group consisting of L-0 to L-25, and E is selected from the group consisting of E-1 to E-45.

According to one embodiment of the present invention, the compound has a structure of HL ₁ -E, where H is selected from the group consisting of H-1 to H-116, L ₁ is selected from the group consisting of L-0 to L-25, and E is selected from the group consisting of E-1 to E-159.

According to one embodiment of the present invention, the compound is selected from the group consisting of Compound 1-1 to Compound 1-421, the specific structures of Compound 1-1 to Compound 1-421 being recited in claim 12.

According to one embodiment of the present invention, the compound is selected from the group consisting of Compound 1-1 to Compound 1-601, the specific structures of Compound 1-1 to Compound 1-601 being recited in claim 12.

• eine Anode,
• eine Kathode und
• eine organische Schicht, die zwischen der Anode und der Kathode angeordnet ist, wobei die organische Schicht eine Verbindung mit einer Struktur von H-L1-E umfasst;
• wobei H eine durch Formel 1 dargestellte Struktur aufweist:
  
• wobei in Formel 1 A_1, A₂ und A₃ bei jedem Auftreten gleich oder verschieden aus CR ausgewählt sind; und der Ring A, der Ring B und der Ring C bei jedem Auftreten gleich oder verschieden aus einem aromatischen Ring mit 6 bis 18 Kohlenstoffatomen oder einem heteroaromatischen Ring mit 3 bis 18 Kohlenstoffatomen ausgewählt sind;
• R_x eine Monosubstitution, Mehrfachsubstitution oder Nichtsubstitution darstellt; und
• benachbarte Substituenten R, R_x gegebenenfalls verbunden sein können, dass sie einen Ring ausbilden;
• wobei E eine durch Formel 2 dargestellte Struktur aufweist:
  
• wobei Y₁ bis Y₁₂ bei jedem Auftreten gleich oder verschieden aus N, C oder CR_y ausgewählt sind; und beliebige zwei von Y₅ bis Y₈ aus Stickstoff ausgewählt sind, die anderen zwei von Y₅ bis Y₈ bei jedem Auftreten gleich oder verschieden aus C oder CR_y ausgewählt sind; und beliebige benachbarte zwei von Y₁ bis Y₄ C sind und mit Y₉ bzw. Y₁₂ verbunden sind;
• L₁ aus einer Einfachbindung, substituiertem oder unsubstituiertem Arylen mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroarylen mit 3 bis 30 Kohlenstoffatomen oder Kombinationen davon ausgewählt ist;
• wobei R, R_x und R_y bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt sind, bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, einer Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon.

According to an embodiment of the present disclosure, there is disclosed an electroluminescent device comprising:

• an anode,
• a cathode and
• an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of H-L1-E;
• where H has a structure represented by Formula 1:
  
• where in Formula 1 A _1, A ₂ and A ₃ are selected identically or differently from CR in each occurrence; and the ring A, the ring B and the ring C are in each occurrence identically or differently selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms;
• R _x represents monosubstitution, multiple substitution or non-substitution; and
• adjacent substituents R, R _x can optionally be connected so that they form a ring;
• where E has a structure represented by Formula 2:
  
• where Y ₁ to Y ₁₂ are selected identically or differently from N, C or CR _y on each occurrence; and any two of Y ₅ to Y ₈ are selected from nitrogen, the other two of Y ₅ to Y ₈ are selected equally or differently from C or CR _y on each occurrence; and any adjacent two of Y ₁ to Y ₄ are C and connected to Y ₉ and Y ₁₂ , respectively;
• L ₁ is selected from a single bond, substituted or unsubstituted arylene of 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene of 3 to 30 carbon atoms, or combinations thereof;
• where _R , _R or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

In this embodiment, the expression that adjacent substituents R and R _x may optionally be connected to form a ring means that adjacent substituents R may be optionally connected to form a ring; further means that when multiple R _x are present on ring A, adjacent substituents R _x may optionally be linked to form a ring; further means that when multiple R _x are present on ring B, adjacent substituents R _x may optionally be linked to form a ring; further means that when multiple R _x are present on ring C, adjacent substituents R _x may optionally be linked to form a ring; and further means that adjacent substituents R and R _x may optionally be linked to form a ring. It will be apparent to those skilled in the art that adjacent substituents R and Rx need not be linked to form a ring. In this case, adjacent substituents R are not bonded to form a ring, adjacent substituents R _x are not bonded to form a ring, and adjacent substituents R and R _x are also not bonded to form a ring.

According to an embodiment of the present disclosure, the organic layer in the device is a light emitting layer and the compound is a host material.

According to an embodiment of the present disclosure, the light-emitting layer in the device further comprises a phosphorescent material.

wobei
R_a, Rb und Rc Monosubstitutionen, Mehrfachsubstitutionen oder Nichtsubstitutionen darstellen können und bei jedem Auftreten gleich oder verschieden sein können;
X_b aus der Gruppe ausgewählt ist, bestehend aus: O, S, Se, NR_N1 und CR_C1 R_C2;
X_c und X_d bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt sind,bestehend aus: O, S, Se und NR_N2;
R_a, R_b, R_c, R_N1, R_N2, R_C1 und R_C2 bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt sind bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, einer Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon; und
benachbarte Substituenten in der Struktur des Liganden optional zu einem Ring verbunden werden können.According to an embodiment of the present disclosure, the phosphorescent material in the device is a metal complex comprising at least one ligand, the ligand comprising one of the following structures:

where
R _a , Rb and Rc may represent monosubstitutions, multiple substitutions or non-substitutions and may be the same or different in each occurrence;
X _b is selected from the group consisting of: O, S, Se, NR _N1 and CR _C1 R _C2 ;
_{X c and}
R _a , R _b , R _c , R _N1 , R _N2 , R _C1 and R _C2 are selected in each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substitute tem or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and
neighboring substituents in the structure of the ligand can optionally be connected to form a ring.

In this embodiment, the expression means that adjacent substituents can optionally be connected to form a ring, that for groups of adjacent substituents, for example two substituents R _a , two substituents R _b , two substituents R _c , substituents R _a and R _b , substituents R _a and R _e , substituents R _b and R _c , the substituents R _a and R _N1 , the substituents R _b and R _N1 , the substituents R _a and R _C1 , the substituents R _a and R _C2 , the substituents R _b and R _C1 , the substituents R _b and R _C2 , the substituents R _a and R _N2 , the substituents R _b and R _N2 and the substituents R _C1 and R _C2 , one or more groups of these groups of substituents can be connected to one another, that they form a ring. Likewise, these substituents do not need to be linked to form a ring.

wobei R₁ bis R₇ jeweils unabhängig voneinander aus der Gruppe ausgewählt sind, bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, eine Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon.According to an embodiment of the present disclosure, the phosphorescent material in the device is a metal complex comprising at least one ligand, the ligand having the following structure:

where R ₁ to R ₇ are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

wobei mindestens eins von R₁ bis R₃ ausgewählt ist aus substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen oder Kombinationen davon; und/oder mindestens ein oder zwei von R₄ bis R₆ ausgewählt sind aus substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen oder Kombinationen davon.According to an embodiment of the present disclosure, the phosphorescent material in the device is a metal complex comprising at least one ligand, the ligand having the following structure:

wherein at least one of R ₁ to R ₃ is selected from substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1 to 20 carbon atoms, or combinations thereof; and/or at least one or two of R ₄ to R ₆ are selected from substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, or combinations thereof.

wobei mindestens zwei von R₁ bis R₃ ausgewählt sind aus substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen oder Kombinationen davon; und/oder mindestens ein oder zwei von R₄ bis R₆ ausgewählt sind aus substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen oder Kombinationen davon.According to an embodiment of the present disclosure, the phosphorescent material in the device is a metal complex comprising at least one ligand, the ligand having the following structure:

wherein at least two of R ₁ to R ₃ are selected from substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1 to 20 carbon atoms, or combinations thereof; and/or at least one or two of R ₄ to R ₆ are selected from substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, or combinations thereof.

wobei mindestens zwei von R₁ bis R₃ bei jedem Auftreten gleich oder verschieden ausgewählt sind aus substituiertem oder unsubstituiertem Alkyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 2 bis 20 Kohlenstoffatomen oder Kombinationen davon; und/oder mindestens zwei von R₄ bis R₆ bei jedem Auftreten gleich oder verschieden ausgewählt sind aus substituiertem oder unsubstituiertem Alkyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 2 bis 20 Kohlenstoffatomen oder Kombinationen davon.According to an embodiment of the present disclosure, the phosphorescent material in the device is a metal complex comprising at least one ligand, the ligand having the following structure:

wherein at least two of R ₁ to R ₃ are selected identically or differently on each occurrence from substituted or unsubstituted alkyl with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 2 to 20 carbon atoms, or combinations thereof ; and/or at least two of R ₄ to R ₆ are selected identically or differently on each occurrence from substituted or unsubstituted alkyl with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 2 to 20 carbon atoms or Combinations of these.

According to an embodiment of the present disclosure, the phosphorescent material in the device is an Ir, Pt or Os complex.

According to an embodiment of the present disclosure, the phosphorescent material in the device is an Ir complex and has a structure of Ir(L _a )(L _b )(L _e ); where L _a , L _b and L _c are selected identically or differently from one of the above ligands on each occurrence.

wobei X_f bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt ist, bestehend aus: O, S, Se, NR_N3 und CR_C3R_C4;
wobei X₆ CR_d oder N ist;
R_a, R_b und R_e Monosubstitutionen, Mehrfachsubstitutionen oder Nichtsubstitutionen darstellen können und bei jedem Auftreten gleich oder verschieden sein können;
R_a, R_b, R_c, R_d, R_N3, R_C3 und R_C4 bei jedem Auftreten gleich oder verschieden aus der Gruppe ausgewählt sind, bestehend aus: Wasserstoff, Deuterium, Halogen, substituiertem oder unsubstituiertem Alkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Cycloalkyl mit 3 bis 20 Ringkohlenstoffatomen, substituiertem oder unsubstituiertem Heteroalkyl mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylalkyl mit 7 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkoxy mit 1 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryloxy mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkenyl mit 2 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Aryl mit 6 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Heteroaryl mit 3 bis 30 Kohlenstoffatomen, substituiertem oder unsubstituiertem Alkylsilyl mit 3 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Arylsilyl mit 6 bis 20 Kohlenstoffatomen, substituiertem oder unsubstituiertem Amino mit 0 bis 20 Kohlenstoffatomen, einer Acylgruppe, einer Carbonylgruppe, einer Carbonsäuregruppe, einer Estergruppe, einer Cyanogruppe, einer Isocyanogruppe, einer Sulfanylgruppe, einer Sulfinylgruppe, einer Sulfonylgruppe, einer Phosphinogruppe und Kombinationen davon.According to an embodiment of the present disclosure, the phosphorescent material in the device is selected from the group consisting of the following structures:

where X _f in each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR _N3 and CR _C3 R _C4 ;
where X ₆ CR _d or N;
R _a , R _b and R _e may represent monosubstitutions, multiple substitutions or non-substitutions and may be the same or different in each occurrence;
R _a , R _b , R _c , R _d , R _N3 , R _C3 and R _C4 in each occurrence are identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms , substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms , substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms , substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

According to another embodiment of the present disclosure, there is further disclosed a compound formulation comprising a compound having a structure of HL ₁ -E, wherein the specific structure of the compound is as shown in any of the embodiments described above.

Combination with other materials

The materials described in the present disclosure for a particular layer in an organic light emitting device may be used in combination with various other materials present in the device. The combinations of these materials are in the US Patent Application No. 20160359122 described in more detail in paragraphs 0132-0161, which is incorporated herein by reference in its entirety. The materials described or referred to in the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one skilled in the art can readily consult the literature to identify other materials , which can be useful in combination.

The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is discussed in detail in paragraphs 0080-0101 of the US Patent Application No. 20150349273 described, which is incorporated herein by reference in its entirety. The materials described or referred to in the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one skilled in the art can readily consult the literature to identify other materials , which can be useful in combination.

In the material synthesis embodiments, all reactions were carried out under nitrogen protection unless otherwise stated. All reaction solvents were anhydrous and used as obtained from commercial sources. Synthetic products have been structurally confirmed and tested for their properties using one or more common devices (including, but not limited to, BRUKER Nuclear Magnetic Resonance Instrument, SHIMADZU Liquid Chromatography, SHIMADZU Liquid Chromatography Mass Spectrometer, SHIMADZU Gas Chromatography Mass Spectrometer, SHIMADZU Differential Scanning Calorimeter, Fluorescence Spectrophotometer of SHANGHAI LENGGUANG TECH., electrochemical workstation manufactured by WUHAN CORRTEST and sublimation machine manufactured by ANHUI BEQ, etc.) by methods well known to those skilled in the art. In the embodiments of the device, the characteristics of the device were also measured using conventional technical devices (including but not limited to the evaporator manufactured by ANGSTROM ENGINEERING, the optical inspection system manufactured by SUZHOU FATAR, the life test system manufactured by SUZHOU FATAR and that manufactured by BEIJING ELLITOP ellipsometers, etc.) according to methods well known to those skilled in the art. Since the use of the above-mentioned devices, the test methods and other related contents are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without interference, so the above-mentioned related contents will not be further described in the present disclosure.

Example of material synthesis

The method of producing a compound in the present disclosure is not limited here. Typically, the following compounds are used as examples without limitations, and synthetic routes and production methods thereof are described below.

Synthesis Example 1: Synthesis of Compound 1-1

Step 1: Synthesis of intermediate 1

Under nitrogen protection, 2-bromo-3-chloronitrobenzene (100 g, 425.5 mmol), 2-aminophenylboronic acid pinacol ester (102 g, 468.1 mmol), tetrakis (triphenylphosphine) palladium (4.9 g, 4.25 mmol), Potassium carbonate (115 g, 852 mmol), toluene (1000 ml), water (200 ml) and ethanol (200 ml) were introduced into a three-necked flask and reacted at 100 °C for 48 h. After the reaction was completed, the reaction solution was cooled to room temperature, concentrated to remove the solvents, and distilled water was added. The mixture was extracted with ethyl acetate. The organic phases were washed with water, dried over anhydrous magnesium sulfate, concentrated to remove the solvent and purified by column chromatography (PE/EA = 4:1) to obtain intermediate 1 as a yellow oil (90 g, yield: 85%).

Step 2: Synthesis of intermediate 2

Intermediate 1 (90 g, 363 mmol) and acetonitrile (1000 mL) were each introduced into a three-necked flask. P-toluenesulfonic acid (193.2 g, 1088 mmol) was added in portions at 0 °C and stirred for 30 min. At this temperature, a mixed aqueous solution of sodium nitrite (69 g, 726 mmol) and potassium iodide (150.6 g, 907 mmol) was slowly added dropwise. After the dropwise addition was completed, the mixture was slowly warmed to room temperature and reacted for 12 h. After the reaction was completed, a saturated aqueous solution of sodium thiosulfate was added dropwise to quench the reaction. The reaction solution was concentrated and diluted with water. The mixed solution was extracted three times with ethyl acetate. The organic phases were dried over anhydrous sodium sulfate and concentrated to remove solvents. The mixture was isolated by column chromatography (PE/DCM=10/1) to obtain intermediate 2 as a yellow solid (85 g, yield: 65%).

Step 3: Synthesis of intermediate 4

Under nitrogen protection, intermediate 2 (20 g, 55.7 mmol), intermediate 3 (24.5 g, 83.6 mmol), tetrakis(triphenylphosphine)palladium (1.9 g, 1.67 mmol), potassium carbonate ( 15.4 g, 111.4 mmol), tetrahydrofuran (500 ml), water (100 ml) and ethanol (100 ml) were introduced into a three-necked flask and reacted at 70 °C for 48 h. After the reaction was completed, the reaction solution was cooled to room temperature, concentrated to remove the solvents, and distilled water was added. The mixture was extracted with ethyl acetate. The organic phases were washed with water, dried over anhydrous magnesium sulfate, concentrated to remove the solvent, and purified by column chromatography (PE/EA = 4:1) to obtain intermediate 4 as a yellow solid (12 g, yield: 55%) .

Step 4: Synthesis of intermediate 5

Under nitrogen protection, intermediate 4 (12 g, 30.15 mmol), palladium acetate (338 mg, 1.5 mmol), tri-tert-butylphosphine (606 mg, 3.0 mmol), cesium carbonate (20 g, 60.3 mmol). mmol) and xylene (230 ml) were introduced into a three-necked flask and reacted at 140 °C for 10 h. After the reaction was completed, the reaction solution was cooled to room temperature, concentrated to remove the solvents, and distilled water was added. The mixture was extracted with ethyl acetate. The organic phases were washed with water, dried over anhydrous magnesium sulfate, concentrated to remove the solvent, and purified by column chromatography (PE/EA = 6:1) to obtain intermediate 5 as a yellow solid (9 g, yield: 80%). .

Step 5: Synthesis of intermediate 6

Under nitrogen protection, intermediate 5 (9 g, 24.9 mmol), triphenylphosphine (19.6 g, 74.7 mmol), and o-dichlorobenzene (o-DCB) (100 mL) were added to a three-necked flask and left for 12 h 200 °C implemented. After the completion of the reaction, the reaction solution was concentrated to remove the solvent, and the crude product was isolated by column chromatography to obtain intermediate 6 as a yellow solid (7 g, yield: 85%).

Step 6: Synthesis of Compound 1-1

Under nitrogen protection, intermediate 6 (3 g, 9.1 mmol), intermediate 7 (2.64 g, 9.1 mmol), cesium carbonate (5.9 g, 18.2 mmol) and DMF (60 mL) were added introduced a three-necked flask and reacted at 60 °C for 16 h. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added and filtered to obtain a solid. The solid was washed three times with ethanol or ethyl acetate. The crude product was washed twice with pentanone and toluene, respectively, to obtain compound 1-1 as a yellow solid (3.3 g, yield: 56%). The product was confirmed as the target product with a molecular weight of 584.2.

Synthesis Example 2: Synthesis of Compound 1-253

Step 1: Synthesis of compound 1-253

Under nitrogen protection, intermediate 6 (1 g, 3.03 mmol), intermediate 8 (880 mg, 3.03 mmol), 4-(dimethylamino)pyridine (DMAP) (366 mg, 3.03 mmol), cesium carbonate ( 2.0 g, 6.06 mmol) and DMF (30 ml) were introduced into a three-necked flask and reacted at 120 °C for 6 h. After the completion of the reaction, the reaction solution was cooled to room temperature, distilled water was added to precipitate a solid, and filtered to collect the solid. The solid was purified by column chromatography (PE/EA = 2:1) to obtain compound 1-253 as a yellow solid (1.3 g, 76%). The product was confirmed as the target product with a molecular weight of 584.2.

Synthesis Example 3: Synthesis of Compound 1-348

Step 1: Synthesis of compound 1-348

Under nitrogen protection, intermediate 6 (2 g, 6.06 mmol), intermediate 9 (1.8 g, 6.06 mmol), DMAP (733 mg, 6.06 mmol), cesium carbonate (3.9 g, 12 .12 mmol) and DMF (40 ml) were introduced into a three-necked flask and reacted at 120 °C for 6 h. After the completion of the reaction, the reaction solution was cooled to room temperature, distilled water was added to precipitate a solid, and filtered to collect the solid. The solid was purified by column chromatography (PE/EA = 2:1) to obtain compound 1-348 as a yellow solid (2.4 g, 68%). The product was confirmed as the target product with a molecular weight of 584.2.

Those skilled in the art will understand that the above preparation methods are merely illustrative. Those skilled in the art can obtain other interconnect structures of the present disclosure through modifications to the manufacturing methods.

Device example

Device example 1

First, a glass substrate was cleaned with an indium tin oxide (ITO) anode with a thickness of 120 nm and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a nitrogen-filled glovebox to remove moisture and then mounted on a substrate holder and inserted into a vacuum chamber. The organic layers indicated below were deposited sequentially by thermal vacuum evaporation on the ITO anode at a rate of 0.01 to 5 Å/s at a vacuum degree of about 10 ^-8 Torr. Compound HI was used as a hole injection layer (HIL) with a thickness of 100 Å. Compound HT was used as a hole transport layer (HTL) with a thickness of 400 Å. The compound EB was created as electrons Blocking layer (EBL) with a thickness of 50 Å was used. Subsequently, the compound 1-1 of the present disclosure as a host and the compound RD as a dopant were co-deposited as an emission layer (EML) with a thickness of 400 Å. The compound HB was used as a hole blocking layer (HBL) with a thickness of 50 Å. On the HBL, the compound ET and 8-hydroxyquinolinolato-lithium (Liq) were co-deposited as an electron transport layer (ETL) with a thickness of 350 Å. Finally, 8-hydroxyquinolinolato lithium (Liq) was deposited with a thickness of 10 Å as an electron injection layer (EIL) and Al with a thickness of 1200 Å as a cathode. The device was transferred back to the glovebox and encapsulated with a glass lid to complete the device.

Device comparison example 1

The implementation mode in Device Comparative Example 1 was the same as that in Device Example 1 except that Compound 1-1 of the present disclosure in the emission layer (EML) was replaced by Compound A to serve as a host.

Detailed structures and thicknesses of the layers of the devices are shown in the following table. A layer using more than one material is obtained by doping different compounds in their weight ratios as described. Table 1 Device structures in the device example and in the comparative example Device ID HIL HTL EBL EML (400 Ä) HBL ETL host dopant example 1 Connection HI Connection HT Connection EB Compound 1-1 (97%) Compound RD (3%) Connection HB Connection ET:Liq (40:60) (100 Å) (400 Å) (50 Å) (50 Ä) (350 Å) Comparative example 1 Connection HI Connection HT Connection EB Compound A (97%) Compound RD (3%) Connection HB Connection ET:Liq (40:60) (100 Å) (400 Å) (50 Å) (50 Ä) (350 Å)

The structures of the materials used in the devices are shown as follows:

The current efficiency (CE), maximum wavelength (λmax), and external quantum efficiency (EQE), measured at 15 mA/cm ² , are listed in Table 2. Table 2 Device data Device ID At 15 mA/ ^cm2 λ _max (nm) CE [cd/A] EQE (%) example 1 628 16 20.35 Comparative example 1 627 15 18.8

Discussion:

As shown in Table 2, the EQE of Example 1 measured at a current density of 15 mA/cm ² is 20.35%, which is 8% higher than the EQE (18.8%) of Comparative Example 1; the CE of Example 1 is slightly higher than the CE of Comparative Example 1; λ _max is essentially the same in Example 1 and Comparative Example 1; however, the light emission efficiency of Example 1 was greatly improved. That is, the compound of the present disclosure comprising a hole transport unit that condenses of indole and pyrrole with an azamacrocycle and bound with an electron transport unit of benzoquinazoline or benzoquinoxaline and similar structures thereof has better electron transport stability than compound A in which an electron transport unit of quinazoline is bound. The compound of the present disclosure can make the hole transport and electron transport in the emission layer reach a more balanced state and thus has significantly improved efficiency.

Device example 2

The implementation mode in the Device Comparative Example 2 was the same as that in the Device Example 1 except that the compound 1-1 of the present disclosure in the emission layer (EML) was replaced by the compound 1-253 to serve as a host together is deposited with the compound RD (in a weight ratio of 98:2).

Device example 3

The implementation mode in the Device Comparative Example 3 was the same as that in the Device Example 1 except that the compound 1-1 of the present disclosure in the emission layer (EML) was replaced by the compound 1-348 to serve as a host together is deposited with the compound RD (in a weight ratio of 98:2).

Device comparison example 2

The implementation mode in the Device Comparative Example 2 was the same as that in the Device Example 1 except that the compound 1-1 of the present disclosure in the emission layer (EML) was replaced by the compound B to serve as a host together with the Compound RD (in a weight ratio of 98:2) is deposited.

Detailed structures and thicknesses of the layers of the devices are shown in the following table. A layer using more than one material is obtained by doping different compounds in their weight ratios as described. Table 3 Device structures in the device examples and the comparative example Device ID HIL HTL EBL EML (400 Ä) HBL ETL host dopant Example 2 Connection HI Connection HT Connection EB Connection 1-253 Compound RD (2%) Connection HB Connection ET:Liq (100 Å) (400 Å) (50 Ä) (98%) (50 Ä) (40:60) (350 Å) Example 3 Connection HI Connection HT Connection EB Connection 1-348 Compound RD (2%) Connection HB Connection ET:Liq (100 Å) (400 Å) (50 Ä) (98%) (50 Ä) (40:60) (350 Å) Comparative example 2 Connection HI Connection HT Connection EB Compound B (98%) Compound RD (2%) Connection HB Compound ET:Liq (40: (100 Å) (400 Å) (50 Ä) (50 Å) 60) (350 Å)

The structures of the new materials used in the devices are shown as follows:

The current efficiency (CE) and maximum wavelength (λ _max ), measured at 15 mA/cm ² , and lifetime, measured at 80 mA/cm ² , are shown in Table 4. Table 4: Device data Device ID At 15 mA/ ^cm2 At 80 mA/ ^cm2 λ _max (nm) CE [cd/A] LT97 (h) Example 2 628 19 65 Example 3 625 18 67 Comparative example 2 625 19 41

Discussion:

As shown in Table 4, Example 2 and Example 3 have substantially the same power efficiency as Comparative Example 2. However, the life of Example 2 is 65 hours, which is 58% longer than the life of Comparative Example 2, and the life of Example 3 was improved by up to 63% over the life of Comparative Example 2. This proves that the compound of the present disclosure can significantly improve the life of the device compared to the prior art compound B.

In summary, the compound disclosed in the present disclosure, which includes a hole transport unit formed by condensing indole and pyrrole with an azamacrocycle and bonded with an electron transport unit of benzoquinazoline or benzoquinoxaline and similar structures thereof, exhibits better electron transport stability than Compound A and compound B in which an electron transport unit made of quinazoline or quinoxaline is bound. The compound of the present disclosure can cause hole transport and electron transport in the emitting layer to reach a more balanced state, and thus exhibit significant improvements in efficiency and/or lifetime.

It is to be understood that the various embodiments described herein are examples and are not intended to limit the scope of the present disclosure. Therefore, it will be apparent to those skilled in the art that the present disclosure, as claimed, may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be substituted for other materials and structures without departing from the spirit of the present disclosure. It is understood that various theories as to why the present disclosure works are not limiting.

Claims (21)

Compound with a structure of HL ₁ -E; where H has a structure represented by Formula 1:

where in Formula 1 A _1, A ₂ and A ₃ are selected identically or differently from CR in each occurrence; and the ring A, the ring B and the ring C are in each occurrence identically or differently selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms; R _x represents monosubstitution, multiple substitution or non-substitution; and adjacent substituents R, R _x may optionally be linked to form a ring; where E has a structure represented by Formula 2:

where Y ₁ to Y ₁₂ are selected identically or differently from N, C or CR _y on each occurrence; and any two of Y ₅ to Y ₈ are selected from nitrogen, the other two of Y ₅ to Y ₈ are selected from C and CR _y , respectively; and any two adjacent ones of Y ₁ to Y ₄ are C and connected to Y ₉ and Y ₁₂ , respectively; L ₁ is selected from a single bond, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or combinations thereof; where _R , _R substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof. Connection to Claim 1 , where H has a structure represented by Formula 1-a:

where A ₁ to A ₃ are selected equally or differently from CR on each occurrence; and X ₁ to X ₁₀ are selected equally or differently from CR _x on each occurrence; where R and _R with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, one carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and wherein adjacent substituents R, R _x may optionally be linked to form a ring. Connection to Claim 2 , where R and _R Alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted Amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, a sulfanyl group, and combinations thereof; and adjacent substituents R, Rx may optionally be connected to form a ring. Connection to Claim 2 or 3 , wherein at least one of R and R _x is selected from deuterium, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms; wherein preferably at least one of R and R _x is selected from deuterium, phenyl, biphenyl or pyridyl. Connection to Claim 2 or 3 , where for adjacent substituents R in A ₁ to A ₃ , adjacent substituents R _x in X ₁ to X ₃ , adjacent substituents R _x in X _a to X ₆ and adjacent substituents R _x in X _{7 to} Substitutents are connected to form a ring. Connection according to one of the Claims 1 until 5 , where the H is selected from the group consisting of the following structures:

Connection to Claim 1 , where E has a structure represented by one of the formulas 2-a to 2-f:

where Y is selected identically or differently from CR _y on each occurrence; where R _y is selected in each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, one carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; wherein R _y is preferably selected at each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, and combinations thereof; more preferably R _y is selected identically or differently for each occurrence from the group consisting of: hydrogen, deuterium, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuryl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl and phenylpyridyl. Connection to Claim 7 , wherein Y in the 6-membered aza ring in the structure represented by Formula 2-a to Formula 2-f is selected from CR _y , and R _y is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl is selected from 3 to 30 carbon atoms; where R _y is preferably selected from phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuryl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridyl or phenylpyridyl. Connection to Claim 1 or 7 , where E is selected from the group consisting of the following structures:

Connection to Claim 1 , where L ₁ is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene and thienylene; where L ₁ is preferably selected from the group consisting of the following structures:

Connection according to one of the Claims 1 until 10 , wherein the compound has a structure of HL ₁ -E, where H is selected from the group consisting of H-1 to H-116, L ₁ is selected from the group consisting of L-0 to L-25 and E is selected from the group consisting of E-1 to E-159. Connection according to one of the Claims 1 until 11 , where the compound is selected from the group consisting of the following structures:

An electroluminescent device comprising: an anode, a cathode and an organic layer disposed between the anode and the cathode, the organic layer containing the compound according to one of the Claims 1 until 12 includes. Electroluminescent device Claim 13 , where the organic layer is a light-emitting layer and the compound is a host material. Electroluminescent device Claim 14 , wherein the light-emitting layer further comprises a phosphorescent material. Electroluminescent device Claim 15 , wherein the phosphorescent material is a metal complex comprising at least one ligand, the ligand comprising one of the following structures:

where R _a , Rb and Rc may represent monosubstitutions, multiple substitutions or non-substitutions and may be the same or different in each occurrence; X _b is selected from the group consisting of: O, S, Se, NR _N1 and CR _C1 R _C2 ; _{X c and} R _a , R _b , R _c , R _N1 , R _N2 , R _C1 and R _C2 are selected in each occurrence, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and adjacent substituents in the structure of the ligand may optionally be linked to form a ring. Electroluminescent device Claim 16 , wherein the metal complex comprises at least one ligand, the ligand having the following structure:

where R ₁ to R ₇ are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; wherein at least one or two of R ₁ to R ₃ are preferably selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1 to 20 carbon atoms, or combinations thereof; and/or at least one or two of R4 to R6 are selected from substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1 to 20 carbon atoms, or combinations thereof; at least two of R ₁ to R ₃ in each occurrence are preferably selected identically or differently from substituted or unsubstituted alkyl with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 2 to 20 carbon atoms or combinations thereof ; and/or at least two of R ₄ to R ₆ are selected identically or differently on each occurrence from substituted or unsubstituted alkyl with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 2 to 20 carbon atoms or Combinations of these. Electroluminescent device Claim 16 or 17 , where the phosphorescent material is an Ir, Pt or Os complex. Electroluminescent device Claim 18 , wherein the phosphorescent material is an Ir complex and has a structure of Ir(L _a )(L _b )(L _c ); where L _a , L _b and L _c are selected identically or differently from one of the above ligands on each occurrence. Electroluminescent device according to one of the Claims 15 until 19 , wherein the phosphorescent material is selected from the group consisting of the following structures:

where X _f in each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR _N3 and CR _C3 R _C4 ; where X _e CR _d or N; R _a , R _b and R _e may represent monosubstitutions, multiple substitutions or non-substitutions and may be the same or different in each occurrence; R _a , R _b , R _c , R _d , R _N3 , R _C3 and R _C4 in each occurrence are identically or differently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms , substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms , substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl with 3 to 20 carbon atoms, substi substituted or unsubstituted arylsilyl with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and Combinations of these. Compound formulation containing the compound according to one of the Claims 1 until 12 .

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