Electroactive compound and electroluminescent device comprising the same

Abstract

Provided are an electroactive compound and an electroluminescent device comprising the same. A composition comprising a mixture of a first compound and a second compound, the first compound having a different chemical structure than the second compound; the first compound and the second compound have a molecular weight of between 300 and 1000; the first compound and the second compound have a glass transition temperature (Tg) greater than 105 DEG C; the first compound and the second compound each comprise one or more arylamine groups; the first compound has a concentration C1 in the mixture; the second compound has a concentration C2 in the mixture; c1 is between 1 wt.% and 99 wt.%; c2 is between 1 wt.% and 99 wt.%; the thin film formed from the first compound has spontaneous orientation polarization SOP-1; the thin film formed from the second compound has a spontaneous oriented polarization SOP-2; the absolute value of the difference between SOP-1 and SOP-2 is greater than or equal to 10 mV / nm.

Description

Technical Field

[0001] The present disclosure generally relates to arylamine compounds and their use in electronic devices. Background Art

[0002] Organic electronic devices that emit light, such as light-emitting diodes that make up a display, are present in many different types of electronic devices. In all such devices, an organic active layer is positioned between two electrical contact layers. At least one of these electrical contact layers is light-transmissive such that light can pass through the electrical contact layer. When a current is applied across the electrical contact layers, the organic active layer emits light through the light-transmissive electrical contact layer.

[0003] In recent years, such organic light-emitting (OLED) devices have become a mainstream display technology. The most common blue host materials used in commercial OLED devices are anthracene-based molecules, some of which incorporate oxygen atoms. These oxygen-containing molecules typically have a dipole moment of close to or greater than 1 Debye, and many oxygen-containing molecules form a polarized layer upon vapor deposition, where the negative end of the macroscopic dipole points towards the substrate. The manifestation of spontaneous orientation polarization (SOP) in OLED devices was first reported in 2000, at which time Berleb et al. (Organic Electronics 2000, 1(1) 41-47) observed hole injection that was linearly dependent on the thickness of the Alq 3 layer and explained these observations in terms of interfacial charges that inherently exist at the NPB|Alq3 interface. In 2002, Ito et al. (J. Appl. Phys. 2002, 92(12), 7306) found a similar thickness-dependent potential (referred to as the giant surface potential - GSP) on the surface of a vacuum-deposited Alq 3 film and proposed that Alq 3The spontaneous preferential orientation of molecules leads to the formation of macroscopic dipoles and bulk polarization. Subsequently, it was found that SOP in OLED devices can lead to charge accumulation at the interface and affect device operation (see, e.g., Kondakov et al., J. Appl. Phys. 2002, 93(2) 1108). In prior art blue fluorescent OLEDs, polarization in the emission layer (EML) causes charge accumulation at both the HTL / EML and ETL / EML interfaces before the device is turned on. This increase in charge density (especially at the EML / ETL interface) facilitates charge injection and reduces the device operation voltage. When compared to devices using a non-polar host material (pure aromatic hydrocarbon anthracene derivatives), the voltage reduction can exceed 0.5 V at 1000 nits, resulting in improved power efficiency. Additionally, the lower blue pixel operation voltage is beneficial in reducing lateral leakage and preventing color shift at low brightness in high-resolution OLED displays (see, e.g., Diethelm et al., J. Info. Disp. 2018, 19, 1). However, devices with a polarized EML typically show lower efficiency (especially at low brightness), presumably due to additional quenching of excitons caused by a greater density of holes near the recombination zone. Considering all the benefits of using a polarized EML in fluorescent blue devices, there is a continuing need to identify ways to restore device efficiency without eliminating SOP in the EML. Summary of the Invention

[0004] Provided is a composition comprising a mixture of a first arylamine compound and a second arylamine compound; a thin film comprising a first arylamine compound and a second arylamine compound; and an organic electronic device comprising an electron blocking layer comprising one or more arylamine compounds. Brief Description of the Drawings

[0005] Embodiments are illustrated in the drawings to enhance understanding of the concepts presented herein.

[0006] Figure 1 Illustration of an example of an organic electronic device comprising the layer structure described herein.

[0007] Figure 2 Illustration of another example of an organic electronic device comprising the layer structure described herein.

[0008] Figure 3 Illustration of another example of an organic electronic device comprising the layer structure described herein.

[0009] Figure 4Graph showing the relative OLED device efficiency including the device described herein as a function of the SOP of an electron blocking layer (EBL).

[0010] Those skilled in the art will understand that the objects in the figures are shown for simplicity and clarity and are not necessarily drawn to scale. For example, the dimensions of some of the objects in the figures may be exaggerated relative to other objects to help improve the understanding of the relevant embodiments.

[0011] The foregoing general description and the following detailed description are exemplary and explanatory only and do not limit the invention as defined by the appended claims. Detailed Description

[0012] Numerous aspects and embodiments are described herein, and these aspects and embodiments are exemplary only and not limiting. After reading this specification, those skilled in the art will understand that other aspects and embodiments are possible without departing from the scope of the invention.

[0013] From the following detailed description and from the claims, other features and benefits of any one or more of the embodiments will be apparent. The detailed description first presents definitions and clarifications of terms, followed by mixtures of arylamine compounds; thin films; organic electronic devices; and finally examples.

[0014] 1. Definition and clarification of terms

[0015] Before presenting the details of the following embodiments, some terms are defined or clarified.

[0016] As used throughout this specification, unless the context clearly indicates otherwise, the following abbreviations shall have the following meanings: °C = degrees Celsius; g = grams; nm = nanometers, μm = microns (micron / micrometer); mm = millimeters; sec. = seconds; and min = minutes. Unless otherwise indicated, all amounts are weight percentages ("wt.%" or "weight %") and all ratios are molar ratios. All numerical ranges are inclusive of the end values and can be combined in any order, except where such numerical ranges are clearly limited to a total of 100%. Unless otherwise indicated, the molecular weights of all polymers and oligomers are weight average molecular weights ("Mw") in g / mol or Daltons and are determined using gel permeation chromatography compared to polystyrene standards.

[0017] Unless the context clearly indicates otherwise, the articles "a / an" and "the" refer to the singular and plural. As used herein, the term "and / or" includes any and all combinations of one or more of the related items.

[0018] As used herein, R, R a , R b , R’, R” and any other variables are general names and may be the same as or different from those defined in the formula.

[0019] As used herein, when referring to substituents, the term “adjacent” means groups bonded to carbons linked together by single or multiple bonds. The following show exemplary adjacent R groups:

[0020]

[0021] The term “alkoxy” is intended to mean the group RO-, where R is an alkyl group.

[0022] The term “alkyl” is intended to mean a group derived from an aliphatic hydrocarbon and includes straight-chain, branched-chain, or cyclic groups. A group “derived from” a compound indicates a group formed by removing one or more H or D.

[0023] In some embodiments, the alkyl group has 1 - 20 carbon atoms.

[0024] The term “aromatic compound” is intended to mean an organic compound containing at least one unsaturated cyclic group having 4n + 2 delocalized π electrons.

[0025] The term “aryl” is intended to mean a group having one or more attachment points derived from an aromatic hydrocarbon. The term includes groups having a single ring and groups having multiple rings that may be linked or fused together by single bonds. A carbocyclic aryl has only carbon in the ring structure. A heteroaryl has at least one heteroatom in the ring structure.

[0026] The term “arylamine” or “arylamine group” is intended to mean a specific type of heteroaryl in which the heteroatom is an amino nitrogen (N) directly bonded to one or more aromatic rings or aryl groups.

[0027] The term “alkylaryl” is intended to mean an aryl group having one or more alkyl substituents.

[0028] The term “aryloxy” is intended to mean the group RO-, where R is an aryl group.

[0029] When referring to a layer, material, component, or structure, the term “charge transport” is intended to mean such a layer, material, component, or structure that facilitates the migration of such charges through the thickness of such layer, material, component, or structure with relatively high efficiency and little charge loss. A hole transport material facilitates positive charges; an electron transport material facilitates negative charges. Although a luminescent material may also have some charge transport properties, the term “charge transport layer, material, component, or structure” is not intended to include a layer, material, component, or structure whose primary function is luminescence.

[0030] When referring to a compound, the term "nuclear structure" is intended to mean a specific group of atoms bonded together by a specific partial structure.

[0031] The term "deuterated" is intended to mean that at least one hydrogen ("H") has been replaced by deuterium ("D"). The term "deuterated analogue" refers to an analogue of a compound or group having the same structure but in which one or more available hydrogens have been replaced by deuterium. In a deuterated compound or deuterated analogue, deuterium is present at a level of at least 100 times the natural abundance level. The term "% deuterated" or "% deuteration" is intended to mean the ratio of deuterium nuclei to the sum of protons and deuterium nuclei, expressed as a percentage.

[0032] The term "dipole moment" or "μ" is intended to mean a measure of the separation between positive and negative charges within a molecule or system. It is a measure of the resulting overall polarity and can be expressed in units of Debye (D).

[0033] The term "dopant" is intended to mean a material within a layer containing a host material that, compared to one or more electronic properties or one or more wavelengths of radiation emission, reception, or filtering of the layer in the absence of such material, changes one or more electronic properties or one or more target wavelengths of radiation emission, reception, or filtering of the layer.

[0034] The term "germyl" refers to the group R 3 Ge-, where R is the same or different each time it appears and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl.

[0035] The term "glass transition temperature" or "T g g" is intended to mean the temperature at which an amorphous material undergoes a reversible change from a relatively brittle glassy state to a viscous or rubbery state upon heating.

[0036] The prefix "hetero" indicates that one or more carbon atoms have been replaced by different atoms. In some embodiments, the different atoms are N, O, or S.

[0037] The term "host material" is intended to mean a material that is typically in the form of a layer into which a dopant can be added. The host material may or may not have one or more electronic properties or capabilities of emitting, receiving, or filtering radiation.

[0038] The terms "luminescent material", "emissive material", and "emitter" are intended to mean materials that emit light when activated by an applied voltage (such as in a light-emitting diode or a light-emitting electrochemical cell). The term "blue luminescent material" is intended to mean a material capable of emitting radiation having an emission maximum at wavelengths in the range of approximately 445 - 490 nm.

[0039] The term "layer" is used interchangeably with the term "film" and refers to a coating that covers a desired area. The term is not limited by size. The area can be as large as an entire device, or as small as a specific functional area such as an actual visual display, or as small as a single sub-pixel. Layers and films can be formed by any conventional deposition technique, including vapor deposition, liquid deposition (continuous and discontinuous techniques), and thermal transfer. Continuous deposition techniques include, but are not limited to, spin coating, gravure coating, curtain coating, dip coating, slot die coating, spray coating, and continuous nozzle coating or printing. Discontinuous deposition techniques include, but are not limited to, inkjet printing, gravure printing, and screen printing.

[0040] The term "N-heterocycle" or "N-heteroaryl" refers to a heteroaromatic compound or group having at least one nitrogen in an aromatic ring.

[0041] The term "N,O,S-heterocycle" or "N,O,S-heteroaryl" refers to a heteroaromatic compound or group having at least one heteroatom in an aromatic ring, where the heteroatom is N, O, or S. The N,O,S-heterocycle can have more than one type of heteroatom.

[0042] The term "organic electronic device" or sometimes just "electronic device" is intended to mean a device that includes one or more organic semiconductor layers or materials.

[0043] The term "photoactive" refers to a material or layer that emits light (such as in a light-emitting diode or a chemical cell) when activated by an applied voltage, or that responds to radiant energy and generates a signal (such as in a photodetector or a photovoltaic cell), with or without an applied bias voltage. A photoactive material or layer is sometimes referred to as an emissive layer. The photoactive layer is abbreviated as "EML" herein and can also be referred to as the "emitting layer".

[0044] The term "electron blocking" refers to an optional material or layer between the HTL and the EML that can serve to manipulate positive and / or negative charges in order to improve the performance characteristics of an organic electronic device.

[0045] The term "siloxane" refers to the group R 3 SiO(R 2 Si)-, where R is the same or different each time it appears and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl. In some embodiments, one or more carbons in R alkyl are replaced by Si.

[0046] The term "silyloxy" refers to the group R 3 SiO-, where R is the same or different each time it appears and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl.

[0047] The term "silyl" refers to the group R 3 Si-, where R is the same or different each time it appears and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl. In some embodiments, one or more carbons in the R alkyl are replaced by Si.

[0048] The term "spontaneous orientation polarization" (which may be abbreviated as "SOP") refers to a phenomenon that can occur when molecules exhibiting a non-zero dipole moment adopt a preferred relative orientation upon evaporation to form a film. Specific chemical functional groups present in certain film-forming molecules can cause the vapor-deposited film to exhibit a net polarization, which can be measured, for example, in mV / nm. This phenomenon is not observed when non-polar molecules are evaporated to form a film or when polar molecules are evaporated in a random orientation. The SOP value is defined as positive when the associated polarization is towards the substrate and negative when the associated polarization is away from the substrate.

[0049] All groups may be unsubstituted or substituted. Substituents are discussed below. In structures where the substituent bond passes through one or more rings as shown below,

[0050]

[0051] this means that the substituent R can be bonded at any available position on one or more rings.

[0052] In any of the following formulas or combinations of formulas, any subscript that appears more than once (such as a-h, k, p, q, r, s, a1, b1, and k1) can be the same or different each time it appears.

[0053] In this specification, unless otherwise expressly stated or indicated to the contrary by the context of use, in embodiments of the subject matter of the present invention that are stated or described as comprising, including, containing, having certain features or elements, consisting of certain features or elements, or being composed of certain features or elements, one or more features or elements other than those expressly stated or described may also be present in the embodiment. Alternative embodiments of the disclosed subject matter of the present invention are described as consisting essentially of certain features or elements, where embodiment features or elements that would materially alter the operating principle or distinguishing features of the embodiment are not present herein. Another alternative embodiment of the described subject matter of the present invention is described as consisting of certain features or elements, in which embodiment or in its non-substantive variations, only the specifically stated or described features or elements are present.

[0054] In addition, the articles "a" and "an" are used to describe the elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the invention. This description should be read to include one or at least one, and the singular forms also include the plural, unless it is obvious otherwise.

[0055] The group numbers corresponding to the columns within the Periodic Table of the Elements are used according to the "New Notation" convention as seen in the CRC Handbook of Chemistry and Physics, 81st Edition (2000 - 2001).

[0056] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the embodiments of the present invention, suitable methods and materials are described below. In addition, the materials, methods, and examples are illustrative only and are not intended to be limiting.

[0057] Regarding ranges not described herein, many details regarding specific materials, processing operations, and circuits are conventional and can be found in textbooks and other sources in the fields of organic light - emitting diode displays, photodetectors, photovoltaic cells, and semiconductor components.

[0058] In this specification, unless otherwise clearly specified or indicated to the contrary by the context of use, when embodiments of the subject matter of the present invention are stated or described as comprising, including, containing, having certain features or elements, consisting of certain features or elements, or being composed of certain features or elements, one or more features or elements other than those explicitly stated or described may also be present in the embodiment. Alternative embodiments of the disclosed subject matter of the present invention are described as consisting essentially of certain features or elements, where embodiment features or elements that would materially alter the operating principle or distinguishing features of the embodiment are not present herein. Another alternative embodiment of the described subject matter of the present invention is described as consisting of certain features or elements, in which embodiment or in its non - substantial variations, only the features or elements specifically stated or described are present.

[0059] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. Although similar or equivalent to those methods and materials described herein can be used in the practice or testing of the embodiments of this disclosure, suitable methods and materials are described below. In addition, the materials, methods, and examples are illustrative only and are not intended to be limiting.

[0060] 2. Polarized arylamine compounds and their mixtures

[0061] The present disclosure provides a composition comprising a mixture of a first compound and a second compound; wherein the first compound has a chemical structure different from that of the second compound; wherein the first compound and the second compound have a molecular weight between 300 and 1000; wherein the first compound and the second compound have a glass transition temperature (T g ) greater than 105 °C; wherein the first compound and the second compound each comprise one or more arylamine groups; wherein the first compound has a concentration C1 in the mixture; wherein the second compound has a concentration C2 in the mixture; wherein C1 is between 1 wt.% and 99 wt.%; and C2 is between 1 wt.% and 99 wt.%.

[0062] In some non-limiting embodiments of the composition comprising a mixture of a first compound and a second compound disclosed herein, the first compound and the second compound have a molecular weight between 100 and 3000, in some non-limiting embodiments between 200 and 2000, in some non-limiting embodiments between 300 and 1000, in some non-limiting embodiments between 400 and 900, in some non-limiting embodiments between 500 and 800, and in some non-limiting embodiments between 600 and 700.

[0063] Since the first compound and the second compound have different chemical structures, non-limiting embodiments of the composition disclosed herein will generally have a first compound and a second compound with different molecular weights. Those of ordinary skill in the art will recognize that embodiments in which the first compound and the second compound have the same molecular weight are possible in selected cases.

[0064] In some non - limiting embodiments of the compositions disclosed herein that are mixtures of a first compound and a second compound, the first compound and the second compound have a glass transition temperature (Tg) greater than 90 °C, in some non - limiting embodiments greater than 95 °C, in some non - limiting embodiments greater than 100 °C, in some non - limiting embodiments greater than 105 °C, in some non - limiting embodiments greater than 110 °C, in some non - limiting embodiments greater than 115 °C, in some non - limiting embodiments greater than 120 °C, in some non - limiting embodiments greater than 125 °C, in some non - limiting embodiments greater than 130 °C, in some non - limiting embodiments greater than 135 °C, in some non - limiting embodiments greater than 140 °C, in some non - limiting embodiments greater than 145 °C, in some non - limiting embodiments greater than 150 °C, in some non - limiting embodiments greater than 155 °C, in some non - limiting embodiments greater than 160 °C, in some non - limiting embodiments greater than 165 °C, in some non - limiting embodiments greater than 170 °C, in some non - limiting embodiments greater than 180 °C, in some non - limiting embodiments greater than 190 °C, and in some non - limiting embodiments greater than 200 °C.

[0065] Since the first compound and the second compound have different chemical structures, non - limiting embodiments of the compositions disclosed herein will generally have a glass transition temperature (T g ) of the first compound and the second compound that are different from each other. Those of ordinary skill in the art will recognize that embodiments in which the first compound and the second compound have the same glass transition temperature (T g ) are possible in selected cases.

[0066] In some non - limiting embodiments of the compositions disclosed herein that are mixtures of a first compound and a second compound, the first compound contains one arylamine group, in some non - limiting embodiments contains two arylamine groups, in some non - limiting embodiments contains three arylamine groups, in some non - limiting embodiments contains four arylamine groups, and in some non - limiting embodiments contains 5 or more arylamine groups.

[0067] In some non - limiting embodiments of the compositions disclosed herein that are mixtures of a first compound and a second compound, the second compound contains one arylamine group, in some non - limiting embodiments contains two arylamine groups, in some non - limiting embodiments contains three arylamine groups, in some non - limiting embodiments contains four arylamine groups, and in some non - limiting embodiments contains 5 or more arylamine groups.

[0068] In some non-limiting embodiments of the compositions disclosed herein that comprise a mixture of a first compound and a second compound, the first compound has a dipole moment μ1 and a concentration C1, where C1 is between 1 wt.% and 99 wt.%, in some non-limiting embodiments between 10 wt.% and 90 wt.%, in some non-limiting embodiments between 20 wt.% and 80 wt.%, in some non-limiting embodiments between 30 wt.% and 70 wt.%, and in some non-limiting embodiments between 40 wt.% and 60 wt.%.

[0069] In some non-limiting embodiments of the compositions disclosed herein that comprise a mixture of a first compound and a second compound, the second compound has a dipole moment μ2 and a concentration C2, where C2 is between 1 wt.% and 99 wt.%, in some non-limiting embodiments between 10 wt.% and 90 wt.%, in some non-limiting embodiments between 20 wt.% and 80 wt.%, in some non-limiting embodiments between 30 wt.% and 70 wt.%, and in some non-limiting embodiments between 40 wt.% and 60 wt.%.

[0070] In some non-limiting embodiments of the compositions disclosed herein that comprise a mixture of a first compound and a second compound, the first compound has a dipole moment μ1, where μ1 is greater than 0.1 D, in some non-limiting embodiments greater than 0.2 D, in some non-limiting embodiments greater than 0.3 D, in some non-limiting embodiments greater than 0.4 D, in some non-limiting embodiments greater than 0.5 D, in some non-limiting embodiments greater than 0.6 D, in some non-limiting embodiments greater than 0.7 D, and in some non-limiting embodiments greater than 0.8 D.

[0071] In some non-limiting embodiments of the compositions disclosed herein that comprise a mixture of a first compound and a second compound, the second compound has a dipole moment μ2, where μ2 is greater than 0.1 D, in some non-limiting embodiments greater than 0.2 D, in some non-limiting embodiments greater than 0.3 D, in some non-limiting embodiments greater than 0.4 D, in some non-limiting embodiments greater than 0.5 D, in some non-limiting embodiments greater than 0.6 D, in some non-limiting embodiments greater than 0.7 D, and in some non-limiting embodiments greater than 0.8 D.

[0072] In some non-limiting embodiments of the compositions disclosed herein that comprise a mixture of a first compound and a second compound, the first compound and / or the second compound has a chemical structure given by Formula 1:

[0073]

[0074] where

[0075] X represents -O-, -S-, -Si(R’)(R”), -N(R)-, -C(R')(R”), -Se- or (R')(R”)C-C(R'”)(R”");

[0076] R, R' and R” each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, -L 2 -N-(Ar 3 )(Ar 4 ) or -L 3 -N(Ar 5 )-L 4 -N-(Ar 6 )(Ar 7 );or R' and R” may be joined to each other to form one or more rings, and R' and R” may be the same or different;

[0077] Ar 1 -Ar 7 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, where if there are multiple Ar 1 -Ar 7 , then adjacent Ar 1 -Ar 7 may be the same or different; where

[0078] if Ar 1 -Ar 7 each independently represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, then adjacent Ar 1 -Ar 7 may be joined to each other via a single bond to form one or more rings;

[0079] L 1 -L 4 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0080] R 1 and R 2Each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, where if there are multiple Rs 1 and / or R 2 and, each occurrence may be the same or different, and where adjacent Rs 1 and / or R 2 groups or Rs 1 and / or R 2 groups on adjacent rings may be joined together to form a 5- or 6-membered alicyclic ring, a carbocyclic aromatic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0081] a and b each independently represent an integer between 0 and 4, provided that when the bonds to L 1 are attached to the ring bearing R 1 or R 2 respectively, the maximum value of a or b is 3; and

[0082] n represents 1 or 2.

[0083] In some non-limiting embodiments of Formula 1, one or more compounds have a molecular weight, T g and dipole moment as disclosed above.

[0084] In some non-limiting embodiments of Formula 1, X = -O-.

[0085] In some non-limiting embodiments of Formula 1, X = -S-.

[0086] In some non-limiting embodiments of Formula 1, X = -Si(R’)(R”).

[0087] In some non-limiting embodiments of Formula 1, X = -N(R)-.

[0088] In some non-limiting embodiments of Formula 1, X = C(R’)(R”).

[0089] In some non-limiting embodiments of Formula 1, X = -Se-.

[0090] In some non-limiting embodiments of Formula 1, R, R', and R” each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, -L 2 -N-(Ar 3 )(Ar 4 ) or -L 3 -N(Ar 5 )-L 4 -N-(Ar 6 )(Ar 7 ), where L 2 、L 3 and L 4 are linking groups, and these linking groups have the same embodiments as those disclosed herein for L 1 ; or R' and R” can be linked to each other to form one or more rings, and R' and R” can be the same or different.

[0091] In some embodiments of Formula 1, the compound is deuterated. In some non-limiting embodiments, the compound is at least 10% deuterated; in some non-limiting embodiments, it is at least 20% deuterated; in some non-limiting embodiments, it is at least 30% deuterated; in some non-limiting embodiments, it is at least 40% deuterated; in some non-limiting embodiments, it is at least 50% deuterated; in some non-limiting embodiments, it is at least 60% deuterated; in some non-limiting embodiments, it is at least 70% deuterated; in some non-limiting embodiments, it is at least 80% deuterated; in some non-limiting embodiments, it is at least 90% deuterated; in some non-limiting embodiments, it is 100% deuterated.

[0092] In some non-limiting embodiments of Formula 1, deuteration is present on one or more of Ar 1 、Ar 2 、R 1 and R 2 .

[0093] In some non-limiting embodiments of Formula 1, Ar 1 is selected from the group consisting of hydrocarbon aryls, heteroaryls, and their substituted derivatives, where the substituted derivatives have only substituents selected from the group consisting of D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl, and no other substituents.

[0094] In some non-limiting embodiments of Formula 1, Ar 1 is an unsubstituted hydrocarbon aryl.

[0095] In some non-limiting embodiments of Formula 1, Ar 1 is a hydrocarbon aryl having 6 to 30 ring carbons or a deuterated analogue thereof; in some embodiments, it is a hydrocarbon aryl having 6 to 18 ring carbons or a deuterated analogue thereof.

[0096] In some non-limiting embodiments of Formula 1, Ar 1 is a substituted hydrocarbon aryl, wherein the substituents are selected from the group consisting of: D, alkyl, silyl, germanium alkyl, hydrocarbon aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germanium alkyl, deuterated hydrocarbon aryl and deuterated heteroaryl. In some embodiments, the heteroaryl has heteroatoms selected from the group consisting of: O, S and Se.

[0097] In some non-limiting embodiments of Formula 1, Ar 1 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, anthracenyl, fluorenyl, phenanthryl, their deuterated analogues and their derivatives having one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, hydrocarbon aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germanium alkyl, deuterated hydrocarbon aryl and deuterated heteroaryl. In some non-limiting embodiments, the heteroaryl has heteroatoms selected from the group consisting of: O, S and Se.

[0098] In some non-limiting embodiments of Formula 1, Ar 1 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, anthracenyl, fluorenyl, phenanthryl and their derivatives having one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl and deuterated germanium alkyl.

[0099] In some non-limiting embodiments of Formula 1, Ar 1 is selected from the group consisting of: phenyl, biphenyl, naphthyl and their substituted derivatives.

[0100] In some non-limiting embodiments of Formula 1, Ar 1 is an unsubstituted heteroaryl.

[0101] In some non-limiting embodiments of Formula 1, Ar 1 is a heteroaryl having 3 to 30 ring carbons or a deuterated analogue thereof; in some non-limiting embodiments, it is a heteroaryl having 3 to 18 ring carbons or a deuterated analogue thereof.

[0102] In some non-limiting embodiments of Formula 1, Ar 1is a substituted heteroaryl, wherein the substituent is selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl.

[0103] In some non-limiting embodiments of Formula 1, Ar 1 is selected from the group consisting of: heteroaryl and deuterated heteroaryl, wherein the heteroaryl has at least one ring atom selected from the group consisting of: O and S.

[0104] In some non-limiting embodiments of Formula 1, Ar 1 is an O-heteroaryl having at least one ring atom that is O.

[0105] In some non-limiting embodiments, the O-heteroaryl is derived from a compound selected from the group consisting of: furan, benzofuran, isobenzofuran, dibenzofuran, and substituted derivatives thereof.

[0106] In some non-limiting embodiments of Formula 1, Ar 1 is present and is an S-heteroaryl having at least one ring atom that is S.

[0107] In some non-limiting embodiments, the S-heteroaryl is derived from a compound selected from the group consisting of: thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, and substituted derivatives thereof.

[0108] All embodiments disclosed herein for Ar 1 equally apply to Ar 2 .

[0109] In some non-limiting embodiments of Formula 1, Ar 1 = Ar 2 .

[0110] In some non-limiting embodiments of Formula 1, Ar 1 ≠ Ar 2 .

[0111] In some non-limiting embodiments of Formula 1, L 1 is a single bond.

[0112] In some non-limiting embodiments of Formula 1, L 1 is a substituted or unsubstituted (C6-C30) arylene group given by Formula a:

[0113]

[0114] wherein R 3The same or different at each occurrence and selected from the group consisting of: D, alkyl, aryloxy, heteroaryl, alkoxy, silyloxy, silyl, germanium, deuterated alkyl, deuterated aryloxy, deuterated heteroaryl, deuterated alkoxy, deuterated siloxane, deuterated silyl, deuterated germanium, and wherein adjacent R 3 groups may be joined together to form a fused ring. In some non-limiting embodiments, p is the same or different at each occurrence and is an integer from 0 to 4. In some non-limiting embodiments, p1 is the same or different at each occurrence and is an integer from 0 to 4. In some non-limiting embodiments, r is an integer from 0 to 5.

[0115] In some non-limiting embodiments of Formula 1, L 1 is a substituted or unsubstituted (3- to 30-membered) heteroarylene derived from a corresponding heteroaryl selected from: pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazobenzimidazole, triazole, benzotriazole, triazolopyridine, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, indole, indoloindole, substituted derivatives thereof, and deuterated analogs thereof.

[0116] In some non-limiting embodiments of Formula 1, R 1 and R 2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, wherein if there are multiple R 1 and / or R 2 , then each may be the same or different at each occurrence.

[0117] In some non-limiting embodiments of Formula 1, a = 0. In some non-limiting embodiments, a = 1. In some non-limiting embodiments, a = 2. In some non-limiting embodiments, a = 3. In some non-limiting embodiments, a = 4.

[0118] In some non-limiting embodiments of Formula 1, b = 0. In some non-limiting embodiments, b = 1. In some non-limiting embodiments, b = 2. In some non-limiting embodiments, b = 3. In some non-limiting embodiments, a = b.

[0119] In some non-limiting embodiments of Formula 1, n = 1. In some non-limiting embodiments, n = 2. In embodiments where n = 1, the bridging group containing Y is a 5-membered ring. In embodiments where n = 2, the bridging group containing Y' is a 6-membered ring. In some non-limiting embodiments where n = 2, the two Ys are given by C(R')(R"), where R' and R" are as defined herein. In some non-limiting embodiments where n = 2, one Y is given by C(R')(R"), where R' and R" are as defined herein, and the other Y is selected from the group consisting of: -O-, -S-, -Si-, -N(R)-, and -Se-, where R is as defined herein.

[0120] In some non-limiting embodiments of Formula 1, X is Si(CH 3 ) 2 , R 1 and R 2 are H, L 1 is phenylene, Ar 1 is phenyl, Ar 2 is terphenyl, a and b are 4, and n is 1.

[0121] In some non-limiting embodiments of Formula 1, X is -C(R')(R"), R' and R" are methyl, R 1 and R 2 are H, L 1 is phenylene, Ar 1 is phenyl, Ar 2 is 1-phenylterphenyl, a and b are 4, and n is 2. In some non-limiting embodiments of Formula 1, X is -C(R')(R"), R' and R" are methyl, R 1 and R 2 are H, L 1 is phenylene, Ar 1 is phenyl, Ar 2is 2-phenyltriphenyl, a and b are 4, and n is 2. Regarding the selection of a specific compound having Formula 1 for use in a specific OLED device, there are many considerations of potential importance. A significant dipole moment of an individual molecule is a necessary but not sufficient condition. The molecular shape used, specific short-range interactions, and processing conditions also appear to be important factors affecting the SOP; however, it is currently not possible to even predict the polarization direction by only simulating a single molecule. Therefore, the basic design principle of a polarized arylamine compound (such as those having Formula 1 as disclosed herein) is to include at least one electron-deficient or electron-rich functional group (such as a heteroatom-containing or alkyl-containing fused polycyclic organic substance) in the molecular structure. To select a molecular structure with a higher likelihood of showing a strong SOP in a preferred direction, those skilled in the art can use molecular dynamics simulations of a vacuum deposition process.

[0122] Examples of compounds having Formula 1 include, but are not limited to, the compounds shown below.

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] In some non-limiting embodiments of the compositions of the mixtures comprising a first compound and a second compound disclosed herein, the first compound and / or the second compound has a chemical structure given by Formula 2:

[0129]

[0130] wherein

[0131] Y is the same or different in each occurrence and represents -O-, -S-, -Si(R’)(R”)-, -N(R)-, C(R')(R")-, -Se- or (R')(R")C-C(R'")(R"");

[0132] R, R' and R” each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, -L 2 -N-(Ar 3 )(Ar 4 ) or -L 3 -N(Ar 5 )-L 4-N-(Ar 6 )(Ar 7 ); or R' and R'' may be joined to each other to form one or more rings, and R' and R'' may be the same or different;

[0133] Ar 3 -Ar 9 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, wherein if there are multiple Ar 3 -Ar 9 , then each of Ar 3 -Ar 9 may be the same or different; wherein

[0134] if Ar 3 -Ar 9 each independently represents substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl, then adjacent Ar 3 -Ar 9 may be joined to each other via a single bond to form one or more rings;

[0135] L 2 -L 5 represents a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0136] R 3 -R 5 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, wherein if there are multiple R3 -R 5 , each of which may be the same or different each time it appears; and adjacent Rs 3 and / or R 4 and / or R 5 groups or Rs on adjacent rings 3 and / or R 4 and / or R 5 groups may be joined together to form a 5- or 6-membered cycloaliphatic ring, a carbocyclic aromatic ring, a heteroaromatic ring or a substituted derivative thereof;

[0137] c and e each independently represent an integer between 0 and 3, provided that when the bonds to L 5 are respectively attached to the ring bearing R 3 or R 5 , the maximum value of c or e is 2; d represents an integer between 0 and 2, provided that when the bond to L 5 is attached to the ring bearing R 4 , the maximum value of d is 1; and

[0138] n represents 1 or 2.

[0139] In some non-limiting embodiments of Formula 2, one or more compounds have a molecular weight, T g and dipole moment as disclosed above.

[0140] In some non-limiting embodiments of Formula 2, Y = -O-.

[0141] In some non-limiting embodiments of Formula 2, Y = -S-.

[0142] In some non-limiting embodiments of Formula 2, Y = -Si(R’)(R”).

[0143] In some non-limiting embodiments of Formula 2, Y = -N(R)-.

[0144] In some non-limiting embodiments of Formula 2, Y = C(R’)(R”).

[0145] In some non-limiting embodiments of Formula 2, Y = -Se-.

[0146] In some non-limiting embodiments of Formula 2, R, R' and R” each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, -L 2 -N-(Ar 3 )(Ar 4 ) or -L 3 -N(Ar 5 )-L4 -N-(Ar 6 )(Ar 7 ), wherein L 2 , L 3 and L 4 are linking groups, and these linking groups have the same embodiments as those disclosed herein for L 5 ; or R' and R'' may be connected to each other to form one or more rings, and R' and R'' may be the same or different.

[0147] In some embodiments of Formula 2, the compound is deuterated. In some non-limiting embodiments, the compound is at least 10% deuterated; in some non-limiting embodiments, it is at least 20% tritiated; in some non-limiting embodiments, it is at least 30% tritiated; in some non-limiting embodiments, it is at least 40% tritiated; in some non-limiting embodiments, it is at least 50% tritiated; in some non-limiting embodiments, it is at least 60% tritiated; in some non-limiting embodiments, it is at least 70% tritiated; in some non-limiting embodiments, it is at least 80% tritiated; in some non-limiting embodiments, it is at least 90% tritiated; in some non-limiting embodiments, it is 100% tritiated.

[0148] In some non-limiting embodiments of Formula 2, deuteration is present on one or more of Ar 8 , Ar 9 and R 3 -R 5 .

[0149] In some non-limiting embodiments of Formula 2, Ar 8 is selected from the group consisting of hydrocarbon aryl, heteroaryl and their substituted derivatives, wherein the substituted derivatives have only substituents selected from the group consisting of D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl and deuterated germanium alkyl, and no other substituents.

[0150] In some non-limiting embodiments of Formula 2, Ar 8 is an unsubstituted hydrocarbon aryl.

[0151] In some non-limiting embodiments of Formula 2, Ar 8 is a hydrocarbon aryl having 6 - 30 ring carbons or its deuterated analogue; in some embodiments, it is a hydrocarbon aryl having 6 - 18 ring carbons or its deuterated analogue.

[0152] In some non-limiting embodiments of Formula 2, Ar 8is a substituted hydrocarbylaryl, wherein the substituent is selected from the group consisting of: D, alkyl, silyl, germanium alkyl, hydrocarbylaryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germanium alkyl, deuterated hydrocarbylaryl, and deuterated heteroaryl. In some embodiments, the heteroaryl has a heteroatom selected from the group consisting of: O, S, and Se.

[0153] In some non-limiting embodiments of Formula 2, Ar 8 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, anthracenyl, fluorenyl, phenanthryl, their deuterated analogs, and their derivatives having one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, hydrocarbylaryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germanium alkyl, deuterated hydrocarbylaryl, and deuterated heteroaryl. In some non-limiting embodiments, the heteroaryl has a heteroatom selected from the group consisting of: O, S, and Se.

[0154] In some non-limiting embodiments of Formula 2, Ar 8 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, anthracenyl, fluorenyl, phenanthryl, and their derivatives having one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl.

[0155] In some non-limiting embodiments of Formula 2, Ar 8 is selected from the group consisting of: phenyl, biphenyl, naphthyl, and their substituted derivatives.

[0156] In some non-limiting embodiments of Formula 2, Ar 8 is an unsubstituted heteroaryl.

[0157] In some non-limiting embodiments of Formula 2, Ar 8 is a heteroaryl having 3-30 ring carbons or its deuterated analog; in some non-limiting embodiments, it is a heteroaryl having 3-18 ring carbons or its deuterated analog.

[0158] In some non-limiting embodiments of Formula 2, Ar 8 is a substituted heteroaryl, wherein the substituent is selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl.

[0159] In some non-limiting embodiments of Formula 2, Ar 8 is selected from the group consisting of: heteroaryl and deuterated heteroaryl, wherein the heteroaryl has at least one ring atom selected from the group consisting of: O and S.

[0160] In some non-limiting embodiments of Formula 2, Ar 8 is an O-heteroaryl having at least one ring atom that is O.

[0161] In some non-limiting embodiments, the O-heteroaryl is derived from a compound selected from the group consisting of furan, benzofuran, isobenzofuran, dibenzofuran, and substituted derivatives thereof.

[0162] In some non-limiting embodiments of Formula 2, Ar 8 is present and is an S-heteroaryl having at least one ring atom that is S.

[0163] In some non-limiting embodiments, the S-heteroaryl is derived from a compound selected from the group consisting of thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, and substituted derivatives thereof.

[0164] All embodiments disclosed herein for Ar 8 equally apply to Ar 9 .

[0165] In some non-limiting embodiments of Formula 2, Ar 8 = Ar 9 .

[0166] In some non-limiting embodiments of Formula 2, Ar 8 ≠ Ar 9 .

[0167] In some non-limiting embodiments of Formula 2, L 5 is a single bond.

[0168] In some non-limiting embodiments of Formula 2, L 5 is a substituted or unsubstituted (C6-C30) arylene group given by Formula a:

[0169]

[0170] wherein R 3 is the same or different each time it appears and is selected from the group consisting of D, alkyl, aryloxy, heteroaryl, alkoxy, silyloxy, silyl, germanium, deuterated alkyl, deuterated aryloxy, deuterated heteroaryl, deuterated alkoxy, deuterated siloxane, deuterated silyl, deuterated germanium, and wherein adjacent R 3 groups may be joined together to form a fused ring. In some non-limiting embodiments, p is the same or different each time it appears and is an integer from 0-4. In some non-limiting embodiments, p1 is the same or different each time it appears and is an integer from 0-4. In some non-limiting embodiments, r is an integer from 0-5.

[0171] In some non-limiting embodiments of Formula 2, L 5 is a substituted or unsubstituted (3- to 30-membered) heteroarylene derived from a corresponding heteroaryl selected from pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazobenzimidazole, triazole, benzotriazole, triazolopyridine, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, indole, indoloindole, substituted derivatives thereof, and deuterated analogs thereof.

[0172] In some non-limiting embodiments of Formula 2, R 3 -R 5 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, where if there are multiple R 3 -R 5 , each may be the same or different at each occurrence.

[0173] In some non-limiting embodiments of Formula 2, c = 0. In some non-limiting embodiments, c = 1. In some non-limiting embodiments, c = 2. In some non-limiting embodiments, c = 3.

[0174] In some non-limiting embodiments of Formula 2, d = 0. In some non-limiting embodiments, d = 1. In some non-limiting embodiments, d = 2.

[0175] In some non-limiting embodiments of Formula 2, e = 0. In some non-limiting embodiments, e = 1. In some non-limiting embodiments, e = 2. In some non-limiting embodiments, e = 3.

[0176] In some non-limiting embodiments of Formula 2, n = 1. In some non-limiting embodiments, n = 2. In embodiments where n = 1, the bridging group containing Y is a 5-membered ring. In embodiments where n = 2, the bridging group containing Y' is a 6-membered ring. In some non-limiting embodiments where n = 2, the two Ys are given by C(R')(R"), where R' and R" are as defined herein. In some non-limiting embodiments where n = 2, one Y is given by C(R')(R"), where R' and R" are as defined herein, and the other Y is selected from the group consisting of -O-, -S-, -Si-, -N(R)-, and -Se-, where R is as defined herein.

[0177] In some non-limiting embodiments of Formula 2, Y is C(R')(R"), R' and R" are methyl, R 3 -R 5 is H, L 5 is phenylene, Ar 8 is phenyl, Ar 9 is terphenyl, n is 1, c and e are 3, and d is 1.

[0178] In some non-limiting embodiments of Formula 2, Y is C(R')(R"), R' and R" are methyl, R 3 -R 5 is H, L 5 is phenylene, Ar 8 is phenyl, Ar 9 is 2-benzophenanthrene, n is 1, c and e are 3, and d is 1.

[0179] The considerations for selecting a particular compound of Formula 2 for use in an OLED device are the same as those discussed above in the context of one or more compounds of Formula 1.

[0180] Examples of compounds having Formula 2 include, but are not limited to, the compounds shown below.

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] In some non-limiting embodiments of the compositions of the mixtures comprising a first compound and a second compound disclosed herein, the first compound and / or the second compound has a chemical structure given by Formula 3:

[0187]

[0188] wherein

[0189] Ar 10 -Ar 11 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, provided that if there are multiple Ar 3 -Ar 9 's, then each of the Ar 10 -Ar 11 's may be the same or different; wherein

[0190] if each of the Ar 10 -Ar 11 's independently represents substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl, then adjacent Ar 3 -Ar 9 's may be connected to each other via a single bond to form one or more rings;

[0191] L 6 represents a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene, and R 6 , R 7 and R 8 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, provided that if there are multiple R 6 , R 7 and / or R 8, each of which may be the same or different upon each occurrence; and wherein adjacent R 6 and / or R 7 and / or R 8 groups or R 6 and / or R 7 and / or R 8 groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, a carbocyclic aromatic ring, a heteroaromatic ring or a substituted derivative thereof;

[0192] f represents an integer between 0 and 8, g represents an integer between 0 and 2, and h represents an integer between 0 and 4, provided that when the bonds to L 6 are attached to the ring bearing R 7 or R 8 , the maximum value of g is 1 and the maximum value of h is 3.

[0193] In some non-limiting embodiments of Formula 3, one or more of the compounds have a molecular weight, T g and dipole moment as disclosed above.

[0194] In some embodiments of Formula 3, the compound is deuterated. In some non-limiting embodiments, the compound is at least 10% deuterated; in some non-limiting embodiments, it is at least 20% tritiated; in some non-limiting embodiments, it is at least 30% tritiated; in some non-limiting embodiments, it is at least 40% tritiated; in some non-limiting embodiments, it is at least 50% tritiated; in some non-limiting embodiments, it is at least 60% tritiated; in some non-limiting embodiments, it is at least 70% tritiated; in some non-limiting embodiments, it is at least 80% tritiated; in some non-limiting embodiments, it is at least 90% tritiated; in some non-limiting embodiments, it is 100% tritiated.

[0195] In some non-limiting embodiments of Formula 3, deuteration is present on one or more of Ar 10 , Ar 11 and R 6 -R 8 .

[0196] In some non-limiting embodiments of Formula 3, Ar 10 is selected from the group consisting of hydrocarbon aryl, heteroaryl and substituted derivatives thereof, wherein the substituted derivatives have only substituents selected from the group consisting of D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl and deuterated germanium alkyl, and no other substituents.

[0197] In some non-limiting embodiments of Formula 3, Ar 10 is an unsubstituted hydrocarbon aryl.

[0198] In some non - limiting embodiments of Formula 3, Ar 10 is a hydrocarbon aryl having 6 - 30 ring carbons or a deuterated analogue thereof; in some embodiments, it is a hydrocarbon aryl having 6 - 18 ring carbons or a deuterated analogue thereof.

[0199] In some non - limiting embodiments of Formula 3, Ar 10 is a substituted hydrocarbon aryl, wherein the substituents are selected from the group consisting of: D, alkyl, silyl, germanium alkyl, hydrocarbon aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germanium alkyl, deuterated hydrocarbon aryl, and deuterated heteroaryl. In some embodiments, the heteroaryl has heteroatoms selected from the group consisting of: O, S, and Se.

[0200] In some non - limiting embodiments of Formula 3, Ar 10 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1 - naphthyl, 2 - naphthyl, anthracenyl, fluorenyl, phenanthryl, their deuterated analogues, and their derivatives having one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, hydrocarbon aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germanium alkyl, deuterated hydrocarbon aryl, and deuterated heteroaryl. In some non - limiting embodiments, the heteroaryl has heteroatoms selected from the group consisting of: O, S, and Se.

[0201] In some non - limiting embodiments of Formula 3, Ar 10 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1 - naphthyl, 2 - naphthyl, anthracenyl, fluorenyl, phenanthryl, and their derivatives having one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl.

[0202] In some non - limiting embodiments of Formula 3, Ar 10 is selected from the group consisting of: phenyl, biphenyl, naphthyl, and their substituted derivatives.

[0203] In some non - limiting embodiments of Formula 3, Ar 10 is an unsubstituted heteroaryl.

[0204] In some non - limiting embodiments of Formula 3, Ar 10 is a heteroaryl having 3 - 30 ring carbons or a deuterated analogue thereof; in some non - limiting embodiments, it is a heteroaryl having 3 - 18 ring carbons or a deuterated analogue thereof.

[0205] In some non - limiting embodiments of Formula 3, Ar 10is a substituted heteroaryl, wherein the substituent is selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl.

[0206] In some non-limiting embodiments of Formula 3, Ar 10 is selected from the group consisting of: heteroaryl and deuterated heteroaryl, wherein the heteroaryl has at least one ring atom selected from the group consisting of: O and S.

[0207] In some non-limiting embodiments of Formula 3, Ar 10 is an O-heteroaryl having at least one ring atom that is O.

[0208] In some non-limiting embodiments, the O-heteroaryl is derived from a compound selected from the group consisting of: furan, benzofuran, isobenzofuran, dibenzofuran, and their substituted derivatives.

[0209] In some non-limiting embodiments of Formula 3, Ar 10 is present and is an S-heteroaryl having at least one ring atom that is S.

[0210] In some non-limiting embodiments, the S-heteroaryl is derived from a compound selected from the group consisting of: thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, and their substituted derivatives.

[0211] All embodiments disclosed herein for Ar 10 equally apply to Ar 11 .

[0212] In some non-limiting embodiments of Formula 3, Ar 10 = Ar 11 .

[0213] In some non-limiting embodiments of Formula 3, Ar 10 ≠ Ar 11 .

[0214] In some non-limiting embodiments of Formula 3, L 6 is a single bond.

[0215] In some non-limiting embodiments of Formula 3, L 6 is a substituted or unsubstituted (C6-C30) arylene group given by Formula a:

[0216]

[0217] wherein R 3identical or different at each occurrence and selected from the group consisting of: D, alkyl, aryloxy, heteroaryl, alkoxy, silyloxy, silyl, germanium, deuterated alkyl, deuterated aryloxy, deuterated heteroaryl, deuterated alkoxy, deuterated siloxane, deuterated silyl, deuterated germanium, and wherein adjacent R 3 groups may be joined together to form a fused ring. In some non-limiting embodiments, p is identical or different at each occurrence and is an integer from 0 to 4. In some non-limiting embodiments, p1 is identical or different at each occurrence and is an integer from 0 to 4. In some non-limiting embodiments, r is an integer from 0 to 5.

[0218] In some non-limiting embodiments of Formula 3, L 6 is a substituted or unsubstituted (3- to 30-membered) heteroarylene derived from a corresponding heteroaryl selected from: pyrrole, pyridine, pyrimidine, carbazole, imidazole, benzimidazole, imidazobenzimidazole, triazole, benzotriazole, triazolopyridine, indolocarbazole, phenanthroline, quinoline, isoquinoline, quinoxaline, indole, indolindole, substituted derivatives thereof, and deuterated analogs thereof.

[0219] In some non-limiting embodiments of Formula 3, R 6 -R 8 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, wherein if there are multiple R 6 -R 8 then each may be the same or different at each occurrence.

[0220] In some non-limiting embodiments of Formula 3, f = 0. In some non-limiting embodiments, f = 1. In some non-limiting embodiments, f = 2. In some non-limiting embodiments, f = 3. In some non-limiting embodiments, f = 4. In some non-limiting embodiments, f = 5. In some non-limiting embodiments, f = 6. In some non-limiting embodiments, f = 7. In some non-limiting embodiments, f = 8.

[0221] In some non-limiting embodiments of Formula 3, g = 0. In some non-limiting embodiments, g = 1. In some non-limiting embodiments, g = 2.

[0222] In some non-limiting embodiments of Formula 3, h = 0. In some non-limiting embodiments, h = 1. In some non-limiting embodiments, h = 2. In some non-limiting embodiments, h = 3. In some non-limiting embodiments, h = 4.

[0223] The considerations for selecting a particular compound of Formula 3 for use in an OLED device are the same as those discussed above in the context of one or more compounds of Formula 1 and / or Formula 2.

[0224] Examples of compounds having Formula 3 include, but are not limited to, the compounds shown below.

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231] Although the discovery of SOP was relatively early, its mechanism is still not fully understood. A significant dipole moment of a single molecule is a necessary but not sufficient condition. Molecular shape, specific short-range interactions, and processing conditions seem to be important factors affecting SOP; however, it is currently impossible to even predict the polarization direction by only simulating a single molecule.

[0232] The basic design principle of a polarized arylamine compound is to include at least one electron-deficient or electron-rich functional group (such as a fused polycyclic organic substance containing a heteroatom or an alkyl group) in the molecular structure. In order to select a molecular structure with a higher possibility of showing a strong SOP in a preferred direction, molecular dynamics simulation of the vacuum deposition process can be used.

[0233] In some non-limiting embodiments of the compositions disclosed herein that include a mixture of a first compound and a second compound, both the first compound and the second compound have a chemical structure given by Formula 1, in some non-limiting embodiments both have a chemical structure given by Formula 2, in some non-limiting embodiments both have a chemical structure given by Formula 3, and in some non-limiting embodiments the first compound and the second compound are a combination of Formula 1 and Formula 2, Formula 1 and Formula 3, or Formula 2 and Formula 3.

[0234] 3. Thin films

[0235] The present disclosure further provides a thin film that includes a mixture of a first compound and a second compound; wherein the first compound has a chemical structure different from that of the second compound; wherein the first compound and the second compound have a molecular weight between 300 and 1000; wherein the first compound and the second compound have a glass transition temperature greater than 105 °C; wherein the first compound and the second compound each include one or more arylamine groups; wherein the thin film formed from the first compound has a spontaneous orientation polarization SOP-1; wherein the thin film formed from the second compound has a spontaneous orientation polarization SOP-2; and the absolute value of the difference between SOP-1 and SOP-2 is greater than or equal to 10 mV / nm.

[0236] Specific embodiments of the first compound, the second compound, and the mixture of the compounds are the same as those disclosed above.

[0237] In some non-limiting embodiments, the thin film formed from the first compound has a spontaneous orientation polarization SOP-1 between -50 mV / nm and +150 mV / nm, in some non-limiting embodiments between -40 mV / nm and +140 mV / nm, in some non-limiting embodiments between -30 mV / nm and +130 mV / nm, in some non-limiting embodiments between -20 mV / nm and +120 mV / nm, in some non-limiting embodiments between -10 mV / nm and +110 mV / nm, in some non-limiting embodiments between 0 mV / nm and 100 mV / nm, in some non-limiting embodiments between 10 mV / nm and 80 mV / nm, and in some non-limiting embodiments between 20 mV / nm and 60 mV / nm.

[0238] In some non-limiting embodiments, the thin film formed from the second compound has a spontaneous orientation polarization SOP-2 between -50 mV / nm and +150 mV / nm, between -40 mV / nm and +140 mV / nm in some non-limiting embodiments, between -30 mV / nm and +130 mV / nm in some non-limiting embodiments, between -20 mV / nm and +120 mV / nm in some non-limiting embodiments, between -10 mV / nm and +110 mV / nm in some non-limiting embodiments, between 0 mV / nm and 100 mV / nm in some non-limiting embodiments, between 10 mV / nm and 80 mV / nm in some non-limiting embodiments, and between 20 mV / nm and 60 mV / nm in some non-limiting embodiments.

[0239] In some non-limiting embodiments, the absolute value of the difference between SOP-1 and SOP-2 is greater than or equal to 2 mV / nm, greater than or equal to 4 mV / nm in some non-limiting embodiments, greater than or equal to 6 mV / nm in some non-limiting embodiments, greater than or equal to 8 mV / nm in some non-limiting embodiments, greater than or equal to 10 mV / nm in some non-limiting embodiments, greater than or equal to 12 mV / nm in some non-limiting embodiments, greater than or equal to 14 mV / nm in some non-limiting embodiments, greater than or equal to 16 mV / nm in some non-limiting embodiments, greater than or equal to 18 mV / nm in some non-limiting embodiments, greater than or equal to 20 mV / nm in some non-limiting embodiments, greater than or equal to 25 mV / nm in some non-limiting embodiments, greater than or equal to 30 mV / nm in some non-limiting embodiments, greater than or equal to 35 mV / nm in some non-limiting embodiments, and greater than or equal to 40 mV / nm in some non-limiting embodiments.

[0240] In some non-limiting embodiments of the thin films disclosed herein, the thin film has a thickness between 1 nm and 200 nm, between 2 nm and 100 nm in some non-limiting embodiments, between 4 nm and 50 nm in some non-limiting embodiments, and between 5 nm and 20 nm in some non-limiting embodiments.

[0241] The method for generating a thin film is not limited and is generally known to those skilled in the art. In some non-limiting embodiments, dry film-forming methods such as vacuum deposition, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot die coating, spin coating, dip coating, flow coating methods, etc. can be used. When using a wet film-forming method, a thin film is formed by dissolving or dispersing the mixture in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent is not particularly limited as long as the mixture is soluble or dispersible in the solvent without causing any problems when forming the target thin film.

[0242] 4. Organic electronic devices

[0243] The present disclosure further provides an organic electronic device including two or more layers, wherein a first layer of the two or more layers is an emission layer comprising one or more organic host compounds and one or more dopant compounds; wherein a second layer of the two or more layers is an electron blocking layer comprising a mixture of a first compound and a second compound; wherein the first compound has a different chemical structure from the second compound; wherein the first compound and the second compound each comprise one or more arylamine groups; wherein a thin film formed of the first compound has a spontaneous orientation polarization SOP-1; wherein a thin film formed of the second compound has a spontaneous orientation polarization SOP-2; wherein the absolute value of the difference between SOP-1 and SOP-2 is greater than or equal to 10 mV / nm; such that the emission layer has a spontaneous orientation polarization SOP-EML and the electron blocking layer has a spontaneous orientation polarization SOP-EBL; and the absolute value of the difference between SOP-EML and SOP-EBL is less than or equal to 25 mV / nm.

[0244] Organic electronic devices that can benefit from having one or more layers comprising the compounds and layers described herein include, but are not limited to, (1) devices that convert electrical energy into radiation (e.g., light-emitting diodes, light-emitting diode displays, diode lasers, or lighting panels), (2) devices that detect signals using electronic processes (e.g., photodetectors, photoconductive cells, photoresistors, optical switches, phototransistors, phototubes, infrared (“IR”) detectors or biosensors), (3) devices that convert radiation into electrical energy (e.g., photovoltaic devices or solar cells), (4) devices that convert light of one wavelength into light of a longer wavelength (e.g., down-converting phosphor devices); (5) devices including one or more electronic components that include one or more organic semiconductor layers (e.g., transistors or diodes); or any combination of the devices in items (1) to (5).

[0245] In some non-limiting embodiments, an organic electronic device includes two or more layers, wherein a first layer of the two or more layers is an emissive layer comprising one or more organic host compounds and one or more dopant compounds, and wherein a second layer of the two or more layers is an electron blocking layer comprising a mixture of a first compound and a second compound as disclosed herein.

[0246] An illustration of an organic electronic device structure is shown in Figure 1 . Device 100 has a first electrical contact layer (anode layer) 110 and a second electrical contact layer (cathode layer) 170 and a photoactive layer (“EML”) 150 therebetween. Adjacent to the anode is a hole injection layer (“HIL”) 120. Adjacent to the hole injection layer is a hole transport layer (“HTL”) 130 comprising a hole transport material. Adjacent to the hole transport layer is an electron blocking layer (“EBL”) 140 comprising a mixture of a first compound and a second compound as disclosed herein. Adjacent to the cathode may be an electron transport layer (“ETL”) 160 comprising an electron transport material. Optionally, the device may use one or more additional hole injection layers or hole transport layers (not shown) adjacent to anode 110 and / or one or more additional electron injection layers (“EIL”) or electron transport layers (not shown) adjacent to cathode 170. As a further option, the device may have a quenching resistant layer (not shown) between photoactive layer 150 and electron transport layer 160.

[0247] Layers 120 to 160 and any additional layers therebetween are individually and collectively referred to as active layers. In some non-limiting embodiments, the photoactive layer is pixelated. In such a device, layer 150 will be divided into pixel or sub-pixel units that repeat over the layer. Each of the pixel or sub-pixel units represents a different color. In some embodiments, the sub-pixel units are red, green, and blue. In some non-limiting embodiments, three sub-pixel units are used. In some non-limiting embodiments, more than three sub-pixel units may be used.

[0248] In some non-limiting embodiments, as Figure 2 shown, the electron blocking layer is common in red, green, and blue pixels. In some non-limiting embodiments, as Figure 3 shown, each sub-pixel has a unique electron blocking layer.

[0249] In some non-limiting embodiments, the different layers have the following thickness ranges: anode 110, 50 - 500 nm, and in some non-limiting embodiments, 100 - 200 nm; hole injection layer 120, 5 - 200 nm, and in some non-limiting embodiments, 20 - 100 nm; hole transport layer 130, 5 - 200 nm, and in some non-limiting embodiments, 20 - 100 nm; electron blocking layer 140, 5 - 50 nm, and in some non-limiting embodiments, 5 - 25 nm; photoactive layer 150, 1 - 200 nm, and in some non-limiting embodiments, 10 - 100 nm; electron transport layer 160, 5 - 200 nm, and in some non-limiting embodiments, 10 - 100 nm; cathode 170, 10 - 500 nm, and in some non-limiting embodiments, 15 - 100 nm. The position of the electron-hole recombination region in the device, and thus the emission spectrum of the device, can be affected by the relative thickness of each layer. The desired ratio of layer thicknesses will depend on the exact nature of the materials used.

[0250] In some non-limiting embodiments, a mixture of a first compound and a second compound as disclosed herein can be used in the electron blocking layer of an organic electronic device. Non-limiting examples of the first compound and the second compound are the same as those disclosed elsewhere herein.

[0251] a. Photoactive layer

[0252] In some non-limiting embodiments, the photoactive layer comprises one or more organic host compounds and one or more dopant compounds. In some non-limiting embodiments, the photoactive layer consists only of host compounds and dopant compounds. In some non-limiting embodiments, small amounts of other materials are present provided that they do not significantly alter the function of the layer.

[0253] Dopants are well-known and widely disclosed in the patent literature and technical journals. Exemplary dopants include, but are not limited to, anthracene, benz[a]anthracene, benz[de]anthracene, pyrene, benzophenanthrene, benzofluorene, other polycyclic aromatics, and analogs having one or more heteroatoms. Exemplary dopants also include, but are not limited to, benzofuran, dibenzofuran, carbazole, benzocarbazole, carbazolocarbazole, and azaboranes. In some embodiments, the dopant has one or more diarylamino substituents. Doped materials have been disclosed, for example, in US 7,816,017, US 8,465,848, US 9,112,157, US2006 / 0127698, US2010 / 0032658, US2018 / 0069182, US2019 / 0058124, CA 3107010, EP 3109253, WO2019003615, and WO 2019035268.

[0254] In addition, in some non-limiting embodiments, the dopant is selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). In some non-limiting embodiments, the dopant is selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt).

[0255] Host materials are also well-known and widely disclosed in patent literature and technical journals. Exemplary host materials include, but are not limited to, anthracene, pyrene, phenanthrene, benzophenanthrene, phenanthroline, naphthalene, triazine, quinoline, isoquinoline, quinoxaline, phenylpyridine, benzodifuran, metal quinolinate complexes, indolocarbazole, substituted derivatives thereof, and combinations thereof. Many of these host materials contain one or more heteroatoms - either in the backbone of the host compound molecular structure or as a result of incorporating heteroatom-containing substituents. In such cases, the host material exhibits a net dipole moment.

[0256] A non-limiting collection of such host materials includes:

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271] The weight ratio of the total dopant to the total host material ranges from 1:99 to 70:30; in some embodiments, from 5:95 to 70:30; in some embodiments, from 10:90 to 20:80.

[0272] Given these compositions and the use of one or more host materials that exhibit a net dipole moment, a photoactive layer comprising these hosts and one or more dopants can have a non-zero spontaneous orientation polarization (SOP) when cast as a thin film for use in the devices disclosed herein. In these cases, the value of the spontaneous orientation polarization is given by SOP-EML.

[0273] In some non-limiting embodiments of the organic electronic devices disclosed herein, the magnitude of SOP-EML is between 1 and 10 mV / nm, in some non-limiting embodiments between 10 and 20 mV / nm, in some non-limiting embodiments between 20 and 30 mV / nm, in some non-limiting embodiments between 30 and 40 mV / nm, in some non-limiting embodiments between 40 and 50 mV / nm, in some non-limiting embodiments between 50 and 60 mV / nm, in some non-limiting embodiments between 60 and 70 mV / nm, in some non-limiting embodiments between 70 and 80 mV / nm, in some non-limiting embodiments between 80 and 90 mV / nm, and in some non-limiting embodiments between 90 and 100 mV / nm.

[0274] While it may be true that using such an EML with a non-zero SOP can benefit from a reduced device operating voltage, it may also lead to increased exciton quenching and reduced device efficiency. Generally, it has been found that in devices such as those disclosed herein, the electron / hole recombination region is relatively narrow and close to the interface between the emissive layer and the electron blocking layer, as compared to those disclosed by Bangsund et al. (Science Advances, Vol. 6(32), pp. 1-10 (2020)). The deleterious effects due to the presence of SOP in the EML can be mitigated by reducing the positive charge closer to the interface between the EBL and the EML. This can be achieved via the judicious use of the electron blocking layer compositions disclosed herein, which have a spontaneous orientation polarization (SOP-EBL) that is tailored to have a value close to the corresponding value of SOP-EML. As demonstrated in the examples herein, the device operating voltage can be maintained while improving the overall efficiency.

[0275] b. Electron blocking layer

[0276] The electron blocking layer is typically a thin film comprising a mixture of a first compound and a second compound; wherein the first compound has a different chemical structure from the second compound; wherein the first compound and the second compound have a molecular weight between 300 and 1000; wherein the first compound and the second compound have a glass transition temperature greater than 105 °C; wherein the first compound and the second compound each comprise one or more arylamine groups; wherein the thin film formed from the first compound has a spontaneous orientation polarization SOP-1; wherein the thin film formed from the second compound has a spontaneous orientation polarization SOP-2; and the absolute value of the difference between SOP-1 and SOP-2 is greater than or equal to 10 mV / nm. Non-limiting examples of these compounds and related properties have been disclosed above and are also applicable to mixtures of the first and second compounds for use as electron blocking layers in organic electronic devices.

[0277] In some non-limiting embodiments of the organic electronic devices disclosed herein, the magnitude of SOP-EBL is between 1 and 10 mV / nm, in some non-limiting embodiments between 10 and 20 mV / nm, in some non-limiting embodiments between 20 and 30 mV / nm, in some non-limiting embodiments between 30 and 40 mV / nm, in some non-limiting embodiments between 40 and 50 mV / nm, in some non-limiting embodiments between 50 and 60 mV / nm, in some non-limiting embodiments between 60 and 70 mV / nm, in some non-limiting embodiments between 70 and 80 mV / nm, in some non-limiting embodiments between 80 and 90 mV / nm, and in some non-limiting embodiments between 90 and 100 mV / nm.

[0278] It has been found that overall device efficiency is improved when using an electron blocking layer having an SOP-EBL value close to the SOP-EML of the device. In some non-limiting embodiments, the absolute value of the difference between SOP-EML and SOP-EBL is less than or equal to 25 mV / nm, in some non-limiting embodiments less than 20 mV / nm, in some non-limiting embodiments less than 15 mV / nm, in some non-limiting embodiments less than 10 mV / nm, in some non-limiting embodiments less than 5 mV / nm, in some non-limiting embodiments less than 2.5 mV / nm, and in some non-limiting embodiments less than 1 mV / nm.

[0279] The concept of driving device efficiency improvement using one or more electron blocking layers with spontaneous orientation polarization values close to the corresponding values of the device's photoactive layer can be extended beyond using an electron blocking layer that includes a mixture of a first compound and a second compound as disclosed herein. As long as the absolute value of the difference between SOP-EML and SOP-EBL is less than or equal to 25 mV / nm, less than 20 mV / nm in some non-limiting embodiments, less than 15 mV / nm in some non-limiting embodiments, less than 10 mV / nm in some non-limiting embodiments, less than 5 mV / nm in some non-limiting embodiments, less than 2.5 mV / nm in some non-limiting embodiments, and less than 1 mV / nm in some non-limiting embodiments, an efficiency improvement can be expected. In some non-limiting embodiments, the electron blocking layer can include a mixture of a first compound, a second compound, and a third compound. In some non-limiting embodiments, four or more compounds can be used. Additionally, a single compound can be used in an electron blocking layer with an appropriate SOP-EBL. This final approach may have practical limitations as it may be difficult to prepare a single compound that exhibits the SOP necessary for a particular EML composition.

[0280] Accordingly, the present disclosure further provides an organic electronic device that includes an anode; a hole transport layer; an electron blocking layer; a light-emitting layer; an electron transport layer; and a cathode; wherein the light-emitting layer includes a host and a dopant; wherein the light-emitting layer has a spontaneous orientation polarization SOP-EML; wherein the electron blocking layer has a spontaneous orientation polarization SOP-EBL; such that the absolute value of the difference between SOP-EML and SOP-EBL is less than or equal to 25 mV / nm.

[0281] c. Other device layers

[0282] The other layers in the organic electronic device can be made of any materials known to be useful in such layers.

[0283] The anode 110 is an electrode that is particularly effective for injecting positive charge carriers. It can be made of materials such as those containing metals, mixed metals, alloys, metal oxides or mixed metal oxides, or it can be a conductive polymer and mixtures thereof. Suitable metals include Group 11 metals, metals in Groups 4, 5 and 6, and transition metals in Groups 8 - 10. If the anode is to be light-transmissive, mixed metal oxides of Group 12, 13 and 14 metals, such as indium tin oxide, are generally used. The anode can also be made of organic materials such as polyaniline, as described in "Flexible light-emitting diodes made from soluble conducting polymer", Nature, Volume 357, pages 477 - 479 (June 11, 1992). At least one of the anode and the cathode should be at least partially transparent to allow the generated light to be observed.

[0284] The hole injection layer 120 includes hole injection materials and can have one or more functions in an organic electronic device, including but not limited to planarization of the underlying layer, charge transport and / or charge injection characteristics, scavenging of impurities (such as oxygen or metal ions), and other aspects that facilitate or improve the performance of the organic electronic device. The hole injection layer can be formed from polymer materials such as polyaniline (PANI) or poly(ethylenedioxythiophene) (PEDOT), which are typically doped with a protonic acid. The protonic acid can be, for example, poly(styrene - sulfonic acid), poly(2 - acrylamido - 2 - methyl - 1 - propanesulfonic acid), etc.

[0285] The hole injection layer can contain charge transfer compounds, etc., such as copper phthalocyanine, 1,4,5,8,9,12 - hexaazatriphenylenehexacarbonitrile (HAT - CN), and tetrathiafulvalene - tetracyanoquinodimethane system (TTF - TCNQ).

[0286] In some non - limiting embodiments, the hole injection layer contains at least one conductive polymer and at least one fluorinated acid polymer.

[0287] Examples of hole transporting materials for layer 130 have been outlined, for example, in Kirk-Othmer Encyclopedia of Chemical Technology by Y. Wang, Fourth Edition, Volume 18, pages 837-860, 1996. Both hole transporting molecules and polymers can be used. Commonly used hole transporting molecules are: N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N,N'-bis(4-methylphenyl)-N,N'-bis(4-ethylphenyl)-[1,1'-(3,3'-dimethyl)biphenyl]-4,4'-diamine (ETPD), tetra-(3-methylphenyl)-N,N,N',N'-2,5-benzenediamine (PDA), a-phenyl-4-N,N-diphenylaminostyrene (TPS), p-(diethylamino)benzaldehyde diphenylhydrazone (DEH), triphenylamine (TPA), bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane (MPMP), 1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl]pyrazoline (PPR or DEASP), 1,2-trans-bis(9H-carbazol-9-yl)cyclobutane (DCZB), N,N,N',N'-tetrakis(4-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TTB), N,N'-bis(naphthalen-1-yl)-N,N'-bis-(phenyl)benzidine (□-NPB), and porphyrin compounds such as copper phthalocyanine. In some embodiments, the hole transporting layer comprises a hole transporting polymer. In some embodiments, the hole transporting polymer is a stilbenylaryl compound. In some embodiments, the aryl has two or more fused aromatic rings. In some embodiments, the aryl is a polyacene. As used herein, the term "polyacene" refers to a hydrocarbon parent component containing two or more ortho-fused benzene rings arranged in a straight line. Other commonly used hole transporting polymers are polyvinylcarbazole, (phenylmethyl)-polysilane, and polyaniline. Hole transporting polymers can also be obtained by doping hole transporting molecules such as those described above into polymers such as polystyrene and polycarbonate. In some cases, triarylamine polymers, especially triarylamine-fluorene copolymers, are used. In some cases, these polymers and copolymers are crosslinkable.

[0288] In some embodiments, the hole transporting layer further comprises a p-type dopant. In some embodiments, the hole transporting layer is doped with a p-type dopant. Examples of p-type dopants include, but are not limited to, tetrafluorotetracyanoquinodimethane (F4-TCNQ) and perylene-3,4,9,10-tetracarboxylic-3,4,9,10-dianhydride (PTCDA).

[0289] In some embodiments, there are more than one hole transport layer (not shown).

[0290] Examples of electron transport materials that can be used for layer 160 include, but are not limited to, metal chelated oxinoid compounds, including metal quinolate derivatives such as tris(8-hydroxyquinolinato)aluminum (AlQ), bis(2-methyl-8-hydroxyquinolinato)(p-phenylphenolato)aluminum (BAlq), hafnium(IV) bis(8-hydroxyquinoline) (HfQ), and zirconium(IV) bis(8-hydroxyquinoline) (ZrQ); and oxazole compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), and 1,3,5-tris(phenyl-2-benzimidazole)benzene (TPBI); quinoxaline derivatives such as 2,3-bis(4-fluorophenyl)quinoxaline; fluoranthene derivatives such as 3-(4-(4-methylstyryl)phenyl-p-tolylamino)fluoranthene; phenanthroline such as 4,7-diphenyl-1,10-phenanthroline (DPA) and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (DDPA); and mixtures thereof. In some embodiments, the electron transport layer further comprises an n-type dopant. N-type dopant materials are well known. N-type dopants include, but are not limited to, Group 1 and Group 2 metals; Group 1 and Group 2 metal salts such as LiF, CsF, and Cs 2 CO 3 ; Group 1 and Group 2 metal organic compounds such as lithium quinolate; and molecular n-type dopants such as leuco dyes, metal complexes such as W 2 (hpp) 4 (where hpp = 1,3,4,6,7,8-hexahydro-2H-pyrimido-[1,2-a]-pyrimidine) and cobaltocene, tetrathiafulvalene, bis(ethylenedithio)tetrathiafulvalene, heterocyclic groups or divalent groups, and dimers, oligomers, polymers, dispiro compounds, and polycyclic compounds of heterocyclic groups or divalent groups.

[0291] In some embodiments, a quenching-resistant layer may be present between the photoactive layer and the electron transport layer to prevent quenching of blue luminance by the electron transport layer. To prevent energy transfer quenching, the singlet energy of the quenching-resistant material must be higher than that of the blue emitter. To prevent electron transfer quenching, the LUMO energy level of the quenching-resistant material must be shallow enough (relative to the vacuum level) such that electron transfer between the emitter exciton and the quenching-resistant material is endothermic. Additionally, the HOMO energy level of the quenching-resistant material must be deep enough (relative to the vacuum level) such that electron transfer between the emitter exciton and the quenching-resistant material is endothermic. Typically, the quenching-resistant material is a large bandgap material with high singlet and triplet energies.

[0292] The cathode 170 is an electrode that is particularly effective for injecting electrons or negative charge carriers. The cathode can be any metal or non-metal having a work function lower than that of the anode. Materials for the cathode can be selected from Group 1 alkali metals (e.g., Li, Cs), Group 2 (alkaline earth) metals, Group 12 metals, including rare earth elements and lanthanides, and actinides. Materials such as aluminum, indium, calcium, barium, samarium, and magnesium and combinations can be used.

[0293] Alkali metal-containing inorganic compounds such as LiF, CsF, Cs 2 O and Li 2 O, or organometallic compounds containing Li can also be deposited between the organic layer 160 and the cathode layer 170 to reduce the operating voltage. This layer (not shown) can be referred to as an electron injection layer.

[0294] It is known that there are other layers in the organic electronic device. For example, a layer (not shown) may be present between the anode 110 and the hole injection layer 120 to control the amount of positive charge injected and / or provide bandgap matching of the layers, or serve as a protective layer. Layers known in the art such as copper phthalocyanine, silicon oxynitride, fluorocarbon, silane, or ultrathin layers of metals (such as Pt) can be used. Alternatively, surface treatment can be performed on some or all of the anode layer 110, active layers 120, 130, 140, 150, and 160, or cathode layer 170 to improve charge carrier transport efficiency. The selection of materials for each component layer is preferably determined by balancing the positive and negative charges in the emitter layer to provide a device with high electroluminescence efficiency.

[0295] It should be understood that each functional layer can be composed of more than one layer.

[0296] d. Device fabrication

[0297] The device layers can be formed by any deposition technique or combination of techniques, including vapor deposition, liquid deposition, and thermal transfer.

[0298] In some embodiments, the device is fabricated by liquid-phase depositing a hole injection layer, a hole transport layer, an electron blocking layer, and a photoactive layer, and by vapor-phase depositing an anode, an electron transport layer, an electron injection layer, and a cathode. Suitable liquid-phase deposition techniques are well known in the art.

[0299] In some embodiments, all of the device layers are fabricated by vapor-phase deposition. Such techniques are well known in the art.

[0300] Examples

[0301] The concepts described herein will be further described in the following examples, which do not limit the scope of the invention as claimed.

[0302] Synthesis examples

[0303] These examples illustrate the preparation of arylamine compounds in an electron blocking layer for use in organic electronic devices as described above.

[0304] Synthesis example 1

[0305] Synthesis of compound 1-1

[0306]

[0307] Synthesis of (4'-chloro-[1,1'-biphenyl]-2-yl)dimethylsilane (2):

[0308]

[0309] n-BuLi (43.2 mL, 112.35 mmol) was added dropwise to a stirred solution of Compound-1 (20 g, 74.9 mmol) in THF (100 mL), maintained at -78 °C, and stirred at the same temperature for 30 min. Compound-1a (13.2 mL, 112.35 mmol) was added to the reaction mixture, and stirring was continued at room temperature for 12 h. The progress of the reaction was monitored by UPLC and TLC. After 12 h, UPLC showed 65.41% of Compound-2 at 4.70 RT. The reaction mixture was quenched with saturated NH 4 Cl solution (200 mL) and extracted with EtOAc (3 x 100 mL). The combined organics were dried over anhydrous Na 2 SO 4 and concentrated to give the crude compound. This crude compound was purified by column chromatography using silica gel (100 - 200 mesh) eluting with 0% - 1% EtOAc in petroleum ether to give 12 g of Compound-2 (47%), with a purity of 73.14% as determined by UPLC.1 H NMR (CDCl 3 , 400 MHz) δ 7.61 (dd, J=4.8, 3.2 Hz, 1H), 7.50 - 7.56 (m, 1H), 7.40 - 7.46 (m, 4H), 7.23 - 7.39 (m, 1H), 0.06 (s, 6H).

[0310] Synthesis of 3 - chloro - 5,5 - dimethyl - 5H - dibenzo[b,d]silole (3):

[0311]

[0312] Compound - 2 (8 g, 32.52 mmol) was charged into 1,4 - dioxane (160 mL), and RhCl(PPh 3 ) 3 (300 mg, 0.32 mmol) was added thereto. Then the reaction mixture was heated at 120 °C for 30 min. The reaction progress was monitored by TLC, and the reaction was continued until Compound - 2 was completely consumed. The reaction mixture was cooled and quenched with water (100 ml), and extracted with ethyl acetate (2 x 100 ml). The combined organic matters were dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure to obtain a crude compound. This crude compound was purified by column chromatography using silica gel (100 - 200 mesh) eluting with 5% - 10% EtOAc in petroleum ether to obtain 6.8 g of a colorless liquid, which was further purified by preparative HPLC to obtain 3 g of Compound - 3 as a colorless liquid (37%), and the purity determined by LCMS was 99.51%. 1 H NMR (CDCl 3 , 400 MHz) δ 7.71 - 7.78 (m, 2H), 7.61 (dd, J=2 Hz, 1.6 Hz, 1H), 7.56 (d, J=2 Hz, 1H), 7.41 - 7.45 (m, 1H), 7.38 (dd, J=8.4 Hz, 2.4 Hz, 1H), 7.26 - 7.36 (m, 1H), 0.42 (s, 6H)

[0313] Synthesis of 3 - bromo - 1,1':4',1'' - terphenyl (6):

[0314]

[0315] Compound - 4 (10 g, 50.5 mmol) and Compound - 5 (7.7 mL, 60.6 mmol) were charged into toluene (100 mL) and water (20 mL), and K 2 CO3 (13.93 g, 101.1 mmol). Then the reaction mixture was degassed with argon for 5 min. After adding Pd(PPh 3 ) 4 (2.9 g, 2.52 mmol) thereto, it was degassed again with argon. The reaction was continued at 110 °C for 12 h. The progress of the reaction was monitored by UPLC. After 12 h, UPLC showed that 94% of Compound-6 was formed at 4.96 RT. The reaction mixture was quenched with water (100 ml) and extracted with EtOAc (2 x 100 mL). The combined organic layers were dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure to give the crude compound. This crude compound was purified by column chromatography using silica gel, eluting with 5%-10% EtOAc in petroleum ether, to give 15 g of Compound-6 (90%) as a white solid, with a purity of 95% as determined by UPLC. 1 H NMR (CDCl 3 , 400 MHz) δ 7.69 (s, J = 4.4 Hz, 1H), 7.62 - 7.67 (m, 6H), 7.55 - 7.57 (m, 1H), 7.45 - 7.50 (m, 3H), 7.35 - 7.39 (m, 1H), 7.30 - 7.34 (m, 1H).

[0316] Synthesis of N-phenyl-[1,1':4',1”-terphenyl]-3-amine (8):

[0317]

[0318] NaOtBu (3.11 g, 32.4 mmol) was added to a stirred solution of Compound-6 (5 g, 16.2 mmol) and Compound-7 (1.78 mL, 19.41 mmol) in toluene (50 mL). The resulting mixture was degassed with argon for 5 min. Pd 2 (dba) 3 (740 mg, 0.80 mmol) and dppf (1,1′-ferrocenediyl-bis(diphenylphosphine), 896 mg, 1.6 mmol) were added to the mixture, and it was degassed again. The reaction mixture was heated at 110 °C and the reaction was continued for 12 h. The progress of the reaction was monitored by UPLC. After 12 h, UPLC showed 84% of Compound-8 at 4.68 RT. The reaction mixture was cooled and passed through Pad filtration. The filtrate was concentrated to obtain the crude compound. The obtained crude product was purified by column chromatography using silica gel, eluting with 5%-10% EtOAc in petroleum ether, to give 5 g (90%) of a brown solid with a purity of 91% as determined by UPLC. 1 HNMR(CDCl 3 , 400 MHz) δ 7.62 - 7.65 (m, 6H), 7.43 - 7.47 (m, 2H), 7.31 - 7.37 (m, 6H), 7.19 - 7.29 (m, 1H), 7.13 (dd, J = 9.6, 1.2 Hz, 2H), 7.07 (dd, J = 8.0, 1.0 Hz, 1H), 6.95 - 6.97 (m, 1H), 5.80 (s, 1H). (ESI) m / z: Calculated for C 24 H 19 N [M + H] + was 321.42; found, 322.39.

[0319] Synthesis of N-(3-bromophenyl)-N-phenyl-[1,1':4',1”-terphenyl]-3-amine (9):

[0320]

[0321] Compound -8 (3.5 g, 10.9 mmol), compound -5 (2.8 mL, 21.8 mmol) and NaOtBu (2.13 g, 21.8 mmol) were charged into toluene (35 mL), and the mixture was degassed with argon for 5 min. Pd 2 (dba) 3 (0.49 g, 0.545 mmol) and dppf (0.6 g, 1.09 mmol) were added to the reaction mixture, and the mixture was stirred at 110 °C for 16 h. The progress of the reaction was monitored by UPLC. After 16 h, UPLC showed that 76.5% of the desired peak was formed at 5.42 RT. The reaction mixture was cooled and filtered through pad. The filtrate was concentrated to obtain the crude compound. The obtained crude product was purified by column chromatography using silica gel, eluting with 5%-10% EtOAc in petroleum ether, to give 3.5 g (67%) of a brown solid with a purity of 90% as determined by UPLC. 1 HNMR(CDCl 3 , 400 MHz) δ 7.53 - 7.64 (m, 6H), 7.42 - 7.46 (m, 2H), 7.28 - 7.36 (m, 7H), 7.15 (d, J = 1.2 Hz, 2H), 7.02 - 7.71 (m, 5H). (ESI-MS) m / z: For C 30 H22 Calculated [M+H] for BrN + is 476.42; measured value, 478.23.

[0322] Synthesis of N-phenyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1':4',1''-terphenyl]-3-amine (10):

[0323]

[0324] To a stirred solution of Compound-9 (11 g, 23.1 mmol) in dioxane (110 mL) at room temperature was added B 2 Pin 2 (8.8 g, 34.6 mmol) and K 3 PO 4 (9.79 g, 46.2 mmol), and the resulting mixture was purged with argon for 5 min. Pd 2 (dba) 3 (1.05 g, 1.15 mmol) and PCy 3 .HBF 4 (1.7 g, 4.25 mmol) were added to the reaction mixture, and the mixture was stirred at 85 °C for 16 h. The progress of the reaction was monitored by UPLC. After 24 h, UPLC showed 76% of Compound-10 at 5.42 RT. The reaction mixture was cooled and filtered through a pad. The filtrate was concentrated to give the crude compound. The obtained crude product was purified by column chromatography using silica gel eluting with 5%-10% EtOAc in petroleum ether to give 8 g (66%) of a brown solid with a purity of 89% as determined by LCMS. 1 1H NMR (CDCl 3 , 400 MHz) δ 7.50 - 7.65 (m, 8H), 7.43 (t, J = 7.6 Hz, 2H), 7.34 - 7.36 (m, 2H), 7.12 - 7.34 (m, 8H), 7.10 (d, J = 0.8 Hz, 2H), 7.00 - 7.02 (m, 2H), 1.31 (s, 12H). (ESI-MS) m / z: For C 36 H 34 BNO 2 Calculated [M + H] + is 523.48; measured value, 524.56.

[0325] Synthesis of N-(3-(5,5-dimethyl-5H-dibenzo[b,d]silole-3-yl)phenyl)-N-phenyl-[1,1':4',1”-terphenyl]-3-amine (1-1):

[0326]

[0327] To a stirred solution of Compound-10 (5 g, 9.56 mmol) and Compound-3 (2.8 g, 11.46 mmol) in toluene (75 mL) was added K 2 CO 3 (4 g, 28.6 mmol), and the resulting mixture was degassed with argon for 5 min. Pd 2 (dba) 3 (0.44 g, 0.475 mmol), PCy 3 (0.53 g, 1.91 mmol) were added to the mixture, and the mixture was stirred at 100 °C for 32 h. The progress of the reaction was monitored by UPLC. After 32 h, UPLC showed the formation of 66% of the desired peak at 5.82 RT. The reaction mixture was cooled and filtered through a pad. The filtrate was concentrated to give the crude compound. The obtained crude product was purified by column chromatography using silica gel eluting with 5%-10% EtOAc in petroleum ether to give 4 g of a white solid. This white solid was further purified by dissolving in 5 volumes of CHCl 3 and co-precipitating with 10 volumes of acetonitrile to give 2.3 g (40%) of a white solid with a purity of 99.3% as determined by UPLC. 1 1H NMR (CDCl 3 , 400 MHz) δ 7.80 - 7.82 (m, 2H), 7.77 (d, J = 1.6 Hz, 1H), 7.55 - 7.66 (m, 9H), 7.44 - 7.45 (m, 5H), 7.25 - 7.36 (m, 8H), 7.19 - 7.22 (m, J = 8.8 Hz, 2H), 7.10 - 7.17 (m, 2H), 7.04 (s, 1H), 0.42 (s, 6H). (ESI-MS) m / z: Calculated for C 44 H 35 NSi [M + H] + is 605.86; found, 606.47.

[0328] Synthesis example 2

[0329] Synthesis of compound 1-71

[0330]

[0331] Synthesis of 2-Bromo-N-phenyl-N-(3-(phenanthren-2-yl)phenyl)aniline (3)

[0332]

[0333] Compound -2 (3.9 mL, 0.030 mmol) and NaOtBu (4.86 g, 0.05 mmol) were added to a stirred solution of Compound -1 (10 g, 0.025 mmol) in toluene (100 mL). The resulting mixture was degassed with argon for 5 min. Pd 2 (dba) 3 (1.15 g, 0.0012 mmol), S-Phos (2.07 g, 0.005 mmol) were added and degassed again for 5 min. The resulting reaction mixture was heated to 100 °C for 2 h. The progress of the reaction was monitored by TLC and UPLC. After 2 h, UPLC showed the formation of a 72% desired peak at 6.03 RT. The reaction mixture was cooled to room temperature, filtered through a pad and washed with excess EtOAc (200 mL). The resulting filtrate was concentrated to give the crude compound. The obtained crude product was purified by column chromatography using 100 - 200 silica gel eluting with petroleum ether to give an off-white solid (12 g, 86%). 1 H NMR (CDCl 3 , 400 MHz) δ 8.75 (d, J = 1.6 Hz, 1H), 8.64 - 8.68 (m, 5H), 7.78 (dd, J = 1.6 Hz, 1.4 Hz, 1H), 7.64 - 7.70 (m, 5H), 7.42 - 7.73 (m, 4H), 7.35 - 7.37 (m, 2H), 7.08 - 7.15 (m, 3H), 6.99 - 7.07 (m, 2H). (ESI-MS) m / z: Calculated for C 36 H 24 BrN [M] + to be 550.50; found, 550.42.

[0334] Synthesis of N-Phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(phenanthren-2-yl)phenyl)aniline (4):

[0335]

[0336] B 2 Pin 2 (3.09 g, 12.16 mmol) and K 3 PO4 (2.58 g, 12.16 mmol) was added to a stirred solution of Compound-3 (3.35 g, 6.08 mmol) in dioxane (33.5 mL), and the resulting reaction mixture was purged with argon for 5 min. Pd 2 (dba) 3 (0.278 g, 0.304 mmol) and PCy 3 (0.34 g, 1.21 mmol) were added to the reaction mixture, and the mixture was heated at 70 °C for 16 h. The progress of the reaction was monitored by TLC and UPLC. After 16 h, UPLC showed the formation of a 91% desired mass peak at 6.09 RT. The reaction mixture was cooled to room temperature, filtered through a pad, and washed with excess EtOAc (200 mL). The resulting filtrate was concentrated to give the crude compound. The obtained crude product was purified by column chromatography using 100 - 200 silica gel, eluting with 5% - 10% EtOAc in petroleum ether, to give 2.5 g (yield: 74%) of Compound-4 as a brown solid with a purity of 94%. 1 H NMR (CDCl 3 , 400 MHz) δ 8.76 (s, 1H), 8.65 - 8.71 (m, 5H), 7.79 (dd, J = 5.6, 1.6 Hz, 2H), 7.64 - 7.76 (m, 4H), 7.46 (s, 1H), 7.39 - 7.42 (m, 1H), 7.31 (d, J = 1.2 Hz, 2H), 7.23 - 7.25 (m, 3H), 7.21 - 7.22 (m, 3H), 7.18 - 7.19 (m, 1H), 7.12 - 7.15 (m, 1H), 6.96 - 7.10 (m, 1H), 1.03 (s, 12H). (ESI-MS) m / z: Calculated for C 42 H 36 BNO 2 [M + + was 597.57; found, 597.67.

[0337] Synthesis of N-phenyl-2-(9,9,10,10-tetramethyl-9,10-dihydrophenanthren-3-yl)-N-(3-(phenanthren-2-yl)phenyl)aniline (1 - 71):

[0338]

[0339] To a stirred solution of Compound-4 (2.5 g, 4.18 mmol) in dioxane (25 mL) was added Compound-5 (1.35 g, 5.01 mmol) and K 2 CO​3 (3.09 g, 12.54 mmol). The resulting reaction mixture was degassed for 5 min. Pd 2 (dba) 3 (0.19 g, 0.209 mmol) and PCy 3 (0.23 g, 0.84 mmol) were added, and it was degassed again for 5 min. The reaction was continued at 90 °C for 48 h. The progress of the reaction was monitored by TLC and UPLC. After 48 h, UPLC showed 56% of 1-71 at 6.80 RT. The reaction mixture was cooled to room temperature, filtered through a pad, and washed with excess EtOAc (200 mL). The resulting filtrate was concentrated to give the crude compound. The obtained crude product was purified by column chromatography using 100 - 200 silica gel, eluting with 5% - 10% EtOAc in petroleum ether to give 2.5 g (yield: 84%) of 1-71. The compound was further purified by recrystallization from toluene to give 1.8 g of 1-71 as an off-white solid. 1 H NMR (CDCl 3 , 400 MHz) δ 8.66 - 8.61 (m, 6H), 7.66 - 7.61 (m, 5H), 7.58 (s, 1H), 7.40 - 7.33 (m, 4H), 7.31 - 7.33 (m, 3H), 7.29, 7.11 (m, 8H), 7.05 (dd, J = 1.2 Hz, 0.8 Hz, 2H), 7.07 - 6.99 (m, 1H), 6.82 (s, 1H), 1.36 (d, J = 12.4, 6H), 0.77 (s, 6H). (ESI-MS) m / z: Calculated for C 54 H 43 N [M + H] + is 705.95; found, 706.71.

[0340] Synthesis example 3

[0341] Synthesis of compound 1-78

[0342]

[0343] Synthesis of 2-bromobenzophenanthrene (2):

[0344]

[0345] Bromine (104g, 657.8mmol) was added to a stirred solution of compound-1 (100g, 438.5mmol) in DCM (3000mL), maintained at 0°C, and stirred at room temperature for 16h. The progress of the reaction was monitored by TLC and LCMS of the reaction mass, and after 16h, LCMS showed a new peak formation of 68.3% at 4.58RT. The reaction mixture was quenched with sodium thiosulfate pentahydrate solution (400mL) and extracted with DCM (3x 500mL). The combined organics were purified by anhydrous Na 2 SO 4 The obtained crude product was purified by column chromatography using 100-200 silica gel by eluting with petroleum ether to obtain 105 g of compound-2 as an off-white solid (105 g, crude product 50%). (ESI-MS) m / z: for C 18 H 11 Br calculated [M+H] + It is 307.19; the measured value is 308.17.

[0346] Synthesis of 2-(3-chlorophenyl)triphenylene (4):

[0347]

[0348] K 2 CO 3 (15.1 g, 97.4 mmol) was added to a stirred solution of compound-2 (10.0 g, 32.43 mmol) and compound-3 (6.1 g, 38.96 mmol) in toluene (110 mL) and water (30 mL). The reaction mixture was purged with argon for 5 min and Pd(PPh 3 ) 4 4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4-[4- 2 SO 4 Drying and concentration under reduced pressure afforded the crude compound. The crude obtained was purified by column chromatography using 100-200 silica gel by eluting with petroleum ether to afford off-white solid (6.6 g, 60%). 1 H NMR (CDCl 3, 400 MHz) δ 8.82 (d, J = 1.6 Hz, 1H), 8.67 - 8.76 (m, 5H), 7.86 (dd, J = 8.4 Hz, 2 Hz, 1H), 7.79 (t, J = 3.6 Hz, 1H), 7.68 - 7.71 (m, 5H), 7.26 - 7.48 (m, 2H). (ESI-MS) m / z: Calculated for C 24 H 15 Cl [M + 2H] + is 338.8; found, 341. Synthesis of N-phenyl-3-(terphen-2-yl)aniline (6):

[0349]

[0350] To a stirred solution of Compound-4 (7.0 g, 20.7 mmol) and Compound-5 (2.31 g, 24.85 mmol) in toluene (70 mL) was added NaOtBu (4.0 g, 41.42 mmol), and the reaction mixture was purged with argon for five minutes. S-Phos (1.7 g, 4.14 mmol) and Pd 2 (dba) 3 (0.94 g, 1.03 mmol) were added, and the reaction mixture was purged with argon again for five minutes. The resulting reaction mixture was stirred at 100 °C for 16 h. The progress of the reaction was monitored by LCMS. After 16 h, LCMS showed 79.48% formation of Compound-6. The reaction mixture was cooled and filtered through a pad and washed with excess EtOAc (200 mL). The resulting filtrate was concentrated under reduced pressure to give the crude compound. The obtained crude product was purified by column chromatography using 100 - 200 silica gel to give a white solid (6.2 g, 76%). 1 H NMR (CDCl 3 , 400 MHz) δ 8.83 (d, J = 2 Hz, 1H), 8.65 - 8.73 (m, 5H), 7.86 (dd, J = 8.4, 8.8 Hz, 1H), 7.65 - 7.68 (m, 4H), 7.49 (t, J = 3.6 Hz, 1H), 7.41 (d, J = 8 Hz, 1H), 7.37 (t, J = 2.8 Hz, 1H), 7.25 - 7.33 (m, 2H), 7.13 - 7.18 (m, 3H), 6.98 (m, 1H), 5.87 (bs, 1H). (ESI-MS) m / z: Calculated for C 30 H 21 N [M + H] + is 395.51; found, 396.3.

[0351] Synthesis of 2-(2-chlorophenyl)-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (8)

[0352]

[0353] To a stirred solution of Compound-7 (1.0 g, 3.17 mmol) and Compound-8 (0.67 g, 3.81 mmol) in toluene (10 mL) and water (2 mL) was added K 2 CO 3 (0.85 g, 6.35 mmol), and then the mixture was purged with argon for 5 min. To the reactants was added Pd(PPh 3 ) 4 (180 mg, 0.16 mmol), and again the mixture was purged with argon for 5 min. The resulting reactants were heated to 110 °C for 16 h. The progress of the reaction was monitored by LCMS. After 16 h, LCMS showed that 68.3% of Compound-9 was formed at 4.83 RT. The reactants were cooled, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure to give the crude compound. The crude compound was purified by column chromatography using 100 - 200 silica gel, and the separated major compound was eluted with petroleum ether to give 2-(2-chlorophenyl)-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (0.92 g, 55%). 1H NMR (CDCl 3 , 400 MHz) δ, 7.78 - 7.82 (m, 2H), 7.52 (d, J = 2 Hz, 1H), 7.49 (dd, J = 9.2 Hz, 6.4 Hz, 1H), 7.25 - 7.45 (m, 7H). (ESI) m / z: Calculated for C 24 H 23 Cl [M] + to be 346.9; found, 346.4.

[0354] Synthesis of N-phenyl-2-(9,9,10,10-tetramethyl-9,10-dihydrophenanthren-2-yl)-N-(3-(phenanthren-2-yl)phenyl)aniline (1-78):

[0355]

[0356] To a stirred solution of Compound-6 (2.5 g, 6.33 mmol) and Compound-9 (2.6 g, 7.60 mmol) in toluene (25 mL) was added NaOtBu (1.21 g, 12.66 mmol), and the mixture was purged with argon for 5 min. S-Phos (518 mg, 1.27 mmol) and Pd 2 (dba) 3(0.29 g, 0.32 mmol) was added to the reaction mixture, which was then purged with argon again for 5 min. The resulting reaction was heated to 110 °C for 16 h. The progress of the reaction was monitored by LCMS. After 16 h, LCMS showed 70% formation of 1-78. The reaction was cooled and The mixture was filtered through a pad, washed with excess EtOAc (200 mL), and concentrated under reduced pressure to give a crude compound. The crude obtained was purified by column chromatography using 100-200 silica gel to provide 3.3 g of 1-78 (74%) as an off-white solid. Further purification by preparative HPLC gave 2.7 g of 1-78. (MS: 705.9, M+H), 1H NMR (CDCl 3, 400 MHz) δ8.70-8.81 (m, 6H), 7.68-7.72 (m, 6H), 7.62 (d, J = 8 Hz, 1H), 7.37-7.51 (m, 6H), 7.16-7.37 (m, 11H), 6.95 (d, J = 8 Hz, 2H), 6.86-6.88 (m, 2H), 1.14-1.29 (m, 6H), 0.64-0.67 (m, 6H). ESI m / z: for C 54 H 43 N calculated [M+H] + It is 705.3; the measured value is 705.7.

[0357] Synthesis example 4

[0358] Synthesis of compound 2-24

[0359]

[0360] Synthesis of 2'-chloro-[1,1'-biphenyl]-2-carboxylic acid methyl ester (3):

[0361]

[0362] Compound-2 (44.7 g, 286 mmol) and K 2 CO 3 (79.1 g, 572 mmol) was added to a stirred solution of compound-1 (50 g, 190.8 mmol) in dioxane (500 mL) and water (200 mL). The resulting mixture was purged with argon for 10 min. Then, Pd(PPh 3 ) 4(11g, 9.54 mmol), and the reactor was heated to 85 °C for 16 h. The progress of the reaction was monitored by TLC and LCMS. After 16 h, TLC showed complete consumption of Compound-1, and LCMS showed the formation of a 76.4% desired mass peak at 2.47 RT. The reaction mixture was cooled to room temperature, diluted with water (500 mL), and extracted with EtOAc (3 x 300 mL). The combined organic layers were dried over anhydrous Na 2 SO 4 and concentrated to give the crude compound. The obtained crude product was purified by column chromatography using (100 - 200 mesh silica gel) eluting with petroleum ether to give 40.8 g (87%) of Compound-3 as a gummy liquid, with a purity of 97.8% determined by UPLC. 1 1H NMR (DMSO-d6, 400 MHz) δ 7.93 (dd, J = 11 Hz, 1.5 Hz, 1H), 7.65 - 7.70 (m, 1H), 7.54 - 7.58 (m, 1H), 7.47 - 7.51 (m, 1H), 7.37 - 7.41 (m, 2H), 7.26 - 7.32 (m, 2H), 3.58 (s, 3H). (ESI-MS) m / z: For C 14 H 11 ClO 2 Calculated [M + H] + is 246.69; found, 247.24.

[0363] Synthesis of 2-(2'-chloro-[1,1'-biphenyl]-2-yl)propan-2-ol (4):

[0364]

[0365] To a stirred solution of Compound-3 (40 g, 162.15 mmol) in THF (600 mL) maintained at 0 °C was added dropwise CH 3 MgCl (3 M in THF) (324 mL, 972.8 mmol). The reaction mixture was stirred at room temperature for 16 h. After 16 h, the progress of the reaction was monitored by TLC and LCMS. TLC showed complete consumption of Compound-3. LCMS showed the formation of an 84% desired mass peak at 2.37 RT. The reaction mixture was cooled to 0 °C, quenched slowly with saturated NH 4 Cl solution and extracted with EtOAc (3 x 200 mL). The combined organic layers were dried over anhydrous Na 2 SO 4Dry and concentrate to obtain the crude compound. The obtained crude product was purified by column chromatography (silica gel, 100 - 200 mesh) by eluting with petroleum ether, providing 27.8 g of compound - 4 as a white solid (70%), with a purity of 95.2% determined by UPLC. 1 H NMR (DMSO - d 6 , 400 MHz) δ 7.82 (dd, J = 11.5 Hz, 1.5 Hz, 1H), 7.49 (dd, J = 11.5 Hz, 1.5 Hz, 1H), 7.29 - 7.39 (m, 4H), 7.22 - 7.26 (m, 1H), 6.89 (dd, J = 11 Hz, 1.5 Hz, 1H), 4.87 (s, 1H), 1.25 (s, 3H), 1.17 (s, 3H). (ESI - MS) m / z: Calculated for C 15 H 15 ClO [M + H] + is 246.69; found, 229.36.

[0366] Synthesis of 4 - chloro - 9,9 - dimethyl - 9H - fluorene (5):

[0367]

[0368] To a stirred solution of compound - 4 (22.7 g, 92.49 mmol) in DCM (455 mL) was added dropwise BF 3 .OEt 2 (17.4 mL, 138.7 mmol) while maintaining the bath temperature at 0 °C. The resulting reaction mixture was stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC and UPLC. After 16 h, TLC showed complete conversion of compound - 4 and UPLC showed the formation of 87.3% of the desired peak at 4.68 RT. The reaction mixture was cooled to 0 °C, quenched with water (200 mL), and extracted with DCM (3 x 200 mL). The combined organic layers were dried over anhydrous Na 2 SO 4 dried and concentrated to obtain the crude compound. The obtained crude product was purified by column chromatography (silica gel, 100 - 200 mesh) by eluting with 0% - 5% EtOAc in petroleum ether, giving 20.5 g of compound - 5 as a gummy liquid (86%), with a purity of 89% determined by UPLC. 1 H NMR (CDCl 3 , 400 MHz) δ 8.38 - 8.40 (m, 1H), 7.42 - 7.45 (m, 1H), 7.30 - 7.39 (m, 4H), 7.20 - 7.27 (m, 1H), 1.48 (s, 6H). (ESI - MS) m / z: For C15 H 13 Calculated [M+H] for Cl + is 228.72; measured value, 229.36.

[0369] Synthesis of ((9,9-dimethyl-9H-fluoren-4-yl)ethynyl)triisopropylsilane (6):

[0370]

[0371] In a 500 mL steel bomb, compound - 5 (18 g, 78.6 mmol) and Et 3 N (180 mL) were charged, and then the mixture was purged with argon for 5 min. Pd 2 dba 3 (3.6 g, 3.93 mmol) and X-Phos (7.5 g, 15.7 mmol) were added to the mixture, followed by the addition of TIPS acetylene (52.8 mL, 235.8 mmol). The resulting mixture was heated to 80 °C and the heating was continued for 16 h. The progress of the reaction was monitored by TLC and UPLC. After 16 h, TLC showed complete conversion of compound - 5 and UPLC showed the formation of 70.8% of the desired peak at 5.81 RT. The reaction mixture was cooled to room temperature, filtered through a pad, and washed with excess EtOAc (500 mL). The combined filtrates were concentrated to give the crude compound. The resulting crude was purified by column chromatography (230 - 400 mesh silica gel) eluting with petroleum ether to give 28 g of compound - 6 as a gummy liquid (80%), with a purity of 93.3% as determined by UPLC. 1 H NMR (CDCl 3 , 400 MHz) δ 8.67 - 8.69 (m, 1H), 7.32 - 7.46 (m, 5H), 7.22 - 7.25 (m, 1H), 1.46 (s, 6H), 1.18 - 1.22 (m, 22H). (ESI-MS) m / z: Calculated [M+H] for C 26 H 34 Si is + 374.24; measured value, 375.3.

[0372] Synthesis of 4-(iodoethynyl)-9,9-dimethyl-9H-fluorene (7):

[0373]

[0374] To a stirred solution of Compound-6 (28 g, 74.8 mmol) in acetonitrile (280 mL) was added NIS (25.2 g, 112.29 mmol) and AgF (14.2 g, 112.29 mmol). The reaction mixture was stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC and UPLC. After 16 h, TLC showed complete conversion of Compound-6, and UPLC showed formation of 93% of the desired peak at 4.69 RT. The reaction mixture was passed through washing with excess EtOAc (500 mL) and concentrated to give the crude compound. The resulting crude product was purified by column chromatography (silica gel, 100 - 200 mesh) eluting with 0% - 5% EtOAc in petroleum ether to afford 22.5 g of Compound-7 as a pale yellow solid (87%), with a purity of 97.8% as determined by UPLC. 1 H NMR (CDCl 3 , 400 MHz) δ 8.31 - 8.34 (m, 1H), 7.35 - 7.46 (m, 5H), 7.26 - 7.26 (m, 1H), 1.46 (s, 6H). (ESI-MS) m / z: calculated [M + H] 17 H 13 for C + H

[0375] Synthesis of 8-bromo-4,4-dimethyl-4H-cyclopenta[def]phenanthrene (8a):

[0376]

[0377] To a stirred solution of Compound-7 (7 g, 20.34 mmol) in nitromethane (70 mL) at room temperature was added CuBr 2 (13.6 g, 61.04 mmol) and K 3 PO 4 (2.16 g, 10.18 mmol), and the mixture was stirred for 16 h. The progress of the reaction was monitored by TLC and UPLC. After 16 h, TLC showed complete conversion of Compound-7, and UPLC showed formation of 67% of Compound-8a at 4.49 RT. The reaction mixture was passed through a pad and washed with excess EtOAc (300 mL). The filtrate was concentrated to give the crude compound. The resulting crude product was purified by column chromatography (silica gel, 100 - 200 mesh) eluting with 0% - 5% EtOAc in petroleum ether to give 6 g of Compound-8a as an off-white solid (84%), with a purity of 84.34% as determined by UPLC. 1 H NMR (CDCl3 , 400 MHz) δ 7.68 - 7.71 (m, 1H), 7.44 - 7.47 (m, 2H), 7.32 - 7.40 (m, 3H), 7.15 (dd, J = 11 Hz, 1.5 Hz, 1H), 1.49 (s, 3H), 1.48 (s, 3H). (ESI-MS) m / z: Calculated for C 17 H 13 Br [M + H] + is 297.20.

[0378] Synthesis of N-(3-(4,4-dimethyl-4H-cyclopenta[def]phenanthren-8-yl)phenyl)-N-phenyl-[1,1':4',1''-terphenyl]-3-amine (2-24):

[0379]

[0380] To a stirred solution of Compound-8a (5 g, 16.83 mmol) in dioxane (100 mL) and water (20 mL) was added Compound-9 (8.8 g, 16.8 mmol) and NaOH (2.02 g, 50.5 mmol). The resulting mixture was purged with argon for 5 min. Pd(PPh 3 ) 4 (0.97 g, 0.841 mmol) was added, and the mixture was heated to 80 °C, whereupon the reaction was continued for 2 h. The progress of the reaction was monitored by TLC and UPLC. After 2 h, TLC showed complete conversion of Compound-8a, and UPLC showed formation of 42.5% of the desired peak at 6.07 RT and 32.2% of Compound-9a at 6.22 RT. The reaction mixture was passed through a pad and washed with excess EtOAc (300 mL). The filtrate was concentrated to give the crude compound. The resulting crude was purified by column chromatography (100 - 200 mesh silica gel) eluting with 0% - 2% EtOAc in petroleum ether to give 7 g of 2-24 as a white solid. The resulting solid was co-precipitated several times using chloroform and acetonitrile to give 1.74 g of 2-24 (17%) as an off-white solid, with a purity of 99.3% as determined by UPLC. 1 H NMR (CDCl 3 , 400 MHz) δ 8.47 (d, J = 9.5 Hz, 1H), 7.58 - 7.64 (m, 6H), 7.38 - 7.46 (m, 7H), 7.28 - 7.37 (m, 8H), 7.19 - 7.24 (m, 3H), 7.08 - 7.19 (m, 3H), 1.46 (s, 6H). (ESI-MS) m / z: Calculated for C 47 H35 N Calculated for [M+H] + is 613.80; Measured value, 614.6

[0381] Synthesis example 5

[0382] Synthesis of compound 2-32

[0383]

[0384] Synthesis of 3-Bromo-N-phenyl-N-(3-(tetracen-2-yl)phenyl)aniline (3)

[0385]

[0386] Compound -2 (3.9 mL, 30.3 mmol) and NaOtBu (4.86 g, 50.6 mmol) were added to a stirred solution of Compound -1 (10 g, 25.3 mmol) in toluene (100 mL). The reactor was purged with argon for five minutes. Then Pd 2 (dba) 3 (1.15 g, 1.26 mmol) and S-Phos (2.07 g, 5.06 mmol) were added, and the resulting mixture was heated at 100 °C for 16 h. The progress of the reaction was monitored by UPLC. After 16 h, UPLC showed a 43% desired peak at 6.20 RT. The reaction mixture was cooled and filtered through a pad and washed with excess EtOAc (300 mL). The filtrate was concentrated to give the crude compound. The obtained crude product was purified by column chromatography using silica gel (100 - 200 mesh) eluting with 15% - 20% EtOAc in petroleum ether to give 7.1 g of Compound -3 (51%) as an off-white solid with a purity of 94.7% as determined by UPLC. 1 H NMR (CDCl 3 , 400 MHz) δ 8.75 (d, J = 2 Hz, 1H), 8.64 - 8.67 (m, 5H), 7.78 - 7.80 (m, 1H), 7.65 - 7.68 (m, 4H), 7.53 (t, J = 3.6 Hz, 1H), 7.48 (s, 1H), 7.43 (m, 1H), 7.30 - 7.34 (m, 3H), 7.20 (dd, J = 8.8 Hz, 1.2 Hz, 2H), 7.10 - 7.13 (m, 5H). (ESI-MS) m / z: For C 36 H 24 BrN Calculated for [M+H] + is 550.50; Measured value, 551.46.

[0387] Synthesis of N-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3-(phenanthren-2-yl)phenyl)aniline (4)

[0388]

[0389] To a stirred solution of Compound-3 (7 g, 12.72 mmol) in dioxane (70 mL) was added B 2 Pin 2 (6.43 g, 25.45 mmol) and KOAc (2.5 g, 25.45 mmol). The reactor was purged with argon for five minutes. PdCl 2 dppf.DCM (0.91 g, 1.27 mmol) was added to the reaction mixture, and it was heated at 85 °C for 16 h. The progress of the reaction was monitored by UPLC. After 16 h, UPLC showed an 81.2% desired mass peak. The reaction mixture was cooled and filtered through a pad and washed with excess EtOAc (300 mL). The filtrate was concentrated to give the crude compound. The obtained crude product was purified by column chromatography using silica gel of 100 - 200 mesh, eluting with 30% - 40% EtOAc in petroleum ether, to give 5.7 g of Compound-4 as an off-white solid (75%), with a purity of 99% as determined by UPLC. 1 1H NMR (CDCl 3 , 400 MHz) δ 8.75 (d, J = 1.2 Hz, 1H), 8.62 - 8.68 (m, 5H), 7.78 (dd, J = 6.8 Hz, 1.6 Hz, 1H), 7.64 - 7.70 (m, 5H), 7.49 - 7.55 (m, 2H), 7.37 - 7.42 (m, 2H), 7.27 - 7.30 (m, 3H), 7.16 - 7.17 (m, 2H), 7.02 - 7.09 (m 2H), 1.32 (s, 12H). (ESI-MS) m / z: Calculated for C 42 H 36 BNO 2 Calculated [M + H] + to be 597.57; found, 598.58.

[0390] Synthesis of N-phenyl-3-(9,9,10,10-tetramethyl-9,10-dihydropyrene-4-yl)-N-(3-(phenanthren-2-yl)phenyl)aniline (2 - 32)

[0391]

[0392] To a stirred solution of Compound-5 (2 g, 5.18 mmol) in 1,2-DME (16 mL) and water (4 mL) was added Compound-4 (3.71 g, 6.21 mmol) and Ba(OH) 2 (3.26 g, 10.36 mmol). The resulting mixture was purged with argon for 5 min. Pd(PPh 3 ) 4 (0.3 g, 0.259 mmol) was added to the reaction mixture and heated at 100 °C for 16 h. The progress of the reaction was monitored by LCMS. After 16 h, LCMS showed 60.4% of 2-32 at 4.82 RT. The reaction mixture was diluted with DCM and dried over anhydrous Na 2 SO 4 and concentrated to give the crude compound. The obtained crude was purified by column chromatography using 100 - 200 silica gel to give 1.4 g (yield: 57%) of 2-32 as an off-white solid, purity >99% as determined by UPLC. 1 1H NMR (CDCl 3 , 400 MHz) δ 8.95 - 8.87 (m, 2H), 8.80 - 8.85 (m, 4H), 7.78 - 7.82 (m, 1H), 7.73 - 7.74 (m, 2H), 7.70 - 7.72 (m, 4H), 7.64 - 7.69 (m, 4H), 7.54 - 7.60 (m, 2H), 7.50 - 7.52 (m, 2H), 7.36 - 7.40 (m, 3H), 7.09 - 7.27 (m, 7H), 1.58 - 1.60 (m, 6H), 0.95 - 0.83 (s, 6H). (ESI-MS) m / z: calculated for C 56 H 43 N [M + H] + to be 729.97; found, 730.82.

[0393] Synthesis example 6

[0394] Synthesis of compound 3-60

[0395]

[0396] Synthesis of 5-(2-chlorophenyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydroanthracene (3)

[0397]

[0398] Compound-1 (18 g, 56.73 mmol), Compound-2 (11.53 g, 73.75 mmol) and K 2CO 3 (15.6 g, 113.47 mmol) was charged into toluene (180 mL) and water (36 mL). The reaction mixture was purged with argon for 5 min. Then, Pd(PPh 3 ) 4 (3.3 g, 2.83 mmol) was added, and the mixture was purged again for 5 min, then the resulting solution was refluxed for 5 h. The progress of the reaction was monitored by UPLC. After 5 h, UPLC showed that 62.71% of compound - 3 was formed at 5.07 RT. The reaction mixture was cooled and filtered through a pad and washed with excess EtOAc. The combined organic matters were washed with water and dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure to give the crude compound. The obtained crude product was purified by column chromatography eluting with petroleum ether and then further purified by trituration with ethanol to give a white solid (15 g, 74%). 1H NMR (CDCl 3 , 400 MHz) δ δ 7.82 (s, 1H), 7.79 (d, J = 8 Hz, 1H), 7.53 - 7.55 (m, 1H), 7.43 (s, 1H), 7.35 - 7.41 (m, 4H), 7.24 - 7.27 (m, 1H), 1.70 - 1.78 (m, 4H), 1.42 (s, 3H), 1.38 (s, 3H), 1.24 (s, 3H), 1.19 (s, 3H).

[0399] Synthesis of N - phenyl - 2 - (5,5,8,8 - tetramethyl - 5,6,7,8 - tetrahydroanthracen - 1 - yl) - N - (3 - (2 - benzophenanthryl)phenyl)aniline (3 - 60)

[0400]

[0401] To a stirred solution of compound - 3 (9.2 g, 26.30 mmol) and compound - 4 (8 g, 20.23 mmol) in toluene (80 mL) was added NaOtBu. The resulting reaction mixture was degassed for 5 min. Pd 2 (dba) 3 (0.96 g, 1.01 mmol) and t - Bu 3 P.HBF 4 (1.66 g, 4.05 mmol) were added, and the reactor was purged with argon for 5 min. The resulting solution was refluxed for 3 h. The progress of the reaction was monitored by UPLC. After 3 h, UPLC showed that 83% of 3 - 60 was formed at 6.83 RT. (ESI - MS) m / z: [M + H] +707.6. The reaction mixture was cooled and filtered through a pad and washed with excess EtOAc. The combined filtrates were concentrated under reduced pressure to give the crude compound. The crude obtained was purified by column chromatography eluting with 0%-2% EtOAc in petroleum ether to give 5.6 g of 3-60. The resulting compound was co-precipitated using THF (3V) and acetonitrile (10V) to give compound 3-60 as a white solid (5.1 g, 36%). 1H NMR (CDCl 3 , 400 MHz) δ; 8.58 - 8.68 (m, 5H), 8.59 (d, J = 8.4 Hz, 1H), 7.60 - 7.69 (m, 7H), 7.35 - 7.57 (m, 5H), 6.94 - 7.03 (m, 7H), 6.68 - 6.84 (m, 4H); 1.53 - 1.69 (m, 4H), 1.32 - 1.33 (m, 6H), 1.20 (s, 3H), 1.10 (s, 3H).

[0402] Synthesis example 7

[0403] Synthesis of compound 3-68.

[0404]

[0405] Scheme 7: Synthetic route of 3-68;

[0406] (5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)aniline 3 was synthesized. (2-Aminophenyl)boronic acid 1 (4.36 g, 31.84 mmol), 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-anthracene 2 (10 g, 31.52 mmol), Cl 2 Pd(amphos) (223 mg, 0.315 mmol), K 2 CO 3A mixture of (13.07 g, 94.56 mmol), ethanol (40 ml), water (20 ml) and toluene (100 ml) was degassed and stirred at 90 °C for 80 min under a nitrogen atmosphere. Thereafter, the mixture was cooled, the toluene layer was separated, washed with water, and passed through silica gel. The toluene was distilled off to a minimum amount, the residue was triturated with hexane and passed through a filter packed with silica gel, which was eluted gradiently with hexane, then a mixture of hexane and dichloromethane, and pure dichloromethane. The fractions containing the product were combined, the eluate was evaporated and dried in vacuo to give 9.84 g (95%) of (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)aniline 3 as an oil, and the purity determined by UPLC was 99.67%. (ESI-MS) m / z: [M+H] + = 330. 1 H-NMR(CD 2 Cl 2 ): 1.395(s, 6H), 1.405(s, 6H), 1.79(s, 4H), 3.83(br.S, 2H), 6.78(dd, 1H, J1 = 1 Hz, J2 = 10 Hz), 6.81(dt, 1H, J1 = 1.5 Hz, J2 = 10 Hz), 7.14(dt, 1H, J1 = 2 Hz, J2 = 10 Hz), 7.18(dd, 1H, J1 = 2.5 Hz, J2 = 9 Hz), 7.44(dd, 1H, J1 = 2 Hz, J2 = 11 Hz), 7.79 - 7.82(m, 4H).

[0407] Synthesis of 2-(3-chlorophenyl)picene 6. A mixture of 2-bromopicene 4 (5.5059 g, 16.47 mmol), 3-chlorophenylboronic acid 5 (3.68 g, 24.705 mmol), Pd(PPh 3 ) 4 (1.91 g, 1.653 mmol), K 2 CO 3 (6.83 g, 49.41 mmol), ethanol (80 ml), water (40 ml) and toluene (200 ml) was degassed and stirred at 95 °C for 18 h under a nitrogen atmosphere. Thereafter, the reaction mixture was cooled, diluted with water, the toluene layer was separated and passed through a filter packed with silica gel and florisil eluted with toluene. The residue after evaporation of toluene was triturated with ethanol and the initial precipitate was collected by filtration. The above crude product was dissolved in dichloromethane and adsorbed in The product was purified by chromatography on a silica gel column using a gradient elution from hexane to a mixture of hexane and dichloromethane. The fractions containing the high purity portion of the product were combined, the eluent was evaporated to a minimum amount, the precipitate was filtered, washed with hexane, and dried in a vacuum to obtain 1.92 g of 2-(3-chlorophenyl)triphenylene 6 as a white powder with a purity of >99.95% as determined by UPLC. Lower purity material (ESI-MS) m / z: [M+H] was also obtained from the tail fraction. + =338. 1 H-NMR (CDCl 3 ): 7.40-7.42(m,1H),7.47(t,1H,J=8Hz),7.69-7.73(m,5H),7.80(t,1H,J=2 Hz), 7.87 (dd, 1H, J1 = 2Hz, J2 = 9Hz), 8.67-8.77 (m, 5Hz), 8.83 (d, 1H, J = 2Hz).

[0408] Synthesis of N-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)-phenyl)-3-(triphenylene-2-yl)aniline 7. (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)aniline 3 (1.867 g, 5.67 mmol), 2-(3-chlorophenyl)triphenylene 6 (1.92 g, 5.67 mmol), Pd 2 (dba) 3 A mixture of 1,4-dihydro-1-nitropropene (104 mg, 0.113 mmol), tri-tert-butylphosphine (80 mg, 0.395 mmol), sodium tert-butoxide (0.654 g, 6.804 mmol) and toluene (100 ml) was stirred at 85° C. for 21 hours under a nitrogen atmosphere. After the reaction mixture was cooled, it was passed through a filter filled with florisil and silica gel eluted with dichloromethane. The residue after evaporation of the solvent was dissolved in dichloromethane and absorbed in The mixture was concentrated to 400 μl and subjected to chromatography on a silica gel column using a gradient elution from hexane to a mixture of hexane and dichloromethane. The fractions containing high-purity material were combined, the eluent was evaporated to a volume of about 15 ml and decanted hot. The residue was dried in a vacuum to give 2.08 g of N-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)-phenyl)-3-(triphenylene-2-yl)aniline 7 as a white amorphous solid with a purity of 99.99% as determined by UPLC. A lower purity material (0.94 g) was also obtained after evaporation of the filtrate. (ESI-MS) m / z: [M+H] + =632. 1 H-NMR (CDCl3 ): 1.42(s,6H),1.43(s,6H),1.56(br.S,1H),1.80(s,4H),7.07(t,1H,J=7Hz),7 .16(d,1H,J=7Hz),7.34(t,1H,J=10Hz),7.38(dd,2H,J1=2Hz,J2=10Hz),7.42(d, 1H,J=8Hz),7.45-7.46(m,1H),7.51(dd,1H,J1=2Hz,J2=10Hz),7.57(d,1H,J=8H z),7.67-7.70(m,4H),7.83-7.89(m,5H),8.67-8.75(m,5H),8.83(d,1H,J=2Hz).

[0409] Synthesis of compound 3-68. N-phenyl, N-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)-phenyl)-3-(triphenylene-2-yl)aniline 8. N-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)-phenyl)-3-(triphenylene-2-yl)aniline 7 (2.08 g, 3.3 mmol), bromobenzene (2.58 g, 16.45 mmol), Pd 2 (dba) 3 A mixture of 1,4-dihydro- ... The product was purified by chromatography on a silica gel column using a gradient elution from hexane to a mixture of hexane and dichloromethane. The fractions containing high-purity material were combined, the eluent was evaporated, and the residue was dissolved in about 150 ml of hot hexane. The precipitate was collected by filtration and dried in a vacuum to give 1.708 g of N-phenyl, N-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracen-2-yl)-phenyl)-3-(triphenylene-2-yl)aniline (Compound 3-68) 8 as a white powder with a purity of 99.99% as determined by UPLC. (ESI-MS) m / z: [M+H] + =708. 1 H-NMR (CDCl 3): 1.26 (s, 6H), 1.28 (s, 6H), 1.67 (s, 4H), 6.83 - 6.90 (m, 2H), 7.02 (d, 2H, J = 11 Hz), 7.10 - 7.18 (m, 5H), 7.32 - 7.46 (m, 7H), 7.52 - 7.67 (m, 7H), 8.51 - 8.66 (m, 6H).

[0410] Device example

[0411] These examples demonstrate the fabrication and testing of the organic electronic devices as described above.

[0412] Device fabrication

[0413] Bottom-emitting devices are fabricated on a patterned indium tin oxide (ITO)-coated glass substrate. The cleaned substrate is loaded into a vacuum chamber. Once the pressure reaches 5 x 10-7 Torr or less, they sequentially receive the following thermal evaporations: 10 nm of NDP-9:HT1 (37:937) as the hole injection layer, 160 nm of HT1 as the hole transport layer, 10 nm of the electron blocking layer, 30 nm of BD1:BH1 or BD2:BH1 (3:97) as the emission layer, and 30 nm of ET1:LiQ (1:1) as the electron transport layer.

[0414]

[0415] The bottom-emitting devices are thermally evaporated with an Al cathode material. Then the chamber is evacuated, and the devices are encapsulated using a glass cover, a desiccant, and a UV-curable epoxy. The device electroluminescence is measured using a PR750 spectrometer, and the quantum efficiency is calculated assuming a Lambertian light output distribution.

[0416] The SOP values are measured in the devices using cyclic voltammetry. The OLED drive voltage is ramped from -10 V until the device just turns on and then back to -10 V repeatedly, and the displacement current is recorded during this process. The onset of the injection current is observed to be shifted due to the SOP in the layer of interest. The shift relative to a material with a known SOP is used to determine the SOP of the layer of interest. Finally, all SOP values are referenced to N,N′-bis(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine, which is assumed to have an SOP of 0 V / nm.

[0417] The device efficiency and polarization of the EBL are listed in Tables 1a and 1b. The data in Table 1a are plotted in Figure 4 in.

[0418] Table 1a

[0419]

[0420] A 1:1 mixing ratio by weight

[0421] Table 1b

[0422]

[0423] Data shows that when the polarization of the EBL is within ±25 mV / nm of the EML polarization, the device efficiency is improved compared to the reference EBL. In most cases, a reduction in the operating voltage is also observed. By reducing the polarization difference between the EML and the adjacent layer (in this case, the EBL), the device efficiency is improved while maintaining a low operating voltage.

[0424] In addition, the polarization can be fine-tuned by co-depositing two materials with different polarizations (data shown in Table 1b). This result provides a simple solution to optimize the polarization of the EBL layer to work with a variety of different blue host materials to achieve the benefits disclosed herein.

[0425] It should be noted that not all of the activities described above in the general description or examples are required, some specific activities may not be required, and one or more other activities may be performed in addition to those described. Also, the order of the recited activities need not be the order in which they are implemented.

[0426] In the foregoing specification, concepts have been described with reference to specific embodiments. However, one of ordinary skill in the art understands that various modifications and changes can be made without departing from the scope of the invention as set forth in the following claims. Accordingly, the specification and drawings are to be regarded as illustrative rather than restrictive, and all such modifications are intended to be included within the scope of the invention.

[0427] Benefits, other advantages, and solutions to problems have been described above with respect to specific embodiments. However, a benefit, an advantage, a solution to a problem, and any feature or features that may cause any benefit, advantage, or solution to occur or become more apparent are not to be construed as a critical, necessary, or essential feature of any or all of the claims.

[0428] It is to be understood that, for the sake of clarity, certain features described herein in the context of separate embodiments may also be provided in combination in a single embodiment. Conversely, for the sake of brevity, the various features described in the context of a single embodiment may also be provided separately or in any sub-combination. The use of numerical values within the various ranges specified herein is expressed as an approximation, as if the word "about" preceded both the minimum and maximum values within the stated range. In this manner, minor variations above and below the stated range can be used to achieve substantially the same result as the values within the range. Moreover, the disclosure of these ranges is intended as a continuous range including every value between the minimum and maximum averages, including fractional values that may result when some components of one value are mixed with components of a different value. Additionally, when broader and narrower ranges are disclosed, matching the minimum value from one range with the maximum value from another range is also contemplated within the scope of the present invention, and vice versa.

Claims

1. A composition comprising: A mixture of a first compound and a second compound; wherein The first compound has a different chemical structure than the second compound; wherein The first compound and the second compound have a molecular weight between 300 and 1000; in The first compound and the second compound have a glass transition temperature (T g );in The first compound and the second compound each contain one or more arylamine groups; wherein The first compound has a concentration C1 in the mixture; wherein The second compound has a concentration C2 in the mixture; in C1 is between 1 wt.% and 99 wt.%; and C2 is between 1wt.% and 99wt.%; wherein The film formed by the first compound has a spontaneous orientation polarization SOP-1; wherein The film formed from the second compound has a spontaneous orientation polarization SOP-2; and The absolute value of the difference between SOP-1 and SOP-2 is greater than or equal to 10 mV / nm.

2. The composition of claim 1; wherein The first compound and the second compound each include an arylamine group.

3. The composition of claim 1; wherein The first compound and / or the second compound has a chemical structure given by Formula 1: in X represents -O-, -S-, -Si(R')(R")-, -N(R)-, -C(R')(R")-, -Se- or (R')(R")CC(R'")(R""); R, R' and R" each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, -L2-N-(Ar3)(Ar4) or -L3-N(Ar5)-L4-N-(Ar6)(Ar7); or R' and R" may be connected to each other to form one or more rings, and R' and R" may be the same or different; Ar1-Ar7 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, wherein if there are a plurality of Ar1-Ar7, each of adjacent Ar1-Ar7 may be the same or different; wherein if Ar1-Ar7 each independently represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, adjacent Ar1-Ar7 may be connected to each other via a single bond to form one or more rings; L1-L4 represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; R 1 and R 2 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) 30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, wherein if there are multiple R 1 and / or R 2 , then each can be the same or different in each occurrence, and the adjacent R 1 and / or R 2 R on the group or adjacent ring 1 and / or R 2 The groups may be linked together to form a 5- or 6-membered alicyclic ring, a carbocyclic aromatic ring, a heteroaromatic ring, or a substituted derivative thereof; a and b each independently represent an integer between 0 and 4, provided that when the bond with L1 is attached to a 1 or R 2 The maximum value of a or b is 3 when the ring is n represents 1 or 2.

4. The composition of claim 3; wherein The first compound and / or the second compound is selected from the group consisting of Formula 1-1 to Formula 1-79.

5. The composition of claim 1; wherein The first compound and / or the second compound has a chemical structure given by Formula 2: in Y is the same or different at each occurrence and represents -O-, -S-, -Si(R')(R")-, -N(R)-, C(R')(R")-, -Se-, or (R')(R")CC(R'")(R""); R, R' and R" each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, -L2-N-(Ar3)(Ar4) or -L3-N(Ar5)-L4-N-(Ar6)(Ar7); or R' and R" may be connected to each other to form one or more rings, and R' and R" may be the same or different; Ar3-Ar9 each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, wherein if a plurality of Ar3-Ar9 are present, each of Ar3-Ar9 may be the same or different; wherein If Ar3-Ar9 each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, adjacent Ar3-Ar9 may be linked to each other via a single bond to form one or more rings; L2-L5 represent a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; R 3 -R 5 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) 30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, wherein if there are multiple R 3 -R 5 , then each may be the same or different at each occurrence; and the adjacent R 3 and / or R 4 and / or R 5 R on the group or adjacent ring 3 and / or R 4 and / or R 5 The groups may be linked together to form a 5- or 6-membered alicyclic ring, a carbocyclic aromatic ring, a heteroaromatic ring, or a substituted derivative thereof; c and e each independently represent an integer between 0 and 3, provided that when the bond to L5 is attached to a 3 or R 5 The maximum value of c or e is 2; d represents an integer between 0 and 2, provided that when the bond to L5 is attached to a ring with R 4 When the ring is , the maximum value of d is 1; and n represents 1 or 2.

6. The composition of claim 5; wherein The first compound and / or the second compound is selected from the group consisting of Formula 2-1 to Formula 2-65.

7. The composition of claim 1; wherein The first compound and / or the second compound has a chemical structure given by Formula 3: in Ar 10 -Ar 11 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, wherein if there are multiple Ar3-Ar9, then Ar 10 -Ar 11 Each of may be the same or different; wherein If Ar 10 -Ar 11 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, then adjacent Ar3-Ar9 may be connected to each other via a single bond to form one or more rings; L6 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group, R 6 , R 7 and R 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) 30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, wherein if there are multiple R 6 , R 7 and / or R 8 , then each may be the same or different at each occurrence; and the adjacent R 6 and / or R 7 and / or R 8 R on the group or adjacent ring 6 and / or R 7 and / or R 8 The groups may be linked together to form a 5- or 6-membered alicyclic ring, a carbocyclic aromatic ring, a heteroaromatic ring, or a substituted derivative thereof; f represents an integer between 0 and 8, g represents an integer between 0 and 2, and h represents an integer between 0 and 4, provided that when the bonds to L6 are respectively attached to the bonds with R 7 or R 8 When the ring is , the maximum value of g is 1 and the maximum value of h is 3.

8. The composition of claim 7; wherein The first compound and / or the second compound is selected from the group consisting of Formula 3-1 to Formula 3-79.

9. The composition of claim 1; wherein The first compound and / or the second compound comprises one or more deuterium atoms.

10. A film comprising: A mixture of a first compound and a second compound; in The first compound has a different chemical structure than the second compound; in The first compound and the second compound have a molecular weight between 300 and 1000; in The first compound and the second compound have a glass transition temperature greater than 105°C; in The first compound and the second compound each comprise one or more arylamine groups; in The film formed by the first compound has a spontaneous orientation polarization SOP-1; wherein The thin film formed from the second compound has a spontaneous orientation polarization SOP-2; and the absolute value of the difference between SOP-1 and SOP-2 is greater than or equal to 10 mV / nm.

11. The thin film according to claim 10; wherein the thin film has a thickness between 1 nm and 200 nm.

12. An organic electronic device, comprising: an anode; a hole transport layer; an electron blocking layer; a light-emitting layer; an electron transport layer; and a cathode; wherein the light-emitting layer contains a host and a dopant; wherein the light-emitting layer has a spontaneous orientation polarization SOP-EML; wherein the electron blocking layer has a spontaneous orientation polarization SOP-EBL; such that the absolute value of the difference between SOP-EML and SOP-EBL is less than or equal to 25 mV / nm.

13. The organic light-emitting device according to claim 12; wherein: 10 mV / nm < SOP-EML < 100 mV / nm; and 10 mV / nm < SOP-EBL < 100 mV / nm.

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