Electroactive compound

Abstract

Provided is a polycyclic aromatic compound having a single boron-nitrogen bond and comprising a nuclear structure of nucleus A, nucleus B, or nucleus C. In these formulas: Q<supgt;1< / supgt> and Q<supgt;2< / supgt> are the same or different and are a single bond, O, S, NR<supgt;12< / supgt>, BR<supgt;12< / supgt>, CR<supgt;13< / supgt>R<supgt;14< / supgt>, and SiR<supgt;13< / supgt>R<supgt;14< / supgt>; and R<supgt;12< / supgt>-R<supgt;14< / supgt> are the same or different and are an alkyl group, a carbocyclic aryl group, a heteroaryl group, or a substituted derivative thereof.

Description

[0001] Claim of the benefit of the earlier application

[0002] This application claims the benefit of U.S. Provisional Application No. 62 / 951,040, filed Dec. 20, 2019, which is hereby incorporated by reference in its entirety. BACKGROUND OF THE INVENTION FIELD OF THE INVENTION

[0003] The present disclosure generally relates to electroactive compounds and their use in electronic devices.

[0004] Description of the related art

[0005] 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 sandwiched 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.

[0006] It is well known to use organic electroluminescent compounds as active components in light-emitting diodes. It is known that simple organic molecules, such as anthracene, thiadiazole derivatives, and coumarin derivatives, exhibit electroluminescence. It is also known that metal complexes, particularly iridium complexes and platinum complexes, exhibit electroluminescence. In some cases, these small molecule compounds are present as dopants in a host material to improve processing characteristics and / or electronic characteristics.

[0007] There is a continuing need for new electroactive compounds that can be used as hosts or electroluminescent materials. SUMMARY OF THE INVENTION

[0008] There is provided a polycyclic aromatic compound having a single boron-nitrogen bond and comprising a nuclear structure of nucleus A, nucleus B, or nucleus C,

[0009]

[0010] wherein:

[0011] Q 1 and Q 2 are the same or different and are selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ; and

[0012] R 12 -R 14are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof.

[0013] There is further provided a compound having the formula I, formula II, formula III, formula IV, formula V, or formula VI,

[0014]

[0015]

[0016] wherein:

[0017] Q 1 -Q 4 are the same or different and are selected from the group consisting of: single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0018] Q 5 and Q 6 are the same or different and are selected from the group consisting of: N, B, P(O), CR 13 , and SiR 13 ;

[0019] Q 7 and Q 8 are the same or different and are selected from the group consisting of: no bond, single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0020] R 1 -R 11 is the same or different each time it appears and is selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium, where adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, aromatic carbocyclic ring, heteroaromatic ring, or substituted derivative thereof;

[0021] R 12 -R14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0022] a, a1, b, and b1 are the same or different and are integers from 0 to 3; and

[0023] c, d, and e - h are the same or different and are integers from 0 to 2.

[0024] There is further provided a polycyclic aromatic compound having two boron - nitrogen bonds and having Formula VII, Formula VIII, Formula IX, Formula X, or Formula XI,

[0025]

[0026]

[0027] wherein:

[0028] Q 1 、Q 2 、Q 9 and Q 10 are the same or different and are selected from the group consisting of: single bond, O, S, NR 12 、BR 12 、CR 13 R 14 、and SiR 13 R 14 ;

[0029] R 1 、R 2 、R 6 、R 7 、R 9 and R 10 are the same or different in each occurrence and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germyl, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5 - or 6 - membered alicyclic ring, aromatic carbocyclic ring, heteroaromatic ring, or substituted derivatives thereof;

[0030] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0031] R 15 and R 16 are the same or different at each occurrence and are selected from the group consisting of: H, D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germyl, where adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0032] a, a1, b, and b1 are the same or different and are integers from 0 to 3; and

[0033] c and d are the same or different and are integers from 0 to 2.

[0034] Also provided is an organic electronic device comprising a first electrical contact, a second electrical contact, and a photoactive layer therebetween, the photoactive layer comprising a compound having a nucleus as described above.

[0035] 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. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Embodiments are illustrated in the drawings to enhance understanding of concepts presented herein.

[0037] Figure 1 A diagram of an example of an organic electronic device is included that contains the novel compounds described herein.

[0038] Figure 2 A diagram of another example of an organic electronic device is included that contains the novel compounds described herein.

[0039] Those skilled in the art will appreciate 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 objects in the figures may be exaggerated relative to other objects to assist in enhancing understanding of the embodiments. DETAILED DESCRIPTION

[0040] Numerous aspects and embodiments have been described above, 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.

[0041] Other features and advantages of any one or more embodiments will be apparent from the following detailed description and from the claims. The detailed description first presents definitions and clarifications of terms, followed by compounds containing nuclei A to C; compounds having Formulas I to VI; compounds having Formulas VII to XI; devices, and finally examples.

[0042] 1. Definition and clarification of terms

[0043] Before presenting the details of the following embodiments, some terms are defined or clarified.

[0044] Unless otherwise specifically defined, R, R’, R”, and any other variables are general nomenclature. Specific definitions given herein for a formula control that formula.

[0045] As used herein, the term “adjacent” when referring to substituents means groups bonded to carbons joined together by single or multiple bonds. The following show exemplary adjacent R groups:

[0046]

[0047] The term “alkoxy” is intended to mean the group RO—, where R is alkyl.

[0048] 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.

[0049] In some embodiments, the alkyl has 1-20 carbon atoms.

[0050] The term “aromatic compound” is intended to mean an organic compound containing at least one unsaturated cyclic group having 4n + 2 delocalized π electrons.

[0051] 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 can be joined 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.

[0052] The term “alkylaryl” is intended to mean an aryl having one or more alkyl substituents.

[0053] The term “aryloxy” is intended to mean the group RO—, where R is aryl.

[0054] When referring to a layer, material, member, or structure, the term "charge transport" is intended to mean that such layer, material, member, or structure facilitates the migration of such charge through the thickness of such layer, material, member, or structure with relatively high efficiency and low charge loss. A hole transport material facilitates positive charge; an electron transport material facilitates negative charge. Although a luminescent material may also have some charge transport properties, the term "charge transport layer, material, member, or structure" is not intended to include a layer, material, member, or structure whose primary function is luminescence.

[0055] 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.

[0056] 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.

[0057] The term "dopant" is intended to mean a material within a layer that includes a host material and that changes one or more electronic properties or one or more target wavelengths of radiation emission, reception, or filtration of such layer as compared to one or more electronic properties or one or more wavelengths of radiation emission, reception, or filtration of such material in the absence of such dopant.

[0058] The abbreviation "FWHM" stands for "full width at half maximum" and is intended to mean the width of the emission profile at half the maximum intensity.

[0059] The term "germyl" refers to the group R3Ge—, where R is the same or different in each occurrence and is H, D, C1-20 alkyl, deuterated alkyl, fluoroalkyl, aryl, or deuterated aryl.

[0060] The prefix "hetero" indicates that one or more carbon atoms have been replaced by a different atom. In some embodiments, the different atom is N, O, or S.

[0061] 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 incorporated. The host material may or may not have one or more electronic properties or capabilities of emitting, receiving, or filtering radiation.

[0062] The terms "luminescent material", "emissive material", and "emitter" are intended to mean a material that emits 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 a wavelength in the range of about 445 - 490 nm.

[0063] 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 subpixel. 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, spraying, and continuous nozzle coating or printing. Discontinuous deposition techniques include, but are not limited to, inkjet printing, gravure printing, and screen printing.

[0064] The term "N - heterocycle" or "N - heteroaryl" refers to a heteroaromatic compound or group having at least one nitrogen in an aromatic ring.

[0065] 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.

[0066] 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.

[0067] The term "photoactive" refers to a material or layer that emits light when activated by an applied voltage (such as in a light - emitting diode or a chemical cell) or generates a signal in response to radiant energy, with or without an applied bias voltage (such as in a photodetector or a photovoltaic cell). The photoactive material or layer is sometimes referred to as an emissive layer. The photoactive layer is abbreviated as "EML" herein.

[0068] The term "siloxane" refers to the group R3SiO(R2Si)-, 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.

[0069] The term "silyloxy" refers to the group R3SiO-, 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.

[0070] The term "silyl" refers to the group R3Si-, where R is the same or different in each occurrence 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.

[0071] All groups may be unsubstituted or substituted. Substituents are discussed below. In structures where the substituent bonds through one or more rings as shown below,

[0072]

[0073] this means that the substituent R can be bonded at any available position on one or more rings.

[0074] 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 in each occurrence.

[0075] 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 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 features or elements specifically stated or described are present.

[0076] Furthermore, "a / an" is 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 construed to include one or at least one, and the singular form also includes the plural form, unless it is obvious that it means otherwise.

[0077] Group numbers corresponding to columns within the Periodic Table are used using the "New Notation" convention as seen in the CRC Handbook of Chemistry and Physics, 81st Edition (2000 - 2001).

[0078] 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 belongs. 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 not intended to be limiting.

[0079] As for the ranges not described herein, many details regarding specific materials, processing behaviors, 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.

[0080] 2. Compounds containing nuclei A to C

[0081] In some embodiments, the polycyclic aromatic compounds described herein include a nuclear structure nucleus A

[0082]

[0083] Wherein:

[0084] Q 1 Is selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ; And

[0085] R 12 -R 14 Are the same or different and are selected from the group consisting of alkyl, carbocyclic aryl, heteroaryl, and their substituted derivatives.

[0086] In some embodiments of nucleus A, Q 1 Is a single bond. This means that there are no additional atoms and the nucleus has the following structure:

[0087]

[0088] In some embodiments of nucleus A, Q 1 Is O.

[0089] In some embodiments of nucleus A, Q 1 Is S.

[0090] In some embodiments of nucleus A, Q 1 Is NR 12 .

[0091] In some embodiments of nucleus A, Q 1is BR 12 .

[0092] In some embodiments of nucleus A, Q 1 is CR 13 R 14 .

[0093] In some embodiments of nucleus A, Q 1 is SiR 13 R 14 .

[0094] In some embodiments of nucleus A, R 12 is an alkyl having 1 - 12 carbons or a deuterated analogue thereof; in some embodiments, it is an alkyl having 1 - 6 carbons or a deuterated analogue thereof.

[0095] In some embodiments of nucleus A, R 12 is an unsubstituted carbocyclic aryl.

[0096] In some embodiments of nucleus A, R 12 is a carbocyclic aryl having 6 - 30 ring carbons or a deuterated analogue thereof; in some embodiments, it is a carbocyclic aryl having 6 - 18 ring carbons or a deuterated analogue thereof.

[0097] In some embodiments of nucleus A, R 12 is a substituted carbocyclic aryl, wherein the substituent is selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl.

[0098] In some embodiments of nucleus A, R 12 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1 - naphthyl, 2 - naphthyl, anthracenyl, fluorenyl, phenanthryl, their deuterated analogues, and their derivatives, which have one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, carbocyclic aryl, heteroaryl, deuterated alkyl, deuterated silyl, deuterated germanium alkyl, deuterated carbocyclic aryl, and deuterated heteroaryl.

[0099] In some embodiments of nucleus A, R 12 is selected from the group consisting of: phenyl, biphenyl, terphenyl, 1 - naphthyl, 2 - naphthyl, anthracenyl, fluorenyl, phenanthryl, their deuterated analogues, and their derivatives, which have one or more substituents selected from the group consisting of: D, alkyl, silyl, germanium alkyl, deuterated alkyl, deuterated silyl, and deuterated germanium alkyl.

[0100] In some embodiments of nucleus A, R 12 is selected from the group consisting of: phenyl, biphenyl, naphthyl, and their substituted derivatives.

[0101] In some embodiments of nucleus A, R 12 is an unsubstituted heteroaryl.

[0102] In some embodiments of nucleus A, R 12 is a heteroaryl having 3 to 30 ring carbons or a deuterated analogue thereof; in some embodiments, is a carbocyclic aryl having 3 to 18 ring carbons or a deuterated analogue thereof.

[0103] In some embodiments of nucleus A, R 12 is a substituted heteroaryl, wherein the substituent is selected from the group consisting of: D, alkyl, silyl, germyl, deuterated alkyl, deuterated silyl, and deuterated germyl.

[0104] In some embodiments of nucleus A, R 12 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 N, O, and S.

[0105] In some embodiments of nucleus A, R 12 is an N - heteroaryl or a deuterated N - heteroaryl having at least one ring atom that is N.

[0106] In some embodiments of nucleus A, R 12 is an O - heteroaryl having at least one ring atom that is O.

[0107] In some embodiments of nucleus A, R 12 is present and is an S - heteroaryl having at least one ring atom that is S.

[0108] In some embodiments of nucleus A, R 12 is an N,O - heteroaryl having at least one ring atom that is N and at least one ring atom that is O.

[0109] For all of the above embodiments of R in nucleus A 12 the same applies to R in nucleus A 13 and R 14 .

[0110] In some embodiments, the polycyclic aromatic compounds described herein comprise a nuclear structure nucleus B,

[0111]

[0112] wherein:

[0113] Q 2 is selected from the group consisting of: a single bond, O, S, NR 12 、BR 12 、CR 13 R 14, and SiR 13 R 14 ; and

[0114] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and their substituted derivatives.

[0115] For all of the above embodiments of Q in nucleus A 1 the same applies to Q in nucleus B 2 .

[0116] For all of the above embodiments of R in nucleus A 12 -R 14 the same applies to R in nucleus B 12 -R 14 .

[0117] In some embodiments, the polycyclic aromatic compounds described herein comprise a nuclear structure, nucleus C,

[0118]

[0119] wherein:

[0120] Q 1 and Q 2 are the same or different and are selected from the group consisting of: single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ; and

[0121] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and their substituted derivatives.

[0122] In some embodiments of nucleus C, Q 1 = Q 2 .

[0123] In some embodiments of nucleus C, Q 1 ≠ Q 2 .

[0124] For all of the above embodiments of Q in nucleus A 1 the same applies to Q in nucleus C 1 and Q 2 .

[0125] For all of the above embodiments of R in nucleus A 12 -R 14All of the above embodiments are equally applicable to R in nucleus C 12 -R 14 。

[0126] 3. Compounds having formulae I to VI

[0127] a. Formula I

[0128] In some embodiments, the compounds described herein have Formula I

[0129]

[0130] Wherein:

[0131] Q 1 is selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0132] R 1 -R 4 is the same or different each time it appears and is selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium alkyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium alkyl, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered alicyclic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0133] R 12 -R 14 is the same or different and is selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0134] a and b are the same or different and are integers from 0 to 3; and

[0135] c and d are the same or different and are integers from 0 to 2.

[0136] For Q in nucleus A 1 All of the above embodiments are equally applicable to Q in Formula I 1 。

[0137] In some embodiments of Formula I, a = 0.

[0138] In some embodiments of Formula I, a = 1.

[0139] In some embodiments of Formula I, a = 2.

[0140] In some embodiments of Formula I, a = 3.

[0141] In some embodiments of Formula I, a > 0.

[0142] In some embodiments of Formula I, a > 0, and at least one R 1 = D.

[0143] In some embodiments of Formula I, a > 0, and at least one R 1 is C 1-20 alkyl or deuterated alkyl; in some embodiments, is C 1-8 alkyl or deuterated alkyl.

[0144] In some embodiments of Formula I, a > 0, and at least one R 1 is C 1-20 alkoxy or deuterated alkoxy; in some embodiments, is C 1-8 alkoxy or deuterated alkoxy.

[0145] In some embodiments of Formula I, a > 0, and at least one R 1 is C 1-20 fluoroalkyl or deuterated fluoroalkyl; in some embodiments, is C 1-8 fluoroalkyl or deuterated fluoroalkyl.

[0146] In some embodiments of Formula I, a > 0, and at least one R 1 is unsubstituted C 6-24 carbocyclic aryl; in some embodiments, is C 6-18 carbocyclic aryl.

[0147] In some embodiments of Formula I, a > 0, and at least one R 1 is a carbocyclic aryl having 6 - 24 ring carbons and having at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0148] In some embodiments of Formula I, a > 0, and at least one R 1 is unsubstituted C 3-24 heteroaryl; in some embodiments, is C 3-18 heteroaryl.

[0149] In some embodiments of Formula I, a > 0, and at least one R 1is a heteroaryl having 6-24 ring carbons and having at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0150] In some embodiments of Formula I, a > 0, and at least one R 1 is a diarylamino or deuterated diarylamino having 12-40 ring carbons; in some embodiments, is a diarylamino or deuterated diarylamino having 12-24 ring carbons.

[0151] In some embodiments of Formula I, b = 0.

[0152] In some embodiments of Formula I, b = 1.

[0153] In some embodiments of Formula I, b = 2.

[0154] In some embodiments of Formula I, b = 3.

[0155] In some embodiments of Formula I, b > 0.

[0156] In some embodiments of Formula I, b > 0, and for R 1 all of the above embodiments for 2 .

[0157] In some embodiments of Formula I, c = 0.

[0158] In some embodiments of Formula I, c = 1.

[0159] In some embodiments of Formula I, c = 2.

[0160] In some embodiments of Formula I, c > 0.

[0161] In some embodiments of Formula I, c > 0, and for R 1 all of the above embodiments for 3 .

[0162] In some embodiments of Formula I, d = 0.

[0163] In some embodiments of Formula I, d = 1.

[0164] In some embodiments of Formula I, d = 2.

[0165] In some embodiments of Formula I, d > 0.

[0166] In some embodiments of Formula I, d > 0, and for R 1 all of the above embodiments for 4 .

[0167] For R in nucleus A 12 、R 13 and R 14 All of the above embodiments for R 12 、R 13 and R 14 also apply to R

[0168] In some embodiments of Formula I, a ≥ 2, and two R 1 are joined together to form a fused 5-membered alicyclic ring.

[0169] In some embodiments of Formula I, a ≥ 2, and two R 1 are joined together to form a fused 6-membered alicyclic ring.

[0170] In some embodiments, the fused alicyclic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0171] In some embodiments of Formula I, a ≥ 2, and two R 1 are joined together to form a fused 5-membered aromatic carbocyclic ring.

[0172] In some embodiments of Formula I, a ≥ 2, and two R 1 are joined together to form a fused 6-membered aromatic carbocyclic ring.

[0173] In some embodiments, the fused aromatic carbocyclic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0174] In some embodiments of Formula I, a ≥ 2, and two R 1 are joined together to form a fused 5-membered heteroaromatic ring.

[0175] In some embodiments of Formula I, a ≥ 2, and two R 1 are joined together to form a fused 6-membered heteroaromatic ring.

[0176] In some embodiments, the fused heteroaromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0177] In some embodiments of Formula I, b ≥ 2, and two R 2 are joined together to form a fused 5-membered alicyclic ring.

[0178] In some embodiments of Formula I, b≥2, and two Rs 2 are joined together to form a fused 6-membered alicyclic ring.

[0179] In some embodiments, the fused alicyclic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0180] In some embodiments of Formula I, b≥2, and two Rs 2 are joined together to form a fused 5-membered aromatic carbocyclic ring.

[0181] In some embodiments of Formula I, b≥2, and two Rs 2 are joined together to form a fused 6-membered aromatic carbocyclic ring.

[0182] In some embodiments, the fused aromatic carbocyclic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0183] In some embodiments of Formula I, b≥2, and two Rs 2 are joined together to form a fused 5-membered heteroaromatic ring.

[0184] In some embodiments of Formula I, b≥2, and two Rs 2 are joined together to form a fused 6-membered heteroaromatic ring.

[0185] In some embodiments, the fused heteroaromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0186] In some embodiments of Formula I, c≥2, and two Rs 3 are joined together to form a fused 5-membered alicyclic ring.

[0187] In some embodiments of Formula I, c≥2, and two Rs 3 are joined together to form a fused 6-membered alicyclic ring.

[0188] In some embodiments, the fused alicyclic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0189] In some embodiments of Formula I, c≥2, and two Rs 3 are joined together to form a fused 5-membered aromatic carbocyclic ring.

[0190] In some embodiments of Formula I, c ≥ 2, and two Rs 3 are joined together to form a fused 6-membered aromatic carbocycle.

[0191] In some embodiments, the fused aromatic carbocycle is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0192] In some embodiments of Formula I, c ≥ 2, and two Rs 3 are joined together to form a fused 5-membered heteroaromatic ring.

[0193] In some embodiments of Formula I, c ≥ 2, and two Rs 3 are joined together to form a fused 6-membered heteroaromatic ring.

[0194] In some embodiments, the fused heteroaromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0195] In some embodiments of Formula I, d ≥ 2, and two Rs 4 are joined together to form a fused 5-membered cycloaliphatic ring.

[0196] In some embodiments of Formula I, d ≥ 2, and two Rs 4 are joined together to form a fused 6-membered cycloaliphatic ring.

[0197] In some embodiments, the fused cycloaliphatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0198] In some embodiments of Formula I, d ≥ 2, and two Rs 4 are joined together to form a fused 5-membered aromatic carbocycle.

[0199] In some embodiments of Formula I, d ≥ 2, and two Rs 4 are joined together to form a fused 6-membered aromatic carbocycle.

[0200] In some embodiments, the fused aromatic carbocycle is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0201] In some embodiments of Formula I, d ≥ 2, and two Rs 4 are joined together to form a fused 5-membered heteroaromatic ring.

[0202] In some embodiments of Formula I, d ≥ 2, and two Rs 4 are joined together to form a fused 6-membered heteroaromatic ring.

[0203] In some embodiments, the fused heteroaromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0204] In some embodiments of Formula I, a > 0, c > 0, and one R 1 and one R 3 are joined together to form a fused 5- or 6-membered cycloaliphatic ring.

[0205] In some embodiments of Formula I, a > 0, c > 0, and one R 1 and one R 3 are joined together to form a fused 5- or 6-membered aromatic carbocyclic ring.

[0206] In some embodiments of Formula I, a > 0, c > 0, and one R 1 and one R 3 are joined together to form a fused 5- or 6-membered heteroaromatic ring.

[0207] In some embodiments, the fused cycloaliphatic ring, aromatic carbocyclic ring, or heteroaromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0208] In some embodiments of Formula I, c > 0, d > 0, and one R 3 and one R 4 are joined together to form a fused 5- or 6-membered cycloaliphatic ring.

[0209] In some embodiments of Formula I, c > 0, d > 0, and one R 3 and one R 4 are joined together to form a fused 5- or 6-membered aromatic carbocyclic ring.

[0210] In some embodiments of Formula I, c > 0, d > 0, and one R 3 and one R 4 are joined together to form a fused 5- or 6-membered heteroaromatic ring.

[0211] In some embodiments, the fused cycloaliphatic ring, aromatic carbocyclic ring, or heteroaromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0212] In some embodiments of Formula I, b > 0, d > 0, and one R 2 and one R 4 are linked together to form a fused 5- or 6-membered cycloaliphatic ring.

[0213] In some embodiments of Formula I, b > 0, d > 0, and one R 2 and one R 4 are linked together to form a fused 5- or 6-membered aromatic carbocyclic ring.

[0214] In some embodiments of Formula I, b > 0, d > 0, and one R 2 and one R 4 are linked together to form a fused 5- or 6-membered heteroaromatic ring.

[0215] In some embodiments, the fused cycloaliphatic ring, aromatic carbocyclic ring or heteroaromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0216] In some embodiments of Formula I, a > 0, and one R 1 is linked to a substituent on Q 1 to form an optionally substituted 5- or 6-membered cycloaliphatic ring, aromatic carbocyclic ring or heteroaromatic ring.

[0217] In some embodiments of Formula I, b > 0, and one R 2 is linked to a substituent on Q 1 to form an optionally substituted 5- or 6-membered cycloaliphatic ring, aromatic carbocyclic ring or heteroaromatic ring.

[0218] In some embodiments of Formula I, there is no amino substituent.

[0219] In some embodiments of Formula I, there is no carbazolyl substituent.

[0220] In some embodiments of Formula I, there is no N-containing organic substituent.

[0221] Any of the above embodiments of Formula I can be combined with one or more of the other embodiments, provided they are not mutually exclusive. For example, an embodiment in which Q 1 is O can be combined with an embodiment in which a = 1 and R 1 is an unsubstituted carbocyclic aryl, and with an embodiment in which c > 0, d > 0 and one R 3 and one R 4Embodiments that combine to form a fused 5- or 6-membered aromatic ring are combined. The same is true for the other non-mutually exclusive embodiments discussed above. Those skilled in the art will understand which embodiments are mutually exclusive and will thus be able to readily determine the combinations of embodiments contemplated by this application.

[0222] Compounds having Formula I can be prepared using any technique that will generate a C-C, C-N, C-B, or B-N bond. A variety of such techniques are known, such as Suzuki, Yamamoto, Stille, Negishi, and metal-catalyzed C-N coupling, as well as metal-catalyzed and oxidative direct arylation, and electrophilic or nucleophilic substitution.

[0223] Deuterated compounds can be prepared in a similar manner using deuterated precursor materials or more commonly by treating the undeuterated compound with a deuterated solvent (such as benzene-d6) in the presence of a Brønsted acid or Lewis acid H / D exchange catalyst (such as trifluoromethanesulfonic acid, aluminum trichloride, or diethylaluminum dichloride). Deuteration reactions have also been described in published PCT application WO 2011 / 053334.

[0224] Exemplary preparations are given in the examples.

[0225] Examples of compounds having Formula I include, but are not limited to, the compounds shown below.

[0226]

[0227] Compound I-7

[0228]

[0229] b. Formula II

[0230] In some embodiments, the compounds described herein have Formula II,

[0231]

[0232] wherein:

[0233] Q 2 is selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0234] R 1 -R 4is the same or different at each occurrence and is selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium alkyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium alkyl, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered alicyclic ring, aromatic carbocyclic ring, heteroaromatic ring, or a substituted derivative thereof;

[0235] R 12 -R 14 is the same or different and is selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0236] a and b are the same or different and are integers from 0 to 3; and

[0237] c and d are the same or different and are integers from 0 to 2.

[0238] For Q in nucleus A 1 All of the above embodiments for 2 .

[0239] For R in formula I 12 -R 14 All of the above embodiments for 12 -R 14 , a, b, c and d also apply to R

[0240] In some embodiments of formula II, there is no amino substituent.

[0241] In some embodiments of formula II, there is no carbazolyl substituent.

[0242] In some embodiments of formula II, there is no N-containing organic substituent.

[0243] Any one of the above embodiments of formula II can be combined with one or more of the other embodiments, provided that they are not mutually exclusive.

[0244] Compounds having formula II can be prepared using any technique that will generate a C-C, C-N, C-B or N-B bond as described above. Deuterated compounds can be prepared as described above.

[0245] Examples of compounds having formula II include, but are not limited to, the compounds shown below.

[0246]

[0247] c. Formula III

[0248] In some embodiments, the compounds described herein have Formula III,

[0249]

[0250] wherein:

[0251] Q 1 and Q 2 are the same or different and are selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0252] R 5 -R 8 is the same or different each time it appears and is selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0253] R 12 -R 14 is the same or different and is selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof; and

[0254] e - h are the same or different and are integers from 0 - 2.

[0255] In some embodiments of Formula III, e = 0.

[0256] In some embodiments of Formula III, e = 1.

[0257] In some embodiments of Formula III, e = 2

[0258] In some embodiments of Formula III, e > 0.

[0259] In some embodiments of Formula III, e > 0, and for R in Formula I 1All of the above embodiments are equally applicable to R in Formula III 5 .

[0260] In some embodiments of Formula III, f = 0.

[0261] In some embodiments of Formula III, f = 1.

[0262] In some embodiments of Formula III, f = 2

[0263] In some embodiments of Formula III, f > 0.

[0264] In some embodiments of Formula III, f > 0, and for R in Formula I 1 All of the above embodiments are equally applicable to R in Formula III 6 .

[0265] In some embodiments of Formula III, g = 0.

[0266] In some embodiments of Formula III, g = 1.

[0267] In some embodiments of Formula III, g = 2.

[0268] In some embodiments of Formula III, g > 0.

[0269] In some embodiments of Formula III, g > 0, and for R in Formula I 1 All of the above embodiments are equally applicable to R in Formula III 7 .

[0270] In some embodiments of Formula III, h = 0.

[0271] In some embodiments of Formula III, h = 1.

[0272] In some embodiments of Formula III, h = 2

[0273] In some embodiments of Formula III, h > 0.

[0274] In some embodiments of Formula III, h > 0, and for R in Formula I 1 All of the above embodiments are equally applicable to R in Formula III 8 .

[0275] For R in nucleus A 12 、R 13 and R 14 All of the above embodiments are equally applicable to R in Formula III 12 、R 13 and R 14 .

[0276] In some embodiments of Formula III, e = 2, and the two Rs 5 are joined together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0277] In some embodiments of Formula III, f = 2, and the two Rs 6 are joined together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0278] In some embodiments of Formula III, g = 2, and the two Rs 7 are joined together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0279] In some embodiments of Formula III, h = 2, and the two Rs 8 are joined together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0280] In some embodiments of Formula III, e > 0, f > 0, and one R 5 and one R 6 are joined together to form a fused 5- or 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0281] In some embodiments of Formula III, f > 0, h > 0, and one R 6 and one R 8 are joined together to form a fused 5- or 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0282] In some embodiments of Formula III, h > 0, g > 0, and one R 7 and one R8 are joined together to form a fused 5- or 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0283] In some embodiments of Formula III, e > 0, g > 0, and one R 5 and one R 7 are joined together to form a fused 5- or 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0284] In some embodiments of Formula III, there is no amino substituent.

[0285] In some embodiments of Formula III, there is no carbazolyl substituent.

[0286] In some embodiments of Formula III, there is no N-containing organic substituent.

[0287] Any of the above embodiments of Formula III can be combined with one or more of the other embodiments, provided they are not mutually exclusive.

[0288] Compounds having Formula III can be prepared using any technique that will produce C-C, C-N, C-B, or N-B bonds as described above. Deuterated compounds can be prepared as described above.

[0289] Examples of compounds having Formula III include, but are not limited to, the compounds shown below.

[0290] Compound III-1

[0291]

[0292] d. Formula IV

[0293] In some embodiments, the compounds described herein have Formula IV,

[0294]

[0295] wherein:

[0296] Q 1 and Q 2 are the same or different and are selected from the group consisting of a single bond, O, S, NR 12 、BR 12 、CR 13 R 14, and SiR 13 R 14 ;

[0297] R 1 、R 2 、R 7 and R 8 are the same or different each time they appear and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium alkyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium alkyl, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered alicyclic ring, aromatic carbocyclic ring, heteroaromatic ring, or a substituted derivative thereof;

[0298] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof; and

[0299] a, a1, b, and b1 are the same or different and are integers from 0 to 3.

[0300] For all of the above embodiments of Q in nucleus A 1 the same applies to Q in formula IV 1 and Q 2 .

[0301] For all of the above embodiments of a, b, R 1 and R 2 in formula I the same applies to a, b, R 1 and R 2 in formula IV.

[0302] For all of the above embodiments of R 12 、R 13 and R 14 in nucleus A the same applies to R 12 、R 13 and R 14 in formula IV.

[0303] In some embodiments of formula IV, a1 = 0.

[0304] In some embodiments of formula IV, a1 = 1.

[0305] In some embodiments of formula IV, a1 = 2.

[0306] In some embodiments of Formula IV, a1 = 3.

[0307] In some embodiments of Formula IV, a1 > 0.

[0308] In some embodiments of Formula IV, a1 > 0, and for R in Formula I 1 All of the above embodiments also apply to R in Formula II 9 .

[0309] In some embodiments of Formula IV, b1 = 0.

[0310] In some embodiments of Formula IV, b1 = 1.

[0311] In some embodiments of Formula IV, b1 = 2.

[0312] In some embodiments of Formula IV, b1 = 3.

[0313] In some embodiments of Formula IV, b1 > 0.

[0314] In some embodiments of Formula IV, b1 > 0, and for R in Formula I 1 All of the above embodiments also apply to R in Formula IV 10 .

[0315] In some embodiments of Formula IV, a ≥ 2, and two Rs 1 are linked together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0316] In some embodiments of Formula IV, b ≥ 2, and two Rs 2 are linked together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0317] In some embodiments of Formula IV, a1 ≥ 2, and two Rs 9 are linked together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0318] In some embodiments of Formula IV, b1 ≥ 2, and two Rs 10Joined together to form a fused 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0319] In some embodiments of Formula IV, a > 0, a1 > 0, and one R 1 and one R 9 Joined together to form a fused 5- or 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0320] In some embodiments of Formula IV, b > 0, b1 > 0, and one R 2 and one R 10 Joined together to form a fused 5- or 6-membered aromatic ring. In some embodiments, the fused aromatic ring is further substituted with at least one substituent selected from the group consisting of D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0321] In some embodiments of Formula IV, there is no amino substituent.

[0322] In some embodiments of Formula IV, there is no carbazolyl substituent.

[0323] In some embodiments of Formula IV, there is no N-containing organic substituent.

[0324] Any one of the above embodiments of Formula IV can be combined with one or more of the other embodiments, provided that they are not mutually exclusive.

[0325] Compounds having Formula IV can be prepared using any technique that will generate C-C, C-N, C-B, or N-B bonds as described above. Deuterated compounds can be prepared as described above.

[0326] Examples of compounds having Formula IV include, but are not limited to, the compounds shown below.

[0327]

[0328]

[0329]

[0330] Compound IV-11

[0331]

[0332] e. Formula V

[0333] In some embodiments, the compounds described herein have Formula V,

[0334]

[0335] wherein:

[0336] Q 3 -Q 4 are the same or different and are selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0337] Q 5 is selected from the group consisting of: N, B, P(O), CR 13 , and SiR 13 ;

[0338] Q 7 is selected from the group consisting of: no bond, a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0339] R 1 , R 2 , R 9 and R 10 are the same or different each time they appear and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0340] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0341] a, a1 and b are the same or different and are integers from 0 to 3; and

[0342] c and d are the same or different and are integers from 0 to 2.

[0343] For Q in nucleus A 1 All of the above embodiments for 3 Q and Q 4 .

[0344] For R in formula I 1 , R 2 , a, b, c and d, all of the above embodiments are equally applicable to R in formula V 1 , R 2 , a, b, c and d.

[0345] For R in nucleus A 12 , R 13 and R 14 , all of the above embodiments are equally applicable to R in formula V 12 , R 13 and R 14 .

[0346] All of the above embodiments for a1 in formula IV are equally applicable to a1 in formula V.

[0347] In some embodiments of formula V, Q 5 is N.

[0348] In some embodiments of formula V, Q 5 is B.

[0349] In some embodiments of formula V, Q 5 is P(O).

[0350] In some embodiments of formula V, Q 5 is CR 13 .

[0351] In some embodiments of formula V, Q 5 is SiR 13 .

[0352] In some embodiments of formula V, Q 7 is a non-bond. This means that there is no connecting bond and the formula is as follows:

[0353]

[0354] In some embodiments of formula V, Q 7 is a single bond.

[0355] In some embodiments of formula V, Q 7 is O.

[0356] In some embodiments of Formula V, Q 7 is S.

[0357] In some embodiments of Formula V, Q 7 is NR 12 .

[0358] In some embodiments of Formula V, Q 7 is BR 12 .

[0359] In some embodiments of Formula V, Q 7 is CR 13 R 14 .

[0360] In some embodiments of Formula V, Q 7 is SiR 13 R 14 .

[0361] In some embodiments of Formula V, c > 0, and for all of the above embodiments of R in Formula I, the same applies to R in Formula V 1 . 9 .

[0362] In some embodiments of Formula V, d > 0, and for all of the above embodiments of R in Formula I, the same applies to R in Formula V 1 . 10 .

[0363] In some embodiments of Formula V, a1 > 0, and for all of the above embodiments of R in Formula I, the same applies to R in Formula V 1 . 11 .

[0364] Any one of the above embodiments of Formula V can be combined with one or more of the other embodiments, provided they are not mutually exclusive.

[0365] Compounds having Formula V can be prepared using any technique that will generate C-C, C-N, C-B, or N-B bonds as described above. Deuterated compounds can be prepared as described above.

[0366] Examples of compounds having Formula V include, but are not limited to, the compounds shown below.

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373] f. Formula VI

[0374] In some embodiments, the compounds described herein have Formula VI,

[0375]

[0376] wherein:

[0377] Q 3 and Q 4 are the same or different and are selected from the group consisting of: single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0378] Q 6 is selected from the group consisting of: N, B, P(O), CR 13 , and SiR 13 ;

[0379] Q 8 is selected from the group consisting of: no bond, single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ;

[0380] R 1 、R 2 、R 9 and R 10 are the same or different each time they appear and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium, where adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, aromatic carbocyclic ring, heteroaromatic ring, or substituted derivative thereof;

[0381] R 12 -R 14are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0382] a, a1 and b are the same or different and are integers from 0 - 3; and

[0383] c and d are the same or different and are integers from 0 - 2.

[0384] For Q in Formula V 5 all of the above embodiments are equally applicable to Q in Formula VI 6 .

[0385] For Q in Formula V 7 all of the above embodiments are equally applicable to Q in Formula VI 8 .

[0386] For R in Formula V 1 , R 2 , R 9 and R 10 , a, a1, b, c and d all of the above embodiments are equally applicable to R in Formula VI 1 , R 2 , R 9 and R 10 , a, a1, b, c and d.

[0387] For R in nucleus A 12 , R 13 and R 14 all of the above embodiments are equally applicable to R in Formula VI 12 , R 13 and R 14 .

[0388] Any one of the above embodiments of Formula VI can be combined with one or more of the other embodiments, provided that they are not mutually exclusive.

[0389] Compounds having Formula VI can be prepared using any technique that will produce C - C, C - N, C - B or N - B bonds as described above. Deuterated compounds can be prepared as described above.

[0390] Examples of compounds having Formula VI include, but are not limited to, the compounds shown below.

[0391]

[0392]

[0393] 4. Compounds having formulae VII to XI

[0394] In some embodiments, the polycyclic aromatic compound contains two boron-nitrogen bonds.

[0395] In some embodiments, the polycyclic aromatic compounds described herein have Formula VII,

[0396]

[0397] wherein:

[0398] Q 1 、Q 2 、Q 9 and Q 10 are the same or different and are selected from the group consisting of: a single bond, O, S, NR 12 、BR 12 、CR 13 R 14 、and SiR 13 R 14 ; and

[0399] R 1 、R 2 、R 9 and R 10 are the same or different in each occurrence and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered alicyclic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0400] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0401] R 15 and R 16is the same or different at each occurrence and is selected from the group consisting of: H, D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof; and

[0402] a, a1, b, and b1 are the same or different and are integers from 0 to 3.

[0403] For Q in nucleus A 1 all of the above embodiments for the same apply to Q in formula VII 1 、Q 2 、Q 9 and Q 10 .

[0404] For R in formula I 1 all of the above embodiments for the same apply to R in formula VII 1 、R 2 、R 9 and R 10 .

[0405] For R in nucleus A 12 -R 14 all of the above embodiments for the same apply to R in formula VII 12 -R 14 .

[0406] All of the above embodiments for a, a1, b, and b1 in formula IV apply to a, a1, b, and b1 in formula VII.

[0407] In some embodiments of formula VII, R 15 = H.

[0408] In some embodiments of formula VII, R 15 = D.

[0409] In some embodiments of formula VII, R 15 is C 1-20 alkyl or deuterated alkyl; in some embodiments, it is C 1-8 alkyl or deuterated alkyl.

[0410] In some embodiments of formula VII, R 15 is C 1-20an alkoxy or deuterated alkoxy group; in some embodiments, it is C 1-8 an alkoxy or deuterated alkoxy group.

[0411] In some embodiments of Formula VII, R 15 is C 1-20 a fluoroalkyl or deuterated fluoroalkyl group; in some embodiments, it is C 1-8 a fluoroalkyl or deuterated fluoroalkyl group.

[0412] In some embodiments of Formula VII, R 15 is an unsubstituted C 6-24 carbocyclic aryl group; in some embodiments, it is C 6-18 a carbocyclic aryl group.

[0413] In some embodiments of Formula VII, R 15 is a carbocyclic aryl group having 6 - 24 ring carbons and having at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0414] In some embodiments of Formula VII, R 15 is an unsubstituted C 3-24 heteroaryl group; in some embodiments, it is C 3-18 a heteroaryl group.

[0415] In some embodiments of Formula VII, R 15 is a heteroaryl group having 6 - 24 ring carbons and having at least one substituent selected from the group consisting of: D, alkyl, silyl, deuterated alkyl, deuterated silyl, and combinations thereof.

[0416] In some embodiments of Formula VII, R 15 is a diarylamino or deuterated diarylamino group having 12 - 40 ring carbons; in some embodiments, it is a diarylamino or deuterated diarylamino group having 12 - 24 ring carbons.

[0417] For all of the above embodiments of R 15 in Formula VII, the same applies to R 15 in Formula VII.

[0418] Any one of the above embodiments of Formula VII can be combined with one or more of the other embodiments, provided they are not mutually exclusive.

[0419] Compounds having Formula VII can be prepared using any technique that will generate a C - C, C - N, C - B, or N - B bond as described above. Deuterated compounds can be prepared as described above.

[0420] In some embodiments, the polycyclic aromatic compounds described herein have Formula VIII,

[0421]

[0422] wherein:

[0423] Q 1 、Q 2 、Q 9 and Q 10 are the same or different and are selected from the group consisting of: a single bond, O, S, NR 12 、BR 12 、CR 13 R 14 、and SiR 13 R 14 ; and

[0424] R 1 、R 2 、R 6 、R 7 、R 9 and R 10 are the same or different each time they appear and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium alkyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium alkyl, where adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered alicyclic ring, aromatic carbocyclic ring, heteroaromatic ring, or a substituted derivative thereof;

[0425] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0426] R 15 and R 16are the same or different at each occurrence and are selected from the group consisting of: H, D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germyl, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0427] a, a1, b and b1 are the same or different and are integers from 0 to 3; and

[0428] c and d are the same or different and are integers from 0 to 2.

[0429] For Q in nucleus A 1 all of the above embodiments are equally applicable to Q in formula VIII 1 , Q 2 , Q 9 and Q 10 .

[0430] For R in formula I 1 all of the above embodiments are equally applicable to R in formula VIII 1 , R 2 , R 9 and R 10 .

[0431] For R in nucleus A 12 -R 14 all of the above embodiments are equally applicable to R in formula VIII 12 -R 14 .

[0432] All of the above embodiments for a, a1, b and b1 in formula IV are equally applicable to a, a1, b and b1 in formula VIII.

[0433] For R in formula VII 15 all of the above embodiments are equally applicable to R in formula VIII 15 and R 16 .

[0434] Any of the above embodiments of formula VIII may be combined with one or more of the other embodiments, provided that they are not mutually exclusive.

[0435] Compounds having Formula VIII can be prepared using any technique that will form a C-C, C-N, C-B, or N-B bond as described above. Deuterated compounds can be prepared as described above.

[0436] In some embodiments, the polycyclic aromatic compounds described herein have Formula IX,

[0437]

[0438] wherein:

[0439] Q 1 and Q 2 are the same or different and are selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ; and

[0440] R 1 , R 2 , R 6 , R 7 , R 9 , and R 10 are the same or different each time they appear and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germyl, where adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, aromatic carbocyclic ring, heteroaromatic ring, or a substituted derivative thereof;

[0441] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0442] a, a1, b, and b1 are the same or different and are integers from 0-3; and

[0443] c and d are the same or different and are integers from 0-2.

[0444] All of the above embodiments for Q in nucleus A 1 apply equally to Q in Formula IX 1 and Q 2 .

[0445] For R in formula I 1 All of the above embodiments for [it] also apply to R in formula IX 1 、R 2 、R 6 、R 7 、R 9 and R 10 。

[0446] For R in nucleus A 12 -R 14 All of the above embodiments for [it] also apply to R in formula IX 12 -R 14 。

[0447] All of the above embodiments for a, a1, b and b1 in formula IV also apply to a, a1, b and b1 in formula IX.

[0448] All of the above embodiments for c and d in formula I also apply to c and d in formula IX.

[0449] Any one of the above embodiments of formula IX can be combined with one or more of the other embodiments, as long as they are not mutually exclusive.

[0450] Compounds having formula IX can be prepared using any technique that will produce C-C, C-N, C-B or N-B bonds as described above. Deuterated compounds can be prepared as described above.

[0451] In some embodiments, the polycyclic aromatic compounds described herein have formula X

[0452]

[0453] wherein:

[0454] Q 1 and Q 9 are the same or different and are selected from the group consisting of: single bond, O, S, NR 12 、BR 12 、CR 13 R 14 、and SiR 13 R 14 ;and

[0455] R 1 、R 2 、R 6 、R 7 、R 9 and R 10Are the same or different at each occurrence and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germyl, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germyl, wherein adjacent R groups or R groups on adjacent rings may be joined together to form a 5- or 6-membered cycloaliphatic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0456] R 12 -R 14 Are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0457] a, a1, b, and b1 are the same or different and are integers from 0 to 3; and

[0458] c and d are the same or different and are integers from 0 to 2.

[0459] For Q in nucleus A 1 All of the above embodiments for the same apply to Q in formula X 1 and Q 9 .

[0460] For R in formula I 1 All of the above embodiments for the same apply to R in formula X 1 、R 2 、R 6 、R 7 、R 9 and R 10 .

[0461] For R in nucleus A 12 -R 14 All of the above embodiments for the same apply to R in formula X 12 -R 14 .

[0462] All of the above embodiments for a, a1, b, and b1 in formula IV apply to a, a1, b, and b1 in formula X.

[0463] All of the above embodiments for c and d in formula I apply to c and d in formula X.

[0464] Any one of the above embodiments of formula X may be combined with one or more of the other embodiments, provided they are not mutually exclusive.

[0465] Compounds having formula X can be prepared using any technique that will form a C-C, C-N, C-B, or N-B bond as described above. Deuterated compounds can be prepared as described above.

[0466] In some embodiments, the polycyclic aromatic compounds described herein have formula XI,

[0467]

[0468] wherein:

[0469] Q 2 and Q 10 are the same or different and are selected from the group consisting of: a single bond, O, S, NR 12 , BR 12 , CR 13 R 14 , and SiR 13 R 14 ; and

[0470] R 1 , R 2 , R 6 , R 7 , R 9 , and R 10 are the same or different each time they appear and are selected from the group consisting of: D, F, CN, alkyl, alkoxy, fluoroalkyl, carbocyclic aryl, aryloxy, heteroaryl, diarylamino, silyl, siloxane, silyloxy, germanium, deuterated alkyl, deuterated partially fluorinated alkyl, deuterated alkoxy, deuterated carbocyclic aryl, deuterated aryloxy, deuterated heteroaryl, deuterated diarylamino, deuterated silyl, deuterated siloxane, deuterated silyloxy, and deuterated germanium, where adjacent R groups or R groups on adjacent rings can be joined together to form a 5- or 6-membered cycloaliphatic ring, an aromatic carbocyclic ring, a heteroaromatic ring, or a substituted derivative thereof;

[0471] R 12 -R 14 are the same or different and are selected from the group consisting of: alkyl, carbocyclic aryl, heteroaryl, and substituted derivatives thereof;

[0472] a, a1, b, and b1 are the same or different and are integers from 0-3; and

[0473] c and d are the same or different and are integers from 0-2.

[0474] All of the above embodiments for Q in nucleus A 1 apply equally to Q in formula XI 2 and Q 10 .

[0475] For R in formula I 1 All of the above embodiments for 1 R 2 R 6 R 7 R 9 and R 10 also apply to R in formula XI.

[0476] For R in nucleus A 12 -R 14 All of the above embodiments for 12 -R 14 also apply to R in formula XI.

[0477] All of the above embodiments for a, a1, b and b1 in formula IV also apply to a, a1, b and b1 in formula XI.

[0478] All of the above embodiments for c and d in formula I also apply to c and d in formula XI.

[0479] Any one of the above embodiments of formula XI can be combined with one or more of the other embodiments, provided they are not mutually exclusive.

[0480] Compounds having formula XI can be prepared using any of the techniques described above that will generate C-C, C-N, C-B or N-B bonds. Deuterated compounds can be prepared as described above.

[0481] Examples of compounds having two B-N bonds include, but are not limited to, the compounds shown below.

[0482]

[0483] Compound IX-1

[0484]

[0485]

[0486] Compound XI-1

[0487]

[0488] 5. Device

[0489] Organic electronic devices that can benefit from having one or more layers containing the compounds 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 methods (e.g., photodetectors, photoconductive cells, photoresistors, light-activated relays, 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 that include 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 (1) through (5).

[0490] In some embodiments, the device includes a photoactive layer having the compounds described herein.

[0491] In some embodiments, the device includes an anode and a cathode and a photoactive layer therebetween, wherein the photoactive layer contains the compounds described in the text.

[0492] 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) 160, and a photoactive layer (“EML”) 140 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 that contains a hole transport material. Adjacent to the cathode may be an electron transport layer (“ETL”) 150 that contains an electron transport material. Optionally, the device may use one or more additional hole injection layers or hole transport layers (not shown) adjacent to the anode 110 and / or one or more additional electron injection layers (“EIL”) or electron transport layers (not shown) adjacent to the cathode 160. As a further option, the device may have a quenching-resistant layer (not shown) between the photoactive layer 140 and the electron transport layer 150.

[0493] Layers 120 to 150, and any additional layers therebetween, are individually and collectively referred to as the active layers.

[0494] In some embodiments, the photoactive layer is pixelated, as in Figure 2As shown. In device 200, layer 140 is divided into pixel or sub-pixel units 141, 142, and 143 that repeat on the layer. Each of the pixel or sub-pixel units represents a different color. In some embodiments, these sub-pixel units are red, green, and blue. Although three sub-pixel units are shown in the figure, two or more than three sub-pixel units can be used.

[0495] In some embodiments, the different layers have the following thickness ranges: anode 110, 50 - 500 nm, in some embodiments 100 - 200 nm; hole injection layer 120, 5 - 200 nm, in some embodiments 20 - 100 nm; hole transport layer 130, 5 - 200 nm, in some embodiments 20 - 100 nm; photoactive layer 140, 1 - 200 nm, in some embodiments 10 - 100 nm; electron transport layer 150, 5 - 200 nm, in some embodiments 10 - 100 nm; cathode 160, 20 - 1000 nm, in some embodiments 30 - 500 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.

[0496] In some embodiments, the compounds described herein can be used as blue light-emitting materials in photoactive layer 140. They can be used alone or as dopants in host materials.

[0497] In some embodiments, the compounds described herein have a photoluminescence emission profile where the FWHM is less than 50 nm; in some embodiments less than 40 nm; in some embodiments less than 30 nm; in some embodiments less than 20 nm. This is advantageous for display devices for producing more saturated colors.

[0498] a. Photoactive layer

[0499] As used herein, the term "one or more compounds described herein" or "compounds described herein" is intended to include compounds containing any of nuclei A through C, and includes compounds having any of formulas I through XI.

[0500] In some embodiments, the photoactive layer comprises a host material and a compound described herein as a dopant. In some embodiments, a second host material is present.

[0501] In some embodiments, the photoactive layer consists only of a host material and a compound described herein as a dopant. In some embodiments, small amounts of other materials are present, provided they do not significantly alter the function of the layer.

[0502] The weight ratio of the total dopant to the total host material ranges from 2:98 to 70:30; in some embodiments, from 5:95 to 70:30; in some embodiments, from 10:90 to 20:80.

[0503] In some embodiments, the second host material is selected from the group consisting of: anthracene, pyrene, phenanthrene, benzophenanthrene, phenanthroline, naphthalene, triazine, quinoline, isoquinoline, quinoxaline, phenylpyridine, benzodifuran, metalquinolinate complexes, indolocarbazole, substituted derivatives thereof, and combinations thereof.

[0504] Any of the compounds described herein, as represented by the examples, specific embodiments, specific instances, and combinations of the embodiments discussed above, can be used in the photoactive layer.

[0505] b. Other device layers

[0506] The other layers in the device can be made of any materials known to be useful in such layers.

[0507] 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, generally mixed metal oxides of Group 12, 13, and 14 metals, such as indium tin oxide, are used. The anode can also be made of an organic material such as polyaniline, as described in "Flexible light-emitting diodes made from soluble conducting polymer", Nature, Vol. 357, pp. 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.

[0508] The hole injection layer 120 includes a hole injection material 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 of a polymeric material, such as polyaniline (PANI) or poly(3,4-ethylenedioxythiophene) (PEDOT), which are typically doped with a protonic acid. The protonic acid can be, for example, poly(styrenesulfonic acid), poly(2-acrylamido-2-methyl-1-propanesulfonic acid), etc.

[0509] The hole injection layer can include charge transfer compounds, such as copper phthalocyanine, 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile (HAT-CN), and tetrathiafulvalene-tetracyanoquinodimethane system (TTF-TCNQ).

[0510] In some embodiments, the hole injection layer includes at least one conductive polymer and at least one fluorinated acid polymer.

[0511] Examples of hole transport 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 transport molecules and polymers can be used. Commonly used hole transport 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 (α-NPB), and porphyrin compounds such as copper phthalocyanine. In some embodiments, the hole transport layer comprises a hole transport polymer. In some embodiments, the hole transport 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 transport polymers are polyvinylcarbazole, (phenylmethyl)-polysilane, and polyaniline. Hole transport polymers can also be obtained by incorporating hole transport 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.

[0512] In some embodiments, the hole transport layer further comprises a p-type dopant. In some embodiments, the hole transport layer is doped with a p-type dopant. Examples of p-type dopants include, but are not limited to, tetrafluoro-tetracyano-p-benzoquinodimethane (F4-TCNQ) and perylene-3,4,9,10-tetracarboxylic-3,4,9,10-dianhydride (PTCDA).

[0513] In some embodiments, there are more than one hole transport layer (not shown).

[0514] Examples of electron transport materials that can be used for layer 150 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(2-methyl-8-hydroxyquinolinato) (HfQ), and zirconium(IV) bis(2-methyl-8-hydroxyquinolinato) (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 Cs2CO3; 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 W2(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.

[0515] 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 the singlet energy 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. In addition, 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. Generally, the quenching-resistant material is a large bandgap material with high singlet and triplet energies.

[0516] The cathode 160 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 used for the cathode can be selected from the alkali metals of Group 1 (e.g., Li, Cs), the Group 2 (alkaline earth) metals, the 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.

[0517] Inorganic compounds containing alkali metals, such as LiF, CsF, Cs2O, and Li2O, or organometallic compounds containing Li can also be deposited between the organic layer 150 and the cathode layer 160 to reduce the operating voltage. This layer (not shown) can be referred to as an electron injection layer.

[0518] It is known that there are other layers in the organic electronic device. For example, a layer (not shown) can 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 to serve as a protective layer. Layers known in the art, such as copper phthalocyanine, silicon oxynitride, fluorocarbon, silane, or ultra-thin layers of metals (such as Pt), can be used. Alternatively, the anode layer 110, the active layers 120, 130, 140, and 150, or some or all of the cathode layer 160 can be surface-treated to increase the 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.

[0519] It should be understood that each functional layer can be composed of more than one layer.

[0520] c. Device fabrication

[0521] The device layers can be formed by any deposition technique or combination of techniques, including vapor deposition, liquid deposition, and thermal transfer.

[0522] In some embodiments, the device is made by liquid deposition of a hole injection layer, a hole transport layer, and a photoactive layer, and vapor deposition of an anode, an electron transport layer, an electron injection layer, and a cathode. Suitable liquid deposition techniques are well known in the art.

[0523] In some embodiments, all of the device layers are made by vapor deposition. Such techniques are well known in the art.

[0524] Examples

[0525] The concepts described herein will be further described in the following examples, which do not limit the scope of the invention as set forth in the claims.

[0526] Synthesis examples

[0527] This example illustrates the preparation of a compound having the formula I as described above.

[0528] Synthesis example 1

[0529] This example shows the synthesis of compound I-1.

[0530]

[0531] 2-Bromo-3'-chloro-1,1'-biphenyl (3).

[0532] A mixture of 3-chlorophenylboronic acid 1 (4.7 g, 30.06 mmol), 1-bromo-2-iodobenzene 2 (8.08 g, 28.56 mmol), Pd(PPh3)4 (1.24 g, 1.073 mmol), and potassium carbonate (9.87 g, 71.41 mmol) in toluene (100 ml), water (20 ml), and ethanol (40 ml) was degassed and stirred under a nitrogen atmosphere for 5 hours while heating at 95 °C. Thereafter, the mixture was cooled, water (100 ml) was added to the mixture, the organic phase was separated, and passed through a silica gel-packed filter eluted with toluene. The residue after vacuum evaporation of toluene was redissolved in dichloromethane, adsorbed on diatomaceous earth, and subjected to chromatography on a silica gel column eluted with hexane. The fractions containing the product were combined, the eluate was evaporated, and the residue was dried in vacuo to obtain 2-bromo-3'-chloro-1,1'-biphenyl 3 (3.46 g) as an oil. 1 1H-NMR (CDCl3, 500 MHz): 7.23 (td, 1H, J1 = 8 Hz, J2 = 2 Hz), 7.29 - 7.32 (m, 2H), 7.35 - 7.39 (m, 3H), 7.40 - 7.41 (m, 1H), 7.68 (dd, J1 = 8 Hz, J2 = 1 Hz).

[0533] 3'-Chloro-[1,1'-biphenyl]-2-amine (5).

[0534] 3-Chlorophenylboronic acid 1 (10.12 g, 64.72 mmol), 2-iodoaniline 4 (14.26 g, 63.95 mmol), Pd(PPh3)4 (3.05 g, 2.64 mmol), and potassium carbonate (22.7 g, 164.24 mmol) in a mixture of toluene (100 ml), water (20 ml), and ethanol (40 ml) were degassed and stirred under a nitrogen atmosphere for 5 h while heating at 95 °C. Thereafter, the mixture was cooled, water (100 ml) was added to the mixture, the organic phase was separated, and passed through a silica gel-packed filter eluted with toluene. The residue after vacuum evaporation of toluene was redissolved in dichloromethane, adsorbed on diatomaceous earth, and subjected to chromatography on a silica gel column using a gradient elution with a mixture of hexane and dichloromethane. The fractions containing the product were combined, the eluate was evaporated, and the residue was dried in vacuo to give 3'-chloro-[1,1'-biphenyl]-2-amine 5 (8.88 g). 1 1H-NMR (CDCl3, 500 MHz): 3.96 (br.s, 2H), 6.79 (dd, 1H, J1 = 8 Hz, J2 = 1 Hz), 6.85 (td, 1H, J1 = 8 Hz, J2 = 1 Hz), 7.11 (dd, 1H, J1 = 8 Hz, J2 = 1 Hz), 7.19 (td, 1H, J1 = 8 Hz, J2 = 2 Hz), 7.32 - 7.40 (m, 3H), 7.47 - 7.48 (m, 1H).

[0535] 3'-Chloro-N-(3'-chloro[1,1'-biphenyl]-2-yl)-[1,1'-biphenyl]-2-amine (6).

[0536] The reaction was carried out in two batches: A mixture of 2-bromo-3'-chloro-1,1'-biphenyl 3 (total 3.5 g), 3'-chloro-[1,1'-biphenyl]-2-amine 5 (total 2.66 g), tri-tert-butylphosphine (total 294 mg), Pd2(dba)3 (total 0.692 g), and sodium tert-butoxide (total 1.55 g) in toluene (125 ml) was heated at 40 °C and stirred under a nitrogen atmosphere for 1 h. The combined reaction mixture was passed through a silica gel-packed filter eluted with dichloromethane. The residue after evaporation of the solvent was redissolved in dichloromethane, adsorbed on diatomaceous earth, and subjected to chromatography on a silica gel column using a gradient elution with a mixture of hexane and dichloromethane. The fractions containing the product were combined, the eluate was evaporated, and the residue was dried in vacuo to give 3-chloro-N-(3'-chloro[1,1'-biphenyl]-2-yl)-[1,1'-biphenyl]-2-amine 6 (3.45 g) as a viscous oil that gradually solidified on standing. 11H-NMR (CDCl3, 500 MHz): 5.55 (br.s, 1H), 6.99 (td, 2H, J1 = 8 Hz, J2 = 1 Hz), 7.10 (dt, 2H, J1 = 8 Hz, J2 = 1 Hz), 7.18 (dd, 2H, J1 = 8 Hz, J2 = 1 Hz), 7.22 - 7.30 (m, 8H), 7.37 (dd, 2H, J1 = 8 Hz, J2 = 1 Hz).

[0537] 10-Phenyl-10H,20H-5,9:11,15-dimethyldibenzo[b,o][1,9]diazacyclohexadecine (7).

[0538] A mixture of 3'-chloro-N-(3'-chloro[1,1'-biphenyl]-2-yl)-[1,1'-biphenyl]-2-amine 6 (0.332 g, 0.851 mmol), aniline (85 mg, 0.91 mmol), SPhos (total 294 mg), Pd2(dba)3 (35 mg, 0.085 mmol), and sodium tert-butoxide (164 mg, 1.7 mmol) in toluene (25 mL) was stirred under a nitrogen atmosphere for 3 hours while heating at 110 °C. The reaction mixture was cooled, the toluene was evaporated in vacuo, the residue was redissolved in dichloromethane, adsorbed onto silica gel, and subjected to chromatography on a silica gel column with gradient elution using a mixture of hexane and dichloromethane. The fractions containing the product were combined, the eluate was evaporated, and the residue was dried in vacuo to give 10-phenyl-10H,20H-5,9:11,15-dimethyldibenzo[b,o][1,9]diazacyclohexadecine 7 (121 mg) as a white solid. 1 1H-NMR (CDCl3, 500 MHz): 6.94 (td, 2H, J1 = 8 Hz, J2 = 1 Hz), 6.98 (d, 2H, J = 8 Hz), 7.10 (t, 1H, J = 8 Hz), 7.16 - 7.25 (m, 6H), 7.33 - 7.43 (m, 10H), 7.58 (br.s, 1H).

[0539] Compound I-1 (8).

[0540] A mixture of compound 7 (121 mg, 0.295 mmol), a 1 M solution of boron tribromide in dichloromethane (1.5 ml, 1.47 mmol) in 1,2 - dichlorobenzene (10 ml) was stirred at 180 °C for 105 minutes under a nitrogen atmosphere. Thereafter, an additional amount of the 1 M solution of boron tribromide in dichloromethane (0.4 ml) was added and the mixture was heated at 180 °C for 2 hours. The reaction mixture was cooled, the solvent was evaporated using a rotary evaporator, the residue was redissolved in dichloromethane, adsorbed onto diatomaceous earth, and subjected to chromatography on a silica gel column with gradient elution using a mixture of hexane and dichloromethane. The fractions containing the product were combined, the eluate was evaporated to a volume of about 7 ml, and the precipitate was collected by filtration to give 40 mg of compound I - 1. The filtrate was further evaporated to give 52 mg of a crude product of low purity. MS: MH+ = 419. 1 1H - NMR (CDCl3, 500 MHz): 6.53 (d, 2H, J = 9 Hz), 7.37 (td, 2H, J1 = 7 Hz, J2 = 2 Hz), 7.42 (d, 2H, J = 7), 7.48 (td, 2H, J1 = 8 Hz, J2 = 2 Hz), 7.58 - 7.63 (m 3H), 7.72 (t, 2H, J = 8 Hz), 7.92 (d, 2H, J = 8 Hz), 8.46 (dd, 2H, J1 = 8 Hz, J2 = 1 Hz), 8.51 (d, 2H, J = 8 Hz). UV - vis (acetonitrile - water) λ max (nm): 402, 384, 362, 260. Photoluminescence (toluene): 404 nm, quantum yield - 76%.

[0541] This example illustrates the preparation of a compound of formula V as described above.

[0542] Synthesis example 2

[0543] This example shows the synthesis of compound V - 4.

[0544]

[0545]

[0546]

[0547] Bis(2 - bromo - 5 - methoxyphenyl)amine (11).

[0548] A mixture of 4-chloro-2-bromoanisole 9 (35.906 g, 162 mmol), 5-chloro-2-methoxyaniline 10 (25.55 g, 162 mmol), tri-tert-butylphosphine (0.731 g, 3.612 mmol), Pd2(dba)3 (1.654 g, 1.806 mmol), sodium tert-butoxide (18.69 g, 194.5 mmol) in toluene (100 ml) was stirred at ambient temperature under nitrogen atmosphere for 16 hours. Thereafter, the mixture was diluted with methanol (150 ml), the precipitate was filtered, washed with methanol, water, methanol, and dried in vacuo to give bis(2-bromo-5-methoxyphenyl)amine 11 (34.3 g). 1 H-NMR (CD2Cl2, 500MHz): 3.86 (s, 6H), 6.53 (br.s, 1H), 6.80-6.85 (m, 4H), 7.25 (d, 2H, J = 2Hz).

[0549] N-tert-Butyloxycarbonyl-bis(2-bromo-5-methoxyphenyl)amine (12).

[0550] A mixture of bis(2-bromo-5-methoxyphenyl)amine 11 (40 g, 134 mmol), BOC2O (100 g), DMAP (about 1 g) in tetrahydrofuran (600 ml) was stirred for 2.5 days under a nitrogen atmosphere while heating at 57° C. Thereafter, additional amounts of DMAP (a total of 0.75 g) and BOC2O (98 g) were added, and the mixture was further heated at 57° C. for another 11 hours with stirring. The reaction mixture was filtered, and the filtrate was evaporated to a volume of about 200 ml and treated with hexane (400 ml). The precipitate was collected by filtration and dried to give N-tert-butoxycarbonyl-bis(2-bromo-5-methoxyphenyl)amine 12 (41.9 g). 1 H-NMR (CD2Cl2, 500MHz): 1.36 (s, 9H), 3.85 (s, 6H), 6.87 (d, 2H, J = 9Hz), 7.14 (br.s, 2H), 7.17 (dd, 2H, J1 = 9Hz, J2 = 3Hz).

[0551] Compound (13).

[0552] A mixture of N-Boc-bis(2-bromo-5-methoxyphenyl)amine 12 (41.9 g, 105.05 mmol), aniline (22.5 g, 242 mmol), SPhos (0.863 g, 2.101 mmol), Pd2(dba)3 (0.947 g, 1.034 mmol), and sodium tert-butoxide (24 g, 250 mmol) in toluene (400 ml) was stirred under a nitrogen atmosphere while heating at 110 °C for 3.5 h. The reaction mixture was cooled, filtered, and the precipitate was washed with toluene, water, methanol, and hexane and dried to give compound 13 (48.3 g). 1 H-NMR (CD2Cl2, 500 MHz): 1.38 (s, 9H), 3.80 (s, 6H), 5.58 (br.s, 2H), 6.79 (t, 2H, J = 7 Hz), 6.86 (d, 6H, J = 9 Hz), 6.97 (d, 2H, J = 9 Hz), 7.04 (d, 2H, J = 3 Hz), 7.16 (t, 4H, J = 8 Hz).

[0553] Compound (14).

[0554] A mixture of compound 13 (48.3 g, 94.4 mmol), 1-bromo-2,3-dichlorobenzene (21.35 g, 94.5 mmol), SPhos (1.29 g, 3.14 mmol), Pd2(dba)3 (1.44 g, 1.57 mmol), and sodium tert-butoxide (22.7 g, 236.2 mmol) in toluene (800 ml) was stirred under a nitrogen atmosphere while heating at 80 °C. After about 2 h, an additional amount of 1-bromo-2,3-dichlorobenzene (4.7 g, 20.81 mmol) was added. The progress was monitored by TLC. After the starting material was almost completely consumed, the reaction mixture was cooled and washed with water. The organic phase was separated, toluene was distilled off using a rotary evaporator, the residue was redissolved in dichloromethane, adsorbed onto silica gel, and subjected to chromatography on a silica column with gradient elution using a mixture of hexane and ethyl acetate. After eluting the double-coupled product, the subsequent fractions containing the second peak of the pure single-coupled product were combined, the eluate was evaporated, and the residue was dried in vacuo to give compound 14 (18 g). 1 H-NMR (CD2Cl2, 500 MHz): 1.34 (s, 9H), 3.61 (s, 3H), 3.78 (s, 3H), 6.76 - 6.91 (m, 7H), 6.97 (br.d, 1H, J = 9 Hz), 7.02 (d, 1H, J = 3 Hz), 7.09 - 7.19 (m, 6H), 7.32 (dd, 1H, J1 = 8 Hz, J2 = 2 Hz).

[0555] N 2-tert-Butoxycarbonyl-20-chloro-8,14-diphenyl-4,18-dimethoxy-2,8,14-triazatricyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9(20),10,12,15(19),16-nonadecaene(15).

[0556] A solution of compound 14 in 100 ml of toluene was added dropwise to a stirred solution of Pd2(dba)3 (56 mg, 0.061 mmol), SPhos (50 mg, 0.123 mmol), and NaOtBu (388 mg, 4.03 mmol) in 100 ml of toluene over a 7-hour period at 110 °C, and the resulting solution was heated at 110 °C for an additional 6 hours. The reaction mixture was passed through a filter packed with silica gel and eluted with toluene, then dichloromethane-hexane 1:1, and finally dichloromethane to elute the product. The eluate was evaporated, and the residue was dried in vacuo to give compound 15 (0.99 g). 1 1H-NMR (CD2Cl2, 500 MHz): 1.44 (s, 9H), 3.75 (s, 3H), 3.77 (s, 3H), 6.54 (d, 1H, J = 3 Hz), 6.62 (d, 1H, J = 3 Hz), 6.68 (d, 1H, J = 9 Hz), 6.72 (d, 1H, J = 9 Hz), 6.94 - 7.03 (m, 6H), 7.15 (t, 1H, J = 8 Hz), 7.28 - 7.30 (m, 8H).

[0557] N 2 -tert-Butoxycarbonyl-20-chloro-8,14-diphenyl-4,18-dihydroxy-2,8,14-triazatricyclo[13.3.1.13,7.19,13]henicosa-1(18),3,5,7(21),9(20),10,12,15(19),16-nonadecaene(16).

[0558] Boron tribromide (12.7 g, 50.64 mmol) was added to a solution of compound 15 (6.04 g, 9.74 mmol) in dichloromethane (100 ml) at ambient temperature under a nitrogen atmosphere, and the resulting mixture was stirred for 3 hours. Thereafter, the mixture was poured into ice, and the organic phase was separated and washed with water (2 times). The crude product 16 after evaporation of the solvent was dried and used for the next step without further purification.

[0559] [20-Chloro-8,14-diphenyl-18-(trifluoromethanesulfonyloxy)-2,8,14-triazatricyclo[13.3.1.13,7.19,13]henicosan-1(18),3,5,7(21),9(20),10,12,15(19),16-nonadecaen-4-yl]trifluoromethanesulfonate (17).

[0560] A mixture of the crude compound 16 (4.79 g, 9.74 mmol), trifluoromethanesulfonic anhydride (7.69 g, 27.27 mmol), and pyridine (3.85 g) in dichloromethane (100 ml) was stirred for 3 hours under a nitrogen atmosphere while cooling with a water / ice bath. Thereafter, the solvent was evaporated using a rotary evaporator, and the residue was redissolved in a mixture of hexane and dichloromethane (2:1) and passed through a short silica gel column eluted with a mixture of hexane and dichloromethane (2:1). The eluate was evaporated, and the residue was dried to obtain the crude compound 17 (1.552 g), which was used for the next step without further purification. MS: MH+ = 756.

[0561] N 2 N-tert-Butoxycarbonyl-20-chloro-8,14-diphenyl-4,18-bis(3-chlorophenyl)-2,8,14-triazatricyclo[13.3.1.13,7.19,13]henicosan-1(18),3,5,7(21),9(20),10,12,15(19),16-nonadecene (18).

[0562] A mixture of 3-chlorophenylboronic acid 1 (0.93 g, 5.95 mmol), the above compound 17 (1.552 g, crude), Pd(PPh3)4 (0.687 g, 0.595 mmol), and potassium carbonate (1.37 g, 9.9 mmol) in toluene (100 ml), water (20 ml), and ethanol (40 ml) was degassed and stirred for 2 hours under a nitrogen atmosphere while heating at 95 °C. Thereafter, the mixture was cooled, water was added to the mixture, and the organic phase was separated. The residue after evaporation of toluene was redissolved in dichloromethane, adsorbed on diatomaceous earth, and subjected to chromatography on a silica gel column using a gradient elution with a mixture of hexane and dichloromethane. The fractions containing the product were combined, the eluate was evaporated, and the residue was dried in vacuo to obtain the compound 18 (0.54 g). 1 1H-NMR (CD2Cl2, 500 MHz): 6.33 (s, 1H), 6.74 (d, 2H, J = 2 Hz), 6.87 - 6.94 (m, 4H), 7.04 - 7.07 (m, 6H), 7.12 - 7.25 (m, 7H), 7.28 - 7.34 (m, 8H).

[0563] Compound (19).

[0564] A mixture of compound 18 (540 mg, 0.79 mmol), aniline (108 mg, 1.16 mmol), Pd2(dba)3 (36 mg, 0.04 mmol), SPhos (32 mg, 0.08 mmol), and NaOtBu (290 mg, 3.017 mmol) in 100 ml of toluene was stirred at 110 °C under a nitrogen atmosphere for 19 h. Thereafter, the reaction mixture was cooled, toluene was distilled off using a rotary evaporator, the residue was redissolved in dichloromethane, adsorbed onto diatomaceous earth, and subjected to chromatography on a silica gel column with gradient elution using a mixture of hexane and dichloromethane. The fractions containing the product were combined, the eluate was evaporated, and dried in vacuo to give compound 19 (126 mg). MS: MH+ = 702. UV-vis (acetonitrile-water), λ max (nm): 302. 1 1H-NMR (CD2Cl2, 500 MHz): 6.33 (s, 1H), 6.74 (d, 1H, J = 2 Hz), 6.87 - 6.94 (m, 4H), 6.98 - 7.36 (m, 26H), 7.67 (s, 1H).

[0565] Compound V-4 (20).

[0566] Compound 19 (126 mg, 0.18 mmol) was dissolved in 10 ml of tert-butylbenzene under a nitrogen atmosphere, and then 0.42 ml of tert-butyllithium (1.7 M solution in pentane) was added. The resulting mixture was stirred at 76 °C for 30 min. Thereafter, the mixture was cooled with a dry ice / acetone bath, and then 0.12 ml of pure BBr3 was added in one portion. The mixture was stirred at ambient temperature (water bath) for about 10 min, and then 0.25 ml of diisopropylethylamine was added. The mixture was heated at 120 °C for 2 h. tert-Butylbenzene was distilled off using a rotary evaporator, the residue was redissolved in dichloromethane, adsorbed onto diatomaceous earth, and subjected to chromatography on a silica gel column with gradient elution using a mixture of hexane and dichloromethane to give compound V-4 (18 mg) which could be further purified by crystallization. MS: MH+ = 683. Uv-vis (acetonitrile-water), λ max (nm): 435, 413, 365, 336, 310, 248. 11H-NMR (CD2Cl2, 500 MHz): δ 6.26 (d, 2H, J = 8 Hz), 6.50 (d, 2H, J = 9 Hz), 6.76 (d, 2H, J = 9 Hz), 7.30 - 7.37 (m, 2H), 7.48 (d, 2H, J = 7 Hz), 7.55 (d, 4H, J = 8 Hz), 7.60 (t, 2H, J = 8 Hz), 7.64 - 7.69 (m, 4H), 7.74 - 7.79 (m, 4H), 7.95 (d, 2H, J = 8 Hz), 8.69 (d, 2H, J = 9 Hz). Photoluminescence (toluene): λ = 441 nm, full width at half maximum (fwhm) = 11 nm, quantum yield = 95%.

[0567] Device examples

[0568] (1) Materials

[0569] NDP-9 is 1,2,3-tris(cyanomethylidene)tris(2,3,5,6-tetrafluorobenzonitrile)-cyclopropane

[0570] HTM-1 is a fluorene-substituted arylamine

[0571] HTM-2 is a monoarylaminocarbazole

[0572] Host-1 is a dibenzofuran-substituted monoarylanthracene

[0573] Dopant-1 is a boron-containing polycyclic aromatic compound without a direct boron-nitrogen bond

[0574] ET-1 is a fluorene-substituted triazine

[0575] LiQ is lithium quinolate

[0576] (2) Devices

[0577] As described in detail below, the emissive layer is deposited by vapor deposition. In all cases, the substrate is cleaned in a detergent, rinsed with water, and then dried in nitrogen before use.

[0578] (3) Device Characterization

[0579] Device examples 1 - 2

[0580] The bottom-emitting device is 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 -7On or below the substrate, they sequentially receive the thermal evaporation of a hole injection material, a first hole transport material, a second hole transport material, a photoactive material, a host material, an electron transport material, and an electron injection material. The bottom-emitting device has a thermally evaporated Al cathode material. Then the chamber is evacuated, and the devices are encapsulated using a glass cover, a desiccant, and a UV-curable epoxide.

[0581] The device has the following structure, in sequence (unless otherwise specified, all ratios are by weight and all percentages are by weight, based on the total weight of the layer):

[0582] Glass substrate

[0583] Anode: ITO (50 nm)

[0584] HIL: HTM-1:NDP-9 97:3 (10 nm)

[0585] HTL1: HTM-1 (160 nm)

[0586] HTL2: HTM-2 (10 nm)

[0587] EML: Co-deposition of host-1 and dopant as shown in Table 1 (25 nm)

[0588] ETL: ET-1:LiQ 1:1 (27 nm)

[0589] EIL: LiQ (3 nm)

[0590] Cathode: Al (100 nm)

[0591] Table 1. Device results

[0592]

[0593] The concentration (%) is the weight percentage of the dopant in the emission layer; V10 is the driving voltage at 10 mA / cm 2 2. All other data are at 1000 nits. CIEx and CIEy are the x and y color coordinates according to the C.I.E. chromaticity scale (International Commission on Illumination, 1931); CE is the current efficiency in cd / A.

[0594] As can be seen from Table 1, the device with the compound of the present invention can have good efficiency at extremely saturated blue. This is an important characteristic for OLED applications that require a bottom-emitting device structure and saturated blue.

[0595] It should be noted that not all of the activities described above in the general description or examples are required. Some of the specific activities may not be required, and one or more other activities may be performed in addition to those described. Further, the order of the recited activities need not be the order in which they are performed.

[0596] In the foregoing specification, concepts have been described with reference to specific embodiments. However, one of ordinary skill in the art appreciates 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 in an illustrative rather than a restrictive sense, and all such modifications are intended to be included within the scope of the invention.

[0597] 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 that may cause any benefit, advantage, or solution to occur or become more apparent are not to be construed as a critical, required, or essential feature of any or all of the claims.

[0598] It is understood that certain features that are described herein in the context of separate embodiments may also be provided in combination in a single embodiment. Conversely, various features that are described in the context of a single embodiment for sake of brevity may also be provided separately or in any sub-combination. Further, the recitation of a value range within the specification includes each value within that range.

Claims

1. A polycyclic aromatic compound having the following formula V, wherein: Q 3 -Q 4 are the same or different and are selected from the group consisting of: NR 12 ; Q 5 selected from the group consisting of: B; Q 7 selected from the group consisting of: NR 12 ; R 1 、R 2 、R 9 -R 11 are the same or different each time they appear and are selected from the group consisting of: D, F, CN, C 1-20 alkyl; R 12 selected from the group consisting of: a carbocyclic aryl having 6-30 ring carbons or a deuterated analogue thereof; a, a1 and b are the same or different and are integers from 0 to 3; and c and d are the same or different and are integers from 0 to 2.

2. An organic electronic device comprising a first electrical contact, a second electrical contact, and a photoactive layer therebetween, the photoactive layer comprising the compound according to claim 1.

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