Attorney Docket No.: UDC-1685P2 (376.0038P)
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`ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
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`[0001] The present disclosure generally relates to organometallic compounds and formulations and their various
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`uses including as hosts or emitters in devices such as organic light emitting diodes andrelated electronic devices.
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`FIELD
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`BACKGROUND
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`[0002] Opto-clectronic devices that make usc of organic matcrials arc becoming increasingly desirable for various
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`reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic
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`devices have the potential for cost advantages over inorganic devices.
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`In addition, the inherent properties of organic
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`materials, such as their flexibility, may make them well suited for particular applications such as fabrication ona
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`flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices
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`(OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs,the organic
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`materials may have performance advantages over conventional materials.
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`[0003] OLEDs makcusc of thin organic films that emit light when voltage is applicd across the device. OLEDs
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`are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination,
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`and backlighting.
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`[0004] One application for phosphorescent emissive molecules is a full color display. Industry standards for such
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`a display call for pixels adapted to emit particular colors, referred to as "saturated" colors. In particular, these
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`standards call for saturated red, green, and blue pixels. Alternatively, the OLED can be designed to emit white light.
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`In conventional liquid crystal displays emission from a white backlightis filtered using absorption filters to produce
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`red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can beeither a
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`single emissive layer (EML) device or a stack structure. Color may be measured using CIE coordinates, which are
`well knownto the art.
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`SUMMARY
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`[0005]
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`In one aspect, the present disclosure provides a compound comprising a plurality of chemical groups;
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`wherein the compound comprisesa first ring;
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`wherein the first ring is formed by connecting the plurality of chemical groups one by one with a direct bond to each
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`other in a mannerto form one or more closed rings;
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`whereinthe first ring is a ring which has a minimumnumberof a plurality of ring atoms in the one or more closed
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`rings;
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`wherein the plurality of chemical groups comprisesa first chemical moiety selected from a group A consisting of
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`fused- or non-fused-tripheny lene, fused- or non-fused-tetraphenylene, fused- or non-fused-carbazole, fused- or non-
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`fused-dibenzothiophene, fused- or non-fused-dibenzofuran, fused- or non-fused-dibenzoselenophene, fused- or non-
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`fused- benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), fused- or non-fused-naphthalene, silyl, germyl, boryl,
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`Attorney Docket No.: UDC-1685P2 (376.0038P)
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`non-fused-pyridine, non-fused-pyridazine, non-fused-pyrimidine, non-fused-pyrazine, non-fused-triazine, non-
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`fused-imidazole, non-fused-benzimidazole, aza-(fused- or non-fused-triphenylene), aza-(fused- or non-fused-
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`carbazole), aza-(fused- or non-fused-dibenzothiophene), aza-(fused- or non-fused-dibenzofuran), aza-(fused- or non-
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`fused-dibenzoselenophene), aza-(fused- or non-fused-bimbim), and aza-(fused- or non-fused-naphthalene);
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`wherein the plurality of ring atomsofthe first ring comprises at least one moiety selected from the group consisting
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`of three or four atoms from a fused- or non-fused-6-memberedring, two or three atoms from a non-fused-5-
`memberedring, and a sp’ carbon atom;
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`wherein the plurality of chemical groups can be furthcr substituted by a substitucnt sclected from the group
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`consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl], heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino,
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`silyl, germyl, bory], alkenyl, cycloalkenyl, heteroalkenyl], alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester,
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`nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and any two
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`substitutions can be joined or fused into a ring; and
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`wherein the compoundis not a metal-containing compound; and
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`wherein the compound is not a compoundconsisting of only carbazole moities which are linked throughtheir 3,6
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`positions.
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`[0006]
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`In another aspect, the present disclosure provides a formulation of the compoundas described herein.
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`[0007]
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`In yet another aspect, the present disclosure provides an OLED having anorganic layer comprising the
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`compoundas described herein.
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`[0008]
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`In yet another aspect, the present disclosure provides a consumerproduct comprising an OLED with an
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`organic layer comprising the compoundas described herein.
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`BRIEF DESCRIPTION OF THE DRAWINGS
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`[0009] FIG. 1 shows an organic light emitting device.
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`[0010] FIG. 2 showsan inverted organic light emitting device that does not have a separate electron transport
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`layer.
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`A.
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`Terminology
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`DETAILED DESCRIPTION
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`[0011] Unless otherwise specified, the below terms used herein are defined as follows:
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`[0012] As used herein, the term "organic" includes polymeric materials as well as small molecule organic
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`materials that may be used to fabricate organic opto-electronic devices. "Small molecule" refers to any organic
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`material that is not a polymer, and "small molecules" may actually be quite large. Small molecules may include
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`Tepeal units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a
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`molecule from the "small molecule" class. Small molecules may also be incorporated into polymers, for example as
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`a pendent group on a polymer backboneoras a part of the backbone. Small molecules may also serve as the core
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`Attorney Docket No.: UDC-1685P2 (376.0038P)
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`moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a
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`dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a "small molecule,"
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`andit is believed that all dendrimers currently used in the field of OLEDs are small molecules.
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`[0013] As used herein, "top" means furthest away from the substrate, while "bottom" means closest to the
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`substrate. Where a first layer is described as "disposed over" a secondlayer, the first layer is disposed further away
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`from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer
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`is "in contact with" the second layer. For example, a cathode may be described as "disposed over" an anode, even
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`thoughthere are various organic laycrs in betwecn.
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`[0014] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in
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`and/or deposited froma liquid medium, either in solution or suspension form.
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`[0015] A ligand may be referred to as "photoactive" whenit is believed that the ligand directly contributes to the
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`photoactive properties of an emissive material. A ligand may bereferred to as "ancillary" whenit is believed that
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`the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may
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`alter the properties of a photoactive ligand.
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`[0016] As uscd hercin, and as would be gencrally understood by one skilled in the art, a first "Highest Occupicd
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`Molecular Orbital" (HOMO) or "Lowest Unoccupied Molecular Orbital" (LUMO)energy level is "greater than" or
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`"higher than" a second HOMO or LUMOenergylevel if the first energy level is closer to the vacuumenergy level.
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`Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO
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`energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher
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`LUMOenergy level correspondsto an electron affinity (EA) having a smaller absolute value (an EA thatis less
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`negative). Ona conventional energy level diagram, with the vacuum level at the top, the LUMOenergy level of a
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`material is higher than the HOMOenergy level of the same material. A "higher" HOMO or LUMOenergy level
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`appears closer to the top of such a diagram than a "lower" HOMO or LUMOenergy level.
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`[0017] As used herein, and as would be generally understood by one skilled inthe art, a first work functionis
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`"greater than" or “higher than" a second work functionif the first work function has a higher absolute value.
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`Because work functions are generally measured as negative numbersrelative to vacuum level, this means that a
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`"higher" work function is more negative. Ona conventional energy level diagram, with the vacuum levelat the top,
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`a “higher" work functionis illustrated as further away from the vacuum level in the downward direction. Thus, the
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`definitions of HOMO and LUMOenergy levels follow a different convention than work functions.
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`[0018] The terms "halo," "halogen," and "halide" are used interchangeably and refer to fluorine, chlorine, bromine,
`andiodine.
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`[0019] The term "acyl" refers to a substituted carbonyl] radical (C(O)-R;).
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`[0020] The term "ester" refers to a substituted oxycarbonyl (-O—C(O)-R, or —C(O)-O-R,) radical.
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`[0021]
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`‘The term "ether" refers to an —ORsradical.
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`[0022] The terms "sulfanyl" or "thio-ether" are used interchangeably and refer to a —SR; radical.
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`Attorney Docket No.: UDC-1685P2 (376.0038P)
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`[0023] The terms “selenyl” refers to a —SeRsradical.
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`[0024] The term "sulfinyl" refers to a—S(O)-R;radical.
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`[0025] The term "sulfonyl" refers to a —SOQ2—-R;radical.
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`[0026] The term "phosphino" refers to a —P(R;)3 radical, wheremeach R,; can be same or different.
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`[0027] The term "silyl" refers to a —Si(Rs)s radical, wherein each R; can be sameordifferent.
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`[0028] The term “germyl”refers to a -Ge(R,)s radical, wherein each R, can be sameor different.
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`[0029] The term "boryl" refers to a—B(Rs;)2 radical or its Lewis adduct —B(R;)3 radical, wherein Rs can be same or
`different.
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`[0030]
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`In cach of the above, R; can be hydrogen ora substituent selected from the group consisting of deuterium,
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`halogen, alkyl], cycloalkyl, heteroalky1, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl,
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`cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combination thereof. Preferred R, is selected from the
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`group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof.
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`[0031] The term "alkyl" refers to and includesbothstraight and branched chain alkyl radicals. Preferred alkyl
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`groups are those containing from oneto fifteen carbon atoms and includes methyl], ethyl, propyl, 1-methy lethy],
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`butyl, 1-mcthylpropyl, 2-mcthylpropyl, pentyl, 1-mcthylbutyl, 2-mcthylbuty1, 3-mcthylbutyl, 1,1-dimcthylpropyl,
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`1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group may be optionally substituted.
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`[0032] The term"cycloalkyl" refers to and includes monocyclic, polycyclic, and spiro alkyl radicals. Preferred
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`cycloalkyl groups are those containing 3 to 12 ring carbon atomsandincludes cyclopropyl, cyclopentyl, cyclohexyl,
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`bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamanty], and the like. Additionally, the cycloalkyl group
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`may be optionally substituted.
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`[0033] The terms "heteroalkyl" or “heterocycloalkyl" refer to an alkyl or a cycloalkyl radical, respectively, having
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`at least one carbon atom replaced by a heteroatom. Optionally the at least one heteroatom is selected from O, 8, N,
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`P, B, Siand Se, preferably, O, S or N. Additionally, the heteroalkyl or heterocycloalkyl group may be optionally
`substituted.
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`[0034] The term "alkenyl" refers to and includes both straight and branched chain alkene radicals. Alkenyl groups
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`are essentially alkyl groupsthat include at least one carbon-carbon double bondin the alkyl chain. Cycloalkenyl
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`groupsare essentially cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalky]ring.
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`The term "heteroalkenyl" as used herein refers to an alkeny] radical having at least one carbon atom replaced by a
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`heteroatom. Optionally the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably, O. S, or N.
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`Preferred alkenyl, cycloalkeny1, or heteroalkenyl groups are those containing twoto fifteen carbon atoms.
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`Additionally, the alkenyl, cycloalkenyl, or heteroalkenyl group may be optionally substituted.
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`[0035] The term "alkynyl" refers to and includes bothstraight and branched chain alkyne radicals. Alkynyl groups
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`are essentially alkyl groups that include at least one carbon-carbontriple bond in the alkyl chain. Preferred alkynyl
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`groups are those containing twoto fifteen carbon atoms. Additionally, the alkynyl group may be optionally
`substituted.
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`Attorney Docket No.: UDC-1685P2 (376.0038P)
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`[0036] The terms "aralkyl" or "arylalkyl" are used interchangeably andrefer to an alkyl group that is substituted
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`with an atyl group. Additionally, the aralkyl group may be optionally substituted.
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`[0037] The term "heterocyclic group" refers to and includes aromatic and non-aromatic cyclic radicals containing
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`at least one heteroatom. Optionally the at least one heteroatomis selected from O, 8, N, P, B, Si, and Se, preferably,
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`O, S, or N. Hetero-aromatic cyclic radicals may be used interchangeably with heteroaryl. Preferred hetero-non-
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`aromatic cyclic groups are those containing 3 to 7 ring atoms which includesat least one hetero atom, and includes
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`cyclic amines such as morpholino, piperidino, pyrrolidino, and the like, and cyclic ethers/thio-ethers, such as
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`tetrahydrofuran, tctrahydropyran, tctrahydrothiophenc, and the like. Additionally, the hetcrocyclic group may be
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`optionally substituted.
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`[0038] The term "aryl" refers to and includes bothsingle-ring aromatic hydrocarbyl groups and polycyclic
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`aromatic ring systems. The polycyclic rings may have two or more rings in which two carbons are commonto two
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`adjoining rings (the rings are "fused") wherein at least one of the rings is an aromatic hydrocarbyl group,e.g., the
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`other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred aryl groups are those
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`containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon
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`atoms. Especially preferred is an aryl group having six carbons, tcn carbons or twelve carbons. Suitable aryl groups
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`include phenyl, biphenyl, tripheny], tripheny lene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene,
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`fMuorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl], tripheny], tryphenylene, Muorene, and
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`naphthalene. Additionally, the aryl group may be optionally substituted.
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`[0039] The term "heteroaryl" refers to and includes both single-ring aromatic groups and polycyclic aromatic ring
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`systemsthat include at least one heteroatom. The heteroatoms include, but are not limited to O, S, N, P, B, $i, and
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`Se. In many instances, O, S, or N are the preferred heteroatoms. Hetero-single rng aromatic systems are preferably
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`single rings with 5 or 6 ring atoms, and the ring can have from oneto six heteroatoms. The hetero-polycyclic ring
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`systems can have two or more rings in which two atoms are commonto two adjoining rings (the rings are "fused")
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`whereinat least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkeny|s, ary],
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`heterocycles, and/or heteroaryls. The hetero-polycyclic aromatic ring systems can have from one to six heteroatoms
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`per ting of the polycyclic aromatic ring system. Preferred heteroary] groups are those containing three to thirty
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`carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable
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`heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thhophene, benzofuran,
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`benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole,
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`imidazole,triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine,
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`pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine,
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`benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline,
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`naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine,
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`benzofuropyridine, furodipynidine, benzothienopynidine, thienodipyridine, benzoselenophenopyridine, and
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`selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole,
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`indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine,
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`and aza-analogsthereof. Additionally, the heteroaryl group may be optionally substituted.
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`[0040] Of the aryl and heteroaryl groupslisted above. the groups of triphenylene, naphthalene, anthracene,
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`dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine,
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`pyrimidine, triazine, and benzimidazole, and the respective aza-analogs of each thereof are of particular interest.
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`[0041] The termsalkyl, cycloalkyl, heteroalkyl, heterocycloalky1, alkenyl, cycloalkenyl, heteroalkeny1, alkyny1,
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`aralkyl, heterocyclic group, aryl, and heteroaryl, as used herein, are independently unsubstituted, or independently
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`substituted, with onc or morc gencral substitucnts.
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`[0042]
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`In many instances, the general substituents are selected from the group consisting of deuterium, halogen,
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`alkyl, cycloalkyl, heteroalkyl, heterocycloalky], arylalkyl, alkoxy, aryloxy, amino, silyl, germy], alkenyl],
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`cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfany1,
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`selenyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof.
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`[0043]
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`In someinstances, the preferred general substituents are selected from the group consisting of deuterium,
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`fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino,silyl, boryl, alkenyl, cycloalkenyl, heteroalkeny1,
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`aryl, hetcroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
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`[0044]
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`In someinstances, the more preferred general substituents are selected from the group consisting of
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`deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, boryl, aryl, heteroaryl, sulfanyl, and
`combinations thereof.
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`[0045]
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`In yet other instances, the most preferred general substituents are selected from the group consisting of
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`deuterium, fluorine, alkyl, cycloalkyl], aryl, heteroaryl, and combinationsthereof.
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`[0046] The terms "substituted" and “substitution" refer to a substituent other than H that is bonded to the relevant
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`position, e.g., a carbon or nitrogen. For example, when R! represents mono-substitution, then one R! must be other
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`than H (i.c., a substitution). Similarly, when R' represents di-substitution, then two of R' must be other than H.
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`Similarly, when R! represents zero or no substitution, R', for example, can be a hydrogenfor available valencies of
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`ring atoms, as in carbon atoms for benzene and the nitrogen atom in pyrrole, or simply represents nothing for ring
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`atoms with fully filled valencies, e.g., the nitrogen atom in pyridine. The maximum numberof substitutions
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`possible in a ring structure will depend on the total numberof available valencies in the ring atoms.
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`[0047] As used herein, “combinations thereof" indicates that one or more members of the applicable list are
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`combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from
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`the applicable list. For example, an alkyl and deuterium can be combined to forma partial or fully deuterated alky1
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`group; a halogen and alkyl can be combinedto form a halogenated alky] substituent; and a halogen, alkyl, and aryl
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`can be combined to form a halogenated arylalkyl. In one instance, the term substitution includes a combination of
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`two to four of the listed groups. In another instance, the term substitution includes a combination of twoto three
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`groups. In yet another instance, the term substitution includes a combination of two groups. Preferred combinations
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`of substituent groups are those that contain up to fifty atoms that are not hydrogen or deuterium, or those which
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`Attorney Docket No.: UDC-1685P2 (376.0038P)
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`include up to forty atomsthat are not hydrogen or deuterium,or those that include up to thirty atoms that are not
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`hydrogen or deuterium. In many instances, a preferred combination of substituent groups will include up to twenty
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`atomsthat are not hydrogen or deuterium.
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`[0048] The "aza" designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene,etc.
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`means that one or more of the C-H groups in the respective aromatic ring can be replaced by a nitrogen atom, for
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`example, and without any limitation, azatriphenylene encompasses both dibenzo[f//]quinoxaline and
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`dibenzo|f,|quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-
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`derivatives described above, and all such analogsare intended to be cncompasscdby the termsassct forth hercin.
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`[0049] As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compoundscan be readily
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`prepared using methods knowninthe art. For example, U.S. Pat. No. 8,557,400, Patent Pub. No. WO 2006/095951,
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`and U.S. Pat. Application Pub. No. US 2011/0037057, which are hereby incorporated by reference in their entireties,
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`describe the making of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan, ef
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`al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744-65, which
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`are incorporated by reference in their entireties, describe the deuteration of the methylene hydrogens in benzy!
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`amines and cfficicnt pathways to replace aromatic ring hydrogens with dcutcrium, respectively.
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`[0050]
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`It is to be understood that when a molecular fragment is described as being a substituent or otherwise
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`attached to another moiety, its name may be written as if it were a fragment (c.g. phenyl, phenylene, naphthyl,
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`dibenzofury]) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these
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`different ways of designating a substituent or attached fragment are considered to be equivalent.
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`[0051]
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`In someinstance, a pair of adjacent substituents can be optionally joined or fused into a ring. The preferred
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`ring is a five, six, or seven-membered carbocyclic or heterocyclic ring, includes both instances where the portion of
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`the ring formed bythe pair of substituents is saturated and where the portion of the ring formed by the pair of
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`substituents is unsaturated. As used herein, "adjacent" means that the two substituents involved can be on the same
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`ring next to each other, or on two neighboring rings having the two closest available substitutable positions, such as
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`2, 2' positions in a biphenyl, or 1, 8 position in a naphthalene, as long as they can form a stable fused ring system.
`
`B.
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`The Compoundsof the Present Disclosure
`
`[0052]
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`In one aspect, the present disclosure provides a compound comprising a plurality of chemical groups;
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`wherein the compound comprisesa first ring;
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`wherein the first ring is formed by connecting the plurality of chemical groups one by one with a direct bond to each
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`other ina mannerto form one ore more closed rings;
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`whereinthe first ring is a ring which has a minimum number of a plurality of ring atoms in the one or more closed
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`rings;
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`wherein the plurality of chemical groups comprisesa first chemical moiety selected from a group A consisting of
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`fused- or non-fused-triphenylene, fused- or non-fused-tetraphenylene, fused- or non-fused-carbazole, fused- or non-
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`fused-dibenzothiophene, fused- or non-fused-dibenzofuran, fused- or non-fused-dibenzoselenophene, fused- or non-
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`fused- benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), fused- or non-fused-naphthalene,silyl, germyl, boryl,
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`non-fused-pyridine, non-fused-pyridazine, non-fused-pyrimidine, non-fused-pyrazine, non-fused-triazine, non-
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`fused-imidazole, non-fused-benzimidazole, aza-(fused- or non-fused-tripheny lene), aza-(fused- or non-fused-
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`carbazole), aza-(fused- or non-fused-dibenzothiophene), aza-(fused- or non-fused-dibenzofuran), aza-(fused- or non-
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`fused-dibenzoselenophene), aza-(fused- or non-fused-bimbim), and aza-(fused- or non-fused-naphthalene);
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`wherein the plurality of ring atomsofthe first ring comprises at least one moiety selected from the group consisting
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`of three or four atoms from a fuscd- or non-fuscd-6-memberedring, two or three atoms from a non-fuscd-5-
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`membered ring, and a sp*® carbon atom;
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`wherein the plurality of chemical groups can be further substituted by a substituent selected from the group
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`consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino,
`
`silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester,
`
`nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and any two
`
`substitutions can be joined or fused into a ring; and
`
`wherein the compoundis not a mctal-containing compound: and
`
`wherein the compound is not a compound consisting of only carbazole moities which are linked throughtheir 3.6
`
`positions.
`
`[0033] The plurality of chemical groups as defined herein are referred to the chemical moieties used to form the
`
`first ring. Each of such chemical moieties can be a single atom, a single unfused ring, or a single fused ring system
`
`without any substitutions. Therefore, although each of such chemical moieties can be further substituted by same or
`
`different substituents, when we say two same chemical moieties, we only refer to the two same single atom, single
`
`unfused ring, or the single fused ring system itself regardless what else the additional substitutions they may have.
`
`For a single fused ring system, the complete but not the partial fused ring system is considered as a chemical moiety
`
`defined herein. For example, indolocarbazole is a fused-carbazole. In another words, when a chemical moiety is a
`
`carbazole, it carries its original meaning of carbazole,i.e., a non-fused carbazole.
`
`[0054]
`
`Thefirst ring is considered to have a minimum numberof ring atoms if there are more than one closed ring
`
`being formed. The ring atoms are counted such that there are no bridges between any two ring atoms which contain
`
`less atoms than any (or both) of the two parts of the ring they are bridging. In other words,if there were any bridge
`
`with less atoms than any (or both) of the twoparts of the ring they are bridging, the bridge would instead be part of
`
`the first ring with the minimumnumberof ring atoms.
`
`[0055]
`
`In some embodiments, the first chemical moiety of group A is selected from a group B consisting of
`
`triphenylene, tetraphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, bimbim,
`
`naphthalene,silyl, germyl, boryl, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazole, benzimidazole,
`
`indolocarbazole, indolobenzo[d]benzo[4,5]imidazo| 1,2-a]imidazole, indolodibenzothiophene, indolodibenzofuran,
`
`indolodibenzosilole, indolofluorene, benzocarbazole, naphthobenzofuran, naphthobenzothiophene, benzofluorene,
`
`8
`
`

`

`Attorney Docket No.: UDC-1685P2 (376.0038P)
`
`aza-tripheny lene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-bimbim,
`
`aza-naphthalene, aza-indolocarbazole, aza-indolobenzo[d]benzo[4,5 ]imidazo[1,2-a]imidazole, aza-
`
`indolodibenzothiophene, aza-indolodibenzofuran, aza-indolofluorene, aza-indolodibenzosilole, aza-benzocarbazole,
`
`aza-naphthobenzofuran, aza-naphthobenzothiophene, and aza-benzofuorene.
`
`[0056]
`
`In some embodiments, group A is selected from the group C consisting of triazine, triphenylene, carbazole,
`
`dibenzothiophene, dibenzofuran, bimbim, indolocarbazole, indolodibenzothiophene, and indolodibenzofuran.
`
`[0037]
`
`In some embodiments, group A is selected from the group D consisting oftriazine, triphenylene, carbazole,
`
`dibenzothiophenc, dibenzofuran, and bimbim.
`
`[0058]
`
`In some embodiments, the plurality of ring atoms of the first ring comprisesat least three or four atoms
`
`from a non-fused-6-memberedring.
`
`[0059]
`
`In some embodiments, the plurality of ring atomsof the first ring comprises two or three atoms from a non-
`
`fused-5-memberedring.
`
`[0060]
`
`In some embodiments, wherein the plurality of ring atomsofthe first ring comprises a sp* carbon atom.
`
`[0061]
`
`In some embodiments, the plurality of ring atomsof the first ring comprisesat least one heteroatom.
`
`[0062]
`
`In somc cmbodiments, the at lcast onc hetcroatom is sclected from the group consisting of N, B, O, Si, S,
`
`Ge, and Se.
`
`[0063]
`
`In some embodiments, the plurality of ring atoms comprises a minimum number of same or different
`
`heteroatoms, wherein the minimum numberis selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10.
`
`[0064]
`
`In some embodiments, the plurality of ring atomsofthe first ring is selected from the group consisting of
`
`C, N, 8, O, Si, and B.
`
`[0063]
`
`In some embodiments, the plurality of ring atomsis selected from the group consisting of C; and N.
`
`[0066]
`
`In some embodiments, the plurality of ring atomsis selected from the group consisting of C, and S.
`
`[0067]
`
`In some embodiments, the plurality of ring atoms is selected from the group consisting of C and O.
`
`[0068]
`
`In some embodiments, the plurality of ring atomsis selected from the group consisting of C, and S1.
`
`[0069]
`
`In some embodiments, the plurality of ring atomsis selected from the group consisting of C, and B.
`
`[0070]
`
`Insome embodiments, the plurality of ring atoms is selected from the group consisting of C, N, and S.
`
`[0071]
`
`Insome embodiments, the plurality of ring atoms is selected from the group consisting of C, N, and O.
`
`[0072]
`
`In some embodiments, the plurality of ring atoms is selected from the group consisting of C, N, and Si.
`
`[0073]
`
`In some embodiments, the plurality of ring atomsis selected from the group consisting of C, N, and B.
`
`[0074]
`
`In some embodiments, the plurality of ring atomsis selected from the group consisting of C, S, and B.
`
`[0075]
`
`In some embodiments, the plurality of ring atomsis selected from the group consisting of C, O, and B.
`
`[0076]
`
`Insome embodiments, the plurality of ring atomsis selected from the group consisting of C, Si, and B.
`
`[0077]
`
`Insome embodiments, the plurality of chemical groupsis further substituted by at least one chemical
`
`moiety selected from group A as defined above.
`
`

`

`Attorney Docket No.: UDC-1685P2 (376.0038P)
`
`[0078]
`
`In some embodiments, the plurality of chemical groups is further substituted by at least two same or
`
`different chemical moieties selected from group A as defined above.
`
`[0079]
`
`In some embodiments, the first chemical moiety is further substituted by at least one chemical moiety
`
`selected from group A as defined above.
`
`[0080]
`
`In some embodiments, the first chemical moiety is further substituted by at least two sameordifferent
`
`chemical moieties selected from group A as defined above.
`
`[0081]
`
`In some embodiments, the plurality of chemical groups further comprises a second chemical moiety
`
`sclected from group A as defined above; and wherein the first chemical moicty and the second chemical moicty can
`be same or different from cach other.
`
`[0082]
`
`In some embodiments, the plurality of chemical groups further comprises a third chemical moiety selected
`
`from group A as defined above; and wherein the first chemical moiety, second chemical moiety, and the third
`
`chemical moiety can be sameor different from each other.
`
`[0083]
`
`In some embodiments, the plurality of chemical groups further comprises a fourth chemical moiety selected
`
`from group A as defined above; and whereinthe first chemical moiety, second chemical moiety, the third chemical
`
`moicty, and the fourth chcmical moicty can be same ordifferent from cach other.
`
`[0084]
`
`In some embodiments, the first chemical moiety is the only chemical moiety selected from group A as
`
`defined above. This means the chemical moieties in the group A can only be used once to formthefirst ring.
`
`However, the compound can still comprise one or more chemical moieties from the group A outsidethe first ring.
`
`[0085]
`
`In some embodiments, the first and the second chemical moieties are selected from the group C of the
`
`following pairs