WO2019195104A1 - Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques - Google Patents

Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques Download PDF

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Publication number
WO2019195104A1
WO2019195104A1 PCT/US2019/024856 US2019024856W WO2019195104A1 WO 2019195104 A1 WO2019195104 A1 WO 2019195104A1 US 2019024856 W US2019024856 W US 2019024856W WO 2019195104 A1 WO2019195104 A1 WO 2019195104A1
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compound
light
formula
layer
organic
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PCT/US2019/024856
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English (en)
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Shuo-Hsien Cheng
Yoshitake Suzuki
Yu Seok YANG
Naoto Notsuka
Hayato Kakizoe
Makoto Yoshizaki
Ayataka Endo
Jorge AGUILERA-IPARRAGUIRRE
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Kyulux, Inc.
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Publication of WO2019195104A1 publication Critical patent/WO2019195104A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • OLED organic light-emitting diode
  • LED light-emitting diode
  • a problem inherent in OLED displays is the limited lifetime of the organic compounds. OLEDs that emit blue light, in particular, degrade at a significantly increased rate as compared to green or red OLEDs.
  • OLED materials rely on the radiative decay of molecular excited states (excitons) generated by recombination of electrons and holes in a host transport material.
  • excitons molecular excited states
  • the nature of excitation results in interactions between electrons and holes that split the excited states into bright singlets (with a total spin of 0) and dark triplets (with a total spin of 1). Since the recombination of electrons and holes affords a statistical mixture of four spin states (one singlet and three triplet sublevels), conventional OLEDs have a maximum theoretical efficiency of 25%.
  • OLED material design has focused on harvesting the remaining energy from the normally dark triplets.
  • Recent work to create efficient phosphors, which emit light from the normally dark triplet state have resulted in green and red OLEDs.
  • Other colors, such as blue, however, require higher energy excited states, which accelerates the degradation process of the OLED.
  • the fundamental limiting factor to the triplet-singlet transition rate is a value of the parameter jffti/AEsi , where i3 ⁇ 4 is the coupling energy due to hyperfme or spin-orbit interactions, and AEST is the energetic splitting between singlet and triplet states.
  • the present disclosure relates to novel materials for OLEDs.
  • novel materials for OLEDs In some
  • these OLEDs can reach higher excitation states without rapid degradation. It has now been discovered that thermally activated delayed fluorescence (T which relies on minimization of AEST as opposed to maximization of B&, can transfer population between singlet levels and triplet sublevels in a relevant timescale, such as, for example, lps-10ms.
  • T thermally activated delayed fluorescence
  • the compounds described herein are capable of luminescing at higher energy excitation states than compounds previously described.
  • the present disclosure provides compounds of Formula (I) or (II):
  • D is independently selected from
  • P and P’ are independently selected from H, deuterium,
  • At least one instance of P is selected from Pl to P23;
  • X and X’ are independently selected from C(H), and N;
  • Y is independently selected from C and Si;
  • Z is independently selected from S, O, and N(Ph).
  • the present disclosure provides compounds of Formula (I) or (II):
  • D is independently selected from
  • P and P’ are independently selected from H, deuterium, X and X’ are C(R);
  • R is independently H, deuterium, Ci-4-alkyl, C 6 -i2-aryl, or C 5 -i2-heteroaryl.
  • the present disclosure provides delayed fluorescent emitters comprising a compound of Formula (I) or (II).
  • the present disclosure provides organic light-emitting diodes (OLED) comprising a compound of Formula (I) or (II).
  • an organic light-emitting diode comprising an anode, a cathode, and at least one organic layer comprising a light- emitting layer between the anode and the cathode, wherein the light-emitting layer comprises:
  • an organic light-emitting diode comprising an anode, a cathode, and at least one organic layer comprising a light- emitting layer between the anode and the cathode, wherein the light-emitting layer comprises:
  • an organic light-emitting diode comprising an anode, a cathode, and at least one organic layer comprising a light- emitting layer between the anode and the cathode, wherein the light-emitting layer comprises:
  • a host material a compound of Formula (I) or (II); and a light-emitting material which is not a compound of Formula (I) or (II).
  • an organic light-emitting diode comprising an anode, a cathode, and at least one organic layer comprising a light- emitting layer between the anode and the cathode, wherein the light-emitting layer comprises:
  • the compounds of Formula (I) or (II) are used in a screen or a display.
  • the present disclosure relates to a method of manufacturing an OLED display, the method comprising:
  • Fig. 1 is a schematic wherein 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injection layer, 4 denotes a hole transporting layer, 5 denotes a light-emitting layer, 6 denotes an electron transporting layer, and 7 denotes a cathode.
  • the present disclosure provides a compound of Formula (I) or (II):
  • D is independently selected from
  • P and P’ are independently selected from H, deuterium,
  • At least one instance of P is selected from Pl to P23;
  • X and X’ are independently selected from C(H), and N;
  • Y is independently selected from C and Si;
  • Z is independently selected from S, O, and N(Ph).
  • the present disclosure provides compounds of Formula (I) or (II):
  • D is independently selected from
  • P and P’ are independently selected from H, deuterium, X and X’ are C(R);
  • R is independently H, deuterium, Ci-4-alkyl, C6-i2-aryl, or C 5 -i2-heteroaryl.
  • acyl is art-recognized and refers to a group represented by the general Formula hydrocarbylC(O)-, preferably alkylC(O)-.
  • acylamino is art-recognized and refers to an amino group substituted with an acyl group and may be represented, for example, by the Formula
  • acyloxy is art-recognized and refers to a group represented by the general Formula hydrocarbylC(0)0-, preferably alkylC(0)0-.
  • alkoxy refers to an alkyl group, having an oxygen attached thereto. In some embodiments, an alkoxy has 1-20 carbon. In some embodimens, an alkoxy has 1- 12 carbon atoms. Representative alkoxy groups include methoxy, trifluoromethoxy, ethoxy, propoxy, tert-butoxy and the like.
  • alkoxyalkyl refers to an alkyl group substituted with an alkoxy group and may be represented by the general Formula alkyl-O-alkyl.
  • alkenyl refers to an aliphatic group comprising at least one double bond and is intended to include both“unsubstituted alkenyls” and “substituted alkenyls”, the latter of which refers to alkenyl moieties having substituents replacing a hydrogen on one or more carbons of the alkenyl group.
  • a straight chained or branched alkenyl group has from 1 to about 20 carbon atoms, preferably from 1 to about 12 unless otherwise defined. Such substituents may occur on one or more carbons that are included or not included in one or more double bonds.
  • substituents include all those contemplated for alkyl groups, as discussed below, except where stability is prohibitive.
  • substitution of alkenyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, or heteroaryl groups is contemplated.
  • An“alkyl” group or“alkane” is a straight chained or branched non-aromatic hydrocarbon which is completely saturated.
  • a straight chained or branched alkyl group has from 1 to about 20 carbon atoms, preferably from 1 to about 12 unless otherwise defined.
  • the alkyl group has from 1 to 8 carbon atoms, from 1 to 6 carbon atoms, from 1 to 4 carbon atoms, or from 1 to 3 carbon atoms.
  • straight chained and branched alkyl groups include methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, pentyl and octyl.
  • alkyl as used throughout the specification, examples, and claims is intended to include both“unsubstituted alkyls” and“substituted alkyls”, the latter of which refers to alkyl moieties having substituents replacing a hydrogen on one or more substitutable carbons of the hydrocarbon backbone.
  • substituents can include, for example, a halogen (e.g., fluoro), a hydroxyl, a carbonyl (such as a carboxyl, an alkoxycarbonyl, a formyl, or an acyl), a thiocarbonyl (such as a thioester, a thioacetate, or a thioformate), an alkoxy, a phosphoryl, a phosphate, a phosphonate, a phosphinate, an amino, an amido, an amidine, an imine, a cyano, a nitro, an azido, a sulfhydryl, an alkylthio, a sulfate, a sulfonate, a sulfamoyl, a sulfonamido, a sulfonyl, a heterocyclyl, an aralkyl, or an aromatic or
  • a halogen
  • the substituents on substituted alkyls are selected from Ci- 6 alkyl, C3-6 cycloalkyl, halogen, carbonyl, cyano, or hydroxyl. In more preferred embodiments, the substituents on substituted alkyls are selected from fluoro, carbonyl, cyano, or hydroxyl. It will be understood by those skilled in the art that the moieties substituted on the hydrocarbon chain can themselves be substituted, if appropriate. For instance, the substituents of a substituted alkyl may include substituted and unsubstituted forms of amino, azido, imino, amido, phosphoryl (including phosphonate and
  • phosphinate sulfonyl (including sulfate, sulfonamido, sulfamoyl and sulfonate), and silyl groups, as well as ethers, alkylthios, carbonyls (including ketones, aldehydes, carboxylates, and esters), -CF 3 , -CN and the like.
  • ethers alkylthios
  • carbonyls including ketones, aldehydes, carboxylates, and esters
  • -CF 3 exemplary substituted alkyls are described below.
  • Cycloalkyls can be further substituted with alkyls, alkenyls, alkoxys, alkylthios, aminoalkyls, carbonyl -substituted alkyls, -CF 3 , -CN, and the like.
  • Cx- y when used in conjunction with a chemical moiety, such as, acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant to include groups that contain from x to y carbons in the chain.
  • the term“Cx- y alkyl” refers to substituted or unsubstituted saturated hydrocarbon groups, including straight-chain alkyl and branched- chain alkyl groups that contain from x to y carbons in the chain, including haloalkyl groups.
  • Preferred haloalkyl groups include trifluoromethyl, difluoromethyl, 2,2,2- trifluoroethyl, and pentafluoroethyl.
  • Co alkyl indicates a hydrogen where the group is in a terminal position, a bond if internal.
  • the terms“C2- y alkenyl” and“C2- y alkynyl” refer to substituted or unsubstituted unsaturated aliphatic groups analogous in length and possible substitution to the alkyls described above, but that contain at least one double or triple bond respectively.
  • alkylamino refers to an amino group substituted with at least one alkyl group.
  • alkylthio refers to a thiol group substituted with an alkyl group and may be represented by the general Formula alkylS-.
  • arylthio refers to a thiol group substituted with an aryl group and may be represented by the general Formula arylS-.
  • alkynyl refers to an aliphatic group comprising at least one triple bond and is intended to include both“unsubstituted alkynyls” and “substituted alkynyls”, the latter of which refers to alkynyl moieties having substituents replacing a hydrogen on one or more carbons of the alkynyl group.
  • a straight chained or branched alkynyl group has from 1 to about 20 carbon atoms, preferably from 1 to about 10 unless otherwise defined. Such substituents may occur on one or more carbons that are included or not included in one or more triple bonds.
  • substituents include all those contemplated for alkyl groups, as discussed above, except where stability is prohibitive.
  • substitution of alkynyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, or heteroaryl groups is contemplated.
  • the term“amide”, as used herein, refers to a group
  • each R A independently represent a hydrogen or hydrocarbyl group, or two R A are taken together with the N atom to which they are attached complete a heterocycle having from 4 to 8 atoms in the ring structure.
  • each R A independently represents a hydrogen or a hydrocarbyl group, or two
  • R A are taken together with the N atom to which they are attached complete a heterocycle having from 4 to 8 atoms in the ring structure.
  • aminoalkyl refers to an alkyl group substituted with an amino group.
  • aralkyl refers to an alkyl group substituted with an aryl group.
  • aryl as used herein include substituted or unsubstituted single-ring aromatic groups in which each atom of the ring is carbon.
  • the ring is a 6- or 20-membered ring, more preferably a 6-membered ring.
  • an aryl has 6-40 carbon atoms, more preferably has 6-25 carbon atoms.
  • aryl also includes polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjoining rings wherein at least one of the rings is aromatic, e.g., the other cyclic rings can be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyls.
  • Aryl groups include benzene, naphthalene, phenanthrene, phenol, aniline, and the like.
  • each R A independently represent hydrogen or a hydrocarbyl group, such as an alkyl group, or both R A taken together with the intervening atom(s) complete a heterocycle having from 4 to 8 atoms in the ring structure.
  • carbocycle refers to a saturated or unsaturated ring in which each atom of the ring is carbon.
  • a carbocylic group has from 3 to 20 carbon atoms.
  • carbocycle includes both aromatic carbocycles and non-aromatic carbocycles.
  • Non-aromatic carbocycles include both cycloalkane rings, in which all carbon atoms are saturated, and cycloalkene rings, which contain at least one double bond.
  • Carbocycle includes 5-7 membered monocyclic and 8-12 membered bicyclic rings. Each ring of a bicyclic carbocycle may be selected from saturated, unsaturated and aromatic rings.
  • Carbocycle includes bicyclic molecules in which one, two or three or more atoms are shared between the two rings.
  • the term“fused carbocycle” refers to a bicyclic carbocycle in which each of the rings shares two adjacent atoms with the other ring.
  • Each ring of a fused carbocycle may be selected from saturated, unsaturated and aromatic rings.
  • an aromatic ring e.g., phenyl (Ph)
  • Ph may be fused to a saturated or unsaturated ring, e.g., cyclohexane, cyclopentane, or cyclohexene.
  • Any combination of saturated, unsaturated and aromatic bicyclic rings, as valence permits, is included in the definition of carbocyclic.
  • Exemplary “carbocycles” include cyclopentane, cyclohexane, bicyclo[2.2. l]heptane, 1,5- cyclooctadiene, l,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]oct-3-ene, naphthalene and adamantane.
  • Exemplary fused carbocycles include decalin, naphthalene, 1, 2,3,4- tetrahydronaphthalene, bicyclo[4.2.0]octane, 4,5,6,7-tetrahydro-lH-indene and bicyclo[4.l.0]hept-3-ene.“Carbocycles” may be susbstituted at any one or more positions capable of bearing a hydrogen atom.
  • A“cycloalkyl” group is a cyclic hydrocarbon which is completely saturated.
  • “Cycloalkyl” includes monocyclic and bicyclic rings. Preferably, a cycloalkyl group has from 3 to 20 carbon atoms. Typically, a monocyclic cycloalkyl group has from 3 to about 10 carbon atoms, more typically 3 to 8 carbon atoms unless otherwise defined.
  • the second ring of a bicyclic cycloalkyl may be selected from saturated, unsaturated and aromatic rings. Cycloalkyl includes bicyclic molecules in which one, two or three or more atoms are shared between the two rings.
  • fused cycloalkyl refers to a bicyclic cycloalkyl in which each of the rings shares two adjacent atoms with the other ring.
  • the second ring of a fused bicyclic cycloalkyl may be selected from saturated, unsaturated and aromatic rings.
  • A“cycloalkenyl” group is a cyclic hydrocarbon comprising one or more double bonds.
  • carbocyclylalkyl refers to an alkyl group substituted with a carbocycle group.
  • carbonate refers to a group -OC02-R A , wherein R A represents a hydrocarbyl group.
  • ester refers to a group -C(0)OR A wherein R A represents a hydrocarbyl group.
  • ether refers to a hydrocarbyl group linked through an oxygen to another hydrocarbyl group. Accordingly, an ether substituent of a hydrocarbyl group may be hydrocarbyl-O-. Ethers may be either symmetrical or unsymmetrical. Examples of ethers include, but are not limited to, heterocycle-O-heterocycle and aryl-O- heterocycle. Ethers include“alkoxyalkyl” groups, which may be represented by the general formula alkyl-O-alkyl.
  • halo and“halogen” as used herein means halogen and includes chloro, fluoro, bromo, and iodo.
  • heteroalkyl and“heteroaralkyl”, as used herein, refers to an alkyl group substituted with a hetaryl group.
  • heteroalkyl refers to a saturated or unsaturated chain of carbon atoms and at least one heteroatom, wherein no two heteroatoms are adjacent.
  • heteroaryl and“hetaryl” include substituted or unsubstituted aromatic single ring structures, preferably 5- to 20-membered rings, more preferably 5- to 6-membered rings, whose ring structures include at least one heteroatom, preferably one to four heteroatoms, more preferably one or two heteroatoms.
  • a heteroaryl has 2-40 carbon atoms, more preferably has 2-25 carbon atoms.
  • heteroaryl and“hetaryl” also include polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjoining rings wherein at least one of the rings is heteroaromatic, e.g., the other cyclic rings can be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyls.
  • Heteroaryl groups include, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, and carbazole, and the like.
  • aryloxy refers to an aryl group, having an oxygen attached thereto.
  • an aryloxy has 6-40 carbon atoms, more preferably has 6-25 carbon atoms.
  • heteroaryloxy refers to an aryl group, having an oxygen attached thereto.
  • a heteroaryloxy has 3-40 carbon atoms, more preferably has 3-25 carbon atoms.
  • heteroatom as used herein means an atom of any element other than carbon or hydrogen. Preferred heteroatoms are nitrogen, oxygen, and sulfur.
  • heterocyclyl refers to substituted or unsubstituted non-aromatic ring structures, preferably 3- to 20-membered rings, more preferably 3- to 7-membered rings, whose ring structures include at least one heteroatom, preferably one to four heteroatoms, more preferably one or two heteroatoms.
  • heterocyclyl and“heterocyclic” also include polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjoining rings wherein at least one of the rings is heterocyclic, e.g., the other cyclic rings can be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyl s.
  • Heterocyclyl groups include, for example, piperidine, piperazine, pyrrolidine, morpholine, lactones, lactams, and the like.
  • heterocyclylalkyl refers to an alkyl group substituted with a heterocycle group.
  • Hydrocarbyls may optionally include heteroatoms.
  • Hydrocarbyl groups include, but are not limited to, alkyl, alkenyl, alkynyl, alkoxyalkyl, aminoalkyl, aralkyl, aryl, aralkyl, carbocyclyl, cycloalkyl, carbocyclylalkyl, heteroaralkyl, heteroaryl groups bonded through a carbon atom, heterocyclyl groups bonded through a carbon atom,
  • heterocyclylakyl or hydroxyalkyl.
  • hydroxyalkyl refers to an alkyl group substituted with a hydroxy group.
  • lower when used in conjunction with a chemical moiety, such as, acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant to include groups where there are six or fewer non-hydrogen atoms in the substituent.
  • acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy substituents defined herein are respectively lower acyl, lower acyloxy, lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy, whether they appear alone or in combination with other substituents, such as in the recitations hydroxyalkyl and aralkyl (in which case, for example, the atoms within the aryl group are not counted when counting the carbon atoms in the alkyl substituent).
  • each ring of the polycycle contains from 3 to 10 atoms in the ring, preferably from 5 to 7.
  • poly(weto-phenylene oxides) refers inclusively to 6-membered aryl or 6-membered heteroaryl moieties.
  • exemplary poly(weto-phenylene oxides) are described in the first through twentieth aspects of the present disclosure.
  • sil refers to a silicon moiety with three hydrocarbyl moieties attached thereto.
  • substituted refers to moieties having substituents replacing a hydrogen on one or more carbons of the backbone. It will be understood that
  • substitution or“substituted with” includes the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound, e.g., which does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, etc.
  • Moieties that may be substituted can include any appropriate substituents described herein, for example, acyl, acylamino, acyloxy, alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylamino, alkylthio, arylthio, alkynyl, amide, amino, aminoalkyl, aralkyl, carbamate, carbocyclyl, cycloalkyl, carbocyclylalkyl, carbonate, ester, ether, heteroaralkyl, heterocyclyl, heterocyclylalkyl, hydrocarbyl, silyl, sulfone, or thioether.
  • substituents described herein for example, acyl, acylamino, acyloxy, alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylamino, alkylthio, arylthio, alkynyl, amide, amino, aminoalkyl, a
  • the term“substituted” is contemplated to include all permissible substituents of organic compounds.
  • the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and non-aromatic substituents of organic compounds.
  • the permissible substituents can be one or more and the same or different for appropriate organic compounds.
  • the heteroatoms such as nitrogen may have hydrogen and/or any permissible substituents of organic compounds described herein which satisfy the valences of the heteroatoms.
  • Substituents can include any substituents described herein, for example, a halogen, a hydroxyl, a carbonyl (such as a carboxyl, an alkoxycarbonyl, a formyl, or an acyl), a thiocarbonyl (such as a thioester, a thioacetate, or a thioformate), an alkoxy, a phosphoryl, a phosphate, a phosphonate, a phosphinate, an amino, an amido, an amidine, an imine, a cyano, a nitro, an azido, a sulfhydryl, an alkylthio, a sulfate, a sulfonate, a sulfamoyl, a sulfonamido, a sulfonyl, a heterocyclyl, an aralkyl, or an aromatic or heteroaromatic moiety
  • the substituents on substituted alkyls are selected from Ci- 6 alkyl, C3-6 cycloalkyl, halogen, carbonyl, cyano, or hydroxyl. In more preferred embodiments, the substituents on substituted alkyls are selected from fluoro, carbonyl, cyano, or hydroxyl. It will be understood by those skilled in the art that substituents can themselves be substituted, if appropriate. Unless specifically stated as “unsubstituted,” references to chemical moieties herein are understood to include substituted variants. For example, reference to an“aryl” group or moiety implicitly includes both substituted and unsubstituted variants.
  • sulfonate is art-recognized and refers to the group SO3H, or a pharmaceutically acceptable salt thereof.
  • sulfone is art-recognized and refers to the group -S(0)2-R A , wherein R A represents a hydrocarbyl.
  • thioether is equivalent to an ether, wherein the oxygen is replaced with a sulfur.
  • symmetrical molecule refers to molecules that are group symmetric or synthetic symmetric.
  • group symmetric refers to molecules that have symmetry according to the group theory of molecular symmetry.
  • synthetic symmetric refers to molecules that are selected such that no regioselective synthetic strategy is required.
  • donor refers to a molecular fragment that can be used in organic light-emitting diodes and is likely to donate electrons from its highest occupied molecular orbital to an acceptor upon excitation.
  • donors contain substituted amino groups.
  • donors have an ionization potential greater than or equal to -6.5 eV.
  • acceptor refers to a molecular fragment that can be used in organic light-emitting diodes and is likely to accept electrons into its lowest unoccupied molecular orbital from a donor that has been subject to excitation. In an example embodiment, acceptors have an electron affinity less than or equal to -0.5 eV.
  • linker refers to a molecular fragment that can be included in a molecule which is covalently linked between acceptor and donor moieties.
  • the linker can, for example, be further conjugated to the acceptor moiety, the donor moiety, or both. Without being bound to any particular theory, it is believed that the linker moiety can sterical!y restrict the acceptor and donor moieties into a specific configuration, thereby preventing the overlap between the conjugated p system of donor and acceptor moieties.
  • suitable linker moieties include phenyl, ethenyl, and ethyny!.
  • multivalent refers to a molecular fragment that is connected to at least two other molecular fragments.
  • a linker moiety is multivalent.
  • Hole transport layer I ITl. f and like terms mean a layer made from a material which transports holes. Fligh hole mobility is recommended.
  • the EITI is used to help block passage of electrons transported by the emitting layer. Low electron affinity is typically required to block electrons.
  • the EITI should desirably have larger triplets to block exciton migrations from an adjacent emisse layer (EML).
  • HTL compounds include, but are not limited to, di(p-tolyl)aminophenyl]cyclohexane (TAPC), N,N-diphenyl-N,N-bis(3- methylphenyl)-l,l-biphenyl-4, 4-diamine (TPD), and N,N diphenyl-N,N’-bis(l-naphthyl)- (1,1 '-biphenyl)-4,4'-diamine (NPB, a-NPD).
  • TAPC di(p-tolyl)aminophenyl]cyclohexane
  • TPD N,N-diphenyl-N,N-bis(3- methylphenyl)-l,l-biphenyl-4, 4-diamine
  • NBP N,N diphenyl-N,N’-bis(l-naphthyl)- (1,1 '-biphenyl)-4,4'-di
  • the emitting layer and like terms mean a layer which emits light.
  • the emitting layer comprises host material and guest material.
  • the guest material can also be referred to as a dopant material, but the disclosure is not limited there to.
  • the host material or“host” could be bipolar or unipolar, and may be used alone or by combination of two or more host materials.
  • the opto-electrical properties of the host material may differ to which type of guest material (TADF, Phosphorescent or Fluorescent) is used.
  • TADF type of guest material
  • Phosphorescent guest materials the host materials should have good spectral overlap between absorption of the guest material and emission of the material to induce good Forster transfer to guest materials.
  • the host materials should have high triplet energy to confine triplets of the guest material.
  • the host materials should have both spectral overlap and higher triplet energy.
  • Dopant refers to additive materials for carrier transporting layers, emitting layers or other layers in carrier transporting layers, dopant and like terms perform as an electron acceptor or a donator that increases the conductivity of an organic layer of an organic electronic device, when added to the organic layer as an additive.
  • Organic semiconductors may likewise he influenced, with regard to their electrical conductivity, by doping.
  • Such organic semiconducting matrix materials may be made up either of compounds with electron-donor properties or of compounds with electron - acceptor properties.
  • dopant and like terms also mean the light- emitting material which is dispersed in a matrix, for example, a host.
  • assistant dopant When a triplet harvesting material is doped into an emitting layer or contained in an adjecent layer so as to improve exciton generation efficiency, it is named as assistant dopant.
  • the content of the assistant dopant in the light-emitting layer or the adjecent layer is not particularly limited so as the triplet harvesting material improves the exciton generation efficiency.
  • the content of the assistant dopant in the light-emitting layer is preferably higher than, more preferably at least twice than the light-emitting material.
  • the content of the host material is preferably 50% by weight or more
  • the content of the assistant dopant is preferably from 5% by weight to less than 50% by weight
  • the content of the light-emitting material is preferably more than 0% by weight to less than 25% by weight, more preferably from 0% by weight to less than 10% by weight.
  • the content of the assitant dopant in the adjecent layer may be more than 50% by weight and may be 100% by weight.
  • a device containing a triplet harvesting material in a light-emitting layer or an adjecent layer has a higher light emission efficiency than a device without the triplet harvesting material, such triplet harvesting material functions as an assistant dopant.
  • a light-emitting layer containing a host material, an assistant dopant and a light-emitting material satisfies the following (A) and preferably satisfies the following (B):
  • ESI (A) represents a lowest excited singlet energy level of the host material
  • ES!(B) represents a lowest excited singlet energy level of the assistant dopant
  • ESI(C) represents a lowest excited singlet energy level of the light-emitting material
  • ET1(A) represents a lowest excited triplet energy level at 77 K of the host material
  • ET1 (B) represents a lowest excited triplet energy level at 77 K of the assistant dopant.
  • the assistant dopant has an energy difference AEst between a lowest singlet excited state and a lowest triplet excited state at 77 K of preferably 0.3 eV or less, more preferably 0 2 eV or less, still more preferably 0 1 eV or less.
  • any atom not specifically designated as a particular isotope is meant to represent any stable isotope of that atom.
  • a position is designated specifically as“H” or“hydrogen”, the position is understood to have hydrogen at its natural abundance isotopic composition.
  • a position is designated specifically as“D” or“deuterium”, the position is understood to have deuterium at an abundance that is at least 3340 times greater than the natural abundance of deuterium, which is 0.015% (i.e., at least 50.1% incorporation of deuterium).
  • Substituted with deuterium refers to the replacement of one or more hydrogen atoms with a corresponding number of deuterium atoms.
  • isotopic enrichment factor means the ratio between the isotopic abundance and the natural abundance of a specified isotope.
  • compounds of this invention have an isotopic enrichment factor for each designated deuterium atom of at least 3500 (52.5% deuterium incorporation at each designated deuterium atom), at least 4000 (60% deuterium incorporation), at least 4500 (67.5% deuterium incorporation), at least 5000 (75% deuterium), at least 5500 (82.5% deuterium incorporation), at least 6000 (90% deuterium incorporation), at least 6333.3 (95% deuterium incorporation), at least 6466.7 (97% deuterium incorporation), at least 6600 (99% deuterium incorporation), or at least 6633.3 (99.5% deuterium incorporation).
  • isotopologue refers to a species that differs from a specific compound of this invention only in the isotopic composition thereof.
  • a compound represented by a particular chemical structure containing indicated deuterium atoms will also contain lesser amounts of isotopologues having hydrogen atoms at one or more of the designated deuterium positions in that structure.
  • the relative amount of such isotopologues in a compound of this invention will depend upon a number of factors including the isotopic purity of deuterated reagents used to make the compound and the efficiency of incorporation of deuterium in the various synthesis steps used to prepare the compound.
  • the relative amount of such isotopologues in toto will be less than 49.9% of the compound. In other embodiments, the relative amount of such isotopologues in iota will be less than 47.5%, less than 40%, less than 32.5%, less than 25%, less than 17.5%, less than 10% , less than 5%, less than 3%, less than 1%, or less than 0.5% of the compound.
  • OLEDs are typically composed of a layer of organic materials or compounds between two electrodes, an anode and a cathode.
  • the organic molecules are electrically conductive as a result of delocalization of p electronics caused by conjugation over parl or all of the molecule.
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • Removal of electrons from the HOMO is also referred to as inserting electron holes into the HOMO. Electrostatic forces bring the electrons and the holes towards each other until they recombine and form an exciton (which is the bound state of the electron and the hole).
  • an exciton may either be in a singlet state or a triplet state depending on how the spins of the electron and hole have been combined. Statistically, three triplet excitons will be formed for each singlet exciton. Decay from triplet states is spin forbidden, which results in increases in the timescale of the transition and limits the internal efficiency of fluorescent devices.
  • Phosphorescent organic light-emitting diodes make use of spin-orbit interactions to facilitate intersystem crossing between singlet and triplet states, thus obtaining emission from both singlet and triplet states and improving the internal efficiency.
  • One prototypical phosphorescent material is iridium tris(2-phenylpyridine) (Ir(ppy)3) in which the excited state is a charge transfer from the Ir atom to the organic ligand.
  • Ir(ppy)3 iridium tris(2-phenylpyridine)
  • Such approaches have reduced the triplet lifetime to about several ps, several orders of magnitude slower than the radiative lifetimes of fully -allowed transitions such as fluorescence.
  • Ir-based phosphors have proven to be acceptable for many display applications, but losses due to large triplet densities still prevent the application of OLEDs to solid-state lighting at higher brightness.
  • TADF seeks to minimize AEST.
  • the reduction in exchange splitting from typical values of 0.4-0.7 eV to a gap of the order of the thermal energy (proportional to kBT, where kB represents the Boltzmann constant, and T represents temperature) means that thermal agitation can transfer population between singlet levels and triplet sublevels in a relevant timescale even if the coupling between states is small.
  • TADF molecules consist of donor and acceptor moieties connected directly by a covalent bond or via a conjugated linker (or "bridge”).
  • a "donor” moiety is likely to transfer electrons from its HOMO upon excitation to the "acceptor” moiety.
  • acceptor moiety is likely to accept the electrons from the "donor” moiety into its LUMO.
  • the donor-acceptor nature of TADF molecules results in low-lying excited states with charge-transfer character that exhibit very low AEST. Since thermal molecular motions can randomly vary the optical properties of donor-acceptor systems, a rigid three-dimensional arrangement of donor and acceptor moieties can be used to limit the non-radiative decay of the charge-transfer state by internal conversion during the lifetime of the excitation.
  • the compounds of the invention have a structure of
  • D is independently selected from
  • P and P’ are independently selected from H, deuterium,
  • At least one instance of P is selected from Pl to P23;
  • X and X’ are independently selected from C(H), and N;
  • Y is independently selected from C and Si;
  • Z is independently selected from S, O, and N(Ph).
  • D is Dl. In some embodiments, D is D2. In some embodiments, D is D3. In some embodiments, D is D4. In some embodiments, D is D5. In some embodiments, D is D6. In some embodiments, D is D7. In some embodiments, D is D8. In some embodiments, D is D9. In some embodiments, D is D10. In some embodiments, D is Dl l. In some embodiments, D is D12. In some embodiments, D is D13. In some embodiments, D is D14. In some embodiments, D is D15. In some embodiments, D is D 16. In some embodiments, D is D 17. In some embodiments, D is D18. In some embodiments, D is D19.
  • D is D20. In some embodiments, D is D21. In some embodiments, D is D22. In some embodiments, D is D23. In some embodiments, D is D24. In some embodiments, D is D25. In some embodiments, D is D26. In some embodiments, D is D27. In some embodiments, D is D28. In some embodiments, D is D29.
  • D is selected from Dl, D2, D3, D4, D5, D6, and D7.
  • D is selected from D8, D9, D10, Dl l, D12, and Dl3.
  • D is selected from D14, D15, and D16.
  • D is selected from D17, D18, and D19.
  • D is selected from D20, D21, D22, D23, and D24.
  • D is selected from D25, D26, and D27.
  • D is selected from D28 and D29.
  • Z is S. In some embodiments, Z is O. In some
  • Z is N(Ph).
  • P is H or deuterium.
  • P is selected from Pl, P2, P3, P4, and P5.
  • P is selected from P6, P7, and P8.
  • P is selected from P9, P10, Pl 1, and P12.
  • P is selected from P13, P14, P15, and P16.
  • P is selected from P17, P18, and P19.
  • P is selected from P20, P21, P22, and P23.
  • P’ is H or deuterium. In some embodiments, P’ is selected from Pl, P2, P3, P4, and P5. In some embodiments, P’ is selected from P6, P7, and P8.
  • P’ is selected from P9, P10, Pl 1, and P12. In some embodiments, P’ is selected from P13, P14, P15, and P16. In some embodiments, P’ is selected from P17, P18, and P19. In some embodiments, P’ is selected from P20, P21, P22, and P23.
  • X is C(H). In some embodiments, all instances of X are C(H). In some embodiments, X is N. In some embodiments, one instance of X is N.
  • X’ is C(H). In some embodiments, all instances of X’ are
  • X’ is N. In some embodiments, one instance of X’ is N.
  • Y is C. In some embodiments, Y is Si.
  • the compound of Formula (I) or (II) is selected from
  • the compound of Formula (I) or (II) is selected from
  • the compound of Formula (I) or (II) is In some embodiments, the compound of Formula (I) or (II) is
  • the compound is a compound of Formula (I) or
  • D is independently selected from
  • P and P’ are independently selected from H, deuterium,
  • X and X’ are C(R);
  • R is independently is independently H, deuterium, Ci-4-alkyl, C6-12- aryl, or C5-12- heteroaryl.
  • the compounds are of Formula (I). In some embodiments, the compounds are of Formula (II). In some embodiments, D is Dl. In some embodiments, D is D2. In some embodiments, D is D3. In some embodiments, D is D4. In some embodiments, D is D5. In some embodiments, D is D17. In some embodiments, D is D18. In some
  • D is D20. In some embodiments, D is D21. In some embodiments, D is D22. In some embodiments, D is D23. In some embodiments, D is D28. In some embodiments, D is D29.
  • D is selected from D2, and D3. In some embodiments, D is selected from D4, and D5. In some embodiments, D is selected from D17, and D18. In some embodiments, D is selected from D20, D21, D22, and D23. In some embodiments, D is selected from D28 and D29.
  • P is H. In some embodiments, P is deuterium. In some embodiments, P is Pl. In some embodiments, P is P2. In some embodiments, P is P3. In some embodiments, P is P4. In some embodiments, P is P5. In some embodiments, P is P5. In some embodiments, P is P6. In some embodiments, P is P7. In some
  • P is P8.
  • P is selected from Pl, and P2. In some embodiments, P is selected from P3, P4, P5, P6, P7, and P8. In some embodiments, R is alkyl. In some embodiments, R is Me. In some embodiments, R is t-butyl.
  • only one instance of P is P2. In some embodiments, both instances of P are P2. In some embodiments, only one instance of P’ is P2. In some embodiments, both instances of P’ are P2. In some embodiments, one instance of D is Dl. In some embodiments, both instances of D are Dl. In some embodiments, one instance of D is D3. In some embodiments, both instances of D are D3. In some embodiments, one instance of D is D4. In some embodiments, both instances of D are D4. In some embodiments, one instance of D is D27. In some embodiments, both instances of D are D27. In some embodiments, the compound of Formula (II) is
  • the compound of Formula (II) is selected from:
  • the compound of Formula (II) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-N-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the compound of Formula (II) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N
  • the compound of Formula (I) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the compound of Formula (II) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • compound of Formula (II) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-N-phenyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoe
  • the compound of Formula (I) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the compound of Formula (I) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • compounds of Formula (I) or (II) are substituted with deuterium. In some embodiments, compounds of Formula (I) or (II) are light-emitting materials.
  • compounds of Formula (I) or (II) are capable of emitting delayed fluorescence.
  • the compounds of Formula (I) or (IT) when excited via thermal or electronic means, can produce light in ultraviolet region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 mn to about 700 nm), or near-infrared region.
  • the compounds of Formula (I) or (II) when excited via thermal or electronic means, can produce light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm; about 650 nm).
  • the compounds of Formula (I) or (II) when excited via thermal or electronic means, can produce light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 n ; about 590 nm; about 570 nm).
  • the compounds of Formula (I) or (II) when excited via thermal or electronic means, can produce light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm; about 510 nm).
  • the compounds of Formula (I) or (II) when excited via thermal or electronic means, can produce light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm; about 475 nm).
  • Electronic properties of a library of small chemical molecules can be computed using known ab initio quantum mechanical computations. For example, using a time- dependent density functional theory using, as a basis set, the set of functions known as 6- 3 IG* and a Becke, 3-parameter, Lee- Yang-Parr hybrid functional to solve ITartree-Fock equations (TD-DFT/B3LYP/6-31G*), molecular fragments (moieties) can be screened which have HOMOs above a specific threshold and LUMOs below a specific threshold, and wherein the calculated triplet state of the moieties is above 2.75 eV.
  • a donor moiety (“D”) can be selected because it has a HOMO energy (e.g., an ionization potential) of greater than or equal to -6.5 eV.
  • An acceptor moiety (“A”) can be selected because it has, for example, a LEIMO energy (e.g., an electron affinity) of less than or equal to -0.5 eV.
  • the linker moiety (“L”) can be a rigid conjugated system which can, for example, sterically restrict the acceptor and donor moieties into a specific configuration, thereby preventing the overlap between the conjugated p system of donor and acceptor moieties.
  • the compound library is filtered using one or more of the following properties:
  • the difference between the lowest singlet excited state and the lowest triplet excited state at 77K is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, the AEST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV.
  • a compound of Formula (I) or (II) exhibits a quantum yield of greater than 25%, such as about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or greater.
  • a compound of Formula (I) or (II) is combined with, dispersed within, covalently bonded to, coated with, formed on, or otherwise associated with, one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) to form a film or layer in solid state.
  • the compound of Formula (I) or (II) may be combined with an electroactive material to form a film.
  • the compound of Formula (I) or (II) may be combined with a hole-transport polymer.
  • the compound of Formula (I) or (II) may be combined with an electron- transport polymer.
  • the compound of Formula (I) or (II) may be combined with a hole-transport polymer and an electron-transport polymer. In some cases, the compound of Formula (I) or (II) may be combined with a copolymer comprising both hole-transport portions and electron-transport portions. In such embodiments, electrons and/or holes formed within the solid film or layer may interact with the compound of Formula (I) or (II).
  • One aspect of the invention relates to use of the compound of Formula (I) or (II) of the invention as a light-emitting material of an organic light-emitting device.
  • the compound represented by the Formula (I) or (II) of the invention may be effectively used as a light-emitting material in a light-emitting layer of an organic light- emitting device.
  • the compound of Formula (I) or (II) comprises a delayed fluorescent material emitting delayed fluorescent light (delayed fluorescence emitter).
  • the invention provides a delayed fluorescence emitter having the structure of Formula (I) or (II).
  • the invention relates to the use of the compound of Formula (I) or (II) as the delayed fluorescence emitter.
  • the light-emitting layer comprises a compound of Formula (I) or (II) as an assist dopant.
  • the compound of Formula ( I) or (II) can be used as a host material and used with one or more light-emitting materials, and the light-emitting material can be a fluorescent material, a phosphorescent materia! or a TADF material.
  • the compound of Formula (I) or (II) can be used as a hole transport material.
  • the compound of Formula (I) or (II) can be used as an electron transport material.
  • the invention relates to a method for emitting delayed fluorescent light from the compound of Formula (I) or (II)
  • an organic light-emitting device comprising the compound as a light- emitting material, emits delayed fluorescent light, and has a high light emission efficiency.
  • a light-emitting layer comprises a compound of Formula (I) or (II), wherein the compound of Formula (I) or (II) is oriented parallel to the substrate.
  • the substrate is a film forming surface.
  • the orientation of the compound of Formula (I) or (II) with respect to the film forming surface influences or determines the propagation directions of the light emitted by the compound to be aligned.
  • the alignment of the propagation directions of the light emitted by the compound of Formula (I) or (II) enhances the light extraction efficiency from the light-emitting layer.
  • the organic light-emitting device comprises a light-emitting layer.
  • the light-emitting layer comprises a compound of Formula (I) or (II) as a light-emitting material.
  • the organic light-emitting device is an organic photoluminescent device (organic PL device).
  • the organic light-emitting device is an organic electroluminescent device (organic EL device).
  • the compound of Formula (I) or (II) assists the light emission of another light-emitting material comprised in the light-emitting layer, i.e., as a so-called assistant dopant.
  • the compound of Formula (I) or (II) comprised in the light-emitting layer is in its the lowest excited singlet energy level, which is comprised between the lowest excited singlet energy level of the host material comprised in the light-emitting layer and the lowest excited singlet energy level of another light-emitting material comprised in the light-emitting layer.
  • the organic photoluminescent device comprises at least one light-emitting layer.
  • the organic electroluminescent device comprises at least an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic layer comprises at least a light-emitting layer.
  • the organic layer comprises only a light-emitting layer.
  • the organic layer comprises one or more organic layers in addition to the light-emitting layer. Examples of the organic layer include a hole transporting layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transporting layer and an exciton barrier layer.
  • the hole transporting layer may be a hole injection and transporting layer having a hole injection function
  • the electron transporting layer may be an electron injection and transporting layer having an electron injection function.
  • An example of an organic electroluminescent device is shown in Fig. 1.
  • the organic electroluminescent device of the invention is supported by a substrate, wherein the substrate is not particularly limited and may be any of those that have been commonly used in an organic electroluminescent device, for example those formed of glass, transparent plastics, quartz and silicon.
  • the anode of the organic electroluminescent device is made of a metal, an alloy, an electroconductive compound, or a combination thereof.
  • the metal, alloy, or electroconductive compound has a large work function (4 eV or more).
  • the metal is Au.
  • the electroconductive transparent material is selected from Cul, indium tin oxide (ITO), S11O2, and ZnO.
  • an amorphous material capable of forming a transparent electroconductive film such as IDIXO (I Cb-ZnO), is be used.
  • the anode is a thin film.
  • the thin film is made by vapor deposition or sputtering.
  • the film is patterned by a photolithography method.
  • the pattern may not require high accuracy (for example, approximately 100 pm or more)
  • the pattern may be formed with a mask having a desired shape on vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method and a coating method is used.
  • the anode when the emitted light goes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred Ohm per square or less.
  • the thickness of the anode is from 10 to 1,000 nm. In some embodiments, the thickness of the anode is from 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.
  • the cathode is made of an electrode material a metal having a small work function (4 eV or less) (referred to as an electron injection metal), an alloy, an electroconductive compound, or a combination thereof.
  • an electrode material a metal having a small work function (4 eV or less) (referred to as an electron injection metal), an alloy, an electroconductive compound, or a combination thereof.
  • the electrode material is selected from sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-cupper mixture, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (AI2O3) mixture, indium, a lithium-aluminum mixture, and a rare earth metal.
  • a mixture of an electron injection metal and a second metal that is a stable metal having a larger work function than the electron injection metal is used.
  • the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (AI2O3) mixture, a lithium-aluminum mixture, and aluminium.
  • the mixture increases the electron injection property and the durability against oxidation.
  • the cathode is produced by forming the electrode material into a thin film by vapor deposition or sputtering.
  • the cathode has a sheet resistance of several hundred Ohm per square or less. In some embodiments, the thickness of the cathode ranges from 10 nm to 5 pm. In some embodiments, the thickness of the cathode ranges from 50 to 200 nm. In some embodiments, for transmitting the emitted light, any one of the anode and the cathode of the organic electroluminescent device is transparent or translucent. In some
  • the transparent or translucent electroluminescent devices enhances the light emission luminance.
  • the cathode is formed with an electroconductive transparent material, as described for the anode, to form a transparent or translucent cathode.
  • a device comprises an anode and a cathode, both being transparent or translucent.
  • the light-emitting layer is a layer, in which holes and electrons, injected respectively from the anode and the cathode, are recombined to form excitons. In some embodiments, the layer emits light.
  • a light-emitting material is solely used as the light- emitting layer.
  • the light-emitting layer contains a light-emitting material, and a host material.
  • the light-emitting material is one or more compounds of Formula (I) or (II).
  • the singlet excitons and the triplet excitons generated in the light-emitting material are confined in the light-emitting material.
  • a host material is used in addition to the light-emitting material in the light-emitting layer.
  • the host material is an organic compound.
  • the orgamic compounds have excited singlet energy and excited triplet energy, at least one of which is higher than those of the light-emitting material of the invention.
  • the singlet excitons and the triplet excitons generated in the light-emitting material of the invention are confined in the molecules of the light-emitting material of the invention.
  • the singlet and triplet excitons are sufficiently confined to elicit the light emission efficiency.
  • the singlet excitons and the triplet excitons are not confined sufficiently, though a high light emission efficiency is still obtained, and thus a host material capable of achieving a high light emission efficiency can be used in the invention without any particular limitation.
  • the light emission occurs in the light- emitting material of the light-emitting layer in the devices of the invention.
  • the emitted light contains both fluorescent light and delayed fluorescent light.
  • the emitted light comprises emitted light from the host material.
  • the emitted light consists of emitted light from the host material.
  • the emitted light light comprises emitted light from a compound of Formula (I) or (II), and emitted light from the host material.
  • a TADF molecule and a host material are used.
  • the TADF is an assistant dopant.
  • the amount of the compound of the invention as the light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the invention as the light-emitting material contained in the light- emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the invention as the light-emitting material contained in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the invention as the light- emitting material contained in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the invention as the light-emitting material contained in the light-emitting layer is 10% by weight or less.
  • the host material in the light-emitting layer is an organic compound comprising a hole transporting function and an electron transporting function. In some embodiments, the host material in the light-emitting layer is an organic compound that prevents the emitted light from being increased in wavelength. In some embodiments, the host material in the light-emitting layer is an organic compound with a high glass transition temperature.
  • the host material is selected from the group consisting of:
  • An injection layer is a layer between the electrode and the organic layer.
  • the injection layer decreases the driving voltage and enhances the light emission luminance.
  • the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be positioned between the anode and the light-emitting layer or the hole transporting layer, and between the cathode and the light-emitting layer or the electron transporting layer.
  • an injection layer is present. In some embodiments, no injection layer is present.
  • a barrier layer is a layer capable of inhibiting charges (electrons or holes) and/or excitons present in the light-emitting layer from being diffused outside the light-emitting layer.
  • the electron barrier layer is between the light-emitting layer and the hole transporting layer, and inhibits electrons from passing through the light-emitting layer toward the hole transporting layer.
  • the hole barrier layer is between the light-emitting layer and the electron transporting layer, and inhibits holes from passing through the light-emitting layer toward the electron transporting layer.
  • the barrier layer inhibits excitons from being diffused outside the light-emitting layer.
  • the electron barrier layer and the hole barrier layer are exciton barrier layers.
  • the term "electron barrier layer" or "exciton barrier layer” includes a layer that has the functions of both electron barrier layer and of an exciton barrier layer.
  • a hole barrier layer acts as an electron transporting layer.
  • the hole barrier layer inhibits holes from reaching the electron transporting layer while transporting electrons.
  • the hole barrier layer enhances the recombination probability of electrons and holes in the light-emitting layer.
  • the material for the hole barrier layer may be the same materials as the ones described for the electron transporting layer.
  • the electron barrier layer transports holes.
  • the electron barrier layer inhibits electrons from reaching the hole transporting layer while transporting holes.
  • the electron barrier layer enhances the recombination probability of electrons and holes in the light-emitting layer.
  • An exciton barrier layer inhibits excitons generated through recombination of holes and electrons in the light-emitting layer from being diffused to the charge transporting layer.
  • the exciton barrier layer enables effective confinement of excitons in the light-emitting layer.
  • the light emission efficiency of the device is enhanced.
  • the exciton barrier layer is adjacent to the light-emitting layer on any of the side of the anode and the side of the cathode, and on both the sides. In some embodiments, where the exciton barrier layer is on the side of the anode, the layer can be between the hole transporting layer and the light-emitting layer and adjacent to the light-emitting layer.
  • the layer can be between the light-emitting layer and the cathode and adjacent to the light-emitting layer.
  • a hole injection layer, an electron barrier layer, or a similar layer is between the anode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the anode.
  • a hole injection layer, an electron barrier layer, a hole barrier layer, or a similar layer is between the cathode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the cathode.
  • the exciton barrier layer comprises excited singlet energy and excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy of the light-emitting material, respectively.
  • the hole transporting layer comprises a hole transporting material.
  • the hole transporting layer is a single layer.
  • the hole transporting layer comprises a plurality of layers.
  • the hole transporting material has one of injection or transporting property of holes and barrier property of electrons.
  • the hole transporting material is an organic material.
  • the hole transporting material is an inorganic material. Examples of known hole transporting materials that may be used herein include but are not limited to a triazole derivative, an oxadiazole derivative, an imidazole derivative, a carbazole derivative, an
  • indolocarbazole derivative a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, an oxazole derivative, a styrylanthracene derivative, a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aniline copolymer and an electroconductive polymer oligomer, particularly a thiophene oligomer, or a combination thereof.
  • the hole transporting material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transporting material is an aromatic tertiary amine compound.
  • a hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound.
  • the hole transporting material is an aromatic tertiary amine compound.
  • the electron transporting layer comprises an electron transporting material.
  • the electron transporting layer is a single layer. In some
  • the electron transporting layer comprises a plurality of layer.
  • the electron transporting material needs only to have a function of transporting electrons, which are injected from the cathode, to the light- emitting layer.
  • the electron transporting material also function as a hole barrier material. Examples of the electron transporting layer that may be used herein include but are not limited to a nitro- substituted fluorene derivative, a
  • diphenylquinone derivative a thiopyran dioxide derivative, carbodiimide, a
  • the electron transporting material is a thiadiazole derivative, or a quinoxaline derivative.
  • the electron transporting material is a polymer material.
  • the molecular weight of the compound represented by the Formula (I) or (II) is, for example, in the case of using it by forming an organic layer that contains a compound represented by the Formula (I) or (II) according to a vapor deposition method, preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, still more preferably 900 or less.
  • Compounds of Formula (I) or (II) may be formed into a film according to a coating method irrespective of the molecular weight of the compound. Accordingly, even a compound having a relatively large molecular weight can be formed into a film.
  • a film comprises a plurality of independently selected compounds of Formula (I) or (II).
  • a compound of Formula (I) or (II) is modified to incorporate a polymerizable group.
  • the modified compound is then polymerized to obtain a polymer comprising a compound of Formula (I) or (II).
  • a monomer is obtained by replacing any one of the hydrogen of a compound of Formula (I) or (II) by a polymerizable functional group.
  • the monomer is then homo- polymerized or copolymerized with any other monomer to give a polymer having a repeating unit.
  • different compounds of Formula (I) or (II) are coupled to give a dimer or a trimer.
  • Examples of the polymer having a repeating unit comprising a compound of Formula (I) or (II) include polymers comprising a unit of Formula (A) or
  • Q represents a group containing a compound of Formula (I) or (II);
  • L 1 and L 2 each represents a linking group
  • R 101 , R 102 , R 103 and R 104 each independently represent a substituent.
  • the linking group is preferably 0 to 20 carbons, more preferably 1 to 15, even more preferably 2 to 10. In some embodiments, the linking is - X u -L u -; wherein X 11 is oxygen or sulphur, and L 11 represents a linking group.
  • X 11 is oxygen.
  • L 11 is a substituted or unsubstituted alkylene or a substituted or unsubstituted arylene.
  • the substituted or unsubstituted alkylene is Cl to C10 alkylene.
  • substituted or unsubstituted arylene is substituted or unsubstituted phenylene.
  • R 101 , R 102 , R 103 and R 104 are independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom. In some embodiments,
  • R 101 , R 102 , R 103 and R 104 are independently unsubstituted alkyl having 1 to 3 carbon atoms, an unsubstituted alkoxy having 1 to 3 carbon atoms, a fluorine atom or a chlorine atom.
  • R 101 , R 102 , R 103 and R 104 are independently unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy 5 group having 1 to 3 carbon atoms.
  • L 1 and L 2 may be introduced by replacing any one of the hydrogen in the structure of the Formula (I) or (II). Two or more linking groups may bond to one Q to form a crosslinked structure or a network structure.
  • repeating unit examples include structures represented by the following Formulae (C) to (F).
  • Polymers having a repeating unit of the Formulae (C) to (F) may be synthesized by replacing any one of the hydrogen by a hydroxy group into a structure of the Formula (I) or (II), then introducing a polymerizable group into the structure through reaction with any of the following compounds via the hydroxy group serving as a linker, and polymerizing the polymerizable group.
  • the polymer having a structure represented by the Formula (I) or (II) may be a polymer containing a repeating unit alone having a structure represented by the Formula (I) or (II) or may be a polymer containing a repeating unit having any other structure.
  • the repeating unit having a structure represented by the Formula (I) or (II) contained in the polymer may be one type alone or may contain two or more types of repeating units.
  • a repeating unit not having a structure represented by the Formula (I) or (II) includes those derived from monomers to be used in ordinary copolymerization. For example, there are mentioned repeating units derived from monomers having an ethylenic unsaturated bond such as ethylene, styrene, etc.
  • a compound of Formula (I) or (II) is comprised in the light-emitting layer of a device of the invention. In some embodiments, a compound of Formula (I) or (II) is comprised in the light-emitting layer and at least one other layers. In some embodiments, the compounds of Formula (I) or (II) are independently selected for each layers. In some embodiments, the compounds of Formula (I) or (II) are the same. In some embodiments, the compounds of Formula (I) or (II) are different.
  • the compound represented by the Formula (I) or (II) may be used in the injection layer, the barrier layer, the hole barrier layer, the electron barrier layer, the exciton barrier layer, the hole transporting layer, the electron transporting layer and the like described above.
  • the film forming method of the layers are not particularly limited, and the layers may be produced by any dry processes and/or wet processes. Specific examples of materials that can be used in the organic electroluminescent device are shown above, but the materials that may be used in the invention are not construed as being limited to the example compounds. In some embodiments, a material having a particular function can also have another function.
  • the compound of the invention may be formed as a film on a substrate by any methods.
  • the substrate Before forming the film, the substrate may be heated or cooled, and the film quality and the molecular packing in the film may be controlled by changing the temperature of the substrate.
  • the temperature of the substrate is not particularly limited, and is preferably in a range of 0 to 200° C, more preferably in a range of 15 to 100° C, and particularly preferably in a range of 20 to 95° C.
  • the film Before forming a film of the compound of the invention on a substrate, the film may be formed by a vacuum process or a solution process, both of which are preferred.
  • the film formation by a vacuum process include a physical vapor deposition, such as vacuum deposition, sputtering method, ion plating method and molecular beam epitaxy (MBE), and chemical vapor deposition (CVD), such as plasma polymerization, and vacuum deposition is preferably used.
  • a physical vapor deposition such as vacuum deposition, sputtering method, ion plating method and molecular beam epitaxy (MBE), and chemical vapor deposition (CVD), such as plasma polymerization, and vacuum deposition is preferably used.
  • the film formation by a solution process means a method, in which an organic compound is dissolved in a solvent capable of dissolving the same, and a film is formed by using the resulting solution.
  • a coating method such as a casting method, a dip coating method, a die coater method, a roll coater method, a bar coater method and a spin coating method
  • a printing method such as ink-jet method, screen printing method, gravure printing method, flexography printing method, offset printing method and microcontact printing method, and Langmuir-Blodgett (LB) method
  • spin-coating method preferably ink-jet method, gravure printing method, flexography printing method, offset printing method and microcontact printing method are used.
  • the material for forming the layer may be dissolved or dispersed in a suitable organic solvent (for example, a hydrocarbon solvent, such as hexane, octane, decane, toluene, xylene, mesitylene, ethylbenzene, decalin and l-methylnaphthalene, a ketone solvent, such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, a halogenated hydrocarbon solvent, such as dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, di chlorobenzene and chlorotoluene, an ester solvent, such as ethyl acetate, butyl acetate and amy
  • a suitable organic solvent for example, a hydrocarbon solvent, such
  • a coating liquid which may be then coated by various coating methods to form the thin film.
  • a nitrile solvent such as acetonitrile
  • the compounds of the disclosure are incorporated into a device.
  • the device includes, but is not limited to an OLED bulb, an OLED lamp, a television screen, a computer monitor, a mobile phone, and a tablet.
  • an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises
  • the light-emitting layer comprises a compound of Formula (I) or (II) as a light-emitting material.
  • the light-emitting layer comprises a compound of Formula (I) or (II) as an assist dopant.
  • the light-emitting layer of the OLED further comprises a fluorescent material wherein the compound of Formula (I) or (II) converts triplets to singlets for the fluorescent emitter.
  • compositions described herein may be incorporated into various light-sensitive or light-activated devices, such as a OLEDs or photovoltaic devices.
  • the composition may be useful in facilitating charge transfer or energy transfer within a device and/or as a hole-transport material.
  • the device may be, for example, an organic light-emitting diode (QLED), an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thi -film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quench device (G- FQD), a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser).
  • QLED organic light-emitting diode
  • O-IC organic integrated circuit
  • O-FET organic field-effect transistor
  • O-TFT organic thi -film transistor
  • O-LET organic light-emitting transistor
  • O-SC organic solar cell
  • an organic optical detector an organic photoreceptor
  • G- FQD organic field-quench device
  • LEC light-emitting electrochemical cell
  • O-laser organic laser diode
  • an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises
  • the light-emitting layer comprises a compound of Formula (I) or (II) as an assist dopant.
  • a device comprises OLEDs that differ in color.
  • a device comprises an array comprising a combination of OLEDs.
  • the combination of OLEDs is a combination of three colors (e.g., RGB).
  • the combination of OLEDs is a combination of colors that are not red, green, or blue (for example, orange and yellow green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors.
  • a device is an OLED light comprising:
  • circuit board having a first side with a mounting surface and an opposing second side, and defining at least one aperture
  • At least one OLED on the mounting surface the at least one OLED configured to emanate light, comprising:
  • an anode an anode, a cathode, and at least one organic layer comprising a light- emitting layer between the anode and the cathode, wherein the light-emitting layer comprises
  • the compound of Formula (I) or (II) is a light-emitting material; a housing for the circuit board;
  • At least one connector arranged at an end of the housing, the housing and the connector defining a package adapted for installation in a light fixture.
  • the light-emitting layer comprises a compound of Formula (I) or (II) as an assist dopant.
  • the OLED light comprises a plurality of OLEDs mounted on a circuit board such that light emanates in a plurality of directions. In some embodiments, a portion of the light emanated in a first direction is deflected to emanate in a second direction. In some embodiments, a reflector is used to deflect the light emanated in a first direction.
  • the compounds of Formula (I) or (II) can be used in a screen or a display.
  • the compounds of Formula (I) or (II) are deposited onto a substrate using a process including, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in a two-sided etch provides a unique aspect ratio pixel.
  • the screen (which may also be referred to as a mask) is used in a process in the manufacturing of OLED displays.
  • the corresponding artwork pattern design facilitates a very steep and narrow tie-bar between the pixels in the vertical direction and a large, sweeping bevel opening in the horizontal direction. This allows the close patterning of pixels needed for high definition displays while optimizing the chemical deposition onto a TFT backplane.
  • the internal patterning of the pixel allows the construction of a 3-dimensional pixel opening with varying aspect ratios in the horizontal and vertical directions.
  • imaged“stripes” or halftone circles within the pixel area inhibits etching in specific areas until these specific patterns are undercut and fall off the substrate. At that point the entire pixel area is subjected to a similar etch rate but the depths are varying depending on the halftone pattern. Varying the size and spacing of the halftone pattern allows etching to be inhibited at different rates within the pixel allowing for a localized deeper etch needed to create steep vertical bevels.
  • a preferred material for the deposition mask is invar.
  • Invar is a metal alloy that is cold rolled into long thin sheet in a steel mill. Invar cannot be electrodeposited onto a rotating mandrel as the nickel mask.
  • a preferred and more cost feasible method for forming the open areas in the mask used for deposition is through a wet chemical etching.
  • a screen or display pattern is a pixel matrix on a substrate.
  • a screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).
  • a screen or display pattern is fabricated using a wet chemical etch.
  • a screen or display pattern is fabricated using plasma etching.
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel in units of cell panels.
  • each of the cell panels on the mother panel is formed by forming a thin film transistor (TFT) including an active layer and a source/drain electrode on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then is cut from the mother panel.
  • TFT thin film transistor
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel in units of cell panels.
  • each of the cell panels on the mother panel is formed by forming a thin film transistor (TFT) including an active layer and a source/drain electrode on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then is cut from the mother panel.
  • TFT thin film transistor
  • OLED organic light- emitting diode
  • the barrier layer is an inorganic film formed of, for example, SiNx, and an edge portion of the barrier layer is covered with an organic film formed of polyimide or acryl.
  • the organic film helps the mother panel to be softly cut in units of the cell panel.
  • the thin film transistor (TFT) layer includes a light- emitting layer, a gate electrode, and a source/drain electrode.
  • Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein the organic film applied to the interface portion is formed of a same material as a material of the planarization film and is formed at a same time as the planarization film is formed.
  • a light-emitting unit is connected to the TFT layer with a passivation layer and a planarization film therebetween and an encapsulation layer that covers and protects the light-emitting unit.
  • the organic film contacts neither the display units nor the encapsulation layer.
  • Each of the organic film and the planarization film may include any one of polyimide and acryl.
  • the barrier layer may be an inorganic film.
  • the base substrate may be formed of polyimide.
  • the method may further include, before the forming of the barrier layer on one surface of the base substrate formed of polyimide, attaching a carrier substrate formed of a glass material to another surface of the base substrate, and before the cutting along the interface portion, separating the carrier substrate from the base substrate.
  • the OLED display is a flexible display.
  • the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer.
  • the planarization film is an organic film formed on the passivation layer.
  • the planarization film is formed of polyimide or acryl, like the organic film formed on the edge portion of the barrier layer.
  • the planarization film and the organic film are simultaneously formed when the OLED display is manufactured.
  • the organic film may be formed on the edge portion of the barrier layer such that a portion of the organic film directly contacts the base substrate and a remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.
  • the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode.
  • the pixel electrode is connected to the source/drain electrode of the TFT layer.
  • an image forming unit including the TFT layer and the light- emitting unit is referred to as a display unit.
  • the encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed to have a thin film
  • the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are stacked.
  • the organic film applied to the interface portion is spaced apart from each of the plurality of display units.
  • the organic film is formed such that a portion of the organic film directly contacts the base substrate and a remaining portion of the organic film contacts the barrier layer while surrounding an edge portion of the barrier layer.
  • the OLED display is flexible and uses the soft base substrate formed of polyimide.
  • the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.
  • the barrier layer is formed on a surface of the base substrate opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to a size of each of the cell panels. For example, while the base substrate is formed over the entire surface of a mother panel, the barrier layer is formed according to a size of each of the cell panels, and thus a groove is formed at an interface portion between the barrier layers of the cell panels. Each of the cell panels can be cut along the groove.
  • the method of manufacture further comprises cutting along the interface portion, wherein a groove is formed in the barrier layer, wherein at least a portion of the organic film is formed in the groove, and wherein the groove does not penetrate into the base substrate.
  • the TFT layer of each of the cell panels is formed, and the passivation layer which is an inorganic film and the planarization film which is an organic film are disposed on the TFT layer to cover the TFT layer.
  • the planarization film formed of, for example, poiyimide or aery! is formed, the groove at the interface portion is covered with the organic film formed of, for example, poiyimide or acryl.
  • each of the cell panels may be softly cut and cracks may be prevented from occurring in the barrier layer.
  • the organic film covering the groove at the interface portion and the planarization film are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, since external moisture may penetrate into the display unit through the
  • the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.
  • the display unit is formed by forming the light-emitting unit and the encapsulation layer is disposed on the display unit to cover the display unit.
  • the carrier substrate that supports the base substrate is separated from the base substrate.
  • the carrier substrate is separated from the base substrate due to a difference in a thermal expansion coefficient between the carrier substrate and the base substrate.
  • the mother panel is cut in units of the cell panels. In some embodiments, the mother panel is cut along an interface portion between the cell panels by using a cutter. In some embodiments, since the groove at the interface portion along which the mother panel is cut is covered with the organic film, the organic film absorbs an impact during the cutting. In some embodiments, cracks may be prevented from occurring in the barrier layer during the cutting.
  • the methods reduce a defect rate of a product and stabilize
  • an OLED display including: a barrier layer that is formed on a base substrate, a display unit that is formed on the barrier layer; an encapsulation layer that is formed on the display unit; and an organic film that is applied to an edge portion of the barrier layer.
  • An embodiment of the present disclosure provides the preparation of compounds of Formula (I) or (II) or (II) according to the procedures of the following example(s), using appropriate materials. Those skilled in the art will understand that known variations of the conditions and processes of the following preparative procedures can be used to prepare these compounds. Moreover, by utilizing the procedures described in detail, one of ordinary skill in the art can prepare additional compounds of the present disclosure.
  • an organic electroluminescent device carriers are injected from an anode and a cathode to a light-emitting material to form an excited state for the light-emitting material, with which light is emitted.
  • a carrier injection type organic electroluminescent device in general, excitons that are excited to the excited singlet state are 25% of the total excitons generated, and the remaining 75% thereof are excited to the excited triplet state. Accordingly, the use of phosphorescence, which is light emission from the excited triplet state, provides a high energy utilization.
  • the excited triplet state has a long lifetime and thus causes saturation of the excited state and deactivation of energy through mutual action with the excitons in the excited triplet state, and therefore the quantum yield of phosphorescence may generally be often not high.
  • a delayed fluorescent material emits fluorescent light through the mechanism that the energy of excitons transits to the excited triplet state through intersystem crossing or the like, and then transits to the excited singlet state through reverse intersystem crossing due to triplet-triplet annihilation or absorption of thermal energy, thereby emitting fluorescent light. It is considered that among the materials, a thermal activation type delayed fluorescent material emitting light through absorption of thermal energy is particularly useful for an organic electroluminescent device.
  • the excitons in the excited singlet state normally emit fluorescent light.
  • the excitons in the excited triplet state emit fluorescent light through intersystem crossing to the excited singlet state by absorbing the heat generated by the device.
  • the light emitted through reverse intersystem crossing from the excited triplet state to the excited singlet state has the same wavelength as fluorescent light since it is light emission from the excited singlet state, but has a longer lifetime (light emission lifetime) than the normal fluorescent light and phosphorescent light, and thus the light is observed as fluorescent light that is delayed from the normal fluorescent light and phosphorescent light.
  • the light may be defined as delayed fluorescent light.
  • the use of the thermal activation type exciton transition mechanism may raise the proportion of the compound in the excited singlet state, which is generally formed in a proportion only of 25%, to 25% or more through the absorption of the thermal energy after the carrier injection.
  • a compound that emits strong fluorescent light and delayed fluorescent light at a low temperature of lower than l00°C undergoes the intersystem crossing from the excited triplet state to the excited singlet state sufficiently with the heat of the device, thereby emitting delayed fluorescent light, and thus the use of the compound may drastically enhance the light emission efficiency.
  • the compounds of the invention can be synthesized by any method known to one of ordinary skills in the art.
  • the compounds are synthesized from thecommonly available starting material.
  • the various moieties can be assembled via linear or branched synthetic routes.
  • the reaction mixture was added bromobenzene (1.30 mL, 12.2 mmol), 2-ethylhexanoic acid (0.05 mL, 0.305 mmol), and xylene (10 mL) and stirred at room temperature for 15 min, then heated to 90 °C while stirring for 15 h.
  • the reaction mixture was cooled to room temperature, diluted with CHCb (10 mL) and water (10 mL), and filtered through Celite pad followed by washing with CHCb.
  • the aqueous layer was separated and extracted with CHCb (20 mL). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate.
  • the reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 mL) and water (50 mL). The phases were separated, and the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The evaporated residue was purified on silica gel column chromatography using 1 : 1 :3 (v/v/v) hexane/toluene/CHCb as eluent to afford white solid (0.29 g, 79.4%).
  • reaction mixture was cooled to room temperature and diluted with CHCb (10 mL) and water (10 mL).
  • the aqueous layer was separated and extracted with CHCb (20 mL).
  • the combined organic layers were washed with brine and dried over magnesium sulfate.
  • the solvents were evaporated under vacuum, and the crude product was purified by silica gel column chromatography using 6: 1 (v/v) toluene/CHCb as eluent to afford yellow solid (0.50 g, 85.1%).
  • the reaction mixture was added bromobenzene (0.64 mL, 6.09 mmol), 2-ethylhexanoic acid (0.05 mL, 0.305 mmol), and xylene (10 mL) and was stirred at room temperature for 15 min, then heated to 100 °C while stirring for 5 h.
  • the reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and water (10 mL), and filtered through Celite pad followed by washing with ethyl acetate.
  • the aqueous layer was separated and extracted with ethyl acetate (20 mL). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate.
  • the reaction mixture was added bromobenzene (0.64 mL, 6.09 mmol), 2-ethylhexanoic acid (0.05 mL, 0.305 mmol), and xylene (10 mL) and was stirred at room temperature for 15 min, then heated to 100 °C. To fully convert the reaction, additional bromobenzene (0.80 mL, 7.62 mmol) was added in 5 portions every half an hour. After stirring for 24 h, the reaction mixture was cooled to room temperature, diluted with CHCb (10 mL) and water (10 mL), and filtered through Celite pad followed by washing with CHCb. The aqueous layer was separated and extracted with CHCb (20 mL).
  • reaction mixture was stirred at room temperature for 1 h.
  • the reaction was quenched with ethyl acetate and water, and the phases were separated.
  • the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate.
  • the solvent was evaporated in vacuo, and the residue was purified by column chromatography using 1 : 1 :2 (v/v/v) hexane/toluene/CHCb as eluent to afford pale yellow solid (0.35 g, 90.8%).
  • reaction mixture was cooled to room temperature and diluted with 10 mL of ethyl acetate. The resulting solution was washed with brine. The separated organic layer was dried over anhydrous MgSCri, filtered, then evaporated in vacuo. The residue was purified on silica gel column chromatography using 3 : 1 (v/v) toluene/hexane as eluent to give yellow solid (1.63 g, 76.7% yield.
  • the reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL) and water (20 mL). The phases were separated, and the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The evaporated oil-like residue was purified on silica gel column chromatography using 1 : 1 :3 (v/v/v) hexane/toluene/CHCb as eluent to afford yellow solid (1.30 g, 64.1%).
  • the reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL) and water (20 mL). The phases were separated, and the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The evaporated oil-like residue was purified on silica gel column chromatography using 5: 1 (v/v) hexane/ethyl acetate as eluent to afford yellow solid (1.04 g, 70.6%).
  • Example 2 Preparation of neat films
  • the compound synthesised in Example 2 is vapor-deposited on a quartz substrate by a vacuum vapor deposition method under a condition of a vacuum degree of 10 3 Pa or less, so as to form a thin film having a thickness of 70 nm.
  • the compoundand host were also vapor-deposited from a separate vapor deposition source on a quartz substrate by vacuum vapor deposition method under a condition of a vacuum degree of 10 3 Pa or less, so as to form a thin film having a thickness of 100 nm and a concentration of the compoundof 20% by weight.
  • the samples are irradiated with light having a wavelength of 300 nm at 300 K, and thus the light emission spectrum was measured and designated as fluorescence.
  • the spectrum at 77K was also measured and designated as phosphorescence.
  • the lowest singlet energy (Sl) and the lowest triplet energy (Tl) is estimated from the onset of fluorescence and phsphorescence spectrum respectively.
  • AEST is calculated from the energy gap between Sl and Tl .
  • PLQY is also measured by excitation light 300nm.
  • the time resolved spectrum is obtained by excitation light 337nm with Streak Camera, and the component with a short light emission lifetime is designated as fluorescent light, whereas the component with a long light emission lifetime is designated as delayed fluorescent light.
  • the lifetimes of the fluorescent light component (iprompt) and the delayed fluorescent light component (xdeiay) are calculated from the decay curves.
  • Thin films were laminated on a glass substrate having formed thereon an anode formed of indium tin oxide (ITO) having a thickness of 50 nm, by a vacuum vapor deposition method at a vacuum degree of 1.0 x 10 4 Pa or less.
  • ITO indium tin oxide
  • HAT-CN was formed to a thickness of 60 nm on ITO
  • TrisPCz was formed to a thickness of 30 nm.
  • mCBP was formed to a thickness of 5 nm, and thereon the compound 2 and host were then vapor-co-deposited from separate vapor deposition sources to form a layer having a thickness of 30 nm, which was designated as a light-emitting layer.
  • the concentration of the compound was 20% by weight.
  • SF3-TRZ was formed to a thickness of 10 nm, and thereon SF3-TRZ and Liq were vapor-co-deposited to a thickness of 30 nm. Liq was then vacuum vapor-deposited to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing organic electroluminescent devices and measured its photoelectrical properties.

Abstract

La présente invention concerne des composés de formule (I) ou (II), en tant que composés capables d'émettre une fluorescence retardée, et des utilisations des composés dans des diodes électroluminescentes organiques.
PCT/US2019/024856 2018-04-02 2019-03-29 Composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques WO2019195104A1 (fr)

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WO2021046523A1 (fr) 2019-09-05 2021-03-11 Kyulux, Inc. Composition de substances destinée à être utilisée dans des diodes electroluminescentes organiques
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WO2021157599A1 (fr) * 2020-02-05 2021-08-12 株式会社Ｋｙｕｌｕｘ Composé. matériau luminescent, matériau à fluorescence retardée, et dispositif optique organique
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WO2022260119A1 (fr) 2021-06-10 2022-12-15 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
WO2023171688A1 (fr) * 2022-03-08 2023-09-14 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
WO2023199998A1 (fr) * 2022-04-15 2023-10-19 出光興産株式会社 Composé, élément électroluminescent organique et dispositif électronique

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