Compositions for use in organic light-emitting diodes

Abstract

To provide a novel material for delayed fluorescent emitters and for organic light-emitting diodes (OLEDs) that makes it possible to reach higher excitation states without causing rapid degradation and to emit delayed fluorescence.SOLUTION: The present disclosure provides a compound represented by the formula in the figure.SELECTED DRAWING: None

Description

[Technical field]

[0001] Related Applications This application claims the benefit of priority to U.S. Provisional Patent Application No. 62 / 650,414, filed March 30, 2018, U.S. Provisional Patent Application No. 62 / 653,133, filed April 5, 2018, U.S. Provisional Patent Application No. 62 / 653,224, filed April 5, 2018, U.S. Provisional Patent Application No. 62 / 658,842, filed April 17, 2018, U.S. Provisional Patent Application No. 62 / 658,845, filed April 17, 2018, U.S. Provisional Patent Application No. 62 / 662,550, filed April 25, 2018, and U.S. Provisional Patent Application No. 62 / 662,552, filed April 25, 2018. [Background technology]

[0002] An organic light-emitting diode (OLED) is a light-emitting diode (LED) in which a coating of an organic compound that emits light in response to an excitation, such as an electric current, is placed between two conductors. OLEDs are useful in lighting and displays such as television screens, computer monitors, mobile phones and tablets. An inherent problem with OLED displays is the short lifetime of the organic compounds. In particular, OLEDs that emit blue light degrade at a much faster rate than green or red OLEDs.

[0003] OLED materials are based on the radiative decay of molecular excited states (excitons) generated by the recombination of electrons and holes in a host transport material. Due to the nature of the excitation, an interaction occurs between the electron and hole that splits the excited state into a bright singlet (total spin 0) and a dark triplet (total spin 1). Conventional OLEDs have a maximum theoretical efficiency of 25% because the recombination of electrons and holes results in a statistical mixture of four spin states (one singlet and three triplet sublevels).

[0004] Until now, OLED material design has focused on harvesting the remaining energy from the normally dark triplet states. Recent work to create efficient phosphors that emit light from the normally dark triplet states has led to green and red OLEDs. However, for other colors, such as blue, higher energy excited states are required, accelerating the degradation process of the OLEDs.

[0005] The fundamental control factor for triplet-singlet transition rates is the parameter |H fi / ΔE ST | 2 (wherein, H fi is the binding energy due to hyperfine or spin-orbit coupling, and ΔE ST is the energy splitting between the singlet and triplet states. Conventional phosphorescent OLEDs use the mixing of singlet and triplet states via spin-orbit (SO) interactions to produce H fi The approach is based on increasing the charge transport potential of phosphorescent emissive materials to provide the lowest emissive state shared between the heavy metal atom and the organic ligands. This results in phosphorescence (relatively short-lived emission from excited triplets) as a result of energy harvesting from all the higher singlet and triplet states. This shortened triplet lifetime reduces triplet exciton quenching by charge and other excitons. Recent work by others suggests that the performance of phosphorescent emissive materials has reached its limits. Summary of the Invention [Means for solving the problem]

[0006] This disclosure relates to new materials for OLEDs. In some embodiments, these OLEDs can reach higher excited states without rapid degradation. fi In contrast to maximizing ΔE STThermally activated delayed fluorescence (TADF), based on minimization of , has been shown to enable population transitions between singlet and triplet sublevels on moderate time scales, e.g., 1 microsecond to 10 milliseconds. The compounds described herein can emit from higher energy excited states than previously described compounds.

[0007] In some embodiments, the present disclosure provides a compound represented by formula (I):

[0008] [ka]

[0009] (In the formula, R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrogen, deuterium, A 1 , Ar 1 and D. 1 is selected from R 1 , R 2 , R 3 , R 4 and R 5 At least one of 1 and R 1 , R 2 , R 3 , R 4 and R 5 At least one of the following is D 1 and A 1 is, independently,

[0010] [ka]

[0011] is selected from X A are independently O, S and NR A’ is selected from R Ais independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; R A Two or more instances of may be taken together to form a ring system; R A’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R A’ and R A Two or more instances of may be taken together to form a ring system; L A are independently selected from a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene, where each instance of arylene and heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; D 1 is, independently,

[0012] [ka]

[0013] is selected from X D are independently O, S, and NR D’, C(O), substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted vinylene, substituted or unsubstituted o-arylene, and substituted or unsubstituted o-heteroarylene, wherein each instance of methylene, ethylene, vinylene, o-arylene, or o-heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R D is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; R D Two or more instances of may be taken together to form a ring system; R D’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R D’ and R D Two or more instances of may be taken together to form a ring system; L D are independently selected from a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene, where each instance of arylene and heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; Ar 1is independently selected from substituted or unsubstituted heteroaryl not containing any nitrogen atoms, where each instance of aryl and heteroaryl is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; Each "*" represents a point of attachment to formula (I).

[0014] In some embodiments, the present disclosure provides a compound represented by formula (II):

[0015] [ka]

[0016] (In the formula, A is,

[0017] [ka]

[0018] is selected from D is independently H, Me, Ph,

[0019] [ka]

[0020] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20)-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; at least one occurrence of D is selected from D1-D31.

[0021] In some embodiments, the present disclosure provides a compound represented by formula (III):

[0022] [ka]

[0023] (In the formula, A is,

[0024] [ka]

[0025] is selected from D is independently

[0026] [ka]

[0027] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31).

[0028] In some embodiments, the present disclosure provides a compound represented by formula (III):

[0029] [ka]

[0030] (In the formula, A is,

[0031] [ka]

[0032] is selected from D is independently H, deuterium, Ph,

[0033] [ka]

[0034] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31; at least one instance of D is selected from H, deuterium, or Ph.

[0035] In some embodiments, the present disclosure provides a compound represented by formula (IV):

[0036] [ka]

[0037] (In the formula, A is,

[0038] [ka]

[0039] is selected from D is independently

[0040] [ka]

[0041] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31).

[0042] In some embodiments, the present disclosure provides a compound represented by formula (IV):

[0043] [ka]

[0044] (In the formula, A is,

[0045] [ka]

[0046] is selected from D is independently H, deuterium, Ph,

[0047] [ka]

[0048] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31; at least one instance of D is selected from H, Ph, or deuterium.

[0049] In some embodiments, the present disclosure provides a delayed fluorescent emitter comprising a compound of formula (I), formula (II), formula (III), or formula (IV).

[0050] In some embodiments, the present disclosure provides an organic light emitting diode (OLED) comprising a compound of Formula (I), Formula (II), Formula (III), or Formula (IV).

[0051] In some embodiments, provided herein is an organic light emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, wherein the emissive layer comprises a host material and a compound of Formula (I), Formula (II), Formula (III), or Formula (IV).

[0052] In some embodiments, provided herein is an organic light emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A host material; A compound of formula (I), (II), (III) or (IV), wherein the compound of formula (I), (II), (III) or (IV) above is an emissive material.

[0053] In some embodiments, provided herein is an organic light emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A host material; A compound of formula (I), (II), (III) or (IV), a light-emitting material that is not a compound of formula (I), formula (II), formula (III) or formula (IV); An organic light emitting diode (OLED) is provided, comprising:

[0054] In some embodiments, provided herein is an organic light emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A compound of formula (I), (II), (III) or (IV), a light-emitting material which is not a compound of formula (I), formula (II), formula (III) or formula (IV); An organic light emitting diode (OLED) is provided, comprising:

[0055] In some embodiments, the compounds of formula (I), formula (II), formula (III) or formula (IV) above are used in a screen or display.

[0056] In yet another aspect, the present disclosure provides a method for manufacturing an OLED display, comprising: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in units of cell panels; forming a sealing layer on each display unit of the cell panel; applying an organic coating to the interface between the cell panels; The present invention relates to a method comprising the steps of: [Brief description of the drawings]

[0057] [Figure 1] In the figure, 1 indicates a substrate, 2 indicates an anode, 3 indicates a hole injection layer, 4 indicates a hole transport layer, 5 indicates a light emitting layer, 6 indicates an electron transport layer, and 7 indicates a cathode. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0058] In one aspect, the present disclosure provides a compound of formula (I):

[0059] [ka]

[0060] (In the formula, R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrogen, deuterium, A 1 , Ar 1 and D. 1 is selected from R 1 , R 2 , R 3 , R 4 and R 5 At least one of 1 and R 1 , R 2 , R 3 , R 4 and R 5 At least one of the following is D 1 and A 1 is, independently,

[0061] [ka]

[0062] is selected from X A are independently O, S and NR A’ is selected from R A is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; R A Two or more instances of may be taken together to form a ring system; R A’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R A’ and R A Two or more instances of may be taken together to form a ring system; L A are independently selected from a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene, where each instance of arylene and heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; D 1 is, independently,

[0063] [ka]

[0064] is selected from X D are independently O, S, and NR D’ , C(O), substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted vinylene, substituted or unsubstituted o-arylene, and substituted or unsubstituted o-heteroarylene, wherein each instance of methylene, ethylene, vinylene, o-arylene, or o-heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R D is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; R D Two or more instances of may be taken together to form a ring system; R D’ are independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R D’ and R D Two or more instances of may be taken together to form a ring system; L Dare independently selected from a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene, where each instance of arylene and heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; Ar 1 is independently selected from substituted or unsubstituted heteroaryl not containing any nitrogen atoms, where each instance of aryl and heteroaryl is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; Each "*" represents a point of attachment to formula (I).

[0065] In some embodiments, the compound of formula (I) is

[0066] [ka]

[0067] is selected from.

[0068] In some embodiments, the compound of formula (I) is

[0069] [ka]

[0070] is selected from.

[0071] In some embodiments, the compound of formula (I) is

[0072] [ka]

[0073] is selected from.

[0074] In one aspect, the present disclosure provides a compound of formula (II):

[0075] [ka]

[0076] (In the formula, A is,

[0077] [ka]

[0078] is selected from D is independently H, Me, Ph,

[0079] [ka]

[0080] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; at least one occurrence of D is selected from D1-D31.

[0081] In one aspect, the present disclosure provides a compound of formula (III):

[0082] [ka]

[0083] (In the formula, A is,

[0084] [ka]

[0085] is selected from D is independently

[0086] [ka]

[0087] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31).

[0088] In one aspect, the present disclosure provides a compound of formula (III):

[0089] [ka]

[0090] (In the formula, A is,

[0091] [ka]

[0092] is selected from D is independently H, deuterium, Ph,

[0093] [ka]

[0094] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31; at least one instance of D is selected from H, deuterium, or Ph.

[0095] In one aspect, the present disclosure provides a compound of formula (IV):

[0096] [ka]

[0097] (In the formula, A is,

[0098] [ka]

[0099] is selected from D is independently

[0100] [ka]

[0101] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31).

[0102] In one aspect, the present disclosure provides a compound of formula (IV):

[0103] [ka]

[0104] (In the formula, A is,

[0105] [ka]

[0106] is selected from D is independently H, deuterium, Ph,

[0107] [ka]

[0108] is selected from R is independently selected from H, Me, and Ph; Z1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31; at least one instance of D is selected from H, Ph, or deuterium.

[0109] Examples are provided for the purpose of illustrating the disclosure, but are not intended to limit the disclosure. Indeed, it will be apparent to those skilled in the art that various modifications and variations can be made to the present disclosure without departing from the scope or spirit of the disclosure. For example, features described or described as part of one embodiment can be used in another embodiment to obtain yet a further embodiment. Therefore, the present disclosure is intended to cover modifications and variations that fall within the scope of the appended claims and their equivalents. Other objects, features and aspects of the present disclosure are disclosed in or can be derived from the following detailed description. It should be understood by those skilled in the art that the discussion of the present disclosure is merely a description of exemplary embodiments, and should not be interpreted as limiting the broader aspects of the present disclosure.

[0110] definition Unless otherwise specified herein, scientific and technical terms used in this application shall have the meanings commonly understood by those of ordinary skill in the art. In general, the nomenclature used in reference to the chemicals described herein and techniques therefor are well known and commonly used in the art.

[0111] The term "acyl" is art-recognized and refers to a group represented by the general formula hydrocarbylC(O)-, preferably alkylC(O)-.

[0112] The term "acylamino" is art-recognized and refers to an amino group substituted with an acyl group and may be represented, for example, by the formula hydrocarbylC(O)NH-.

[0113] The term "acyloxy" is art-recognized and refers to a group represented by the general formula hydrocarbylC(O)O-, preferably alkylC(O)O-.

[0114] The term "alkoxy" refers to an alkyl group having an oxygen atom attached thereto. In some embodiments, an alkoxy has 1-20 carbons. In some embodiments, an alkoxy has 1-12 carbon atoms. Representative alkoxy groups include methoxy, trifluoromethoxy, ethoxy, propoxy, tert-butoxy, and the like.

[0115] The term "alkoxyalkyl" refers to an alkyl group substituted with an alkoxy group and may be represented by the general formula alkyl-O-alkyl.

[0116] The term "alkenyl" as used herein refers to an aliphatic group containing at least one double bond, and is intended to include "unsubstituted alkenyl" and "substituted alkenyl", the latter of which refers to an alkenyl moiety having a substituent replacing a hydrogen on one or more carbons of the alkenyl group. Typically, a straight or branched chain alkenyl group has 1 to about 20, preferably 1 to about 12, carbon atoms, unless otherwise specified. Such a substituent may be present on one or more carbons that are included or not included in one or more double bonds. Furthermore, such a substituent includes all of the substituents contemplated for an alkyl group as described below, so long as stability is not impaired. For example, substitution of an alkenyl group with one or more alkyl, carbocyclyl, aryl, heterocyclyl or heteroaryl groups is contemplated.

[0117] An "alkyl" group or "alkane" is a fully saturated, straight or branched chain non-aromatic hydrocarbon. Typically, a straight or branched chain alkyl group has from 1 to about 20 carbon atoms, preferably from 1 to about 12 carbon atoms, unless otherwise specified. In some embodiments, an alkyl group has from 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms, or 1 to 3 carbon atoms. Examples of straight and branched chain alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, pentyl, and octyl.

[0118] Furthermore, the term "alkyl" as used throughout the specification, examples, and claims is intended to include both "unsubstituted alkyl" and "substituted alkyl," the latter of which refers to an alkyl moiety having substituents replacing hydrogen on one or more substitutable carbons of the hydrocarbon backbone. Such substituents can include, for example, halogen (e.g., fluoro), hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxy, phosphoryl, phosphate, phosphonate, phosphinate, amino, amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, aralkyl, or aromatic or heteroaromatic moieties, unless otherwise specified. In a preferred embodiment, the substituent on the substituted alkyl is C 1~6 Alkyl, C 3~6 In a more preferred embodiment, the substituents on the substituted alkyl are selected from fluoro, carbonyl, cyano, or hydroxyl. It will be understood by those skilled in the art that the substituted moieties on the hydrocarbon chain may themselves be substituted as appropriate. For example, the substituents on the substituted alkyl may include ethers, alkylthio, carbonyls (including ketones, aldehydes, carboxylates, and esters), -CF, as well as substituted and unsubstituted amino, azide, imino, amide, phosphoryl (including phosphonate and phosphinate), sulfonyl (including sulfate, sulfonamide, sulfamoyl, and sulfonate), and silyl groups. 3 Exemplary substituted alkyls are described below. Cycloalkyl can be an alkyl, alkenyl, alkoxy, alkylthio, aminoalkyl, carbonyl-substituted alkyl, -CF 3 , -CN, and the like.

[0119] "C x~yThe term "C" when used in connection with chemical moieties such as acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy, is intended to include groups containing x to y carbons in the chain. For example, "C x~y The term "alkyl" refers to substituted or unsubstituted saturated hydrocarbon groups, including straight-chain and branched-chain alkyl groups, containing x to y carbons in the chain, including haloalkyl groups. Preferred haloalkyl groups include trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, and pentafluoroethyl. 0 An alkyl group represents a hydrogen atom if the group is terminal and a bond if the group is internal. 2~y alkenyl" and "C 2~y The term "alkynyl" refers to substituted or unsubstituted unsaturated aliphatic groups analogous in length and possible substitution to the alkyls described above, but which contain at least one double or triple bond respectively.

[0120] The term "alkylamino," as used herein, refers to an amino group substituted with at least one alkyl group.

[0121] The term "alkylthio," as used herein, refers to a thiol group substituted with an alkyl group and may be represented by the general formula alkylS-.

[0122] The term "arylthio," as used herein, refers to a thiol group substituted with an aryl group and may be represented by the general formula arylS-.

[0123] The term "alkynyl" as used herein refers to an aliphatic group containing at least one triple bond, and is intended to include both "unsubstituted alkynyl" and "substituted alkynyl", the latter of which refers to an alkynyl moiety having a substituent replacing a hydrogen on one or more carbons of the alkynyl group. Typically, a straight or branched chain alkynyl group has 1 to about 20, preferably 1 to about 10, carbon atoms, unless otherwise specified. Such a substituent may be present on one or more carbons that are included or not included in one or more triple bonds. Furthermore, such substituents include all of the substituents contemplated for alkyl groups as described above, so long as stability is not impaired. For example, substitution of an alkynyl group with one or more alkyl, carbocyclyl, aryl, heterocyclyl or heteroaryl groups is contemplated.

[0124] As used herein, the term "amide" refers to the group

[0125] [ka]

[0126] (In the formula, each R A independently represent hydrogen or a hydrocarbyl group, or two R A together with the N atom to which they are attached form a heterocycle having 4 to 8 atoms in the ring structure.

[0127] The terms "amine" and "amino" are art-recognized and refer to both unsubstituted and substituted amines and their salts, e.g.,

[0128] [ka]

[0129] (In the formula, each R A independently represent hydrogen or a hydrocarbyl group, or two R Arefers to a moiety that can be represented by the formula: (which together with the N atom to which they are attached form a heterocycle having 4 to 8 atoms in the ring structure).

[0130] As used herein, the term "aminoalkyl" refers to an alkyl group substituted with an amino group.

[0131] As used herein, the term "aralkyl" refers to an alkyl group substituted with an aryl group.

[0132] The term "aryl" as used herein includes substituted or unsubstituted monocyclic aromatic groups in which each atom of the ring is carbon. Preferably, the ring is 6-20 membered, more preferably 6 membered. Preferably, the aryl has 6-40 carbon atoms, more preferably 6-25 carbon atoms. The term "aryl" also includes polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjacent rings, at least one of which is aromatic, and in which the other cyclic rings may be, for example, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclyl. Aryl groups include benzene, naphthalene, phenanthrene, phenol, aniline, and the like.

[0133] The term "carbamate" is art-recognized and refers to a group

[0134] [ka]

[0135] (In the formula, each R A R independently represents hydrogen or a hydrocarbyl group, e.g., an alkyl group, or both R A refers to a heterocyclic ring, which, together with one or more intervening atoms, forms a heterocyclic ring having from 4 to 8 atoms in the ring structure.

[0136] The terms "carbocycle" and "carbocyclic" as used herein refer to a saturated or unsaturated ring in which each atom of the ring is carbon. Preferably, a carbocyclic group has 3 to 20 carbon atoms. The term carbocycle includes both aromatic and non-aromatic carbocycles. Non-aromatic carbocycles include both cycloalkane rings in which all carbon atoms are saturated and cycloalkene rings that contain at least one double bond. "Carbocycle" includes 5- to 7-membered monocyclic rings and 8- to 12-membered bicyclic rings. Each ring of a bicyclic carbocycle may be selected from a saturated ring, an unsaturated ring, and an aromatic ring. Carbocycles include 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 ring shares two adjacent atoms with the other ring. Each ring of a fused carbocycle may be selected from a saturated ring, an unsaturated ring, and an aromatic ring. In exemplary embodiments, an aromatic ring, such as phenyl (Ph), may be fused to a saturated or unsaturated ring, such as cyclohexane, cyclopentane, or cyclohexene. Any combination of saturated, unsaturated, and aromatic bicyclic rings is included in the definition of carbocycle, as long as valences permit. Exemplary "carbocycles" include cyclopentane, cyclohexane, bicyclo[2.2.1]heptane, 1,5-cyclooctadiene, 1,2,3,4-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-1H-indene, and bicyclo[4.1.0]hept-3-ene. A "carbocycle" may be substituted at any one or more positions that may have a hydrogen atom.

[0137] A "cycloalkyl" group is a fully saturated cyclic hydrocarbon. "Cycloalkyl" includes monocyclic and bicyclic rings. Preferably, a cycloalkyl group has 3 to 20 carbon atoms. Typically, a monocyclic cycloalkyl group has 3 to about 10 carbon atoms, more typically 3 to 8 carbon atoms, unless otherwise specified. The second ring of a bicyclic cycloalkyl may be selected from a saturated ring, an unsaturated ring, and an aromatic ring. Cycloalkyl includes bicyclic molecules in which one, two, or three or more atoms are shared between the two rings. The term "fused cycloalkyl" refers to a bicyclic cycloalkyl in which each ring shares two adjacent atoms with the other ring. The second ring of a fused bicyclic cycloalkyl may be selected from a saturated ring, an unsaturated ring, and an aromatic ring. A "cycloalkenyl" group is a cyclic hydrocarbon containing one or more double bonds.

[0138] The term "carbocycloalkyl," as used herein, refers to an alkyl group substituted with a carbocycle group.

[0139] As used herein, the term "carbonate" refers to the group -OCO 2 -R A (In the formula, R A represents a hydrocarbyl group).

[0140] As used herein, the term "carboxy" refers to a group of the formula -CO 2 H.

[0141] As used herein, the term "ester" refers to an ester selected from the group -C(O)OR A (In the formula, R A represents a hydrocarbyl group).

[0142] The term "ether" as used herein refers to a hydrocarbyl group linked to another hydrocarbyl group through an oxygen. Thus, the ether substituent of a hydrocarbyl group can be hydrocarbyl-O-. Ethers can be either symmetrical or asymmetrical. Examples of ethers include, but are not limited to, heterocycle-O-heterocycle and aryl-O-heterocycle. Ethers include "alkoxyalkyl" groups, which can be represented by the general formula alkyl-O-alkyl.

[0143] The terms "halo" and "halogen" as used herein mean halogen and include chloro, fluoro, bromo and iodo.

[0144] The terms "hetaralkyl" and "heteroaralkyl," as used herein, refer to an alkyl group substituted with a hetaryl group.

[0145] The term "heteroalkyl," as used herein, refers to a saturated or unsaturated chain of carbon atoms and at least one heteroatom in which the two heteroatoms are not adjacent.

[0146] The terms "heteroaryl" and "hetaryl" include substituted or unsubstituted aromatic monocyclic structures, preferably 5- to 20-membered rings, more preferably 5- to 6-membered rings, containing at least one heteroatom, preferably 1-4 heteroatoms, more preferably 1 or 2 heteroatoms. Preferably, heteroaryls have 2-40 carbon atoms, more preferably 2-25 carbon atoms. The terms "heteroaryl" and "hetaryl" also include polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjacent rings, at least one of which is heteroaromatic, and in which the other cyclic rings can be, for example, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclyl. Heteroaryl groups include, for example, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, and carbazole.

[0147] The term "aryloxy" refers to an aryl group having an oxygen atom attached thereto. Preferably, the aryloxy has from 6 to 40 carbon atoms, more preferably from 6 to 25 carbon atoms.

[0148] The term "heteroaryloxy" refers to an aryl group having an oxygen atom attached thereto. Preferably, the heteroaryloxy has from 3 to 40 carbon atoms, more preferably from 3 to 25 carbon atoms.

[0149] The term "heteroatom" as used herein means an atom of any element other than carbon or hydrogen. Preferred heteroatoms are nitrogen, oxygen and sulfur.

[0150] The terms "heterocyclyl", "heterocycle" and "heterocyclic" refer to a substituted or unsubstituted non-aromatic ring structure, preferably 3-20 membered, more preferably 3-7 membered, containing at least one heteroatom, preferably 1-4 heteroatoms, more preferably 1 or 2 heteroatoms. The terms "heterocyclyl" and "heterocyclic" also include polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjacent rings, at least one of which is heterocyclic, e.g., the other cyclic rings can be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclyl. Heterocyclyl groups include, for example, piperidine, piperazine, pyrrolidine, morpholine, lactones, lactams, and the like.

[0151] The term "heterocyclylalkyl," as used herein, refers to an alkyl group substituted with a heterocycle group.

[0152] The term "hydrocarbyl" as used herein refers to a group that is bonded through a carbon atom that does not have a =O or =S substituent. Hydrocarbyl may optionally contain heteroatoms. Hydrocarbyl groups include, but are not limited to, alkyl, alkenyl, alkynyl, alkoxyalkyl, aminoalkyl, aralkyl, aryl, aralkyl, carbocyclyl, cycloalkyl, carbocyclylalkyl, heteroaralkyl, heteroaryl, heterocyclyl, heterocyclylalkyl, or hydroxyalkyl groups bonded through a carbon atom. Thus, groups such as methyl, ethoxyethyl, 2-pyridyl, and trifluoromethyl are hydrocarbyl groups, while substituents such as acetyl (having a =O substituent on the connecting carbon) and ethoxy (linked through an oxygen rather than a carbon) are not hydrocarbyl groups.

[0153] As used herein, the term "hydroxyalkyl" refers to an alkyl group substituted with a hydroxy group.

[0154] The term "lower" when used in connection with chemical moieties such as acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy, is intended to include groups in which there are six or fewer non-hydrogen atoms in the substituent. For example, "lower alkyl" refers to an alkyl group containing six or fewer carbon atoms. In some embodiments, a lower alkyl group has 1 to 6 carbon atoms, 1 to 4 carbon atoms, or 1 to 3 carbon atoms. In certain embodiments, an acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy substituent as defined herein is a lower acyl, lower acyloxy, lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy, respectively, whether they are present alone or in combination with other substituents, such as in the enumeration of hydroxyalkyl and aralkyl (where the atoms in the aryl group are not counted, for example, when counting the carbon atoms in the alkyl substituent).

[0155] The terms "polycyclyl", "polycycle" and "polycyclic" refer to two or more rings (e.g., cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, and / or heterocyclyl) in which two or more atoms are common to two adjacent rings, e.g., the rings are "fused rings". Each ring of the polycycle may be substituted or unsubstituted. In certain embodiments, each ring of the polycycle contains 3 to 10 atoms in the ring, preferably 5 to 7 atoms.

[0156] In the phrase "poly(meta-phenylene oxide)," the term "phenylene" refers inclusively to a 6-membered aryl or 6-membered heteroaryl moiety. Exemplary poly(meta-phenylene oxide)s are described in the first through twentieth aspects of the present disclosure.

[0157] The term "silyl" refers to a silicon moiety having three hydrocarbyl moieties attached thereto.

[0158] The term "substituted" refers to a moiety having a substituent replacing a hydrogen on one or more carbons of the backbone. "Substituted" or "substituted with" is understood to include the implicit proviso that such substitution results in a stable compound that does not spontaneously undergo transformation, for example, by rearrangement, cyclization, elimination, etc., subject to the permissible valences of the substituted atom and substituent. Moieties that can be substituted can include any suitable substituents described herein, such as acyl, acylamino, acyloxy, alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylamino, alkylthio, arylthio, alkynyl, amido, amino, aminoalkyl, aralkyl, carbamate, carbocyclyl, cycloalkyl, carbocyclylalkyl, carbonate, ester, ether, heteroaralkyl, heterocyclyl, heterocyclylalkyl, hydrocarbyl, silyl, sulfone, or thioether. As used herein, the term "substituted" is intended to include all permissible substituents of organic compounds. In a broad aspect, permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds. Permissible substituents may be one or more and the same or different for suitable organic compounds. For purposes of this invention, heteroatoms such as nitrogen may have any permissible substituent of organic compounds described herein that satisfies the valence of the hydrogen and / or heteroatoms. Substituents may include any of the substituents described herein, such as halogen, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), thiocarbonyl (e.g., thioester, thioacetate, or thioformate), alkoxy, phosphoryl, phosphate, phosphonate, phosphinate, amino, amido, amidine, imine, cyano, nitro, azido, sulfhydryl, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclyl, aralkyl, or aromatic or heteroaromatic moieties. In a preferred embodiment, the substituents on the substituted alkyl group are 1~6 Alkyl, C 3~6In a more preferred embodiment, the substituent on the substituted alkyl group is selected from fluoro, carbonyl, cyano or hydroxyl. As will be understood by those skilled in the art, the substituent itself can be substituted as appropriate. Unless specifically indicated as "unsubstituted", references to chemical groups herein are understood to include substituted variants. For example, references to "aryl" groups or moieties implicitly include both substituted and unsubstituted variants.

[0159] The term "sulfonate" is art-recognized and refers to the group SO 3 H or a pharma- ceutically acceptable salt thereof.

[0160] The term "sulfone" is art-recognized and refers to the group -S(O) 2 -R A (In the formula, R A represents hydrocarbyl).

[0161] The term "thioether" as used herein corresponds to an ether where the oxygen has been replaced with a sulfur.

[0162] The term "symmetric molecule" as used herein refers to a molecule that is group symmetric or synthetic symmetric. The term "group symmetric" as used herein refers to a molecule that has symmetry according to the group theory of molecular symmetry. The term "synthetic symmetric" as used herein refers to a molecule that is selected such that regioselective synthetic strategies are not required.

[0163] The term "donor" as used herein may be used in an organic light-emitting diode and refers to a molecular fragment that upon excitation is expected to donate an electron from the highest occupied molecular orbital to an acceptor. In a preferred embodiment, the donor comprises a substituted amino group. In an exemplary embodiment, the donor has an ionization potential of -6.5 eV or greater.

[0164] The term "acceptor" as used herein may be used in organic light emitting diodes and refers to a molecular fragment that is expected to accept an electron from an excited donor into the lowest unoccupied molecular orbital. In an exemplary embodiment, the acceptor has an electron affinity of -0.5 eV or less.

[0165] The term "linker" or "bridge" as used herein refers to a molecular fragment that may be included in a molecule covalently linked between an acceptor moiety and a donor moiety. The linker may, for example, be further conjugated to the acceptor moiety, the donor moiety, or both. Without being bound by any particular theory, it is believed that the linker moiety may sterically restrict the acceptor moiety and the donor moiety to a particular configuration, thereby preventing overlap between the conjugated pi-systems of the donor and acceptor moieties. Examples of suitable linker moieties include phenyl, ethenyl, and ethynyl.

[0166] The term "multivalent" as used herein refers to a molecular fragment that is connected to at least two other molecular fragments. For example, a linker moiety is multivalent.

[0167] As used herein, "~~~" or "*" refers to the point of attachment between two atoms.

[0168] "Hole transport layer (HTL)" and similar terms refer to a layer made of a material that transports holes. High hole mobility is recommended. The HTL is used to assist in blocking the passage of electrons transported by the emissive layer. A low electron affinity is typically required to block electrons. The HTL should desirably have more triplets to block the migration of excitons from the adjacent emissive layer (EML). Examples of HTL compounds include, but are not limited to, [di(p-tolyl)aminophenyl]cyclohexane (TAPC), N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD), and N,N'-diphenyl-N,N'-bis(1-naphthyl)-(1,1'-biphenyl)-4,4'-diamine (NPB, α-NPD).

[0169] "Emitting layer" and similar terms refer to a layer that emits light. In some embodiments, the emitting layer includes a host material and a guest material. The guest material can also be referred to as a dopant material, but the present disclosure is not limited thereto. The host material or "host" can be bipolar or monopolar and can be used alone or with a combination of two or more host materials. The opto-electrical properties of the host material can differ depending on which type of guest material (TADF, phosphorescent or fluorescent) is used. In the case of a fluorescent guest material, the host material should have good spectral overlap between the absorption of the guest material and the emission of the material to induce good Förster transfer to the guest material. In the case of a phosphorescent guest material, the host material should have high triplet energy to confine the triplet of the guest material. In the case of a TADF guest material, the host material should have both spectral overlap and higher triplet energy.

[0170] "Dopant" and similar terms refer to additive materials for carrier transport layers, light-emitting layers or other layers. In carrier transport layers, dopants and similar terms function as electron acceptors or electron donors when added as additives to organic layers to enhance the conductivity of the organic layers of organic electronic devices. Similarly, organic semiconductors may be influenced for their electrical conductivity by doping. Such organic semiconductor matrix materials may be composed of either compounds with electron donor properties or compounds with electron acceptor properties. In light-emitting layers, dopant and similar terms also refer to light-emitting materials dispersed in a matrix, e.g., a host. When a triplet harvesting material is doped into the light-emitting layer or included in an adjacent layer to improve exciton generation efficiency, the triplet harvesting material is called an auxiliary dopant. The content of the auxiliary dopant in the light-emitting layer or adjacent layer is not particularly limited, provided that the triplet harvesting material improves exciton generation efficiency. The content of the auxiliary dopant in the light-emitting layer is preferably higher than that of the light-emitting material, more preferably at least twice as high. In the light-emitting layer, the content of the host material is preferably 50% by weight or more, the content of the auxiliary dopant is preferably 5% to less than 50% by weight, and the content of the light-emitting material is preferably 0% to less than 25% by weight, more preferably 0% to less than 10% by weight. The content of the auxiliary dopant in the adjacent layer may be more than 50% by weight or may be 100% by weight. When a device containing the triplet harvesting material in the light-emitting layer or an adjacent layer has a higher light-emitting efficiency than a device without the triplet harvesting material, such a triplet harvesting material functions as an auxiliary dopant. The light-emitting layer containing the host material, the auxiliary dopant, and the light-emitting material satisfies the following (A), and preferably satisfies the following (B): ES1(A)>ES1(B)>ES1(C) (A) ET1(A)>ET1(B) (B) Here, ES1(A) represents the lowest excited singlet energy level of the host material, ES1(B) represents the lowest excited singlet energy level of the auxiliary dopant, ES1(C) represents the lowest excited singlet energy level of the light-emitting material, ET1(A) represents the lowest excited triplet energy level of the host material at 77 K, and ET1(B) represents the lowest excited triplet energy level of the auxiliary dopant at 77 K. The auxiliary dopant has an energy difference ΔE between the lowest singlet excited state and the lowest triplet excited state at 77 K. st is preferably 0.3 eV or less, more preferably 0.2 eV or less, and even more preferably 0.1 eV or less.

[0171] In the compounds of the present invention, any atom that is not specifically designated as a particular isotope is intended to represent any stable isotope of that atom.Unless otherwise indicated, when a position is specifically designated as "H" or "hydrogen", that position is understood to have hydrogen at its natural abundance isotopic composition.Unless otherwise indicated, when a position is specifically designated as "D" or "deuterium", that position is understood to have deuterium at an abundance at least 3340 times greater than the natural abundance of deuterium, 0.015% (i.e., at least 50.1% deuterium incorporation).

[0172] "D" and "d" both refer to deuterium.

[0173] "Deuterium substituted" refers to the replacement of one or more hydrogen atoms with the corresponding number of deuterium atoms.

[0174] The term "isotopic enrichment factor" as used herein means the ratio between the isotopic abundance and the natural abundance of a particular isotope.

[0175] In various embodiments, the compounds of the present 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).

[0176] The term "isotopomer" refers to a chemical species that differs from a specific compound of this invention only in its isotopic composition.

[0177] The term "compound" when referring to a compound of the present invention refers to a collection of molecules having the same chemical structure, except that there may be isotopic variations in the constituent atoms of the molecule. Thus, it will be clear to one skilled in the art that a compound represented by a particular chemical structure containing a deuterium atom as shown also includes lesser amounts of isotopic substitutions having hydrogen atoms at one or more of the designated deuterium positions in the structure. The relative amount of such isotopic substitutions in the compounds of the present invention depends on many factors, including the isotopic purity of the deuteration reagent used to make the compound and the efficiency of introducing deuterium in the various synthetic steps used to prepare the compound. However, as noted above, the relative amount of such isotopic substitutions overall is less than 49.9% of the compound. In other embodiments, the relative amount of such isotopic substitutions overall is 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.

[0178] Principles of OLED OLEDs are typically constructed of a layer of organic materials or compounds between two electrodes: an anode and a cathode. Organic molecules are electrically conductive as a result of delocalization of π electrons caused by conjugation across some or all of the molecule. When a voltage is applied, electrons from the highest occupied molecular orbital (HOMO), present at the anode, flow into the lowest unoccupied molecular orbital (LUMO) of the organic molecule, present at the cathode. The removal of an electron from the HOMO is also called the insertion of a hole into the HOMO. Electrostatic forces attract the electron and hole to each other until they recombine to form an exciton (a combined state of electron and hole). When the excited state decays and the energy levels of the electrons relax, radiation with frequencies in the visible spectrum is emitted. The frequency of this radiation depends on the band gap of the material, which is the difference in energy between the HOMO and the LUMO.

[0179] Since electrons and holes are fermions with half-integer spin, excitons can be in either singlet or triplet states, depending on how the electron and hole spins are coupled. Statistically, three triplet excitons are formed for each singlet exciton. Decay from the triplet state is spin-forbidden, leading to an increase in the transition timescale and limiting the internal efficiency of fluorescent light-emitting devices. Phosphorescent organic light-emitting diodes use spin-orbit interactions to facilitate intersystem crossing between the singlet and triplet states, thereby obtaining emission from both the singlet and triplet states and improving internal efficiency.

[0180] One of the prototypic phosphorescent materials is iridium tris(2-phenylpyridine) (Ir(ppy)), whose excited state is a charge transfer from the Ir atom to an organic ligand. 3 ). With such an approach, the triplet lifetime has been reduced to roughly a few microseconds, several orders of magnitude slower than the radiative lifetime of fully allowed transitions such as fluorescence. Although Ir-based phosphors have proven acceptable for many display applications, losses due to the large triplet density have yet to apply OLEDs to higher brightness solid-state lighting.

[0181] TADF is ΔE ST The reduction of the exchange splitting from typical values ​​of 0.4 eV-0.7 eV to the order gap for thermal energy (proportional to kBT, where kB represents the Boltzmann constant and T represents the temperature) means that thermal stirring allows the population to transition between the singlet and triplet sublevels on a reasonable time scale, even if the coupling between the states is small.

[0182] TADF molecules consist of donor and acceptor moieties that are connected directly, either by a covalent bond or through a conjugated linker (or "bridge"). The "donor" moiety is expected to transfer an electron from its HOMO upon excitation to the "acceptor" moiety. The "acceptor" moiety is expected to accept an electron from the "donor" moiety into its LUMO. The donor-acceptor nature of TADF molecules results in very low ΔE ST This results in a low-lying excited state with charge-transfer characteristics that exhibit. Because thermal molecular motion can randomly perturb the optical properties of the donor-acceptor system, a rigid three-dimensional arrangement of the donor and acceptor moieties can be used to restrict non-radiative decay of the charge-transfer state by internal conversion during the lifetime of the excitation.

[0183] Therefore, ΔE ST It would be beneficial to create systems with increased reverse intersystem crossing (RISC) that can reduce the charge transport and harness triplet excitons. Such systems would result in increased quantum efficiency and reduced emission lifetime. Systems with these characteristics would be able to emit light without undergoing the rapid degradation common in OLEDs known today.

[0184] Compounds of the Disclosure In some embodiments, the compound has formula (I):

[0185] [ka]

[0186] (In the formula, R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrogen, deuterium, A 1 , Ar 1 and D. 1 is selected from R 1 , R 2 , R 3 , R 4 and R 5 At least one of 1 and R 1 , R 2 , R 3 , R 4 and R 5 At least one of the following is D 1 and A 1 is, independently,

[0187] [ka]

[0188] is selected from X A are independently O, S and NR A’ is selected from R A is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; R A Two or more instances of may be taken together to form a ring system; R A’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; RA’ and R A Two or more instances of may be taken together to form a ring system; L A are independently selected from a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene, where each instance of arylene and heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; D 1 is, independently,

[0189] [ka]

[0190] is selected from X D are independently O, S, and NR D’ , C(O), substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted vinylene, substituted or unsubstituted o-arylene, and substituted or unsubstituted o-heteroarylene, wherein each instance of methylene, ethylene, vinylene, o-arylene, or o-heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R D is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; RD Two or more instances of may be taken together to form a ring system; R D’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R D’ and R D Two or more instances of may be taken together to form a ring system; L D are independently selected from a single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene, where each instance of arylene and heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; Ar 1 is independently selected from substituted or unsubstituted heteroaryl not containing any nitrogen atoms, where each instance of aryl and heteroaryl is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which substituents may be joined together to form a ring system; Each "*" represents a point of attachment to formula (I).

[0191] In some embodiments, A 1 teeth,

[0192] [ka]

[0193] In some embodiments, A 1 teeth,

[0194] [ka]

[0195] In some embodiments, A 1 teeth,

[0196] [ka]

[0197] In some embodiments, A 1 teeth,

[0198] [ka]

[0199] In some embodiments, A 1 teeth,

[0200] [ka]

[0201] In some embodiments, A 1 teeth,

[0202] [ka]

[0203] In some embodiments, A 1 teeth,

[0204] [ka]

[0205] In some embodiments, A 1 teeth,

[0206] [ka]

[0207] In some embodiments, A 1 teeth,

[0208] [ka]

[0209] In some embodiments, A 1 teeth,

[0210] [ka]

[0211] It is.

[0212] In some embodiments, A 1 teeth,

[0213] [ka]

[0214] is selected from.

[0215] In some embodiments, A 1 teeth,

[0216] [ka]

[0217] is selected from.

[0218] In some embodiments, A 2 teeth,

[0219] [ka]

[0220] In some embodiments, A 2 teeth,

[0221] [ka]

[0222] In some embodiments, A 2 teeth,

[0223] [ka]

[0224] In some embodiments, A 2 teeth,

[0225] [ka]

[0226] In some embodiments, A 2 teeth,

[0227] [ka]

[0228] In some embodiments, A 2 teeth,

[0229] [ka]

[0230] In some embodiments, A 2 teeth,

[0231] [ka]

[0232] In some embodiments, A 2 teeth,

[0233] [ka]

[0234] In some embodiments, A 2 teeth,

[0235] [ka]

[0236] In some embodiments, A 2 teeth,

[0237] [ka]

[0238] It is.

[0239] In some embodiments, R 1 is hydrogen. In some embodiments, R 1 is deuterium. In some embodiments, R 1 A 2 In some embodiments, R 1 Ar 1 In some embodiments, R 1 D 1 It is.

[0240] In some embodiments, R 2 is hydrogen. In some embodiments, R 2 is deuterium. In some embodiments, R 2 A 2 In some embodiments, R 2 Ar 1 In some embodiments, R 2 D 1 It is.

[0241] In some embodiments, R 3 is hydrogen. In some embodiments, R 3 is deuterium. In some embodiments, R 3 A 2 In some embodiments, R 3 Ar 1 In some embodiments, R 3 D 1 It is.

[0242] In some embodiments, R 4 is hydrogen. In some embodiments, R 4 is deuterium. In some embodiments, R 4 A 2 In some embodiments, R 4 Ar 1 In some embodiments, R 4 D 1 It is.

[0243] In some embodiments, R 5 is hydrogen. In some embodiments, R 5 is deuterium. In some embodiments, R 5 A 2 In some embodiments, R 5 Ar 1 In some embodiments, R 5 D 1 It is.

[0244] In some embodiments, X A is O. In some embodiments, X A is S. In some embodiments, X A is NR A’ It is.

[0245] In some embodiments, R A is hydrogen. In some embodiments, R A is deuterium. In some embodiments, R Ais a halogen. In some embodiments, R A is cyano. In some embodiments, R A is substituted or unsubstituted alkyl. In some embodiments, R A is substituted or unsubstituted alkoxy. In some embodiments, R A is substituted or unsubstituted aryl. In some embodiments, R A is substituted or unsubstituted aryloxy. In some embodiments, R A is substituted or unsubstituted heteroaryl. In some embodiments, R A is substituted or unsubstituted heteroaryloxy. In some embodiments, R A is silyl. In some embodiments, R A Two or more instances of together form a ring system.

[0246] In some embodiments, R A’ is hydrogen. In some embodiments, R A’ is deuterium. In some embodiments, R A’ is substituted or unsubstituted alkyl. In some embodiments, R A’ is substituted or unsubstituted aryl. In some embodiments, R A’ is substituted or unsubstituted heteroaryl. In some embodiments, R A’ and R A Two or more instances of together form a ring system.

[0247] In some embodiments, L A is a bond. In some embodiments, L A is substituted or unsubstituted arylene. In some embodiments, L Ais a substituted or unsubstituted heteroarylene. Each instance of arylene and heteroarylene may be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which may be joined together to form a ring system.

[0248] In some embodiments, D 1 teeth,

[0249] [ka]

[0250] In some embodiments, D 1 teeth,

[0251] [ka]

[0252] In some embodiments, D 1 teeth,

[0253] [ka]

[0254] In some embodiments, D 1 teeth,

[0255] [ka]

[0256] In some embodiments, D 1 teeth,

[0257] [ka]

[0258] It is.

[0259] In some embodiments, X D is O. In some embodiments, X D is S. In some embodiments, X D is NR D’ In some embodiments, X D is C(O). In some embodiments, X D is substituted or unsubstituted methylene. In some embodiments, X D is substituted or unsubstituted ethylene. In some embodiments, X D is substituted or unsubstituted vinylene. In some embodiments, X D is substituted or unsubstituted o-arylene. In some embodiments, X D is a substituted or unsubstituted o-heteroarylene. Each instance of methylene, ethylene, vinylene, o-arylene, or o-heteroarylene may be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.

[0260] In some embodiments, R D is hydrogen. In some embodiments, R D is deuterium. In some embodiments, R D is substituted or unsubstituted alkyl. In some embodiments, R D is substituted or unsubstituted alkoxy. In some embodiments, R D is substituted or unsubstituted amino. In some embodiments, R D is substituted or unsubstituted aryl. In some embodiments, R D is substituted or unsubstituted aryloxy. In some embodiments, R Dis substituted or unsubstituted heteroaryl. In some embodiments, R D is substituted or unsubstituted heteroaryloxy. In some embodiments, R D is silyl. In some embodiments, R D Two or more instances of together form a ring system.

[0261] In some embodiments, R D’ is hydrogen. In some embodiments, R D’ is deuterium. In some embodiments, R D’ is substituted or unsubstituted alkyl. In some embodiments, R D’ is substituted or unsubstituted aryl. In some embodiments, R D’ is substituted or unsubstituted heteroaryl. In some embodiments, R D’ and R D Two or more instances of together form a ring system.

[0262] In some embodiments, L D is a single bond. In some embodiments, L D is substituted or unsubstituted arylene. In some embodiments, L D is a substituted or unsubstituted heteroarylene. Each instance of arylene and heteroarylene may be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, two or more of which may be joined together to form a ring system.

[0263] In some embodiments, Ar 1 is substituted or unsubstituted aryl. In some embodiments, Ar 1is a substituted or unsubstituted heteroaryl that does not contain any nitrogen atoms. Each instance of aryl and heteroaryl may be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl that does not contain any nitrogen atoms, and two or more of these substituents may be joined together to form a ring system. In some embodiments, alkyl is C 1 ~C 20 It is an alkyl.

[0264] In some embodiments, Ar 1 teeth,

[0265] [ka]

[0266] where: R Ar is the point of attachment to formula (I), and the remaining R Ar is independently selected from hydrogen, deuterium, alkyl, or an alkyl substituted or unsubstituted aryl group.

[0267] In some embodiments, Ar 1 is aryl, C 6 ~C 40 In some embodiments, Ar 1 is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl.

[0268] In some embodiments, Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl.

[0269] In some embodiments, Ar 1 is heteroaryl, C2 ~C 40 It is heteroaryl.

[0270] In some embodiments, Ar 1 is alkoxy, C 1 ~C 20 It is an alkoxy.

[0271] In some embodiments, Ar 1 is aryloxy, C 6 ~C 40 It is aryloxy.

[0272] In some embodiments, Ar 1 is heteroaryloxy, C 2 ~C 40 It is heteroaryloxy.

[0273] In some embodiments, the compound of formula (I) has the formula (Ia):

[0274] [ka]

[0275] It is a compound of the formula:

[0276] In some embodiments, the compound of formula (I) has the formula (Ib):

[0277] [ka]

[0278] (In the formula, R L are independently selected from deuterium, alkyl or alkyl substituted aryl groups or unsubstituted aryl groups; and n is 0 to 4.

[0279] In some embodiments, the compound of formula (I) has the formula (Ic):

[0280] [ka]

[0281] (In the formula, R L are independently selected from deuterium, alkyl or alkyl substituted aryl groups or unsubstituted aryl groups; and n is 0 to 4.

[0282] In some embodiments, the compound has formula (II):

[0283] [ka]

[0284] (In the formula, A is,

[0285] [ka]

[0286] is selected from D is independently H, Me, Ph,

[0287] [ka]

[0288] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one occurrence of D is selected from D1-D31).

[0289] In some embodiments, A is CN. In some embodiments, A is A1. In some embodiments, A is A2. In some embodiments, A is A3. In some embodiments, A is A4. In some embodiments, A is A5. In some embodiments, A is A6. In some embodiments, A is A7. In some embodiments, A is A8. In some embodiments, A is A9. In some embodiments, A is A10.

[0290] In some embodiments, D is H. In some embodiments, at least one instance of D is H. In some embodiments, D is Me. In some embodiments, at least one instance of D is Me. In some embodiments, D is Ph. In some embodiments, at least one instance of D is Ph.

[0291] In some embodiments, D is D1. 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 D11. 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 D16. In some embodiments, D is D17. In some embodiments, D is D18. In some embodiments, D is D19. In some embodiments, 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. In some embodiments, D is D30. In some embodiments, D is D31.

[0292] In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7. In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13. In some embodiments, D is selected from D14, D15, and D16. In some embodiments, D is selected from D17, D18, and D19. In some embodiments, D is selected from D20, D21, D22, D23, and D24. In some embodiments, D is selected from D25, D26, and D27. In some embodiments, D is selected from D28, D29, D30, and D31.

[0293] In some embodiments, R is H. In some embodiments, R is Me. In some embodiments, R is Ph.

[0294] In some embodiments, both instances of R are different. In some embodiments, both instances of R are the same.

[0295] In some embodiments, each instance of D is different. In some embodiments, two instances of D are the same. In some embodiments, three instances of D are the same. In some embodiments, all instances of D are the same.

[0296] In some embodiments, two instances of D are independently selected from D1-D31. In some embodiments, three instances of D are independently selected from D1-D31. In some embodiments, all instances of D are independently selected from D1-D31.

[0297] In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is C(Ph) 2 In some embodiments, Z 1 is O. In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is N(Ph).

[0298] In some embodiments, Z 2 is H. In some embodiments, Z 2 is CN. In some embodiments, Z 2 (C 1 ~C 20 )-alkyl. In some embodiments, Z 2 is 5-30 membered aryl. In some embodiments, Z 2 is 3-30 membered heteroaryl. In some embodiments, Z 2is diarylamino. In some embodiments, diarylamino is -N(Ph) 2 It is.

[0299] In some embodiments, Z 2 The two instances of are the same. In some embodiments, Z 2 The two examples are different.

[0300] In some embodiments, the compound of formula (II) is selected from the following:

[0301] [Table 1] JPEG0007630185000081.jpg246170JPEG0007630185000082.jpg249170JPEG0007630185000083.jpg248170JPEG00076301850 00084.jpg249170JPEG0007630185000085.jpg246170JPEG0007630185000086.jpg249170JPEG0007630185000087.jpg245170

[0302] In some embodiments, the compound of formula (II) is

[0303] [ka] JPEG0007630185000089.jpg122170

[0304] is selected from.

[0305] In some embodiments, the compound of formula (II) is

[0306] [ka]

[0307] It is.

[0308] In some embodiments, the compound has formula (III):

[0309] [ka]

[0310] (In the formula, A is,

[0311] [ka]

[0312] is selected from D is independently

[0313] [ka]

[0314] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D has a structure selected from D1-D31).

[0315] In some embodiments, A is A1. In some embodiments, A is A2. In some embodiments, A is A3. In some embodiments, A is A4. In some embodiments, A is A5. In some embodiments, A is A6. In some embodiments, A is A7. In some embodiments, A is A8. In some embodiments, A is A9. In some embodiments, A is A10.

[0316] In some embodiments, A is selected from A1, A2, and A3. In some embodiments, A is selected from A4 and A5. In some embodiments, A is selected from A6 and A7. In some embodiments, A is selected from A8, A9, and A10.

[0317] In some embodiments, D is D1. 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 D11. 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 D16. In some embodiments, D is D17. In some embodiments, D is D18. In some embodiments, D is D19. In some embodiments, 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. In some embodiments, D is D30. In some embodiments, D is D31.

[0318] In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7. In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13. In some embodiments, D is selected from D14, D15, and D16. In some embodiments, D is selected from D17, D18, and D19. In some embodiments, D is selected from D20, D21, D22, D23, and D24. In some embodiments, D is selected from D25, D26, and D27. In some embodiments, D is selected from D28, D29, D30, and D31.

[0319] In some embodiments, R is H. In some embodiments, R is Me. In some embodiments, R is Ph.

[0320] In some embodiments, both instances of R are different. In some embodiments, both instances of R are the same.

[0321] In some embodiments, each instance of D is different. In some embodiments, two instances of D are the same. In some embodiments, three instances of D are the same. In some embodiments, all instances of D are the same.

[0322] In some embodiments, two instances of D are independently selected from D1-D31. In some embodiments, three instances of D are independently selected from D1-D31. In some embodiments, all instances of D are independently selected from D1-D31.

[0323] In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is C(Ph) 2 In some embodiments, Z 1 is O. In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is N(Ph).

[0324] In some embodiments, Z 2 is H. In some embodiments, Z 2 is CN. In some embodiments, Z 2 (C 1 ~C 20 )-alkyl. In some embodiments, Z 2 is 5-30 membered aryl. In some embodiments, Z 2 is 3-30 membered heteroaryl. In some embodiments, Z 2is diarylamino. In some embodiments, diarylamino is -N(Ph) 2 It is.

[0325] In some embodiments, Z 2 The two instances of are the same. In some embodiments, Z 2 The two examples are different.

[0326] In some embodiments, the compound of formula (III) is selected from the following:

[0327] [Table 2] JPEG0007630185000095.jpg255157JPEG0007630185000096.jpg255156JPEG0007630185000097.jpg255155JPEG00076301850 00098.jpg255154JPEG0007630185000099.jpg255154JPEG0007630185000100.jpg255154JPEG0007630185000101.jpg218170

[0328] In some embodiments, the compound of formula (III) is

[0329] [ka] JPEG0007630185000103.jpg227170JPEG0007630185000104.jpg238170JPEG0007630185000105.jpg70170

[0330] is selected from.

[0331] In some embodiments, the compound has formula (III):

[0332] [ka]

[0333] (In the formula, A is,

[0334] [ka]

[0335] is selected from D is independently H, deuterium, Ph,

[0336] [ka]

[0337] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31; At least one instance of D has the structure:

[0338] In some embodiments, A is A1. In some embodiments, A is A2. In some embodiments, A is A3. In some embodiments, A is A4. In some embodiments, A is A5. In some embodiments, A is A6. In some embodiments, A is A7. In some embodiments, A is A8. In some embodiments, A is A9. In some embodiments, A is A10.

[0339] In some embodiments, A is selected from A1, A2, and A3. In some embodiments, A is selected from A4 and A5. In some embodiments, A is selected from A6 and A7. In some embodiments, A is selected from A8, A9, and A10.

[0340] In some embodiments, D is H. In some embodiments, D is deuterium. In some embodiments, D is phenyl.

[0341] In some embodiments, D is D1. 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 D11. 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 D16. In some embodiments, D is D17. In some embodiments, D is D18. In some embodiments, D is D19. In some embodiments, 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. In some embodiments, D is D30. In some embodiments, D is D31.

[0342] In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7. In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13. In some embodiments, D is selected from D14, D15, and D16. In some embodiments, D is selected from D17, D18, and D19. In some embodiments, D is selected from D20, D21, D22, D23, and D24. In some embodiments, D is selected from D25, D26, and D27. In some embodiments, D is selected from D28, D29, D30, and D31.

[0343] In some embodiments, R is H. In some embodiments, R is Me. In some embodiments, R is Ph.

[0344] In some embodiments, both instances of R are different. In some embodiments, both instances of R are the same.

[0345] In some embodiments, each instance of D is different. In some embodiments, two instances of D are the same. In some embodiments, three instances of D are the same. In some embodiments, all instances of D are the same.

[0346] In some embodiments, two instances of D are independently selected from D1-D31. In some embodiments, three instances of D are independently selected from D1-D31.

[0347] In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is C(Ph) 2 In some embodiments, Z 1 is O. In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is N(Ph).

[0348] In some embodiments, Z 2 is H. In some embodiments, Z 2 is CN. In some embodiments, Z 2 (C 1 ~C 20 )-alkyl. In some embodiments, Z 2 is 5-30 membered aryl. In some embodiments, Z 2 is 3-30 membered heteroaryl. In some embodiments, Z 2 is diarylamino. In some embodiments, diarylamino is -N(Ph) 2 It is.

[0349] In some embodiments, Z 2 The two instances of are the same. In some embodiments, Z 2 The two examples are different.

[0350] In some embodiments, the compound of formula (III) is selected from the following:

[0351] [Table 3] JPEG0007630185000110.jpg243170JPEG0007630185000111.jpg246170JPEG0007630185000112.jpg245170JPEG000 7630185000113.jpg242170JPEG0007630185000114.jpg249170JPEG0007630185000115.jpg242170JPEG00076301850 00116.jpg246170JPEG0007630185000117.jpg246170JPEG0007630185000118.jpg248170JPEG0007630185000119.j pg244170JPEG0007630185000120.jpg242170JPEG0007630185000121.jpg247170JPEG0007630185000122.jpg105170

[0352] In some embodiments, the compound of formula (III) is

[0353] [ka] JPEG0007630185000124.jpg250170JPEG0007630185000125.jpg154170JPEG0007630185000126.jpg249170JPEG0007630185000127.jpg175170

[0354] is selected from.

[0355] In some embodiments, the compound of formula (III) is

[0356] [ka] JPEG0007630185000129.jpg255151JPEG0007630185000130.jpg66170

[0357] is selected from.

[0358] In some embodiments, the compound has formula (IV):

[0359] [ka]

[0360] (In the formula, A is,

[0361] [ka]

[0362] is selected from D is independently

[0363] [ka]

[0364] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D has a structure selected from D1-D31).

[0365] In some embodiments, A is A1. In some embodiments, A is A2. In some embodiments, A is A3. In some embodiments, A is A4. In some embodiments, A is A5. In some embodiments, A is A6. In some embodiments, A is A7. In some embodiments, A is A8. In some embodiments, A is A9. In some embodiments, A is A10.

[0366] In some embodiments, A is selected from A1, A2, and A3. In some embodiments, A is selected from A4 and A5. In some embodiments, A is selected from A6 and A7. In some embodiments, A is selected from A8, A9, and A10.

[0367] In some embodiments, D is D1. 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 D11. 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 D16. In some embodiments, D is D17. In some embodiments, D is D18. In some embodiments, D is D19. In some embodiments, 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. In some embodiments, D is D30. In some embodiments, D is D31.

[0368] In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7. In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13. In some embodiments, D is selected from D14, D15, and D16. In some embodiments, D is selected from D17, D18, and D19. In some embodiments, D is selected from D20, D21, D22, D23, and D24. In some embodiments, D is selected from D25, D26, and D27. In some embodiments, D is selected from D28, D29, D30, and D31.

[0369] In some embodiments, R is H. In some embodiments, R is Me. In some embodiments, R is Ph.

[0370] In some embodiments, both instances of R are different. In some embodiments, both instances of R are the same.

[0371] In some embodiments, each instance of D is different. In some embodiments, two instances of D are the same. In some embodiments, three instances of D are the same. In some embodiments, all instances of D are the same.

[0372] In some embodiments, two instances of D are independently selected from D1-D31. In some embodiments, three instances of D are independently selected from D1-D31. In some embodiments, all instances of D are independently selected from D1-D31.

[0373] In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is C(Ph) 2 In some embodiments, Z 1 is O. In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is N(Ph).

[0374] In some embodiments, Z 2 is H. In some embodiments, Z 2 is CN. In some embodiments, Z 2 (C 1 ~C 20 )-alkyl. In some embodiments, Z 2 is 5-30 membered aryl. In some embodiments, Z 2 is 3-30 membered heteroaryl. In some embodiments, Z 2is diarylamino. In some embodiments, diarylamino is -N(Ph) 2 It is.

[0375] In some embodiments, Z 2 The two instances of are the same. In some embodiments, Z 2 The two examples are different.

[0376] In some embodiments, the compound of formula (IV) is selected from the following:

[0377] [Table 4] JPEG0007630185000135.jpg244170JPEG0007630185000136.jpg245170JPEG0007630185000137.jpg246170JPEG0007630185000138.jpg25017 0JPEG0007630185000139.jpg248170JPEG0007630185000140.jpg245170JPEG0007630185000141.jpg248170JPEG0007630185000142.jpg29170

[0378] In some embodiments, the compound of formula (IV) is

[0379] [ka] JPEG0007630185000144.jpg244170JPEG0007630185000145.jpg226170JPEG0007630185000146.jpg148170

[0380] is selected from.

[0381] In some embodiments, the compound has formula (IV):

[0382] [ka]

[0383] (In the formula, A is,

[0384] [ka]

[0385] is selected from D is independently H, deuterium, Ph,

[0386] [ka] JPEG0007630185000150.jpg126170

[0387] is selected from R is independently selected from H, Me, and Ph; Z 1 are independently C(CH 3 ) 2 , C(Ph) 2 , O and N(Ph); Z 2 are independently H, CN, (C 1 ~C 20 )-alkyl, 5- to 30-membered aryl, 3- to 30-membered heteroaryl, and diarylamino; At least one instance of D is selected from D1-D31; At least one instance of D is selected from H, Ph, or deuterium.

[0388] In some embodiments, A is A1. In some embodiments, A is A2. In some embodiments, A is A3. In some embodiments, A is A4. In some embodiments, A is A5. In some embodiments, A is A6. In some embodiments, A is A7. In some embodiments, A is A8. In some embodiments, A is A9. In some embodiments, A is A10.

[0389] In some embodiments, A is selected from A1, A2, and A3. In some embodiments, A is selected from A4 and A5. In some embodiments, A is selected from A6 and A7. In some embodiments, A is selected from A8, A9, and A10.

[0390] In some embodiments, D is H. In some embodiments, D is deuterium. In some embodiments, D is phenyl.

[0391] In some embodiments, D is D1. 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 D11. 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 D16. In some embodiments, D is D17. In some embodiments, D is D18. In some embodiments, D is D19. In some embodiments, 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. In some embodiments, D is D30. In some embodiments, D is D31.

[0392] In some embodiments, D is selected from D1, D2, D3, D4, D5, D6, and D7. In some embodiments, D is selected from D8, D9, D10, D11, D12, and D13. In some embodiments, D is selected from D14, D15, and D16. In some embodiments, D is selected from D17, D18, and D19. In some embodiments, D is selected from D20, D21, D22, D23, and D24. In some embodiments, D is selected from D25, D26, and D27. In some embodiments, D is selected from D28, D29, D30, and D31.

[0393] In some embodiments, R is H. In some embodiments, R is Me. In some embodiments, R is Ph.

[0394] In some embodiments, both instances of R are different. In some embodiments, both instances of R are the same.

[0395] In some embodiments, each instance of D is different. In some embodiments, two instances of D are the same. In some embodiments, three instances of D are the same.

[0396] In some embodiments, two instances of D are independently selected from D1-D31. In some embodiments, three instances of D are independently selected from D1-D31. In some embodiments, all instances of D are independently selected from D1-D31.

[0397] In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is C(Ph) 2 In some embodiments, Z 1 is O. In some embodiments, Z 1 is C(CH 3 ) 2 In some embodiments, Z 1 is N(Ph).

[0398] In some embodiments, Z 2 is H. In some embodiments, Z 2 is CN. In some embodiments, Z 2 (C 1 ~C 20 )-alkyl. In some embodiments, Z 2 is 5-30 membered aryl. In some embodiments, Z 2 is 3-30 membered heteroaryl. In some embodiments, Z 2is diarylamino. In some embodiments, diarylamino is -N(Ph) 2 It is.

[0399] In some embodiments, Z 2 The two instances of are the same. In some embodiments, Z 2 The two examples are different.

[0400] In some embodiments, the compound of formula (IV) is selected from the following:

[0401] [Table 5] JPEG0007630185000152.jpg245170JPEG0007630185000153.jpg247170JPEG0007630185000154.j pg250170JPEG0007630185000155.jpg247170JPEG0007630185000156.jpg245170JPEG0007630185 000157.jpg245170JPEG0007630185000158.jpg245170JPEG0007630185000159.jpg246170JPEG00 07630185000160.jpg243170JPEG0007630185000161.jpg245170JPEG0007630185000162.jpg71170

[0402] In some embodiments, the compound of formula (IV) is

[0403] [ka] JPEG0007630185000164.jpg255154JPEG0007630185000165.jpg250170

[0404] is selected from.

[0405] In some embodiments, the compound of formula (IV) is

[0406] [ka] JPEG0007630185000167.jpg116170

[0407] is selected from.

[0408] In some embodiments, the compound of formula (IV) is

[0409] [ka]

[0410] It is.

[0411] In some embodiments, the compounds of Formula (I), Formula (II), Formula (III), or Formula (IV) are substituted with deuterium.

[0412] In some embodiments, the compound of Formula (I), Formula (II), Formula (III), or Formula (IV) is an emissive material.

[0413] In some embodiments, the compounds of formula (I), formula (II), formula (III), or formula (IV) can emit delayed fluorescence.

[0414] In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I), Formula (II), Formula (III), or Formula (IV) can emit light in the 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 nm to about 700 nm), or the near infrared region.

[0415] In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I), Formula (II), Formula (III) or Formula (IV) can emit light in the red or orange region of the visible spectrum (e.g., from about 620 nm to about 780 nm, about 650 nm).

[0416] In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I), Formula (II), Formula (III), or Formula (IV) can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm).

[0417] In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I), Formula (II), Formula (III) or Formula (IV) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm).

[0418] In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I), Formula (II), Formula (III) or Formula (IV) can emit light in the blue region of the visible spectrum (e.g., from about 400 nm to about 490 nm, about 475 nm).

[0419] The electronic properties of libraries of small chemical molecules can be calculated using known ab initio quantum mechanical calculations. For example, 6-31G as a basis set. * Time-dependent density functional theory (TD-DFT / B3LYP / 6-31G) using a set of functions known as and Becke's three-parameter Lee-Yang-Parr hybrid functional for solving the Hartree-Fock equation. * ) can be used to screen for molecular fragments (moieties) that have a HOMO above a certain threshold and a LUMO below a certain threshold, where the calculated triplet state of said moieties is above 2.75 eV.

[0420] Thus, for example, the donor moiety ("D") can be selected because it has a HOMO energy (e.g., ionization potential) of -6.5 eV or greater. For example, the acceptor moiety ("A") can be selected because it has a LUMO energy (e.g., electron affinity) of -0.5 eV or less. The linker moiety ("L") can be, for example, a rigid conjugated system that can sterically restrict the acceptor and donor moieties into particular configurations, thereby preventing overlap between the conjugated pi-systems of the donor and acceptor moieties.

[0421] In some embodiments, the compound library has the following properties: 1. Emission at a specific wavelength 2. Calculated triplet states above a particular energy level, 3. ΔE below a certain value ST value, 4. Quantum yield above a certain value; 5. HOMO level, and 6.LUMO Level are filtered using one or more of the following:

[0422] In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ST ) 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, ΔE ST The 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.

[0423] In some embodiments, the compounds of Formula (I), Formula (II), Formula (III) or Formula (IV) exhibit a quantum yield of greater than 25%, e.g., 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.

[0424] Compositions Having the Disclosed Compounds In some embodiments, a compound of formula (I), formula (II), formula (III) or formula (IV) is combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) to form a solid-state coating or layer by dispersing within, covalently bonding to, coating with, forming on, or associating with the material. For example, a compound of formula (I), formula (II), formula (III) or formula (IV) can be combined with an electroactive material to form a coating. In some cases, a compound of formula (I), formula (II), formula (III) or formula (IV) can be combined with a hole transport polymer. In some cases, a compound of formula (I), formula (II), formula (III) or formula (IV) can be combined with an electron transport polymer. In some cases, a compound of formula (I), formula (II), formula (III) or formula (IV) can be combined with a hole transport polymer and an electron transport polymer. In some cases, a compound of Formula (I), Formula (II), Formula (III), or Formula (IV) can be combined with a copolymer that includes both hole transport and electron transport moieties. In such embodiments, electrons and / or holes formed within the solid coating or layer can interact with the compound of Formula (I), Formula (II), Formula (III), or Formula (IV).

[0425] Exemplary Uses of the Disclosed Compounds Organic Light Emitting Diode One aspect of the present invention relates to the use of a compound of formula (I), formula (II), formula (III) or formula (IV) of the present invention as a light-emitting material of an organic light-emitting device. In some embodiments, a compound represented by formula (I), formula (II), formula (III) or formula (IV) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In some embodiments, a compound of formula (I), formula (II), formula (III) or formula (IV) includes a delayed fluorescent material (delayed fluorescent emitter) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent emitter having a structure of formula (I), formula (II), formula (III) or formula (IV). In some embodiments, the present invention relates to the use of a compound of formula (I), formula (II), formula (III) or formula (IV) as a delayed fluorescent emitter. In some embodiments, the light-emitting layer includes a compound of formula (I), formula (II), formula (III) or formula (IV) as an auxiliary dopant.

[0426] In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) can be used as a host material and can be used together with one or more emitting materials, and the emitting materials can be fluorescent materials, phosphorescent materials or TADF materials. In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) can be used as a hole transport material. In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) can be used as an electron transport material. In some embodiments, the present invention relates to a method of emitting delayed fluorescence from the compound of formula (I), formula (II), formula (III) or formula (IV). In some embodiments, an organic light-emitting device comprising the compound as an emitting material emits delayed emission and has high luminous efficiency.

[0427] In some embodiments, the light-emitting layer comprises a compound of formula (I), formula (II), formula (III) or formula (IV), wherein the compound of formula (I), formula (II), formula (III) or formula (IV) is oriented parallel to the substrate. In some embodiments, the substrate is a coating surface. In some embodiments, the orientation of the compound of formula (I), formula (II), formula (III) or formula (IV) relative to the coating surface affects or dictates the propagation direction of the light emitted by the aligned compound. In some embodiments, the alignment of the propagation direction of the light emitted by the compound of formula (I), formula (II), formula (III) or formula (IV) enhances the light extraction efficiency from the light-emitting layer.

[0428] One aspect of the present invention relates to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emitting layer. In some embodiments, the emitting layer comprises a compound of formula (I), formula (II), formula (III) or formula (IV) as an emitting material. In some embodiments, the organic light-emitting device is an organic photoluminescent device (organic PL device). In some embodiments, the organic light-emitting device is an organic electroluminescent device (organic EL device). In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) assists the emission of another emitting material contained in the emitting layer, i.e. as a so-called auxiliary dopant. In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) contained in the emitting layer exists at its lowest excited singlet energy level, which energy level is between the lowest excited singlet energy level of the host material contained in the emitting layer and the lowest singlet energy level of another emitting material contained in the emitting layer.

[0429] In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least one light-emitting layer. In some embodiments, the organic layer includes only one light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection layer and a hole transport layer with a hole injection function, and the electron transport layer may be an electron injection layer and an electron transport layer with an electron injection function. An example of an organic electroluminescent device is shown in FIG. 1.

[0430] substrate In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, where the substrate is not particularly limited and may be any substrate commonly used in organic electroluminescent devices, such as substrates formed from glass, transparent plastic, quartz, and silicon.

[0431] anode In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, an electrically conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or electrically conductive compound has a large work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the electrically conductive transparent material is CuI, indium tin oxide (ITO), SnO 2 and ZnO. In some embodiments, IDIXO(In 2 O 3Amorphous materials capable of forming a transparent electrically conductive coating, such as ZnO, are used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is made by deposition or sputtering. In some embodiments, the thin film is patterned by photolithography. In some embodiments, where the pattern does not require high accuracy (e.g., about 100 μm or more), the patterning can be performed using a mask having a desired shape in the deposition or sputtering of the electrode material. In some embodiments, wet deposition methods such as printing and coating methods are used where materials such as electrically conductive organic compounds can be applied as a coating. In some embodiments, the anode has a transmittance of more than 10% when the emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per square or less. In some embodiments, the thickness of the anode is 10 nm to 1000 nm. In some embodiments, the thickness of the anode is 10 nm to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0432] cathode In some embodiments, the cathode is made of an electrode material, i.e., a metal (called an electron-injecting metal) with a small work function (4 eV or less), an alloy, an electrically conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-copper mixture, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al 2 O 3 ) mixture, indium, lithium-aluminum mixture, and rare earth metals. In some embodiments, a mixture of an electron-injecting metal and a second metal is used that is a stable metal having a work function greater than that of the electron-injecting metal. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al 2 O 3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture enhances electron injection properties and durability against oxidation. In some embodiments, the cathode is fabricated by depositing the electrode material into a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per square or less. In some embodiments, the cathode has a thickness in the range of 10 nm to 5 μm. In some embodiments, the cathode has a thickness in the range of 50 nm to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semi-transparent to transmit the emitted light. In some embodiments, the transparent or semi-transparent electroluminescent device enhances the luminance of the emitted light.

[0433] In some embodiments, the cathode is formed using an electrically conductive, transparent material, as described for the anode, to form a transparent or semi-transparent cathode, hi some embodiments, the device includes an anode and a cathode that are both transparent or semi-transparent.

[0434] Emitting layer In some embodiments, the light-emitting layer is the layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, this layer emits light.

[0435] In some embodiments, the light-emitting layer is used as the light-emitting layer alone. In some embodiments, the light-emitting layer contains a light-emitting material and a host material. In some embodiments, the light-emitting material is one or more compounds of formula (I), formula (II), formula (III) or formula (IV). In some embodiments, in order for the organic electroluminescent device and the organic photoluminescent device to show high luminous efficiency, the singlet excitons and triplet excitons generated in the light-emitting material are trapped in the light-emitting material. In some embodiments, in addition to the light-emitting material, a host material is used in the light-emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has an excited singlet energy and an excited triplet energy, at least one of which is higher than the energy of the light-emitting material of the present invention. In some embodiments, the singlet excitons and triplet excitons generated in the light-emitting material of the present invention are trapped in the molecules of the light-emitting material of the present invention. In some embodiments, the singlet excitons and triplet excitons are sufficiently trapped to bring out the luminous efficiency. In some embodiments, even if singlet and triplet excitons are not fully confined, high luminous efficiency can still be obtained, so host materials that can achieve high luminous efficiency can be used in the present invention without any particular restrictions. In some embodiments, luminescence occurs in the luminescent material of the luminescent layer in the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound of formula (I), formula (II), formula (III) or formula (IV) and light emitted from the host material. In some embodiments, TADF molecules and host materials are used. In some embodiments, TADF is an auxiliary dopant.

[0436] In some embodiments, when a light-emitting material is used, the amount of the compound of the present invention as a 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 present invention as a 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 present invention as a 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 present invention as a 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 present invention as a light-emitting material contained in the light-emitting layer is 10% by weight or less.

[0437] In some embodiments, the host material in the light-emitting layer is an organic compound that has hole transport and electron transport functions. In some embodiments, the host material in the light-emitting layer is an organic compound that prevents the wavelength of the emitted light from increasing. In some embodiments, the host material in the light-emitting layer is an organic compound that has a high glass transition temperature.

[0438] In some embodiments, the host material is

[0439] [ka] JPEG0007630185000170.jpg255105JPEG0007630185000171.jpg241170

[0440] is selected from the group consisting of:

[0441] injection layer The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and increases the luminance of the light emitted. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer may be disposed between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. In some embodiments, the injection layer is present. In some embodiments, the injection layer is not present.

[0442] Barrier Layer A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing out of the light-emitting layer. In some embodiments, an electron barrier layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole barrier layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, the barrier layer prevents excitons from diffusing out of the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer are exciton barrier layers. As used herein, the term "electron barrier layer" or "exciton barrier layer" includes layers that have the functions of both an electron barrier layer and an exciton barrier layer.

[0443] Hole blocking layer The hole blocking layer acts as an electron transport layer. In some embodiments, the hole blocking layer transports electrons while preventing holes from reaching the electron transport layer. In some embodiments, the hole blocking layer increases the recombination probability of electrons and holes in the light-emitting layer. The materials for the hole blocking layer can be the same materials as those described for the electron transport layer.

[0444] [ka]

[0445] Electron Barrier Layer The electron blocking layer transports holes. In some embodiments, the electron blocking layer transports holes while preventing electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the recombination probability of electrons and holes in the light-emitting layer. Next, preferred examples of compounds that can be used as the electron blocking material are listed below.

[0446] [ka]

[0447] Exciton blocking layer The exciton blocking layer prevents excitons generated by the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the light-emitting layer. In some embodiments, the light-emitting efficiency of the device is enhanced. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side, and on both sides. In some embodiments where the exciton blocking layer is on the anode side, the exciton blocking layer may be adjacent to the light-emitting layer between the hole transport layer and the light-emitting layer. In some embodiments where the exciton blocking layer is on the cathode side, the exciton blocking layer may be adjacent to the light-emitting layer between the light-emitting layer and the cathode. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is between the anode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light emitting layer on the cathode side. In some embodiments, the exciton blocking layer has an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy, respectively, of the light emitting material.

[0448] Hole transport layer The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer is multiple layers.

[0449] In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used herein include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and electrically conductive polymeric oligomers, particularly thiophene oligomers, or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Next, preferred examples of compounds that can be used as the hole transport material are given below.

[0450] [ka] JPEG0007630185000175.jpg255118JPEG0007630185000176.jpg255147

[0451] electron transport layer The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer is multiple layers.

[0452] In some embodiments, the electron transport material only needs to have the function of transporting electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used herein include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Next, preferred examples of compounds that can be used as electron transport materials are listed below.

[0453] [ka] JPEG0007630185000178.jpg255151

[0454] molecular weight The molecular weight of the compound represented by formula (I), formula (II), formula (III) or formula (IV) is preferably 1500 daltons or less, more preferably 1200 daltons or less, even more preferably 1000 or less, and still more preferably 900 or less, for example, when the compound is used by forming an organic layer containing the compound represented by formula (I), formula (II), formula (III) or formula (IV) according to a vapor deposition method.

[0455] polymer The compound of formula (I), formula (II), formula (III) or formula (IV) can be formed into a film according to the coating method regardless of the molecular weight of the compound. Therefore, even a compound having a relatively large molecular weight can be formed into a film.

[0456] In some embodiments, the coating comprises a plurality of independently selected compounds of formula (I), formula (II), formula (III) or formula (IV). In some embodiments, the compounds of formula (I), formula (II), formula (III) or formula (IV) are modified to include a polymerizable group. The modified compounds are then polymerized to obtain a polymer comprising the compounds of formula (I), formula (II), formula (III) or formula (IV). For example, a monomer is obtained by replacing any one of the hydrogens of the compounds of formula (I), formula (II), formula (III) or formula (IV) with a polymerizable functional group. The monomer is then homopolymerized or copolymerized with any other monomer to obtain a polymer having repeating units. Alternatively, different compounds of formula (I), formula (II), formula (III) or formula (IV) are coupled to obtain a dimer or trimer. Examples of polymers having repeating units containing a compound of formula (I), formula (II), formula (III) or formula (IV) include polymers having a repeating unit containing a compound of formula (A) or formula (B):

[0457] [ka]

[0458] (In the formula, Q represents a group containing a compound of formula (I), formula (II), formula (III) or formula (IV); L 1 and L 2 each represents a linking group, R 101 , R 102 , R 103 and R 104 each independently represents a substituent.

[0459] In some embodiments, the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10 carbons. 11 -L 11 -(in the formula, X 11 is oxygen or sulfur, and L 11 represents a linking group).

[0460] In some embodiments, X 11 is oxygen. In some embodiments, L 11 is a substituted or unsubstituted alkylene or a substituted or unsubstituted arylene. In some embodiments, the substituted or unsubstituted alkylene is 1 ~C 10 In some embodiments, the substituted or unsubstituted arylene is substituted or unsubstituted phenylene.

[0461] In some embodiments, 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. 101 , R 102 , R 103 and R 104 are independently an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom. 101 , R 102 , R 103 and R 104 is independently an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms.

[0462] L 1 and L 2 can be introduced by replacing any one hydrogen in the structure of formula (I), formula (II), formula (III) or formula (IV). Two or more linking groups can be bonded to one Q to form a crosslinked structure or a network structure.

[0463] Specific structural examples of the repeating unit include those represented by the following formulae (C) to (F):

[0464] [ka]

[0465] The structure includes a structure represented by:

[0466] The polymer having the repeating units of formula (C) to formula (F) can be prepared by replacing any one hydrogen atom in the structure of formula (I), formula (II), formula (III) or formula (IV) with a hydroxy group, and then adding the following compound to the structure:

[0467] [ka]

[0468] The compound can be synthesized by introducing a polymerizable group via the hydroxy group which functions as a linker by a reaction with any one of the following compounds, and polymerizing the polymerizable group.

[0469] The polymer having the structure represented by formula (I), formula (II), formula (III) or formula (IV) may be a polymer containing a repeat unit having the structure represented by formula (I), formula (II), formula (III) or formula (IV) alone, or a polymer containing a repeat unit having any other structure. The repeat unit having the structure represented by formula (I), formula (II), formula (III) or formula (IV) contained in the polymer may be one type of repeat unit alone, or may contain two or more types of repeat units. The repeat unit not having the structure represented by formula (I), formula (II), formula (III) or formula (IV) includes a repeat unit derived from a monomer to be used in normal copolymerization. For example, there are the above-mentioned repeat units derived from a monomer having an ethylenically unsaturated bond such as ethylene, styrene, etc.

[0470] In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) is included in the light-emitting layer of the device of the present invention. In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) is included in the light-emitting layer and at least one other layer. In some embodiments, for each layer, the compound of formula (I), formula (II), formula (III) or formula (IV) is independently selected. In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) is the same. In some embodiments, the compound of formula (I), formula (II), formula (III) or formula (IV) is different. For example, the compound represented by formula (I), formula (II), formula (III) or formula (IV) can be used in injection layer, blocking layer, hole blocking layer, electron blocking layer, exciton blocking layer, hole transport layer, electron transport layer and similar layers mentioned above. The coating method of the above layer is not particularly limited, and the layer can be made by any dry process and / or wet process.

[0471] Specific examples of materials that can be used in organic electroluminescent devices are given above, but the materials that can be used in the present invention are not intended to be limited to the exemplified compounds. In some embodiments, a material with a specific function can also have another function.

[0472] Film formation method The compounds of the present invention can be formed as a coating on a substrate by any method.

[0473] Before forming the coating, the substrate can be heated or cooled, and the coating quality and molecular packing in the coating can be controlled by changing the temperature of the substrate. The temperature of the substrate is not particularly limited, and is preferably in the range of 0°C to 200°C, more preferably in the range of 15°C to 100°C, and particularly preferably in the range of 20°C to 95°C.

[0474] Prior to forming a coating of the compound of the present invention on a substrate, the coating can be formed by vacuum or solution techniques, both of which are preferred.

[0475] Specific examples of film formation by a vacuum method include vacuum deposition, sputtering, ion plating, and physical vapor deposition such as molecular beam epitaxy (MBE), and chemical vapor deposition (CVD) such as plasma polymerization, with vacuum deposition being preferred.

[0476] The film formation by the solution method means a method of dissolving an organic compound in a solvent capable of dissolving it, and forming a film by using the obtained solution.Specific examples thereof include ordinary methods, such as coating methods such as casting, dip coating, die coating, roll coating, bar coating and spin coating, printing methods such as inkjet, screen printing, gravure printing, flexographic printing, offset printing and microcontact printing, and Langmuir-Blodgett (LB) method, and the casting method, spin coating method, inkjet, gravure printing, flexographic printing, offset printing and microcontact printing are preferably used.

[0477] Coating solutions for the organic semiconductor devices of the present invention that can be used for solution-based coating are described below.

[0478] When forming a film on a substrate by a solution method, the material forming the layer is dissolved in an appropriate organic solvent (for example, a hydrocarbon solvent such as hexane, octane, decane, toluene, xylene, mesitylene, ethylbenzene, decalin, and 1-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, dichlorobenzene, and chlorotoluene; an ester solvent such as ethyl acetate, butyl acetate, and amyl acetate; methanol, ethanol, propanol, butanol, pentanol, heptane, etc.). A coating solution is prepared by dissolving or dispersing the compound in an alcohol solvent such as xanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, and ethylene glycol, an ether solvent such as diethyl ether, dibutyl ether, tetrahydrofuran, dioxane, and anisole, an amide solvent or an imide solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, 1-methyl-2-pyrrolidone, and 1-methyl-2-imidazolidinone, a sulfoxide solvent such as dimethyl sulfoxide, and a nitrile solvent such as acetonitrile) and / or water, and then the coating solution is coated by various coating methods to form a thin film.

[0479] device In some embodiments, the compounds of the present disclosure are incorporated into devices, including, but not limited to, OLED light bulbs, OLED lamps, television screens, computer monitors, cell phones, and tablets.

[0480] In some embodiments, the electronic device is an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A host material, A compound of formula (I), (II), (III) or (IV), Including, OLEDs.

[0481] In some embodiments, the light-emitting layer comprises a compound of Formula (I), Formula (II), Formula (III), or Formula (IV) as the light-emitting material.

[0482] In some embodiments, the light-emitting layer comprises a compound of Formula (I), Formula (II), Formula (III), or Formula (IV) as a co-dopant.

[0483] In some embodiments, the emissive layer of the OLED further comprises a fluorescent material, where a compound of Formula (I), Formula (II), Formula (III), or Formula (IV) converts a triplet to a singlet with respect to the fluorescent emitter.

[0484] In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLED or photovoltaic devices.In some embodiments, the compositions can be useful in facilitating charge or energy transfer within the device and / or as hole transport materials.The device can be, for example, an organic light-emitting diode (OLED), an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic photodetector, an organic photoreceptor, an organic field quencher (O-FQD), a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser).

[0485] Light bulb or lamp In some embodiments, the electronic device is an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A host material, A compound of formula (I), (II), (III) or (IV), an OLED comprising the compound of formula (I), (II), (III) or (IV) above as the light-emitting material; OLED driving circuit, Equipped with.

[0486] In some embodiments, the light-emitting layer comprises a compound of Formula (I), Formula (II), Formula (III), or Formula (IV) as a co-dopant.

[0487] In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a color combination that is not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-, four-, or more-color combination.

[0488] In some embodiments, the device comprises: a circuit board having a first side with a mounting surface and an opposing second side, the circuit board defining at least one opening; The device is configured to emit light and includes an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode, the emissive layer comprising: A host material, A compound of formula (I), (II), (III) or (IV), at least one OLED on said mounting surface, comprising: a housing for the circuit board; at least one connector disposed at an end of the housing; wherein the housing and the connector define a package adapted for installation in a lighting fixture.

[0489] In some embodiments, the light-emitting layer comprises a compound of Formula (I), Formula (II), Formula (III), or Formula (IV) as a co-dopant.

[0490] In some embodiments, the OLED light includes multiple OLEDs mounted on a circuit board to emit light in multiple directions. In some embodiments, a portion of the light emitted in a first direction is deflected to emit in a second direction. In some embodiments, a reflector is used to deflect the light emitted in the first direction.

[0491] Display or Screen In some embodiments, the compounds of formula (I), formula (II), formula (III) or formula (IV) can be used in a screen or display. In some embodiments, the compounds of formula (I), formula (II), formula (III) or formula (IV) are deposited on a substrate using methods including, but not limited to, vacuum evaporation, deposition, vapor deposition or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for double-sided etching, providing pixels with unique aspect ratios. In the manufacturing method of an OLED display, a screen (which may also be referred to as a mask) is used. The corresponding artwork pattern design facilitates very steep and narrow tie bars between pixels in the vertical direction and large and wide bevel openings in the horizontal direction. This allows for the fine patterning of pixels required for high resolution displays while optimizing chemical deposition on the TFT backplane.

[0492] Internal patterning of the pixel allows the construction of three-dimensional pixel openings with different aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles within the pixel area constrains etching in certain areas until these particular patterns are undercut and lift off the substrate. At that point, the entire pixel area is under a similar etch rate, but the depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows the etching to be constrained at different rates within the pixel, allowing the localized deeper etching required to create the steep vertical bevel.

[0493] The preferred material for the deposition mask is Invar. Invar is a metal alloy that is cold rolled into long sheets in steel mills. Invar cannot be electrodeposited as a nickel mask onto a rotating mandrel. The preferred and more cost-effective method for forming the open areas in the mask used for deposition is by wet chemical etching.

[0494] In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and electron beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0495] Methods for Making Devices Using the Disclosed Compounds OLED displays are generally manufactured by forming a large mother panel and cutting the mother panel into cell panels. In general, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) including an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and a sealing layer, and then cutting it from the mother panel.

[0496] OLED displays are generally manufactured by forming a large mother panel and cutting the mother panel into cell panels. In general, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) including an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and a sealing layer, and then cutting it from the mother panel.

[0497] In another aspect, provided herein is a method for manufacturing an organic light emitting diode (OLED) display, comprising the steps of: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in units of cell panels; forming a sealing layer on each display unit of the cell panel; applying an organic coating to the interface between said cell panels; A method is provided, comprising:

[0498] In some embodiments, the barrier layer is an inorganic film made of, for example, SiNx, and the ends of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film is useful for flexibly cutting the mother panel into cell panels.

[0499] In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode and a source / drain electrode. Each of the multiple 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, and the organic coating applied to the boundary is made of the same material as the planarization film and is formed at the same time as the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer, with a passivation layer and a planarization film between them, and an encapsulation layer covering and protecting the light-emitting unit. In some embodiments of the manufacturing method, the organic coating does not contact either the display unit or the encapsulation layer.

[0500] Each of the organic coating and the planarization film may include one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic coating. In some embodiments, the base substrate may be formed from polyimide. The method includes attaching a carrier substrate formed from a glass material to one surface of the base substrate before forming the barrier layer on the other surface of the base substrate formed from polyimide, and separating the carrier substrate from the base substrate before cutting along the border. In some embodiments, the OLED display is a flexible display.

[0501] In some embodiments, the passivation layer is an organic coating disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic coating formed on the passivation layer. In some embodiments, the planarization film is formed from polyimide or acrylic, as is the organic coating formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic coating are formed simultaneously when the OLED display is manufactured. In some embodiments, the organic coating can be formed on the edge of the barrier layer such that a portion of the organic coating directly contacts the base substrate, and the remaining portion of the organic coating contacts the barrier layer while surrounding the edge of the barrier layer.

[0502] In some embodiments, 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, In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer.

[0503] In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, and the organic light-emitting layer emits light to form an image. Hereinafter, the image-forming unit including the TFT layer and the light-emitting unit is referred to as a display unit portion.

[0504] In some embodiments, the sealing layer that covers the display unit and prevents the intrusion of external moisture may be formed to have a thin film sealing structure in which organic coatings and inorganic coatings are alternately stacked. In some embodiments, the sealing layer has a thin film sealing structure in which a plurality of thin films are stacked. In some embodiments, the organic coating applied to the boundary portion is spaced apart from each of the plurality of display units. In some embodiments, the organic coating is formed such that a portion of the organic coating directly contacts the base substrate and the remaining portion of the organic coating contacts the barrier layer while surrounding the edge of the barrier layer.

[0505] In one embodiment, the OLED display is flexible and uses a soft base substrate formed from polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed from a glass material, and the carrier substrate is then separated.

[0506] In some embodiments, the barrier layer is formed on a surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, the base substrate is formed over the entire surface of the mother panel, while the barrier layer is formed according to the size of each cell panel, so that a groove is formed at the boundary between the barrier layers of the cell panels. Each cell panel can be cut along the groove.

[0507] In some embodiments, the manufacturing method further includes cutting along the boundary, in which a groove is formed in the barrier layer, and at least a portion of the organic film is formed in the groove, and the groove does not penetrate to the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on the TFT layer so as to cover the TFT layer. At the same time as the planarization film, which is made of, for example, polyimide or acrylic, is formed, the groove at the boundary is covered with an organic film, which is made of, for example, polyimide or acrylic. This is to prevent cracks from occurring by absorbing the impact generated when each cell panel is cut along the groove at the boundary with the organic film. That is, if the entire barrier layer is entirely exposed without the organic film, the impact generated when each cell panel is cut along the groove at the boundary is transmitted to the barrier layer, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the boundaries between the barrier layers are covered with an organic coating, and the organic coating absorbs the shock that would otherwise be transmitted to the barrier layers, so that each cell panel can be cut flexibly and the barrier layers can be prevented from cracking. In one embodiment, the organic coating covering the grooves at the boundaries and the planarizing film are spaced apart from each other. For example, when the organic coating and the planarizing film are connected to each other as one layer, external moisture may penetrate into the display unit through the part where the planarizing film and the organic coating are retained, so that the organic coating and the planarizing film are spaced apart from each other to separate the organic coating from the display unit.

[0508] In some embodiments, the display unit is formed by forming a light-emitting unit, and the sealing layer is disposed on the display unit to cover the display unit. Thus, when the manufacturing of the mother panel is completed, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, when a laser beam is emitted toward the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate.

[0509] In some embodiments, the mother panel is cut into cell panels. In some embodiments, the mother panel is cut by using a cutting machine along the boundaries between the cell panels. In some embodiments, the grooves at the boundaries along which the mother panel is cut are covered with an organic coating, so that the organic coating absorbs shocks during cutting. In some embodiments, the barrier layer can be prevented from cracking during cutting.

[0510] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0511] Another aspect is an OLED display that includes a barrier layer formed on a base substrate, a display unit formed on the barrier layer, a sealing layer formed on the display unit, and an organic coating applied to an edge of the barrier layer. EXAMPLES

[0512] One embodiment of the present disclosure provides for preparing a compound of formula (I), formula (II), formula (III) or formula (IV) according to the procedures of one or more of the following examples using appropriate materials. Those skilled in the art will understand that these compounds can be prepared using known variations of the conditions and steps of the following preparation procedures. Furthermore, by utilizing the procedures described in detail, those skilled in the art can prepare further compounds of the present disclosure.

[0513] General information about analytical methods The features of the present invention will be described more specifically with reference to the following examples. The materials, steps, procedures, etc. shown below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention is not to be construed as being limited to the specific examples shown below. The properties of the samples were evaluated by using NMR (Nuclear Magnetic Resonance 500MHz, Bruker), LC / MS (Liquid Chromatography Mass Spectroscopy, Waters), AC3 (Riken Keiki), High Performance UV / Vis / NIR Spectrophotometer (Lambda 950, PerkinElmer, Co., Ltd.), Fluorescence Spectrophotometer (FluoroMax-4, Horiba, Ltd.), Photonic Multichannel Analyzer (PMA-12 C10027-01, Hamamatsu Photonics), Absolute PL Quantum Yield Measurement System (C11347, Hamamatsu Photonics), Automatic Current-Voltage-Brightness Measurement System (ETS-170, System Engineers Co., Ltd.), Lifetime Measurement System (EAS-26C, System Engineers Co., Ltd.) and Streak Camera (Model C4334, Hamamatsu Photonics).

[0514] Example 1 The principle of the feature can be explained as follows for an organic electroluminescent device as an example.

[0515] In an organic electroluminescent device, carriers are injected from the anode and cathode into the light-emitting material to form an excited state for the light-emitting material, which causes light to be emitted. In the case of a carrier-injection type organic electroluminescent device, generally, 25% of the total excitons generated are excited to the excited singlet state, and the remaining 75% are excited to the excited triplet state. Therefore, the use of phosphorescence, which is light emission from the excited triplet state, leads to high energy utilization. However, since the excited triplet state has a long life, the interaction with the excited triplet state excitons causes saturation of the excited state and deactivation of energy, so that the quantum yield of phosphorescence is generally not high in many cases. Delayed fluorescent materials emit fluorescence by a mechanism in which the energy of the excitons transitions to the excited triplet state by intersystem crossing or the like, and then transitions to the excited singlet state through triplet-triplet annihilation or reverse intersystem crossing due to thermal energy absorption, thereby emitting fluorescence. Among them, thermally activated delayed fluorescent materials that emit light by absorbing thermal energy are considered to be particularly useful for organic electroluminescence devices. When delayed fluorescent materials are used in organic electroluminescence devices, the excited singlet state excitons usually emit fluorescence. On the other hand, the excited triplet state excitons emit fluorescence by intersystem crossing to the excited singlet state by absorbing heat generated by the device. At this time, the light emitted by reverse intersystem crossing from the excited triplet state to the excited singlet state has the same wavelength as fluorescence, but has a longer lifetime (emission lifetime) than normal fluorescence and phosphorescence, since it is light emitted from the excited singlet state, and therefore, the light is observed as fluorescence delayed from normal fluorescence and phosphorescence. The light can be defined as delayed fluorescence. By using a thermally activated exciton transition mechanism, the ratio of the excited singlet state compound, which is generally formed at only 25% rate, can be increased to 25% or more through absorption of thermal energy after carrier injection. A compound that emits strong fluorescence and delayed fluorescence at low temperatures below 100°C can undergo intersystem crossing from the excited triplet state to the excited singlet state sufficiently due to the heat of the device, thereby emitting delayed fluorescence, and therefore the use of such a compound can dramatically increase the luminous efficiency.

[0516] Example 2 The compounds of the present invention can be synthesized by any method known to those skilled in the art. The compounds are synthesized from commonly available starting materials. The various moieties can be assembled via linear or branched synthetic routes.

[0517] Synthesis of compound 1

[0518] [ka]

[0519] Synthesis of 2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (A) 4-Bromo-2,6-difluorobenzonitrile (499 mg, 2.29 mmol), bis(pinacolato)diboron (700 mg, 2.75 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (84.9 mg, 0.115 mmol), anhydrous potassium acetate (675 mg, 6.88 mmol) and 1,4-dioxane (10 mL) were charged into a three-neck flask and the resulting solution was stirred at 110° C. for 2 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered through a Celite pad, rinsed with chloroform and the filtrate was evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel using hexane / ethyl acetate as eluent to give a beige solid (0.618 g, quantitative yield). 1 H NMR (500 MHz, CDCl 3 ,δ):7.43(d,J=8.0Hz,2H),1.35(s,12H);APCI-MS m / z:266.2 M +

[0520] Synthesis of 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-2,6-difluorobenzonitrile (B) Compound A (618 mg, 1.83 mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine (689 mg, 2.20 mmol), Pd(PPh) in a solution of degassed deionized water (3 mL) and degassed THF (9 mL). 3 ) 4 A mixture of (110 mg, 0.0918 mmol), potassium carbonate (774 mg, 5.51 mmol) and 1,2-dichlorophenyl ether (110 mg, 0.0918 mmol) was stirred at 80° C. under nitrogen atmosphere for 17 h. After cooling to room temperature, the reaction mixture was filtered through a pad of Celite, rinsed with chloroform, and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel using 3:2 (v / v) hexane / toluene as eluent to give a white solid (0.484 g, 57.0%). 1 H NMR (500 MHz, CDCl 3 ,δ):8.75(d,J=8.0Hz,4H),8.45(d,J=8.5Hz,2H),7.67(t,J=7.5Hz,2H),7.61(t,J=7.5Hz,4H);APCI-MS m / z:373.1 M +

[0521] Synthesis of 2,6-di(9H-carbazol-9-yl)-4-(4,6-diphenyl-1,3,5-triazin-2-yl)benzonitrile (1) A mixture of compound C (251 mg, 0.675 mmol), carbazole (284 g, 1.69 mmol) and potassium carbonate (283 g, 2.03 mmol) in 10 ml of N,N-dimethylformamide (DMF) was stirred at 140° C. under ambient atmosphere for 2 h. The reaction mixture was poured into a large amount of MeOH to give a yellow precipitate. After filtration, the solid obtained was washed with MeOH to give a yellow cake. The mixture was purified by silica gel column chromatography using 2:3 (v / v) petroleum ether / chloroform as eluent to give a greenish yellow solid (442 g, 98.5%). 1 H NMR (500 MHz, CDCl 3,δ):9.14(s,2H),8.68(d,J=7.0Hz,4H),8.23(d,J=8.0Hz,4H),7.60(t,J=7.5Hz,2H),7.56~7.51(m,8H),7.47~7.39(m,8H);APCI-MS m / z:665.3 M +

[0522] Synthesis of compound 2

[0523] [ka]

[0524] Synthesis of 2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-4',6'-difluoro-[1,1':3',1''-terphenyl]-5'-carbonitrile (C) A two-necked flask equipped with a stir bar was charged with compound B (0.50 g, 1.35 mmol), potassium carbonate (0.47 g, 3.38 mmol), palladium acetate (12.6 mg, 0.0405 mmol) and tricyclohexylphosphine (35.6 mg, 0.122 mmol) and was evacuated and backfilled with nitrogen three times. Bromobenzene (0.57 mL, 5.40 mmol), 2-ethylhexanoic acid (0.02 mL, 0.135 mmol) and xylene (10 mL) were added to the reaction mixture and stirred at room temperature for 15 minutes before heating to 150 °C. After stirring for 18 hours, the reaction mixture was cooled to room temperature and diluted with CHCl. 3 (10 mL) and water (10 mL), filtered through a pad of Celite, followed by CHCl 3 The aqueous layer was separated and washed with CHCl 3 (20 mL). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under vacuum and the crude product was purified by elution with 1:1 (v / v) hexane / CHCl as eluent. 3 The residue was purified by silica gel column chromatography using ethyl acetate to give a white solid (0.211 g, 30.0%). 1 H NMR (500 MHz, CDCl 3,δ):8.17(d,J=7.0Hz,4H),7.54(t,J=8.0Hz,2H),7.43(t,J=8.0Hz,4H),7.25~7.21(m,8H),7.16(t,J=7.0Hz,2H)

[0525] Synthesis of 4',6'-di(9H-carbazol-9-yl)-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':3',1''-terphenyl]-5'-carbonitrile (2) A mixture of compound D (459 mg, 0.896 mmol), carbazole (374 mg, 2.24 mmol) and potassium carbonate (379 mg, 2.03 mmol) in 10 ml of N,N-dimethylformamide (DMF) was stirred at 140° C. under ambient atmosphere for 2 h. The reaction mixture was poured into a large amount of MeOH to give a precipitate. After filtration, the solid obtained was washed with MeOH to give a greenish grey cake. The mixture was purified by silica gel column chromatography using 1:3 (v / v) hexane / chloroform as eluent to give a pale yellow solid (0.660 g, 90.2%). 1 H NMR (500 MHz, CDCl 3 ,δ):8.15(d,J=8.0Hz,4H),7.98(d,J=8.0Hz,4H),7.51(t,J=7.5Hz,2H),7.43~7.37(m,8H), 7.35(d,J=8.5Hz,4H),7.23(t,J=8.0Hz,4H),7.00~6.98(m,4H),6.71~6.70(m,6H);MALDI-MS m / z:815.7 M +

[0526] Synthesis of compound 3

[0527] [ka]

[0528] Synthesis of 2,3,5,6-tetra(9H-carbazol-9-yl)-4-(4,6-diphenylpyrimidin-2-yl)benzonitrile (3) K in NMP (40 mL) 2 CO 3 A mixture of 9H-carbazole (0.861 g, 5.15 mmol) and 1.07 g (1.07 g, 7.77 mmol) was stirred at room temperature for 1 h, and then compound 1 (0.42 g, 1.03 mmol) was added. The mixture was stirred at 100° C. for 48 h. The reaction mixture was stirred at H 2 The precipitated product was filtered, washed with MeOH, and extracted with CH 2 Cl 2 Recrystallization from 100% methanol / MeOH afforded compound 2 (0.786 g, 0.79 mmol) as a yellow powder in 76% yield. 1 H-NMR (500MHz, CDCl 3 ,δ):7.79(d,J=7.5Hz,4H),7.46(d,J=7.5Hz,4H),7.38(d,J=7.5Hz,4H),7.25~7.09(m,14H ),6.99(t,J=7.5Hz,4H),6.95~6.87(m,9H),6.64(d,J=7.5Hz,4H).MS(ASAP):993.4(M+).C 71 H 43 N 7 Calculated value for: 993.4

[0529] Synthesis of compound 4

[0530] [ka]

[0531] Synthesis of 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-2,3,5,6-tetrafluorobenzonitrile (E) 2-Iodo-4,6-diphenyl-1,3,5-triazine (4.10 g, 11.42 mmol), 2,3,5,6-tetrafluorobenzonitrile (3.0 g, 17.12 mmol), K 3 PO 4A mixture of (4.85 g, 22.83 mmol), CuI (0.65 g, 3.42 mmol) and 1,10-phenanthroline (0.62 g, 3.44 mmol) was stirred at 100 °C for 72 h. The reaction mixture was stirred at 10 2 Quench with 20O, wash with brine, extract with EtOAc, and wash with MgSO 4 The mixture was dried using hexane and concentrated under reduced pressure. The resulting mixture was subjected to silica gel column chromatography (hexane:toluene=2:1) ​​to obtain compound F (1.40 g, 3.44 mmol) as a white powder in a yield of 30.1%. 1 H-NMR (500MHz, CDCl 3 ,δ):8.68~8.66(m,4H),7.67~7.56(m,6H).MS(ASAP):406.8(M+).C 22 H 10 F 4 N 4 Calculated value for: 406.1

[0532] Synthesis of 2,3,5,6-tetra(9H-carbazol-9-yl)-4-(4,6-diphenyl-1,3,5-triazin-2-yl)benzonitrile (4) K in NMP (35 mL) 2 CO 3 A mixture of 9H-carbazole (2.81 g, 20.3 mmol) and 9H-carbazole (2.26 g, 13.54 mmol) was stirred at room temperature for 1 hour, after which compound E (1.1 g, 2.71 mmol) was added. The mixture was stirred at 100° C. for 24 hours. The reaction mixture was stirred at H 2 The precipitated product was filtered, washed with MeOH, and purified by silica gel column chromatography (hexane:CHCl 3 =1:1) to give compound 4 (2.40 g, 2.41 mmol) as a yellow powder in 88.9% yield. 1 H-NMR (500MHz, CDCl 3,δ):7.79(d,J=7.5Hz,4H),7.44(d,J=7.5Hz,4H),7.39(d,J=7.5Hz,4H),7.29~ 7.10(m,18H),7.02~6.98(m,8H),6.91(t,J=7.5Hz,4H).MS(ASAP):994.4(M+).C 70 H 42 N 8 Calculated value for: 994.4

[0533] Synthesis of compound 5

[0534] [ka]

[0535] Synthesis of 3-(4,6-diphenyl-1,3,5-triazin-2-yl)-2,4,5,6-tetrafluorobenzonitrile (F) A two-necked flask equipped with a stir bar was charged with 2,3,4,6-tetrafluorobenzonitrile (1.52 g, 8.57 mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine (2.68 g, 8.57 mmol), potassium carbonate (1.79 g, 12.85 mmol), palladium acetate (58 mg, 0.26 mmol), and tricyclohexylphosphine (218 mg, 0.771 mmol) and was evacuated and backfilled with nitrogen three times. 2-Ethylhexanoic acid (0.14 mL, 0.857 mmol) and xylene (50 mL) were added to the reaction mixture and stirred at room temperature for 15 minutes before heating to 130° C. After stirring for 5 hours, the reaction mixture was cooled to room temperature and diluted with CHCl. 3 (10 mL) and water (10 mL), filtered through a pad of Celite, followed by CHCl 3 The aqueous layer was separated and washed with CHCl 3 (20 mL). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under vacuum and the crude product was purified by elution with 2:1 (v / v) hexane / CHCl as eluent. 3The residue was purified by silica gel column chromatography using ethyl acetate to give a pale yellow solid (0.45 g, 412.9%). 1 H NMR (500 MHz, CDCl 3 ,δ):8.67(d,J=7.5Hz,4H),7.65(t,J=7.5Hz,2H),7.58(t,J=8.0Hz,4H);ESI-MS m / z:407 M +

[0536] Synthesis of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(4,6-diphenyl-1,3,5-triazin-2-yl)benzonitrile (5) A mixture of carbazole (0.65 g, 3.88 mmol), compound F (0.35 g, 0.861 mmol) and potassium carbonate (0.60 g, 4.31 mmol) in 10 ml of N,N-dimethylformamide (DMF) was stirred at 140° C. under ambient atmosphere for 3 h. The reaction mixture was poured into MeOH to give a yellow precipitate. After filtration, the resulting solid was washed with MeOH to give a yellow cake. The mixture was purified by silica gel column chromatography using 2:1 (v / v) chloroform / hexane as eluent to give a yellow solid (0.81 g, 94.3%). 1 H NMR (500 MHz, CDCl 3 ,δ):7.88(d,J=7.5Hz,2H),7.73(d,J=7.0Hz,2H),7.50(d,J=8.0Hz,2H),7.45 ~7.41(m,4H),7.38(d,J=8.0Hz,2H),7.32(t,J=7.5Hz,2H),7.29(d,J=8.0Hz, 2H),7.25~7.24(m,2H),7.22(m,6H),7.09~7.03(m,10H),7.93(t,J=7.5Hz,2H ),6.88(t,J=7.5Hz,2H),6.82(t,J=7.5Hz,2H),6.68(t,J=8.5Hz,2H);ESI-MS m / z:995M +

[0537] Synthesis of compound 6

[0538] [ka]

[0539] Synthesis of 4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-2,3,5,6-tetrafluoro-[1,1'-biphenyl]-4-carbonitrile (G) 2-(4-Bromophenyl)-4,6-diphenyl-1,3,5-triazine (5.00 g, 12.88 mmol), bis(pinacolato)diboron (3.93 g, 15.46 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.485 g, 0.644 mmol), anhydrous potassium acetate (3.81 g, 38.64 mmol) and 1,4-dioxane (50 mL) were charged into a three-neck flask and the resulting solution was stirred at 110° C. for 14 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered through a Celite pad, rinsed with ethyl acetate and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel using 10:1 (v / v) hexane / ethyl acetate as eluent to give a beige solid (4.74 g, 84.5%). 1 H NMR (500 MHz, CDCl 3 ,δ):8.79(d,J=8.0Hz,4H),8.76(d,J=8.5Hz,2H),8.01(d,J=8.5Hz,2H),7.64~7.57(m,6H),1.40(s,12H)

[0540] Synthesis of 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (H) Compound G (6.50 g, 14.93 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (3.86 g, 15.23 mmol), Pd(PPh) in a solution of degassed deionized water (20 mL) and degassed THF (60 mL). 3 ) 4A mixture of 1,2-dichlorophenyl ether (871 mg, 0.747 mmol), potassium carbonate (6.21 g, 44.79 mmol) was stirred at 80° C. under nitrogen atmosphere for 24 h. After cooling to room temperature, the reaction mixture was added with methanol (400 mL) and filtered. The solid obtained was washed successively with water (20 mL) and methanol (20 mL) and finally dried in vacuum. The residue obtained was purified by column chromatography on silica gel using 3:1 (v / v) hexane / toluene as eluent to give a white solid (4.80 g, 66.6%). 1 H NMR (500 MHz, CDCl 3 ,δ):8.94(d,J=6.5Hz,2H),8.80(d,J=7.0Hz,4H),7.70(d,J=8.5Hz,2H),7.66~7.59(m,6H);APCI-MS m / z:483.4 M +

[0541] Synthesis of 2,3,5,6-tetra(9H-carbazol-9-yl)-4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (6) A mixture of 9H-carbazole (1.88 g, 11.20 mmol), compound I (12.06 g, 11.20 mmol) and potassium carbonate (4.67 g, 33.60 mmol) in 190 ml of N-methyl-2-pyrrolidone (NMP) was stirred at 150° C. under ambient atmosphere for 2 hours. The reaction mixture was poured into MeOH to obtain a precipitate. After filtration, the obtained solid was washed with MeOH to obtain the crude product. The mixture was purified by silica gel column chromatography using 3:1 (v / v) toluene / hexane as eluent to obtain a greenish yellow solid (8.93 g, 74.4%). 1 H NMR (500 MHz, CDCl 3,δ):8.48(d,J=7.0Hz,4H),7.92(d,J=7.0Hz,2H),7.74~7.71(m,4H),7.56(d,J=7.5Hz,4H),7.50(t,J= APCI-MS m / z:1071.8M +

[0542] Synthesis of compound 7

[0543] [ka]

[0544] Synthesis of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (I) 2-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.02 g, 7.73 mmol), bis(pinacolato)diboron (2.35 g, 9.27 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (286 mg, 0.386 mmol), anhydrous potassium acetate (2.29 g, 23.2 mmol) and 1,4-dioxane (40 mL) were charged into a three-neck flask and the resulting solution was stirred at 110° C. for 2 h under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered through a Celite pad, rinsed with chloroform and the filtrate was evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel using 1:1 (v / v) hexane / toluene as eluent to give a white solid (2.73 g, 81.1%). 1 H NMR (500 MHz, CDCl 3,δ):9.14(s,1H),8.88(d,J=7.5Hz,1H),8.81(d,J=6.0Hz,4H),8.06(d,J=7.5Hz,1H),7.64~7.54(m,7H),1.42(s,12H);APCI-MS m / z:436.3 M +

[0545] Synthesis of 3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-2,3,5,6-tetrafluoro-[1,1'-biphenyl]-4-carbonitrile (J) Compound I (2.00 g, 4.59 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1.19 g, 4.69 mmol), Pd(PPh) in a solution of degassed deionized water (6 mL) and degassed THF (18 mL). 3 ) 4 A mixture of (268 mg, 0.230 mmol), potassium carbonate (1.90 mg, 13.78 mmol) was stirred at 80° C. under nitrogen atmosphere for 18 h. After cooling to room temperature, the reaction mixture was filtered through a pad of Celite, rinsed with chloroform, and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel using 3:2 (v / v) hexane / toluene as eluent to give a white solid (0.962 g, 43.4%). 1 H NMR (500 MHz, CDCl 3 ,δ):8.94(d,J=8.0Hz,1H),8.86(s,1H),8.77(d,J=8.0Hz,4H),7.77(t,J=7.5Hz,1H),7.70(d,J=7.5Hz,1H),7.66~7.57(m,6H)

[0546] Synthesis of 2,3,5,6-tetra(9H-carbazol-9-yl)-3'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carbonitrile (7) To a stirred solution of 9H-carbazole (1.51 g, 8.97 mmol) in anhydrous tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 404 mg, 9.97 mmol) at room temperature under nitrogen atmosphere. After stirring for 1 h, compound J (951 mg, 1.99 mmol) was added and the mixture was heated at 80° C. for 6 h. After cooling to room temperature, the reaction solution was poured into MeOH to obtain a precipitate. The resulting mixture was filtered and the resulting solid was washed with MeOH. The residue was purified by column chromatography using 1:2 (v / v) hexane / toluene as eluent to obtain a light yellow solid (1.52 g, 45.1%). 1 H NMR (500 MHz, CDCl 3 ,δ):8.30(d,J=8.5Hz,4H),8.22(s,1H),8.04(d,J=8.5Hz,1H),7.75~7.72(m,4H),7.56~7.51(m,4H),7.48~7.44(m,6H),7.32~7.30(m,2H) ),7.25~7.23(m,2H),7.19(d,J=8.0Hz,2H),7.13~7.05(m,10H),6.99~6.91(m,7H),6.80(t,J=7.5Hz,2H),6.64(t,J=8.0Hz,1H);APCI-MS m / z:1071.8M +

[0547] Synthesis of compound 8

[0548] [ka]

[0549] Synthesis of 4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4,5,6-tetrafluoro-[1,1'-biphenyl]-2-carbonitrile (K) Bis(triphenylphosphine)palladium(II) dichloride (0.57 mmol, 0.40 g), 2,3,4,5-tetrafluorobenzonitrile (11.42 mmol, 2.00 g), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (17.13 mmol, 6.65 g), potassium carbonate (34.27 mmol, 4.74 g), 2-ethylhexanoic acid (2.28 mmol, 0.33 g) and tricyclohexylphosphine (1.71 mmol, 0.48 g) were placed in a three-necked round-bottom flask under nitrogen atmosphere. After flushing with nitrogen gas for 1 min, it was dissolved in xylene. The temperature of the mixture was raised to 100 °C and then stirred overnight. The reaction was quenched with brine solution at room temperature and the mixture was extracted with chloroform and MgSO 4 After drying through a vacuum evaporator system, the mixture was purified by column chromatography on silica gel using n-hexane / chloroform as eluent. A white powdery product was obtained (0.96 g, 17.34% yield). 1 H NMR (500 MHz, CDCl 3 )δ 7.58~7.65(m,6H),7.68(d,J=8.5Hz,2H),8.79(d,J=7Hz,4H),8.94(d,J=8.5Hz,2H). 19 F NMR (470MHz, CDCl 3 )δ -152.45(td,J F =23.5,4.7Hz,1F),-143.95(td,J F =18.8,9.4Hz,1F),-137.47(qd,J F =21.2,9.4,4.7Hz,1F),-129.61~-129.69(m,1F) MS(APCI) m / z 483.10[(M+H) + ]

[0550] Synthesis of (3s,4r,5r,6r)-3,4,5,6-tetra(9H-carbazol-9-yl)-4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-carbonitrile (8) Potassium carbonate (11.81 mmol, 1.63 g), 4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-3,4,5,6-tetrafluoro-[1,1'-biphenyl]-2-carbonitrile (K, 1.97 mmol, 0.95 g) and 9H-carbazole (9.85 mmol, 1.65 g) were placed in a three-neck round-bottom flask. After the mixture was dried by a vacuum system, N-methyl-2-pyrrolidone was poured into the flask as a solvent under nitrogen atmosphere. The reaction mixture was stirred overnight while maintaining the temperature at 130°C. The reaction was quenched with brine and the mixture was extracted with chloroform. The separated organic layer was washed with MgSO 4 The mixture was dried by filtration and the solvent was concentrated by a vacuum evaporator system. The reaction product was isolated by column chromatography using a mixture of chloroform and hexane (1:4) as the eluent. The final product was obtained (1.99 g, 94.29%). 1 H NMR (500 MHz, CDCl 3 )δ 6.59(q,J=8Hz,4H),6.72~6.75(m,4H),6.93~6.97(m,4H),7.03~7.09(m,8H),7.18~7.20(m,3H),7.26~7.3 0(m,5H),7.51~7.58(m,10H),7.73(d,J=7Hz,2H),8.55(d,J=8.5Hz,2H),8.67(d,J=7Hz,4H),MS(APCI)m / z 1071.49[(M+H) + ]

[0551] Example 3 Preparation of neat membranes In this example, compound 2 synthesized in Example 2 was used in a concentration of 10 -3 The solution was evaporated on a quartz substrate by vacuum evaporation under a vacuum of 100 Pa or less to form a thin film having a thickness of 70 nm.

[0552] Preparation of doped films Compound 2 and the host were also evaporated from separate sources at a vacuum of 10°C. -3 Compound 2 was evaporated on a quartz substrate by vacuum evaporation under a vacuum of 0.1 Pa or less to form a thin film having a thickness of 100 nm and a concentration of 20 wt %.

[0553] Optical property evaluation The sample was irradiated with light having a wavelength of 300 nm at 300 K and the emission spectrum was measured, which was designated as fluorescence. The spectrum was also measured at 77 K, which was designated as phosphorescence. The lowest singlet energy (S 1 ) and the lowest triplet energy (T 1 ) were estimated from the onset of the fluorescence and phosphorescence spectra, respectively. ST is S 1 and T 1 The PLQY was also measured with an excitation light of 300 nm. Time-resolved spectra were obtained with a streak camera with an excitation light of 337 nm, and the components with short emission lifetimes were designated as fluorescence and those with long emission lifetimes as delayed fluorescence. The lifetimes of the fluorescent components (τ prompt ) and the lifetime of the delayed fluorescence component (τ delay ) was calculated from the decay curves.

[0554] OLED fabrication and measurement A 1.0×10 GaN layer was placed on a glass substrate on which an anode made of indium tin oxide (ITO) having a thickness of 100 nm was formed. -4 The thin film was laminated by vacuum deposition at a vacuum of 0.1 Pa or less. First, HAT-CN was formed on ITO to a thickness of 10 nm, and TrisPCz was formed thereon to a thickness of 25 nm. After PYD2 was formed to a thickness of 5 nm, compound 2 and a host were simultaneously deposited thereon from separate deposition sources to form a layer having a thickness of 30 nm, which was designated as the light-emitting layer. At this time, the concentration of compound 2 was 20 wt%. Next, SF3-TRZ was formed to a thickness of 10 nm, and SF3-TRZ and Liq were simultaneously deposited thereon to a thickness of 30 nm. Next, Liq was vacuum-deposited to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, whereby an organic electroluminescent device was fabricated, and its photoelectric properties were measured.

[0555] As comparative examples, the same evaluation results were measured using compounds 3 and 5 to 8 synthesized in Example 2 instead of compound 2, and the same evaluation results were also measured using compound 1.

[0556] [Table 6]

[0557] [Table 7]

[0558] [Table 8]

[0559] * 1:ITO / HAT-CN(10) / TrisPCz(25) / PYD2(5) / EML(30) / SF3-TRZ(10) / SF3-TRZ:Liq=7:3(40) / Liq(2) / Al * 2:ITO / HAT-CN(10) / TrisPCz(25) / PYD2(5) / EML(30) / SF3-TRZ(10) / SF3-TRZ:Liq=7:3(35) / Liq(2) / Al * 3:ITO / HAT-CN(10) / a-NPD(30) / TrisPCz(10) / PYD2(5) / EML(30) / SF3-TRZ(10) / SF3-TRZ:Liq=7:3(30) / Liq(2) / Al * 4:ITO / HAT-CN(60) / TrisPCz(30) / PYD2(5) / EML(30) / SF3-TRZ(10) / SF3-TRZ:Liq=7:3(30) / Liq(2) / Al * 4': ITO / HAT-CN(60) / TrisPCz(30) / PYD2(5) / Host:Compound.x:TBPe=69.5:30:0.5(30) / SF3-TRZ(10) / SF3-TRZ:Liq=7:3(30) / Liq(2) / Al

[0560]

change

Claims

1. Formula (I): 【Chemistry 1】 (In the formula, R １ , R ２ , R ３ , R ４ and R ５ are independently hydrogen, deuterium, A 1 and D １ is selected from R １ , R ２ , R ３ , R ４ and R ５ Of R ２ But, A １ and R １ , R3, R ４ and R ５ At least three of the following are D １ and A １ are independently a group represented by the following formula: 【Chemistry 2】 is selected from X Ａ are independently O, S and NR Ａ’ is selected from R Ａ is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; R Ａ’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; L Ａ is a single bond, D １ are independently a group represented by the following formula: 【Chemistry 3】 is selected from X Ｄ are independently O, S, NR Ｄ’ , C(O), substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted vinylene, substituted or unsubstituted o-arylene, and substituted or unsubstituted o-heteroarylene, wherein methylene, ethylene, vinylene, o-arylene or o-heteroarylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; R Ｄ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; Two adjacent R's Ｄ may be bonded to each other to form a ring, R Ｄ’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; L Ｄ are independently selected from a single bond, and substituted or unsubstituted arylene, where arylene is optionally substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; Each "*" represents a point of attachment to formula (I).

2. Each alkyl is C １ ~C ２０ alkyl, and each aryl is C ６ ~C ４０ aryl, each heteroaryl being C ２ ~C ４０ heteroaryl, and each alkoxy is C １ ~C ２０ alkoxy, each aryloxy being C ６ ~C ４０ aryloxy, each heteroaryloxy being C ３ ~C ４０ The compound of claim 1 which is heteroaryloxy.

3. A １ is a group represented by the following formula: 【Chemistry 4】 3. The compound according to claim 1 or 2, selected from:

4. A １ is a group represented by the following formula: 【Chemistry 5】 3. The compound according to claim 1 or 2, selected from:

5. D １ is a group represented by the following formula: 【Chemistry 6】 The compound according to any one of claims 1 to 4,

6. D １ is a group represented by the following formula: 【Chemistry 7】 The compound according to any one of claims 1 to 4,

7. D １ is a group represented by the following formula: 【Chemistry 8】 The compound according to any one of claims 1 to 4,

8. L Ｄ The compound according to any one of claims 1 to 7, wherein is a single bond.

9. R １ , R ２ , R ３ , R ４ and R ５ The compound according to any one of claims 1 to 8, wherein none of is hydrogen or deuterium.

10. The compound of claim 1 , wherein the compound of formula (I) is represented by the following formula: 【Chemistry 9】

11. A delayed fluorescent emitter comprising a compound of formula (I) according to any one of claims 1 to 10.

12. An organic light-emitting diode comprising a compound of formula (I) according to any one of claims 1 to 10. (OLED).

13. 1. An organic light emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A host material; A compound of formula (I) 13. The organic light emitting diode (OLED) of claim 12 comprising:

14. 1. An organic light emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A host material; A compound of formula (I) 13. The organic light emitting diode (OLED) of claim 12, comprising:

15. 1. An organic light emitting diode (OLED) comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode, the emissive layer comprising: A host material; A compound of formula (I) A light-emitting material not represented by formula (I); 13. The organic light emitting diode (OLED) of claim 12 comprising:

16. The organic light emitting diode (OLED) according to any one of claims 12 to 15, which emits delayed fluorescence.

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