WO2021127381A1 - Composition of matter for use in organic light-emitting diodes - Google Patents

Composition of matter for use in organic light-emitting diodes Download PDF

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Publication number
WO2021127381A1
WO2021127381A1 PCT/US2020/065923 US2020065923W WO2021127381A1 WO 2021127381 A1 WO2021127381 A1 WO 2021127381A1 US 2020065923 W US2020065923 W US 2020065923W WO 2021127381 A1 WO2021127381 A1 WO 2021127381A1
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substituted
unsubstituted
formula
alkyl
deuterium
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PCT/US2020/065923
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French (fr)
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Yong Joo Cho
Yoshitake Suzuki
Hiroaki Ozawa
Yuseok Yang
Minki HONG
Masataka Yamashita
Kaori FUJISAWA
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Kyulux, Inc.
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Publication of WO2021127381A1 publication Critical patent/WO2021127381A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • OLED organic light-emitting diode
  • LED light-emitting diode
  • a problem inherent in OLED displays is the limited lifetime of the organic compounds.
  • OLED materials rely on the radiati ve decay of molecular excited states (excitons) generated by recombination of electrons and holes in a host transport material.
  • OLED material design has focused on harvesting the remaining energy from the normally dark triplets.
  • Recent work to create efficient phosphors, which emit light from the normally dark triplet state have resulted in green and red OLEDs.
  • Other colors, such as blue, however, require higher energy excited states which accelerate the degradation process of the OLED.
  • the fundamental limiting factor to the triplet-singlet transition rate is a value of the parameter jif fi /AEsi ⁇ , where H is the coupling energy due to hyperfine or spin-orbit interactions, and AEST IS the energetic splitting between singlet and triplet states.
  • Traditional phosphorescent OLEDs rely on the mixing of singlet and triplet states due to spin-orbital (SO) interaction, increasing i3 ⁇ 4, and affording a lowest emissive state shared between a heavy metal atom and an organic ligand. Tins results in energy harvesting i from all higher singlet and triplet states, followed by phosphorescence (relatively short lived emission from the excited triplet). The shortened triplet lifetime reduces triplet exciton annihilation by charges and other excitons. Recent work by others suggests that the limit to the performance of phosphorescent materials has been reached.
  • the present disclosure relates to novel materials for OLEDs.
  • these OLEDs can reach higher excitation states without rapid degradation it has now been discovered that thermally activated delayed fluorescence (TADF), which relies on minimization of AEST as opposed to maximization of Hr, can transfer population between singlet levels and triplet sublevels in a relevant timescale, such as, for example, Ips-lOms.
  • TADF thermally activated delayed fluorescence
  • the compounds described herein are capable of luminescing at higher energy excitation states than compounds previously described.
  • the present disclosure provides: [1] An organic light-emitting diode (OLED) comprising a compound of
  • Y 1 is X or R’-C
  • Y 2 is X or R 2 -C
  • Y 3 is X or R 3 -C
  • Y 4 is N or R 4 -C
  • Y 5 is N or R 5 -C
  • Y 6 is
  • Y 7 is X or R -C.
  • Y 8 is N or R 8 -C, provided that at most two of Y ! , Y 2 , Y J , Y 4 , Y 5 , Y 6 , Y' and Y 8 are N, one or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R and R 8 are independently D, other one or more of Ry R 2 , R 3 , R 4 , R 5 , R°, R 7 and R 8 are independently A, the other remaining R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R ; and R 8 are independently selected from H, deuterium, substituted or unsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and pheny l can be substituted with one or more substituents independently selected from deuter
  • A is selected from CN-L A -*, PFA-I/ -* or Het- L A ⁇ * PFA is perfluoroalkyl,
  • Het is substituted or unsubstituted heteroaryl having at least one nitrogen atom as a ring-constituting atom
  • D is group of Formula (lia), (lib), (Ik) or (lid):
  • X' is selected fromN-R 0 ’, O and S;
  • R° is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ammo, substituted or un substituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and siiyi; two or more instances of R D taken together can form a ring system;
  • R d ’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted and, and substituted or unsubstituted heteroaryl; two or more instances of R rb and R D taken together can form a ring system;
  • L D and L A are independently selected from single bond, substituted or unsubstituted aryiene, and substituted or unsubstituted heteroaiylene; wherein each instance of aryiene and heteroaryl ene can 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 these substituents taken together can form a ring system; C-R D of the benzene rings in Formulae (Ila), (lib), (lie) and (lid) may be substituted with N; and each represents a point of attachment to Formula (1).
  • OLED organic light-emitting diode
  • A is CN-L a -*, PFA-L a -* or Het-L A -* in which L A of Het-L A -* is substituted or unsubstituted aryiene, and substituted or unsubstituted heteroaryiene; wherein each instance of aryiene and heteroaiylene can be substituted with one or more substituents independently selected from deuterium substituted or unsubstituted alkyl, substituted or unsubstituted aryi, and substituted or unsubstituted heteroaryi, and wherein two or more of these substituents taken together can form a ring system.
  • OLED organic light-emitting diode
  • D is a group of Formula (lib) and at least one of R° is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, or sifyl.
  • R° is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, or sifyl.
  • R° is substituted or unsubstituted alkyl, substituted or unsubsti
  • D is a group of Formula (lib) and I
  • D is substituted or unsubstituted arylene, and substituted or unsubstituted heteroaiylene
  • each instance of arylene and heteroaiylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, and wherein two or more of these substituents taken together can form a ring system.
  • OLED organic light-emitting diode
  • D is group of Formula (Ha). (lie) or (lid)
  • OLED organic light-emitting diode
  • the organic light-emitting diode has a light-emitting layer comprising a host material, the compound of Formula (1) and a light-emitting material; and the compound of Formula (I) has a lowest excited singlet energy' level between the lowest excited singlet energy level of the host material and the lowest excited singlet energy level of the light-emitting material.
  • OLED organic light-emitting diode
  • the Formula (1) does not include a compound wherein Y 1 is Rd-C, Y 2 is R 2 - C, Y 3 is R -C.
  • Y 4 is R 4 -C, Y 5 is R s -C, Y 6 is R' -C.
  • Y 7 is R -C.
  • Y 8 is R S ⁇ C, only one of R ’ , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 is A, A is selected from
  • R 21 , R 22 , R 23 , R 24 and R 25 are independently substituted or unsubstiiuted aryl, or substituted or unsubstituted heteroaryl, L 11 is single bond, D is group of Formula (lib), L D is single bond, and C-R° of the benzene rings in Formula (lib) is not substituted with N.
  • R 21 , R 22 , R 2 , R 24 and R 25 are independently substituted or unsubstiiuted aryl, or substituted or unsubstituted heteroaryl, L“ is single bond, D is group of Formula (lib), L D is single bond, R° is hydrogen, and C-R D of the benzene rings in Formula (lib) is not substituted with N.
  • OLED organic light-emitting diode
  • OLED organic light-emitting diode
  • OLED organic light-emitting diode
  • OLED organic light-emitting diode
  • Y 6 is R 6 -C
  • Y' is R'-C
  • R b and R 7 are independently D
  • none ofY 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y '6 , Y 7 and 8 are N
  • two of R 1 , R 2 , R' and R 4 are independently D and these two differ from each other.
  • OLED organic light-emitting diode
  • Y 7 is R 7 -C, and R / is A;
  • Y 8 is R 8 -C, and R s is A.
  • OLED organic light-emitting diode
  • D is independently selected from D56 and D58; and the hydrogen atoms in D56 and D58 may be substituted by deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ammo, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaiy doxy, or silyl.
  • OLED organic light-emitting diode
  • OLED organic light-emitting diode
  • the compounds have a structure of Formula (I): C, Y t is N or R 6 -C, Y 1 is N or R 7 -C, and Y 8 is N or R 8 -C, provided that at most two of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 and Y 8 are N, one or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R' and R 8 are independently D, other one or more of R 1 , R 2 , R J , R 4 , R 5 , R 6 , R' ’ and R 8 are independently A, the other remaining R 1 , R 2 , R 3 , R 4 , R 5 , R b , R' and R 8 are independently selected from H, deuterium, substituted or unsubstituted alkyl, and substituted or unsubstituted phenyl other than D and A
  • PFA is perfluoroaikyl
  • Het is substituted or unsubstituted heteroaiy] having at least one nitrogen atom as a ring-constituting atom,
  • D is group of Formula (Ila), (lib), (lie) or (lid):
  • X ! is selected from N-R°’, G and S;
  • R D is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ammo, substituted or unsubstituted and, substituted or unsubstituted aryioxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; two or more instances of R D taken together can form a ring system;
  • R 0 ’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted ammo, substituted or unsubstituted and, and substituted or unsubstituted heteroaryl; two or more instances of and R D taken together can form a ring system;
  • L D and L A are independently selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroaiylene; wherein each instance of arylene and heteroaiylene can he substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaiyl; two or more of these substituents taken together can form a ring system;
  • C ⁇ R D of the benzene rings in Formulae (Ila), (lib), (Tic) and (lid) may be substituted with N; and each represents a point of attachment to Formula (I).
  • alkyl is CI-C20-alkyl. In some embodiments, alkyl is Cl- C12 alkyl. In some embodiments, alkyl is C1-C6 alkyl in some embodiments, alkyl is C1-C3 alkyl. In some embodiments, aryl is C6-C40 aryl. In some embodiments, aryl is C6-C25 and. In some embodiments, an is C6-C14 aryl in some embodiments, aryl is C6-C10 aryl. In some embodiments, heteroaryl is C2-C40 heteroaryl. In some embodiments, heteroaryl has 5-40 ring-constituting atoms.
  • heteroaryl has 5-25 ring-constituting atoms. In some embodiments, heteroaryl has 5-10 ring-constituting atoms.
  • alkoxy is C1-C20 aikoxy. In some embodiments, alkoxy is Cl-Cl 2 alkoxy. In some embodiments, alkoxy is C1-C6 alkoxy. In some embodiments, alkoxy is C1-C3 alkoxy.
  • aryloxy is C6 ⁇ C40 aryloxy. In some embodiments, aryloxy is C6-C25 aryloxy. In some embodiments, aiyioxy is C6-C14 aryloxy.
  • aryloxy is C6-C10 aryloxy.
  • heteroaryloxy is C3-C40 heteroaryl oxy.
  • heteroaiyloxy has 5-40 ring-constituting atoms.
  • heteroaryloxy has 5-25 ring-constituting atoms.
  • heteroaryloxy has 5-10 ring- constituting atoms.
  • arylene is C6-C40 arylene.
  • arylene is C6-C25 arylene.
  • arylene is C6-C14 arylene.
  • arylene is C6-C10 arylene.
  • heteroarylene is C2-C40 heteroarylene. In some embodiments, heteroarylene has 5-40 ring-constituting atoms. In some embodiments, heteroarylene has 5-25 ring-constituting atoms in some embodiments, heteroarylene has 5-10 ring-constituting atoms.
  • X in Formula (I) is O. In some embodiments, X in Formula (I) is S.
  • Y 1 is N or R ! -C.
  • Y 2 iS N or R 2 ⁇ C Y 3 is N or R 3 -C
  • Y 4 is N or R 4 -C
  • Y 5 is N or R 5 - C
  • Y tJ is N or R 6 -C
  • Y' is N or R 7 -C
  • Y 8 is N or R 8 -C, provided that at most two of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 and Y 8 are N,
  • Y 1 is R'-C.
  • Y 2 is R 2 -C.
  • Y 3 is R5-C.
  • Y 4 is R 4 -C.
  • Y 5 is R 3 -C.
  • Y tJ is R 6 -C.
  • Y 7 is R'-C.
  • Y 8 is R 8 ⁇ C.
  • is N. in some embodiments, Y 2 is N.
  • Y 3 is N.
  • Y 4 is N.
  • Y’ is N.
  • Y 6 is N.
  • Y 7 is N. In some embodiments, Y 8 is N. In some embodiments, Y 1 is R'-C, Y 2 is R 2 -C, Y' is R'-C, and Y 4 is R 4 -C. In some embodiments, Y 1 is N, Y 2 is R -C, Y 3 is R 3 ⁇ C, and Y 4 is R 4 -C. in some embodiments, Y 5 is R 5 -C. In some embodiments, Y 6 is R°-C. In some embodiments, Y ? is R 7 -C. In some embodiments, Y 8 is R 8 -C.
  • Y 1 is N, Y 2 is R -C, Y 3 is R 3 -C, and Y 4 is R 4 -C.
  • Y 1 is R l -C, Y 2 is N, Y is R -C, and Y 4 is R 4 -C.
  • Y 1 is R 3 -C, Y 2 is R 2 -C, Y 3 is N, and Y 4 is R 4 -C.
  • Y 1 is R ! -C, Y 2 is R 2 - C, Y 3 is R 3 -C, and Y 4 is N.
  • Y 1 is N
  • Y 2 is N
  • Y 3 is R 3 ⁇ C
  • Y 4 is R 4 -C.
  • Y ! is N
  • Y 2 is R -C
  • Y' is N
  • Y' 4 is R 4 -C.
  • Y 1 is N
  • Y 2 is R 2 -C
  • Y' is R 3 -C
  • Y 4 is N.
  • Y 1 is N, Y 2 is N, Y 3 is R 3 ⁇ C, and Y 4 is N.
  • R 3 -C, Y 2 is N, Y 3 is N, and Y 4 is R 4 ⁇ C.
  • Y 1 is R 1 -C
  • Y 2 is N
  • Y 3 is R 3 ⁇ C
  • Y 4 is N
  • Y 1 is Rt-C
  • Y 2 is R 2 ⁇ C
  • Y 3 is N
  • Y 4 is N
  • Y 3 is N
  • Y 6 is R 6 -C
  • Y 7 is R'-C
  • Y 8 is R*-C.
  • Y 5 is R s -C
  • Y b is N
  • Y 7 is R 7 -C
  • Y s is R s -C.
  • Y 3 is R s -C
  • Y 6 is R 6 -C
  • Y 1 is N
  • Y 8 is R s -C
  • Y 3 is R 3 -C
  • Y 6 is R 6 -
  • Y 7 is R 7 -C
  • Y 8 is N.
  • Y 3 is N
  • Y 6 is N
  • Y' is R'-C
  • Y 8 is R 8 -C.
  • Y 3 is N
  • Y b is R 6 -C
  • Y 7 is N
  • Y 8 is R s -C.
  • Y 5 is N
  • Y 6 is R 6 -C
  • Y' is R 7 -C
  • Y 8 is N.
  • Y 5 is R 5 ⁇ C
  • Y 6 is N
  • Y 7 is N
  • Y 8 is R 8 ⁇ C.
  • Y 5 is R 5 -C
  • Y 6 is N
  • Y 7 is R 7 -C
  • Y 8 is N
  • Y' 5 is R 3 -C
  • Y 6 is R 6 -C
  • Y' is N
  • Y 8 is N.
  • none of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 and Y 8 are N.
  • one of Y 1 , Y , Y 3 , Y 4 , Y 5 , Y 6 , Y' ' and Y 8 is N.
  • one of Y 5 , Y' 2 , Y 3 and Y 4 is N, and none of Y 3 , Y 6 , Y 7 and Y 8 are N.
  • none of Y 1 , Y 2 , Y and Y 4 are N, and one of Y 5 , Y b , Y 7 and Y 8 is N.
  • two of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 and Y 8 are N.
  • one of Y 1 , Y 2 , Y 3 and Y 4 is N, and one of Y 3 , Y 6 , Y ; and Y 8 is N.
  • two of Y 1 , Y 2 , Y 3 and Y 4 are N, and none of Y 5 , Y 6 , Y 7 and Y 8 are N. In some embodiments, none of Y 1 , Y 2 , Y 3 and Y 4 are N, and two of Y 5 , Y 6 , Y' and Y 8 are N.
  • R ’ is D. In some embodiments, R 2 is D. In some embodiments, R 3 is D. In some embodiments, R 4 is D. In some embodiments, R 5 is D. In some embodiments, R 13 is
  • R' is D.
  • R 8 is D. in some embodiments, only one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R' and R 8 is D. In some embodiments, at least two of R 1 , R 2 , R 3 , R 4 , R 3 , R', R 7 and R 8 are D. In some embodiments, at least three of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are D. In some embodiments, at least four of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 ,
  • R' and R 8 are D. In some embodiments, at most six of R 1 , R 2 , R 3 , R 4 , R 5 , R b , R' and R 8 are D In some embodiments, at least one of R 1 , R z , R 3 and R 4 is D. In some embodiments, only one of R 1 , R 2 , R 3 and R 4 is D. In some embodiments, two of R 1 , R 2 , R 3 and R 4 are D. In some embodiments, three of R 1 , R 2 , R 3 and R 4 are D. In some
  • R 5 , R 2 , R and R 4 are D. In some embodiments, two or three of R f , R 2 , R 3 and R 4 are D. in some embodiments, at least one of R 5 , R 6 , R 7 and R* is D. In some embodiments, only one of R 5 , R 6 , R 7 and R 8 is D. in some embodiments, two of R 5 , R 6 , R 7 and R 8 are D. In some embodiments, three of R ' , R 6 , R 7 and R 8 are D. In some embodiments, all of R 5 , R b , R' and R 8 are D. In some embodiments, two or three of R 3 ,
  • R 6 , R 7 and R 8 are D.
  • at least one of R 1 , R 2 , R ' and R 4 is D, and at least one of R 5 , R°, R' and R 8 is D.
  • at least two of R 1 , R 2 , R 3 and R 4 are D, and at least one of R 5 , R 6 , R 7 and R 8 is D.
  • at least one of R 1 , R 2 , R 3 and R 4 is B, and at least two of R 5 , R 6 , R' and R 8 are D.
  • R 1 , R 2 , R J and R 4 are D, and at least two of Rf R 6 , R' ' and R 8 are D.
  • at least three of R 1 , R 2 , R 3 and R 4 are D, and at least two of R: 1 , R°, R 7 and R 8 are D.
  • R 1 and R 2 are D.
  • R ! and R 3 are D.
  • R 1 and R 4 are D.
  • R 2 and R 3 are D.
  • R 2 and R 4 are D.
  • R 3 and R 4 are D In some embodiments, R 1 , R 2 and R 3 are D.
  • R 4 , R 2 and R 4 are D. In some embodiments, R 1 , R 3 and R 4 are D. In some embodiments, R 2 , R 3 and R 4 are D. In some embodiments, R 5 and R 6 are D. In some embodiments, R 5 and R ' are D. In some embodiments, R 5 and R 8 are D. In some embodiments, R 6 and R 7 are D. In some embodiments, R 6 and R 8 are D. In some embodiments, R 7 and R 8 are D. In some embodiments, R 3 , R 6 and R' are D. In some embodiments, R 5 , R 6 and R 8 are D. In some embodiments, R 5 , R'’ and R 8 are D. In some embodiments, R°, R ' and R 8 are D. In some embodiments, all instances of D are the same. In some embodiments, all instances of D are different.
  • R 4 , R 2 , R 3 , R 4 , R 3 , R 6 , R 7 and R 8 are independently A.
  • R 4 is A.
  • R 2 is A.
  • R 3 is A. In some embodiments, R 4 is A. In some embodiments, R 3 is A. In some embodiments, R 6 is A. In some embodiments, R' is A. In some embodiments, R 8 is A. In some embodiments, only one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R'’ and R 5 is A In some embodiments, at least two of R 1 , R 2 , R 3 , R 4 , R 3 , R 6 , R' and R 8 are A. In some embodiments, at least three of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are A.
  • At least four of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are A. In some embodiments, at most six of R 4 , R 2 , R 3 , R 4 , R ⁇ R 6 , R and R 5 are A. In some embodiments, at least one of R 1 , R 2 , R 3 and R 4 is A. In some embodiments, only one of R 1 , R 2 , R 3 and R 4 is A. In some embodiments, two of R 1 , R 2 , R 3 and R 4 are A. In some embodiments, three of R 3 , R 2 , R 3 and R 4 are A.
  • ail of R 1 , R 2 , R 3 and R 4 are A. in some embodiments, two or three of R 1 , R 2 , R 3 and R 4 are A. In some embodiments, at least one of R 5 , R 6 , R' and R 8 is A. In some embodiments, only one of R 5 , R 6 , R 7 and R 8 is A. In some embodiments, two of R 5 , R 6 , R 7 and R 8 are A. in some embodiments, three of R 5 , R b , R' and R 8 are A. In some embodiments, ail of R 5 , R 6 , R 7 and R 8 are A.
  • R 5 , R°, R 7 and R 8 are A.
  • at least one of R 3 , R z , R 3 and R 4 is A, and at least one of R 5 , R 6 , R ? and R 8 is A.
  • at least two of R 3 , R 2 , R 3 and R 4 are A, and at least one of R’, R 6 , R' and R 8 is A.
  • at least one of R 3 , R 2 , R 3 and R 4 is A, and at least two of R 5 , R°, R' and R 8 are A.
  • R 1 , R 2 , R 3 and R 4 are A, and at least two of R 5 , R 6 , R/' and R 8 are A. In some embodiments, at least three of R 1 , R 2 , R 3 and R 4 are A, and at least two of R 5 , R b , R 7 and R s are A. In some embodiments, R 1 and R 2 are A. In some embodiments, R 1 and R J are A. In some embodiments, R 1 and R 4 are A. In some embodiments, R 2 and R J are A. In some embodiments, R 2 and R 4 are A. In some embodiments, R 3 and R 4 are A. In some embodiments, R 1 , R 2 and R 3 are A.
  • R 1 , R 2 and R 4 are A. In some embodiments, R 1 , R J and R 4 are A. In some embodiments, R 2 , R 3 and R 4 are A. In some embodiments, R 5 and R 6 are A. In some embodiments, R 5 and R 7 are A. In some embodiments, R 5 and R 8 are A. In some embodiments, R 6 and R' are A. In some embodiments, R 6 and R 8 are A. In some embodiments, R 7 and R 8 are A. In some embodiments, R 5 , R 6 and R ? are A. In some embodiments, R 3 , R° and R 8 are A. In some embodiments, R 5 , R 7 and R 8 are A.
  • R°, R' and R 8 are A. In some embodiments, all instances of A are the same. In some embodiments, ail instances of A are different. In Formula (I), one or more of R 3 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently
  • R 3 , R 2 , R 3 , R 4 , R 3 , R 6 , R 7 and R 8 are independently A; and the other remaining R 1 , R 2 , R 3 , R 4 , R 5 , R b , R' and R 8 are independently selected from H, deuterium, substituted or unsubstituted alkyl, and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl in some embodiments, all of the other remaining R 3 , R , R J , R 4 , R 5 , R°, R' and R 8 are H.
  • At least one of the other remaining R 1 , R 2 , R J , R 4 , R 5 , R 6 , R ? and R 8 is alkyl that can be substituted with one or more substituents independently selected from deuterium and aryl.
  • At least one of the other remaining R 1 , R 2 , R 3 , R 4 , R 3 , R b , R' and R 8 is and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl in some embodiments, all of the other remaining R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R ' and R 8 are independently selected from H, deuterium and aryl that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl in some embodiments, all of the oilier remaining R 1 , R 2 , R 3 , R 4 , R 5 , R°, R' and R 8 are independently selected from H, deuterium and unsubstituted phenyl.
  • At least one of the other remaining R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R' and R 8 is unsubstituted phenyl.
  • all of the other remaining R 1 , R 2 , R 3 and R 4 are H.
  • all of the other remaining R 1 , R 2 , R 3 and R 4 are independently selected from deuterium; alkyl that can be substituted with one or more substituents independently selected from deuterium and aryl; and and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl.
  • all of the other remaining R 1 all of the other remaining R 1 .
  • R 2 , R 3 and R 4 are aryl that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl. In some embodiments, all of the other remaining R 1 , R 2 , R 3 and R 4 are unsubstituted phenyl. In some embodiments, all of the other remaining R 5 , R b , R' and R 8 are H. In some embodiments, at least one of the other remaining R 5 , R 6 , R 7 and R 8 are independently selected from deuterium; alkyl that can be substituted with one or more substituents independently selected from deuterium and aryl: and and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl.
  • At least one of the other remaining R 5 , R 6 , R 7 and R 8 is and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl. In some embodiments, at least one of the other remaining R 5 , R 6 , R ' and R 8 is unsubstituted phenyl. In some embodiments, at least one of the other remaining R 1 , R 2 ,
  • R5 and R 4 is unsubstituted phenyl, and at least one of the other remaining R 3 , R 6 , R 7 and R 8 is unsubstituted phenyl.
  • all instances of alkyl that that can be substituted with one or more substituents independently selected from deuterium and aryl is selected from methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl and n-butyl.
  • two or more of R ! , R 2 , R 3 and R 4 taken together can form a ring system
  • two or more of R 5 , R 6 , R' and R 8 taken together can form a ring system.
  • the ring system here is substituted or unsubstituted aromatic ring. In some embodiments, the ring system here is substituted or unsubstituted aliphatic ring. In some embodiments, none of R 1 , R 2 , R 3 and R 4 are taken together to form a ring system, and none of R 5 , R 6 , R 7 and R 8 are taken together to form a ring system. In some embodiments, R 4 and R 5 are not taken together to form a ring system.
  • A is selected from CN-L A -*, PFA-L 4 -* or Het- L 4 -*. Each represents a point of attachment to Formula (I).
  • PFA is perfluoroalkyl. In some embodiments, PFA is perfluoroalkyl having 1 to 10 carbon atoms. In some embodiments, PFA is perfluoroalkyl having 1 to 3 carbon atoms in some embodiments, PFA is trifluoromethyl. Het is substituted or unsubstituted heteroaryl having at least one nitrogen atom as a ring-constituting atom.
  • L 4 is independently selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene; wherein each instance of arylene and heteroarylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; and two or more of these substituents taken together can form a ring system.
  • CN-L 4 - is substituted or unsubstituted 4-cyanoplienyi, substituted or unsubstituted 3-eyanophenyl, substituted or unsubstituted 2-cyanophenyI, or substituted or unsubstituted 3,5-dicyanophenyl.
  • CN-L A - is unsubstituted 4-cyanopheny], unsubstituted 3-cyanophenyl, unsubstituted 2-cyanophenyl, or unsubstituted 3,5-dicyanophenyI.
  • Het-L A ⁇ . , , , . bond or substituent is not limited to, a single substituent.
  • R 2i , R 22 , R 23 , R 24 and R 25 are independently H, CN, substituted or unsubstituted alkyl, substituted or unsubstituted ary], or substituted or unsubstituted heteroaryl.
  • alkyl can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted and, and substituted or unsubstituted heteroaryl.
  • Each instance of aryl and heteroaryl can 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 these substituents taken together can form a ring system.
  • the ring system here is substituted or unsubstituted aromatic ring, or substituted or unsubstituted aliphatic ring.
  • L A and L u are independently selected from single bond, substituted or unsubstituted aiyiene, and substituted or unsubstituted heteroaiyiene.
  • L A and L 11 has two or three substituted or unsubstituted arylenes bonded together. In some embodiments, L A and L 11 consists of only one substituted or unsubstituted arylene. in some embodiments, L A and L 11 has two or three substituted or unsubstituted heteroaryienes bonded together. In some embodiments, L A and L 11 consists of only one substituted or unsubstituted heteroaiyiene.
  • each instance of aiyiene and heteroaiyiene is unsubstituted or substituted with one or more substituents independently selected from deuterium, halogen, cyano, alkyl, and, heteroaryl and combinations of two or more of them; and two or more of these substituents taken together can form a ring system in some embodiments, the ring system here is substituted or unsubstituted aromatic ring, or substituted or unsubstituted aliphatic ring in some embodiments, L A and L 11 are single bond, unsubstituted phenylene, or phenylene substituted with at least one alkyl. In some embodiments, L A and L 11 are single bond. In some embodiments, L A and L u are substituted or unsubstituted aiyiene, or substituted or unsubstituted heteroarylene.
  • A is selected from the group consisting of A1 to A16 shown below.
  • Het is selected from the group consisting of A2, A3, A4, A5, A6, A10, All, A12, A15 and A16. in All), All, A12, R is independently hydrogen or unsubstituted phenyl.
  • A is selected from the group consisting of Ai, A2, A15 and A16.
  • X' is R D '-N. In some embodiments. X' is O. In some embodiments, X' is S.
  • L D is independently selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroaryiene; wherein each instance of arylene and heteroaryiene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; and two or more of these substituents taken together can form a ring system.
  • L D is substituted or unsubstituted arylene.
  • I. D is substituted or unsubstituted heteroaryiene.
  • R° are hydrogen. In some embodiments, R D are deuterium. In preferred embodiments, at least one of R° is not hydrogen atom. In preferred embodiments, at least one of R° is substituted or unsubstituted alkyl, substituted or unsubstituted afkoxy, substituted or unsubstituted ammo, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted beteroaryloxy, or silyl.
  • At least one of R D is substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heieroaryloxy . In still more preferred embodiments, at least one of R D is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
  • R° are independently hydrogen or substituted or unsubstituted alkyl. In some embodiments, R° are independently hydrogen or substituted or unsubstituted alkoxy. In some embodiments, R D are independently hydrogen or substituted or unsubstituted amino.
  • R D are independently hydrogen or substituted or unsubstituted aryl.
  • R° are independently hydrogen or substituted or unsubstituted aryloxy.
  • R° are independently hydrogen or substituted or unsubstituted heteroaryl.
  • R° are independently hydrogen or substituted or unsubstituted heieroaryloxy.
  • R D are independently hydrogen or silyl. In some embodiments, two or more instances of R° are taken together to form a ring system.
  • R D at 3-position of the diphenylamino is substituted and the other R D are hydrogen.
  • R° at 3- and 3'-positions of the diphenylamino are substituted and the other R° are hydrogen.
  • R° at I -position of the diphenylamino and R° at 2-position of the diphenylamino are taken together to form a ring system in some embodiments of Formula (Ila), R D at 2-position of the diphenylamino and R D at 3- position of the diphenylamino are taken together to form a ring system.
  • R° at 3-position of the diphenylamino and R D at 4- position of the dipheny lamino are taken together to form a ring system.
  • R D at 3-position of the carbazole ring is substituted and the other R° are hydrogen.
  • R D at 3- and 6-positions of the carbazole ring are substituted and the other R° are hydrogen.
  • R° at 1 -position of the carbazole ring and R D at 2-position of the carbazole ring are taken together to form a ring system.
  • R D at 3-position of the carbazole ring is substituted and the other R° are hydrogen.
  • R D at 3- and 6-positions of the carbazole ring are substituted and the other R° are hydrogen.
  • R° at 1 -position of the carbazole ring and R D at 2-position of the carbazole ring are taken together to form a ring system.
  • Formula (Tic) L° bonds to 5-position of the carbazole ring in some embodiments of Formula (lie), L° bonds to 6-position of the carbazole ring. In some embodiments of Formula (lie), L D bonds to 7-position of the carbazole ring. In some embodiments of Formula (lie), L° bonds to 8-position of the carbazole ring.
  • R D at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), R D at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), R D at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), R D at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), R D at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), R D at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), R D at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), R D at 2-position of the indole ring is substituted and the other R° are hydrogen
  • R° ’ is hydrogen. In some embodiments, R° is deuterium. In some embodiments, R D is substituted or unsubstituted alkyl. In some embodiments, R D is substituted or unsubstituted amino. In some embodiments, R° is substituted or unsubstituted aryl. In some embodiments, R° is substituted or unsubstituted heteroaryl. In some embodiments, two or more instances of R D and R° taken together can form a ring system.
  • L° is a single bond.
  • L D is substituted or unsubstituted arylene, or substituted or unsubstituted heteroaiylene.
  • L° is substituted or unsubstituted aiyiene.
  • I, D is substituted or unsubstituted heteroarylene.
  • C-R D of the benzene rings in Formulae (Iia), (lib) (tie) and (lid) may be substituted with N. In some embodiments, only one of C-R D of the benzene ring is substituted.
  • Each in Formulae (Iia), (lib), (lie) and (lid) represents a point of attachment to Formula (I).
  • D is selected from the group consisting of D1 to D97 shown below.
  • D is selected from the group consisting of DI, D4, D21, F76, D86, D94, D96 and D97.
  • L 11 , L A and L D are selected from the group consisting of
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 1") satisfying that Y 1 is R ! -C, Y 2 is R ? -C, Y 3 is R 3 -C, Y 4 IS R 4 -C, Y 5 IS R 5 -C, Y 6 is R 6 -C, Y 7 is R 7 -C, and Y 8 is R 8 -C; R 5 , R 6 , R 7 and R 8 are H; at least one of R 1 , R 2 , R 3 and R 4 is D; at least one of R 1 , R 2 , R J and R 4 is
  • two of R 1 , R 2 , R 3 and R 4 are D. In some embodiments of Group 1, two of R 1 , R 2 , R 3 and R 4 are D; one of R 1 , R 2 , R 3 and R 4 is A; and the remaining one is H In some embodiments, two of R 1 , R 2 , R J and R 4 are D; one of R 1 , R 2 , R 3 and R 4 is A; and the remaining one is substituted or unsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl.
  • two D's are the same. In some embodiments, two D's are different from each other.
  • R 1 is A, two of R 2 , R 3 and R 4 are D, and the remaining one is H.
  • R 2 is A, two of R 1 , R 3 and R 4 are D, and the remaining one is H.
  • R 3 is A, two of R f , R 2 and R 4 are D, and the remaining one is H.
  • R 4 is A, two of R 1 , R 2 and R are D, and the remaining one is H.
  • R 1 is A, R is H, and R 3 and R 4 are D wherein two D's are the same.
  • R 1 is A, R 2 is H, and R 3 and R 4 are D wherein two D's are different from each other.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 2") satisfying that Y 1 is Rf-C, Y 2 is R 2 -C, Y 3 IS R 3 -C, Y 4 IS R 4 -C, Y 5 is R 5 -C, Y 6 is R ! -il Y 7 is R -C. and Y 8 is R 8 -C; at least one of R 1 , R 2 , f and R 4 is D; and at least one of R 5 , R 6 , R 7 and R s is D.
  • two of R 1 , R 2 , R ' and R 4 are D, and one of R 5 , R 6 , R 7 and R 8 is D.
  • one of R 1 , R 2 , R and R 4 are D
  • one of R 5 , R 6 , R 7 and R 8 is D.
  • two of R 4 , R 2 , R 3 and R 4 are D; one of R 1 , R 2 , R 3 and R 4 is A; the remaining one of R 1 , R 2 , R 3 and R 4 is H; one of R 5 , R 6 , R' and R 8 is D; and the remaining three of R 5 , R 6 , R 7 and R 8 are H.
  • two of R 3 , R 2 , R 3 and R 4 are D; one of R 1 , R 2 , R 3 and R 4 is A; the remaining one of R 1 , R 2 , R 3 and R 8 is D.
  • R 4 is H; one of R 5 , R 6 , R' and R 8 is D; one of R 5 , R°, R' and R 8 is A; and the remaining two of R 5 , R 6 , R 7 and R 8 are H.
  • two or more D's are the same. In some embodiments, two or more D's are different from each other.
  • R 1 is A, R 2 is H, R 3 and R 4 are B wherein two D's are the same; R 6 is D; and R 5 , R ; and R 8 are H.
  • R 1 is A, R 2 is H, R 3 and R 4 are D wherein two D's are different from each other; R° is D; and R 3 , R 7 and R 8 are H.
  • R 1 is A, R 2 is H, R 3 and R 4 are D wherein two D's are the same; R 7 is D; and R 5 , R 6 and R 8 are H.
  • R 1 is A, R 2 is H, R 3 and R 4 are D wherein two D's are different from each other; R ; is D; and R 5 , R 6 and R 8 are H.
  • R 5 is A, R 4 is H, R 2 and R 3 are D wherein two D's are the same; R is D; and R 5 , R 6 and R 8 are H.
  • R 1 is A, R 4 is H, R 2 and R 3 are D wherein two D's are different from each other; R ; is D; and R 5 , R b and R 8 are H.
  • R f is A, R 2 is H, R 3 and R 4 are D wherein two D's are the same; R 6 is A; R is D; and R 5 and R 8 are H.
  • R 1 is A, R 2 is H, R 3 and R 4 are D wherein two D's are different from each other; R 6 is A; R 7 is D; and R 5 and
  • R 8 are H.
  • R 3 is A, R 2 is H, R 3 and R 4 are D wherein two D's are the same; R 6 is D; and R 3 , R 7 and R 8 are H.
  • 1 is A, R 2 is H, R 3 and R 4 are D wherein two D's are different from each other; R 6 is D; and R 5 , R 7 and R 8 are H.
  • R 1 is A, R 2 is H, R 3 and R 4 are D wherein two D's are the same; R 6 is A; R 7 is D; and R 5 and R 8 are H.
  • R 1 is A, R 2 is H, R 3 and R 4 are D wherein two D's are different from each other; R 6 is A; R 7 is D; and R 5 and R 8 are H.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 3”) satisfying that one of Y 1 , Y 2 , Y 3 and Y 4 is N, Y 5 is R 5 -C, Y 6 is R 6 -C, Y 7 is R 7 -C, Y 8 is R s -C; at least one of R 1 , R 2 , R 3 and R 4 is D; none of R 3 , R b , R 7 and R 8 is D.
  • Group 3 group satisfying that one of Y 1 , Y 2 , Y 3 and Y 4 is N, Y 5 is R 5 -C, Y 6 is R 6 -C, Y 7 is R 7 -C, Y 8 is R s -C; at least one of R 1 , R 2 , R 3 and R 4 is D; none of R 3 , R b , R 7 and R 8 is D.
  • Rl R 2 , R 3 and R 4 are D, and one of Rl R 2 , R 3 and R 4 is A; and R 5 , R 6 , R 7 and R 8 are H.
  • Y 3 is R 3 -C, Y 2 is N, Y 3 is R 3 -C, Y 4 is R 4 -C.
  • Y 3 is R 3 -C, Y 2 is R 2 -C, Y 3 is N, Y 4 is R 4 -C.
  • R ’ is A, Y 2 is N, R 3 and R 4 are D wherein two D's are the same; and R 5 , R b , R 7 and R 8 are H.
  • R 1 is A, Y 2 is N, R 3 and R 4 are D wherein two D's are different from each other; and R 5 , R 6 , R 7 and R 8 are H.
  • the compound of Formula (i) is selected from the group (which is hereinafter referred to as "Group 4") satisfying that Y 1 is R 1 -C.
  • Y 2 is R 2 -C
  • Y 3 is R 3 -C
  • Y 4 is R 4 -C
  • one of Y 3 , Y 6 , Y 1 and Y 8 is N; at least one of R 1 R z , R 3 and R 4 is D; none of R 5 , R 6 , R ; and R 8 is D
  • R 1 , R 2 , R 3 and R 4 are D, and one of R 1 , R 2 , R 3 and R 4 is A; and R 5 , R b , R and R 8 are H.
  • Y 5 is N
  • Y 6 is R 6 -C
  • Y 7 is R ? -C
  • Y 8 is R 8 -C.
  • Y 5 is R s -C
  • Y 6 is R 6 ⁇ C
  • Y' is R/-C
  • R 1 and R 2 are D wherein two D's are the same, R 3 is A, R 4 is H, Y 5 is N, Y 6 is R 6 -C, Y 7 is R 7 -C, Y 8 is R s -C, and R 6 , R 7 and R 8 are H.
  • R 1 and R 2 are D wherein two D's are different from each other, R 5 is A, R 4 is H, Y 5 is N, Y 6 is R'-C.
  • Y 7 is R 7 -C, Y 8 is R s -C, and R 6 , R 7 and R 8 are H.
  • R f and R 2 are D wherein two D's are the same, R 3 is A, R 4 is H, Y 5 is R 3 -C,
  • Y b is R 6 -C
  • Y 7 is R 7 -C
  • Y 8 IS N
  • R 5 , R 6 and R are H.
  • R 1 and R 2 are D wherein two D's are different from each other
  • R J is A
  • R 4 is H
  • Y 5 is R 5 -C
  • Y 6 is R 6 -C
  • Y 7 is R 7 -C
  • Y 8 is N
  • R 5 , R 6 and R 7 are H.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 5") satisfying that one of Y 1 , Y 2 , Y 3 and Y 4 is N, Y 5 is R 5 -C, Y 6 is R'-C. Y 7 is R 7 -C, Y 8 is R S ⁇ C; at least one of R 1 , R ⁇ R 3 and R 4 is D; at least one of Rl R'l R 7 and R 8 is D.
  • Group 5 group satisfying that one of Y 1 , Y 2 , Y 3 and Y 4 is N, Y 5 is R 5 -C, Y 6 is R'-C.
  • Y 7 is R 7 -C, Y 8 is R S ⁇ C; at least one of R 1 , R ⁇ R 3 and R 4 is D; at least one of Rl R'l R 7 and R 8 is D.
  • R 1 , R 2 , R 3 and R 4 are D, and one of R 1 , R 2 , R ' and R 4 is A; one of R 5 , R 6 , R 7 and R 8 is D; and the remaining three of R 5 , R b , R 7 and R 8 are H
  • Y 1 is R f -C
  • Y 2 is N
  • Y 3 is R 3 -C
  • Y 4 is R 4 -C.
  • Y 1 is R l -C
  • Y 2 is R -C
  • Y 3 is N
  • Y 4 is R 4 -C.
  • R 1 is A
  • Y 2 is N
  • R J and R 4 are D wherein two D's are the same.
  • R 1 is A
  • Y z is N
  • R J and R 4 are D wherein two D's are different from each other.
  • R 6 is D
  • R 5 , R 7 and R 8 are H.
  • R 7 is D
  • R 5 , R b and R 8 are H.
  • R 1 is A, Y 2 is N, R J and R 4 are D wherein two D's are the same, R 7 is D, and R 3 , R° and R 8 are H.
  • R ! is A, Y 2 is N, R 3 and R 4 are D wherein two D's are different from each other, R 7 is D, and R 5 , R 6 and R 8 are H.
  • R 1 is A, Y 2 is N, R 3 and R 4 are D wherein two D's are the same, R° is D, and R 5 , R 7 and R 8 are H.
  • R 1 is A, Y 2 is N, R 3 and R 4 are D wherein two D's are different from each other, R 6 is D, and R 5 , R 7 and R 8 are H.
  • R 1 is A, Y 2 is N, R 3 and R 4 are D wherein two D's are the same, R 6 is A, R 7 is D, and R 5 and R 8 are H.
  • R f is A, Y 2 is N, R 3 and R 4 are D wherein two D's are different from each other, R 6 is A, R' is D, and R 3 and R 8 are H.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 6") satisfying that Y 1 is R f -C, Y' 2 is R 2 -C, Y 3 IS R 3 -C, Y 4 is R 4 -C, one of Y 5 , Y 6 , Y 7 and Y 8 is N; at least one of R ! , R 2 , R 3 and R 4 is D; at least one of R 5 , R 6 , R' and R 8 is D.
  • Group 6 group satisfying that Y 1 is R f -C, Y' 2 is R 2 -C, Y 3 IS R 3 -C, Y 4 is R 4 -C, one of Y 5 , Y 6 , Y 7 and Y 8 is N; at least one of R ! , R 2 , R 3 and R 4 is D; at least one of R 5 , R 6 , R' and R 8 is D.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 7") satisfying that one of Y 1 , Y 2 , Y 3 and Y 4 is N; one of Y 5 , Y 6 , Y 7 and Y 8 is N; at least one of R 1 , R 2 , R 3 and R 4 is D; none of R 5 , R 6 , R' and R 8 is D
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 8") satisfying that one of Y 1 , Y 2 , Y 3 and Y 4 is N; one of Y 5 , Y 6 , Y' and Y 8 is N; at least one of R 1 , R 2 , R 5 and R 4 is D; at least one of R 5 , R 6 , R 7 and R 8 is D.
  • Groups 1 to 8 are preferred in this order. Group 1 is the most preferred group and Group 2 is the second most preferred group.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 9") satisfying that at least one of Y 3 , Y' ⁇ . Y 7 and Y 8 is N.
  • Group 9 at least two of R 1 , R 2 , R 3 and R 4 are D or A.
  • none of R 3 , R°, R' and R 8 are D, and none of R 3 , R 6 , R 7 and R 8 are A.
  • the number of D and A in R 1 , R 2 , R 3 and R 4 is not smaller than the number of D and A in R 5 , R 6 , R ? and R 8 .
  • At least one of Y 1 , Y 2 , Y 3 and Y 4 is N. In some embodiments, Y 4 is N. In some embodiments, Y 4 is N; Y 3 is R 3 -C; and R 3 is A.
  • Y 3 is R J -C; and R 3 is A. in some embodiments of Group 9, Y 3 is R 3 -C; R 3 is A; and none of Y 1 , Y 2 , Y 3 and Y 4 are N.
  • Y 5 is N.
  • Y b is N.
  • Y 7 is N.
  • Y 8 is N.
  • one of Y 5 , Y b , Y 7 and Y 8 is N; none of R 5 , R 6 , R 7 and R 8 are D; and none of R 5 , R 6 , R 7 and R 8 are A.
  • one ofY 5 , Y°, Y 7 and Y 8 is N; at least two of R 1 , R 2 , R 3 and R 4 are D: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • one of Y 5 , Y°, Y ' and Y 8 is N; two of IV.
  • R 2 , R 3 and R 4 are D: other one of R 1 , R 2 , R 3 and R 4 is A; and the other one of R 1 , R 2 , R 3 and R 4 is H or unsubstituted phenyl.
  • one of Y 5 , Y' and Y 8 is N; Y 6 is R°-C; R° is D; at least two of R 1 , R 2 , R 3 and R 4 are D: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • one of Y 3 , Y 7 and Y' 8 is N: Y 6 is R 6 -C; R b is B; two of R 1 , R 2 , R 3 and R 4 are D: other one of R 1 , R 2 , R 3 and R 4 is A; and the other one of R 1 , R 2 , R 3 and R 4 is H or unsubstituted phenyl.
  • one of Y ⁇ Y 6 , Y' and Y 8 is N; one of R 5 , R 6 , R 7 and R 8 is D. In some embodiments, one of Y 3 , Y 7 and Y 8 is N; Y 6 is R b -C; and R f is D. In some embodiments, Y 4 and Y 3 are N; Y 6 is R 6 - C; and R 6 is D. In some embodiments, Y 4 and Y' are N; Y 6 is R b -C; and R b is D. In some embodiments, Y 4 and Y 8 are N; Y b is R°-C; and R° is D.
  • Y 4 and Y 3 are N; Y 6 is R 6 -C; R 6 is D; at least two of R 5 , R 2 , R 3 and R 4 are D: and at least one of R ! , R 2 , R 3 and R 4 is A.
  • Y 4 and Y 7 are N; Y 6 is R 6 -C; R b is D; at least two of R 1 , R 2 , R 3 and R 4 are D: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • Y' 4 and Y 8 are N; Y 6 is R 6 -C; R 6 is D; at least two of R 5 , R 2 , R 3 and R 4 are D: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • one of Y 5 , Y 6 and Y 8 is N; Y 7 is R 7 -C; R 7 is B; at least two of R 1 , R 2 , R 3 and R 4 are D: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • one of Y 5 , Y 6 and Y 8 is N; Y 7 is R ?
  • R 7 is D: two of R 3 , R 2 , R 3 and R 4 are B: other one of R 1 , R 2 , R 3 and R 4 is A; and the other one of R 1 , R 2 , R 3 and R 4 is H or unsubstituted phenyl.
  • one of Y 5 , Y 6 and Y 8 is N; Y' is R'-C; and R' ' is D.
  • Y 4 and Y 5 are N; Y 7 is R 7 -C; and R 7 is D.
  • Y 4 and Y 6 are N; Y' is R'-C; and R 7 is D.
  • Y 4 and Y 8 are N; Y 7 is R 7 -C; and R 7 is D.
  • Y' 4 and Y 5 are N; Y' ' is R'-C; R 7 is D; at least two of R 1 , R 2 , R 3 and R 4 are B: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • Y 4 and Y 6 are N; Y ' is R' ⁇ C; R ; is D; at least two of R f , R 2 , R 3 and R 4 are B: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • Y 4 and Y 8 are N; Y' is R'-C; R' is D; at least two of R 1 , R 2 , R 3 and
  • R 4 are D: and at least one of R 1 , R 2 , R 3 and R 4 is A.
  • Y 3 is N;
  • Y 6 is R’-C:
  • Y 7 is R -C; and
  • R 6 and R 7 are D.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 10") satisfying the following conditions: none of Y 1 , Y 2 , Y 3 and Y 4 are N; or one ofY 1 , Y 2 , Y 3 and Y 4 is N; two of R 1 , R 2 , R J and R 4 are independently D; other one of R 1 , R 2 , R 3 and R 4 is A: when none of Y 1 , Y 2 , Y 3 and Y 4 are N, the remaining one of R 1 , R 2 , R 3 and R 4 is selected from H.
  • Group 10 group satisfying the following conditions: none of Y 1 , Y 2 , Y 3 and Y 4 are N; or one ofY 1 , Y 2 , Y 3 and Y 4 is N; two of R 1 , R 2 , R J and R 4 are independently D; other one of R 1 , R 2 , R 3 and R 4 is A: when none of
  • Y 7 is R 7 -C, then R 7 is H; and when Y 8 is R S ⁇ C, then R 8 is H.
  • none of Y 1 , Y 2 , Y 3 and Y 4 are N. in some embodiments, one of Y 1 , Y 2 , Y ⁇ 3 and Y 4 is N.
  • R 1 and R 2 are independently D; at least one of R 3 and R 4 is A.
  • R 3 and R 3 are independently D; at least one of R 2 and R 4 is A.
  • R f and R 4 are independently D; at least one of R 2 and R 3 is A.
  • R 2 and R' are independently D; at least one of R 1 and R 4 is A.
  • R 2 and R 4 are independently D: at least one of R 1 and R 3 is A.
  • R 3 and R 4 are independently D; at least one of R 1 and R 2 is A. In some embodiments, the remaining one of R 1 , R 2 , R 3 and R 4 is selected from H, deuterium, unsubstituted alkyl and imsubstituted phenyl. In some embodiments, the remaining one of R 1 , R z , R 3 and R 4 is selected from H and imsubstituted phenyl. In some embodiments, none of Y 5 , Y 6 , Y' and Y 8 are N. In some embodiments, two of Y 5 , Y b , Y 1 and Y s are N.
  • one of Y ⁇ Y°, Y ' and Y 8 is N.
  • Y 5 is N.
  • Y 6 is N.
  • Y' is N.
  • Y 8 is N.
  • one of Y' 5 , Y 6 , Y 7 and Y 8 is N; R 3 is A.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 11") satisfying that only one of R 5 , R 6 , R 7 and R s is D.
  • Group 11 R 5 is D.
  • R 6 is B.
  • R 7 is D.
  • R 8 is D.
  • one of R 5 , R 6 , R' and R 8 is D; and the others of R 5 , R°, R ; and 8 are not A.
  • one of R 5 , R 6 , R 7 and R s is D; and the others of R 5 , R 6 , R 7 and R s are H.
  • one of Y 5 , Y 6 , Y 7 and Y 8 is N.
  • Y 5 is N.
  • Y t is N.
  • Y 3 is N.
  • Y 8 is N.
  • one of Y 5 , Y 6 , Y 7 and Y 8 is N;
  • R 3 is A.
  • one of Y 3 , Y 6 , Y 7 and Y 8 is N; and none of Y 1 , Y ⁇ 2 , Y 3 and Y 4 are N.
  • one of Y' 5 , Y 6 , Y' and Y 8 is N: and one of Y 1 , Y 2 , Y 3 and Y 4 is N.
  • one of Y 5 , Y 6 , Y 1 and Y 8 is N; and Y 4 is N.
  • Y ⁇ 4 and Y 3 are N.
  • Y 4 and Y° are N.
  • Y ⁇ 4 and Y' are N in some embodiments, Y 4 and Y 8 are N.
  • R 6 is D; two of R 1 , R 2 , R 3 and R 4 are D; at least one of R 1 , R 2 , R 3 and R 4 is A.
  • R 6 is B; two of R 1 , R 2 , R 3 and R 4 are D; one of R 1 , R 2 , R 3 and R 4 is A, the other remaining one of R 1 , R 2 , R J and R 4 is H or unsubstituted phenyl in some embodiments, R ' is D; two of R 1 , R 2 , R 3 and R 4 are D; at least one of R 1 , R 2 , R 3 and R 4 is A.
  • R 7 is D; two of R 1 , R 2 , R 3 and R 4 are D; one of R 1 , R 2 , R 3 and R 4 is A, the other remaining one of R 1 , R 2 , R 3 and R 4 is H or unsubstituted phenyl.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 12") satisfying that Y 6 is R 6 -C; Y' is R 7 -C; R 6 and R 7 are independently D; and at least one of Y 1 , Y 2 , Y 3 , Y 4 , Y 3 and Y 8 is N.
  • one or two of Y 3 , Y 2 , Y 3 and Y 4 are N; and none of Y 3 and Y s are N. In some embodiments, none of Y 1 , Y 2 , Y 3 and Y 4 are N; and at least one of Y 3 and Y 8 is N. In some embodiments, one of Y 1 , Y 2 , Y 3 and Y 4 is N; and one of Y 5 and Y 8 is N. In some embodiments, Y 4 is N; and one of Y 5 and Y 8 is N. In some embodiments, at least one of Y 1 , Y 2 , Y 3 and Y 4 is N; and R 3 is A.
  • R 1 and R 2 are independently D; at least one of R 3 and R 4 is A. In some embodiments, R 1 and R 3 are independently D; at least one of R 2 and R 4 is A. In some embodiments, R f and R 4 are independently D; at least one of R 2 and R 3 is A. In some embodiments, R 2 and R 3 are independently D; at least one of R 1 and R 4 is A. In some embodiments, R 2 and R 4 are independently D; at least one of R 1 and R 3 is A. In some embodiments, R 3 and R 4 are independently D; at least one of R 1 and R z is A.
  • the remaining one of R 5 , R 2 , R 3 and R 4 is selected from H, deuterium, unsubstituted alkyl and unsubstituted phenyl. In some embodiments, the remaining one of R 1 , R 2 , R 3 and R 4 is selected from H and unsubstituted phenyl.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 13") satisfying that Y b is R f -C; Y 7 is R 7 -C; R 6 and R 7 are independently D; none of Y 1 , Y 2 , Y 3 , Y 4 , Y 3 , Y 6 , Y 7 and Y 8 are N; and two of R 1 , R 2 , R 3 and R 4 are independently D and these two differ from each other.
  • R 1 and R 2 are independently B; at least one of R J and R 4 is A. in some embodiments, R 1 and R 3 are independently D; at least one of R 2 and R 4 is A. in some embodiments, R 1 and R 4 are independently D; at least one of R 2 and R 3 is A. In some embodiments, R 2 and R 3 are independently D; at least one of R 1 and R 4 is A. In some embodiments, R and R 4 are independently D; at least one of R 1 and R J is A. In some embodiments, R J and R 4 are independently D; at least one of R 1 and R 2 is A.
  • the remaining one of R 1 , R 2 , R 3 and R 4 is selected from H, deuterium, unsubstituted alkyl and unsubstituted phenyl. In some embodiments, the remaining one of R 1 , R z , R J and R 4 is selected from H and unsubstituted phenyl In some embodiments, R 5 and R 8 are selected from H, unsubstituted phenyl In some embodiments, R s and R 8 are H.
  • the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 14") satisfying at least one of the foil owing conditi ons :
  • Y ' is R 5 -C, and R 5 is A;
  • Y 7 is R 7 -C, and R' is A;
  • R f and R 2 are independently D: at least one of R' and R 4 is A. in some embodiments, R ! and R 3 are independently D; at least one of R 2 and R 4 is A. In some embodiments, R 1 and R 4 are independently D; at least one of R 2 and R 3 is A. In some embodiments, R 2 and R 3 are independently D; at least one of R 1 and R 4 is A.
  • R 2 and R 4 are independently D; at least one of R 1 and R J is A. In some embodiments, R J and R 4 are independently D; at least one of R 1 and R z is A In some embodiments, the remaining one of R 1 , R 2 , R J and R 4 is selected from H, deuterium, unsubstituted alkyl and unsubstituted phenyl. In some embodiments, the remaining one of R 1 , R 2 , R' and R 4 is selected from H and unsubstituted phenyl in some embodiments, one of Y 5 , Y b , Y 7 and Y 8 is N. In some embodiments, Y 5 is N. in some embodiments, Y 6 is N.
  • Y ? is N.
  • Y 8 is N. in some embodiments, one of Y 1 , Y 2 , Y 3 and Y 4 is N. in some embodiments, Y 1 is N. In some embodiments, Y 2 is N. In some embodiments, Y 3 is N. in some embodiments, U 4 is N. in some embodiments, one of Y 1 , Y 2 , Y 3 and Y 4 is N; and one of Y 5 , Y 6 , Y 7 and Y 8 is N. in some embodiments, Y 4 is N; and one of Y 5 , Y 6 , Y 7 and Y 8 is N. In some embodiments, one of Y 2 , Y 6 , 7 and Y 8 is N; and A 3 is A.
  • the compound of Formula (I) is selected from the compounds shown in the following tables.
  • the compounds in the tables are represented by the following formula wherein Y 1 is N or R ⁇ -I ⁇ -C, 2 is N or R 2 ' ⁇ L 2 -C, Y 3 is N or R 3 '-L 3 -C, Y 4 is N or R 4, -L 4 -C, Y 5 is N or R 5, -L 5 -C, Y 6 is N or R 6 '-L 6 -C, Y 7 is N or R 7, -L 7 - C, and Y 8 is N or R 8 '-LAC.
  • Zi represents nnsubstituted phenyl.
  • Compounds 6713 to 13426 are also exemplified that correspond to Compounds 1 to 6712 but has S instead of O at the position of X, respectively.
  • the compound of Formula (I) is selected from the following compounds.
  • the compound of Formula (I) is selected from the following compounds. In some embodiments, compounds of Formula (I) are substituted with deuterium.
  • compounds of Formula (I) are light-emitting materials.
  • compounds of Formula (I) are compound capable of emitting delayed fluorescence.
  • compounds of Formula (I) are light-emitting materials. In some embodiments, compounds of Formula (I) are assistant dopant materials. In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce light in ultraviolet region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nrn to about 500 nm, about 500 nm to about 600 iim, or about 600 mn to about 700 nm), or near-mfrared region.
  • the compounds of Formula (I) when excited via thermal or electronic means, can produce light in the red or orange region of the visible spectrum (e.g., about 620 mn to about 780 nm; about 650 nm). in some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce 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).
  • the compounds of Formula (I) when excited via thermal or electronic means, can produce light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm; about 510 nm). in some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm; about 475 nm).
  • Electronic properties of a library of small chemical molecules can be computed using known ab initio quantum mechanical computations. For example, using a time- dependent density functional theory using, as a basis set, the set of functions known as 6- 31G* and a Becke, 3 -parameter, Lee- Yang-Parr hybrid functional to solve Hartree-Fock equations (TD-DFT/B3LYP/6-31 G*), molecular fragments (moieties) can be screened which have HQMOs above a specific threshold and LUMOs below' a specific threshold, and wherein the calculated triplet state of the moieties is above 2.75 eV.
  • a donor moiety can be selected because it has a HOMO energy (e.g., an ionization potential) of greater than or equal to -6.5 eV.
  • An acceptor moiety (‘24”) can be selected because it has, for example, a LUMO energy' (e.g., an electron affinity) of less than or equal to -0.5 eV.
  • Hie linker moiety (“L”) can be a rigid conjugated sy stem which can, for example, sterical!y restrict the acceptor and donor moieties into a specific configuration, thereby preventing the overlap between the conjugated p system of donor and acceptor moieties.
  • the compound library' is filtered using one or more of the following properties: 1. emission near a certain wavelength;
  • the difference between the lowest single! excited state and the lowest triplet excited state at 77K ( D EST) 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.
  • the A E ST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV. less than about 0.02 eV. or less than about 0.01 eV.
  • a compound of Formula (1) exhibits a quantum yield of greater than 25%, such as about 3Q%, 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.
  • the compounds of Formula (I) can be synthesized by any method known to one of ordinary skills in the art.
  • the compounds are synthesized from the commonly available starting material.
  • the compound of Formula (I) wherein X is (), Y 1 is Ri-C, Y 2 is R 2 -C, Y 3 is R 3 ⁇ C, Y 4 is R 4 -C, R 1 , R 5 and R 4 are 9-carbazolyl, R 2 is CN, and R 5 , R 6 , R 7 and R s are H can be synthesized by the following scheme.
  • a film containing a compound of the present invention of Formula (I) can be formed in a wet process in a wet process, a solution prepared by dissolving a composition containing a compound of the present invention is applied to a surface and formed into a film thereon after solvent removal.
  • a wet process includes, though not limited thereto, a spin coating method, a slit coating method, a spraying method, an inkjet method (a spay method), a gravure printing method, an offset printing method, and a flexographic printing method.
  • a suitable organic solvent capable of dissolving a composition containing a compound of the present invention is selected and used in some embodiments, a substituent (for example, an alkyl group) capable of increasing solubility in an organic solvent can be introduced into the compound contained in the composition.
  • a substituent for example, an alkyl group
  • a film containing a compound of the present invention can be formed in a dry process.
  • a dry process includes a vacuum evaporation method, but is not limited thereto.
  • compounds to constitute a film can be vapor-eo-deposited from individual evaporation sources, or can be vapor-co-deposited from a single evaporation source of a mixture of the compounds.
  • a mixed powder prepared by mixing powders of compounds may be used, or a compression-molded body prepared by compressing the mixed powder may be used, or a mixture prepared by heating, melting and cooling compounds may he used.
  • a film whose composition ratio corresponds to the composition ratio of the plural compounds contained in the evaporation source can be formed.
  • a film having a desired composition ratio can be formed in a simplified manner.
  • a temperature at which the compounds to be vapor-co-deposited could have the same weight reduction ratio is identified, and the temperature can be employed as the temperature in vapor-codeposition.
  • An embodiment of the present disclosure provides the preparation of compounds of Formula (I) according to the procedures of the following example(s), using appropriate materials. Those skilled in the art will understand that known variations of the conditions and processes of the following preparative procedures can be used to prepare these compounds. Moreover, by utilizing the procedures described in detail, one of ordinary skill in the art can prepare additional compounds of the present disclosure.
  • an organic electroluminescent device carriers are injected from an anode and a cathode to a light-emitting material to form an excited state for the light-emitting material, with which light is emitted.
  • excitons that are excited to the excited singlet state are 25% of the total excitons generated, and the remaining 75% thereof are excited to the excited triplet state. Accordingly, the use of phosphorescence, which is light emission from the excited triplet state, provides a high energy utilization.
  • the excited triplet state has a long lifetime and thus causes saturation of the excited state and deactivation of energy through mutual action with the excitons in the excited triplet state, and therefore the quantum yield of phosphorescence may generally he often not high.
  • a delayed fluorescent material emits fluorescent light through the mechanism that the energy of excitons transits to the excited triplet state through intersystem crossing or the like, and then transits to the excited singlet state through reverse intersystem crossing due to triplet-triplet annihilation or absorption of thermal energy, thereby emitting fluorescent light.
  • a thermal activation type delayed fluorescent material emitting light through absorption of thermal energy is particularly useful for an organic electroluminescent device in the case where a delayed fluorescent material is used in an organic electroluminescent device, the excitons in the excited singlet state normally emit fluorescent light.
  • the excitons in the excited triplet state emit fluorescent light through intersystem crossing to the excited singlet state by absorbing the heat generated by the device.
  • the light emitted through reverse intersystem crossing from the excited triplet state to the excited singlet state has the same wavelength as fluorescent light since it is light emission from the excited singlet state, but has a longer lifetime (light emission lifetime) than the normal fluorescent light and phosphorescent light, and thus the light is observed as fluorescent light that is delayed from the normal fluorescent light and phosphorescent light.
  • the light may be defined as delayed fluorescent light.
  • Tire use of the thermal activation type exciton transition mechanism may raise the proportion of the compound in the excited singlet state, which is generally formed in a proportion only of 25%, to 25% or more through the absorption of the thermal energy after the earner injection.
  • a compound that emits strong fluorescent light and delayed fluorescent light at a low' temperature of lower than 1Q0°C undergoes the intersystem crossing from the excited triplet state to the excited singlet state sufficiently with the heat of the device, thereby emitting delayed fluorescent light, and thus the use of the compound may drastically enhance the light emission efficiency.
  • the compounds of the invention can be synthesized by any method known to one of ordinary skills in the art.
  • the compounds are synthesized from the commonly available starting material.
  • the various moieties can be assembled via linear or branched synthetic routes.
  • the solution of an organic layer was evaporated under vacuum and purified by flash column chromatography using ethyl acetate hexane (1 :4) as an eluent in order to remove starting materials the hydroxy group.
  • the crude reaction mixture was obtained about 2.5 g.
  • the crude reaction mixture (2.5 g, 8.25 mmol) and K2CO3 (24.75 mmol) were dissolved in DMF.
  • the solution was stirred for 3 hours at 70 Celsius degree under a nitrogen atmosphere and then cooled down to room temperature.
  • the reaction progress checked by TLC.
  • the solution was extracted using ethyl acetate and distilled water.
  • Solvent of the organic layer was evaporated under vacuum and purified by column chromatography using ethyl acetate:hexane (1 :4) as an eluent.
  • the white powdery- product was obtained about 2 g.
  • the solution was refluxed for 12h under a nitrogen atmosphere and then cooled down to room temperature.
  • the solution was extracted using ethyl acetate and distilled water.
  • the solution of an organic layer was evaporated under vacuum and purified by column chromatography using ethyl acetate:hexane (1:4) as a eluent.
  • the white powdery product was obtained about 2,20 g (47.7%).
  • reaction quenched by water and MeOH and the mixture and the precipitate was filtered, and was washed with MeOH.
  • the reaction product was isolated by column chromatography using a mixture of dichloromethane and hexane (2:1) as an eluent. The yellow' powdery product was obtained about 0.71 g (81.0%).
  • Compound 6712 synthesised in Example 2 was vapor-deposited on a quartz substrate by a vacuum vapor deposition method under a condition of a vacuum degree of 10 3 Pa or less, so as to form a thin film having a thickness of 70 nm.
  • Compound 6712 and PYD2Cz were also vapor-deposited from a separate vapor deposition source on a quartz substrate by vacuum vapor deposition method under a condition of a vacuum degree of 10 3 Pa or less, so as to form a thin film having a thickness of 100 nm and a concentration of Compound 6712 of 20% by weight.
  • the samples are irradiated with light having a wavelength of 300 nm at 300 , and thus the light emission spectrum was measured and designated as fluorescence.
  • the spectrum at 77K was also measured and designated as phosphorescence.
  • the lowest singlet energy (Si) and the lowest triplet energy (Ti) were estimated from the onset of fluorescence and phosphorescence spectmni respectively.
  • D EST was calculated from the energy gap between Si and Ti. Photoiuminescenee quantum yield (PLQY) and emission peak wavelength of fluorescent light ( l ) were measured.
  • the time resolved spectrum was obtained by excitation light 337nm with Streak Camera, and the component with a short light emission lifetime was designated as fluorescent light, whereas the component with a long light emission lifetime was designated as delayed fluorescent light.
  • the lifetimes of the fluorescent light component (x P rompt) and the delayed fluorescent light component (idsiay) were calculated from the decay curves. The measurement results are shown in the table below.
  • OLED Thin films were laminated on a glass substrate having formed thereon an anode formed of indium tin oxide (P ⁇ ) having a thickness of 50 nm, by a vacuum vapor deposition method at a vacuum degree of 1.0 x 10 4 Pa or less.
  • P ⁇ indium tin oxide
  • HAT-C is formed to a thickness of 60 n on ITO
  • TrisPCz is formed to a thickness of 30 nm.
  • PYD2Cz was formed to a thickness of 5 nm, and thereon Compound 6712 and PYD2Cz were then vapor-co-deposited from separate vapor deposition sources to fomi a layer having a thickness of 30 nm, which is designated as a light-emitting layer.
  • SF3-TRZ was formed to a thickness of 10 nm, and thereon SF3-TRZ (70wt%) and Liq were vapor-co-deposited to a thickness of 30 nm. Liq was then vacuum vapor-deposited to a thickness of 2 nm, and then aluminum (All was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing organic electroluminescent devices.

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Abstract

The present disclosure relates to compounds of Formula (I) as useful materials for OLED's. X is O or S; Y1 to Y8 are N or R-C; at least one of R is CN or heteroaryl; and at least other one of R is diarylamino.

Description

COMPOSITION OF MATTER
FOR USE IN ORGANIC LIGHT-EMITTING DIODES
MELA TED APPLICATIONS
This application claims the benefit of priority to United States Provisional Patent Application serial number 62/950,669, filed December 18, 2019, which is hereby expressly incorporated by reference, in its entirety, into the present application.
BACKGROUND
An organic light-emitting diode (OLED) is a light-emitting diode (LED) in which a film of organic compounds is placed between two conductors, which film emits light in response to excitation, such as an electric current. OLEDs are useful in lightings and displays, such as television screens, computer monitors, mobile phones, and tablets. A problem inherent in OLED displays is the limited lifetime of the organic compounds. OLEDs which emit blue light, m particular, degrade at a significantly increased rate as compared to green or red OLEDs. OLED materials rely on the radiati ve decay of molecular excited states (excitons) generated by recombination of electrons and holes in a host transport material. The nature of excitation results in interactions between electrons and holes that split the excited states into bright singlets (with a total spin of 0) and dark triplets (with a total spin of 1). Since the recombination of electrons and holes affords a statistical mixture of four spin states (one singlet and three triplet sublevels), conventional OLEDs have a maximum theoretical efficiency of 25%.
To date, OLED material design has focused on harvesting the remaining energy from the normally dark triplets. Recent work to create efficient phosphors, which emit light from the normally dark triplet state, have resulted in green and red OLEDs. Other colors, such as blue, however, require higher energy excited states which accelerate the degradation process of the OLED.
The fundamental limiting factor to the triplet-singlet transition rate is a value of the parameter jiffi/AEsi†, where H is the coupling energy due to hyperfine or spin-orbit interactions, and AEST IS the energetic splitting between singlet and triplet states. Traditional phosphorescent OLEDs rely on the mixing of singlet and triplet states due to spin-orbital (SO) interaction, increasing i¾, and affording a lowest emissive state shared between a heavy metal atom and an organic ligand. Tins results in energy harvesting i from all higher singlet and triplet states, followed by phosphorescence (relatively short lived emission from the excited triplet). The shortened triplet lifetime reduces triplet exciton annihilation by charges and other excitons. Recent work by others suggests that the limit to the performance of phosphorescent materials has been reached.
SUMMARY
The present disclosure relates to novel materials for OLEDs. In some embodiments, these OLEDs can reach higher excitation states without rapid degradation it has now been discovered that thermally activated delayed fluorescence (TADF), which relies on minimization of AEST as opposed to maximization of Hr,, can transfer population between singlet levels and triplet sublevels in a relevant timescale, such as, for example, Ips-lOms. The compounds described herein are capable of luminescing at higher energy excitation states than compounds previously described.
In one aspect, the present disclosure provides: [1] An organic light-emitting diode (OLED) comprising a compound of
Formula (I):
Figure imgf000003_0001
wherein: X is O or S,
Y1 is X or R’-C, Y2 is X or R2-C, Y3 is X or R3-C, Y4 is N or R4-C, Y5 is N or R5-C, Y6 is
X or R6~C, Y7 is X or R -C. and Y8 is N or R8-C, provided that at most two of Y!, Y2, YJ, Y4, Y5, Y6, Y' and Y8 are N, one or more of R1, R2, R3, R4, R5, R6, R and R8 are independently D, other one or more of Ry R2, R3, R4, R5, R°, R7 and R8 are independently A, the other remaining R1, R2, R3, R4, R5, R6, R; and R8 are independently selected from H, deuterium, substituted or unsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and pheny l can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl, two or more of R1, Rz, R3 and R4 taken together can form a ring system, two or more of R5, R6, R' and R8 taken together can form a ring system,
A is selected from CN-LA-*, PFA-I/ -* or Het- LA~* PFA is perfluoroalkyl,
Het is substituted or unsubstituted heteroaryl having at least one nitrogen atom as a ring-constituting atom,
D is group of Formula (lia), (lib), (Ik) or (lid):
Figure imgf000004_0001
(Ila) (lib) (lie) (lid)
X' is selected fromN-R0’, O and S;
R° is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ammo, substituted or un substituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and siiyi; two or more instances of RD taken together can form a ring system;
Rd’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted and, and substituted or unsubstituted heteroaryl; two or more instances of Rrb and RD taken together can form a ring system;
LD and LA are independently selected from single bond, substituted or unsubstituted aryiene, and substituted or unsubstituted heteroaiylene; wherein each instance of aryiene and heteroaryl ene can 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 these substituents taken together can form a ring system; C-RD of the benzene rings in Formulae (Ila), (lib), (lie) and (lid) may be substituted with N; and each represents a point of attachment to Formula (1).
[2] The organic light-emitting diode (OLED) according to [1], wherein A is CN-La-*, PFA-La-* or Het-LA-* in which LAof Het-LA-* is substituted or unsubstituted aryiene, and substituted or unsubstituted heteroaryiene; wherein each instance of aryiene and heteroaiylene can be substituted with one or more substituents independently selected from deuterium substituted or unsubstituted alkyl, substituted or unsubstituted aryi, and substituted or unsubstituted heteroaryi, and wherein two or more of these substituents taken together can form a ring system. [3] The organic light-emitting diode (OLED) according to [1] or [2], wherein at least one of D is a group of Formula (lib) and at least one of R° is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, or sifyl. [4] The organic light-emitting diode (OLED) according to any one of [1] to
[3], wherein at least one of D is a group of Formula (lib) and at least one C-RD of the benzene rings in Formula (lib) is substituted with N.
[5] The organic light-emitting diode (OLED) according to any one of j 1] to
[4], wherein at least one of D is a group of Formula (lib) and I,D is substituted or unsubstituted arylene, and substituted or unsubstituted heteroaiylene; wherein each instance of arylene and heteroaiylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, and wherein two or more of these substituents taken together can form a ring system. [6] The organic light-emitting diode (OLED) according to [1] or [2], wherein
D is group of Formula (Ha). (lie) or (lid)
[7] The organic light-emitting diode (OLED) according to any one of [1] to [6], wherein at least one of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 is N.
[8] The organic light-emitting diode (OLED) according to any one of [1] to [7], wherein at least one of R1, R2, R3 and R4 and at least one of R5, R6, R/' and R8 are independently D.
[9] The organic light-emitting diode (OLED) according to [8], wherein at least one of R6 and R/ is D
[10] The organic light-emitting diode (OLED) according to any one of [1] to [9], wherein two or more of R1, R2, R3, R4, R\ R6, R7 and Rs are independently A.
[11] The organic light-emitting diode (OLED) according to [10], wherein two of R1, R2, R3 and R4 are independently A and the other two of R1, R2, R J and R4 are independently D.
] 12] The organic light-emitting diode (OLED) according to any one of [1] to [11], wherein the organic light-emitting diode has a light-emitting layer comprising the compound of Formula (1) as an assistant dopant.
[13] The organic light-emitting diode (OLED) according to any one of [1] to
[12], wherein the organic light-emitting diode has a light-emitting layer comprising a host material, the compound of Formula (1) and a light-emitting material; and the compound of Formula (I) has a lowest excited singlet energy' level between the lowest excited singlet energy level of the host material and the lowest excited singlet energy level of the light-emitting material.
[14] The organic light-emitting diode (OLED) according to any one of [1] to [12], wherein the Formula (1) does not include a compound wherein Y1 is Rd-C, Y2 is R2- C, Y3 is R -C. Y4 is R4-C, Y5 is Rs-C, Y6 is R' -C. Y7 is R -C. Y8 is RS~C, only one of R’, R2, R3, R4, R5, R6, R7 and R8 is A, A is selected from
Figure imgf000006_0001
R21, R22, R23, R24 and R25 are independently substituted or unsubstiiuted aryl, or substituted or unsubstituted heteroaryl, L11 is single bond, D is group of Formula (lib), LD is single bond, and C-R° of the benzene rings in Formula (lib) is not substituted with N.
[15] The organic light-emitting diode (OLED) according to any one of [1] to [12], wherein the Formula (1) does not include a compound wherein Y1 is Rl-C, Y2 is R2- C, Y3 is R3-C, Y4 IS R4-C, Y5 IS R5-C, Y6 is R6-C, Y7 is R7-C, Y8 is Rs-C, only one of R'1, R2, R3, R4, R5, R6, R7 and R8 is A, A is selected from
Figure imgf000006_0002
R21, R22, R2 , R24 and R25 are independently substituted or unsubstiiuted aryl, or substituted or unsubstituted heteroaryl, L“ is single bond, D is group of Formula (lib), LD is single bond, R° is hydrogen, and C-RD of the benzene rings in Formula (lib) is not substituted with N.
[16] The organic light-emitting diode (OLED) according to any one of [I] to [15], wherein the compound of Formula (I) emits light.
] 17] The organic light-emitting diode (OLED) according to any one of [1 ] to
[15], wherein light emission of the organic light-emitting diode occurs most in the compound of Formula (1).
[18] The organic light-emitting diode (OLED) according to any one of [ 1 j to [17], wherein at least one of Y5, Y°, Y' and Y8 is N.
[19] The organic light-emitting diode (OLED) according to [18], wherein none of Y1, Y2, Y'’ and Y4 are N; and R3 is A.
[20] The organic light-emitting diode (OLED) according to [18], wherein at least one of Y1, Y2, Y3 and Y4 is N.
[21] The organic light-emitting diode (OLED) according to [20], Y4 is N.
[22] The organic light-emitting diode (OLED) according to [21], wherein Y3 is RJ-C; and R3 is A
[23] The organic light-emitting diode (OLED) according to any one of [1] to [19], wherein: none of Y1, Y2, Y3 and Y4 are N; or one of Y1, Y2, Y3 and Y4 is N; two of R1, RL R3 and R4 are independently D; other one of R1, R2, R3 and R4 is A; when none of Y3, Y2, Y3 and Y4 is N, the remaining one of R1, R2, R3 and R4 is selected from H, deuterium, substituted or unsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl; provided that when Y3 is R5-C, then R5 is H; when Y6 is R6-C, then R6 is H; when Y7 is R ~€, then R' is H; and when Y8 is R8-C, then R8 is H.
[24] The organic light-emitting diode (OLED) according to any one of [1] to [22], wherein only one of R5, Rb, R7 and R8 is D.
[25] The organic light-emitting diode (OLED) according to [24], wherein R6 is D.
[26] The organic light-emitting diode (OLED) according to [25], wherein: none of Y1, Y2, Y3 and Y4 are N; two of R1, RL R3 and R4 are independently D; other one of R1, R2, R3 and R4 is A; and the remaining one of R1, R2, R3 and R4 is selected from H, deuterium, substituted or unsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl.
[27] The organic light-emitting diode (OLED) according to any one of [1] to [22], wherein Y6 is R6-C; Y7 is R7-C; R6 and R7 are independently D: and at least one of Y\ Y2, Y3, Y4, Y5 and Y8 is N.
[28] The organic light-emitting diode (OLED) according to any one of [1] to [22], wherein Y6 is R6-C; Y' is R'-C: Rb and R7 are independently D; none ofY1, Y2, Y3, Y4, Y5, Y'6, Y7 and 8 are N; and two of R1, R2, R' and R4 are independently D and these two differ from each other.
[29] The organic light-emitting diode (OLED) according to any one of [1] to [22], wherein at least one of the following conditions is satisfied:
1) Y° is Rs-C, and R5 is A; 2) Y6 is RAC, and R6 is A;
3) Y7 is R7-C, and R / is A; and
4) Y8 is R8-C, and Rs is A.
[30] The organic light-emitting diode (OLED) according to any one of [1] to [29], wherein D is independently selected from D56 and D58; and the hydrogen atoms in D56 and D58 may be substituted by deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ammo, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaiy doxy, or silyl.
[31] The organic light-emitting diode (OLED) according to any one of [1] to [29], wherein A is independently Het-LA.
[32] The organic light-emitting diode (OLED) according to any one of [1] to [29] and [31], wherein D is independently group of Formula (lib).
[33] The organic light-emitting diode (OLED) according to any one of [1] to
[32], wherein one of R1, R2, R ' and R4 are H. [34] The organic light-emitting diode (OLED) according to any one of [1] to
[33], wherein X is O.
[35] The compound disclosed in any one of [1 ] to [34]
DETAILED DESCRIPTION The examples are provided by way of explanation of the disclosure, and not by¬ way of limitation of the disclosure. In fact, it will be apparent to those skilled in the art that various modification and variations can be made in the present disclosure without departing from the scope or spirit of the disclosure. For instance, features illustrated or described as part of one embodiment can be used on another embodiment to yield a still further embodiment. Thus, it is intended that the present disclosure cover such modifications and variations as come 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 is to be understood by one of ordinary skill in the art that the present discussion is a description of exemplary embodiments only, and is not to be construed as limiting the broader aspects of the present disclosure.
The definition of the terms appearing in the present application are shown in page 13, line 16 to page 25, line 9 of W02019/195104. The principles of OLED are shown m page 25, line 11 to page 26, line 27 of WO2G19/195104. The electronic properties and the exemplary uses of the compounds of Formula (I) are shown in page 58, line 24 to page 87, line 9 and Fig. 1 of WO2G19/195104. These descriptions and Fig. 1 of WO2019/195104 are hereby expressly incorporated by reference into the present application.
Compounds of the Disclosure
In some embodiments, the compounds have a structure of Formula (I):
Figure imgf000009_0001
C, Yt is N or R6-C, Y1 is N or R7-C, and Y8 is N or R8-C, provided that at most two of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are N, one or more of R1, R2, R3, R4, R5, R6, R' and R8 are independently D, other one or more of R1, R2, RJ, R4, R5, R6, R'’ and R8 are independently A, the other remaining R1, R2, R3, R4, R5, Rb, R' and R8 are independently selected from H, deuterium, substituted or unsubstituted alkyl, and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl, two or more of R1, R2, R3 and R4 taken together can form a ring system, two or more of R5, R6, R7 and R8 taken together can form a ring system, A is selected from CN-LA-*, PFA-La-* or Het- LA-*
PFA is perfluoroaikyl,
Het is substituted or unsubstituted heteroaiy] having at least one nitrogen atom as a ring-constituting atom,
D is group of Formula (Ila), (lib), (lie) or (lid):
Figure imgf000010_0001
(Ila) (lib) (lie) (lid)
X! is selected from N-R°’, G and S;
RD is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ammo, substituted or unsubstituted and, substituted or unsubstituted aryioxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; two or more instances of RD taken together can form a ring system;
R0’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted ammo, substituted or unsubstituted and, and substituted or unsubstituted heteroaryl; two or more instances of
Figure imgf000010_0002
and RD taken together can form a ring system;
LD and LA are independently selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroaiylene; wherein each instance of arylene and heteroaiylene can he substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaiyl; two or more of these substituents taken together can form a ring system;
C~RD of the benzene rings in Formulae (Ila), (lib), (Tic) and (lid) may be substituted with N; and each represents a point of attachment to Formula (I).
In some embodiments, alkyl is CI-C20-alkyl. In some embodiments, alkyl is Cl- C12 alkyl. In some embodiments, alkyl is C1-C6 alkyl in some embodiments, alkyl is C1-C3 alkyl. In some embodiments, aryl is C6-C40 aryl. In some embodiments, aryl is C6-C25 and. In some embodiments, an is C6-C14 aryl in some embodiments, aryl is C6-C10 aryl. In some embodiments, heteroaryl is C2-C40 heteroaryl. In some embodiments, heteroaryl has 5-40 ring-constituting atoms. In some embodiments, heteroaryl has 5-25 ring-constituting atoms. In some embodiments, heteroaryl has 5-10 ring-constituting atoms. In some embodiments, alkoxy is C1-C20 aikoxy. In some embodiments, alkoxy is Cl-Cl 2 alkoxy. In some embodiments, alkoxy is C1-C6 alkoxy. In some embodiments, alkoxy is C1-C3 alkoxy. In some embodiments, aryloxy is C6~ C40 aryloxy. In some embodiments, aryloxy is C6-C25 aryloxy. In some embodiments, aiyioxy is C6-C14 aryloxy. In some embodiments, aryloxy is C6-C10 aryloxy. In some embodiments, heteroaryloxy is C3-C40 heteroaryl oxy. In some embodiments, heteroaiyloxy has 5-40 ring-constituting atoms. In some embodiments, heteroaryloxy has 5-25 ring-constituting atoms. In some embodiments, heteroaryloxy has 5-10 ring- constituting atoms. In some embodiments, arylene is C6-C40 arylene. In some embodiments, arylene is C6-C25 arylene. In some embodiments, arylene is C6-C14 arylene. In some embodiments, arylene is C6-C10 arylene. In some embodiments, heteroarylene is C2-C40 heteroarylene. In some embodiments, heteroarylene has 5-40 ring-constituting atoms. In some embodiments, heteroarylene has 5-25 ring-constituting atoms in some embodiments, heteroarylene has 5-10 ring-constituting atoms.
In some embodiments, X in Formula (I) is O. In some embodiments, X in Formula (I) is S.
Y1 is N or R!-C. Y2 iS N or R2~C, Y3 is N or R3-C, Y4 is N or R4-C, Y5 is N or R5- C, YtJ is N or R6-C, Y' is N or R7-C, and Y8 is N or R8-C, provided that at most two of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are N,
In some embodiments, Y1 is R'-C. In some embodiments, Y2 is R2-C. In some embodiments, Y3 is R5-C. In some embodiments, Y4 is R4-C. In some embodiments, Y5 is R3-C. In some embodiments, YtJ is R6-C. In some embodiments, Y7 is R'-C. in some embodiments, Y8 is R8~C. In some embodiments,
Figure imgf000011_0001
is N. in some embodiments, Y2 is N. In some embodiments, Y3 is N. In some embodiments, Y4 is N. In some embodiments, Y’ is N. In some embodiments, Y6 is N. In some embodiments, Y7 is N. In some embodiments, Y8 is N. In some embodiments, Y1 is R'-C, Y2 is R2-C, Y' is R'-C, and Y4 is R4-C. In some embodiments, Y1 is N, Y2 is R -C, Y3 is R3~C, and Y4 is R4-C. in some embodiments, Y5 is R5-C. In some embodiments, Y6 is R°-C. In some embodiments, Y? is R7-C. In some embodiments, Y8 is R8-C.
In some embodiments, Y1 is N, Y2 is R -C, Y3 is R3-C, and Y4 is R4-C. In some embodiments, Y1 is Rl-C, Y2 is N, Y is R -C, and Y4 is R4-C. In some embodiments, Y1 is R3-C, Y2 is R2-C, Y3 is N, and Y4 is R4-C. In some embodiments, Y1 is R!-C, Y2 is R2- C, Y3 is R3-C, and Y4 is N. in some embodiments, Y1 is N, Y2 is N, Y3 is R3~C, and Y4 is R4-C. In some embodiments, Y! is N, Y2 is R -C, Y' is N, and Y'4 is R4-C. In some embodiments, Y1 is N, Y2 is R2-C, Y' is R3-C, and Y4 is N. In some embodiments, Y1 is
R3-C, Y2 is N, Y3 is N, and Y4 is R4~C. In some embodiments, Y1 is R1-C, Y2 is N, Y3 is R3~C, and Y4 is N In some embodiments, Y1 is Rt-C, Y2 is R2~C, Y3 is N, and Y4 is N. In some embodiments, Y3 is N, Y6 is R6-C, Y7 is R'-C, and Y8 is R*-C. In some embodiments, Y5 is Rs-C, Yb is N, Y7 is R7-C, and Ys is Rs-C. In some embodiments, Y3 is Rs-C, Y6 is R6-C, Y1 is N, and Y8 is Rs-C In some embodiments, Y3 is R3-C, Y6 is R6-
C, Y7 is R7-C, and Y8 is N. In some embodiments, Y3 is N, Y6 is N, Y' is R'-C, and Y8 is R8-C. in some embodiments, Y3 is N, Yb is R6-C, Y7 is N, and Y8 is Rs-C. In some embodiments, Y5 is N, Y6 is R6-C, Y' is R7-C, and Y8 is N. In some embodiments, Y5 is R5~C, Y6 is N, Y7 is N, and Y8 is R8~C. In some embodiments, Y5 is R5-C, Y6 is N, Y7 is R7-C, and Y8 is N. In some embodiments, Y'5 is R3-C, Y6 is R6-C, Y' is N, and Y8 is N.
In some embodiments, none of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are N. in some embodiments, one of Y1, Y , Y3, Y4, Y5, Y6, Y'' and Y8 is N. In some embodiments, one of Y5, Y'2, Y3 and Y4 is N, and none of Y3, Y6, Y7 and Y8 are N. In some embodiments, none of Y1, Y2, Y and Y4 are N, and one of Y5, Yb, Y7 and Y8 is N. In some embodiments, two of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are N. in some embodiments, one of Y1, Y2, Y3 and Y4 is N, and one of Y3, Y6, Y; and Y8 is N. In some embodiments, two of Y1, Y2, Y3 and Y4 are N, and none of Y5, Y6, Y7 and Y8 are N. In some embodiments, none of Y1, Y2, Y3 and Y4 are N, and two of Y5, Y6, Y' and Y8 are N. In Formula (I), one or more of R\ R2, R3, R4, R5, Rb, R7 and R8 are independently D. In some embodiments, R’ is D. In some embodiments, R2 is D. In some embodiments, R3 is D. In some embodiments, R4 is D. In some embodiments, R5 is D. In some embodiments, R13 is
D. In some embodiments, R' is D. In some embodiments, R8 is D. in some embodiments, only one of R1, R2, R3, R4, R5, R6, R' and R8 is D. In some embodiments, at least two of R1, R2, R3, R4, R3, R', R7 and R8 are D. In some embodiments, at least three of R1, R2, R3, R4, R5, R6, R7 and R8 are D. In some embodiments, at least four of R1, R2, R3, R4, R5, R6,
R' and R8 are D. In some embodiments, at most six of R1, R2, R3, R4, R5, Rb, R' and R8 are D In some embodiments, at least one of R1, Rz, R3 and R4 is D. In some embodiments, only one of R1, R2, R3 and R4 is D. In some embodiments, two of R1, R2, R3 and R4 are D. In some embodiments, three of R1, R2, R3 and R4 are D. In some
H embodiments, all of R5, R2, R and R4 are D. In some embodiments, two or three of Rf , R2, R3 and R4 are D. in some embodiments, at least one of R5, R6, R7 and R* is D. In some embodiments, only one of R5, R6, R7 and R8 is D. in some embodiments, two of R5, R6, R7 and R8 are D. In some embodiments, three of R', R6, R7 and R8 are D. In some embodiments, all of R5, Rb, R' and R8 are D. In some embodiments, two or three of R3,
R6, R7 and R8 are D. In some embodiments, at least one of R1, R2, R ' and R4 is D, and at least one of R5, R°, R' and R8 is D. In some embodiments, at least two of R1, R2, R3 and R4 are D, and at least one of R5, R6, R7 and R8 is D. In some embodiments, at least one of R1, R2, R3 and R4 is B, and at least two of R5, R6, R' and R8 are D. In some embodiments, at least two of R1, R2, RJ and R4 are D, and at least two of Rf R6, R'' and R8 are D In some embodiments, at least three of R1, R2, R3 and R4 are D, and at least two of R:1, R°, R7 and R8 are D. In some embodiments, R1 and R2 are D. In some embodiments, R! and R3 are D. In some embodiments, R1 and R4 are D. In some embodiments, R2 and R3 are D. In some embodiments, R2 and R4 are D. In some embodiments, R3 and R4 are D In some embodiments, R1, R2 and R3 are D. In some embodiments, R4, R2 and R4 are D. In some embodiments, R1, R3 and R4 are D. In some embodiments, R2, R3 and R4 are D. In some embodiments, R5 and R6 are D. In some embodiments, R5 and R ' are D. In some embodiments, R5 and R8 are D. In some embodiments, R6 and R7 are D. In some embodiments, R6 and R8 are D. In some embodiments, R7 and R8 are D. In some embodiments, R3, R6 and R' are D. In some embodiments, R5, R6 and R8 are D. In some embodiments, R5, R'’ and R8 are D. In some embodiments, R°, R ' and R8 are D. In some embodiments, all instances of D are the same. In some embodiments, all instances of D are different.
In Formula (I), one or more of R4, R2, R3, R4, R3, R6, R7 and R8 are independently A. In some embodiments, R4 is A. In some embodiments, R2 is A. In some embodiments,
R3 is A. In some embodiments, R4 is A. In some embodiments, R3 is A. In some embodiments, R6 is A. In some embodiments, R' is A. In some embodiments, R8 is A. In some embodiments, only one of R1, R2, R3, R4, R5, R6, R'’ and R5 is A In some embodiments, at least two of R1, R2, R3, R4, R3, R6, R' and R8 are A. In some embodiments, at least three of R1, R2, R3, R4, R5, R6, R7 and R8 are A. In some embodiments, at least four of R1, R2, R3, R4, R5, R6, R7 and R8 are A. In some embodiments, at most six of R4, R2, R3, R4, R\ R6, R and R5 are A. In some embodiments, at least one of R1, R2, R3 and R4 is A. In some embodiments, only one of R1, R2, R3 and R4 is A. In some embodiments, two of R1, R2, R3 and R4 are A. In some embodiments, three of R3, R2, R3 and R4 are A. In some embodiments, ail of R1, R2, R3 and R4 are A. in some embodiments, two or three of R1, R2, R3 and R4 are A. In some embodiments, at least one of R5, R6, R' and R8 is A. In some embodiments, only one of R5, R6, R7 and R8 is A. In some embodiments, two of R5, R6, R7 and R8 are A. in some embodiments, three of R5, Rb, R' and R8 are A. In some embodiments, ail of R5, R6, R7 and R8 are A. In some embodiments, two or three of R5, R°, R7 and R8 are A. In some embodiments, at least one of R3, Rz, R3 and R4 is A, and at least one of R5, R6, R? and R8 is A. In some embodiments, at least two of R3, R2, R3 and R4 are A, and at least one of R’, R6, R' and R8 is A. In some embodiments, at least one of R3, R2, R3 and R4 is A, and at least two of R5, R°, R' and R8 are A. In some embodiments, at least two of R1, R2, R3 and R4 are A, and at least two of R5, R6, R/' and R8 are A. In some embodiments, at least three of R1, R2, R3 and R4 are A, and at least two of R5, Rb, R7 and Rs are A. In some embodiments, R1 and R2 are A. In some embodiments, R1 and RJ are A. In some embodiments, R1 and R4 are A. In some embodiments, R2 and RJ are A. In some embodiments, R2 and R4 are A. In some embodiments, R3 and R4 are A. In some embodiments, R1, R2 and R3 are A. In some embodiments, R1, R2 and R4 are A. In some embodiments, R1, RJ and R4 are A. In some embodiments, R2, R3 and R4 are A. In some embodiments, R5 and R6 are A. In some embodiments, R5 and R7 are A. In some embodiments, R5 and R8 are A. In some embodiments, R6 and R' are A. In some embodiments, R6 and R8 are A. In some embodiments, R7 and R8 are A. In some embodiments, R5, R6 and R? are A. In some embodiments, R3, R° and R8 are A. In some embodiments, R5, R7 and R8 are A. In some embodiments, R°, R' and R8 are A. In some embodiments, all instances of A are the same. In some embodiments, ail instances of A are different. In Formula (I), one or more of R3, R2, R3, R4, R5, R6, R7 and R8 are independently
D; other one or more of R3, R2, R3, R4, R3, R6, R7 and R8 are independently A; and the other remaining R1, R2, R3, R4, R5, Rb, R' and R8 are independently selected from H, deuterium, substituted or unsubstituted alkyl, and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl in some embodiments, all of the other remaining R3, R , RJ, R4, R5, R°, R' and R8 are H. in some embodiments, at least one of the other remaining R1, R2, RJ, R4, R5, R6, R? and R8 is alkyl that can be substituted with one or more substituents independently selected from deuterium and aryl. In some embodiments, at least one of the other remaining R1, R2, R3, R4, R3, Rb, R' and R8 is and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl in some embodiments, all of the other remaining R1, R2, R3, R4, R5, R6, R ' and R8 are independently selected from H, deuterium and aryl that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl in some embodiments, all of the oilier remaining R1, R2, R3, R4, R5, R°, R' and R8 are independently selected from H, deuterium and unsubstituted phenyl. In some embodiments, at least one of the other remaining R1, R2, R3, R4, R5, R6, R' and R8 is unsubstituted phenyl. in some embodiments, all of the other remaining R1, R2, R3 and R4 are H. In some embodiments, all of the other remaining R1, R2, R3 and R4 are independently selected from deuterium; alkyl that can be substituted with one or more substituents independently selected from deuterium and aryl; and and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl. In some embodiments, all of the other remaining R1. R2, R3 and R4 are aryl that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl. In some embodiments, all of the other remaining R1, R2, R3 and R4 are unsubstituted phenyl. In some embodiments, all of the other remaining R5, Rb, R' and R8 are H. In some embodiments, at least one of the other remaining R5, R6, R7 and R8 are independently selected from deuterium; alkyl that can be substituted with one or more substituents independently selected from deuterium and aryl: and and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl. In some embodiments, at least one of the other remaining R5, R6, R7 and R8 is and that can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl. In some embodiments, at least one of the other remaining R5, R6, R' and R8 is unsubstituted phenyl. In some embodiments, at least one of the other remaining R1, R2,
R5 and R4 is unsubstituted phenyl, and at least one of the other remaining R3, R6, R7 and R8 is unsubstituted phenyl. In some embodiments, all instances of alkyl that that can be substituted with one or more substituents independently selected from deuterium and aryl is selected from methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl and n-butyl. in Formula (I), two or more of R!, R2, R3 and R4 taken together can form a ring system, and two or more of R5, R6, R' and R8 taken together can form a ring system. In some embodiments, the ring system here is substituted or unsubstituted aromatic ring. In some embodiments, the ring system here is substituted or unsubstituted aliphatic ring. In some embodiments, none of R1, R2, R3 and R4 are taken together to form a ring system, and none of R5, R6, R7 and R8 are taken together to form a ring system. In some embodiments, R4 and R5 are not taken together to form a ring system.
In Formula (I), A is selected from CN-LA-*, PFA-L4-* or Het- L4-*. Each represents a point of attachment to Formula (I). PFA is perfluoroalkyl. In some embodiments, PFA is perfluoroalkyl having 1 to 10 carbon atoms. In some embodiments, PFA is perfluoroalkyl having 1 to 3 carbon atoms in some embodiments, PFA is trifluoromethyl. Het is substituted or unsubstituted heteroaryl having at least one nitrogen atom as a ring-constituting atom. L4 is independently selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene; wherein each instance of arylene and heteroarylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; and two or more of these substituents taken together can form a ring system.
In some embodiments. CN-L4- is substituted or unsubstituted 4-cyanoplienyi, substituted or unsubstituted 3-eyanophenyl, substituted or unsubstituted 2-cyanophenyI, or substituted or unsubstituted 3,5-dicyanophenyl. In some embodiments, CN-LA- is unsubstituted 4-cyanopheny], unsubstituted 3-cyanophenyl, unsubstituted 2-cyanophenyl, or unsubstituted 3,5-dicyanophenyI.
In some embodiments,
Figure imgf000016_0001
some embodiments, Het-LA~
Figure imgf000016_0002
. , , , . bond or substituent.
In some embodiments, R2i, R22, R23, R24 and R25 are independently H, CN, substituted or unsubstituted alkyl, substituted or unsubstituted ary], or substituted or unsubstituted heteroaryl. Each instance of alkyl can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted and, and substituted or unsubstituted heteroaryl. Each instance of aryl and heteroaryl can 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 these substituents taken together can form a ring system. In some embodiments, the ring system here is substituted or unsubstituted aromatic ring, or substituted or unsubstituted aliphatic ring.
In some embodiments, LA and Lu are independently selected from single bond, substituted or unsubstituted aiyiene, and substituted or unsubstituted heteroaiyiene. in some embodiments, LA and L11 has two or three substituted or unsubstituted arylenes bonded together. In some embodiments, LA and L11 consists of only one substituted or unsubstituted arylene. in some embodiments, LA and L11 has two or three substituted or unsubstituted heteroaryienes bonded together. In some embodiments, LA and L11 consists of only one substituted or unsubstituted heteroaiyiene. In some embodiments, each instance of aiyiene and heteroaiyiene is unsubstituted or substituted with one or more substituents independently selected from deuterium, halogen, cyano, alkyl, and, heteroaryl and combinations of two or more of them; and two or more of these substituents taken together can form a ring system in some embodiments, the ring system here is substituted or unsubstituted aromatic ring, or substituted or unsubstituted aliphatic ring in some embodiments, LA and L11 are single bond, unsubstituted phenylene, or phenylene substituted with at least one alkyl. In some embodiments, LA and L11 are single bond. In some embodiments, LA and Lu are substituted or unsubstituted aiyiene, or substituted or unsubstituted heteroarylene.
In some embodiments, A is selected from the group consisting of A1 to A16 shown below. In some embodiments, Het is selected from the group consisting of A2, A3, A4, A5, A6, A10, All, A12, A15 and A16. in All), All, A12, R is independently hydrogen or unsubstituted phenyl. In preferred embodiments, A is selected from the group consisting of Ai, A2, A15 and A16.
Figure imgf000017_0001
A1 A2 A3 A4
Figure imgf000018_0001
(11a) (lib) (He) (lid)
Each represents a point of attachment to Formula (1).
In some embodiments, X' is RD'-N. In some embodiments. X' is O. In some embodiments, X' is S.
In some embodiments, LD is independently selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroaryiene; wherein each instance of arylene and heteroaryiene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; and two or more of these substituents taken together can form a ring system. In some embodiments, LD is substituted or unsubstituted arylene. In some embodiments, I.D is substituted or unsubstituted heteroaryiene.
In some embodiments, R° are hydrogen. In some embodiments, RD are deuterium. In preferred embodiments, at least one of R° is not hydrogen atom. In preferred embodiments, at least one of R° is substituted or unsubstituted alkyl, substituted or unsubstituted afkoxy, substituted or unsubstituted ammo, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted beteroaryloxy, or silyl. In more preferred embodiments, at least one of RD is substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, or substituted or unsubstituted heieroaryloxy . In still more preferred embodiments, at least one of RD is substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. In some embodiments, R° are independently hydrogen or substituted or unsubstituted alkyl. In some embodiments, R° are independently hydrogen or substituted or unsubstituted alkoxy. In some embodiments, RD are independently hydrogen or substituted or unsubstituted amino. In some embodiments, RD are independently hydrogen or substituted or unsubstituted aryl. In some embodiments, R° are independently hydrogen or substituted or unsubstituted aryloxy. In some embodiments, R° are independently hydrogen or substituted or unsubstituted heteroaryl. In some embodiments, R° are independently hydrogen or substituted or unsubstituted heieroaryloxy. In some embodiments, RD are independently hydrogen or silyl. In some embodiments, two or more instances of R° are taken together to form a ring system.
In some embodiments of Formula (Ila), RD at 3-position of the diphenylamino is substituted and the other RD are hydrogen. In some embodiments of Formula (11a), R° at 3- and 3'-positions of the diphenylamino are substituted and the other R° are hydrogen. In some embodiments of Formula (ila), R° at I -position of the diphenylamino and R° at 2-position of the diphenylamino are taken together to form a ring system in some embodiments of Formula (Ila), RD at 2-position of the diphenylamino and RD at 3- position of the diphenylamino are taken together to form a ring system. In some embodiments of Formula (Ila), R° at 3-position of the diphenylamino and RD at 4- position of the dipheny lamino are taken together to form a ring system.
In some embodiments of Formulae (lib) and (lie), RD at 3-position of the carbazole ring is substituted and the other R° are hydrogen. In some embodiments of Formulae (lib) and (lie), RD at 3- and 6-positions of the carbazole ring are substituted and the other R° are hydrogen. In some embodiments of Formulae (lib) and (lie), R° at 1 -position of the carbazole ring and RD at 2-position of the carbazole ring are taken together to form a ring system. In some embodiments of Formulae (ttb) and (lie), RD at
2-position of the carbazole ring and R° at 3-position of the carbazole ring are taken together to form a ring system. In some embodiments of Formulae (lib) and (lie), R° at 3-position of the carbazole ring and R° at 4-position of the carbazole ring are taken together to form a ring s tem.
In some embodiments of Formula (Tic), L° bonds to 5-position of the carbazole ring in some embodiments of Formula (lie), L° bonds to 6-position of the carbazole ring. In some embodiments of Formula (lie), LD bonds to 7-position of the carbazole ring. In some embodiments of Formula (lie), L° bonds to 8-position of the carbazole ring.
In some embodiments of Formula (lid), RD at 2-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid), RD at
3-position of the indole ring is substituted and the other R° are hydrogen. In some embodiments of Formula (lid),
Figure imgf000020_0001
at 2- and 3-positions of the indole ring are substituted and the other R° are hydrogen. In some embodiments of Formula (II d), R° at 2-position of the indole ring and R° at 3-position of the indole ring are taken together to form a ring system. In some embodiments of Formula (lid), RD at 3-position of the indole ring and RD at 4-position of the indole ring are taken together to form a ring system.
Figure imgf000020_0002
In some embodiments, R°’ is hydrogen. In some embodiments, R° is deuterium. In some embodiments, RD is substituted or unsubstituted alkyl. In some embodiments, RD is substituted or unsubstituted amino. In some embodiments, R° is substituted or unsubstituted aryl. In some embodiments, R° is substituted or unsubstituted heteroaryl. In some embodiments, two or more instances of RD and R° taken together can form a ring system.
In some embodiments, L° is a single bond. In some embodiments, LD is substituted or unsubstituted arylene, or substituted or unsubstituted heteroaiylene. In some embodiments, L° is substituted or unsubstituted aiyiene. In some embodiments, I,D is substituted or unsubstituted heteroarylene.
C-RD of the benzene rings in Formulae (Iia), (lib) (tie) and (lid) may be substituted with N. In some embodiments, only one of C-RD of the benzene ring is substituted. Each in Formulae (Iia), (lib), (lie) and (lid) represents a point of attachment to Formula (I). in some embodiments, D is selected from the group consisting of D1 to D97 shown below.
Figure imgf000021_0001
Figure imgf000023_0001
D66 D67 D88 D69 D70
Figure imgf000024_0001
Figure imgf000025_0001
In preferred embodiments, D is selected from the group consisting of DI, D4, D21, F76, D86, D94, D96 and D97. In some embodiments, L11, LA and LD are selected from the group consisting of
Ml to M22 shown below.
Figure imgf000025_0002
Figure imgf000026_0001
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 1") satisfying that Y1 is R!-C, Y2 is R?-C, Y3 is R3-C, Y4 IS R4-C, Y5 IS R5-C, Y6 is R6-C, Y7 is R7-C, and Y8 is R8-C; R5, R6, R7 and R8 are H; at least one of R1, R2, R3 and R4 is D; at least one of R1, R2, RJ and R4 is
A.
In some embodiments of Group 1, two of R1, R2, R3 and R4 are D. In some embodiments of Group 1, two of R1, R2, R3 and R4 are D; one of R1, R2, R3 and R4 is A; and the remaining one is H In some embodiments, two of R1, R2, RJ and R4 are D; one of R1, R2, R3 and R4 is A; and the remaining one is substituted or unsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl. In some embodiments, two D's are the same. In some embodiments, two D's are different from each other. In some embodiments of Group 1, R1 is A, two of R2, R3 and R4 are D, and the remaining one is H. in some embodiments, R2 is A, two of R1, R3 and R4 are D, and the remaining one is H. In some embodiments, R3 is A, two of Rf , R2 and R4 are D, and the remaining one is H. In some embodiments, R4 is A, two of R1, R2 and R are D, and the remaining one is H. In some embodiments, R1 is A, R is H, and R3 and R4 are D wherein two D's are the same. In some embodiments, R1 is A, R2 is H, and R3 and R4 are D wherein two D's are different from each other.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 2") satisfying that Y1 is Rf-C, Y2 is R2-C, Y3 IS R3-C, Y4 IS R4-C, Y5 is R5-C, Y6 is R! -il Y7 is R -C. and Y8 is R8-C; at least one of R1, R2, f and R4 is D; and at least one of R5, R6, R7 and Rs is D.
In some embodiments of Group 2, two of R1, R2, R ' and R4 are D, and one of R5, R6, R7 and R8 is D. in some embodiments, one of R1, R2, R and R4 are D, and one of R5, R6, R7 and R8 is D. in some embodiments, two of R4, R2, R3 and R4 are D; one of R1, R2, R3 and R4 is A; the remaining one of R1, R2, R3 and R4 is H; one of R5, R6, R' and R8 is D; and the remaining three of R5, R6, R7 and R8 are H. In some embodiments, two of R3, R2, R3 and R4 are D; one of R1, R2, R3 and R4 is A; the remaining one of R1, R2, R3 and
R4 is H; one of R5, R6, R' and R8 is D; one of R5, R°, R' and R8 is A; and the remaining two of R5, R6, R7 and R8 are H. In some embodiments, two or more D's are the same. In some embodiments, two or more D's are different from each other.
In some embodiments of Group 2, R1 is A, R2 is H, R3 and R4 are B wherein two D's are the same; R6 is D; and R5, R; and R8 are H. In some embodiments, R1 is A, R2 is H, R3 and R4 are D wherein two D's are different from each other; R° is D; and R3, R7 and R8 are H. In some embodiments, R1 is A, R2 is H, R3 and R4 are D wherein two D's are the same; R7 is D; and R5, R6 and R8 are H. In some embodiments, R1 is A, R2 is H, R3 and R4 are D wherein two D's are different from each other; R; is D; and R5, R6 and R8 are H. in some embodiments, R5 is A, R4 is H, R2 and R3 are D wherein two D's are the same; R is D; and R5, R6 and R8 are H. In some embodiments, R1 is A, R4 is H, R2 and R3 are D wherein two D's are different from each other; R; is D; and R5, Rb and R8 are H. in some embodiments, Rf is A, R2 is H, R3 and R4 are D wherein two D's are the same; R6 is A; R is D; and R5 and R8 are H. In some embodiments, R1 is A, R2 is H, R3 and R4 are D wherein two D's are different from each other; R6 is A; R7 is D; and R5 and
R8 are H. In some embodiments, R3 is A, R2 is H, R3 and R4 are D wherein two D's are the same; R6 is D; and R3, R7 and R8 are H. In some embodiments, 1 is A, R2 is H, R3 and R4 are D wherein two D's are different from each other; R6 is D; and R5, R7 and R8 are H. In some embodiments, R1 is A, R2 is H, R3 and R4 are D wherein two D's are the same; R6 is A; R7 is D; and R5 and R8 are H. In some embodiments, R1 is A, R2 is H, R3 and R4 are D wherein two D's are different from each other; R6 is A; R7 is D; and R5 and R8 are H.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 3”) satisfying that one of Y1, Y2, Y3 and Y4 is N, Y5 is R5-C, Y6 is R6-C, Y7 is R7-C, Y8 is Rs-C; at least one of R1, R2, R3 and R4 is D; none of R3, Rb, R7 and R8 is D.
In some embodiments of Group 3, two of Rl R2, R3 and R4 are D, and one of Rl R2, R3 and R4 is A; and R5, R6, R7 and R8 are H. In some embodiments, Y3 is R3-C, Y2 is N, Y3 is R3-C, Y4 is R4-C. In some embodiments, Y3 is R3-C, Y2 is R2-C, Y3 is N, Y4 is R4-C. in some embodiments, R’ is A, Y2 is N, R3 and R4 are D wherein two D's are the same; and R5, Rb, R7 and R8 are H. in some embodiments, R1 is A, Y2 is N, R3 and R4 are D wherein two D's are different from each other; and R5, R6, R7 and R8 are H.
In some preferred embodiments, the compound of Formula (i) is selected from the group (which is hereinafter referred to as "Group 4") satisfying that Y1 is R1 -C. Y2 is R2-C, Y3 is R3-C, Y4 is R4-C, one of Y3, Y6, Y1 and Y8 is N; at least one of R1 Rz, R3 and R4 is D; none of R5, R6, R; and R8 is D
In some embodiments of Group 4, two of R1, R2, R3 and R4 are D, and one of R1, R2, R3 and R4 is A; and R5, Rb, R and R8 are H. In some embodiments, Y5 is N, Y6 is R6-C, Y7 is R?-C, Y8 is R8-C. In some embodiments, Y5 is Rs-C, Y6 is R6~C, Y' is R/-C,
Y8 is N In some embodiments, R1 and R2 are D wherein two D's are the same, R3 is A, R4 is H, Y5 is N, Y6 is R6-C, Y7 is R7-C, Y8 is Rs-C, and R6, R7 and R8 are H. In some embodiments, R1 and R2 are D wherein two D's are different from each other, R5 is A, R4 is H, Y5 is N, Y6 is R'-C. Y7 is R7-C, Y8 is Rs-C, and R6, R7 and R8 are H. In some embodiments, Rf and R2 are D wherein two D's are the same, R3 is A, R4 is H, Y5 is R3-C,
Yb is R6-C, Y7 is R7-C, Y8 IS N, and R5, R6 and R are H. In some embodiments, R1 and R2 are D wherein two D's are different from each other, RJ is A, R4 is H, Y5 is R5-C, Y6 is R6-C, Y7 is R7-C, Y8 is N, and R5, R6 and R7 are H.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 5") satisfying that one of Y1, Y2, Y3 and Y4 is N, Y5 is R5-C, Y6 is R'-C. Y7 is R7-C, Y8 is RS~C; at least one of R1, R \ R3 and R4 is D; at least one of Rl R'l R7 and R8 is D.
In some embodiments of Group 5, two of R1, R2, R3 and R4 are D, and one of R1, R2, R ' and R4 is A; one of R5, R6, R7 and R8 is D; and the remaining three of R5, Rb, R7 and R8 are H In some embodiments, Y1 is Rf-C, Y2 is N, Y3 is R3-C, Y4 is R4-C. In some embodiments, Y1 is Rl-C, Y2 is R -C, Y3 is N, Y4 is R4-C. In some embodiments, R1 is A, Y2 is N RJ and R4 are D wherein two D's are the same. In some embodiments, R1 is A, Yz is N, RJ and R4 are D wherein two D's are different from each other. In some embodiments, R6 is D, and R5, R7 and R8 are H. In some embodiments, R7 is D, and R5, Rb and R8 are H.
In some embodiments of Group 5, R1 is A, Y2 is N, RJ and R4 are D wherein two D's are the same, R7 is D, and R3, R° and R8 are H. In some embodiments R! is A, Y2 is N, R3 and R4 are D wherein two D's are different from each other, R7 is D, and R5, R6 and R8 are H. In some embodiments, R1 is A, Y2 is N, R3 and R4 are D wherein two D's are the same, R° is D, and R5, R7 and R8 are H. in some embodiments R1 is A, Y2 is N, R3 and R4 are D wherein two D's are different from each other, R6 is D, and R5, R7 and R8 are H. In some embodiments of Group 5, R1 is A, Y2 is N, R3 and R4 are D wherein two D's are the same, R6 is A, R7 is D, and R5 and R8 are H. in some embodiments Rf is A, Y2 is N, R3 and R4 are D wherein two D's are different from each other, R6 is A, R' is D, and R3 and R8 are H. in some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 6") satisfying that Y1 is Rf-C, Y'2 is R2-C, Y3 IS R3-C, Y4 is R4-C, one of Y5, Y6, Y7 and Y8 is N; at least one of R!, R2, R3 and R4 is D; at least one of R5, R6, R' and R8 is D.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 7") satisfying that one of Y1, Y2, Y3 and Y4 is N; one of Y5, Y6, Y7 and Y8 is N; at least one of R1, R2, R3 and R4 is D; none of R5, R6, R' and R8 is D In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 8") satisfying that one of Y1, Y2, Y3 and Y4 is N; one of Y5, Y6, Y' and Y8 is N; at least one of R1, R2, R5 and R4 is D; at least one of R5, R6, R7 and R8 is D.
Groups 1 to 8 are preferred in this order. Group 1 is the most preferred group and Group 2 is the second most preferred group.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 9") satisfying that at least one of Y3, Y'·. Y7 and Y8 is N. In some embodiments of Group 9, at least two of R1, R2, R3 and R4 are D or A. In some embodiments, none of R3, R°, R' and R8 are D, and none of R3, R6, R7 and R8 are A. In some embodiments, the number of D and A in R1, R2, R3 and R4 is not smaller than the number of D and A in R5, R6, R? and R8.
In some embodiments of Group 9, at least one of Y1, Y2, Y3 and Y4 is N. In some embodiments, Y4 is N. In some embodiments, Y4 is N; Y3 is R3-C; and R3 is A.
In some embodiments of Group 9, Y3 is RJ-C; and R3 is A. in some embodiments of Group 9, Y3 is R3-C; R3 is A; and none of Y1, Y2, Y3 and Y4 are N.
In some embodiments of Group 9, only one of Y3, Y6, Y! and Y8 is N. In some embodiments, Y5 is N. In some embodiments, Yb is N. In some embodiments, Y7 is N. in some embodiments, Y8 is N. In some embodiments, one of Y5, Yb, Y7 and Y8 is N; none of R5, R6, R7 and R8 are D; and none of R5, R6, R7 and R8 are A. In some embodiments, one ofY5, Y°, Y7 and Y8 is N; at least two of R1, R2, R3 and R4 are D: and at least one of R1, R2, R3 and R4 is A. In some embodiments, one of Y5, Y°, Y ' and Y8 is N; two of IV. R2, R3 and R4 are D: other one of R1, R2, R3 and R4 is A; and the other one of R1, R2, R3 and R4 is H or unsubstituted phenyl. In some embodiments, one of Y5, Y' and Y8 is N; Y6 is R°-C; R° is D; at least two of R1, R2, R3 and R4 are D: and at least one of R1, R2, R3 and R4 is A. In some embodiments, one of Y3, Y7 and Y'8 is N: Y6 is R6-C; Rb is B; two of R1, R2, R3 and R4 are D: other one of R1, R2, R3 and R4 is A; and the other one of R1, R2, R3 and R4 is H or unsubstituted phenyl. In some embodiments, one of Y \ Y6, Y' and Y8 is N; one of R5, R6, R7 and R8 is D. In some embodiments, one of Y3, Y7 and Y8 is N; Y6 is Rb-C; and Rf is D. In some embodiments, Y4 and Y3 are N; Y6 is R6- C; and R6 is D. In some embodiments, Y4 and Y' are N; Y6 is Rb-C; and Rb is D. In some embodiments, Y4 and Y8 are N; Yb is R°-C; and R° is D. In some embodiments, Y4 and Y3 are N; Y6 is R6-C; R6 is D; at least two of R5, R2, R3 and R4 are D: and at least one of R!, R2, R3 and R4 is A. in some embodiments, Y4 and Y7 are N; Y6 is R6-C; Rb is D; at least two of R1, R2, R3 and R4 are D: and at least one of R1, R2, R3 and R4 is A. In some embodiments, Y'4 and Y8 are N; Y6 is R6-C; R6 is D; at least two of R5, R2, R3 and R4 are D: and at least one of R1, R2, R3 and R4 is A. In some embodiments, one of Y5, Y6 and Y8 is N; Y7 is R7-C; R7 is B; at least two of R1, R2, R3 and R4 are D: and at least one of R1, R2, R3 and R4 is A. In some embodiments, one of Y5, Y6 and Y8 is N; Y7 is R?-C; R7 is D: two of R3, R2, R3 and R4 are B: other one of R1, R2, R3 and R4 is A; and the other one of R1, R2, R3 and R4 is H or unsubstituted phenyl. In some embodiments, one of Y5, Y6 and Y8 is N; Y' is R'-C; and R'' is D. In some embodiments, Y4 and Y5 are N; Y7 is R7-C; and R7 is D. In some embodiments, Y4 and Y6 are N; Y' is R'-C; and R7 is D. In some embodiments, Y4 and Y8 are N; Y7 is R7-C; and R7 is D. in some embodiments, Y'4 and Y5 are N; Y'' is R'-C; R7 is D; at least two of R1, R2, R3 and R4 are B: and at least one of R1, R2, R3 and R4 is A. In some embodiments, Y4 and Y6 are N; Y ' is R'~C; R; is D; at least two of Rf , R2, R3 and R4 are B: and at least one of R1, R2, R3 and R4 is A. In some embodiments, Y4 and Y8 are N; Y' is R'-C; R' is D; at least two of R1, R2, R3 and
R4 are D: and at least one of R1, R2, R3 and R4 is A. in some embodiments, Y3 is N; Y6 is R’-C: Y7 is R -C; and R6 and R7 are D.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 10") satisfying the following conditions: none of Y1, Y2, Y3 and Y4 are N; or one ofY1, Y2, Y3 and Y4 is N; two of R1, R2, RJ and R4 are independently D; other one of R1, R2, R3 and R4 is A: when none of Y1, Y2, Y3 and Y4 are N, the remaining one of R1, R2, R3 and R4 is selected from H. deuterium, substituted or imsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl; provided that when Y5 is R'-C, then R5 is H; when Y° is R°-C, then R6 is H; when
Y7 is R7-C, then R7 is H; and when Y8 is RS~C, then R8 is H.
In some embodiments of Group 10, none of Y1, Y2, Y3 and Y4 are N. in some embodiments, one of Y1, Y2, Y~3 and Y4 is N. In some embodiments, R1 and R2 are independently D; at least one of R3 and R4 is A. In some embodiments, R3 and R3 are independently D; at least one of R2 and R4 is A. In some embodiments, Rf and R4 are independently D; at least one of R2 and R3 is A. In some embodiments, R2 and R' are independently D; at least one of R1 and R4 is A. In some embodiments, R2 and R4 are independently D: at least one of R1 and R3 is A. in some embodiments, R3 and R4 are independently D; at least one of R1 and R2 is A. In some embodiments, the remaining one of R1, R2, R3 and R4 is selected from H, deuterium, unsubstituted alkyl and imsubstituted phenyl. In some embodiments, the remaining one of R1, Rz, R3 and R4 is selected from H and imsubstituted phenyl. In some embodiments, none of Y5, Y6, Y' and Y8 are N. In some embodiments, two of Y5, Yb, Y1 and Ys are N. In some embodiments, one of Y\ Y°, Y' and Y8 is N. In some embodiments, Y5 is N. In some embodiments, Y6 is N. In some embodiments, Y' is N. In some embodiments, Y8 is N. In some embodiments, one of Y'5, Y6, Y7 and Y8 is N; R3 is A.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 11") satisfying that only one of R5, R6, R7 and Rs is D. In some embodiments of Group 11, R5 is D. In some embodiments, R6 is B. In some embodiments, R7 is D. In some embodiments, R8 is D. In some embodiments, one of R5, R6, R' and R8 is D; and the others of R5, R°, R; and 8 are not A. In some embodiments, one of R5, R6, R7 and Rs is D; and the others of R5, R6, R7 and Rs are H. In some embodiments, one of Y5, Y6, Y7 and Y8 is N. In some embodiments, Y5 is N. In some embodiments, Yt is N. in some embodiments, Y3 is N. in some embodiments, Y8 is N. in some embodiments, one of Y5, Y6, Y7 and Y8 is N; R3 is A. In some embodiments, one of Y3, Y6, Y7 and Y8 is N; and none of Y1, Y~2, Y3 and Y4 are N. in some embodiments, one of Y'5, Y6, Y' and Y8 is N: and one of Y1, Y2, Y3 and Y4 is N. in some embodiments, one of Y5, Y6, Y1 and Y8 is N; and Y4 is N. in some embodiments, Y~4 and Y3 are N. In some embodiments, Y4 and Y° are N. in some embodiments, Y~4 and Y' are N in some embodiments, Y4 and Y8 are N. in some embodiments, R6 is D; two of R1, R2, R3 and R4 are D; at least one of R1, R2, R3 and R4 is A. In some embodiments, R6 is B; two of R1, R2, R3 and R4 are D; one of R1, R2, R3 and R4 is A, the other remaining one of R1, R2, RJ and R4 is H or unsubstituted phenyl in some embodiments, R ' is D; two of R1, R2, R3 and R4 are D; at least one of R1, R2, R3 and R4 is A. in some embodiments, R7 is D; two of R1, R2, R3 and R4 are D; one of R1, R2, R3 and R4 is A, the other remaining one of R1, R2, R3 and R4 is H or unsubstituted phenyl.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 12") satisfying that Y6 is R6-C; Y' is R7-C; R6 and R7 are independently D; and at least one of Y1, Y2, Y3, Y4, Y3 and Y8 is N.
In some embodiments of Group 12, one or two of Y3, Y2, Y3 and Y4 are N; and none of Y3 and Ys are N. In some embodiments, none of Y1, Y2, Y3 and Y4 are N; and at least one of Y3 and Y8 is N. In some embodiments, one of Y1, Y2, Y3 and Y4 is N; and one of Y5 and Y8 is N. In some embodiments, Y4 is N; and one of Y5 and Y8 is N. In some embodiments, at least one of Y1, Y2, Y3 and Y4 is N; and R3 is A. In some embodiments, R1 and R2 are independently D; at least one of R3 and R4 is A. In some embodiments, R1 and R3 are independently D; at least one of R2 and R4 is A. In some embodiments, Rf and R4 are independently D; at least one of R2 and R3 is A. In some embodiments, R2 and R3 are independently D; at least one of R1 and R4 is A. In some embodiments, R2 and R4 are independently D; at least one of R1 and R3 is A. In some embodiments, R3 and R4 are independently D; at least one of R1 and Rz is A. In some embodiments, the remaining one of R5, R2, R3 and R4 is selected from H, deuterium, unsubstituted alkyl and unsubstituted phenyl. In some embodiments, the remaining one of R1, R2, R3 and R4 is selected from H and unsubstituted phenyl.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 13") satisfying that Yb is Rf -C; Y7 is R7-C; R6 and R7 are independently D; none of Y1, Y2, Y3, Y4, Y3, Y6, Y7 and Y8 are N; and two of R1, R2, R3 and R4 are independently D and these two differ from each other.
In some embodiments of Group 13, R1 and R2 are independently B; at least one of RJ and R4 is A. in some embodiments, R1 and R3 are independently D; at least one of R2 and R4 is A. in some embodiments, R1 and R4 are independently D; at least one of R2 and R3 is A. In some embodiments, R2 and R3 are independently D; at least one of R1 and R4 is A. In some embodiments, R and R4 are independently D; at least one of R1 and RJ is A. In some embodiments, RJ and R4 are independently D; at least one of R1 and R2 is A. In some embodiments, the remaining one of R1, R2, R3 and R4 is selected from H, deuterium, unsubstituted alkyl and unsubstituted phenyl. In some embodiments, the remaining one of R1, Rz, RJ and R4 is selected from H and unsubstituted phenyl In some embodiments, R5 and R8 are selected from H, unsubstituted phenyl In some embodiments, Rs and R8 are H.
In some preferred embodiments, the compound of Formula (I) is selected from the group (which is hereinafter referred to as "Group 14") satisfying at least one of the foil owing conditi ons :
1) Y' is R5-C, and R5 is A;
2) Y6 is R6-C, and R6 is A;
3) Y7 is R7-C, and R' is A; and
4) Y8 is R8-C, and Rs is A. In some embodiments of Group 14, only 1) is satisfied. In some embodiments, only 2) is satisfied. In some embodiments, only 3) is satisfied. In some embodiments, only 4) is satisfied. In some embodiments, Rf and R2 are independently D: at least one of R' and R4 is A. in some embodiments, R! and R3 are independently D; at least one of R2 and R4 is A. In some embodiments, R1 and R4 are independently D; at least one of R2 and R3 is A. In some embodiments, R2 and R3 are independently D; at least one of R1 and R4 is A. in some embodiments, R2 and R4 are independently D; at least one of R1 and RJ is A. In some embodiments, RJ and R4 are independently D; at least one of R1 and Rz is A In some embodiments, the remaining one of R1, R2, R J and R4 is selected from H, deuterium, unsubstituted alkyl and unsubstituted phenyl. In some embodiments, the remaining one of R1, R2, R' and R4 is selected from H and unsubstituted phenyl in some embodiments, one of Y5, Yb, Y7 and Y8 is N. In some embodiments, Y5 is N. in some embodiments, Y6 is N. In some embodiments, Y? is N. In some embodiments, Y8 is N. in some embodiments, one of Y1, Y2, Y3 and Y4 is N. in some embodiments, Y1 is N. In some embodiments, Y2 is N. In some embodiments, Y3 is N. in some embodiments, U4 is N. in some embodiments, one of Y1, Y2, Y3 and Y4 is N; and one of Y5, Y6, Y7 and Y8 is N. in some embodiments, Y4 is N; and one of Y5, Y6, Y7 and Y8 is N. In some embodiments, one of Y2, Y6, 7 and Y8 is N; and A3 is A.
In some embodiments, the compound of Formula (I) is selected from the compounds shown in the following tables. The compounds in the tables are represented by the following formula wherein Y1 is N or R^-I^-C, 2 is N or R2'~L2-C, Y3 is N or R3'-L3-C, Y4 is N or R4,-L4-C, Y5 is N or R5,-L5-C, Y6 is N or R6'-L6-C, Y7 is N or R7,-L7- C, and Y8 is N or R8'-LAC. In the following table, Zi represents nnsubstituted phenyl. When Y1 is Rl -L!-C, Y2 is R2,-L2-C, Y3 is R3'-L3-C, Y4 is R4,-L4-C, Y5 is R5,-L5-C, Y6 is R6’-L6-C, Y' is R/'-L?-C, and Y8 is RS'~L8-C, the cells of Y1 to Y8 in the table are marked
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Compounds 6713 to 13426 are also exemplified that correspond to Compounds 1 to 6712 but has S instead of O at the position of X, respectively.
Compounds 1 to 20290 shown in United States Provisional Patent Application serial number 62/950,669, filed December 18, 2019, are hereby expressly incorporated by reference into the present application.
In some embodiments the compound of Formula (I) is selected from the following compounds.
Figure imgf000147_0001
In some embodiments the compound of Formula (I) is selected from the following compounds.
Figure imgf000147_0002
Figure imgf000148_0001
Figure imgf000149_0001
In some embodiments, compounds of Formula (I) are substituted with deuterium.
In some embodiments, compounds of Formula (I) are light-emitting materials.
In some embodiments, compounds of Formula (I) are compound capable of emitting delayed fluorescence.
In some embodiments, compounds of Formula (I) are light-emitting materials. In some embodiments, compounds of Formula (I) are assistant dopant materials. In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce light in ultraviolet region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nrn to about 500 nm, about 500 nm to about 600 iim, or about 600 mn to about 700 nm), or near-mfrared region.
In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce light in the red or orange region of the visible spectrum (e.g., about 620 mn to about 780 nm; about 650 nm). in some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce 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).
In some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm; about 510 nm). in some embodiments of the present disclosure, when excited via thermal or electronic means, the compounds of Formula (I) can produce light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm; about 475 nm).
Electronic properties of a library of small chemical molecules can be computed using known ab initio quantum mechanical computations. For example, using a time- dependent density functional theory using, as a basis set, the set of functions known as 6- 31G* and a Becke, 3 -parameter, Lee- Yang-Parr hybrid functional to solve Hartree-Fock equations (TD-DFT/B3LYP/6-31 G*), molecular fragments (moieties) can be screened which have HQMOs above a specific threshold and LUMOs below' a specific threshold, and wherein the calculated triplet state of the moieties is above 2.75 eV.
Therefore, for example, a donor moiety (“D”) can be selected because it has a HOMO energy (e.g., an ionization potential) of greater than or equal to -6.5 eV. An acceptor moiety (‘24”) can be selected because it has, for example, a LUMO energy' (e.g., an electron affinity) of less than or equal to -0.5 eV. Hie linker moiety (“L”) can be a rigid conjugated sy stem which can, for example, sterical!y restrict the acceptor and donor moieties into a specific configuration, thereby preventing the overlap between the conjugated p system of donor and acceptor moieties.
In some embodiments, the compound library' is filtered using one or more of the following properties: 1. emission near a certain wavelength;
2. calculated triplet state above a certain energy level;
3. D EST value below a certain value;
4. quantum yield above a certain value; 5. HOMO level; and
6 LUMO level in some embodiments, the difference between the lowest single! excited state and the lowest triplet excited state at 77K ( D EST) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. in some embodiments, the A EST 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.
In some embodiments, a compound of Formula (1) exhibits a quantum yield of greater than 25%, such as about 3Q%, 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.
Preparation of the Disclosed Compounds
The compounds of Formula (I) can be synthesized by any method known to one of ordinary skills in the art. The compounds are synthesized from the commonly available starting material. For example, the compound of Formula (I) wherein X is (), Y1 is Ri-C, Y2 is R2-C, Y3 is R3~C, Y4 is R4-C, R1, R5 and R4 are 9-carbazolyl, R2 is CN, and R5, R6, R7 and Rs are H can be synthesized by the following scheme.
Figure imgf000151_0001
Figure imgf000152_0001
The reaction conditions for the above reactions are shown in Example 1 below. It is obvious to a person skilled in the art to change the materials used for the reactions and modify the reaction conditions to produce other compounds of Formula (I).
Film Formation in some embodiments, a film containing a compound of the present invention of Formula (I) can be formed in a wet process in a wet process, a solution prepared by dissolving a composition containing a compound of the present invention is applied to a surface and formed into a film thereon after solvent removal. A wet process includes, though not limited thereto, a spin coating method, a slit coating method, a spraying method, an inkjet method (a spay method), a gravure printing method, an offset printing method, and a flexographic printing method. In a wet process, a suitable organic solvent capable of dissolving a composition containing a compound of the present invention is selected and used in some embodiments, a substituent (for example, an alkyl group) capable of increasing solubility in an organic solvent can be introduced into the compound contained in the composition.
In some embodiments, a film containing a compound of the present invention can be formed in a dry process. In some embodiments, a dry process includes a vacuum evaporation method, but is not limited thereto. In the case of employing a vacuum evaporation method, compounds to constitute a film can be vapor-eo-deposited from individual evaporation sources, or can be vapor-co-deposited from a single evaporation source of a mixture of the compounds. In the case of using a single evaporation source, a mixed powder prepared by mixing powders of compounds may be used, or a compression-molded body prepared by compressing the mixed powder may be used, or a mixture prepared by heating, melting and cooling compounds may he used. In some embodiments where vapor-co-depositi on is carried out under such a condition that the evaporation rate (weight reduction rate) of the plural compounds contained m a single evaporation source is the same or is nearly the same as each other, a film whose composition ratio corresponds to the composition ratio of the plural compounds contained in the evaporation source can be formed. Under the condition where plural compounds are mixed to make an evaporation source m a composition ratio that is the same as the composition ratio of the film to be formed, a film having a desired composition ratio can be formed in a simplified manner. In some embodiments where a temperature at which the compounds to be vapor-co-deposited could have the same weight reduction ratio is identified, and the temperature can be employed as the temperature in vapor-codeposition. EXAMPLES
An embodiment of the present disclosure provides the preparation of compounds of Formula (I) according to the procedures of the following example(s), using appropriate materials. Those skilled in the art will understand that known variations of the conditions and processes of the following preparative procedures can be used to prepare these compounds. Moreover, by utilizing the procedures described in detail, one of ordinary skill in the art can prepare additional compounds of the present disclosure.
General Information on Analytical Methods
The features of the invention will be described more specifically with reference to examples below. The materials, processes, procedures and the like shown below may be appropriately modified unless they deviate from the substance of the invention. Accordingly, the scope of the invention is not construed as being limited to the specific examples shown below'. The characteristics of samples were evaluated by using NMR (Nuclear Magnetic Resonance 500 MHz, produced by Bruker), LC / MS (Liquid Chromatography Mass Spectrometry, produced by Waters), ACS (produced by R!KEN KE1KI), High-performance UV/Vis/NiR Spectrophotometer (Lambda 950, produced by
PerkinElmer, Co., Ltd.), Fluorescence Spectrophotometer (FluoroMax-4, produced by Horiba, Ltd.), Photonic multichannel analyzer (PMA-12 Cl 0027-01, produced by Hamamatsu Photonics K.K.), Absolute PL Quantum Yield Measurement System (Cl 1347, produced by Hamamatsu Photonics K.K.), Automatic Current voltage brightness measurement system (ETS-I70, produced by System engineers co ltd), Life
Time Measurement System (EAS-26C, produced by System engineers co ltd), and Streak Camera (Model C4334, produced by Hamamatsu Photonics K.K.). Example 1
The principle of the features may be described as follows for an organic electroluminescent device as an example.
In an organic electroluminescent device, carriers are injected from an anode and a cathode to a light-emitting material to form an excited state for the light-emitting material, with which light is emitted. in the case of a carrier injection type organic electroluminescent device, in general, excitons that are excited to the excited singlet state are 25% of the total excitons generated, and the remaining 75% thereof are excited to the excited triplet state. Accordingly, the use of phosphorescence, which is light emission from the excited triplet state, provides a high energy utilization. However, the excited triplet state has a long lifetime and thus causes saturation of the excited state and deactivation of energy through mutual action with the excitons in the excited triplet state, and therefore the quantum yield of phosphorescence may generally he often not high. A delayed fluorescent material emits fluorescent light through the mechanism that the energy of excitons transits to the excited triplet state through intersystem crossing or the like, and then transits to the excited singlet state through reverse intersystem crossing due to triplet-triplet annihilation or absorption of thermal energy, thereby emitting fluorescent light. It is considered that among the materials, a thermal activation type delayed fluorescent material emitting light through absorption of thermal energy is particularly useful for an organic electroluminescent device in the case where a delayed fluorescent material is used in an organic electroluminescent device, the excitons in the excited singlet state normally emit fluorescent light. On the other hand, the excitons in the excited triplet state emit fluorescent light through intersystem crossing to the excited singlet state by absorbing the heat generated by the device. At this time, the light emitted through reverse intersystem crossing from the excited triplet state to the excited singlet state has the same wavelength as fluorescent light since it is light emission from the excited singlet state, but has a longer lifetime (light emission lifetime) than the normal fluorescent light and phosphorescent light, and thus the light is observed as fluorescent light that is delayed from the normal fluorescent light and phosphorescent light. The light may be defined as delayed fluorescent light. Tire use of the thermal activation type exciton transition mechanism may raise the proportion of the compound in the excited singlet state, which is generally formed in a proportion only of 25%, to 25% or more through the absorption of the thermal energy after the earner injection. A compound that emits strong fluorescent light and delayed fluorescent light at a low' temperature of lower than 1Q0°C undergoes the intersystem crossing from the excited triplet state to the excited singlet state sufficiently with the heat of the device, thereby emitting delayed fluorescent light, and thus the use of the compound may drastically enhance the light emission efficiency.
Example 2
The compounds of the invention can be synthesized by any method known to one of ordinary skills in the art. The compounds are synthesized from the commonly available starting material. The various moieties can be assembled via linear or branched synthetic routes.
Synthesis of2-bromo-3,4-difluorodibenzo[b,d]furan
Figure imgf000155_0001
l,5-Dibromo-2,3,4-trifluorobenzene (5 g, 17.25 mmol), (2-hydroxyphenyl)boronic add (15.52 mmol), Na:CCh (51.75 mmol, 2M in aqueous solution) and PdiPPhsft (3 mol%) were dissolved in THF and distilled water (depending on amount of NaaCO). The solution was refluxed for 12h under a nitrogen atmosphere and then cooled down to room temperature. The solution was extracted using ethyl acetate and distilled water. The solution of an organic layer was evaporated under vacuum and purified by flash column chromatography using ethyl acetate hexane (1 :4) as an eluent in order to remove starting materials the hydroxy group. The crude reaction mixture was obtained about 2.5 g. After flash column purification, the crude reaction mixture (2.5 g, 8.25 mmol) and K2CO3 (24.75 mmol) were dissolved in DMF. The solution was stirred for 3 hours at 70 Celsius degree under a nitrogen atmosphere and then cooled down to room temperature. The reaction progress checked by TLC. The solution was extracted using ethyl acetate and distilled water. Solvent of the organic layer was evaporated under vacuum and purified by column chromatography using ethyl acetate:hexane (1 :4) as an eluent. The white powdery- product was obtained about 2 g.
1H NMR (500 MHz, CDCb) d 7.39 (t, ./ 7.5 Hz, Hi), 7.52 (t, J = 7.5 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H). 7 86-7.87 (m, .211). i9F NMR (470 MHz, CDCb) 6 -155.86 (d, JF = 18.8, IF), -130.46 id../; 18.8 Hz, IF), MS (APCI) m/z 281.91 [(M)+] Syn thesis of 9, 9'-(( 3r, 4r) -2-bromodi benzoj b, d] fur an- 34-diyl) bis ( 9H -carbazole)
Figure imgf000156_0001
Potassium carbonate (21.20 mmol, 2.93 g), 2-bromo-3,4- difluorodibenzo[b,d]furan (7.07 mmol, 2.00 g) and 9i/-carbazole (21.20 mmol, 3.54 g) were placed in three neck round bottom flask. The mixture dried by vacuum system and then DMF was poured into flask as solvent under nitrogen atmosphere. The reaction mixture stirred overnight keeping at 160 Celsius degree. The reaction quenched by NH4CI in aqueous solution and the mixture extracted by chloroform. The separated organic layer dried by MgSCri and concentrated solvent by vacuum evaporator system. The reaction product was isolated by column chromatography using a mixture of ethyl acetate and hexane (1:4) as an eluent. A final product was obtained (3.50g, 85.8%).
'l l NMR (500 MHz, CDCh) d 6.93 (d, J= 8 Hz, 211}. 6.98-7.08 (m, lul l). 7.45-7.55 (m, 311). 7.75 (t, J = 8.0 Hz, 411). 8.09 (d, J = 7.5 Hz, 111). 8.59 (s, 111). MS (APCI) m/z 577 37 itVl ) 1) |.
Figure imgf000156_0002
Compound 6712
9,9'-((3r,4r)-2-bromodibenzo[b,d]furan-3,4-diyl)bis(9i/-carbazole) (1.00 g, 1.73 mmol), was dissolved in THF. The solution was stirred under a nitrogen atmosphere and then cooled down to ~ 80 Celsius degree. And then, n-BuLi solution (0.93 niL, 1.6 M in Hexane) dropwise to solution flask slowly and kept stirring under same atmosphere. And in a 1 hour later, a triisopropyl borate (0.49 g, 2.60 mmol) dropwise to solution flask slowly, then flask temperature increased to room temperature in nature. The reaction solution quenched by 5 wt% HCI solution, and then was extracted using dichlorometane and distilled water. The solution of an organic layer was evaporated under vacuum and the solution used right away in next step reaction without further purification. ((3s,4r)- 3,4-Di(9//-carbazoi-9-yi)dibenzoib,djiuran-2-y!)bofonic acid (0.90 g, 1.66 mmol), 2- chloro-4,6-dipbenyl-l,3, 5-triazine (0.46 g, 1.83 mmol), potassium carbonate (0.69 g, 4.98 mmol) and tetrakis(triphenylphosphine)palladium(0) (3 mo! ‘TO were dissolved in THF and distilled water (depending on amount of K2CO3) with inert atmosphere. The solution was refluxed for 12h under a nitrogen atmosphere and then cooled down to room temperature. The solution was extracted using ethyl acetate and distilled water. The solution of an organic layer was evaporated under vacuum and purified by column chromatography using ethyl acetate: hexane (1 :4) as an eluent. The tight yellowish white powdery product was obtained about 0.81 g (Compound 6712, 66.8%).
'P NMR (500 MHz, CDCh) d 6.93-6.99 (m, 4H), 7.00-7.12 (ra, 6H), 7.15 (d, J= 8.0 Hz, 2H), 7.28-7.31 (m, 4H), 7.43-7.56 (m, 5H), 7.59 (d, J= 7.5 Hz, 2H), 7.86 (d, J = 7.5 Hz, 2H), 7.97 (d , J = 8.0 Hz, 41 !}. 8.25 (d, J = 7.5 Hz, III), 9.12 (s, I I I). MS (APCI) m/z 730.39 [(M+H)+]
Example 3
Figure imgf000157_0001
2-bromo-3,4-difluorodibenzo[b,d]furan (3.00 g, 10.60 mmol) was dissolved in THF. The solution was stirred under a nitrogen atmosphere and then cooled down to - 80 Celsius degree. And then, n-BuLi solution (6.62 mL, 1.6 M m Hexane) dropwise to solution flask slowly and kept stirring under same atmosphere. And in a 1 hour later, a 2- isopropoxy-4,4,5,5-ietrarnethyl-l,3,2-dioxaborolane (2.96 g, 15.90 mmol) dropwise to solution flask slowly, then flask temperature increased to room temperature in nature. The reaction solution quenched by distilled water, and then was extracted using dichlorometane and distilled water. The solution of an organic layer was evaporated under vacuum and the solution used right away in next step reaction without further purification. 2-(3,4-difluorodibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyi-l,3,2-dioxaborolane (3.50 g, 10.60 mmol), 2-chloro-4,6-diphenyl-l, 3, 5-triazine (3.12 g, 11.66 mmol), potassium carbonate (1.47 g, 10.60 mmol) and tetrakis(tnphenylphosphine)palladmm(0) (3 mol%) were dissolved in THF and distilled water (depending on amount of K2CO3) with inert atmosphere. The solution was refluxed for 12h under a nitrogen atmosphere and then cooled down to room temperature. The solution was extracted using ethyl acetate and distilled water. The solution of an organic layer was evaporated under vacuum and purified by column chromatography using ethyl acetate:hexane (1:4) as a eluent. The white powdery product was obtained about 2,20 g (47.7%).
¾ NMR (500 MHz, CDCI3) d 747 (t, J= 8.0 Hz, IH), 7.56 (t, J= 8.0 Hz, IH), 7.59-7.69 On. 7H), 8.10 (d, J = 7.5 Hz, 1H), 8.79 (d, J = 8.0 Hz, 41 IT 8.85 (d, J = 6.0 Hz, IH), MS (APCI) 436.12 m / | < \ I 11 ) |.
Synthesis of Compound 293
Figure imgf000158_0001
Compound 293
Potassium carbonate (6 89 mmol, 0.95 g), 2-(3,4-difluorodibenzo[b,d]furan-2-yl)- 4,6-diphenyl-l,3,5-triazine (2.30 mmol, 1.00 g) and 3-phenyl-9H-carbazole (5.74 mmol, 1.40 g) were placed in three neck round bottom flask. The mixture dried by vacuum system and then DMF was poured into flask as solvent under nitrogen atmosphere. The reaction mixture stirred overnight keeping at 160 Celsius degree. The reaction quenched by NH4CI in aqueous solution and the mixture extracted by chloroform. The separated organic layer dried by MgSCfi and concentrated solvent by vacuum evaporator system. The reaction product was isolated by column chromatography using a mixture of toluene and hexane (1:4) as an eluent. A final product was obtained (Compound 293, 1.5Qg, 74.0%).
'1 ! NMR (500 MHz, CDCh) d 6.96 (t, ./= 7.5 Hz, IH), 7.02-7.30 (m, 1311). 7.34-7.44 (m, 8H), 7.49-7.57 (m, 6H), 7.62 (t, J= 7.5 Hz, 2H), 7.83 (s, IH), 7.89-7.94 (m, IH), 7.99 (d,
J = 7.5 Hz, 4H), 8.07 (d, J = 16.5 Hz, IH), 8.25 (d, J = 7.0 Hz, IH), 9.13 (s, IH), MS (APCI) m/z 882,32 | ( \ 1 11) j. Example 4
Figure imgf000159_0001
Compound 269
Potassium carbonate (6.89 mmol, 0.95 g), 2~(3,4-difluorodibenzo[b,d]furan-2-yl)~ 4,6~diphenyl-l,3,5-triazine (2,30 mmol, 1.00 g) and 3,6-diphenyi~9H~carhazo!e (5.74 mmol, 1.83 g) were placed in three neck round bottom flask. The mixture dried by vacuum system and then DMF was poured into flask as solvent under nitrogen atmosphere. The reaction mixture stirred overnight keeping at 160 Celsius degree. The reaction quenched by NH4CI in aqueous solution and the mixture extracted by chloroform. The separated organic layer dried by MgSCfi and concentrated solvent by vacuum evaporator system. The reaction product was isolated by column chromatography using a mixture of toluene and hexane (1:4) as an eluent. A final product was obtained (Compound 269, 1.9g, 80.0%).
Figure imgf000159_0002
7.32 (m, 14H), 7.34-7.47 ( , 13H), 7.50 (d, ./ = 8.0 Hz, 4H), 7.59 (d, J = 8.0 Hz, 6H), 7.86 (s, IH), 8.03 (d, J= 8.0 Hz, 4H), 8. 13 (s, IH), 8.29 (d, J= 7.5 Hz, 1H), 9.18 (s, IH), MS (APCI) m/z 1035 [(M+H j.
Example S
Synthesis of 2-chloro-5-(3, 6-dimethyl-9H-carbazole-9-yl)-phenol
Figure imgf000159_0003
2-chloro-5-bromo-phenol (2.00 g, 9.64 mmol), 3,6-dimethyl -9H-carbazole (18.8 g, 9.64 mmol), «-BtnPHBFT (0.38 g, 0.96 mmol), /-BuONa (2.78 g, 20.92 mmol) and Pd2(dba) (0.44 g, 0.48 mmol) in toluene. (70 niL) were stirred at 110 °C for 15 h under a nitrogen atmosphere. After reaction, the flask temperature increased to room temperature and the reaction solution was filtered through the cehte. The resulting solution was evaporated under vacuum and the residue was purified by column chromatography using dichloromethane as a eluent. The light white powdery product was obtained about 2.50 g (80.6%).
'P NMR (400 MHz, CDCh) d 7.88 (s, 2H), 7.51 (d, J = 8.0 Hz, i l l }. 7.32 id. J= 8.8 ! iz. 2H), 7.25 (s, 1H), 7.21 (dd, J= 8.0 and 1.2 Hz, 2H), (d, dd, J= 8.0 and 2.0 Hz, 1H), 5 69 (br, i l l). 2.53 (s, 6H), MS (APCI) m/z 322.11 |{ VI 11)
Synthesis of S-hromo-2, 3-bis(3, 6-dimethyl-9H-carhazol~9~yl)~terephthalonitrile
Figure imgf000160_0001
A mixture of K2CO3 (0.86 g. 6.22 mmol), 3,6-dimeihyl-SW-carbazole (0.95 g, 4.94 mmol) and 5-bromo-2,3-difluoroterephthalonitrile (0.6 g, 2.47 mmol) in 15 mL DMF was stirred at 50 °C for 4 h. The reaction mixture was quenched with MeOH and H2O. The precipitate was filtered, washed with MeOH, and purified by column chromatography using toluene as eluent. The yellow powdery product was obtained about 0.81 g (54.0%). lH NMR (500MHz, CDCh, S): 8.28 (s, M l). 7.48 (s, 4H), 6.85 d, J = 8.0 Hz, 4H), 6.79 (t, J= 9.0 Hz, 4H), 2.36 (s, 12H). MS (APCI) m/z 593 20 |(VM 1) |. Synthesis of (s)-5-(2-chloro-5-(3, 6-dimethyl~9H~carbazol-9-yl)phenoxy)~2, 3-
Figure imgf000160_0002
Potassium carbonate (1.58 mmol, 0.22 g), 5-bromo-2,3-bis(3,6-dimethyl-9H- carbazo3-9-yl)-tereph†halomtriie (1.06 mmol, 0.63 g) and 2-chloro-5-(3,6~dimethyl-9H~ carbazo3e~9-y3)-pheno! (1.06 mmol, 034 g) -were placed three neck round bottom flask. The mixture dried by vacuum system and then DMF (8mL) was poured into flask as solvent under nitrogen atmosphere. The reaction mixture stirred overnight keeping at 80 °C. The reaction quenched by water and MeOH and the mixture and the precipitate was filtered, and was washed with MeOH. The reaction product was isolated by column chromatography using a mixture of dichloromethane and hexane (2:1) as an eluent. The yellow' powdery product was obtained about 0.71 g (81.0%).
¾ NMR (400 MHz, CDCh) d 7.92 (s, 2H), 7.86-7.84 (d, J = 9.2 Hz, 1H), 7.67-7.64 (m, 2H), 7.49 (s, 4H), 7.41 (d, J= 8.0 Hz, 2H), 7.32 (s, 1H), 7.29 (d, J = 7.2 HZ,2H), 6.89 (d, J = 8.0 Hz, 2H), 6.86-6.83(m, 4H), 6.79 (d, J 8.0 Hz, H i). 2.56 (s, 6H), 2.36 (s, 6H), 2.35 (s, 6H), MS (APCI) m/z 834.12 |i.YM H |.
Synthesis of Compound 6591
Figure imgf000161_0001
Compound 6591
A mixture of (s)-5-(2-chloro-5-(3,6-diniethyl-9H-carbazol-9-yl)phenoxy)-2,3- bis(3,6-dimethyl-9H-carbazol-9-yl)terephthalomtrile (2.06 g, 2.47 mmol) , K2CO3 (0.66 g, 4.94 mmol), tricyclohexylphosphine (0.07 g, 0.25 mmol), dichlorobis(triphenylphospbine)palladium (0.09 g, 0.12 mmol) and 2-ethylhexanoic acid (004 g, 025 mmol) in xylene (100 rnL) was stirred at 125 °C for 16 h. After the reaction completed, the inorganic solid was removed by Celite filtration, and to the Cehte was washed by CHCb. The filtrate was concentrated under reduced pressure. The obtained crude was purified by column chromatography using toluene/hexane :::: 2/1 as eluent. The yellow powdery product was obtained about 1.42 g (Compound 6591, 76.0%).
!H NMR (400MHz, CDCh, d): 8.68 (d, J= 8.8, i l l). 8.09 (s , i l l). 7.94 (s, 2H), 7.88 (dd, J= 7.2 and 1.6 Hz, 1H), 7.21 (d, ./ 8.0 Hz, 2. Hi. 7.55-7.48 (m, 6H), 7.29 (dd, J= 7.6 and
1.2 Hz, 2H), 6.93-6.87 (m, 8H) 2.58 (s, 6H), 2.40 (s, 6H), 2.39 (s, 611} MS (APCI) m/z 798.44 i(\! 11) |.
Example 6
Preparation of neat film
In this example, Compound 6712 synthesised in Example 2 was vapor-deposited on a quartz substrate by a vacuum vapor deposition method under a condition of a vacuum degree of 103 Pa or less, so as to form a thin film having a thickness of 70 nm.
Compounds 293 and 269 were used instead of Compound 6712 to prepare thin films in the same manner, respectively.
Preparation of doped film
Compound 6712 and PYD2Cz were also vapor-deposited from a separate vapor deposition source on a quartz substrate by vacuum vapor deposition method under a condition of a vacuum degree of 103 Pa or less, so as to form a thin film having a thickness of 100 nm and a concentration of Compound 6712 of 20% by weight.
Compounds 293 and 269 were used instead of Compound 6712 to prepare doped films in the same manner, respectively.
Evaluation of the optical properties The samples are irradiated with light having a wavelength of 300 nm at 300 , and thus the light emission spectrum was measured and designated as fluorescence. The spectrum at 77K was also measured and designated as phosphorescence. The lowest singlet energy (Si) and the lowest triplet energy (Ti) were estimated from the onset of fluorescence and phosphorescence spectmni respectively. D EST was calculated from the energy gap between Si and Ti. Photoiuminescenee quantum yield (PLQY) and emission peak wavelength of fluorescent light ( l ) were measured. The time resolved spectrum was obtained by excitation light 337nm with Streak Camera, and the component with a short light emission lifetime was designated as fluorescent light, whereas the component with a long light emission lifetime was designated as delayed fluorescent light. The lifetimes of the fluorescent light component (xPrompt) and the delayed fluorescent light component (idsiay) were calculated from the decay curves. The measurement results are shown in the table below.
Preparation and measurement of OLED Thin films were laminated on a glass substrate having formed thereon an anode formed of indium tin oxide (PΌ) having a thickness of 50 nm, by a vacuum vapor deposition method at a vacuum degree of 1.0 x 104 Pa or less. Firstly, HAT-C is formed to a thickness of 60 n on ITO, and thereon TrisPCz is formed to a thickness of 30 nm. PYD2Cz was formed to a thickness of 5 nm, and thereon Compound 6712 and PYD2Cz were then vapor-co-deposited from separate vapor deposition sources to fomi a layer having a thickness of 30 nm, which is designated as a light-emitting layer. At this time, the concentration of Compound 6712 was 30% by weight. SF3-TRZ was formed to a thickness of 10 nm, and thereon SF3-TRZ (70wt%) and Liq were vapor-co-deposited to a thickness of 30 nm. Liq was then vacuum vapor-deposited to a thickness of 2 nm, and then aluminum (All was vapor-deposited to a thickness of 100 nm to form a cathode, thereby producing organic electroluminescent devices.
Compounds 293 and 269 were used instead of Compound 6712 to prepare organic electroluminescent devices in the same manner, respectively. External quantum efficiency (EQE) of each produced device was measued at 1000 cd. The results are shown in the following table.
Figure imgf000163_0002
Figure imgf000163_0001

Claims

1. An organic light-emitting diode (OLED) comprising a compound of
Formula (I):
Figure imgf000164_0001
wherein:
X is O or S,
Y1 is N or RLC, Y2 IS N or R2-C, Y3 is N or R3-C, Y4 is N or R4-C, Y5 is N or R5-C, Y6 is N or R6~C, Y7 is N or R7-C, and Y8 is N or R8-C, provided that at most two of Y1, Y2, Y Y4, Y5, Y6, Y' and Y8 are N, one or more of R1, R2, R3, R4, R5, R6, R' and R8 are independently D, other one or more of R\ R2, R3, R4, R5, R°, R7 and R8 are independently A, the other remaining R1, R2, R3, R4, R5, R6, R? and R8 are independently selected from H, deuterium, substituted or imsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl, two or more of R1, RA R3 and R4 taken together can form a ring system, two or more of R5, R6, R' and R8 taken together can form a ring system, A is selected from CN-L·4-*, PFA-L·4-* or Het- 1/4-*
PFA is perfluoroalkyl.
Het is substituted or imsubstituted heteroaryl having at least one nitrogen atom as a ring-constituting atom,
D is group of Formula (Ha), (lib), (lie) or (lid):
Figure imgf000164_0002
R° is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aJkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, and silyl; two or more instances of R° taken together can form a ring system;
RD’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; two or more instances of RD’ and R° taken together can form a ring system;
LD and LA are independently selected from single bond, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene; wherein each instance of arylene and heteroarylene can 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 these substituents taken together can form a ring system;
C-RD of the benzene rings in Formulae (11a), (lib), (lie) and (lid) may be substituted with N; and each represents a point of attachment to Formula (1).
2. The organic light-emitting diode (OLED) according to claim 1, wherein A is CN-La-*, PFA-La-* or Het-LA-* in which LA of Het-LA-* is substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene; wherein each instance of arylene and heteroarylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, and wherein two or more of these substituents taken together can form a ring system.
3. The organic light-emitting diode (OLED) according to claim 1 or 2, wherein at least one of D is a group of Formula (lib) and at least one of RD is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, or silyl.
4. The organic light-emitting diode (OLED) according to any one of claims 1 to 3, wherein at least one of D is a group of Formula (lib) and at least one C-RD of the benzene rings in Formula (lib) is substituted with N.
5. The organic light-emitting diode (OLED) according to any one of claims 1 to 4, wherein at least one of D is a group of Formula (lib) and L° is substituted or unsubstituted aryiene, and substituted or unsubstituted heteroaiylene; wherein each instance of aryiene and heteroaryiene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted and, and substituted or unsubstituted heteroary!, and wherein two or more of these substituents taken together can form a ring system.
6. The organic light-emitting diode (OLED) according to claim 1 or 2, wherein D is group of Formula (Ila), (Ik) or (lid).
7. The organic light-emitting diode (OLED) according to any one of claims 1 to 6, wherein at least one of Y3, Y2, Y3, Y4, Y5, Yb, Y7 and Ys is N.
8. The organic light-emitting diode (OLED) according to any one of claims 1 to 7, wherein at least one of R1, R2, R3 and R4 and at least one of R5, R6, R/ and R8 are independently D.
9. The organic light-emitting diode (OLED) according to claim 8, wherein at least one of R6 and R' is D.
10. The organic light-emitting diode (OLED) according to any one of claims 1 to 9, wherein two or more of R1, R2, R', R4, R5, R6, R and R8 are independently A.
11. The organic light-emitting diode (OLED) according to claim 10, wherein two of R1, RA RJ and R4 are independently A and the other two of R1, R2, R3 and R4 are independently D.
12. The organic light-emitting diode (OLED) according to any one of claims 1 to 11, wherein the organic light-emitting diode has a light-emitting layer comprising the compound of Formula (I) as an assistant dopant.
13. The organic light-emitting diode (OLED) according to any one of claims 1 to 12, wherein the organic light-emitting diode has a light-emitting layer comprising a host material, the compound of Formula (I) and a light-emitting material; and the compound of Formula (I) has a lowest excited singlet energy level between the lowest excited singlet energy level of the host material and the lowest excited singlet energy level of the light-emitting material.
14. A compound comprising a compound of Formula (I):
Figure imgf000167_0001
( wherein:
X is O or S, Y1 is N or R!-C, Y2 is N or R2-C, Y3 is N or R3-C, Y4 is N or R4-C, Y5 is N or R5-C, Y6 is N or R/ -C. Y7 is N or R -C. and Y8 is N or kN-C. provided that at most two of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 are N, one or more of R1, R2, R3, R4, R5, R , R; and R8 are independently D, other one or more of R1, R2, R3, R4, R5, R6, R7 and R8 are independently A, the other remaining R]. R2, R3, R4, R5, Rb, R and R8 are independently selected from H, deuterium, substituted or unsubstituted alkyl and substituted or unsubstituted phenyl other than D and A wherein each instance of alkyl and phenyl can be substituted with one or more substituents independently selected from deuterium, alkyl and aryl, two or more of R1, R2, R3 and R4 taken together can form a ring system, two or more of R5, R6, R; and R8 taken together can form a ring system,
A is selected from CN-L4-*, PFA-L4-* or Het- L4-*
PFA is perfluoroalkyl,
Het is substituted or unsubstituted heteroaryl having at least one nitrogen atom as a ring-constituting atom,
D is group of Formula (Ila), (lib), (lie) or (lid):
Figure imgf000167_0002
(Ha) (lib) (lie) ( id)
X' is selected ffomN-RD’, O and S;
R° 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 heteroaryl, substituted or unsubstituted heteroaryloxy, and silyi; two or more instances of R° taken together can form a ring system;
Rd’ is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; two or more instances of RD’ and RD taken together can form a ring system;
LD and LA are independently selected from single bond, substituted or unsubstituted aiylene, and substituted or unsubstituted heteroarylene; wherein each instance of arylene and heteroarylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted and, and substituted or unsubstituted heteroaryl; two or more of these substituents taken together can form a ring system;
C~RD of the benzene rings in Formulae (Ila), (lib), (lie) and (lid) may be substituted with N ; and each represents a point of attachment to Formula (I), provided that at least one of the following <1> to <9> are satisfied:
<1> A is CN-La-*, PFA-La-* or Het-LA-* in winch LA of Het-L·4-* is substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene; wherein each instance of arylene and heteroarylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, and wherein two or more of these substituents taken together can form a ring system,
<2> at least one of D is a group of Formula (lib) and at least one of RD is substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ammo, substituted or unsubstituted aryl, substituted or unsubstituted aiyloxy, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy, or silyi,
<3> at least one of D is a group of Formula (Ilh) and at leas t one C-R° of the benzene rings in Formula (11b) is substituted with N, <4> at least one of D is a group of Formula (lib) and LD is substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene; wherein each instance of arylene and heteroarylene can be substituted with one or more substituents independently selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, and wherein two or more of these substituents taken together can form a ring system,
<5> D is group of Formula (Ila), (lie) or (lid),
<6> at least one of Y1, Y2, Y3, Y4, Y5, Y6, Y7 and Y8 is N,
<7> at least one of R1, R2, R3 and R4 and at least one of R5, Rb, R' and Rs are independently D,
<8> two or more of R1, R2, R3, R4, R5, R6, R7 and R8 are independently A, and
<9> two of R1, R2, R3 and R4 are independently A and the other two of R1, R2, RJ and
R4 are independently D.
15. The compound according to claim 14, wherein at least one of <1>, <3>, <4>, <5>, <6>, <8> and <9> is satisfied.
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