High efficiency and long lifetime organic light-emitting diode

An organic light-emitting diode, comprising:

• a first electrode:
• a second electrode;
• and
• a light-emitting layer interposed between the first electrode and the second electrode,
• wherein the light-emitting layer contains a host and a dopant, the host including at least one of the anthracene compounds represented by the following Chemical Formula A, the dopant including at least one of the polycyclic compounds represented by any one of the following Chemical Formula 3-1 to 4-3:
• wherein
• R, R′, and R1 to R8, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 7 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 30 carbon atoms, a substituted or unsubstituted silyl of 0 to 30 carbon atoms, a substituted or unsubstituted germanium of 0 to 30 carbon atoms, a nitro, a cyano, and a halogen,
• L, which functions as a linker, is any one selected from a single bond, a substituted or unsubstituted arylene of 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene of 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkylene of 7 to 30 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused arylene of 8 to 30 carbon atoms,
• m is an integer of 1 to 3, wherein when m is 2 or higher, the corresponding L's are same or different,
• Ar1 is any one selected from a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 7 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms,
• Dn stands for a number (n) of deuterium atoms substituted for hydrogen atoms in Chemical Formula A,
• n is an integer of 0 to 60,
• p and q, which are same or different, are each independently an integer of 1 to 5, where when p or q is 2 or higher, the corresponding R or R′ radicals are same or different,
• the plural R radicals may be connected to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring, and
• the plural R′ radicals may be connected to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring;
• wherein
• Z1 to Z10, which are same or different, are each independently CR31 or N, when at least two of Z1 to Z10 are each CR31, the corresponding CR31's are same or different,
• when at least two of Z1 to Z10 are each CR31, the corresponding R31's are connected to additionally form an aliphatic or aromatic mono- or polycyclic ring,
• R21 to R31, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, an unsubstituted alkyl of 1 to 24 carbon atoms, an unsubstituted alkynyl of 2 to 24 carbon atoms, an unsubstituted alkenyl of 2 to 24 carbon atoms, an unsubstituted aryl of 6 to 24 carbon atoms, an unsubstituted alkylaryl of 7 to 24 carbon atoms, an unsubstituted cycloalkyl of 3 to 24 carbon atoms, an unsubstituted unsubstituted heterocycloalkyl of 3 to 24 carbon atoms, an uunsubstituted heteroaryl of 2 to 24 carbon atoms, an unsubstituted alkylheteroaryl of 3 to 24 carbon atoms, an unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 24 carbon atoms, an unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 24 carbon atoms, an unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 24 carbon atoms, an unsubstituted aliphatic hydrocarbon ring-fused aryl of 7 to 24 carbon atoms, an unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 24 carbon atoms, an unsubstituted heteroaliphatic ring-fused aryl of 6 to 24 carbon atoms, an unsubstituted heteroaliphatic ring-fused heteroaryl of 5 to 24 carbon atoms, an unsubstituted alkoxy of 1 to 24 carbon atoms, an unsubstituted aryloxy of 6 to 24 carbon atoms, an unsubstituted alkylthioxy of 1 to 24 carbon atoms, an unsubstituted arylthioxy of 5 to 24 carbon atoms, an unsubstituted amine of 1 to 24 carbon atoms, an unsubstituted silyl of 1 to 24 carbon atoms, an unsubstituted germanium of 1 to 24 carbon atoms, a nitro, a cyano, and a halogen,
• R21 to R31 may have at least one deuterium atom instead of a hydrogen atom,
• adjacent radicals among R21 to R30 may be connected to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring,
• when at least one of Z1 to Z10 is CR31, at least one of R21, R25, R26, and R30 may be connected to the corresponding CR31 to additionally form an aliphatic or aromatic mono- or polycyclic ring,
• Y1 to Y3, which are same or different, are each independently as defined in Chemical Formulas 3 and 4 or a linker represented by the following Structural Formula A,
• with a proviso that at least one of Y1 and Y2 is a linker represented by the following Structural Formula A:
• wherein,
• R41 to R45, which are same or different, are each independently any one selected from a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 7 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 30 carbon atoms, a substituted or unsubstituted silyl of 0 to 30 carbon atoms, a substituted or unsubstituted germanium of 0 to 30 carbon atoms, a nitro, a cyano, and a halogen,
• at least one hydrogen atom in R41 to R45 is substitutable with a deuterium atom,
• R41 to R45 may be connected to an adjacent substituent to additionally form an aliphatic or aromatic mono- or polycyclic ring;
• Y1 to Y3, which are same or different, are each independently as defined in Chemical Formulas 3 and 4,
• Z1 to Z10, which are same or different, are each independently CR31 or N,
• when at least two of Z1 to Z10 are each CR31, the corresponding CR31's are same or different,
• when at least two of Z1 to Z8 are each CR31, the corresponding R31's may be connected to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring,
• M is Si or Ge,
• R31 and R46 to R48, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 7 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 30 carbon atoms, a substituted or unsubstituted silyl of 0 to 30 carbon atoms, a substituted or unsubstituted germanium of 0 to 30 carbon atoms, a nitro, a cyano, and a halogen
• at least one hydrogen atom in R46 to R40 is substitutable with a deuterium atom, and
• R46 to R40 may each be connected to additionally form an aliphatic or aromatic mono- or polycyclic ring;
• wherein,
• Z1 to Z11, which are same or different, are each independently CR31 or N,
• when at least two of Z1 to Z11 are each CR31, the corresponding CR31's are same or different,
• when at least two of Z1 to Z11 are each CR31, the corresponding R31's may be connected to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring,
• Y1 to Y3, which are same or different, are each independently as defined in Chemical Formulas 3 and 4, or a linker represented by the following Structural Formula B,
• with a proviso that at least one of Y1 and Y2 is a linker represented by the
• in Structural Formula B and Chemical Formulas 3-3 and 4-3,
• X2 is O or S,
• R31 and R51 to R58, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 7 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 5 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 30 carbon atoms, a substituted or unsubstituted silyl of 0 to 30 carbon atoms, a substituted or unsubstituted germanium of 0 to 30 carbon atoms, a nitro, a cyano, and a halogen,
• at least one hydrogen atom in R51 to R58 is substitutable with a deuterium atom,
• any one of R51 to R58 is a single bond linking to the nitrogen atom,
• adjacent radicals among R51 to R58, except for the single bond, may be connected to each other to additionally form an aliphatic or aromatic mono- or polycyclic ring,
• wherein the term “substituted” in the expression “substituted or unsubstituted” used for compounds of Chemical Formulas A and 3-1 to 4-3 means having at least one substituent selected from the group consisting of a deuterium, a cyano, a halogen, a hydroxy, a nitro, alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 30 carbon atoms, an alkynyl of 2 to 30 carbon atoms, a cycloalkyl of 3 to 30 carbon atoms, a heteroalkyl of 1 to 30 carbon atoms, an aryl of 6 to 30 carbon atoms, an arylalkyl of 7 to 30 carbon atoms, an alkylaryl of 7 to 30 carbon atoms, a heteroaryl of 2 to 30 carbon atoms, a heteroarylalkyl of 3 to 30 carbon atoms, an alkylheteroaryl of 3 to 30 carbon atoms, an alkoxy of 1 to 30 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms, an aliphatic hydrocarbon ring-fused aryl of 7 to 30 carbon atoms, an aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 40 carbon atoms, a silyl of 1 to 40 carbon atoms, a germanium of 1 to 40 carbon atoms aryloxy of 6 to 30 carbon atoms, and an arylthionyl of 6 to 30 carbon atoms, with at least one hydrogen atom in each substituent being substitutable with a deuterium atom.