ORGANIC LIGHT-EMITTING DIODE WITH LOW VOLTAGE, HIGH EFFICIENCY AND LONG LIFESPAN
20260068520 · 2026-03-05
Inventors
- Kyeong Hyeon Kim (Cheongju-si, KR)
- Hyuk Woo Jang (Cheongju-si, KR)
- Do Yeong Choi (Cheongju-si, KR)
- Seo Youn Park (Cheongju-si, KR)
- Kyeong Wan Kim (Cheongju-si, KR)
Cpc classification
C09K11/02
CHEMISTRY; METALLURGY
C07F7/0825
CHEMISTRY; METALLURGY
C09K2211/1014
CHEMISTRY; METALLURGY
H10K85/6574
ELECTRICITY
H10K85/626
ELECTRICITY
H10K85/6572
ELECTRICITY
C07B2200/05
CHEMISTRY; METALLURGY
H10K85/636
ELECTRICITY
H10K85/615
ELECTRICITY
C09K2211/1022
CHEMISTRY; METALLURGY
International classification
C09K11/02
CHEMISTRY; METALLURGY
Abstract
Disclosed herein is an organic light emitting diode (OLED) exhibiting high-efficiency characteristics, and more particularly, an OLED including, as an emission layer material, a compound represented by Chemical Formula 1. The structure of Chemical Formula 1 is as described in the specification.
Claims
1. An organic light-emitting diode including: a first electrode; a second electrode facing the first electrode; and a first emission layer including a first host and a first dopant and a second emission layer including a second host and a second dopant, both layer being interposed between the first electrode and the second electrode, wherein at least one of the first host and the second host includes a compound represented by the following Chemical Formula 1]: ##STR00289## wherein, the substituents R, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, m is an integer of 1 to 9, wherein when m is 2 or more, the corresponding R's are same or different, and when m is 8 or less, the corresponding ##STR00290## moieties are same or different, Z is Si or Ge, the substituents R.sub.1 and R.sub.2, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 1 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, the substituent R.sub.3 is any one selected from a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 10 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, with an exclusion that all of R.sub.1 to R.sub.3 are a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, L.sub.1 and L.sub.2, which are same or different, are each independently a linker selected from a single bond, a substituted or unsubstituted arylene of 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene of 3 to 24 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused arylene of 8 to 24 carbon atoms, wherein the term substituted in the expression a substituted or unsubstituted used for the compounds of Chemical Formula 1 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a 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 heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with at least one hydrogen atom on the substituent being substitutable with a deuterium or tritium atom.
2. The organic light-emitting diode of claim 1, wherein the compound represented by Chemical Formula 1 is a compound represented by the following Chemical Formula 1-1 or 1-2: ##STR00291## wherein, the substituents R are as defined above for R in claim 1, Z.sub.1 and Z.sub.2, which are same or different, are each independently Si or Ge, the substituents R.sub.4, R.sub.5, R.sub.7, and R.sub.8, which are same or different, are each independently as defined above for R.sub.1 and R.sub.2 in claim 1, the substituents R.sub.6 and R.sub.9, which are same or different, are each independently as defined above for R.sub.3 in claim 1, with an exclusion that R.sub.4 to R.sub.6 are all a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, L.sub.3 to L.sub.6, which are same or different, are each independently as defined above for the linkers L.sub.1 and L.sub.2 in claim 1, m1 is 9, wherein the corresponding R are same or different, and m2 is 8, wherein the corresponding R are same or different, wherein the term substituted in the expression substituted or unsubstituted used for the compounds of Chemical Formulas 1-1 and 1-2 is same as defined for the term substituted in the expression substituted or unsubstituted in claim 1.
3. The organic light-emitting diode of claim 2, wherein R in Chemical Formulas 1-1 and 1-2 is any one selected from a hydrogen atom, a deuterium atom, and a substituted or unsubstituted aryl of 6 to 20 carbon atoms.
4. The organic light-emitting diode of claim 3, wherein R in Chemical Formulas 1-1 and 1-2 is a hydrogen atom or a deuterium atom.
5. The organic light-emitting diode of claim 2, wherein R.sub.6 in Chemical Formulas 1-1 and 1-2 is a substituted or unsubstituted alkyl of 1 to 10 carbon atoms.
6. The organic light-emitting diode of claim 2, wherein R.sub.4 and R.sub.5 in Chemical Formulas 1-1 and 1-2, which are same or different, are each independently a substituted or unsubstituted aryl of 6 to 18 carbon atoms.
7. The organic light-emitting diode of claim 2, wherein the compound represented by Chemical Formula 1-1 is a compound represented by the following Chemical Formula 1-1-A: ##STR00292## wherein, the substituents R and R, which are same or different from each other, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 8 to 30 carbon atoms, Z.sub.1 is Si or Ge, the linker L.sub.4 is a single bond or a substituted or unsubstituted arylene of 6 to 24 carbon atoms, the substituent R.sub.5 is a substituted or unsubstituted aryl of 6 to 20 carbon atoms, the substituent R.sub.6 is a substituted or unsubstituted alkyl of 1 to 10 carbon atoms, m1 is 9, wherein the corresponding R are same or different, m3 is 9, wherein the corresponding R are same or different, wherein the term substituted in the expression substituted or unsubstituted used for the compounds of Chemical Formula 1-1-A is same as defined for the term substituted in Chemical Formula 1 of claim 1.
8. The organic light-emitting diode of claim 1, wherein R.sub.1 and R.sub.2 in Chemical Formula 1, which are same or different, are each independently a substituted or unsubstituted aryl of 6 to 30 carbon atoms and R.sub.3 is a substituted or unsubstituted alkyl of 1 to 10 carbon atoms.
9. The organic light-emitting diode of claim 1, wherein the compound represented by Chemical Formula 1 is one selected from the group consisting of the following Compound 1-1 to Compound 1-262: ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367##
10. The organic light-emitting diode of claim 1, wherein one of the first and second hosts within the organic light-emitting diode includes a compound represented by Chemical Formula 1 while the other includes an anthracene compound represented by Chemical Formula 2: ##STR00368## wherein, the substituents R.sub.11 to R.sub.18, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, L.sub.11 and L.sub.12, which are same or different, are each independently any one linker selected from a single bond, a substituted or unsubstituted arylene of 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene of 3 to 24 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused arylene of 8 to 24 carbon atoms, Ar.sub.11 and Ar.sub.12, which are same or different, are each independently any one selected from a substituted or unsubstituted aryl of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to carbon atoms, and a substituted or unsubstituted, aliphatic hydrocarbon ring-fused aryl of 8 to 24 carbon atoms, with the hydrogen atoms bonded to the carbon atoms within Chemical Formula 2 being substitutable with 0 to 60 deuterium atoms or tritium atoms, wherein the term substituted in the expression substituted or unsubstituted used for the compound of Chemical Formula 2 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with one or more hydrogen atoms within the substituents being substitutable with deuterium atoms or tritium atoms.
11. The organic light-emitting diode of claim 10, wherein Ar.sub.12 in the anthracene compound represented by Chemical Formula 2 is a substituent represented by the following Structural Formula 12: ##STR00369## wherein, X is O or S, one of R.sub.21 to R.sub.24 is a single bond to L.sub.12 in Chemical Formula 2, and R.sub.21 to R.sub.28 exclusive of the single bond to L.sub.12 are same or different and are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 1 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, wherein the term substituted in the expression substituted or unsubstituted used for the compound of Chemical Formula 12 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with one or more hydrogen atoms within the substituents being substitutable with deuterium atoms or tritium atoms.
12. The organic light-emitting diode of claim 10, wherein the compound represented by Chemical Formula 2 comprises at least one deuterium atom.
13. The organic light-emitting diode of claim 10, wherein one of the first and second hosts in the organic light-emitting diode comprises two or more different types of the anthracene compound represented by Chemical Formula 2.
14. The organic light-emitting diode of claim 13, wherein the Ar.sub.12 in one or more types of the anthracene compound represented by Chemical Formula 2 is a substituted or unsubstituted aryl of 6 to 30 carbon atoms, and the Ar.sub.12 in one or more types of the additionally included anthracene compound represented by Chemical Formula 2 is a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms.
15. The organic light-emitting diode of claim 14, wherein the Ar.sub.2 in the additionally included anthracene compound represented by Chemical Formula 2 is a substituent represented by the following Structural Formula 12: wherein the Structural Formula is as defined in claim 11.
16. The organic light-emitting diode of claim 10, wherein the first emission layer comprises the compound represented by Chemical Formula 1 as the first host and a host compound different from the compound represented by Chemical Formula 1 at a ratio of 1:9 to 9:1.
17. The organic light-emitting diode of claim 13, wherein the second emission layer comprises, as second hosts, two different types of the anthracene compound represented by Chemical Formula 2 at a ratio of 1:9 to 9:1.
18. The organic light-emitting diode of claim 1, wherein at least one of the first dopant in the first emission layer and the second dopant in the second emission layer comprises one or more types of the polycyclic compound represented by the following Chemical Formula 3: ##STR00370## wherein, Y.sub.1 and Y.sub.2, which are same or different, are each independently any one selected from among O, S, NR.sub.31, CR.sub.32R.sub.33, SiR.sub.34R.sub.35, and GeR.sub.36R.sub.37, A.sub.1 to A.sub.3, which are same or different, are each independently any one selected from among a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring of 5 to 50 carbon atoms, a substituted or unsubstituted, aliphatic hydrocarbon ring-fused aromatic hydrocarbon ring of 8 to 50 carbon atoms, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, and a substituted or unsubstituted, aliphatic hydrocarbon ring-fused heteroaromatic ring of 5 to 50 carbon atoms, R.sub.31 to R.sub.37, which are same or different, are each independently any one selected from among a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted a germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen atom, R.sub.31 to R.sub.37 can be connected to the A.sub.1 to A.sub.3 ring moieties to additionally form an aliphatic or aromatic mono- or polycyclic ring, and a linkage can be made between R.sub.32 and R.sub.33, between R.sub.34 and R.sub.35, and between R.sub.36 and R.sub.37 to additionally form a mono- or polycyclic aliphatic or aromatic ring, wherein the term substituted in the expression substituted or unsubstituted used for the compound of Chemical Formula 3 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroaryl alkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with at least one hydrogen atom on the substituent being substitutable with a deuterium or tritium atom.
19. The organic light-emitting diode of claim 18, wherein the polycyclic ring compound represented by Chemical Formula 3 is a polycyclic compound represented by the following Chemical Formula 3-1 or 3-2: ##STR00371## wherein, X.sub.1 is O or S, Y.sub.1 and Y.sub.2, which are same or different, are each independently any one of O, S, NR.sub.31, CR.sub.32R.sub.33, SiR.sub.34R.sub.35, and GeR.sub.36R.sub.37, A.sub.2 and A.sub.3, which are same or different, are each independently any one selected from a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring of 5 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aromatic hydrocarbon ring of 8 to 50 carbon atoms, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaromatic ring of 5 to 50 carbon atoms, R.sub.31 to R.sub.38, which are same or difference, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, R.sub.31 to R.sub.37 may be linked to A.sub.2 and A.sub.3 ring moieties to form mono- or polycyclic aliphatic or aromatic ring, a linkage may be made between R.sub.32 and R.sub.33, between R.sub.34 and R.sub.35, and between R.sub.36 and R.sub.37 to form respective mono- or polycyclic aliphatic or aromatic rings, o is 4, wherein the corresponding R.sub.38 are same or different, adjacent R.sub.38 substituents may be linked to each other to form a mono- or polycyclic aliphatic or aromatic ring, wherein the term substituted in the expression a substituted or unsubstituted used for the compounds of Chemical Formulas 3-1 and 3-2 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with at least one hydrogen atom on the substituent being substitutable with a deuterium or tritium atom.
20. A pyrene-based compound represented by the following Chemical Formula 1: ##STR00372## wherein, the substituents R, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 1 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, m is an integer of 1 to 9, wherein when m is 2 or more, the corresponding R's are same or different, and when m is 8 or less, the corresponding ##STR00373## moieties are same or different, Z is Si or Ge, the substituents R.sub.1 and R.sub.2, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, the substituent R.sub.3 is any one selected from a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 10 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, with an exclusion that all of R.sub.1 to R.sub.3 are a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, L.sub.1 and L.sub.2, which are same or different, are each independently a linker selected from a single bond, a substituted or unsubstituted arylene of 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene of 3 to 24 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused arylene of 8 to 24 carbon atoms, wherein the term substituted in the expression a substituted or unsubstituted used for the compounds of Chemical Formula 1 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a 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 heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with at least one hydrogen atom on the substituent being substitutable with a deuterium or tritium atom.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
[0031]
DETAILED DESCRIPTION OF THE INVENTION
[0032] Below, a detailed description will be given of the present disclosure. In each drawing of the present disclosure, sizes or scales of components may be enlarged or reduced from their actual sizes or scales for better illustration, and known components may not be depicted therein to clearly show features of the present disclosure. Therefore, the present disclosure is not limited to the drawings. When describing the principle of the embodiments of the present disclosure in detail, details of well-known functions and features may be omitted to avoid unnecessarily obscuring the presented embodiments.
[0033] In the drawing, for convenience of description, sizes of components may be exaggerated for clarity. For example, since sizes and thicknesses of components in drawings are arbitrarily shown for convenience of description, the sizes and thicknesses are not limited thereto. Furthermore, throughout the description, the terms on and over are used to refer to the relative positioning, and mean not only that one component or layer is directly disposed on another component or layer but also that one component or layer is indirectly disposed on another component or layer with a further component or layer being interposed therebetween. Also, spatially relative terms, such as below, beneath, lower, and between may be used herein for ease of description to refer to the relative positioning.
[0034] Throughout the specification, when a portion may include a certain constituent element, unless explicitly described to the contrary, it may not be construed to exclude another constituent element but may be construed to further include other constituent elements. Further, throughout the specification, the word on means positioning on or below the object portion, but does not essentially mean positioning on the lower side of the object portion based on a gravity direction.
[0035] The present disclosure provides an organic light-emitting diode including: a first electrode; a second electrode facing the first electrode; and a first emission layer including a first host and a first dopant and a second emission layer including a second host and a second dopant, both layer being interposed between the first electrode and the second electrode, [0036] wherein at least one of the first host and the second host includes a compound represented by the following Chemical Formula 1]:
##STR00003## [0037] wherein, [0038] the substituents R, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, [0039] m is an integer of 1 to 9, wherein when m is 2 or more, the corresponding R's are same or different, and when m is 8 or less, the corresponding
##STR00004## moieties are same or different, [0040] Z is Si or Ge, [0041] the substituents R.sub.1 and R.sub.2, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, [0042] the substituent R.sub.3 is any one selected from a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted aryl of 10 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, [0043] with an exclusion that all of R.sub.1 to R.sub.3 are a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, [0044] L.sub.1 and L.sub.2, which are same or different, are each independently a linker selected from a single bond, a substituted or unsubstituted arylene of 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene of 3 to 24 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused arylene of 8 to 24 carbon atoms, [0045] wherein the term substituted in the expression substituted or unsubstituted used for the compounds of Chemical Formula 1 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroaryl alkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with at least one hydrogen atom on the substituent being substitutable with a deuterium or tritium atom.
[0046] The expression indicating the number of carbon atoms, such as a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 5 to 50 carbon atoms, etc. means the total number of carbon atoms of, for example, the alkyl or aryl radical or moiety alone, exclusive of the number of carbon atoms of substituents attached thereto. For instance, a phenyl group with a butyl at the para position falls within the scope of an aryl of 6 carbon atoms, even though it is substituted with a butyl radical of 4 carbon atoms.
[0047] As used herein, the term aryl means an organic radical derived from an aromatic hydrocarbon by removing one hydrogen that is bonded to the aromatic hydrocarbon. When the aryl group is substituted, the substituents may be fused with one another to form an additional ring. The aryl group may also include an organic radical obtained by the removal of a single hydrogen atom from an arene ring formed by the fusion of two arene rings.
[0048] Concrete examples of the aryl include aromatic radical groups such as phenyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, and triphenylenyl, but are not limited thereto. The aryl group may also include organic radicals obtained by the removal of one hydrogen atom from a fused arene ring formed by two arene rings, such as a fluorene ring fused with a phenylene ring or a fluorene ring fused with a phenanthrene ring.
[0049] In addition, at least one hydrogen atom on the aryl group may be substituted by a deuterium atom, a halogen atom, a hydroxy, a nitro, a cyano, a silyl, an amino, a germanium, an amidino, a hydrazino, a hydrazone, a carboxyl, a sulfonic acid, a phosphoric acid, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, or an alkyl heteroaryl of 3 to 24 carbon atoms.
[0050] As used herein, the term aromatic hydrocarbon ring refers to an aromatic ring composed of carbon and hydrogen atoms and the term aliphatic hydrocarbon ring refers to a hydrocarbon ring that is composed of carbon and hydrogen atoms, but does not belong to the aromatic hydrocarbon rings. Particularly, the aliphatic hydrocarbon ring may have a bonding structure of the sp.sup.3 orbital for at least 30% of the carbon atoms as ring members, with 0 to 3 double and/or triple bonds within the ring. More particularly, the aliphatic hydrocarbon ring may have a bonding structure of the sp.sup.3 orbital for at least 50% of the carbon atoms as ring members, with 0 to 2 double and/or triple bonds within the ring.
[0051] As used herein, the term aliphatic hydrocarbon ring-fused aryl refers to a cyclic substituent having overall non-aromaticity, in which two adjacent carbon atoms of the aliphatic hydrocarbon ring are fused with two adjacent carbon atoms of the aryl ring, exclusive of the carbon atom that becomes an organic radical by removal of a hydrogen atom, to form a shared double bond. Specific examples include tetrahydronaphthyl, tetrahydrobenzocycloheptene, tetrahydrophenanthrenyl, tetrahydroanthracenyl, octahydrotriphenylenyl, and the like, but are not limited thereto.
[0052] The substituent heteroaryl, used in the compound of the present disclosure, means a hetero aromatic radical of 2 to 24 carbon atoms, bearing as ring member(s) one to three heteroatoms selected from among N, O, P, Si, S, Ge, Se, and Te. In the aromatic radical, two or more rings may be fused. One or more hydrogen atoms on the heteroaryl may be substituted by the same substituents as on the aryl.
[0053] Concrete examples of the heteroaryl include thiophenyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, carbazolyl, acenaphthoquinoxalinyl, indenoquinazolinyl, indenoisoquinolinyl, indenoquinolinyl, pyridoindolyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzofuranyl, benzothiophenyl, benzoselenophenyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophenyl, phenanthrolinyl, thiazolinyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenoxazinyl, phenothiazinyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzoselenophenyl, indolocarbazolyl, and the like, but are not limited thereto.
[0054] In addition, the term heteroaromatic ring, as used herein, refers to an aromatic hydrocarbon ring bearing at least one heteroatom as an aromatic ring member. In the heteroaromatic ring, one to three carbon atoms of the aromatic hydrocarbon may be substituted by at least one selected particularly from N, O, P, Si, S, Ge, Se, and Te.
[0055] As used herein, the term aliphatic hydrocarbon ring-fused heteroaryl refers to the same cyclic substituent as in the aliphatic hydrocarbon ring-fused aryl, with the exception that a heteroaryl, instead of an aryl, is substituted. Specific examples include, but are not limited to, tetrahydroindole, tetrahydrobenzofuranyl, tetrahydrobenzothiophene, tetrahydrocarbazole, tetrahydrodibenzofuranyl, tetrahydrobenzothiophene, tetrahydroquinoline, and tetrahydroquinoxaline.
[0056] As used herein, the term fused ring in which an aromatic hydrocarbon ring is fused with an aliphatic hydrocarbon ring means a fused ring in which an aromatic hydrocarbon ring has two adjacent carbon atoms in common with an aliphatic hydrocarbon ring, as exemplified by a tetrahydronaphthalene ring in which the benzene ring shares two adjacent carbon atoms with the cyclohexane ring and dihydroindene ring.
[0057] In addition, the fused ring of a heteroaromatic ring and an aliphatic hydrocarbon ring, as used herein, refers to a fused ring in which a heteroaromatic ring has two adjacent carbon atoms in common with an aliphatic hydrocarbon ring, as exemplified by hexahydrodibenzofuran ring in which the benzofuran ring shares two adjacent carbon atoms with the cyclohexane ring.
[0058] As used herein, the term alkyl refers to an alkane missing one hydrogen atom and includes linear or branched structures. Examples of the alkyl substituent useful in the present disclosure include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto. At least one hydrogen atom of the alkyl may be substituted by the same substituent as in the aryl.
[0059] As used herein, the term halogenated alkyl refers to an alkyl with at least one hydrogen atom substituted by a halogen. Preferably, the halogen may be a fluorine atom.
[0060] The term cyclo as used in substituents of the compounds of the present disclosure, such as cycloalkyl, cycloalkoxy, etc., refers to a structure responsible for a mono- or polycyclic ring of saturated hydrocarbons within an alkyl radical, an alkoxy radical, etc. Concrete examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, and so on. One or more hydrogen atoms on the cycloalkyl may be substituted by the same substituents as on the aryl. This is true of the cycloalkoxy.
[0061] In the present disclosure, the term heterocycloalkyl refers to a cycloalkyl with at least one heteroatom substituted as a ring member for a carbon atom within the ring. Preferably, one to three carbon atoms within the ring may be substituted by at least one selected from N, O, P, S, Si, Ge, Se, and Te.
[0062] In addition, the term aromatic hydrocarbon ring- or heteroaromatic ring-fused cycloalkyl refers to a cyclic substituent having overall non-aromaticity, in which two adjacent carbon atoms of the aromatic hydrocarbon ring or heteroaromatic ring are fused with two adjacent carbon atoms of the cycloalkyl ring, exclusive of the carbon atom that becomes an organic radical by removal of a hydrogen atom, to form a shared double bond. Specific examples include tetrahydronaphthyl, tetrahydrophenanthrene, tetrahydroquinoline, tetrahydroquinoxaline, cyclopentabenzofuran, and the like, but are not limited thereto.
[0063] Furthermore, the term aromatic hydrocarbon ring-fused heterocycloalkyl has the same meaning as the aromatic hydrocarbon ring-fused cycloalkyl, except for the cycloalkyl ring moiety having at least one heteroatom as a ring member, with non-aromaticity across the molecule thereof. Preferably, one to three carbon atoms within the cycloalkyl ring moiety are substituted by at least one heteroatom selected from among N, O, P, S, Si, Ge, Se, and Te. Specific examples include hexahydrodibenzofuranyl, hexahydrocarbazole, hexahydrodibenzothiophene, and dihydrobenzodioxin, but are not limited thereto.
[0064] As used herein, the heteroaliphatic ring-fused aryl or heteroaryl is same as the aliphatic hydrocarbon ring-fused aryl or heteroaryl, except for a heteroaliphatic ring substituted for the aliphatic hydrocarbon ring, with non-aromaticity across the molecule thereof. Concrete examples include cromane, dihydropyranopyridine, thiocromane, dihydrobenzodioxine, dihydrothiopyranopyridine, and dihydropyranopyrimidine.
[0065] The term heteroaliphatic ring refers to an aliphatic hydrocarbon bearing at least one heteroatom as a ring member. Preferably, one to three carbon atoms within an aliphatic hydrocarbon are substituted by at least one heteroatom selected from N, O, and S.
[0066] The term alkoxy, as used in the compounds of the present disclosure, refers to an alkyl or cycloalkyl singularly bonded to oxygen. Concrete examples of the alkoxy include methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, iso-amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantyloxy, dicyclopentyloxy, bornyloxy, isobornyloxy, and the like, but are not limited thereto. One or more hydrogen atoms on the alkoxy may be substituted by the same substituents as on the aryl.
[0067] Concrete examples of the arylalkyl used in the compounds of the present disclosure include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, and the like, but are not limited thereto. One or more hydrogen atoms on the arylalkyl may be substituted by the same substituents as on the aryl.
[0068] Concrete examples of the alkylaryl used in the compound of the present disclosure include tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, and t-butylphenanthryl, but are not limited thereto. One or more hydrogen atoms on the alkylaryl may be substituted by the same substituents as on the aryl.
[0069] As used herein, the term alkenyl refers to an alkyl substituent containing a carbon-carbon double bond between two carbon atoms and the term alkynyl refers to an alkyl substituent containing a carbon-carbon triple bond between two carbon atoms.
[0070] As used herein, the term alkylene refers to an organic radical regarded as derived from an alkane by removal two hydrogen atoms from one carbon atom for methylene or different carbon atoms for ethylene or higher, such as propylene, isopropylene, isobutylene, sec-butylene, tert-butylene, pentylene, iso-amylene, hexylene, and the like, but with no limitations thereto. One or more hydrogen atoms on the alkylene may be substituted by the same substituents as on the aryl.
[0071] In the present disclosure, the term amine refers to a functional group including NH.sub.2, in which one or two of the hydrogen atoms in NH.sub.2 are substituted by any one selected from among alkyl, cycloalkyl, aryl, aliphatic hydrocarbon ring-fused aryl, arylalkyl, alkylaryl, heteroaryl, and aliphatic hydrocarbon ring-fused heteroaryl. When both the hydrogen atoms bonded to the nitrogen atom in NH.sub.2 are substituted by the foregoing substituents, they may be same or different. One or more hydrogen atoms on the alkyl, cycloalkyl, aryl, aliphatic hydrocarbon ring-fused aryl, arylalkyl, alkylaryl, heteroaryl, or aliphatic hydrocarbon ring-fused heteroaryl may be substituted by the same substituents as on the aryl.
[0072] Each of the aryl radicals in the aryl, arylheteroaryl, aliphatic hydrocarbon ring-fused aryl, and cycloalkylaryl bonded to the nitrogen atom in the amine may be a monocyclic or polycyclic one. Each of the heteroaryl radicals in the heteroarylamine, and arylheteroarylamine may be a mono- or polycyclic one.
[0073] Examples of the amine include an alkylamine in which one or two alkyl radicals, which are same or different, are bonded to the nitrogen atom; an arylamine in which one or two aryl radicals, which are same or different, are bonded to the nitrogen atom; and an alkylaryl amine in which one alkyl radical and one aryl radical are bonded to the nitrogen atom. In addition, heteroaryl amine, aryl heteroaryl amine, alkyl (aliphatic hydrocarbon ring-fused aryl) amine, aryl (aliphatic hydrocarbon-fused aryl) amine, cycloalkyl (aliphatic hydrocarbon ring-fused aryl)amine, cycloalkyl arylamine, heteroaryl (aliphatic hydrocarbon ring-fused aryl) amine are also exemplified.
[0074] The silyl used in the compounds of the present disclosure refers to a functional group based on SiH3 in which at least one of the three hydrogen atoms bonded to the silicon atom is substituted by any one selected from among alkyl, cycloalkyl, aryl, aliphatic hydrocarbon ring-fused aryl, arylalkyl, alkylaryl, heteroaryl, aliphatic hydrocarbon ring-fused heteroaryl. Two or three substituents, when used to substitute two or three hydrogen atoms bonded to the silicon atom in SiH3, may be same or different. One or more hydrogen atoms on the alkyl, cycloalkyl, aryl, aliphatic hydrocarbon ring-fused aryl, aryl alkyl, alkyl aryl, heteroaryl, and aliphatic hydrocarbon ring-fused heteroaryl may be substituted by the same substituents as on the aryl.
[0075] Here, each of the aryl radicals in the aryl, aryl heteroaryl, aliphatic hydrocarbon ring-fused aryl, cycloalkyl aryl, etc. which are bonded to the silicon atom in the silyl may be a mono- or polycyclic aryl. Also, each of the heteroaryl radicals in the heteroaryl, aryl heteroaryl, etc. may be mono- or polycyclic heteroaryl.
[0076] Examples of the silyl include alkylsilyl in which one or two or three same or different alkyl radicals are bonded to the silicon atom, arylsilyl in which one or two or three same or different aryl radicals are bonded to the silicon atom, alkylaryl silyl in which one alkyl radical and one aryl radical are bonded to the silicon atom, and alkylaryl heteroaryl silyl in which one alkyl radical, one aryl radical, and one heteroaryl radical are bonded to the silicon atom. In addition, alkyl(heteroaryl)silyl, arylheteroarylsilyl, alkyl(aliphatic hydrocarbon ring-fused aryl)silyl, alkyl(aryl) (aliphatic hydrocarbon ring-fused aryl)silyl, cycloalkyl(aliphatic hydrocarbon ring-fused aryl)silyl, cycloalkyl arylheteroarylsilyl, and alkyl(heteroaryl) (aliphatic hydrocarbon ring-fused aryl)silyl may be exemplified.
[0077] Furthermore, specific examples of the silyl include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfurylsilyl.
[0078] As used herein, the term germanium (or germyl or germane) can be accounted for by the definitions for silyl radicals, with the exception that the silicon atom (Si) in the silyl radical is substituted by a germanium atom (Ge).
[0079] Concrete examples of the germanium radical include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, and dimethylfurylgermane. One or more hydrogen atoms on the germanium radical may be substituted by the same substituents as on the aryl.
[0080] As used herein, the substituent (B) adjacent to a substituent (A) within an aromatic ring means a substituent (B) bonded to a carbon atom(s) as a ring member(s) adjacent to a carbon atom as a ring member having the substituent (A) bonded thereto, within the aromatic ring. Also, the substituent (B) adjacent to a substituent (A) within an aliphatic ring means a substituent (B) bonded to a carbon atom(s) as a ring member(s) adjacent to a carbon atom as a ring member having the substituent (A) bonded thereto, within the aliphatic ring. Further, the substituent (B) adjacent to a substituent (A) within an aliphatic chain structure means a substituent (B) bonded to a carbon atom(s) as a ring member(s) adjacent to a carbon atom as a ring member having the substituent (A) bonded thereto, within the aliphatic chain structure.
[0081] As used herein, the term alkenyl refers to an alkyl substituent containing a carbon-carbon double bond between two carbon atoms and the term alkynyl refers to an alkyl substituent containing a carbon-carbon triple bond between two carbon atoms.
[0082] As used herein, the term alkylene refers to an organic radical regarded as derived from an alkane by removal two hydrogen atoms from one carbon atom for methylene or different carbon atoms for ethylene or higher, such as propylene, isopropylene, isobutylene, sec-butylene, tert-butylene, pentylene, iso-amylene, hexylene, and the like, but with no limitations thereto. One or more hydrogen atoms on the alkylene may be substituted by the same substituents as on the aryl.
[0083] In a preferable embodiment, the substituent accounted for by the term substituted in the expression substituted or unsubstituted used for compounds of Chemical Formula 1 may be at least one selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 12 carbon atoms, a halogenated alkyl of 1 to 12 carbon atoms, an alkenyl of 2 to 12 carbon atoms, an alkynyl of 2 to 12 carbon atoms, a cycloalkyl of 3 to 12 carbon atoms, a heteroalkyl of 1 to 12 carbon atoms, an aryl of 6 to 18 carbon atoms, an arylalkyl of 7 to 20 carbon atoms, an alkylaryl of 7 to 20 carbon atoms, a heteroaryl of 2 to 18 carbon atoms, a heteroarylalkyl of 3 to 18 carbon atoms, an alkyl heteroaryl of 3 to 18 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 9 to 20 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 7 to 20 carbon atoms, an aromatic hydrocarbon ring-fused heterocycloalkyl of 9 to 20 carbon atoms, an aliphatic hydrocarbon ring-fused aryl of 9 to 20 carbon atoms, an aliphatic hydrocarbon ring-fused heteroaryl of 7 to 20 carbon atoms, an alkoxy of 1 to 12 carbon atoms, an amine of 1 to 18 carbon atoms, a silyl of 1 to 18 carbon atoms, a germanium of 1 to 18 carbon atoms, an aryloxy of 6 to 18 carbon atoms, and an arylthionyl of 6 to 18 carbon atoms. The substituent may have a deuterium or tritium atom, instead of at least one hydrogen atom, bonded thereto.
[0084] In a more preferable embodiment of the present disclosure, the substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms may be a substituted or unsubstituted aromatic hydrocarbon ring-fused cycloalkyl of 9 to 20 carbon atoms.
[0085] In a more preferable embodiment of the present disclosure, the substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms may be a substituted or unsubstituted heteroaromatic ring-fused cycloalkyl of 7 to 20 carbon atoms.
[0086] In a more preferable embodiment of the present disclosure, the substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 6 to 30 carbon atoms may be a substituted or unsubstituted aromatic hydrocarbon ring-fused heterocycloalkyl of 9 to 20 carbon atoms.
[0087] In a more preferable embodiment of the present disclosure, the substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 8 to 30 carbon atoms may be a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 9 to 20 carbon atoms.
[0088] In a more preferable embodiment of the present disclosure, the substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 5 to 30 carbon atoms may be a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaryl of 7 to 20 carbon atoms.
[0089] In a more preferable embodiment of the present disclosure, the substituted or unsubstituted heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms may be a substituted or unsubstituted heteroaliphatic ring-fused aryl of 7 to 20 carbon atoms.
[0090] In a more preferable embodiment of the present disclosure, the substituted or unsubstituted heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms may be a substituted or unsubstituted heteroaliphatic ring-fused heteroaryl of 6 to 20 carbon atoms.
[0091] As used herein, the expression R.sub.31 to R.sub.37 may be linked to the A.sub.1 to A.sub.3 ring moieties to additionally form a mono- or polycyclic aliphatic or aromatic ring means that each substituent selected from R.sub.31 to R.sub.37 (i.e., each of the R.sub.31 to R.sub.37 substituents) may form an additional ring by removing one hydrogen radical from the substituent and one hydrogen radical from each of the rings A.sub.1 to A.sub.3 for the purpose of forming a mono- or polycyclic aliphatic or aromatic ring, and then linking them together. Likewise, in the expression a linkage may be made between R.sub.32 and R.sub.33, between R.sub.34 and R.sub.35, and between R.sub.36 and R.sub.37 to additionally form a mono- or polycyclic aliphatic or aromatic ring, when, for example, R.sub.32 and R.sub.33 form a ring, it means that one hydrogen radical is removed from R.sub.32 and one hydrogen radical is removed from R.sub.33, and the two are then connected to additionally form a ring.
[0092] As a material for at least one emission layer in the organic light-emitting diode including a plurality of emission layers according to the present disclosure, the compound represented by Chemical Formula 1 is used, wherein the compound represented by Chemical Formula 1 includes at least one silane or germanium group within the pyrene ring. Through the structure represented by Chemical Formula 1, it was found that, compared to the case where all substituents of the silane group are phenyl groups, replacing one of the substituents with a structure such as naphthalene having 10 or more carbon atoms results in a decrease in the triplet energy level. This configuration satisfies two key conditions: the triplet energy level is (1) lower than that of the dopant in one of the emission layers of the OLED, and (2) higher than that of the host in the other emission layer. As a result, it becomes possible to realize an OLED exhibiting high efficiency and long lifetime characteristics compared to conventional OLEDs.
[0093] Furthermore, the compound represented by Chemical Formula 1 that is used as a material in the emission layer of the organic light-emitting diode according to the present disclosure may be a compound represented by the following Chemical Formula 1-1 or 1-2:
##STR00005## [0094] wherein, [0095] the substituents R are as defined above for R, Z.sub.1 and Z.sub.2, which are same or different, are each independently Si or Ge, [0096] the substituents R.sub.4, R.sub.5, R.sub.7, and R.sub.8, which are same or different, are each independently as defined above for R.sub.1 and R.sub.2, [0097] the substituents R.sub.6 and R.sub.9, which are same or different, are each independently as defined above for R.sub.3, [0098] with an exclusion that R.sub.4 to R.sub.6 are all a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, [0099] L.sub.3 to L.sub.6, which are same or different, are each independently as defined above for the linkers L.sub.1 and L.sub.2, [0100] m1 is 9, wherein the corresponding R are same or different, and [0101] m2 is 8, wherein the corresponding R are same or different, [0102] wherein the term substituted in the expression substituted or unsubstituted used for the compounds of Chemical Formulas 1-1 and 1-2 is same as defined for the term substituted in the expression substituted or unsubstituted in the foregoing.
[0103] According to an embodiment, R.sub.1 and R.sub.2 in Chemical Formula 1, which are same or different, are each independently at least one selected from a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 8 to 30 carbon atoms, and a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms.
[0104] According to an embodiment, R.sub.3 in Chemical Formula 1 is any one selected from a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 10 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 8 to 30 carbon atoms, and a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms.
[0105] According to an embodiment, R's in Chemical Formulas 1-1 and 1-2, which are same or different, are each independently at least one selected from a hydrogen atom, a deuterium atom, and a substituted or unsubstituted aryl of 6 to 20 carbon atoms, with more preference for a hydrogen atom or a deuterium atom.
[0106] According to an embodiment, R.sub.6 in Chemical Formulas 1-1 and 1-2 may be a substituted or unsubstituted alkyl of 1 to 10 carbon atoms.
[0107] According to an embodiment, R.sub.4 and R.sub.5 in Chemical Formulas 1-1 and 1-2, which are same or different, are each independently a substituted or unsubstituted aryl of 6 to 18 carbon atoms.
[0108] According to an embodiment, at least one of R.sub.4 and R.sub.5 in Chemical Formulas 1-1 and 1-2 may be a substituted or unsubstituted aryl of 16 to 30 carbon atoms.
[0109] According to an embodiment, the compound represented by Chemical Formula 1-1 may be preferably a compound represented by the following Chemical Formula 1-1-A:
##STR00006## [0110] wherein, [0111] the substituents R and R, which are same or different from each other, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused aryl of 8 to 30 carbon atoms, [0112] Z.sub.1 is Si or Ge, [0113] the linker L.sub.4 is a single bond or a substituted or unsubstituted arylene of 6 to 24 carbon atoms, [0114] the substituent R.sub.5 is a substituted or unsubstituted aryl of 6 to 20 carbon atoms, the substituent R.sub.6 is a substituted or unsubstituted alkyl of 1 to 10 carbon atoms, [0115] m1 is 9, wherein the corresponding R are same or different, [0116] m3 is 9, wherein the corresponding R are same or different, [0117] wherein the term substituted in the expression substituted or unsubstituted used for the compounds of Chemical Formula 1-1-A is same as defined for the term substituted in Chemical Formula 1.
[0118] In an embodiment, R.sub.1 and R.sub.2 in the compound represented by Chemical Formula 1, which are same or different, are each independently any one selected from a substituted or unsubstituted alkyl of 1 to 10 carbon atoms, a substituted or unsubstituted aryl of 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms, and R.sub.3 is a substituted or unsubstituted aryl of 10 to 30 carbon atoms or a substituted or unsubstituted alkyl of 1 to 10 carbon atoms.
[0119] According to an embodiment, R.sub.1 and R.sub.2 in the compound represented by Chemical Formula 1, which are same or different from each other, may each be independently a substituted or unsubstituted aryl of 6 to 30 carbon atoms, and R.sub.3 may be a substituted or unsubstituted alkyl of 1 to 10 carbon atoms.
[0120] According an embodiment, concrete examples of the compound represented by Chemical Formula 1 include the following Compounds 1-1 to 1-267:
##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026##
##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050##
##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069##
##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##
[0121] Throughout the description of the present disclosure, the phrase (organic layer or emission layer) includes at least one organic compound may be construed to mean that (organic layer) may include a single organic compound species or two or more different species of organic compounds falling within the scope of the present disclosure.
[0122] In the organic light-emitting diode according to the present disclosure, the compound represented by Chemical Formula 1 may be used as a host in the first or second emission layer. That is, the OLED according to the present disclosure may include one or more of the compounds represented by Chemical Formula 1 as a host material in the emission layer.
[0123] In an embodiment, of the first and the second host within the organic light-emitting diode according to the present disclosure, one may include a compound represented by Chemical Formula 1 while the other may include an anthracene compound represented by Chemical Formula 2. For instance, the first host within the organic light-emitting diode according to the present disclosure may include a compound represented by Chemical Formula 1 while the second host may include an anthracene compound represented by Chemical Formula 2, and vice versa.
##STR00084## [0124] wherein, [0125] the substituents R.sub.11 to R.sub.18, which are same or different, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 1 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, [0126] L.sub.11 and L.sub.12, which are same or different, are each independently any one linker selected from a single bond, a substituted or unsubstituted arylene of 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene of 3 to 24 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused arylene of 8 to 24 carbon atoms, [0127] Ar.sub.11 and Ar.sub.12, which are same or different, are each independently any one selected from a substituted or unsubstituted aryl of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, and a substituted or unsubstituted, aliphatic hydrocarbon ring-fused aryl of 8 to 24 carbon atoms, [0128] with the hydrogen atoms bonded to the carbon atoms within Chemical Formula 2 being substitutable with 0 to 60 deuterium atoms or tritium atoms, [0129] wherein the term substituted in the expression substituted or unsubstituted used for the compound of Chemical Formula 2 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with one or more hydrogen atoms within the substituents being substitutable with deuterium atoms or tritium atoms.
[0130] In an embodiment, R.sub.11 to R.sub.18 within Chemical Formula 2, which are same or different, are each independently any one selected from a hydrogen atom or a deuterium atom.
[0131] In an embodiment, the compound represented by Chemical Formula 2 may contain at least one deuterium atom.
[0132] When the first host or the second host in the organic light-emitting diode of the present disclosure contains at least one of the anthracene compounds represented by Chemical Formula 2, Ar.sub.12 in the anthracene compound represented by Chemical Formula 2 may be a substituent represented by the following Structural Formula 12:
##STR00085## [0133] wherein, [0134] X is O or S, [0135] one of R.sub.21 to R.sub.24 is a single bond to Liz in Chemical Formula 2, with preference for R.sub.21 or R.sub.22 being a single bond to L.sub.12, and [0136] R.sub.21 to R.sub.28 exclusive of the single bond to Liz are same or different and are each independently as defined for R.sub.11 to R.sub.18 in Chemical Formula 2.
[0137] In an embodiment, R.sub.21 to R.sub.28 in Structural Formula 12 may be any one selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, and a substituted or unsubstituted, aliphatic hydrocarbon ring-fused aryl of 8 to 24 carbon atoms, [0138] wherein the term substituted in the expression substituted or unsubstituted used for the compound of Chemical Formula 12 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 heteroaliphatic ring-fused aryl of 6 to 30 carbon atoms, a heteroaliphatic ring-fused heteroaryl of 5 to 30 carbon atoms, an amine of 1 to 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with one or more hydrogen atoms within the substituents being substitutable with deuterium atoms or tritium atoms.
[0139] In an embodiment, X in Structural Formula 12 may be 0.
[0140] In an embodiment, one of the first host and second host within the organic light-emitting diode according to the present disclosure may contain a compound represented by Chemical Formula 1 while the other may contain two or more types of the anthracene compounds represented by Chemical Formula 2. In this regard, the anthracene compounds represented by Chemical Formula 2 may be different anthracene compounds. For instance, the first host within the organic light-emitting diode according to the present disclosure may include the compound represented by Chemical Formula 1 and the second host may include two or more types of the anthracene compounds represented by Chemical Formula 2, and vice versa. In this regard, the compound represented by Chemical Formula 2 may be anthracene compounds different from each other.
[0141] In an embodiment, when one of the first host and the second host within the organic light-emitting diode according to the present disclosure contains two types of the anthracene compounds represented by Chemical Formula 2, the Ar.sub.12 radical may be a substituted or unsubstituted aryl of 6 to 30 carbon atoms in at least one of the anthracene compounds represented by Chemical Formula 2, and in addition, the Ar.sub.12 radical may be a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms in at least one of the additionally used anthracene compounds represented by Chemical Formula 2.
[0142] In an embodiment, when one of the first host and the second host within the organic light-emitting diode according to the present disclosure includes two types of the anthracene compounds represented by Chemical Formula 2, the Ar.sub.12 radical in at least one of the anthracene compounds represented by Chemical Formula 2 may be a substituted or unsubstituted aryl of 6 to 30 carbon atoms, and in addition, the Ar.sub.12 radical in at least one of the additionally used anthracene compounds represented by Chemical Formula 2 may be a substituent represented by Structural Formula 12.
[0143] In an embodiment, the first emission layer within the organic light-emitting diode according to the present disclosure may contain at least one of the compounds represented by Chemical Formula 1 as the first host while the second emission layer may contain at least one of the compounds represented by Chemical Formula 2 as the second host.
[0144] In an embodiment, when one of the first host and the second host within the organic light-emitting diode according to the present disclosure includes two types of the compounds represented by Chemical Formula 1 while the other includes an anthracene compound represented by Chemical Formula 2, the first emission layer may contain the compound represented by Chemical Formula 1 as the first host and a host compound different from the compound represented by Chemical Formula 1 at a ratio of 1:9 to 9:1 and more preferably at a ratio of 3:7 to 7:3.
[0145] In cases where the first host is comprised of two or more compounds, these compounds may be mixed and deposited, co-deposited, or laminated for use. That is, the first host according to the present disclosure may comprise, in addition to one compound represented by Chemical Formula 1, one or more additional compounds that differ therefrom, such that two or more first host compounds may be mixed and deposited, co-deposited, or laminated. In the case of lamination, a compound different from that represented by Chemical Formula 1 may be laminated above or below the layer comprising the compound of Chemical Formula 1.
[0146] Here, when the compound different from that of Chemical Formula 1 is deposited in a mixed state, it means that the compounds are mixed in a single deposition source and deposited by sublimation or vaporization. In the case of co-deposition, it means that two or more hosts are respectively sublimated or vaporized from multiple deposition sources and simultaneously deposited.
[0147] That is, the emission layer may be formed by depositing a thin film using multiple host materials respectively from different deposition sources (co-deposition), or by depositing a pre-mixed host blend, or by forming the emission layer via a lamination method.
[0148] Here, the host compound different from that represented by Chemical Formula 1 may be a compound with a structure different from that of Chemical Formula 1, or a compound that, while still falling within the structure category of Chemical Formula 1, is distinct from a previously used compound (i.e., not identical to the compound already used).
[0149] As one embodiment, examples of compounds having a structure different from that of Chemical Formula 1 for use in the first emission layer include conventionally known anthracene-based compounds, benzanthracene-based compounds, phenanthrene-based compounds, pyrene-based compounds, fluorene-based compounds, spiro-fluorene-based compounds, chrysene-based compounds, carbazole-based compounds, and biphenyl-based compounds. Among these, the anthracene-based compounds refer to compounds that contain at least one, preferably 1 to 3 anthracene groups within the molecule. The remaining types, that is, benzanthracene-based compounds, phenanthrene-based compounds, pyrene-based compounds, fluorene-based compounds, spiro-fluorene-based compounds, chrysene-based compounds, carbazole-based compounds, and biphenyl-based compounds likewise refer to compounds containing at least one, preferably 1 to 3 groups of the respective type within the molecule.
[0150] In an embodiment, when one of the first or second hosts in the OLED according to the present disclosure includes the compound represented by Chemical Formula 1, and the other includes an anthracene compound represented by Chemical Formula 2, the other host (i.e., the one not including Chemical Formula 1) may include two or more different anthracene compounds represented by Chemical Formula 2 preferably at a ratio of 1:9 to 9:1 and more preferably at a ratio of 3:7 to 7:3.
[0151] In an embodiment, the first emission layer of the OLED according to the present disclosure may include one or more compounds represented by Chemical Formula 1 as the first host and the second emission layer may include one or more compounds represented by Chemical Formula 2 as the second host. In this regard, the second emission layer may further comprise, in addition to the compound represented by Chemical Formula 2, a host compound different from that of Chemical Formula 2. The second host used in the second emission layer may include two different anthracene compounds represented by Chemical Formula 2 at a ratio of 1:9 to 9:1 and more preferably at a ratio of 3:7 to 7:3.
[0152] When the second host comprises two or more compounds, they may be mixed in a single deposition source and deposited by sublimation or vaporization, or each may be sublimated or vaporized from separate deposition sources and co-deposited onto the second emission layer.
[0153] Here, the host compound different from that of Chemical Formula 2 may be a compound having a structure different from that of Chemical Formula 2, or a compound that, although classified within the same structural group as Chemical Formula 2, is distinct from any compound already used.
[0154] Further, compounds having a structure different from Chemical Formula 2 for use in the second emission layer may include conventionally known anthracene-based compounds, benzanthracene-based compounds, phenanthrene-based compounds, pyrene-based compounds, fluorene-based compounds, spiro-fluorene-based compounds, chrysene-based compounds, carbazole-based compounds, and biphenyl-based compounds, the descriptions of which are the same as previously stated.
[0155] In an embodiment, the first host in the first emission layer of the OLED according to the present disclosure, may consist solely of a compound represented by Chemical Formula 1, and the second host in the second emission layer may include a compound represented by Chemical Formula 2 and a compound different therefrom at a ratio of 1:9 to 9:1 and more preferably 3:7 to 7:3.
[0156] In an embodiment, the first host in the first emission layer of the OLED according to the present disclosure may include a compound represented by Chemical Formula 1 and a compound different therefrom at a ratio of 1:9 to 9:1 and more preferably 3:7 to 7:3, and the second host in the second emission layer may consist solely of a compound represented by Chemical Formula 2.
[0157] In yet another embodiment, the first host in the first emission layer may include the compound represented by Chemical Formula 1 and a different compound at a ratio of 1:9 to 9:1 and more preferably 3:7 to 7:3, and the second host in the second emission layer may include the compound represented by Chemical Formula 2 and a different compound at a ratio of 1:9 to 9:1 and more preferably 3:7 to 7:3.
[0158] In an embodiment, concrete examples of the compound represented by Chemical Formula 2 include, but are not limited to:
##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119##
##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147##
##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171##
##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193##
[0159] In one embodiment, the organic layer in the OLED of the present disclosure may further include at least one layer selected from a hole injection layer, a hole transport layer, a functional layer capable of both hole injection and hole transport, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer between the first electrode and the second electrode.
[0160] In an embodiment, the OLED according to the present disclosure may include at least one of a hole transport layer and a hole injection layer between the first electrode and the emission layer, and may include at least one of an electron transport layer and an electron injection layer between the emission layer and the second electrode.
[0161] In an embodiment of the organic light-emitting diode according to the present disclosure, the first emission layer may include a first host and a first dopant and the second emission layer may include a second host and a second dopant. In this regard, at least one of the first dopant in the first emission layer and the second dopant in the second emission layer may contain at least one polycyclic compound represented by the following Chemical Formula 3. Preferably, the first dopant in the first emission layer and the second dopant in the second emission layer, which may be same or different, may both contain at least one polycyclic compound represented by Chemical Formula 3:
##STR00194## [0162] wherein, [0163] Y.sub.1 and Y.sub.2, which are same or different, are each independently any one selected from among O, S, NR.sub.31, CR.sub.32R.sub.33, SiR.sub.34R.sub.35, and GeR.sub.36R.sub.37, [0164] A.sub.1 to A.sub.3, which are same or different, are each independently any one selected from among a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring of 5 to 50 carbon atoms, a substituted or unsubstituted, aliphatic hydrocarbon ring-fused aromatic hydrocarbon ring of 8 to 50 carbon atoms, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, and a substituted or unsubstituted, aliphatic hydrocarbon ring-fused heteroaromatic ring of 5 to 50 carbon atoms, [0165] R.sub.31 to R.sub.37, which are same or different, are each independently any one selected from among a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted a germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen atom, [0166] R.sub.31 to R.sub.37 may be connected to the A.sub.1 to A.sub.3 ring moieties to additionally form an aliphatic or aromatic mono- or polycyclic ring, and [0167] linkage may be made between R.sub.32 and R.sub.33, between R.sub.34 and R.sub.35, and between R.sub.36 and R.sub.37 to additionally form a mono- or polycyclic aliphatic or aromatic ring, [0168] wherein the term substituted in the expression substituted or unsubstituted used for the compound of Chemical Formula 3 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, a halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroaryl alkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with at least one hydrogen atom on the substituent being substitutable with a deuterium or tritium atom.
[0169] In a more preferred embodiment of the present disclosure, A.sub.1 to A.sub.3 may be the same or different, and each may independently be a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 30 carbon atoms, or a substituted or unsubstituted, aliphatic hydrocarbon ring-fused aromatic hydrocarbon ring of 8 to 50 carbon atoms.
[0170] In an embodiment, the first dopant in the first emission layer and the second dopant in the second emission layer may both be the same compound and contain at least one polycyclic compound represented by Chemical Formula 3.
[0171] In addition, when the first dopant or second dopant within the OLED according to the present disclosure contains one or more types of the polycyclic compound represented by Chemical Formula 3, the polycyclic compound represented by Chemical Formula 3 may be a polycyclic compound represented by the following Chemical Formula 3-1 or 3-2. Preferably, both the first dopant in the first emission layer and the second dopant in the second emission layer may be a polycyclic ring compound represented by Chemical Formula 3-1 or 3-2:
##STR00195## [0172] wherein, [0173] X.sub.1 is O or S, [0174] Y.sub.1 and Y.sub.2, which are same or different, are each independently any one of O, S, NR.sub.31, CR.sub.32R.sub.33, SiR.sub.34R.sub.35, and GeR.sub.36R.sub.37, [0175] A.sub.2 and A.sub.3, which are same or different, are each independently any one selected from a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring of 5 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring-fused aromatic hydrocarbon ring of 8 to 50 carbon atoms, a substituted or unsubstituted heteroaromatic ring of 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic hydrocarbon ring-fused heteroaromatic ring of 5 to 50 carbon atoms, [0176] R.sub.31 to R.sub.38, which are same or difference, are each independently any one selected from a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl 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 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl of 2 to 50 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 8 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 cycloalkyloxy of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy of 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio of 1 to 30 carbon atoms, a substituted or unsubstituted arylthio of 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylthio of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio of 2 to 30 carbon atoms, a substituted or unsubstituted amine of 0 to 40 carbon atoms, a substituted or unsubstituted silyl of 0 to 40 carbon atoms, a substituted or unsubstituted germanium of 0 to 40 carbon atoms, a nitro, a cyano, and a halogen, [0177] R.sub.31 to R.sub.37 may be linked to A.sub.2 and A.sub.3 ring moieties to form mono- or polycyclic aliphatic or aromatic ring, [0178] a linkage may be made between R.sub.32 and R.sub.33, between R.sub.34 and R.sub.35, and between R.sub.36 and R.sub.37 to form respective mono- or polycyclic aliphatic or aromatic rings, [0179] o is 4, wherein the corresponding R.sub.38 are same or different, [0180] adjacent R.sub.38 substituents may be linked to each other to form a mono- or polycyclic aliphatic or aromatic ring, [0181] wherein the term substituted in the expression a substituted or unsubstituted used for the compounds of Chemical Formulas 3-1 and 3-2 means having at least one substituent selected from the group consisting of a deuterium atom, a tritium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 30 carbon atoms, halogenated alkyl of 1 to 30 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a cycloalkyl of 3 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 3 to 24 carbon atoms, an alkyl heteroaryl of 3 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, aromatic hydrocarbon ring-fused cycloalkyl of 7 to 30 carbon atoms, a heteroaromatic ring-fused cycloalkyl of 5 to 30 carbon atoms, an 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 30 carbon atoms, a silyl of 1 to 30 carbon atoms, a germanium of 1 to 30 carbon atoms, an aryloxy of 6 to 24 carbon atoms, and an arylthionyl of 6 to 24 carbon atoms, with at least one hydrogen atom on the substituent being substitutable with a deuterium or tritium atom.
[0182] In an embodiment, concrete examples of the compound represented by Chemical Formula 3 include, but are not limited to:
##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212##
[0183] Below, with reference to the drawing, a description will be given of the organic light-emitting diode of the present disclosure.
[0184] FIGURE is a schematic view illustrating the structure of an organic light-emitting diode according to an embodiment of the present disclosure.
[0185] As shown in FIGURE, the organic light-emitting diode according to an embodiment of the present disclosure comprises an anode (20), a hole transport layer (40), a first emission layer (50), a second emission layer (50) containing a host and a dopant, an electron transport layer (60), and a cathode (80), wherein the anode and the cathode serve as a first electrode and a second electrode, respectively, with the interposition of the hole transport layer between the anode and the light emission layer, and the electron transport layer between the emission layer and the cathode.
[0186] Furthermore, the organic light-emitting diode according to an embodiment of the present disclosure may include a hole injection layer (30) between the anode (20) and the hole transport layer (40), and an electron injection layer (70) between the electron transport layer (60) and the cathode (80).
[0187] Reference is made to FIGURE with regard to the organic light-emitting diode of the present disclosure and the fabrication thereof.
[0188] First, a substrate (10) is coated with an anode electrode material to form an anode (20). So long as it is used in a typical organic electroluminescence (EL) device, any substrate may be used as the substrate (10). Preferable is an organic substrate or transparent plastic substrate that exhibits excellent transparency, surface smoothness, ease of handling, and waterproofness. As the anode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO), which are transparent and superior in terms of conductivity, may be used.
[0189] A hole injection layer material is applied on the anode (20) by thermal deposition in a vacuum or by spin coating to form a hole injection layer (30). Subsequently, thermal deposition in a vacuum or by spin coating may also be conducted to form a hole transport layer (40) with a hole transport layer material on the hole injection layer (30).
[0190] So long as it is typically used in the art, any material may be selected for the hole injection layer (30) without particular limitations thereto. Examples include, but are not limited to, 2-TNATA [4,4, 4-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N-di(1-naphthyl)-N,N-diphenylbenzidine)], TPD [N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine], DNTPD [N,N-diphenyl-N,N-bis-[4-(phenyl-m-tolylamino)-phenyl]-biphenyl-4,4-diamine] HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile].
[0191] Any material that is typically used in the art may be selected for the hole transport layer (40) without particular limitations thereto. Examples include, but are not limited to, N,N-bis(3-methylphenyl)-N,N-diphenyl-[1,1-biphenyl]-4,4-diamine (TPD) or N,N-di(naphthalen-1-yl)-N,N-diphenylbenzidine (a-NPD), N-[[1,1-biphenyl]-4-yl]-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl) phenyl]-9H-fluorene-2-amine (BCFN), and the like.
[0192] In an embodiment of the present disclosure, an electron blocking layer may be additionally disposed on the hole transport layer. Functioning to prevent the electrons injected from the electron injection layer from entering the hole transport layer from the emission layer, the electron blocking layer is adapted to increase the life span and luminous efficiency of the diode. The electron blocking layer may be formed of a well-known material or a combination of well-known materials, as necessary, at a suitable position between the emission layer and the hole injection layer. Particularly, the electron blocking layer may be formed between the emission layer and the hole transport layer.
[0193] Next, the first emission layer (50) and the second emission layer (50) may each be deposited or co-deposited on the hole transport layer (40) by deposition in a vacuum or by spin coating.
[0194] Here, the compound represented by Chemical Formula 1 or Chemical Formula 2 may be used as a host material in the first or second emission layer of the OLED while the compound represented by Chemical Formula 3 may be used as a dopant material in the the first or second emission layer of the the OLED. The materials constituting these layers are as previously described.
[0195] In addition, as a method for forming the emission layer, a thin film may be formed by depositing (co-depositing) multiple or a single type of first host material and a dopant material from separate deposition sources, or, alternatively, the plurality of host materials (for example, the first host material and the second host material) may be pre-mixed and co-deposited with the dopant from different deposition sources.
[0196] Here, when each host is co-deposited separately from multiple deposition sources, although the manufacturing process becomes more complex, it has the advantage that the thin film can be formed without prior contact between the respective materials, thereby preventing degradation of device characteristics that may result from interactions between heterogeneous compounds when pre-mixed in a single deposition source. On the other hand, pre-mixing the materials allows for simplification of the manufacturing equipment and process.
[0197] According to a specific embodiment of the present disclosure, the thickness of the first emission layer (50) and the second emission layer (50) may range from 30 to 200 preferably, may range from 50 to 150 .
[0198] The electron transport layer (60) may be deposited on the emitting layer by vacuum deposition or spin coating.
[0199] In the present disclosure, the electron transport layer (60) functions to stably transport electrons injected from the electron-injecting electrode (cathode), and known electron transport materials may be used. Examples of such known materials include quinoline derivatives, particularly tris(8-quinolinolato)aluminum (Alq3), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-olate) (Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, and BND, but are not limited thereto:
##STR00213## ##STR00214##
[0200] In the organic light-emitting diode of the present disclosure, an electron injection layer (EIL) that functions to facilitate electron injection from the cathode may be formed on the electron transport layer. The material for the EIL is not particularly limited.
[0201] Any material that is conventionally used in the art can be available for the electron injection layer (70) without particular limitations. Examples include CsF, NaF, LiF, Li2O, and BaO. Deposition conditions for the electron injection layer may vary, depending on compounds used, but may be generally selected from condition scopes that are almost the same as for the formation of hole injection layers.
[0202] The electron injection layer (70) may range in thickness from about 1 to about 100 , and particularly from about 3 to about 90 . Given the thickness range for the electron injection layer, the diode can exhibit satisfactory electron injection properties without actually elevating a driving voltage.
[0203] In order to facilitate electron injection, the cathode (80) may be made of a material having a small work function, such as metal or metal alloy such as lithium (Li), magnesium (Mg), calcium (Ca), an alloy aluminum (Al) thereof, aluminum-lithium (AlLi), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). Alternatively, ITO or IZO may be employed to form a transparent cathode for an organic light-emitting diode.
[0204] Moreover, the organic light-emitting diode of the present disclosure may further comprise an emission layer containing a blue, green, or red luminescent material that emits radiations in the wavelength range of 380 nm to 800 nm. That is, the emission layer in the present disclosure has a multi-layer structure wherein the blue, green, or red luminescent material may be a fluorescent material or a phosphorescent material.
[0205] Furthermore, at least one selected from among the layers may be deposited using a single-molecule deposition process or a solution process.
[0206] Here, the deposition process is a process by which a material is vaporized in a vacuum or at a low pressure and deposited to form a layer, and the solution process is a method in which a material is dissolved in a solvent and applied for the formation of a thin film by means of inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc.
[0207] Also, the organic light-emitting diode of the present disclosure may be applied to a device selected from among flat display devices; flexible display devices; stretchable display devices; monochrome or grayscale flat illumination devices; monochrome or grayscale flexible illumination devices; vehicle or aircraft display devices, and display devices for virtual or augmented reality.
[0208] A better understanding of the present disclosure may be obtained through the following examples which are set forth to illustrate, but are not to be construed as limiting the present disclosure.
EXAMPLES
Synthesis Example 1. Synthesis of [Compound 1-6]
Synthesis Example 1-1. Synthesis of A-1
##STR00215##
[0209] In a round-bottom flask, <A-1b> (30 g) in THF (300 mL) was chilled to 78 C. under a nitrogen condition and then added slowly with drops of 1.6M n-butyl lithium (100.1 mL) before stirring for one hour. <A-1a> (14 g) was slowly added, followed by stirring at 78 C. for one hour and at room temperature for 12 hours. After completion of the reaction, the reaction mixture was concentrated at a reduced pressure and diluted with heptane. Subsequent to removal of lithium chloride by filtration, vacuum concentration afforded <A-1>. (22.22 g, 85%) Synthesis Example 1-2. Synthesis of [Compound 1-6]
##STR00216##
[0210] In a round-bottom flask, <A-2a> (19 g) in THF (225 mL) was chilled to 78 C. under a nitrogen condition and then added slowly with drops of 1.6M n-butyl lithium (46.4 mL) before stirring for one hour. A dilution of <A-1> (22.2 g) in THF (66.6 mL) was slowly added and then stirred at 78 C. for 1 hour and at room temperature for 12 hours. After completion of the reaction, the reaction mixture was subjected to extraction with water. The organic layer thus formed was concentrated in a vacuum, followed by isolation through column chromatography to afford [Compound 1-6]. (23.35 g, 74%)
[0211] MS (MALDI-TOF): m/z 560.20 [M.sup.+]
Synthesis Example 2. Synthesis of [Compound 1-14]
Synthesis Example 2-1. Synthesis of B-1
##STR00217##
[0212] <B-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1a> and <B-1b> instead of <A-1a> and <A-1b>, respectively. (yield 55%)
Synthesis Example 2-2. Synthesis of B-2
##STR00218##
[0213] <B-2> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1> and <B-2a> instead of <A-1a> and <A-1b>, respectively. (yield 64%)
Synthesis Example 2-3. Synthesis of [Compound 1-14]
##STR00219##
[0214] [Compound 1-14] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <B-2> and <B-3a> instead of <A-1> and <A-2a>, respectively. (yield 52%)
[0215] MS (MALDI-TOF): m/z 507.24 [M.sup.+]
Synthesis Example 3. Synthesis of [Compound 1-22]
Synthesis Example 3-1. Synthesis of C-1
##STR00220##
[0216] <C-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1a> and <B-2a> instead of <A-1a> and <A-1b>, respectively. (yield 63%)
Synthesis Example 3-2. Synthesis of [Compound 1-22]
##STR00221##
[0217] [Compound 1-22] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <C-1> instead of <A-1>. (yield 54%)
[0218] MS (MALDI-TOF): m/z 598.21 [M.sup.+]
Synthesis Example 4. Synthesis of [Compound 1-28]
Synthesis Example 4-1. Synthesis of D-1
##STR00222##
[0219] <D-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1> and <D-1a> instead of <A-1a> and <A-1b>, respectively. (yield 58%)
Synthesis Example 4-2. Synthesis of [Compound 1-28]
##STR00223##
[0220] [Compound 1-28] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <D-1> instead of <A-1>. (yield 54%)
[0221] MS (MALDI-TOF): m/z 548.20 [M.sup.+]
Synthesis Example 5. Synthesis of [Compound 1-31]
Synthesis Example 5-1. Synthesis of E-1
##STR00224##
[0222] In a round-bottom flask, <E-1a> (50 g) in THF (500 mL) was chilled to 78 C. under a nitrogen condition and then added slowly with drops of 1.6M n-butyl lithium (158 mL) before stirring for 1 hour. Trimethylborate (30.5 mL) was slowly added in a dropwise manner and stirred at room temperature for 12 hours. Addition of 1N HCl (aq) was followed by stirring for 10 minutes. After layer separation, the organic layer was washed many times with water and treated with MgSO.sub.4. Recrystallization in heptane afforded <E-1>. (34 g, 80%)
Synthesis Example 5-2. E-2
##STR00225##
[0223] In a round-bottom flask, a mixture of <E-1> (31.42 g), <E-2a> (40 g), Pd(PPh3).sub.4 (4.91 g), K.sub.2CO.sub.3 (48.85 g), 1,4-dioxane (400 mL), and water (146.56 mL) was stirred for 12 hours under reflux in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was subjected to extraction with water and treated with MgSO.sub.4. Isolation by column chromatography afforded <E-2>. (31.9 g, 72%)
Synthesis Example 5-3. Synthesis of E-3
##STR00226##
[0224] <E-3> was synthesized in the same manner as in Synthesis Example 5-1, with the exception of using <E-2> instead of <E-1a> (yield 82%)
Synthesis Example 5-4. Synthesis of E-4
##STR00227##
[0225] <E-4> was synthesized in the same manner as in Synthesis Example 5-2, with the exception of using <E-3> and <E-4a> instead of <E-1> and <E-2a>, respectively. (yield 76%)
Synthesis Example 5-5. Synthesis of E-5
##STR00228##
[0226] In a round-bottom flask, <E-4> (30 g) in dichloromethane (300 mL) was cooled to 0 C. under a nitrogen condition. Thereafter, boron tribromide (10.97 mL) was slowly added in a dropwise manner and stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was subjected to extraction with water and treated with MgSO.sub.4. Subsequent isolation by column chromatography afforded <E-5>. (26 g, 90%)
Synthesis Example 5-6. Synthesis of E-6
##STR00229##
[0227] In a round-bottom flask, <E-5> (26 g) and pyridine (8.2 g) in dichloromethane (260 mL) was chilled to 10 C. under a nitrogen condition and added slowly with drops of trifluoromethanesulfonic anhydride before stirring at room temperature for 12 hours. After completion of the reaction, the reaction mixture was subjected to extraction with water and treated with MgSO.sub.4. Subsequent isolation by column chromatography afforded <E-6>. (24.6 g, 70%)
Synthesis Example 5-7. Synthesis of E-7
##STR00230##
[0228] In a round-bottom flask, a mixture of <E-6> 24.6 g, Pd(OAc).sub.2 (0.54 g), Sphos (1 g), and KOAc (14.3 g) in dimethylacetamide (246 mL) was stirred at 100 C. for 12 hours under a nitrogen condition. After completion of the reaction, the reaction mixture was subjected to extraction with water and treated with MgSO.sub.4. Subsequent isolation by column chromatography afforded <E-7>. (17 g, 98%)
Synthesis Example 5-8. Synthesis of E-8
##STR00231##
[0229] <E-8> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1> and <E-7> instead of <A-1a> and <A-1b>, respectively. (yield 63%)
Synthesis Example 5-9. Synthesis of [Compound 1-31]
##STR00232##
[0230] [Compound 1-31] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <E-8> instead of <A-1>. (yield 66%)
[0231] MS (MALDI-TOF): m/z 598.21 [M.sup.+]
Synthesis Example 6. Synthesis of [Compound 1-39]
Synthesis Example 6-1. Synthesis of F-1
##STR00233##
[0232] <F-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1a> and <F-1a> instead of <A-1a> and <A-1b>, respectively. (yield 67%)
Synthesis Example 6-2. Synthesis of [Compound 1-39]
##STR00234##
[0233] [Compound 1-39] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <F-1> instead of <A-1>. (yield 67%)
[0234] MS (MALDI-TOF): m/z 572.20 [M.sup.+]
Synthesis Example 7. Synthesis of [Compound 1-38]
Synthesis Example 7-1. Synthesis of [Compound 1-38]
##STR00235##
[0235] [Compound 1-38] was synthesized in the same manner as in Synthesis Example 6-2, with the exception of using <B-1> and <B-3a> instead of <F-1> and <A-2a>, respectively. (yield 69%)
[0236] MS (MALDI-TOF): m/z 540.29 [M.sup.+]
Synthesis Example 8. Synthesis of [Compound 1-41]
Synthesis Example 8-1. Synthesis of G-1
##STR00236##
[0237] <G-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <G-1a> instead of <A-1b>. (yield 71%)
Synthesis Example 8-2. Synthesis of [Compound 1-41]
##STR00237##
[0238] [Compound 1-41] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <G-1> instead of <A-1>. (yield 69%)
[0239] MS (MALDI-TOF): m/z 660.23 [M.sup.+]
Synthesis Example 9. Synthesis of [Compound 1-56]
Synthesis Example 9-1. Synthesis of [Compound 1-56]
##STR00238##
[0240] [Compound 1-56] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <A-1a> instead of <A-1>. (yield 63%)
[0241] MS (MALDI-TOF): m/z 708.23 [M.sup.+]
Synthesis Example 10. Synthesis of [Compound 1-61]
Synthesis Example 10-1. Synthesis of H-1
##STR00239##
[0242] <H-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1a> and <D-1a> instead of <A-1a> and <A-1b>, respectively. (yield 54%)
Synthesis Example 10-2. Synthesis of [Compound 1-61]
##STR00240##
[0243] [Compound 1-61] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <H-1> instead of <A-1>. (yield 66%)
[0244] MS (MALDI-TOF): m/z 672.23 [M.sup.+]
Synthesis Example 11. Synthesis of [Compound 1-62]
Synthesis Example 11-1. Synthesis of I-1
##STR00241##
[0245] <I-1> was synthesized in the same manner as in Synthesis Example 5-2, with the exception of using <E-3> and <I-1a> instead of <E-1> and <E-2a>, respectively. (yield 74%)
Synthesis Example 11-2. Synthesis of I-2
##STR00242##
[0246] <I-2> was synthesized in the same manner as in Synthesis Example 5-5, with the exception of using <I-1> instead of <E-4>. (yield 92%)
Synthesis Example 11-3. Synthesis of I-3
##STR00243##
[0247] <I-3> was synthesized in the same manner as in Synthesis Example 5-6, with the exception of using <I-2> instead of <E-5>. (yield 97%)
Synthesis Example 11-4. Synthesis of I-4
##STR00244##
[0248] <I-4> was synthesized in the same manner as in Synthesis Example 5-7, with the exception of using <I-3> instead of <E-6>. (yield 96%)
Synthesis Example 11-5. Synthesis of I-5
##STR00245##
[0249] <I-5> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <I-4> instead of <A-1b>. (yield 59%)
Synthesis Example 11-6. Synthesis of [Compound 1-62]
##STR00246##
[0250] [Compound 1-62] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <I-5> instead of <A-1>. (yield 66%)
[0251] MS (MALDI-TOF): m/z 784.26 [M.sup.+]
Synthesis Example 12. Synthesis of [Compound 1-73]
Synthesis Example 12-1. Synthesis of J-1
##STR00247##
[0252] <J-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <J-1a> and <J-1b> instead of <A-1a> and <A-1b>, respectively. (yield 62%)
Synthesis Example 12-2. Synthesis of J-2
##STR00248##
[0253] <J-2> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <J-1> and <J-2a> instead of <A-1a> and <A-1b>, respectively. (yield 63%)
Synthesis Example 12-3. Synthesis of [Compound 1-73]
##STR00249##
[0254] [Compound 1-73] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <J-2> instead of <A-1>. (yield 64%)
[0255] MS (MALDI-TOF): m/z 684.39 [M.sup.+]
Synthesis Example 13. Synthesis of [Compound 1-78]
Synthesis Example 13-1. Synthesis of K-1
##STR00250##
[0256] <K-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <J-1a> and <B-1b> instead of <A-1a> and <A-1b>, respectively. (yield 54%)
Synthesis Example 13-2. Synthesis of K-2
##STR00251##
[0257] <K-2> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <K-1> and <K-2a> instead of <A-1a> and <A-1b>, respectively. (yield 67%)
Synthesis Example 13-3. Synthesis of [Compound 1-78]
##STR00252##
[0258] [Compound 1-78] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <K-2> instead of <A-1>. (yield 53%)
[0259] MS (MALDI-TOF): m/z 550.18 [M.sup.+]
Synthesis Example 14. Synthesis of [Compound 1-90]
Synthesis Example 14-1. Synthesis of L-1
##STR00253##
[0260] <L-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <L-1a> instead of <A-1b>. (yield 61%)
Synthesis Example 14-2. Synthesis of L-2
##STR00254##
[0261] <L-2> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <L-1> instead of <A-1a>. (yield 55%)
Synthesis Example 14-3. Synthesis of [Compound 1-90]
##STR00255##
[0262] [Compound 1-90] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <L-2> instead of <A-1>. (yield 60%)
[0263] MS (MALDI-TOF): m/z 675.24 [M.sup.+]
Synthesis Example 15. Synthesis of [Compound 1-91]
Synthesis Example 15-1. Synthesis of M-1
##STR00256##
[0264] <M-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <K-2a> instead of <A-1b>. (yield 57%)
Synthesis Example 15-2. Synthesis of [Compound 1-91]
##STR00257##
[0265] [Compound 1-91] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <M-1> instead of <A-1>. (yield 44%)
[0266] MS (MALDI-TOF): m/z 640.19 [M.sup.+]
Synthesis Example 16. Synthesis of [Compound 1-105]
Synthesis Example 16-1. Synthesis of N-1
##STR00258##
[0267] <N-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <B-1a> and <N-1a> instead of <A-1a> and <A-1b>, respectively. (yield 57%)
Synthesis Example 16-2. Synthesis of [Compound 1-105]
##STR00259##
[0268] [Compound 1-105] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <N-1> instead of <A-1>. (yield 65%)
[0269] MS (MALDI-TOF): m/z 685.22 [M.sup.+]
Synthesis Example 17. Synthesis of [Compound 1-123]
Synthesis Example 17-1. Synthesis of 0-1
##STR00260##
[0270] <O-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <K-1> instead of <A-1a>. (yield 75%)
Synthesis Example 17-2. Synthesis of [Compound 1-123]
##STR00261##
[0271] [Compound 1-123] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <O-1> and <O-2a> instead of <A-1> and <A-2a>, respectively. (yield 49%)
[0272] MS (MALDI-TOF): m/z 818.28 [M.sup.+]
Synthesis Example 18. Synthesis of [Compound 1-134]
Synthesis Example 18-1. Synthesis of [Compound 1-134]
##STR00262##
[0273] [Compound 1-134] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <P-1a> and <O-2a> instead of <A-1> and <A-2a>, respectively. (yield 50%)
[0274] MS (MALDI-TOF): m/z 842.28 [M.sup.+]
Synthesis Example 19. Synthesis of [Compound 1-151]
Synthesis Example 19-1. Synthesis of Q-1
##STR00263##
[0275] <Q-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <Q-1a> and <G-1a> instead of <A-1a> and <A-1b>, respectively. (yield 71%)
Synthesis Example 19-2. Synthesis of Q-2
##STR00264##
[0276] <Q-2> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <Q-1> and <J-2a> instead of <A-1a> and <A-1b>, respectively. (yield 71%)
Synthesis Example 19-3. Synthesis of [Compound 1-151]
##STR00265##
[0277] [Compound 1-151] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <Q-2> instead of <A-1>. (yield 69%)
[0278] MS (MALDI-TOF): m/z 630.23 [M.sup.+]
Synthesis Example 20. Synthesis of [Compound 1-154]
Synthesis Example 20-1. Synthesis of R-1
##STR00266##
[0279] <R-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <R-1a> and <R-1b> instead of <A-1a> and <A-1b>, respectively. (yield 50%)
Synthesis Example 20-2. Synthesis of R-2
##STR00267##
[0280] <R-2> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <R-1> and <R-2a> instead of <A-1a> and <A-1b>, respectively. (yield 50%)
Synthesis Example 20-3. Synthesis of [Compound 1-154]
##STR00268##
[0281] [Compound 1-154] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <R-2> instead of <A-1>. (yield 61%)
[0282] MS (MALDI-TOF): m/z 660.19 [M.sup.+]
Synthesis Example 21. Synthesis of [Compound 1-155]
Synthesis Example 21-1. Synthesis of S-1
##STR00269##
[0283] <S-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <Q-1a> and <S-1a> instead of <A-1a> and <A-1b>, respectively. (yield 50%)
Synthesis Example 21-2. Synthesis of [Compound 1-155]
##STR00270##
[0284] [Compound 1-155] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <S-1> instead of <A-1>. (yield 61%)
[0285] MS (MALDI-TOF): m/z 656.07 [M.sup.+]
Synthesis Example 22. Synthesis of [Compound 1-156]
Synthesis Example 22-1. Synthesis of T-1
##STR00271##
[0286] <T-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <Q-1a> and <J-2a> instead of <A-1a> and <A-1b>, respectively. (yield 50%)
Synthesis Example 22-2. Synthesis of [Compound 1-156]
##STR00272##
[0287] [Compound 1-156] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <T-1> instead of <A-1>. (yield 61%)
[0288] MS (MALDI-TOF): m/z 664.31 [M.sup.+]
Synthesis Example 23. Synthesis of [Compound 1-169]
Synthesis Example 23-1. Synthesis of U-1
##STR00273##
[0289] <U-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <U-1a> and <U-1b> instead of <A-1a> and <A-1b>, respectively. (yield 75%)
Synthesis Example 23-2. Synthesis of [Compound 1-169]
##STR00274##
[0290] [Compound 1-169] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <U-1> and <O-2a> instead of <A-1> and <A-2a>, respectively. (yield 49%)
[0291] MS (MALDI-TOF): m/z 1004.25 [M.sup.+]
Synthesis Example 24. Synthesis of [Compound 1-170]
Synthesis Example 24-1. Synthesis of V-1
##STR00275##
[0292] <V-1> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <V-1a> and <V-1b> instead of <A-1a> and <A-1b>, respectively. (yield 75%)
Synthesis Example 24-2. Synthesis of <V-2>
##STR00276##
[0293] <V-2> was synthesized in the same manner as in Synthesis Example 1-1, with the exception of using <V-1> and <V-2a> instead of <A-1a> and <A-1b>, respectively. (yield 75%)
Synthesis Example 24-3. Synthesis of [Compound 1-170]
##STR00277##
[0294] [Compound 1-170] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <V-2> and <O-2a> instead of <A-1> and <A-2a>, respectively. (yield 49%)
[0295] MS (MALDI-TOF): m/z 1160.55 [M.sup.+]
Synthesis Example 25. Synthesis of [Compound 1-192]
Synthesis Example 25-1. Synthesis of W-1
##STR00278##
[0296] <W-1> was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <P-1a> and <O-2a> instead of <A-1> and <A-2a>, respectively. (yield 50%)
Synthesis Example 25-2. Synthesis of [Compound 1-192]
##STR00279##
[0297] [Compound 1-192] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <W-2a> and <W-1> instead of <A-1> and <A-2a>, respectively. (yield 65%)
[0298] MS (MALDI-TOF): m/z 780.27 [M.sup.+]
Synthesis Example 26. Synthesis of [Compound 1-206]
Synthesis Example 26-1. Synthesis of [Compound 1-206]
##STR00280##
[0299] [Compound 1-206] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <B-1> and <X-1a> instead of <A-1> and <A-2a>, respectively. (yield 63%)
[0300] MS (MALDI-TOF): m/z 674.24 [M.sup.+]
Synthesis Example 27. Synthesis of [Compound 1-208]
Synthesis Example 27-1. Synthesis of [Compound 1-208]
##STR00281##
[0301] [Compound 1-208] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <B-1> and <Y-1a> instead of <A-1> and <A-2a>, respectively. (yield 63%)
[0302] MS (MALDI-TOF): m/z 674.24 [M.sup.+]
Synthesis Example 28. Synthesis of [Compound 1-243]
Synthesis Example 28-1. Synthesis of [Compound 1-243]
##STR00282##
[0303] [Compound 1-243] was synthesized in the same manner as in Synthesis Example 1-2, with the exception of using <B-1> and <Z-1a> instead of <A-1> and <A-2a>, respectively. (yield 77%)
[0304] MS (MALDI-TOF): m/z 674.24 [M.sup.+]
Examples 1 TO 52: Fabrication of Organic Light-Emitting Diodes Including 1.SUP.st .and 2.SUP.nd .Emission Layers
[0305] An ITO glass substrate was patterned to have a translucent area of 2 mm2 mm and cleansed. The ITO glass was mounted in a vacuum chamber that was then set to have a base pressure of 110.sup.7 torr. On the ITO glass substrate, HAT-CN (700 ) and -NPD (300 ) were sequentially deposited to form a hole injection layer and hole transport layer, respectively. Then, a first emission layer and a second emission layer were sequentially formed as emission layers, wherein the first emission layer was established by forming a film (50 ) from a combination of a pyrene compound represented by Chemical Formula 1 according to the present disclosure and a polycyclic compound (1 wt %) selected from the following [BD-1] to [BD-3] and the second emission layer was established by forming a film (150 ) from a combination of an anthracene compound represented by [BH-1] or [BH-2] and a polycyclic compound (1 wt %) selected from the following [BD-1] to [BD-3]. Thereafter, films were formed from a mixture of 1:1 of [E-1] and [E-2] for an electron transport layer (300 ), [E-2] for an electron injection layer (10 ), and A1 (1000 ) for a cathode in the order, thereby fabricating an organic light-emitting diode. The organic light-emitting diodes thus obtained were measured at 0.4 mA for luminescence properties:
##STR00283## ##STR00284## ##STR00285##
Comparative Examples 1 to 19
[0306] Organic light-emitting diodes for the Comparative Examples were fabricated in the same manner as in the Examples, with the exception of using a polycyclic compound selected from the following [RH-1] to [RH-4] instead of the compounds according to the present disclosure. The OLEDs thus obtained were measured at 0.4 mA for luminescence properties. Here, the structures of [RH-1] to [RH-4] are as follows:
##STR00286##
TABLE-US-00001 TABLE 1 1.sup.st Emission 2.sup.nd Emission Driving layer layer Volt Lifetime Example Host Dopant Host Dopant (V) EQE (%) (LT97, hr) Ex. 1 1-6 BD-2 BH-1 BD-2 3.3 13.2 311 Ex. 2 1-14 BD-2 BH-1 BD-2 3.2 12.9 320 Ex. 3 1-22 BD-2 BH-1 BD-2 3.3 13.0 303 Ex. 4 1-28 BD-2 BH-1 BD-2 3.2 13.2 314 Ex. 5 1-31 BD-2 BH-1 BD-2 3.4 13.2 315 Ex. 6 1-38 BD-2 BH-1 BD-2 3.5 13.2 320 Ex. 7 1-39 BD-2 BH-1 BD-2 3.4 13.4 320 Ex. 8 1-41 BD-2 BH-1 BD-2 3.4 13.5 328 Ex. 9 1-56 BD-2 BH-1 BD-2 3.6 13.5 323 Ex. 10 1-61 BD-2 BH-1 BD-2 3.5 13.5 321 Ex. 11 1-62 BD-2 BH-1 BD-2 3.6 13.5 322 Ex. 12 1-73 BD-2 BH-1 BD-2 3.5 13.3 325 Ex. 13 1-78 BD-2 BH-1 BD-2 3.4 13.2 315 Ex. 14 1-90 BD-2 BH-1 BD-2 3.4 13.1 317 Ex. 15 1-91 BD-2 BH-1 BD-2 3.4 13.2 318 Ex. 16 1-105 BD-2 BH-1 BD-2 3.7 13.3 314 Ex. 17 1-123 BD-2 BH-1 BD-2 3.6 13.5 324 Ex. 18 1-134 BD-2 BH-1 BD-2 3.8 13.7 320 Ex. 19 1-151 BD-2 BH-1 BD-2 3.4 13.1 295 Ex. 20 1-154 BD-2 BH-1 BD-2 3.5 13.1 293 Ex. 21 1-155 BD-2 BH-1 BD-2 3.5 13.2 299 Ex. 22 1-156 BD-2 BH-1 BD-2 3.4 13.1 292 Ex. 23 1-169 BD-2 BH-1 BD-2 3.7 13.3 308 Ex. 24 1-170 BD-2 BH-1 BD-2 3.7 13.3 313 Ex. 25 1-192 BD-2 BH-1 BD-2 3.6 13.6 321 Ex. 26 1-197 BD-2 BH-1 BD-2 3.3 13.2 302 Ex. 27 1-198 BD-2 BH-1 BD-2 3.6 13.4 307 Ex. 28 1-199 BD-2 BH-1 BD-2 3.4 13.0 313 Ex. 29 1-206 BD-2 BH-1 BD-2 3.3 13.1 324 Ex. 30 1-208 BD-2 BH-1 BD-2 3.3 13.2 325 Ex. 31 1-243 BD-2 BH-1 BD-2 3.4 13.1 326 Ex. 32 1-6 BD-2 BH-2 BD-2 3.2 13.3 321 Ex. 33 1-41 BD-2 BH-2 BD-2 3.3 13.6 338 Ex. 34 1-56 BD-2 BH-2 BD-2 3.5 13.6 333 Ex. 35 1-123 BD-2 BH-2 BD-2 3.5 13.4 334 Ex. 36 1-151 BD-2 BH-2 BD-2 3.3 13.2 305 Ex. 37 1-169 BD-2 BH-2 BD-2 3.6 13.4 318 Ex. 38 1-6 BD-1 BH-2 BD-1 3.2 13.0 301 Ex. 39 1-41 BD-1 BH-2 BD-1 3.3 13.3 318 Ex. 40 1-56 BD-1 BH-2 BD-1 3.5 13.3 313 Ex. 41 1-123 BD-1 BH-2 BD-1 3.5 13.1 314 Ex. 42 1-151 BD-1 BH-2 BD-1 3.3 12.9 285 Ex. 43 1-169 BD-1 BH-2 BD-1 3.6 13.1 298 Ex. 44 1-6 BD-3 BH-2 BD-3 3.3 13.3 331 Ex. 45 1-41 BD-3 BH-2 BD-3 3.4 13.6 348 Ex. 46 1-56 BD-3 BH-2 BD-3 3.6 13.6 343 Ex. 47 1-123 BD-3 BH-2 BD-3 3.6 13.4 344 Ex. 48 1-151 BD-3 BH-2 BD-3 3.4 13.2 315 Ex. 49 1-169 BD-3 BH-2 BD-3 3.7 13.4 328 Ex. 50 1-206 BD-3 BH-2 BD-3 3.3 13.2 314 Ex. 51 1-208 BD-3 BH-2 BD-3 3.2 13.3 315 Ex. 52 1-243 BD-3 BH-2 BD-3 3.3 13.2 316 C. Ex. 1 RH-1 BD-1 BH-1 BD-1 4.0 10.2 110 C. Ex. 2 RH-1 BD-2 BH-1 BD-2 4.0 10.5 130 C. Ex. 3 RH-1 BD-1 BH-2 BD-1 3.9 10.3 120 C. Ex. 4 RH-1 BD-3 BH-2 BD-3 4.0 10.6 150 C. Ex. 5 RH-2 BD-2 BH-2 BD-2 3.9 10.0 140 C. Ex. 6 RH-2 BD-3 BH-2 BD-3 4.0 10.0 150 C. Ex. 7 RH-2 BD-1 BH-1 BD-1 4.0 9.6 110 C. Ex. 8 RH-3 BD-1 BH-2 BD-1 4.0 10.5 180 C. Ex. 9 RH-3 BD-2 BH-2 BD-2 4.0 10.9 200 C. Ex. 10 RH-3 BD-3 BH-1 BD-3 4.2 10.8 200 C. Ex. 11 RH-4 BD-1 BH-1 BD-1 4.1 10.4 144 C. Ex. 12 RH-4 BD-2 BH-1 BD-2 4.3 10.9 161 C. Ex. 13 RH-4 BD-2 BH-2 BD-2 4.2 10.8 184 C. Ex. 14 1-156 BD-1 4.3 9.3 7 C. Ex. 15 1-192 BD-1 4.5 9.5 8 C. Ex. 16 1-6 BD-2 4.4 9.6 8 C. Ex. 17 1-123 BD-2 4.6 9.8 9 C. Ex. 18 1-41 BD-3 4.5 9.4 11 C. Ex. 19 1-56 BD-3 4.5 9.5 10
[0307] As shown in Table 1, it was confirmed that the organic light-emitting diode (OLED) comprising the compounds according to the present disclosure in the first emission layer and the second emission layer exhibited high efficiency and long lifetime characteristics, with improved luminous efficiency and device lifetime at lower driving voltages, in comparison to the OLEDs using comparative compounds according to conventional technologies (Comparative Examples 1 to 13).
[0308] In addition, when compared to the OLEDs (Comparative Examples 14 to 19) using a single emission layer having the same total thickness as the combined thicknesses of the first and second emission layers of the OLED according to the present disclosure, rather than a two-layered emission structure, it was confirmed that the OLEDs of the present disclosure exhibited significantly superior luminous efficiency and lifetime characteristics in all aspects. This is presumed to be due to the efficient energy transfer enabled by the formation of excitons in the first light-emitting and their subsequent transfer to the second emission layer, where triplet-triplet fusion occurs, in the multi-layered emission structure of the present disclosure, thereby providing high efficiency and long lifetime.
[0309] In contrast, in the case of a device employing a single emission layer, as in the comparative examples, all emission processes must occur within a single layer, which reduces the probability of triplet-triplet fusion. This, in turn, is presumed to lead to device degradation, resulting in reduced efficiency and lifetime. Therefore, it was confirmed that it is easier to fabricate a high-efficiency, long-lifetime OLED by using both the first and second emission layers, compared to a single emission layer.
Examples 53 TO 80: Fabrication of Organic Light-Emitting Diodes Including 1.SUP.st .and 2.SUP.nd .Emission Layers
[0310] Organic light-emitting diodes with a first emission layer and a second emission layer are fabricated in the same manner as in Examples 1 to 52, with the exception that either or both of the emission layers employed two compounds of the following [BH-3] to [BH-7] as a host and each of the emission layers employed the following [BD-4] as a dopant. Here, the structures of [BH-3] to [BH-7] and [BD-4] are as follows and the OLEDs thus obtained were measured at 0.4 mA for luminescence properties.
##STR00287## ##STR00288##
TABLE-US-00002 TABLE 2 1.sup.st Emission 2.sup.nd Emission Driving External layer layer Volt. quantum Lifetime Ex. No. Host Host (V) (EQE, %) (LT97, hr) Ex. 53 1-38 BH-3 BH-6 3.3 13.3 363 Ex. 54 1-39 BH-3 BH-6 3.3 13.2 305 Ex. 55 1-42 BH-3 BH-6 3.3 13.3 314 Ex. 56 1-206 BH-3 BH-6 3.2 13.2 335 Ex. 57 1-214 BH-3 BH-6 3.2 13.2 321 Ex. 58 1-236 BH-3 BH-6 3.3 13.2 307 Ex. 59 1-38 BH-4 BH-6 3.4 13.2 358 Ex. 60 1-206 BH-4 BH-6 3.3 13.2 330 Ex. 61 1-42 BH-5 BH-6 3.5 13.5 299 Ex. 62 1-236 BH-5 BH-6 3.5 13.4 292 Ex. 63 1-39 BH-3 BH-4 3.5 13.3 295 Ex. 64 1-206 BH-3 BH-5 3.5 13.4 315 Ex. 65 1-38 BH-3 BH-7 3.6 13.6 348 Ex. 66 1-42 BH-4 BH-7 3.6 13.4 289 Ex. 67 1-206 BH-5 BH-7 3.6 13.5 305 Ex. 68 1-214 BH-6 BH-7 3.3 13.4 301 Ex. 69 1-38 1-39 BH-3 3.5 13.3 278 Ex. 70 1-38 1-42 BH-4 3.5 13.2 269 Ex. 71 1-38 1-206 BH-5 3.6 13.6 251 Ex. 72 1-42 1-206 BH-6 3.3 13.2 338 Ex. 73 1-42 1-214 BH-7 3.5 13.3 250 Ex. 74 1-38 1-42 BH-3 BH-4 3.6 13.6 248 Ex. 75 1-39 1-42 BH-3 BH-5 3.6 13.6 240 Ex. 76 1-38 1-206 BH-4 BH-6 3.3 13.2 325 Ex. 77 1-39 1-214 BH-5 BH-7 3.6 13.6 284 Ex. 78 1-38 1-236 BH-3 BH-6 3.4 13.3 297 Ex. 79 1-42 1-206 BH-5 BH-6 3.5 13.6 340 Ex. 80 1-42 1-214 BH-6 BH-7 3.4 13.3 337
[0311] As shown in Table 2, it was confirmed that the device comprising, as a host in at least one of the first emission layer and the second emission layer of the OLED according to the present disclosure, two or more different compounds exhibited superior characteristics in terms of low driving voltage, luminous efficiency, and device lifetime.