Organometallic complex and organic electroluminescent device using the same
AssigneeSamsung Mobile Display Co., Ltd.
InventorsJong-Hyoup Lee, Seok Chang, Das Rupasree Ragini, Hee-Kyung Kim, Lyong-Sun Pu
Life of this patent
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Abstract
Provided is an organometallic complex that highly effectively emits a phosphorescent light and an organic electroluminescent device using the same. The organometallic complex can be used to form an organic layer of an organic electroluminescent device, is a highly effective phosphorescent material emitting light of 400 nm to 650 nm, and can be used with a green emission material or a red emission material to emit a white light. In addition, the organometallic complex can be used in a solution process due to its high solubility, and thus, is suitable for large-scale screens.
Claims20
An organometallic complex represented by Formula 1:
- where M is Ir, Os, Pt, Pb, Re, Ru, or Pd;
- CyN is a substituted or non-substituted C3-C60 heterocyclic group containing N that can be bonded to M, or a substituted or non-substituted C3-C60 heteroaryl group containing N that can be bonded to M;
- CyC is a substituted or non-substituted C4-C60 carbocyclic group containing C that can be bonded to M, a substituted or non-substituted C3-C60 heterocyclic group containing C that can be bonded to M, a substituted or non-substituted C3-C60 aryl group containing C that can be bonded to M, or a substituted or non-substituted C3-C60 heteroaryl group containing C that can be bonded to M;
- CyN-CyC is a cyclometalating ligand that is bonded to M through N and C, wherein substituents of CyN-CyC are each independently a halogen atom, —OR, —N(R)(R′), —P(R)(R′), —POR, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, a substituted or non-substituted C1-C20 alkyl group, or a substituted or non-substituted C6-C20 aryl group where R, R′, and R″ are each independently hydrogen, a substituted or non-substituted C1-C20 alkyl group, a substituted or non-substituted C1-C10 alkoxy group, a substituted or non-substituted C2-C20 alkenyl group, a substituted or non-substituted C2-C20 alkynyl group, a substituted or non-substituted C1-C20 heteroalkyl group, a substituted or non-substituted C6-C40 aryl group, a substituted or non-substituted C7-C40 arylalkyl group, a substituted or non-substituted C7-C40 alkylaryl group, a substituted or non-substituted C2-C40 heteroaryl group, or a substituted or non-substituted C3-C40 heteroarylalkyl group, and CyN and CyC are connected to form a substituted or non-substituted 4-7 atom cyclic group or a substituted or non-substituted 4-7 atom heterocyclic group;
- m1 is an integer from 0 to 2, and m2 is 3-m1;
- A is a ligand containing at least two nitrogen atoms, and A is bonded to M through one of said at least two nitrogen atoms;
- X is N, S, or P;
- Y is selected from the group consisting of hydrogen, a substituted or non-substituted C1-C20 alkyl group, a substituted or non-substituted C1-C10 alkoxy group, a substituted or non-substituted C2-C20 alkenyl group, a substituted or non-substituted C2-C20 alkynyl group, a substituted or non-substituted C1-C20 heteroalkyl group, a substituted or non-substituted C6-C40 aryl group, a substituted or non-substituted C7-C40 arylalkyl group, a substituted or non-substituted C7-C40 alkylaryl group, a substituted or non-substituted C2-C40 heteroaryl group, and a substituted or non-substituted C3-C40 heteroarylalkyl group;
- and
- Q is a substituted or non-substituted C1-C20 alkylene group.
An organometallic complex represented by Formula 1:
- where M is Ir, Os, Pt, Pb, Re, Ru, or Pd;
- CyN-CyC is represented by one of Formulae 1-(i) to 1-(xxiii):
- where R1, R2, R3, R4, and R5 are single-substituted or multi-substituted functional groups, and R1, R2, R3, R4, and R5 are each independently H, a halogen atom, —OR, —N(R)2, —P(R)2, —POR, —PO2R, —PO3R, —SR, —Si(R)3, —B(R)2, —B(OR)2, —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, a C1-C20 alkyl group, or a C6-C20 aryl group, where R is selected from the group consisting of hydrogen, a substituted or non-substituted C1-C20 alkyl group, a substituted or non-substituted C1-C10 alkoxy group, a substituted or non-substituted C2-C20 alkenyl group, a substituted or non-substituted C2-C20 alkynyl group, a substituted or non-substituted C1-C20 heteroalkyl group, a substituted or non-substituted C6-C40 aryl group, a substituted or non-substituted C7-C40 arylalkyl group, a substituted or non-substituted C7-C40 alkylaryl group, a substituted or non-substituted C2-C40 heteroaryl group, and a substituted or non-substituted C3-C40 heteroarylalkyl group, and Z is one of S, O, and NR0 where R0 is H or a C1-C20 alkyl group;
- m1 is an integer from 0 to 2, and m2 is 3-m1;
- A is a ligand containing at least two nitrogen atoms and A is bonded to M through one of said at least two nitrogen atoms;
- X is N, S, or P;
- Y is selected from the group consisting of hydrogen, a substituted or non-substituted C1-C20 alkyl group, a substituted or non-substituted C1-C10 alkoxy group, a substituted or non-substituted C2-C20 alkenyl group, a substituted or non-substituted C2-C20 alkynyl group, a substituted or non-substituted C1-C20 heteroalkyl group, a substituted or non-substituted C6-C40 aryl group, a substituted or non-substituted C7-C40 arylalkyl group, a substituted or non-substituted C7-C40 alkylaryl group, a substituted or non-substituted C2-C40 heteroaryl group, and a substituted or non-substituted C3-C40 heteroarylalkyl group;
- and
- Q is a substituted or non-substituted C1-C20 alkylene group.
An organic electroluminescent device, comprising:
- a pair of electrodes;
- and
- an organic layer interposed between the pair of electrodes, the organic layer composed of the organometallic complex represented by Formula 1
- where M is Ir, Os, Pt, Pb, Re, Ru, or Pd;
- CyN is a substituted or non-substituted C3-C60 heterocyclic group containing N that can be bonded to M, or a substituted or non-substituted C3-C60 heteroaryl group containing N that can be bonded to M;
- CyC is a substituted or non-substituted C4-C60 carbocyclic group containing C that can be bonded to M, a substituted or non-substituted C3-C60 heterocyclic group containing C that can be bonded to M, a substituted or non-substituted C3-C60 aryl group containing C that can be bonded to M, or a substituted or non-substituted C3-C60 heteroaryl group containing C that can be bonded to M;
- CyN-CyC is a cyclometalating ligand that is bonded to M through N and C, wherein substituents of CyN-CyC are each independently a halogen atom, —OR, —N(R)(R′), —P(R)(R), —POR, —PO2R, —PO3R, —SR, —Si(R)(R′)(R″), —B(R)(R′), —B(OR)(OR′), —C(O)R, —C(O)OR, —C(O)N(R), —CN, —NO2, —SO2, —SOR, —SO2R, —SO3R, a substituted or non-substituted C1-C20 alkyl group, or a substituted or non-substituted C6-C20 aryl group where R, R′, and R″ are each independently hydrogen, a substituted or non-substituted C1-C20 alkyl group, a substituted or non-substituted C1-C10 alkoxy group, a substituted or non-substituted C2-C20 alkenyl group, a substituted or non-substituted C2-C20 alkynyl group, a substituted or non-substituted C1-C20 heteroalkyl group, a substituted or non-substituted C6-C40 aryl group, a substituted or non-substituted C7-C40 arylalkyl group, a substituted or non-substituted C7-C40 alkylaryl group, a substituted or non-substituted C2-C40 heteroaryl group, or a substituted or non-substituted C3-C40 heteroarylalkyl group, and CyN and CyC are connected to form a substituted or non-substituted 4-7 atom cyclic group or a substituted or non-substituted 4-7 atom heterocyclic group;
- m1 is an integer from 0 to 2, and m2 is 3-m1;
- A is a ligand containing at least two nitrogen atoms, and A is bonded to M through one of said at least two nitrogen atoms;
- X is N, S, or P;
- Y is selected from the group consisting of hydrogen, a substituted or non-substituted C1-C20 alkyl group, a substituted or non-substituted C1-C10 alkoxy group, a substituted or non-substituted C2-C20 alkenyl group, a substituted or non-substituted C2-C20 alkynyl group, a substituted or non-substituted C1-C20 heteroalkyl group, a substituted or non-substituted C6-C40 aryl group, a substituted or non-substituted C7-C40 arylalkyl group, a substituted or non-substituted C7-C40 alkylaryl group, a substituted or non-substituted C2-C40 heteroaryl group, and a substituted or non-substituted C3-C40 heteroarylalkyl group;
- and
- Q is a substituted or non-substituted C1-C20 alkylene group.
Dependencies are inferred from the claim text.