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US 2009/0153040 A1Published application
Novel organic electroluminescent compounds and organic electroluminescent device using the same
AssigneeGracel Display Inc.
InventorsHyun Kim, Sung Jin Eum, Young Jun Cho, Hyuck Joo Kwon, Bong Ok Kim, Sung Min Kim, Seung Soo Yoon
Life of this patent
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Abstract
The present invention relates to organic electroluminescent compounds represented by Chemical Formula (1), and electroluminescent devices comprising the same as host material. L1L1M Chemical Formula 1 The electroluminescent compounds according to the invention, when used as electroluminescent host material in an OLED, provide lowered operation voltage and significantly improved power efficiency as compared to conventional host material.
Claims10
An electroluminescent compound represented by Chemical Formula (1):
- L1L1M Chemical Formula 1
- In Chemical Formula (1), ligand L1 is represented by the following structural formula:
- wherein, M represents a bivalent metal;
- X represents O, S or Se;
- ring A represents a 5- or 6-membered heteroaromatic ring or a 5- or 6-heteroaromatic ring fused with a (C6-C20)aromatic ring, and the heteroaromatic ring or the heteroaromatic ring fused with an aromatic ring may form a chemical bond with R1 to create a fused ring, and ring A may be further substituted by (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), phenyl, naphthyl, biphenyl, fluorenyl, thiophenyl, furanyl, tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, di(C1-C10)alkylamino or di(C6-C20)arylamino;
- B represents
- R1 through R4 independently represent hydrogen, (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, (C6-C20)aryl, (C4-C20)heteroaryl, di(C1-C10)alkylamino or di(C6-C20)arylamino, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a fused ring;
- R11 through R22 independently represent hydrogen, (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), (C1-C10)alkoxy, phenyl, cyano or (C3-C7)cycloalkyl, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7) spiro ring or a (C5-C9) fused ring, and R11-R12, R13-R14, R15-R16, R17-R18, R19-R20 or R21-R22 may form a double bond or carbonyl;
- R31 and R32 independently represent (C1-C10)alkyl or (C6-C20)aryl;
- and
- the phenyl, naphthyl, biphenyl, fluorenyl, thiophenyl or furanyl substituent on ring A, or aryl or heteroaryl of R1 through R4 may be further substituted by one or more substituent(s) selected from (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), (C1-C10)alkoxy, phenyl, naphthyl, fluorenyl, tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, di(C1-C10)alkylamino and di(C6-C20)arylamino.
8 more elements
An electroluminescent device comprising an electroluminescent compound represented by Chemical Formula (1):
- L1L1M Chemical Formula 1
- In Chemical Formula (1), ligand L1 is represented by the following structural formula:
- wherein, M represents a bivalent metal;
- X represents O, S or Se;
- ring A represents a 5- or 6-membered heteroaromatic ring or a 5- or 6-heteroaromatic ring fused with a (C6-C20)aromatic ring, and the heteroaromatic ring or the heteroaromatic ring fused with an aromatic ring may form a chemical bond with R1 to create a fused ring, and ring A may be further substituted by (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), phenyl, naphthyl, biphenyl, fluorenyl, thiophenyl, furanyl, tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, di(C1-C10)alkylamino or di(C6-C20)arylamino;
- B represents
- R1 through R4 independently represent hydrogen, (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, (C6-C20)aryl, (C4-C20)heteroaryl, di(C1-C10)alkylamino or di(C6-C20)arylamino, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a fused ring;
- R11 through R22 independently represent hydrogen, (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), (C1-C10)alkoxy, phenyl, cyano or (C3-C7)cycloalkyl, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7) spiro ring or a (C5-C9) fused ring, and R1, —R12, R13-R14, R15-R16, R17-R18, R19-R20 or R21-R22 may form a double bond or carbonyl;
- R31 and R32 independently represent (C1-C10)alkyl or (C6-C20)aryl;
- and
- the phenyl, naphthyl, biphenyl, fluorenyl, thiophenyl or furanyl substituent on ring A, or aryl or heteroaryl of R1 through R4 may be further substituted by one or more substituent(s) selected from (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), (C1-C10)alkoxy, phenyl, naphthyl, fluorenyl, tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, di(C1-C10)alkylamino and di(C6-C20)arylamino, wherein the electroluminescent compound is employed as host material of an electroluminescent layer.
8 more elements
An organic solar cell which comprises an electroluminescent compound comprising an electroluminescent compound represented by Chemical Formula (1):
- L1L1M Chemical Formula 1
- In Chemical Formula (1), ligand L1 is represented by the following structural formula:
- wherein, M represents a bivalent metal;
- X represents O, S or Se;
- ring A represents a 5- or 6-membered heteroaromatic ring or a 5- or 6-heteroaromatic ring fused with a (C6-C20)aromatic ring, and the heteroaromatic ring or the heteroaromatic ring fused with an aromatic ring may form a chemical bond with R1 to create a fused ring, and ring A may be further substituted by (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), phenyl, naphthyl, biphenyl, fluorenyl, thiophenyl, furanyl, tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, di(C1-C10)alkylamino or di(C6-C20)arylamino;
- B represents
- R1 through R4 independently represent hydrogen, (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, (C6-C20)aryl, (C4-C20)heteroaryl, di(C1-C10)alkylamino or di(C6-C20)arylamino, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a fused ring;
- R11 through R22 independently represent hydrogen, (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), (C1-C10)alkoxy, phenyl, cyano or (C3-C7)cycloalkyl, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7) spiro ring or a (C5-C9) fused ring, and R11-R12, R13-R14, R15-R16, R17-R18, R19-R20 or R21-R22 may form a double bond or carbonyl;
- R31 and R32 independently represent (C1-C10)alkyl or (C6-C20)aryl;
- and
- the phenyl, naphthyl, biphenyl, fluorenyl, thiophenyl or furanyl substituent on ring A, or aryl or heteroaryl of R1 through R4 may be further substituted by one or more substituent(s) selected from (C1-C10)alkyl, halogen, (C1-C10)alkyl with halogen substituent(s), (C1-C10)alkoxy, phenyl, naphthyl, fluorenyl, tri(C1-C10)alkylsilyl, tri(C6-C20)arylsilyl, di(C1-C10)alkyl(C6-C20)arylsilyl, di(C1-C10)alkylamino and di(C6-C20)arylamino.
8 more elements
Dependencies are inferred from the claim text.