Organic luminescent medium
AssigneeIdemitsu Kosan Co., Ltd.
InventorsMasahiro Kawamura, Yumiko Mizuki
Life of this patent
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Abstract
An organic luminescent medium including an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (I):
Claims17
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (I):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (I), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar101 to Ar104 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- X is an integer of 0 to 3, and
- Y is an integer of 1 to 3.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (II):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (II), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar105 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and
- Ar201 is a substituted or unsubstituted fused aromatic ring group having 16 to 30 ring carbon atoms, or a substituted or unsubstituted fused heterocyclic group having 10 to 30 ring atoms.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (III):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (III), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar106 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and
- Ar301 is a substituted or unsubstituted 2-naphthyl group or a substituted or unsubstituted fluorenyl group, provided that Ar106 and Ar301 are different.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (10):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (10), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar11 is a substituted or unsubstituted phenyl group, substituted or unsubstituted 2-naphthyl group or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- R111 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, and
- b is an integer of 0 to 7, and plural R111s may be the same or different when b is an integer of 2 or more.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (12):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (12), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and
- Ar12 and Ar13 are independently a hydrogen atom, an aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and Ar12 may form a ring with the naphthalene ring to which Ar12 bonds.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (13):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (13), R101 to R108 and R111 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar15 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and
- b is an integer of 0 to 7, and plural R111s may be the same or different when b is an integer of 2 or more.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (14):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (14), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar16 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and Ar16 may form a ring with the benzene ring to which Ar16 bonds, and
- Ar17 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (15):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (15), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar18 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- L is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,
- R121 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, and
- n is an integer of 0 to 11, and plural R121s may be the same or different when n is an integer of 2 or more.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (16):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (16), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,
- Ar19 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- X11 is an oxygen atom, a sulfur atom, —NR— or —CRaRb, wherein R, Ra and Rb are the same group as those in R101 to R108,
- R121 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, and
- m is an integer of 0 to 7, and plural R121s may be the same or different when m is an integer of 2 or more.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (17):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (17), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar20 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- R201 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom, and
- p is an integer of 0 to 4, and plural R201s may be the same or different when p is an integer of 2 or more.
An organic luminescent medium comprising an aromatic amine derivative represented by the following formula (1) and an anthracene derivative represented by the following formula (18):
- wherein in formula (1), Ar1 to Ar4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and at least one of Ar1 to Ar4 is an aryl group having an electron-attracting group,
- in formula (18), R101 to R108 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- Ar20 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,
- R201 and R301 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a cyano group or a fluorine atom,
- p is an integer of 0 to 4, and plural R201s may be the same or different when p is an integer of 2 or more,
- q is an integer of 0 to 11, plural R301s may be the same or different when q is an integer of 2 or more, and
- adjacent substituents may form a saturated or unsaturated ring.
Dependencies are inferred from the claim text.