PLATINUM COMPLEX COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME

• US 20090153045A1
• Filed: 12/12/2008
• Published: 06/18/2009
• Est. Priority Date: 12/14/2007
• Status: Abandoned Application

• Current Assignee: UDC Ireland Limited (Universal Display Corporation)
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: Murakami, Takeshi, Igarashi, Tatsuya, Kinoshita, Ikuo
• Application Number:
  US12/333,370
• Publication Number:
  US 20090153045A1
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

A compound is represented by the following formula (I):

wherein each of Ar₁ and Ar₂ independently represents an aromatic ring or an aromatic heterocyclic ring; each of R₁, R₂, R₃ and R₄ independently represents a hydrogen atom or a substituent; each of Z₁ and Z₂ independently represents a carbon atom or a nitrogen atom; each of ring Q₁ containing a carbon atom and Z₁, and ring Q₂ containing a carbon atom and Z₂ independently represents an aromatic ring or an aromatic heterocyclic ring; and A₁ represents a single bond or a divalent linking group.

Claims

1. A compound represented by the following formula (I):

wherein

each of Ar₁ and Ar₂ independently represents an aromatic ring or an aromatic heterocyclic ring;

each of R₁, R₂, R₃ and R₄ independently represents a hydrogen atom or a substituent;

each of Z₁ and Z₂ independently represents a carbon atom or a nitrogen atom;

each of ring Q₁ containing a carbon atom and Z₁, and ring Q₂ containing a carbon atom and Z₂ independently represents an aromatic ring or an aromatic heterocyclic ring; and

A₁ represents a single bond or a divalent linking group.

2. The compound as claimed in claim 1, wherein

the formula (I) is represented by the following formula (II):

wherein

each of ring Q₅ containing Z₁₅, Z₁₇ and Z₁₉, and ring Q₆ containing Z₁₆, Z₁₈ and Z₂₀ independently represents a 5- or 6-membered aromatic ring or aromatic heterocyclic ring;

each of Z₁₅, Z₁₆, Z₁₇, Z₁₈, Z₁₉ and Z₂₀ independently represents a carbon atom or a nitrogen atom;

each of a bond for bonding Z₁₅ to Z₁₇, a bond for bonding Z₁₅ to Z₁₉, a bond for bonding Z₁₆ to Z₁₈, and a bond for bonding Z₁₆ to Z₂₀ independently represents a single bond or a double bond, provided that when Z₁₅ represents a nitrogen atom, each of the bond for bonding Z₁₅ to Z₁₇ and the bond for bonding Z₁₅ to Z₁₉ represents a single bond, and when Z₁₆ represents a nitrogen atom, each of the bond for bonding Z₁₆ to Z₁₈ and the bond for bonding Z₁₆ to Z₂₀ represents a single bond;

Z₁₇, Z₁₈, Z₁₉ and Z₂₀ do not have a substituent;

each of ring Q₃ containing a carbon atom, Z₁₁ and Z₁₃, and ring Q₄ containing a carbon atom, Z₁₂ and Z₁₄ independently represents an aromatic ring or an aromatic heterocyclic ring;

each of Z₁₁, Z₁₂, Z₁₃ and Z₁₄ independently represents a carbon atom or a nitrogen atom;

each of a bond for bonding Z₁₁ to the carbon atom coordinating to Pt contained in ring Q₃, a bond for bonding Z₁₁ to Z₁₃, a bond for bonding Z₁₂ to the carbon atom coordinating to Pt contained in ring Q₄, and a bond for bonding Z₁₂ to Z₁₄ independently represents a single bond or a double bond, provided that when Z₁₁ represents a nitrogen atom, each of the bond for bonding Z₁₁ to the carbon atom coordinating to Pt contained in ring Q₃ and the bond for bonding Z₁ to Z₁₃ represents a single bond, and when Z₁₂ represents a nitrogen atom, each of the bond for bonding Z₁₂ to the carbon atom coordinating to Pt contained in ring Q₄ and the bond for bonding Z₁₂ to Z₁₄ represents a single bond;

Z₁₃ and Z₁₄ do not have a substituent;

each of R₁₁, R₁₂, R₁₃ and R₁₄ independently represents a hydrogen atom or a substituent; and

A₂ represents a single bond or a divalent linking group.

3. The compound as claimed in claim 2, wherein

the formula (II) is represented by the following formula (III):

wherein

each of Z₂₅ and Z₂₆ represents a carbon atom;

each of Z₂₇, Z₂₈, Z₂₉, Z₃₀, Z₃₁, Z₃₂, Z₃₃, Z₃₄, Z₃₅ and Z₃₆ independently represents a carbon atom or a nitrogen atom;

Z₂₇, Z₂₈, Z₂₉ and Z₃₀ do not have a substituent;

each of Z₂₁, Z₂₂, Z₂₃ and Z₂₄ independently represents a carbon atom or a nitrogen atom;

each of ring Q₇ containing a carbon atom, Z₂₁ and Z₂₃ and ring Q₈ containing a carbon atom, Z₂₂ and Z₂₄ independently represents an aromatic ring or an aromatic heterocyclic ring;

each of a bond for bonding Z₂₁ to the carbon atom coordinating to Pt contained in ring Q₇, a bond for bonding Z₂₁ to Z₂₃, a bond for bonding Z₂₂ to the carbon atom coordinating to Pt contained in ring Q₉, and a bond for bonding Z₂₂ to Z₂₄ independently represents a single bond or a double bond, provided that when Z₂₁ represents a nitrogen atom, each of the bond for bonding Z₂₁ to the carbon atom coordinating to Pt contained in ring Q₇ and the bond for bonding Z₂₁ to Z₂₃ represents a single bond, and when Z₂₂ represents a nitrogen atom, each of the bond for bonding Z₂₂ to the carbon atom coordinating to Pt contained in ring Q₈ and the bond for bonding Z₂₂ to Z₂₄ represents a single bond;

Z₂₃ and Z₂₄ do not have a substituent;

each of R₂₁, R₂₂, R₂₃ and R₂₄ independently represents a hydrogen atom or a substituent; and

A₃ represents a single bond or a divalent linking group.

4. The compound as claimed in claim 3, wherein

the formula (III) is represented by the following formula (IV):

wherein

each of Z₄₁, Z₄₂, Z₄₃ and Z₄₄ independently represents a carbon atom or a nitrogen atom;

each of ring Q₉ containing a carbon atom, Z₄₁ and Z₄₃ and ring Q₁₀ containing a carbon atom, Z₄₂ and Z₄₄ independently represents an aromatic ring or an aromatic heterocyclic ring;

each of a bond for bonding Z₄₁ to the carbon atom coordinating to Pt contained in ring Q₉, a bond for bonding Z₄₁ to Z₄₃, a bond for bonding Z₄₂ to the carbon atom coordinating to Pt contained in ring Q₁₀, and a bond for bonding Z₄₂ to Z₄₄ independently represents a single bond or a double bond, provided that when Z₄₁ represents a nitrogen atom, each of the bond for bonding Z₄₁ to the carbon atom coordinating to Pt contained in ring Q₉ and the bond for bonding Z₄₁ to Z₄₃ represents a single bond, and when Z₄₂ represents a nitrogen atom, each of the bond for bonding Z₄₂ to the carbon atom coordinating to Pt contained in ring Q₁₀ and the bond for bonding Z₄₂ to Z₄₄ represents a single bond;

Z₄₃ and Z₄₄ do not have a substituent;

each of R₃₁, R₃₂, R₃₃, R₃₄, R₃₅, R₃₆, R₃₇, R₃₈, R₃₉ and R₄₀ independently represents a hydrogen atom or a substituent; and

A₄ represents a single bond or a divalent linking group.

5. The compound as claimed in claim 4, wherein

the formula (IV) is represented by the following formula (V):

wherein

each of R₄₁, R₄₂, R₄₃, R₄₄, R₄₅, R₄₆, R₄₇, R₄₈, R₄₉, R₅₀, R₅₁, R₅₂, R₅₃, R₅₄, R₅₅ and R₅₆ independently represents a hydrogen atom or a substituent; and

A₅ represents a single bond or a divalent linking group.

6. The compound as claimed in claim 4, wherein

the formula (IV) is represented by the following formula (VI):

wherein

each of R₆₁, R₆₂, R₆₃, R₆₄, R₆₅, R₆₆, R₆₇, R₆₈, R₆₉, R₇₀, R₇₁, R₇₂, R₇₃ and R₇₄ independently represents a hydrogen atom or a substituent; and

A₆ represents a single bond or a divalent linking group.

7. The compound as claimed in claim 2, wherein

the formula (II) is represented by the following formula (VII):

wherein

each of Z₅₅, Z₅₆, Z₅₇, Z₅₈, Z₅₉, Z₆₀, Z₆₁ and Z₆₂ independently represents a carbon atom or a nitrogen atom;

Z₅₅, Z₅₆, Z₆₁ and Z₆₂ do not have a substituent;

each of Z₅₁, Z₅₂, Z₅₃ and Z₅₄ independently represents a carbon atom or a nitrogen atom,

each of ring Q₁₁ containing a carbon atom, Z₅₁ and Z₅₃ and ring Q₁₂ containing a carbon atom, Z₅₂ and Z₅₄ independently represents an aromatic ring or an aromatic heterocyclic ring,

each of a bond for bonding Z₅₁ to the carbon atom coordinating to Pt contained in ring Q₁₁, a bond for bonding Z₅₁ to Z₅₃, a bond for bonding Z₅₂ to the carbon atom coordinating to Pt contained in ring Q₁₂, and a bond for bonding Z₅₂ to Z₅₄ independently represents a single bond or a double bond, provided that when Z₅₁ represents a nitrogen atom, each of the bond for bonding Z₅₁ to the carbon atom coordinating to Pt contained in ring Q₁₁ and the bond for bonding Z₅₁ to Z₅₃ represents a single bond, and when Z₅₂ represents a nitrogen atom, each of the bond for bonding Z₅₂ to the carbon atom coordinating to Pt contained in ring Q₁₂ and the bond for bonding Z₅₂ to Z₅₄ represents a single bond; and

Z₅₃ and Z₅₄ do not have a substituent;

each of R₁₁₁, R₁₁₂, R₁₁₃ and R₁₁₄ independently represents a hydrogen atom or a substituent; and

A₇ represents a single bond or a divalent linking group.

8. The compound as claimed in claim 7, wherein

the formula (VII) is represented by the following formula (VIII):

wherein

each of Z₇₁, Z₇₂, Z₇₃ and Z₇₄ independently represents a carbon atom or a nitrogen atom;

each of ring Q₁₃ containing a carbon atom, Z₇₁ and Z₇₃ and ring Q₁₄ containing a carbon atom, Z₇₂ and Z₇₄ independently represents an aromatic ring or an aromatic heterocyclic ring;

each of a bond for bonding Z₇₁ to the carbon atom coordinating to Pt contained in ring Q₁₃, a bond for bonding Z₇₁ to Z₇₃, a bond for bonding Z₇₂ to the carbon atom coordinating to Pt contained in ring Q₁₄, and a bond for bonding Z₇₂ to Z₇₄ independently represents a single bond or a double bond, provided that when Z₇₁ represents a nitrogen atom, each of the bond for bonding Z₇₁ to the carbon atom coordinating to Pt contained in ring Q₁₃ and the bond for bonding Z₇₁ to Z₇₃ represents a single bond, and when Z₇₂ represents a nitrogen atom, each of the bond for bonding Z₇₂ to the carbon atom coordinating to Pt contained in ring Q₁₄ and the bond for bonding Z₇₂ to Z₇₄ represents a single bond;

Z₇₃ and Z₇₄ do not have a substituent;

each of R₁₂₁, R₁₂₂, R₁₂₃, R₁₂₄, R₁₂₅, R₁₂₆, R₁₂₇ and R₁₂₈ independently represents a hydrogen atom or a substituent; and

A₈ represents a single bond or a divalent linking group.

9. The compound as claimed in claim 8, wherein

the formula (VII) is represented by the following formula (IX):

wherein

each of R₁₃₁, R₁₃₂, R₁₃₃, R₁₃₄, R₁₃₅, R₁₃₆, R₁₃₇, R₁₃₈, R₁₃₉, R₁₄₀, R_141p R₁₄₂, R₁₄₃ and R₁₄₄ independently represents a hydrogen atom or a substituent; and

A₉ represents a single bond or a divalent linking group.

10. The compound as claimed in claim 8, wherein

the formula (VIII) is represented by the following formula (X):

wherein

each of R₁₅₁, R₁₅₂, R₁₅₃, R₁₅₄, R₁₅₅, R₁₅₆, R₁₅₇, R₁₅₈, R₁₆₁, R₁₆₂, R₁₆₃ and R₁₆₄ independently represents a hydrogen atom or a substituent; and

A₁₀ represents a single bond or a divalent linking group.

11. An organic electroluminescence device comprising:

a pair of electrodes; and

an organic layer between the pair of electrodes,

wherein the organic layer contains the compound as claimed in claim 1.

12. An organic electroluminescence device comprising:

a pair of electrodes, and

a light-emitting layer between the pair of electrodes,

wherein the light-emitting layer contains the compound as claimed in claim 1 in a proportion of from 20 to 30 wt % of the total mass of the light-emitting layer.