TRANSITION METAL COMPLEX COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE COMPOUND

• US 20070141397A1
• Filed: 12/13/2006
• Published: 06/21/2007
• Est. Priority Date: 12/15/2005
• Status: Abandoned Application

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Okuda, Fumio, Watanabe, Masami
• Application Number:
  US11/610,093
• Publication Number:
  US 20070141397A1
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07D 213/81 Amides; Imides
• CPC Class Codes: C07D 233/58 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/655 comprising only sulfur as heteroatom
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

The present invention relates to a transition metal complex compound of a specific structure having a metal carbene bond and an organic electroluminescent device in which an organic thin film layer comprising a single layer or plural layers having at least a light emitting layer is interposed between an anode and a cathode, wherein at least one layer in the organic thin film layer contains the transition metal complex compound described above, and provided are an organic EL device having a high luminous efficiency and emitting blue light and a transition metal complex compound materializing the same.

Claims

1. A transition metal complex compound having a metal carbene bond represented by the following Formula (1)

[in Formula (1), a bond shown by a solid line (—

) represents a covalent bond, and a bond shown by an arrow (→

) represents a coordinate bond;

L²→

M represents a metal carbene bond;

M represents a metal atom of iridium (Ir) or platinum (Pt);

L¹-L²-L³ represents a cross-linked tridentate ligand, and L¹⁶, L¹⁷ and L¹⁸ each independently represent a unidentate ligand, a cross-linked bidentate ligand in which two of them are cross-linked or a cross-linked tridentate ligand in which at least two of L¹⁶ and L¹⁷, L¹7 and L¹⁸ and L¹⁶ and L¹⁸ are cross-linked;

at least one of L¹, L² and L³ may be cross-linked with at least one of L¹⁶, L¹⁷ and L¹⁸;

i, j and k each represent an integer of 0 to 1, and 2+i represents a valence of metal M;

L¹ and L³ each independently represent a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a divalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a divalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a divalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkylene group having 3 to 50 ring carbon atoms which may have a substituent, an alkylene group having 1 to 30 carbon atoms which may have a substituent, an alkenylene group having 2 to 30 carbon atoms which may have a substituent or an aralkylene group having 7 to 40 carbon atoms which may have a substituent;

L² represents a divalent group having carbene carbon which may have a substituent;

L¹⁶ represents a monovalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a monovalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a monovalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a monovalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent or an aralkyl group having 7 to 40 carbon atoms which may have a substituent;

when L¹⁶ and L¹⁷ or L¹⁶ and L¹⁸ are cross-linked, it is a divalent group of each group described above, and when L¹⁶ and L¹⁷ and L¹⁶ and L¹⁸ are cross-linked, it is a trivalent group of each group described above;

L¹⁷ and L¹⁸ each independently represent a ligand comprising a heterocycle having 3 to 30 ring carbon atoms which may have a substituent, carboxylic acid ester having 1 to 30 carbon atoms which may have a substituent, carboxylic amide having 1 to 30 carbon atoms, amine which may have a substituent, phosphine which may have a substituent, isonitrile which may have a substituent, ether having 1 to 30 carbon atoms which may have a substituent, thioether having 1 to 30 carbon atoms which may have a substituent or a double bond-containing compound having 1 to 30 carbon atoms which may have a substituent;

when L¹⁶ and L¹⁷, L¹⁶ and L¹⁸ or L¹⁷ and L¹⁸ are cross-linked, it is a monovalent group of each ligand described above, and when L¹⁶ and L¹⁷ and L¹⁷ and L¹⁸ are cross-linked and when L¹⁶ and L¹⁸ and L¹⁷ and L¹⁸ are cross-linked, it is a divalent group of each ligand described above].

6. The transition metal complex compound having a metal carbene bond as described in claim 1, wherein a L¹L²L³M part in Formula (1) has a structure represented by the following Formula (6):

[in Formula (6), R¹² to R²¹ each independently represent a hydrogen atom, a halogen atom, a thiocyano group or a cyano group, a nitro group, a —

S(═

O)₂R′

group or a —

S(═

O)R′

group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 30 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 ring carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 ring carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms, and they may be cross-linked;

(R′

each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent)].

11. The transition metal complex compound having a metal carbene bond as described in claim 1 or 2, wherein a M(L¹⁶)_i(L¹⁷)_j(L¹⁸)_k part in Formula (1) and Formula (2) each has independently a structure represented by the following Formula (12), (13) or (14):

M(L¹⁶)_i(L¹⁷)_j(L¹⁸)

[in Formulas (12), (13) and (14), R⁷¹ to R¹⁰⁰ each independently represent a hydrogen atom, a halogen atom, a thiocyano group or a cyano group, a nitro group, a —

S(═

O)₂R′

group or a —

S(═

O)R′

group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 30 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 ring carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 ring carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms, and they may be cross-linked;

(R′

each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent)].

13. The transition metal complex compound having a metal carbene bond as described in any of claims 1 to 5, wherein M described above is Ir.

14. An organic electroluminescent device in which an organic thin film layer comprising a single layer or plural layers having at least a light emitting layer is interposed between an anode and a cathode, wherein at least one layer in the organic thin film layer contains the transition metal complex compound having a metal carbene bond as described in any of claims 1 to 5.

15. The organic electroluminescent device as described in claim 14, wherein the light emitting layer described above contains the transition metal complex compound having a atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 ring carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 ring carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms, and they may be cross-linked;

(R′

each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an metal carbene bond as described in any of claims 1 to 5 as a luminescent material.

16. The organic electroluminescent device as described in claim 14, containing the transition metal complex compound having a metal carbene bond as described in any of claims 1 to 5 as a dopant.

17. The organic electroluminescent device as described in claim 14, wherein an electron injecting layer and/or an electron transporting layer is provided between the light emitting layer and the cathode described above, and the above electron injecting layer and/or electron transporting layer comprises a π

-electron deficient nitrogen-containing heterocyclic derivative as a principal component.

18. The organic electroluminescent device as described in claim 14, wherein a reducing dopant is added to an interfacial region between the cathode and the organic thin film layer described above

2. A transition metal complex compound having a metal carbene bond represented by the following Formula (2):

[in Formula (2), a bond shown by a solid line (—

) represents a covalent bond, and a bond shown by an arrow (→

) represents a coordinate bond;

L⁴→

M represents a metal carbene bond;

M represents a metal atom of iridium (Ir) or platinum (Pt);

L⁴-L⁵-L⁶ represents a cross-linked tridentate ligand, and L¹⁶, L¹⁷ and L¹⁸ each independently represent a unidentate ligand, a cross-linked bidentate ligand in which two of them are cross-linked or a cross-linked tridentate ligand in which at least two of L¹⁶ and L¹⁷, L¹⁷ and L¹⁸ and L¹⁶ and L¹⁸ are cross-linked;

at least one of L⁴, L⁵ and L⁶ may be cross-linked with at least one of L¹⁶, L¹⁷ and L¹;

i, j and k each represent an integer of 0 to 1, and 2+i represents a valence of metal M;

L⁶ each independently represents a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a divalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a divalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a divalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkylene group having 3 to 50 ring carbon atoms which may have a substituent, an alkylene group having 1 to 30 carbon atoms which may have a substituent, an alkenylene group having 2 to 30 carbon atoms which may have a substituent or an aralkylene group having 7 to 40 carbon atoms which may have a substituent;

L⁵ represents a group obtained by removing one hydrogen atom of each group represented by L⁶ described above to make it trivalent;

L⁴ represents a monovalent group having carbene carbon which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent or a monovalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, and at least one of them is a monovalent group having carbene carbon which may have a substituent;

L¹⁶ represents a monovalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a monovalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a monovalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a monovalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent or an aralkyl group having 7 to 40 carbon atoms which may have a substituent;

when L16 and L¹⁷ or L¹⁶ and L¹⁸ are cross-linked, it is a divalent group of each group described above, and when L¹⁶ and L¹⁷ and L¹⁶ and L¹⁸ are cross-linked, it is a trivalent group of each group described above;

L¹⁷ and L¹⁸ each independently represent a ligand comprising a heterocycle having 3 to 30 ring carbon atoms which may have a substituent, carboxylic acid ester having 1 to 30 carbon atoms which may have a substituent, carboxylic amide having 1 to 30 carbon atoms, amine which may have a substituent, phosphine which may have a substituent, isonitrile which may have a substituent, ether having 1 to 30 carbon atoms which may have a substituent, thioether having 1 to 30 carbon atoms which may have a substituent or a double bond-containing compound having 1 to 30 carbon atoms which may have a substituent;

when L¹⁶ and L¹⁷, L¹⁶ and L¹⁸ or L¹⁷ and L¹⁸ are cross-linked, it is a monovalent group of each ligand described above, and when L¹⁶ and L¹⁷ and L¹⁷ and L¹⁸ are cross-linked and when L¹⁶ and L¹⁸ and L¹⁷ and L¹⁸ are cross-linked, it is a divalent group of each ligand described above].

7. The transition metal complex compound having a metal carbene bond as described in claim 2, wherein a L⁴L⁵L⁶M part in Formula (2) has a structure represented by the following Formula (7):

[in Formula (7), R²² to R³¹ each independently represent a hydrogen atom, a halogen atom, a thiocyano group or a cyano group, a nitro group, a —

S(═

O)₂R′

group or a —

S(═

O)R′

group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 30 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 ring carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 ring carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms, and they may be cross-linked;

(R′

each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent)].

3. A transition metal complex compound having a metal carbene bond represented by the following Formula (3):

[in Formula (3), a bond shown by a solid line (—

) represents a covalent bond, and a bond shown by an arrow (→

) represents a coordinate bond;

M represents a metal atom of iridium (Ir) or platinum (Pt);

L⁷-L⁸-L⁹ represents a cross-linked tridentate ligand, and L¹⁹, L²⁰ and L²¹ each independently represent a unidentate ligand, a cross-linked bidentate ligand in which two of them are cross-linked or a cross-linked tridentate ligand in which at least two of L¹⁹ and L²⁰, L²⁰ and L²¹ and L¹⁹ and L²¹ are cross-linked;

at least one of L⁷, L⁸ and L⁹ may be cross-linked with at least one of L¹⁹, L²⁰ and L²¹;

i, j and k each represent an integer of 0 to 1, and 1+i+j represents a valence of metal M;

L⁸ represents a trivalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a trivalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a trivalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a trivalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a trivalent cycloalkane moiety having 3 to 50 ring carbon atoms which may have a substituent, a trivalent alkane moiety having 1 to 30 carbon atoms which may have a substituent, a trivalent alkene moiety having 2 to 30 carbon atoms which may have a substituent or a trivalent arylalkane moiety having 7 to 40 carbon atoms which may have a substituent;

L⁷ and L⁹ each independently represent a monovalent group having carbene carbon which may have a substituent, a monovalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent or a monovalent heterocyclic group having 5 to 30 ring carbon atoms which may have a substituent; and

at least one of L⁷ and L⁹ is a monovalent group having carbene carbon which may have a substituent;

L¹⁹ and L²⁰ each independently represent a monovalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a monovalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a monovalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a monovalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent or an aralkyl group having 7 to 40 carbon atoms which may have a substituent;

when L¹⁹ and L²⁰, L¹⁹ and L²¹ or L²⁰ and L²¹ are cross-linked, it is a divalent group of each group described above, and when L¹⁹ and L²⁰ and L¹⁹ and L²¹ are cross-linked and when L¹⁹ and L²⁰ and L²⁰ and L²¹ are cross-linked, it is a trivalent group of each group described above;

L²¹ represents a ligand comprising a heterocycle having 3 to 30 ring carbon atoms which may have a substituent, carboxylic acid ester having 1 to 30 carbon atoms which may have a substituent, carboxylic amide having 1 to 30 carbon atoms, amine which may have a substituent, phosphine which may have a substituent, isonitrile which may have a substituent, ether having 1 to 30 carbon atoms which may have a substituent, thioether having 1 to 30 carbon atoms which may have a substituent or a double bond-containing compound having 1 to 30 carbon atoms which may have a substituent;

when L¹⁹ and L²¹ or L²⁰ and L²¹ are cross-linked, it is a monovalent group of each ligand described above, and when L¹⁹ and L²¹ and L²⁰ and L²¹ are cross-linked, it is a divalent group of each ligand described above].

8. The transition metal complex compound having a metal carbene bond as described in claim 3, wherein a L⁷L⁸L⁹M part in Formula (3) has a structure represented by the following Formula (8) or (9):

[in Formula (8) and (9), R³² to R⁵⁰ each independently represent a hydrogen atom, a halogen atom, a thiocyano group or a cyano group, a nitro group, a —

S(═

O)₂R′

group or a —

S(═

O)R′

group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 30 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 ring carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 ring carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms, and they may be cross-linked;

(R′

each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent)].

12. The transition metal complex compound having a metal carbene bond as described in claim 3, 4 or 5, wherein a M(L¹⁹)_i(L²⁰)(L²¹)_k part in Formula (3), Formula (4) and Formula (5) each has independently a structure represented by the following Formula (15), (16), (17) or (18):

M(L¹⁹)_i(L²⁰)_j(L²¹)

[in Formulas (15), (16), (17) and (18), R¹⁰¹ to R¹³² each independently represent a hydrogen atom, a halogen atom, a thiocyano group or a cyano group, a nitro group, a —

S(═

O)₂R′

group or a —

S(═

O)R′

group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 30 ring carbon alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent)].

4. A transition metal complex compound having a metal carbene bond represented by the following Formula (4):

[in Formula (4), a bond shown by a solid line (—

) represents a covalent bond, and a bond shown by an arrow (→

) represents a coordinate bond;

L¹⁰→

M represents a metal carbene bond;

M represents a metal atom of iridium (Ir) or platinum (Pt);

L¹⁰-L¹¹-L¹² represents a cross-linked tridentate ligand, and L¹⁹, L²⁰ and L²¹ each independently represent a unidentate ligand, a cross-linked bidentate ligand in which two of them are cross-linked or a cross-linked tridentate ligand in which at least two of L¹⁹ and L²⁰, L²⁰ and L²¹ and L¹⁹ and L²¹ are cross-linked;

at least one of L¹⁰, L¹¹ and L¹² may be cross-linked with at least one of L¹⁹, L²⁰ and L²¹;

i, j and k each represent an integer of 0 to 1, and 1+i+j represents a valence of metal M;

L¹² represents a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a divalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a divalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a divalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkylene group having 3 to 50 ring carbon atoms which may have a substituent, an alkylene group having 1 to 30 carbon atoms which may have a substituent, an alkenylene group having 2 to 30 carbon atoms which may have a substituent or an aralkylene group having 7 to 40 carbon atoms which may have a substituent;

L¹⁰ represents a monovalent group having carbene carbon which may have a substituent;

L¹¹ represents a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a divalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent or a divalent group having carbene carbon which may have a substituent;

L¹⁹ and L²⁰ each independently represent a monovalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a monovalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a monovalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a monovalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent or an aralkyl group having 7 to 40 carbon atoms which may have a substituent;

when L¹⁹ and L²⁰, L¹⁹ and L²¹ or L²⁰ and L²¹ are cross-linked, it is a divalent group of each group described above, and when L¹⁹ and L²⁰ and L¹⁹ and L²¹ are cross-linked and when L¹⁹ and L²⁰ and L²⁰ and L²¹ are cross-linked, it is a trivalent group of each group described above;

L²¹ represents a ligand comprising a heterocycle having 3 to 30 ring carbon atoms which may have a substituent, carboxylic acid ester having 1 to 30 carbon atoms which may have a substituent, carboxylic amide having 1 to 30 carbon atoms, amine which may have a substituent, phosphine which may have a substituent, isonitrile which may have a substituent, ether having 1 to 30 carbon atoms which may have a substituent, thioether having 1 to 30 carbon atoms which may have a substituent or a double bond-containing compound having 1 to 30 carbon atoms which may have a substituent;

when L¹⁹ and L²¹ or L²⁰ and L²¹ are cross-linked, it is a monovalent group of each ligand described above, and when L¹⁹ and L²¹ and L²⁰ and L²¹ are cross-linked, it is a divalent group of each ligand described above].

9. The transition metal complex compound having a metal carbene bond as described in claim 4, wherein a L¹⁰L¹¹L¹²M part in Formula (4) has a structure represented by the following Formula (10):

[in Formula (10), R⁵¹ to R⁶⁰ each independently represent a hydrogen atom, a halogen atom, a thiocyano group or a cyano group, a nitro group, a —

S(═

O)₂R′

group or a —

S(═

O)R′

group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 30 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 ring carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 ring carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms, and they may be cross-linked;

(R′

each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent)].

5. A transition metal complex compound having a metal carbene bond represented by the following Formula (5):

[in Formula (5), a bond shown by a solid line (—

) represents a covalent bond, and a bond shown by an arrow (→

) represents a coordinate bond;

L¹⁴→

M represents a metal carbene bond;

M represents a metal atom of iridium (Ir) or platinum (Pt);

L¹³-L¹⁴-L¹⁵ represents a cross-linked tridentate ligand, and L¹⁹, L²⁰ and L²¹ each independently represent a unidentate ligand, a cross-linked bidentate ligand in which two of them are cross-linked or a cross-linked tridentate ligand in which at least two of L¹⁹ and L²⁰, L²⁰ and L²¹ and L¹⁹ and L²¹ are cross-linked;

at least one of L¹³, L¹⁴ and L¹⁵ may be cross-linked with at least one of L¹⁹, L²⁰ and L²¹;

i, j and k each represent an integer of 0 to 1, and 1+i+j represents a valence of metal M;

L¹⁵ represents a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a divalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a divalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a divalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkylene group having 3 to 50 ring carbon atoms which may have a substituent, an alkylene group having 1 to 30 carbon atoms which may have a substituent, an alkenylene group having 2 to 30 carbon atoms which may have a substituent or an aralkylene group having 7 to 40 carbon atoms which may have a substituent;

L¹⁴ represents a monovalent group having carbene carbon which may have a substituent;

L¹³ represents a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a monovalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent or a divalent group having carbene carbon which may have a substituent;

L¹⁹ and L²⁰ each independently represent a monovalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a monovalent heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, a monovalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a monovalent hydrocarbon group containing amino group or hydroxyl group which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent or an aralkyl group having 7 to 40 carbon atoms which may have a substituent;

when L¹⁹ and L²⁰, L¹⁹ and L²¹ or L²⁰ and L²¹ are cross-linked, it is a divalent group of each group described above, and when L¹⁹ and L²⁰ and L¹⁹ and L²¹ are cross-linked and when L¹⁹ and L²⁰ and L²⁰ and L²¹ are cross-linked, it is a trivalent group of each group described above;

L²¹ represents a ligand comprising a heterocycle having 3 to 30 ring carbon atoms which may have a substituent, carboxylic acid ester having 1 to 30 carbon atoms which may have a substituent, carboxylic amide having 1 to 30 carbon atoms, amine which may have a substituent, phosphine which may have a substituent, isonitrile which may have a substituent, ether having 1 to 30 carbon atoms which may have a substituent, thioether having 1 to 30 carbon atoms which may have a substituent or a double bond-containing compound having 1 to 30 carbon atoms which may have a substituent;

when L¹⁹ and L²¹ or L²⁰ and L²¹ are cross-linked, it is a monovalent group of each ligand described above, and when L¹⁹ and L²¹ and L²⁰ and L²¹ are cross-linked, it is a divalent group of each ligand described above].

10. The transition metal complex compound having a metal carbene bond as described in claim 5, wherein a L¹³L¹⁴L¹⁵M part in Formula (5) has a structure represented by the following Formula (11):

[in Formula (11), R⁶¹ to R⁷⁰ each independently represent a hydrogen atom, a halogen atom, a thiocyano group or a cyano group, a nitro group, a —

S(═

O)₂R′

group or a —

S(═

O)R′

group, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 30 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 ring carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 ring carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms, and they may be cross-linked;

(R′

each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms which may have a substituent, a cycloalkyl group having 3 to 50 ring carbon atoms which may have a substituent, an aralkyl group having 7 to 40 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, a heterocyclic group having 3 to 30 ring carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 30 ring carbon atoms which may have a substituent, an alkylamino group having 3 to 30 carbon atoms which may have a substituent, an arylamino group having 6 to 30 carbon atoms which may have a substituent, an alkylsilyl group having 3 to 30 carbon atoms which may have a substituent, an arylsilyl group having 6 to 30 carbon atoms which may have a substituent or a carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent)].