Platinum complex and light emitting device

• US 7,442,797 B2
• Filed: 10/27/2004
• Issued: 10/28/2008
• Est. Priority Date: 11/04/2003
• Status: Active Grant

• Current Assignee: Takasago International Corporation
• Original Assignee: Takasago International Corporation
• Inventors: Hori, Yoji, Itoh, Hisanori, Iwata, Takeshi, Matsushima, Yoshimasa, Nakayama, Yuji
• Primary Examiner(s): NAZARIO GONZALEZ, PORFIRIO
• Application Number:
  US10/578,237
• Publication Number:
  US 20070103060A1
• Time in Patent Office: 1,462 Days
• Field of Search: 546/2, 546/6, 546/13, 546/14, 313/504
• US Class Current: 546/6
• CPC Class Codes: C07D 213/06 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
• CPC Class Codes: C07D 213/30 Oxygen atoms
• CPC Class Codes: C07D 213/53 Nitrogen atoms
• CPC Class Codes: C07D 213/64 attached in position 2 or 6
• CPC Class Codes: C07D 213/74 Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• CPC Class Codes: C07D 277/28 Radicals substituted by nitrogen atoms
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1096 containing other heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• 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

Abstract

Provision of a novel platinum complex which is useful as a material for a light-emitting device of good light emission characteristic and light emission efficiency, and a novel light-emitting material that may be utilized in various fields.

A platinum complex represented by the following general formula (1):

(in which two rings of ring A, ring B, ring C, and ring D represent nitrogen-containing heterocyclic rings which may have a substituent and the remaining two rings of them represent aryl rings or hetero aryl rings which may have a substituent, the ring A and the ring B, the ring A and the ring C or/and the ring B and the rind D may form condensed rings. Two of X¹, X², X³, and X⁴ represent nitrogen atoms coordination bonded to a platinum atom and the remaining two of them represent carbon atoms or nitrogen atoms. Q¹, Q², and Q³ each represents a bond, oxygen atom, sulfur atom or bivalent group, two of Z¹, Z², Z³, and Z⁴ represent coordination bonds, and the remaining two of them represent covalent bonds, oxygen atoms or sulfur atoms), and a light-emitting device containing the platinum complex.

Claims

1. A platinum complex represented by the following general formula (1):

2. A platinum complex according to claim 1, wherein, in the general formula (1), a bivalent atom (group) represented by each of Q¹, Q², and Q³ is —

(CR¹R²)_n1—

, —

O(CR¹R²)_n1O—

, —

(O)_n2C(═

O)(O)_n3—

, oxygen atom, sulfur atom, —

NR³—

, —

BR^3a—

, —

S(═

O)—

, —

SO₂—

, —

O(SO₂)O—

, —

Si(R⁴R⁵)—

, —

OSi(R⁴R⁵)O—

, or —

C(═

CR^aR^b)—

, (where R¹ and R² each represent independently hydrogen atom, alkyl group, aralkyl group, aryl group, or alkoxy group;

n1 represents an integer of 1 to 3, and n2 and n3 each represent independently an integer of 0 or 1;

R³ represents hydrogen atom, alkyl group, aralkyl group, or aryl group, R^3a represents alkyl group, aralkyl group, or aryl group;

R⁴ and R⁵ each represent independently alkyl group, aralkyl group or aryl group;

R^a and R^b each represent independently hydrogen atom, alkyl group, aralkyl group, aryl group, or cyano group; and

R¹ and R², R⁴ and R⁵, or R^a and R^b may join to each other to form a ring which may contain a hetero atom in the ring together with the atom substituted with each of them).

3. A platinum complex according to claim 1, wherein two rings of the ring A, ring B, ring C and ring D of the compound represented by the general formula (1) are 5-membered or 6-membered nitrogen-containing heterocyclic rings which may have a substituent, and one or two 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocyclic ring may be condensed to said ring to form condensed rings.

4. A platinum complex according to claim 1, wherein two of the rings of the ring A, ring B, ring C, and the ring D of the compound represented by the general formula (1) are nitrogen-containing heterocyclic rings which may have substituent(s) selected from the group consisting of pyridine ring, diazine ring, triazine ring, pyrrole ring, diazole ring, triazole ring, thiazole ring, thiadiazole ring, oxazole ring, oxadiazole ring, benzopyridine ring, benzothiazine ring, and benzopyrrole group which may have substituent(s) respectively.

5. A platinum complex according to claim 1, wherein two rings of the ring A, ring B, ring C, and ring D of the compound represented by the general formula (1) are nitrogen-containing heterocyclic rings which may have substituent(s) and the remaining two rings are 6-membered aromatic hydrocarbon rings or aromatic heterocyclic rings, or 5-membered aromatic heterocyclic rings which may have substituent(s), which are aryl rings or heteroaryl rings where one or two 5- or 6-membered aromatic hydrocarbon rings or aromatic heterocyclic rings may be condensed to said rings to form condensed rings.

6. A platinum complex according to claim 1, wherein two rings of the ring A, ring B, ring C, and ring D of the compound represented by the general formula (1) are nitrogen-containing heterocyclic rings which may have substituent(s) and the remaining two rings are aryl rings or heteroaryl rings which may have substituent(s), selected from benzene ring, pyridine ring, diazine ring, triazine ring, pyrrole ring, diazole ring, furan ring, thiophene ring, oxazole ring, and thiazole ring which may have a substituent respectively, or condensed rings where one or two 5- or 6-membered aromatic hydrocarbon rings or aromatic heterocyclic rings are condensed to said rings.

7. A platinum complex according to claim 1 represented by the following general formula (2):

8. A light-emitting device in which a light-emitting layer or plural thin organic compound layers containing a light-emitting layer are formed between a pair of electrodes, in which at least one layer is a layer containing at least one kind of platinum complexes represented by the general formula (1):

9. A light-emitting device according to claim 8, wherein the light-emitting device is an organic electroluminescence device.

10. A light-emitting device according to claim 8, wherein the platinum complex contained in at least one layer may function as a doping material in the light-emitting layer of the organic electroluminescence device.

16. A compound according to claim 10 represented by the following general formula (4):

11. A compound represented by the following general formula (3):

12. A compound according to claim 11, wherein two rings of the ring A, ring B, ring C and ring D of the compound represented by the general formula (3) are 5-membered or 6-membered nitrogen-containing heterocyclic rings which may have substituent(s), and one or two 5- or 6-membered aromatic hydrocarbon rings or aromatic heterocyclic rings may be condensed to said rings to form condensed rings.

13. A compound according to claim 11, wherein two rings of the ring A, ring B, ring C, and the ring D of the compound represented by the general formula (3) are nitrogen-containing heterocyclic rings which may have substituent(s), selected from the group consisting of a pyridine ring, diazine ring, triazine ring, pyrrole ring, diazole ring, triazole ring, thiazole ring, thiadiazole ring, oxazole ring, oxadiazole ring, benzopyridine ring, benzothiazine ring, and benzopyrrole group which may have substituent(s) respectively.

14. A compound according to claim 11, wherein two rings of the ring A, ring B, ring C, and ring D of the compound represented by the general formula (3) are nitrogen-containing heterocyclic rings which may have substituent(s) and the remaining two rings are 6-membered aromatic hydrocarbon rings or aromatic heterocyclic rings, or 5-membered aromatic heterocyclic rings which may have substituent(s), which are aryl rings or heteroaryl rings where one or two 5- or 6-membered aromatic hydrocarbon rings or aromatic heterocyclic rings may be condensed to said rings to form condensed rings.

15. A compound according to claim 11, wherein two rings of the ring A, ring B, ring C, and ring D of the compound represented by the general formula (3) are nitrogen-containing heterocyclic rings which may have substituent(s) and the remaining two rings are aryl rings or heteroaryl rings which may have substituent(s), selected from benzene ring, pyridine ring, diazine ring, triazine ring, pyrrole ring, diazole ring, furan ring, thiophene ring, oxazole ring, and thiazole ring which may have substituent(s) respectively, or condensed rings where one or two 5- or 6-membered aromatic hydrocarbon rings or aromatic heterocyclic rings are condensed to said rings.