IP Library › Granted Patent US 10,700,292
Granted Patent B2
US 10,700,292 · App. 15/125,247 · Granted Jun 30, 2020

Metal complex and light emitting device using the same

Inventors: Kazuei Ohuchi (Tsukuba, JP); Kohei Asada (Tsukuba, JP); Shigeya Kobayashi (Osaka, JP)
Assignee: Sumitomo Chemical Company, Limited
H01L51/0085C07F15/0033C09K11/025C09K11/06H01L51/0039H01L51/0043C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/185H01L51/006H01L51/0052H01L51/0058H01L51/0067H01L51/5016H01L51/5056H01L51/56
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Quick Facts
Patent No.
US 10,700,292
App. No.
15/125,247
Granted
Jun 30, 2020
Kind
B2
Abstract

A metal complex is represented by the formula (1): In formula (1), M represents Ir or Pt, n 1 represents 1 to 3, n 2 represents 0 to 2, A 1 -G 1 -A 2 represents an anionic bidentate ligand, m 1 and m 2 represent 3 or 4, E 1 to E 4 represent a nitrogen atom or a carbon atom, R 1 and R 2 represent a substituent, R 1 and/or R 2 is represented by formula (2-1) or formula (2-2), Ring A represents an aromatic heterocyclic ring, Ring B represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and R 3 , R 3a , R 4a , R 5 and R 6 represent a substituent:

Claims (40)

1. A metal complex represented by the following formula (1-b):

in the formula (1-b),

M represents an iridium atom,

n 1 represents 3, n 2 represents 0,

A 1 -G 1 -A 2 is not present,

R 8 , R 9 , R 10 and R 11 each independently represent a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent, and the plurality of R 8 , R 9 , R 10 and R 11 may be the same or different at each occurrence, R 11 and R 10 may be combined to form a ring together with the carbon atoms to which they are attached, R 10 and R 9 may be combined to form a ring together with the carbon atoms to which they are attached, and R 9 and R 8 may be combined to form a ring together with the carbon atoms to which they are attached,

R 12 , R 13 , R 14 and R 15 each independently represent a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent, and the plurality of R 12 , R 13 , R 14 and R 15 may be the same or different at each occurrence, and R 11 and R 12 may be combined to form a ring together with the carbon atoms to which they are attached, R 12 and R 13 may be combined to form a ring together with the carbon atoms to which they are attached, R 13 and R 14 may be combined to form a ring together with the carbon atoms to which they are attached, and R 14 and R 15 may be combined to form a ring together with the carbon atoms to which they are attached, and

at least one of R 10 and R 14 is a group represented by the formula (2-1):

in the formula (2-1),

R 3 represents an alkyl group and this group optionally has a substituent,

R 5 represents a hydrogen atom or an alkyl group and this alkyl group optionally has a substituent, and the plurality of R 5 may be the same or different, and

R 4a represents an aryl group having no substituent or an aryl group having an alkyl group or a cycloalkyl group as a substituent and the alkyl group and the cycloalkyl group each optionally further have a substituent, and the plurality of R 4a may be the same or different.

2. The metal complex according to claim 1 , wherein the group represented by the formula (2-1) is a group represented by the following formula (2-3):

in the formula (2-3),

R 3 represents the same meaning as described above,

R 5 represents a hydrogen atom or an alkyl group and this alkyl group optionally has a substituent, and the plurality of R 5 may be the same or different,

R 6 represents a hydrogen atom, an alkyl group or a cycloalkyl group and these groups each optionally have a substituent, and the plurality of R 6 may be the same or different, and

R 7 represents a hydrogen atom, an alkyl group or a cycloalkyl group and these groups each optionally have a substituent, and the plurality of R 7 may be the same or different.

3. A metal complex represented by the following formula (1-c):

in the formula (1-c),

M represents an iridium atom or a platinum atom,

n 1 represents 1, 2 or 3, n 2 represents 0, 1 or 2, and n 1 +n 2 =3 when M is an iridium atom, while n 1 +n 2 =2 when M is a platinum atom,

A 1 -G 1 -A 2 represents an anionic bidentate ligand, G 1 represents an atomic group constituting a bidentate ligand together with A 1 and A 2 , A 1 and A 2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom and these atoms each may be an atom constituting a ring, and a plurality of A 1 -G 1 -A 2 which are present when n 2 is 2 may be the same or different,

R 8 , R 9 and R 11 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom and these groups each optionally have a substituent, and a plurality of R 8 , R 9 and R 11 which are present when n 1 is 2 or 3 may be the same or different at each occurrence, and R 9 and R 8 may be combined to form a ring together with the carbon atoms to which they are attached,

R 10 represents a group represented by the formula (2-1), and a plurality of R 10 which are present when n 1 is 2 or 3 may be the same or different,

E 5 and E 6 each independently represent a nitrogen atom or a carbon atom, and a plurality of E 5 and E 6 which are present when n 1 is 2 or 3 may be the same or different at each occurrence, and R 17 is not present when E 5 is a nitrogen atom, and R 18 is not present when E 6 is a nitrogen atom,

R 16 , R 17 and R 18 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom and these groups each optionally have a substituent, and a plurality of R 16 , R 17 and R 18 which are present when n 1 is 2 or 3 may be the same or different at each occurrence, and R 11 and R 16 may be combined to form a ring together with the carbon atom to which R 11 is attached and the nitrogen atom to which R 16 is attached, R 16 and R 17 may be combined to form a ring together with the nitrogen atom to which R 16 is attached and the carbon atom to which R 17 is attached, and R 17 and R 18 may be combined to form a ring together with the carbon atoms to which they are attached:

in the formula (2-1),

R 3 represents an alkyl group and this group optionally has a substituent,

R 5 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group and these groups each optionally have a substituent, and the plurality of R 5 may be the same or different, and

R 4a represents an aryl group having no substituent or an aryl group having an alkyl group or a cycloalkyl group as a substituent and the alkyl group and the cycloalkyl group each optionally further have a substituent, and the plurality of R 4a may be the same or different.

4. A composition comprising

the metal complex according to claim 1 , and

a polymer compound comprising a constitutional unit represented by the following formula (Y):

Ar Y1   (Y)

in the formula (Y), Ar Y1 represents an arylene group, a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are bonded directly to each other, and these groups each optionally have a substituent.

5. A composition comprising

the metal complex according to claim 1 , and

at least one material selected from the group consisting of a hole transporting material, a hole injection material, an electron transporting material, an electron injection material, a light emitting material, an antioxidant and a solvent.

6. A light emitting device comprising the metal complex according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 14, 2016
From: OHUCHI, KAZUEI; ASADA, KOHEI; KOBAYASHI, SHIGEYA
To: SUMITOMO CHEMICAL COMPANY, LIMITED
Reel/Frame 039732/0849 →
Priority Claims (1)
JP 2014-053075 · Mar 17, 2014 · national
Continuity (1)
Related Publication 20170077424A1 · Mar 16, 2017