# US 2018/0022990 A1 · Composition and light emitting device using the same

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- Number: US 2018/0022990 A1
- Document ID: US20180022990A1
- Status: Published application
- Kind: A1
- Application number: 15/547,962
- Filed: 2016-01-15
- Published: 2018-01-25
- Earliest claimed: 2015-02-03
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Sumitomo Chemical Company, Limited
- Inventors: Toshiaki SASADA; Takakazu SAITO
- Web page: https://patentgrep.com/patent/US20180022990A1

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 15/00: Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/342: {comprising iridium}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1074: containing more than three nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 2101/10: Triplet emission
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

Provided is a composition useful for producing a light emitting device in which the driving voltage is low. In particular, a composition containing a phosphorescent compound of formula (1) and a phosphorescent compound of formula (2) is provided, wherein the variable groups are as defined in the specification.

## Claims

### Claim at position 1

1-14. (canceled)

### Claim 15

A composition comprising a phosphorescent compound of formula (1) and a phosphorescent compound of formula (2),
wherein the maximum peak wavelength of the emission spectrum of the phosphorescent compound of formula (1) is 380 nm or more and less than 495 nm, and
the maximum peak wavelength of the emission spectrum of the phosphorescent compound of formula (2) is 495 nm or more and less than 750 nm:
wherein
M1 represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom,
n1 represents an integer of 1 or more, n2 represents an integer of 0 or more, provided that n1+n2 is 2 or 3, and n1+n2 is 3 when M1 is a ruthenium atom, a rhodium atom or an iridium atom, and n1+n2 is 2 when M1 is a palladium atom or a platinum atom,
E1 and E2 each independently is a carbon atom or a nitrogen atom, and at least one of E1 and E2 is a carbon atom,
the ring R1 is an optionally substituted 5-membered aromatic heterocyclic ring, and when a plurality of substituents are present, they can be the same or different and can be combined together to form a ring together with the atoms to which they are attached, and when a plurality of the rings R1 are present, they can be the same or different,
the ring R2 is an optionally substituted aromatic hydrocarbon ring or an optionally substituted aromatic heterocyclic ring, and when a plurality of substituents are present, they can be the same or different and can be combined together to form a ring together with the atoms to which they are attached, and when a plurality of the rings R2 are present, they can be the same or different,
the ligand constituted of the ring R1 and the ring R2 is a ligand constituted of atoms selected from the group consisting of a hydrogen atom, a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom, and at least one ring selected from the group consisting of the ring R1 and the ring R2 has a group represented by the formula (1-S), and
A1-G1-A2 is an anionic bidentate ligand, A1 and A2 each independently is a carbon atom, an oxygen atom or a nitrogen atom and these atoms can be an atom constituting a ring, G1 represents a single bond or an atomic group constituting the bidentate ligand together with A1 and A2, and when a plurality of A1-G1-A2 are present, they can be the same or different:
wherein
Ar1S is an aryl group optionally substituted with an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, wherein the alkyl group, the cycloalkyl group, the alkoxy group and the cycloalkoxy group each is optionally further substituted with a substituent,
n1S is an integer of 0 to 10, and
Ar2S is an arylene group optionally substituted with an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, wherein the alkyl group, the cycloalkyl group, the alkoxy group and the cycloalkoxy group each is optionally further substituted with a substituent, and when a plurality of Ar2S are present, they can be the same or different:
wherein
M2 is a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom,
n3 is an integer of 1 or more, n4 represents an integer of 0 or more, provided that n3+n4 is 2 or 3, and n3+n4 is 3 when M2 is a ruthenium atom, a rhodium atom or an iridium atom, and n3+n4 is 2 when M2 is a palladium atom or a platinum atom,
E4 is a carbon atom or a nitrogen atom,
the ring L1 is an optionally substituted 6-membered aromatic heterocyclic ring, and when a plurality of substituents are present, they can be the same or different and can be combined together to form a ring together with the atoms to which they are attached, and when a plurality of the rings L1 are present, they can be the same or different,
the ring L2 is an optionally substituted aromatic hydrocarbon ring or an optionally substituted aromatic heterocyclic ring, and when a plurality of substituents are present, they can be the same or different and can be combined together to form a ring together with the atoms to which they are attached, and when a plurality of the rings L2 are present, they can be the same or different,
the substituents which the ring L1 optionally has and the substituents which the ring L2 optionally has can be combined together to form a ring together with the atoms to which they are attached,
the ligand constituted of the ring L1 and the ring L2 is a ligand constituted of atoms selected from the group consisting of a hydrogen atom, a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom, and at least one ring selected from the group consisting of the ring L1 and the ring L2 is substituted with a group of formula (1-T), and
A3-G2-A4 is an anionic bidentate ligand, A3 and A4 each independently is a carbon atom, an oxygen atom or a nitrogen atom and these atoms can be an atom constituting a ring, G2 is a single bond or an atomic group constituting the bidentate ligand together with A3 and A4, and when a plurality of A3-G2-A4 are present, they can be the same or different:
wherein
Ar1T is an aryl group optionally substituted with an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, wherein the alkyl group, the cycloalkyl group, the alkoxy group and the cycloalkoxy group each is optionally further substituted with a substituent,
n1T is an integer of 0 to 10, and
Ar2T is an arylene group optionally substituted with an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, wherein the alkyl group, the cycloalkyl group, the alkoxy group and the cycloalkoxy group each is optionally further substituted with a substituent, and when a plurality of Ar2T are present, they can be the same or different.

### Claim 16 (depends on 15)

The composition according to claim 15, wherein the phosphorescent compound of formula (1) is a phosphorescent compound of formula (1-A):
wherein
M1, n1, n2, E1 and A1-G1-A2 represent the same meaning as described above,
E11A, E12A, E13A, E21A, E22A, E23A and E24A each independently is a nitrogen atom or a carbon atom, and when a plurality of E11A, E12A, E13A, E21A, E22A, E23A and E24A are present, they can be the same or different at each occurrence, and R11A, R12A and R13A can be present or not be present when each of E11A, E12A and E13A is a nitrogen atom, and R21A, R22A, R23A and R24A are not present when each of E21A, E22A, E23A and E24A is a nitrogen atom,
R11A, R12A, R13A, R21A, R22A, R23A and R24A each independently is 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 substituted amino group and each of these groups is optionally substituted with a substituent, and when a plurality of R11A, R12AR13A, R21A, R22A, R23A and R24A are present, they can be the same or different at each occurrence, and R11A and R12A,R12A and R13A, R21A and R22A, R22A and R23A, and R23A and R24A each can be combined together to form a ring together with the atoms to which they are attached, and at least one selected from the group consisting of R11A, R12A, R13A, R21A, R22A, R23A and R24A is a group of formula (1-S),
the ring R1A is a triazole ring or a diazole ring constituted of a nitrogen atom, E1, E11A E12A and E13A, and
the ring R2A represents a benzene ring, a pyridine ring or a pyrimidine ring constituted of two carbon atoms, E21A, E22A, E23A and E24A.

### Claim 17 (depends on 16)

The composition according to claim 16, wherein the phosphorescent compound of formula (1-A) is a phosphorescent compound of formula (1-A1), a phosphorescent compound of formula (1-A2), a phosphorescent compound of formula (1-A3) or a phosphorescent compound of formula (1-A4):
wherein
M1, n1, n2, R1A, R2A, R13A, R21A, R22A, R23A, R24A and A1-G1-A2 represent the same meaning as described above.

### Claim 18 (depends on 15)

The composition according to claim 15, wherein M1 is a ruthenium atom, a rhodium atom or an iridium atom and n1 is 3, or M1 is a palladium atom or a platinum atom and n1 is 2.

### Claim 19 (depends on 15)

The composition according to claim 15, wherein the phosphorescent compound of formula (2) is a phosphorescent compound of formula (2-B):
wherein
M2, n3, n4 and A3-G2-A4 represent the same meaning as described above,
E11B, E12B, E13B, E14B, E21B, E22B, E23B and E24B each independently is a nitrogen atom or a carbon atom, and when a plurality of E11B, E12B, E13B, E14B, E21B, E22B, E23B and E24B are present, they can be the same or different at each occurrence, and R11B, R12B, R13B, R14B, R21B, R22B, R23B, and R24B are not present when each of E11B, E12B, E13B, E14B, E21B, E22B, E23B and E24B is a nitrogen atom,
R11B, R12B, R13B, R14B, R21B, R22B, R23B and R24B each independently is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group and each of these groups is optionally substituted with a substituent, and when a plurality of R11B, R12B, R13B, R14B, R21B, R22B, R23B and R24B are present, they can be the same or different at each occurrence, and R11B and R12B, R12B and R13B, R13B and R14B, R11B and R21B, R21B and R22B, R22B and R23B, and R23B and R24B each can be combined together to form a ring together with the atoms to which they are attached, and at least one selected from the group consisting of R11B, R12B, R13B, R14B, R21B, R22B, R23B and R24B is the group of formula (1-T),
the ring L1B is a pyridine ring or a pyrimidine ring constituted of a nitrogen atom, a carbon atom, E11B, E12B, E13B and E14B, and
the ring L2B is a benzene ring, a pyridine ring or a pyrimidine ring constituted of two carbon atoms, E21B, E22B, E23B and E24B.

### Claim 20 (depends on 19)

The composition according to claim 19, wherein the phosphorescent compound of formula (2-B) is a phosphorescent compound of formula (2-B 1), a phosphorescent compound of formula (2-B2), a phosphorescent compound of formula (2-B3) or a phosphorescent compound of formula (2-B4):
wherein
M2, n3, n4, A3-G2-A4, R11B, R12B, R13B, R14B, R21B, R22B, R23B and R24B represent the same meaning as described above,
R15B, R16B, R17B and R18B each independently is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group or a monovalent heterocyclic group and each of these groups is optionally substituted with a substituent, and when a plurality of R15B, R16B, R17B and R18B are present, they can be the same or different at each occurrence, and R15B and R16B, R16B and R17B, and R17B and R18B each can be combined together to form a ring together with the atoms to which they are attached, and
at least one selected from the group consisting of R11B, R12B, R13B, R14B, R21B, R22B, R23B and R24B is the group of formula (1-T).

### Claim 21 (depends on 15)

The composition according to claim 15, wherein the group of formula (1-S) is a group of formula (1-S1):
wherein
n1S represents the same meaning as described above, and
R1S and R2S each independently is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group and each of these groups is optionally substituted with a substituent, and the plurality of R1S can be the same or different, and the plurality of R2S can be the same or different.

### Claim 22 (depends on 21)

The composition according to claim 21, wherein the group of formula (1-S1) is a group of formula (1-S1-1), a group of formula (1-S1-2), a group of formula (1-S1-3) or a group of formula (1-S1-4):
wherein
R11S, R12S, R13S, R14S, R15S, R16S, R17S, R18S, R19S, R20S, R21S, R22S, R23S, R24S and R25S each independently is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group and each of these groups is optionally substituted with a substituent.

### Claim 23 (depends on 15)

The composition according to claim 15, wherein the group of formula (1-T) is a group of formula (1-T1):
wherein
n1T represents the same meaning as described above, and
R1T and R2T each independently is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group and each of these groups is optionally substituted with a substituent, and the plurality of R1T can be the same or different, and the plurality of R2T can be the same or different.

### Claim 24 (depends on 23)

The composition according to claim 23, wherein the group of formula (1-T1) is a group of formula (1-T1-1), a group of formula (1-T1-2), a group of formula (1-T1-3) or a group of formula (1-T 1-4):
wherein
R11T, R12T, R13T, R14T, R15T, R16T, R17T, R18T, R19T, R20T, R21T, R22T, R23T, R24T and R25T each independently is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group and each of these groups is optionally substituted with a substituent.

### Claim 25 (depends on 15)

The composition according to claim 15, further comprising a compound of formula (H-1):
wherein
ArH1 and ArH2 each independently is an optionally substituted aryl group or an optionally substituted monovalent heterocyclic group,
nH1 and nH2 each independently is 0 or 1, and when a plurality of nH1 are present, they can be the same or different, and the plurality of nH2 can be the same or different,
nH3 is an integer of 0 or more,
LH1 is an arylene group, a divalent heterocyclic group or a group represented by —[C(RH11)2]nH11- and each of these groups is optionally substituted with a substituent, and when a plurality of LH1 are present, they can be the same or different,
nH11 is an integer of 1 to 10, and RH11 is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group and each of these groups is optionally substituted with a substituent, and the plurality of RH11 can be the same or different and can be combined together to form a ring together with the carbon atoms to which they are attached,
LH2 is a group represented by —N(-LH21-RH21)—, and when a plurality of LH2 are present, they can be the same or different, and
LH21 is a single bond, an arylene group or a divalent heterocyclic group and each of these groups is each optionally substituted with a substituent, and RH21 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group and each of these groups is optionally substituted with a substituent.

### Claim 26 (depends on 15)

The composition according to claim 15, further comprising a polymer compound comprising a constitutional unit of formula (Y):
ArY1 (Y)
wherein ArY1 is 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 each of these groups is optionally substituted with a substituent.

### Claim 27 (depends on 15)

The composition according to claim 15, further comprising 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.

### Claim 28 (depends on 15)

A light emitting device comprising the composition according to claim 15.