# US 12,120,952 B2 · Compound, light-emitting material and light-emitting element

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- Number: US 12,120,952 B2
- Document ID: US12120952B2
- Status: Granted
- Kind: B2
- Application number: 16/488,374
- Filed: 2018-02-23
- Published: 2020-07-23
- Granted: 2024-10-15
- Earliest claimed: 2017-02-24
- Assignees: Kyulux, Inc.
- Applicants: Kyushu University, National University Corporation; Kyulux, Inc.
- Inventors: Hajime Nakanotani; Hiroki Noda; Chihaya Adachi; Naoto Notsuka; Yoshitake Suzuki
- Web page: https://patentgrep.com/patent/US12120952B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C09K 11/06: containing organic luminescent materials
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1018: Heterocyclic compounds
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Using a compound represented by a general formula (A)m-L-(D)n, a light-emitting device having a high emission efficiency can be provided. L is an (m+n)-valent aromatic linking group; A is a group having a positive Hammett's σp value; D is a group having a negative Hammett's σp value; m is an integer of 1 or more; n is an integer of 2 or more. Two of plural D's differ in point of the substituent condition at specific aromatic rings.

## Claims

### Claim 1

A compound represented by the following general formula (10):
wherein A1 represents a cyano group; R1 to R5 each independently represent a hydrogen atom or a group having a negative Hammett's σp value; at most one of R1 to R5 is a hydrogen atom; and for the R1 to R5 groups having a negative Hammett's σp value, two of the negative Hammett's σp-value groups have a different structure but have a common aromatic ring containing an atom bonding to the benzene ring of the general formula (10) in which the common aromatic ring of at least one of the two is substituted with a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a cyclic structure may be formed by the common aromatic ring in combination with the substituted or unsubstituted aryl group or the substituted or unsubstituted alkyl group.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the two of the negative Hammett's σp value groups are a group containing carbazole structure in which the nitrogen atom bonds to the benzene ring in the general formula (10) via a single bond, and R1 and R5 each are a group having a negative Hammett's σp value.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the two of the negative Hammett's σp value groups differ from each other in point of at least one condition of the number of the substituents on the aromatic ring, the substitution site of the aromatic ring substituted with the substituent, and the structure of the substituent on the aromatic ring.

### Claim 4 (depends on 3)

The compound according to claim 3, wherein the two of the negative Hammett's σp value groups are the combination of R2 and R5.

### Claim 5 (depends on 3)

The compound according to claim 3, wherein the two of the negative Hammett's σp value groups are the combination of R1 and R4.

### Claim 6 (depends on 1)

A light-emitting material containing the compound of claim 1.

### Claim 7 (depends on 1)

A light-emitting device containing the compound of claim 1.

### Claim 8 (depends on 7)

The light-emitting device according to claim 7 wherein a light-emitting layer contains the compound and a host material.

### Claim 9 (depends on 7)

The light-emitting device according to claim 7 configured to emit delayed fluorescence.