# US 12,193,327 B2 · Donor-acceptor type thermally activated delayed fluorescent materials based on imidazo[1,2-f]phenanthridine and analogues

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- Number: US 12,193,327 B2
- Document ID: US12193327B2
- Status: Granted
- Kind: B2
- Application number: 17/929,067
- Filed: 2022-09-01
- Published: 2023-03-02
- Granted: 2025-01-07
- Earliest claimed: 2017-05-19
- Assignees: Arizona Board of Regents on behalf of Arizona State University
- Applicants: Arizona Board of Regents on behalf of Arizona State University
- Inventors: Jian Li; Zhi-Qiang Zhu
- Web page: https://patentgrep.com/patent/US12193327B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07D 471/14: Ortho-condensed systems
- C07D 471/20: Spiro-condensed systems
- C07D 471/22: in which the condensed systems contains four or more hetero rings
- C07D 491/147: the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
- C07D 491/22: in which the condensed system contains four or more hetero rings
- C07D 495/14: Ortho-condensed systems
- C07D 495/22: in which the condensed system contains four or more hetero rings
- C09K 11/06: containing organic luminescent materials
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/20: Delayed fluorescence emission
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Donor-acceptor type thermally activated delayed fluorescent emitters based on imidazo[1,2-F]phenanthridine and analogues for full color displays and lighting applications.

## Claims

### Claim 1

A compound represented by General Formula I:
wherein:
each occurrence of Donor represents no substitution or represents a group of Formula A, provided that at least one Donor represents a group of Formula A:
wherein, in Formula A, * and #represent bonds to adjacent positions on General Formula I:
represents hydrogen, cyanide, halogen, hydroxy, amino, nitro, thiol, or substituted or unsubstituted: C1-C4 alkyl, alkoxy, or aryl; or two adjacent groups R4 together form a group of Formula B
wherein, in Formula B, ‡ and § represent bonds to adjacent positions on Formula A;
each U1 and U4 independently represents O, S, CRR′, SiRR′, or NAr*, where R and R′ each independently represents hydrogen, cyanide, halogen, hydroxy, amino, nitro, thiol, or optionally substituted C1-C4 alkyl, alkoxy, or aryl, and Ar* represents a substituted or unsubstituted: phenyl, pyridyl, naphthyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, imidazolyl, oxazolyl, or thiazolyl ring, and Ar* is optionally covalently bonded to V2 to form one or more 5-membered or 6-membered rings,
R1, R2, R3, and R5 each independently represents hydrogen, cyanide, halogen, hydroxy, amino, nitro, thiol, or substituted or unsubstituted; C1-C4 alkyl, alkoxy, or aryl, and
V2 represents N or substituted or unsubstituted C,
each X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, X16, X17, and X18 independently represents substituted or unsubstituted; C, N, Si, O, or S, valency permitting,
each n is independently an integer as permitted by valence, and
wherein at least one of the following conditions (i) and (ii) is true:
(i) at least two occurrences of Donor represent a group of Formula A; or
(ii) at least two adjacent groups R4 together form a group of Formula B.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound is represented by one of the following structures:
wherein:
R1, R2, R3, R4, and R5 each independently represents hydrogen, cyanide, halogen, hydroxy, amino, nitro, thiol, or substituted or unsubstituted C1-C4 alkyl, alkoxy, or aryl,
X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, X16, X17, X18, X19, X20, X21, and X22 each independently represents substituted or unsubstituted C, N, Si, O, or S, valency permitting,
V1, V2, V3, and V4 each independently represents substituted or unsubstituted C or N, valency permitting,
U1 and U2 each independently represents O, S, CRR′, SiRR′, or NAr*, where R and R′ each independently represents hydrogen, cyanide, halogen, hydroxy, amino, nitro, thiol, or optionally substituted C1-C4 alkyl, alkoxy, or aryl, and Ar* represents a substituted phenyl, pyridyl, naphthyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, imidazolyl, oxazolyl, or thiazolyl ring, and Ar* is optionally covalently bonded to V1, V2, V3, or V4 to form one or more 5-membered or 6-membered rings,
U3 and U4 each independently represents CR, SiR, or N, where R represents optionally substituted C1-C4 alkyl, alkoxy, aryl or heteroaryl, and
each n is independently an integer as permitted by valence.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound is represented by one of the following structures:

### Claim 4 (depends on 1)

An organic light emitting diode comprising the compound of claim 1.

### Claim 5 (depends on 4)

A light emitting device comprising the light emitting diode of claim 4.

### Claim 6 (depends on 2)

An organic light emitting diode comprising the compound of claim 2.

### Claim 7 (depends on 6)

A light emitting device comprising the light emitting diode of claim 6.

### Claim 8 (depends on 3)

An organic light emitting diode comprising the compound of claim 3.

### Claim 9 (depends on 8)

A light emitting device comprising the light emitting diode of claim 8.