# US 9,040,749 B2 · Borazine derivatives

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- Number: US 9,040,749 B2
- Document ID: US9040749B2
- Status: Granted
- Kind: B2
- Application number: 14/006,078
- Filed: 2012-03-16
- Published: 2014-03-27
- Granted: 2015-05-26
- Earliest claimed: 2011-03-18
- Assignees: Université De Namur; UCL Business PLC
- Applicants: Davide Bonifazi; Simon Kervyn De Meerendre; Franco Cacialli; Oliver Fenwick
- Inventors: Davide Bonifazi; Simon Kervyn De Meerendre; Franco Cacialli; Oliver Fenwick
- Web page: https://patentgrep.com/patent/US9040749B2

## CPC

- C07F 5/05: Cyclic compounds having at least one ring containing boron but no carbon in the ring
- H10K 85/60: Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence)
- H10K 85/658: {Organoboranes}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/135: comprising mobile ions
- 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

Borazine derivatives are used in the manufacture of electronic devices, in particular electroluminescent and semiconductor devices. More specifically, stable borazine derivatives include boron atoms substituted by aryl groups used in one or more layers of an electroluminescent or a semiconductor device, in particular in the emissive layer of organic light-emitting devices (OLED).

## Claims

### Claim 1

A borazine derivative represented by the following formula:
wherein the substituents R4 to R18 are the same or different from each other;
wherein each of R4 to R18 is independently selected from the group consisting of: hydrogen; linear or branched saturated alkyl group; linear or branched unsaturated alkyl group; cycloalkyl group; aryl group; aralkyl group; heteroaryl group; acyl group; hydroxyl; alkoxy group; aryloxy group; acyloxy group; amino group; alkylamino group; arylamino group; acylamino group; cyano group; carboxyl group; thio group; aminocarbonyl group; carbamoyl group, aryloxycarbonyl group, phenoxycarbonyl group, alkoxycarbonyl group and halogen;
wherein R4, R8, R9, R13, R14 and R18 cannot simultaneously be selected to be hydrogen;
wherein R4 to R8 and R14 to R18 cannot simultaneously be selected to be fluorine;
wherein the substituents R19 to R27 are the same or different from each other;
wherein each of R19 to R27 is independently selected from the group consisting of:
hydrogen; linear or branched saturated alkyl group; linear or branched unsaturated alkyl group; cycloalkyl group; aryl group; aralkyl group; heteroaryl group; acyl group; hydroxyl; alkoxy group; aryloxy group; acyloxy group; amino group; alkylamino group; arylamino group; acylamino group; cyano group; carboxyl group; thio group; aminocarbonyl group; carbamoyl group, aryloxycarbonyl group, phenoxycarbonyl group, alkoxycarbonyl group and halogen;
wherein at least one substituent selected from the group of R6, R11 and R16 is independently selected from the group consisting of linear or branched saturated alkyl groups; and
wherein at least two substituents selected from the group of R4, R8, R9, R13, R14 and R18 are independently selected from the group consisting of linear saturated alkyl groups and branched saturated alkyl groups.

### Claim 2 (depends on 1)

A derivative according to claim 1, wherein at least one substituent selected from the group of R22, R23, R24, R25, R26 and R27 is independently selected to be hydrogen.

### Claim 3 (depends on 1)

A derivative according to claim 1, wherein at least one substituent selected from the group of R19, R20 and R21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups.

### Claim 4 (depends on 1)

A derivative according to claim 1, able to emit in the UV region with a quantum yield above 0.05.

### Claim 5 (depends on 1)

A derivative according to claim 1, wherein at least one substituent selected from the group of R6, R11 and R16 is independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 6 carbon atoms.

### Claim 6 (depends on 1)

A derivative according to claim 1, wherein at least one substituent selected from the group of R6, R11 and R16 is independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 4 carbon atoms.

### Claim 7 (depends on 1)

A derivative according to claim 1, wherein at least one substituent selected from the group of R6, R11 and R16 is independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 3 carbon atoms.

### Claim 8 (depends on 1)

A derivative according to claim 1, wherein at least two substituents selected from the group of R4, R8, R9, R13, R14 and R18 are independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 6 carbon atoms.

### Claim 9 (depends on 1)

A derivative according to claim 1, wherein at least two substituents selected from the group of R4, R8, R9, R13, R14 and R18 are independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 4 carbon atoms.

### Claim 10 (depends on 1)

A derivative according to claim 1, wherein at least two substituents selected from the group of R4, R8, R9, R13, R14 and R18 are independently selected from the group consisting of linear or branched saturated alkyl groups with 1 to 3 carbon atoms.

### Claim 11 (depends on 3)

A derivative according to claim 3, wherein at least one substituent selected from the group of R19, R20 and R21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups with 1 to 12 carbon atoms.

### Claim 12 (depends on 3)

A derivative according to claim 3, wherein at least one substituent selected from the group of R19, R20 and R21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups with 1 to 6 carbon atoms.

### Claim 13 (depends on 3)

A derivative according to claim 3, wherein at least one substituent selected from the group of R19, R20 and R21 is independently selected from the group consisting of hydrogen, and linear or branched saturated alkyl groups with 1 to 3 carbon atoms.