Diamine compounds for phosphorescent diazaborole metal complexes and electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9859504-B2
Application number	US-201514673232-A
Country	US
Kind code	B2
Filing date	Mar 30, 2015
Priority date	Mar 31, 2014
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

The present disclosure generally relates to diamine compounds, which may be used as precursors in preparing diazaborole compounds and phosphorescent diazaborole metal complexes. The present disclosure also relates to diazaborole compounds, diazaborole metal complexes, and electroluminescent emission materials and electronic devices thereof. The present disclosure further relates to processes for preparing the diamine compounds and diazaborole metal complexes.

First claim

What is claimed is:

1. A compound of Formula 1 or Formula 2:

wherein
R 1 is selected from C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, and a 5 or 6 membered aryl or heteroaryl, each of which is optionally substituted with one or more substituents each independently selected from halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , aryl and heteroaryl; wherein R 2 and R 3 are each independently selected from hydrogen and C 1-6 alkyl;
Q is an optionally substituted, optionally fused 5 or 6 membered heterocyclic ring, wherein the dashed circle indicates the optional location of up to two optional double bonds in the ring; and
Q 1 , Q 2 and Q 3 , are each independently selected from CR 4 or N; wherein at least one of Q 1 , Q 2 and Q 3 is N; and each R 4 is independently selected from hydrogen, halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , optionally substituted C 1-20 alkyl, optionally substituted C 2-20 alkenyl, optionally substituted C 2-20 alkynyl, and optionally substituted 5 or 6 membered aryl or heteroaryl, and optionally two R 4 substituents from adjacent ring atoms are joined together to form an optionally substituted 5 or 6 membered aryl or heteroaryl ring; wherein R 2 and R 3 are defined as above;
Q 4 , Q 5 and Q 6 , are each independently selected from N, S, O, CR 4 and NR 5 , wherein at least one of Q 4 , Q 5 and Q 6 is selected from N, S, O and NR 5 ; wherein R 4 is defined as above and R 5 is defined according to R 1 above; with the proviso that when T is present then Q 4 is selected from C-T and N-T, and when T is absent Q is not a furo[2,3-C]pyridine group;
T is a tether group between rings Q and A of 1 to 3 atoms in length linked together in a linear chain, wherein the dashed lines between Q 4 atom and A ring indicates T is an optional group, and wherein T is selected from C, N, O, S, Si and B, each of which is optionally substituted with one or more substituents independently selected from hydrogen, halo, CN, NO 2 , ═O, C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , optionally substituted C 1-10 alkyl, optionally substituted C 2-10 alkenyl, optionally substituted C 2-10 alkynyl and optionally substituted 5 or 6 membered aryl or heteroaryl, and optionally fused with a 3-6 membered carbocycle or heterocycle; and wherein R 2 and R 3 are each independently defined as above,
A is a monocyclic or bicyclic 5 or 6 membered heterocyclic ring containing a donor atom D and a ring atom A 1 , and optionally having 1 or 2 additional ring heteroatoms selected from O, S and N, wherein the heterocyclic ring is optionally substituted with 1 to 3 substituents independently selected from hydrogen, halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , optionally substituted C 1-20 alkyl, optionally substituted C 2-20 alkenyl, optionally substituted C 2-20 alkynyl, and optionally substituted 5 or 6 membered aryl or heteroaryl; wherein R 2 and R 3 are each independently defined as above;
A 1 is selected from C, O, S, N, CR 8 , C(R 8 ) 2 and NR 9 ; wherein each R 8 is independently selected from hydrogen, halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , optionally substituted C 1-20 alkyl, optionally substituted C 2-20 alkenyl, optionally substituted C 2-20 alkynyl, optionally substituted 5 or 6 membered aryl or heteroaryl; wherein R 9 is selected from hydrogen, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, and a 5 or 6 membered aryl or heteroaryl, each of which can be optionally substituted with one or more substituents independently selected from halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , aryl and heteroaryl; and wherein R 2 and R 3 are defined as above; and
D is a donor atom selected from N, O, S, P, Se and Te.

2. The compound of claim 1 , wherein R 1 is selected from optionally substituted C 1-10 alkyl and optionally substituted monocyclic 5 or 6 membered aryl or heteroaryl.

3. The compound of claim 1 , wherein the compound is of Formula 1, wherein Q 1 , Q 2 and Q 3 are each independently selected from CR 4 or N; and wherein at least one of Q 1 , Q 2 and Q 3 is N.

4. The compound of claim 1 , wherein the compound is of Formula 2, wherein when T is present, Q 4 is selected from C-T and N-T.

5. The compound of claim 1 , wherein Q 4 , Q 5 and Q 6 , are each independently selected from N, S and CR 4 , and at least one of Q 4 , Q 5 and Q 6 is selected from N and S.

6. The compound of claim 5 , wherein Q 5 is S and Q 4 and Q 6 are CR 4 .

7. The compound of claim 1 , which is selected from a compound of Formula 2, wherein when T is absent, Q 4 , Q 5 and Q 6 , are each independently selected from N, S, CR 4 and NR 5 , wherein at least one of Q 4 , Q 5 and Q 6 is selected from N, S and NR 5 .

8. The compound of claim 1 , wherein T is a tether group provided by a linear chain of 1 to 3 atoms in length independently selected from —N(R 7 )—, —N(R 7 )—C(═O)—, —O—, —O—C(═O)—, —C(═O)—, —S—, —S(═O)—, —S(═O) 2 —, C 1-3 alkyl and C 2-3 alkenyl; wherein the C 1-3 alkyl and C 2-3 alkenyl are each optionally interrupted by a group selected from —N(R 7 )—, —N(R 7 )—C(═O)—, —O—, —O—C(═O)—, —C(═O)—, —S—, —S(═O)— and S(═O) 2 , and optionally substituted with one or more substituents independently selected from halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 1-10 alkylhalo, C 2-10 alkenylhalo and C 2-10 alkynylhalo, and optionally fused with a 3-6 membered carbocycle or heterocycle; and wherein R 7 is selected from hydrogen and C 1-10 alkyl.

9. The compound of claim 8 , wherein T is the optionally substituted, optionally fused C 1-3 alkyl.

10. The compound of claim 1 , wherein A is an optionally substituted monocyclic or bicyclic 5 or 6 membered heteroaryl ring.

11. The compound of claim 1 , wherein D is N.

12. The compound of claim 1 , wherein A is an optionally substituted pyridine group.

13. A compound of Formula 3 or Formula 4:

wherein
R 1 is selected from C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, and a 5 or 6 membered aryl or heteroaryl, each of which is optionally substituted with one or more substituents each independently selected from halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , aryl and heteroaryl; wherein R 2 and R 3 are each independently selected from hydrogen and C 1-6 alkyl;
Q is an optionally substituted, optionally fused 5 or 6 membered heterocyclic ring, wherein the dashed circle indicates the optional location of up to two optional double bonds in the ring; and
Q 1 , Q 2 and Q 3 , are each independently selected from CR 4 or N; wherein at least one of Q 1 , Q 2 and Q 3 is N; and each R 4 is independently selected from hydrogen, halo, CN, NO 2 , C(O)R 2 , OR 2 , OS(O) 2 R 2 , NR 2 R 3 , SR 2 , optionally substituted C 1-20 alkyl, optionally substituted C 2-20 alkenyl, optionally substituted C 2-20 alkynyl, and optionally substituted 5 or 6 membered aryl or heteroaryl, and optionally two R 4 substituents from adjacent ring atoms are joined together to form an optionally substituted 5 or 6 membered aryl or heteroaryl ring; wherein R 2 and R 3 are defined as above;
Q 4 , Q 5 and Q 6 , are each independently selected from N, S, O, CR 4 and NR 5 , wherein at least one of Q 4 , Q 5 and Q 6 is selected from N, S, O and NR 5 ; wherein R 4

Assignees

• Commw Scient Ind Res Org

Inventors

• Bilyk Alexander
• Bown Mark
• Wilson Anthony
• Ueno Kazunori

Classifications

• H01L51/5012

  Electricity · mapped topic

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• H01L51/5206

  Electricity · mapped topic

• H01L51/0068 Primary

  Electricity · mapped topic

• H01L51/5221

  Electricity · mapped topic