Fluorinated organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9799838-B2
Application number	US-201615177906-A
Country	US
Kind code	B2
Filing date	Jun 9, 2016
Priority date	Oct 8, 2014
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

Novel ligands for metal complex compounds that are useful as a phosphorescent emitter in organic light emitting devices that incorporate fluorinated side chains in the ligands are disclosed. Such metal complex has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring, In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

First claim

We claim:

1. A composition comprising a first compound having the formula of M(L 1 ) x (L 2 ) y (L 3 ) z ;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein L 1 , L 2 , and L 3 can be the same or different;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of:

wherein R a , R b , R c , and R d independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R a , R b , R c , and R d are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a ring or form a multidentate ligand;
wherein at least one of the R a , R b , R c , and R d includes at least one R, wherein R is selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
wherein each of the at least one R is directly bonded to an aromatic ring;
wherein in each of the at least one R, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring; and
wherein when one of L 1 , L 2 , and L 3 is

 then at least one of the other L 1 , L 2 , and L 3 is different.

2. The composition of claim 1 , wherein the first compound is capable of emitting light from a triplet excited state to a ground singlet state at room temperature.

3. The composition of claim 1 , wherein the first compound is a metal coordination complex having a metal-carbon bond.

4. The composition of claim 1 , wherein C having an F attached thereto is separated by at least two carbon atoms from the aromatic ring.

5. The composition of claim 1 , wherein C having an F attached thereto is separated by at least three carbon atoms from the aromatic ring.

6. The composition of claim 1 , wherein each of the at least one R contains at least one CF 3 group.

7. The composition of claim 1 , wherein the first compound has the formula of Ir(L 1 ) 2 (L 2 ), wherein L 1 has the formula selected from the group consisting of:

and
wherein L 2 has the formula:

8. The composition of claim 7 , wherein L 2 has the formula:

wherein R e , R f , R h , and R i are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;
wherein at least one of R e , R f , R h , and R i has at least two carbon atoms;
wherein R g is selected from group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

9. The composition of claim 1 , wherein L 1 and L 2 are different and each independently selected from the group consisting of:

10. The composition of claim 1 , wherein L 1 and L 2 are each independently selected from the group consisting of:

11. The composition of claim 1 , wherein the first compound has the formula of Pt(L 1 ) 2 or Pt(L 1 )(L 2 ).

12. The composition of claim 1 , wherein at least one of R a , R b , R c , and R d includes an alkyl or cycloalkyl group that includes CD, CD 2 , or CD 3 , wherein D is deuterium.

13. The composition of claim 1 , wherein L 1 , L 2 , and L 3 are each independently selected from the group consisting of:

L A1 through L A41 , each

represented by the formula

wherein

in L A1 , R = R A1 , in L A2 , R = R A2 ,

in L A3 , R = R A3 , in L A4 , R = R A4 ,

in L A5 , R = R A5 , in L A6 , R = R A6 ,

in L A7 , R = R A7 , in L A8 , R = R A8 ,

in L A9 , R = R A9 , in L A10 , R = R A10 ,

in L A11 , R = R A11 , in L A12 , R = R A12 ,

in L A13 , R = R A13 , in L A14 , R = R A14 ,

in L A15 , R = R A15 , in L A16 , R = R A16 ,

in L A17 , R = R A17 , in L A18 , R = R A18 ,

in L A19 , R = R A19 , in L A20 , R = R A20 ,

in L A21 , R = R A21 , in L A22 , R = R A22 ,

in L A23 , R = R A23 , in L A24 , R = R A24 ,

in L A25 , R = R A25 , in L A26 , R = R A26 ,

in L A27 , R = R A27 , in L A28 , R = R A28 ,

in L A29 , R = R A29 , in L A30 , R = R A30 ,

in L A31 , R = R A31 , in L A32 , R = R A32 ,

in L A33 , R = R A33 , in L A34 , R = R A34 ,

in L A35 , R = R A35 , in L A36 , R = R A36 ,

in L A37 , R = R A37 , in L A38 , R = R A38 ,

in L A39 , R = R A39 , in L A40 , R = R A40 ,

and in L A41 , R = R A41 ;,

L A42 through L A82 , each

represented by the formula

wherein

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Yeager Walter
• Xia Chuanjun

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1033

  with oxygen · CPC title

• C07F15/0033

  Iridium compounds · CPC title