Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10566546-B2
Application number	US-201514791971-A
Country	US
Kind code	B2
Filing date	Jul 6, 2015
Priority date	Jul 14, 2014
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

A compound having a structure of Formula 1:

is disclosed. In Formula 1, each one of X 1 to X 16 is independently CR or N; at least two adjacent of X 1 to X 16 are CR; at least one pair of adjacent Rs is

fused to one of the Ring A, Ring B, Ring C, or Ring D; each instance of Y 1 , Y 2 , Y 3 , and Y 4 is independently CR 1 or N; each instance of Z is independently CR 2 R 3 , NR 4 , O, S or Se; each instance of R, R 1 , R 2 , R 3 , and R 4 are independently selected from a variety of substituents; and any adjacent substituents of R, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring. Formulations and devices, such as an OLEDs, that include the compound of Formula 1 are also described.

First claim

We claim:

1. A compound having a structure of Formula 1:

wherein each one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 is independently selected from the group consisting of CR and N,
wherein at least two adjacent of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 are CR;
wherein at least one pair of adjacent Rs is

fused to one of the Ring A, Ring B, Ring C, or Ring D;
wherein each instance of Y 1 , Y 2 , Y 3 , and Y 4 is independently selected from the group consisting of CR 1 and N;
wherein each instance of Z is independently selected from the group consisting of CR 2 R 3 , NR 4 , O, S and Se;
wherein each instance of R, R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substituents of R, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring; and
wherein at least one of the following is true:
(i) at least one of X 1 to X 16 is N;
(ii) at least one of Y 1 to Y 4 is N;
(iii) at least one of Y 1 to Y 4 is CR 1 where R 1 is aryl or heteroaryl, which may be further substituted by a moiety selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
(iv) wherein Ring A, Ring B, Ring C, and Ring D each include

fused thereto, and at least one Z is different from at least one other Z.

2. The compound of claim 1 , wherein at least one Z is CR 2 R 3 .

3. The compound of claim 1 , wherein at least one Z is NR 4 .

4. The compound of claim 1 , wherein at least one Z is selected from the group consisting of O, S and Se.

5. The compound of claim 1 , wherein at least one of options (ii), (iii), and (iv) is true, and each one of X 1 to X 16 is CR.

6. The compound of claim 1 , wherein at least one of options (iii) and (iv) is true, and each one of X 1 to X 16 is CR, and each one of Y 1 to Y 4 is CR 1 .

7. The compound of claim 1 , wherein at least one of options (i), (ii), and (iii) is true, and at least two pairs of adjacent Rs are

which can be the same or different.

8. The compound of claim 7 , wherein at least one of options (i), (ii), and (iii) is true, and one pair of adjacent Rs on Ring A, and one pair of adjacent Rs on Ring D is

9. The compound of claim 7 , wherein at least one of options (i), (ii), and (iii) is true, and one pair of adjacent Rs on Ring A is

and one pair of adjacent Rs on Ring B is

10. The compound of claim 1 , wherein at least three pairs of adjacent Rs are

which can be same or different.

11. The compound of claim 1 , wherein option (iv) is met.

12. A device comprising one or more organic light-emitting devices, at least one of the one or more organic light emitting devices comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a structure of Formula 1:

wherein each one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 is independently selected from the group consisting of CR and N,
wherein at least two adjacent of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 are CR;
wherein at least one pair of adjacent Rs is

fused to one of the Ring A, Ring B, Ring C, or Ring D;
wherein each instance of Y 1 , Y 2 , Y 3 , and Y 4 is independently selected from the group consisting of CR 1 and N;
wherein each instance of Z is independently selected from the group consisting of CR 2 R 3 , NR 4 , O, S and Se;
wherein each instance of R, R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof combinations thereof;
wherein any adjacent substituents of R, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring; and
wherein at least one of the following is true:
(i) at least one of X 1 to X 16 is N;
(ii) at least one of Y 1 to Y 4 is N;
(iii) at least one of Y 1 to Y 4 is CR 1 where R 1 is aryl or heteroaryl, which may be further substituted by a moiety selected from the group consisting of hydrogen, deuterium, halide, alkyl, haloalkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, thioalkoxy, aryloxy, thioaryloxy, amino, arylamino, diarylamino, carbazolyl, silyl, halosilyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
(iv) wherein Ring A, Ring B, Ring C, and Ring D each include

fused thereto, and at least one Z is different from at least one other Z.

13. The device of claim 12 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

14. The device of claim 12 , wherein the organic layer further comprises an emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate, selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carb

Assignees

• Universal Display Corp

Inventors

• Kwong Raymond
• Lam Sze Kui
• Lee Chi Hang

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07D209/94

  containing carbocyclic rings other than six-membered · CPC title

• C09K2211/185

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

• H01L51/0072 Primary

  Electricity · mapped topic

• H01L51/0085

  Electricity · mapped topic