Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2016013422-A1
Application number	US-201514791971-A
Country	US
Kind code	A1
Filing date	Jul 6, 2015
Priority date	Jul 14, 2014
Publication date	Jan 14, 2016
Grant date	—

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; and
wherein any adjacent substituents of R, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring.

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

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

4 . The compound of claim 1 , wherein Z is selected from the group consisting of 0, S and Se.

5 . The compound of claim 1 , wherein each one of X 1 to X 16 is CR.

6 . The compound of claim 1 , wherein 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 two pairs of adjacent Rs are

which can be the same or different.

8 . The compound of claim 7 , wherein 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 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 at least four pairs of adjacent Rs are

which can be same or different.

12 . The compound of claim 11 , wherein each

is attached to a different ring selected from the group consisting of Ring A, Ring B, Ring C, and Ring D.

13 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

14 . 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 and
wherein any adjacent substituents of R, R 1 , R 2 , R 3 , and R 4 are optionally joined or fused into a ring.

15 . The device of claim 14 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

16 . The device of claim 14

Assignees

• Universal Display Corp

Inventors

• Kwong Raymond
• Lam Sze Kui
• Lee Chi Hang

Classifications

• C09K2211/185

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07D209/94

  containing carbocyclic rings other than six-membered · CPC title

• H01L51/0085

  Electricity · mapped topic

• H01L51/0072 Primary

  Electricity · mapped topic