Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11322691-B2
Application number	US-201816043522-A
Country	US
Kind code	B2
Filing date	Jul 24, 2018
Priority date	Jul 26, 2017
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

The present invention includes novel compounds containing heterocycles or azaheterocycles and fused phenylene or aza and cyano substituted variants thereof. These compounds may be useful as host materials for phosphorescent electroluminescent devices. In some embodiments, the invention includes compounds of Formula I:

First claim

We claim:

1. A compound of Formula I

wherein T 1 to T 20 are independently selected from the group consisting of CR T and N, and W 1 to W 6 are independently selected from the group consisting of CR W and N, wherein there is no more than two N in each 6-member aromatic ring;
each R T and each R W is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, deuterated alkyl, cycloalkyl, deuterated cycloalkyl, heteroalkyl, deuterated heteroalkyl, arylalkyl, deuterated arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, pyridine, pyrimidine, pyrazine, triazine, nitrile, isonitrile, benzonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; optionally, any two adjacent R T can join to form a ring, or an R W can join with a proximate R T to form a 5-membered ring,
with the proviso that when each of W 3 , W 4 , W 5 and W 6 are CR W , then at most one of these R W are aryl, heteroaryl or silyl.

2. The compound of claim 1 , wherein each R T and each R W is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3. The compound of claim 1 , wherein each R T and each R W is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof.

4. The compound of claim 2 , wherein at least one of R T and/or R W is a polycyclic group selected from the group consisting of:

wherein
X 1 to X 30 are independently selected from the group consisting of N and CR X , but no single 6-membered aromatic ring can have more than three N; wherein R x is defined as R T above;
Y is selected from the group consisting of C and Si;
Z 1 and Z 2 are independently selected from the group consisting of NR 1 , BR 1 , N, O, S, Se, CR 1 R 2 , SiR 1 R 2 , and GeR 1 R 2 ; wherein R 1 and R 2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof; and
L 1 , L 2 , L 3 , and L 4 are independently selected from the group consisting of O, S, BR 1 , NR 1 , CR 1 R 2 and SiR 1 R 2 .

5. The compound of claim 1 , wherein each of T 1 to T 20 are C.

6. The compound of claim 1 , wherein T 1 to T 8 and T 11 to T 18 , collectively, include 2, 4, 6, or 8 N ring atoms; and/or T 9 , T 10 , T 19 , and T 20 , collectively include 2 N ring atoms.

7. The compound of claim 1 , wherein W 3 to W 6 , collectively include 2 N ring atoms.

8. The compound of claim 3 , having a structure of Formula II

wherein R 1 is representative of R W , or a polycyclic group selected from the group consisting of

wherein
X 1 to X 20 are independently selected from the group consisting of N and CR X , but no single 6-membered aromatic ring can have more than three N; wherein R X is defined as R T above;
Z 1 and Z 2 are independently selected from the group consisting of NR 1 , BR 1 , N, O, S, Se, CR 1 R 2 , SiR 1 R 2 , and GeR 1 R 2 ; and
wherein R 1 and R 2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof.

9. The compound of claim 3 , having a structure of Formula III

wherein R 3 to R 6 , and R 3′ to R 6′ , are independently R T , and R 1 , R 1′ , R 2 , R 2′ are independently R W , or optionally, one to four of R 3 to R 6 , and R 3 to R 6′ , are a polycyclic group, and/or one of R 1 , R 1′ , R 2 , R 2′ is a polycyclic group, wherein the polycyclic group is selected from the group consisting of

wherein X 1 to X 20 are independently selected from the group consisting of N and CR X , but no single 6-membered aromatic ring can have more than three N; wherein R X is defined as R T above;
Z 1 and Z 2 are independently selected from the group consisting of NR 1 , BR 1 , N, O, S, Se, CR 1 R 2 , SiR 1 R 2 , and GeR 1 R 2 ; wherein R 1 and R 2 are independently selected from the group consisting of deuterium, alkyl, aryl, heteroaryl, and combinations thereof.

10. The compound of claim 1 , wherein each R T and each R W are independently selected from the group consisting of:
hydrogen;
alkyl selected from the group consisting of methyl, ethyl, propyl, i-propyl, t-butyl, and partially or fully deuterated analogs thereof;
aryl selected from the group consisting of phenyl, naphthyl, and partially or fully deuterated analogs of each thereof; each of which is optionally substituted at an ortho position;
heteroaryl selected from the group consisting of pyridyl, pyrazinyl, pyrimidyl, triazinyl, carbazoyl, dibenzofuran, dibenzothiophene, benzimidazole[2,1-b]benzothiazole, 5H-benzimidazo[1,2-a]benzimidazole, benzimidazo[2,1-b]benzoxazole, aza-carbazoyl, aza-dibenzofuran, aza-dibenzothiophene, aza-benzimidazole[2,1-b]benzothiazole, aza-5H-benzimidazo[1,2-a]benzimidazole and aza-benzimidazo[2,1-b]benzoxazole, and partially or fully deuterated analogs of each thereof; each of which is optionally substituted at an ortho position;
wherein substitution at the ortho position is a substituent selected from methyl, ethyl, propyl, i-propyl, or t-butyl, and partially or fully deuterated analogs of each thereof.

11. The compound of claim 9 , wherein R 1 to R 6 , and R 1′ to R 6′ , are independently selected from the group consisting of:
hydrogen;
alkyl selected from the group consisting of methyl, ethyl, propyl, i-propyl, t-butyl, and partially or fully deuterated analogs thereof;
aryl selected from the group consisting of phenyl, naphthyl, and partially or fully deuterated analogs of each thereof; each of which is optionally substituted at an ortho position;
heteroaryl selected from the group consisting of pyridyl, pyrazinyl, pyrimidyl, triazinyl, carbazoyl, dibenzofuran, dibenzothiophene, benzimidazole[2,1-b]benzothiazole, 5H-benzimidazo[1,2-a]benzimidazole, benzimidazo[2,1-b]benzoxazole, aza-carbazoyl, aza-dibenzofuran, aza-dibenzothiophene, aza-benzimidazole[2,1-b]benzothiazole, aza-5H-benzimidazo[1,2-a]benzimidazole and aza-benzimidazo[2,1-b]benzoxazole, and partially or fully deuterated analogs of each thereof; each of which is optionally substituted at an ortho position;
wherein substitution at the ortho position is a substituent selected from methyl, ethyl, propyl, i-propyl, or t-butyl, and partially or fully deuterated analogs of each thereof.

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

Assignees

• Universal Display Corp

Inventors

• Wolohan Peter
• Macinnis Morgan C

Classifications

• H10K85/625

  containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene · CPC title

• C07D311/82 Primary

  Xanthenes · CPC title

• C07D337/14

  [b,f]-condensed · CPC title

• C07D339/00

  Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title