Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12167678-B2
Application number	US-202218065193-A
Country	US
Kind code	B2
Filing date	Dec 13, 2022
Priority date	Feb 22, 2019
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

A compound of Formula I:wherein:X1-X8 are each independently C or N, wherein two adjacent X1-X8 are carbon-fused to a structure of Formula II:X9-X12 are each independently C or N;A1, A2, and A3 are each independently selected from the group consisting of O, S, Se, N, NR, CR, CRR′, SiR, SiRR′, GeR, and GeRR′, with at least one of A1 and A2 being N or NR;each occurrence of is independently a single bond or a double bond, wherein one occurrence of is a single bond and one occurrence of is a double bond;each of RA, RB, and RC independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;each of occurrence R, R′, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of R, R′, RA, RB, and RC comprising a group of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, or Formula IX:each occurrence of Y1, Y2, and Y3 is independently absent, O, S, Se, NR, CRR′, SiRR′, or GeRR′;each occurrence of Ar1, and Ar2 is independently an optionally substituted aryl group or an optionally substituted heteroaryl group, wherein Ar1 and Ar2 are optionally joined or fused together to form a ring;each occurrence of X13-X20 is independently C or N, with the proviso that at least one of X13-X20 is N;each occurrence of A4 is selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, and GeRR′;each occurrence of RX independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;each occurrence of RX is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;each occurrence of RY is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula IX, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;the maximum number of N atoms that are connected to each other within a ring is two; andany two substituents are optionally joined or fused together to form a ring.

First claim

We claim:

1. A compound of Formula I:

wherein:
X 1 -X 8 are each independently C or N, wherein two adjacent X 1 -X 8 are carbon-fused to a structure of Formula II:

X 9 -X 12 are each independently C or N;
A 1 , A 2 , and A 3 are each independently selected from the group consisting of O, S, Se, N, NR, CR, CRR′, SIR, SiRR′, GeR, and GeRR′, with at least one of A 1 and A 2 being N or NR;
each occurrence of is independently a single bond or a double bond, wherein one occurrence of is a single bond and one occurrence of is a double bond;
each of R A , R B , and R C independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;
each of occurrence R, R′, R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, Formula IX, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, with at least one of R, R′, R A , R B , and R C comprising a group of Formula III, Formula IV, Formula V, Formula VI, Formula VII, Formula VIII, or Formula IX:

each occurrence of Y 1 , Y 2 , and Y 3 is independently absent, O, S, Se, NR, CRR′, SiRR′, or GeRR′;
each occurrence of Ar 1 and Ar 2 is independently an optionally substituted aryl group or an optionally substituted heteroaryl group, wherein Ar 1 and Ar 2 are optionally joined or fused together to form a ring;
each occurrence of X 13 _X 20 is independently C or N;
each occurrence of A 4 is selected from the group consisting of O, S, Se, NR, CRR′, SiRR′, and GeRR′;
each occurrence of R X independently represents zero, mono, or up to a maximum allowed substitution to its associated ring;
each occurrence of R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
each occurrence of R Y is independently a hydrogen or a substituent selected from the group consisting of Formula III, Formula IV, Formula V, Formula VI, Formula IX, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
the maximum number of N atoms that are connected to each other within a ring is two; and
any two substituents are optionally joined or fused together to form a ring.

2. The compound of claim 1 , wherein one of R, R A or R B comprises a group of Formula III:

wherein Y 1 -Y 3 , and R X are each as defined in claim 1 .

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

4. The compound of claim 2 , wherein Y 1 , Y 2 , and Y 3 are each independently absent, O or NR, with R being an aryl or heteroaryl group.

5. The compound of claim 2 , wherein Y 1 and Y 2 are each O, and Y 3 is absent.

6. The compound of claim 2 , wherein each occurrence of R X is independently hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, or combinations thereof.

7. The compound of claim 1 , wherein one of R, R A or R B has Formula VI:

wherein X 13 -X 20 , A 4 , and R X are each as defined in claim 1 .

8. The compound of claim 7 , wherein each occurrence of R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

9. The compound of claim 7 , wherein A 4 is NR.

10. The compound of claim 9 , wherein R is aryl or heteroaryl group.

11. The compound of claim 7 , wherein one of X 13 -X 16 is N.

12. The compound of claim 7 , wherein each occurrence of R X is independently hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, or combinations thereof.

13. The compound of claim 1 , wherein one of R, R A or R B has Formula VII or VIII:

wherein R X and R Y are both as defined in claim 1 .

14. The compound of claim 13 , wherein each occurrence of R X is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

15. The compound of claim 13 , wherein R Y is a phenyl group.

16. The compound of claim 13 , wherein each occurrence of R X is independently hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, or combinations thereof.

17. The compound of claim 7 , wherein A 4 is O.

18. The compound of claim 7 , wherein A 4 is S.

19. The compound of claim 7 , wherein A 4 is Se.

20. The compound of claim 7 , wherein two of X 13 -X 20 are N.

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Wolohan Peter

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/40 Primary

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• C07D493/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/18

  Carrier blocking layers · CPC title