IP Library › Granted Patent US 11,818,948
Granted Patent B2
US 11,818,948 · App. 17/234,216 · Granted Nov 14, 2023

Organic electroluminescent materials and devices

Inventors: Hsiao-Fan Chen (Ewing, NJ); Jason Brooks (Ewing, NJ); Nicholas J. Thompson (Ewing, NJ)
Assignee: Universal Display Corporation
H10K85/654C07D209/86C07D251/24C09K11/06H10K85/6572C09K2211/1007C09K2211/1029C09K2211/1059C09K2211/185H10K50/11H10K85/342H10K2101/10H10K2101/90
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Quick Facts
Patent No.
US 11,818,948
App. No.
17/234,216
Granted
Nov 14, 2023
Kind
B2
Abstract

Host materials with pentafluorophenyl substitution are described. These compounds are designed for, and used for hosting aza substituted dopants that may be susceptible to intramolecular deprotonation. In addition, the fluorinated substitution aids with electron transport within the emissive layer.

Claims (73)

1. A compound selected from the group consisting of:

i) a compound of Formula I:

wherein G is an organic group comprising at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl;

wherein G can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein m and n are each independently an integer from 1 to 10;

and wherein any two adjacent substituents can optionally join or fuse into a ring; and

ii) a compound represented by the following Formula:

wherein n is an integer from 1 to 10;

wherein G 1 is an organic group comprising at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl;

wherein G 1 can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and

wherein any two adjacent substituents can optionally join or fuse into a ring;

provided that when G or G 1 comprises carbazole, then n is an integer from 4 to 10;

provided that when G comprises two carbazole groups, then n is an integer from 5 to 10 or at least one m is an integer of 2 to 10; and

provided that when G or G 1 comprises tetraarylsilyl, then at least one substituent on G or G 1 is not fluorine or perfluoroaryl.

2. The compound of claim 1 , wherein each of carbazole and tetraarylsilyl can be used no more than twice.

3. The compound of claim 1 , wherein each of carbazole and tetraarylsilyl can be used only once.

4. The compound of claim 1 , wherein n is at least 2.

5. The compound of claim 1 , wherein n is at least 3.

6. The compound of claim 1 , wherein m is 1.

7. The compound of claim 1 , wherein m is 2.

8. The compound of claim 1 , wherein the compound has a formula selected from the group consisting of:

wherein G 1 is an organic group comprising at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl;

wherein G 1 can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

and wherein any two adjacent substituents can optionally join or fuse into a ring.

9. The compound of claim 1 , wherein G and G 1 are selected from the group consisting of:

wherein R 1 to R 4 each independently represent mono to possible maximum allowable number of substitution, or no substitution;

wherein R 1 to R 4 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

10. The compound of claim 1 , wherein G and G 1 comprises at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl; and at least one chemical group selected from the group consisting of triazine, benzoimidazole, triphenylamine, triphenylborane, aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, aza-triphenylene, aza-fluorene, and tetraheteroarylsilyl.

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

12. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound selected from the group consisting of:

i) a compound of Formula I:

wherein G is an organic group comprising at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl;

wherein G can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein m and n are each independently an integer from 1 to 10;

and wherein any two adjacent substituents can optionally join or fuse into a ring; and

ii) a compound represented by the following Formula:

wherein n is an integer from 1 to 10;

wherein G 1 is an organic group comprising at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl;

wherein G 1 can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and

wherein any two adjacent substituents can optionally join or fuse into a ring;

provided that when G or G 1 comprises carbazole, then n is an integer from 4 to 10;

provided that when G comprises two carbazole groups, then n is an integer from 5 to 10 or at least one m is an integer of 2 to 10; and

provided that when G or G 1 comprises tetraarylsilyl, then at least one substituent on G or G 1 is not fluorine or perfluoroaryl.

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

14. The OLED of claim 12 , wherein the organic layer further comprises a phosphorescent 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 carbon and nitrogen;

wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, SiR′R″, and GeR′R″;

wherein R′ and R″ are optionally fused or joined to form a ring;

wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;

wherein R′, R″, R a , R b , R c , and R d are each 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, and

wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

15. The OLED of claim 12 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer.

16. The OLED of claim 12 , wherein the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.

17. The OLED of claim 12 , wherein the organic layer is an emissive layer and the compound of Formula I is an emitter.

18. The OLED of claim 12 , wherein the organic layer is an emissive layer and the compound of Formula I is a delayed fluorescent emitter.

19. The OLED of claim 12 , wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.

20. A formulation comprising a compound selected from the group consisting of:

i) a compound of Formula I:

wherein G is an organic group comprising at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl;

wherein G can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,

wherein m and n are each independently an integer from 1 to 10;

and wherein any two adjacent substituents can optionally join or fuse into a ring; and

ii) a compound represented by the following Formula:

wherein n is an integer from 1 to 10;

wherein G 1 is an organic group comprising at least one chemical group selected from the group consisting of carbazole and tetraarylsilyl;

wherein G 1 can be further substituted by one or more substituents selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, haloaryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and

wherein any two adjacent substituents can optionally join or fuse into a ring;

provided that when G or G 1 comprises carbazole, then n is an integer from 4 to 10;

provided that when G comprises two carbazole groups, then n is an integer from 5 to 10 or at least one m is an integer of 2 to 10; and

provided that when G or G 1 comprises tetraarylsilyl, then at least one substituent on G or G 1 is not fluorine or perfluoroaryl.

Continuity (3)
Continuation 15393971 · Dec 29, 2016
Provisional Application 62272347 · Dec 29, 2015
Related Publication 20210249608A1 · Aug 12, 2021