IP Library › Granted Patent US 11,024,808
Granted Patent B2
US 11,024,808 · App. 15/393,971 · Granted Jun 1, 2021

Organic electroluminescent materials and devices

Inventors: Hsiao-Fan Chen (Ewing, NJ); Jason Brooks (Ewing, NJ); Nicholas J. Thompson (Ewing, NJ)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0067C07D209/86C07D251/24C09K11/06H01L51/0072C09K2211/1007C09K2211/1029C09K2211/1059C09K2211/185H01L51/0085H01L51/5016H01L2251/5384
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Quick Facts
Patent No.
US 11,024,808
App. No.
15/393,971
Granted
Jun 1, 2021
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 (52)

1. A compound selected from the group consisting of:

i) a compound represented by

wherein R 1 to R 3 each independently represent mono to possible maximum allowable number of substitution, or no substitution; and R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein m is an integer from 1 to 10;

wherein none of R 1 to R 3 represents perfluorophenyl; 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 triazine;

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.

2. The compound of claim 1 , wherein G 1 further comprises at least one chemical group selected from the group consisting of benzoimidazole, triphenylamine, triphenylborane, carbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, triphenylene, fluorene, tetraarylsilyl, 9,10-dihydroanthracene, xanthene, thioxanthene, selenoxanthene, 9,10-dihydroacridine, dibenzo-1,4-dioxin, phenoxazine, phenothiazine, thianthrene, phenoxaselenine, dibenzo[b,e][1,4]oxasiline, dibenzo[b,e][1,4]thiasiline, dibenzo[b,e][1,4]selenasiline, 5,10-dihydrosilanthrene, aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, aza-triphenylene, aza-fluorene, and tetraheteroarylsilyl.

3. The compound of claim 2 , wherein each of triazine, benzoimidazole, triphenylamine, triphenylborane, carbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, triphenylene, fluorene, tetraarylsilyl, 9,10-dihydroanthracene, xanthene, thioxanthene, selenoxanthene, 9,10-dihydroacridine, dibenzo-1,4-dioxin, phenoxazine, phenothiazine, thianthrene, phenoxaselenine, dibenzo[b,e][1,4]oxasiline, dibenzo[b,e][1,4]thiasiline, dibenzo[b,e][1,4]selenasiline, 5,10-dihydrosilanthrene, aza-carbazole, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, aza-triphenylene, aza-fluorene, and tetraheteroarylsilyl 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 G 1 is 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 , 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.

9. The compound of claim 1 , wherein G 1 comprises triazine 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.

10. A formulation comprising the compound of claim 1 .

11. A compound 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 the compound of claim 11 .

13. 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 represented by

wherein R 1 to R 3 each independently represent mono to possible maximum allowable number of substitution, or no substitution; and R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein m is an integer from 1 to 10;

wherein none of R 1 to R 3 represents perfluorophenyl; 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 triazine;

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.

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

15. The OLED of claim 13 , 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.

16. The OLED of claim 13 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer.

17. The OLED of claim 13 , wherein the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.

18. The OLED of claim 13 , wherein the organic layer is an emissive layer and the compound of Formula I is an emitter.

19. The OLED of claim 13 , wherein the organic layer is an emissive layer and the compound of Formula I is a delayed fluorescent emitter.

20. The OLED of claim 13 , 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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2016
From: CHEN, HSIAO-FAN; BROOKS, JASON; THOMPSON, NICHOLAS J.
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 040804/0760 →
Continuity (2)
Provisional Application 62272347 · Dec 29, 2015
Related Publication 20170186970A1 · Jun 29, 2017