IP Library › Granted Patent US 10,840,458
Granted Patent B2
US 10,840,458 · App. 15/594,743 · Granted Nov 17, 2020

Organic electroluminescent materials and devices

Inventors: Bin Ma (Plainsboro, NJ); Alan Deangelis (Pennington, NJ); Lichang Zeng (Lawrenceville, NJ); Chuanjun Xia (Lawrenceville, NJ); Jerald Feldman (Wilmington, DE)
Assignee: UNIVERSAL DISPLAY CORPORATION
H01L51/0072C07D487/04C09K11/025C09K11/06H01L27/3213H01L51/0052H01L51/0073H01L51/0074H05B33/14H05B33/20C09K2211/1007C09K2211/1018C09K2211/1029C09K2211/185H01L51/0067H01L51/0085H01L51/5012H01L51/5016H01L51/5024H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096H01L2251/5376
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Quick Facts
Patent No.
US 10,840,458
App. No.
15/594,743
Granted
Nov 17, 2020
Kind
B2
Abstract

Novel organic materials containing indolocarbazoles as donor connected with electron acceptors such as quinoxaline or dibenzoquinoxaline for PHOLED devices are disclosed.

Claims (59)

1. A compound is selected from the group consisting of:

wherein R 1 , R 2 , and R 3 each independently represents mono to a maximum possible number of substitutions, or no substitution;

wherein any adjacent substituents of R 1 , R 2 , and R 3 are not joined or fused into any ring;

wherein L 1 and L 2 each independently represents a direct bond or an organic linker and are not condensed with R 1 , R 2 , or R 3 to form a ring;

wherein R 1 , R 2 , R 3 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;

wherein each of G 1 and G 2 is independently selected from the group consisting of:

and substituted variants thereof;

wherein at least one of G 1 or G 2 is selected from the group consisting of

and

wherein the dash line represents the connecting bond.

2. The compound of claim 1 , wherein at least one of G 1 and G 2 is selected from the group consisting of:

3. The compound of claim 1 , wherein L 1 and L 2 are each independently selected from the group consisting of direct bond, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

4. 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:

wherein R 1 , R 2 , and R 3 each independently represents mono to a maximum possible number of substitutions, or no substitution;

wherein any adjacent substituents of R 1 , R 2 , and R 3 are not joined or fused into any ring;

wherein L 1 and L 2 each independently represents a direct bond or an organic linker and are not condensed with R 1 , R 2 , or R 3 to form a ring;

wherein R 1 , R 2 , and R 3 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;

wherein each of G 1 and G 2 is independently selected from the group consisting of:

and substituted variants thereof;

wherein at least one of G 1 or G 2 is selected from the group consisting of

and

wherein the dash line represents the connecting bond.

5. The OLED of claim 4 , wherein at least one of G 1 and G 2 is selected from the group consisting of:

6. The OLED of claim 4 , wherein L 1 and L 2 are each independently selected from the group consisting of direct bond, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

7. The OLED of claim 4 , wherein the organic layer is an emissive layer comprising a host and a phosphorescent emissive dopant, wherein the compound is the host.

8. The OLED of claim 4 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the phosphorescent 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.

9. The OLED of claim 4 , wherein the organic layer is a charge carrier blocking layer and the compound is a charge carrier blocking material.

10. The OLED of claim 4 , wherein the organic layer is a charge carrier transporting layer and the compound is a charge carrier transporting material.

11. The OLED of claim 4 , wherein the organic layer is an emissive layer and the compound of Formula I is an emitter.

12. The OLED of claim 11 , wherein the OLED emits a luminescent radiation at room temperature when a voltage is applied across the organic light emitting device, and wherein the luminescent radiation comprises a delayed fluorescence process.

13. The OLED of claim 11 , wherein the emissive layer further comprises a host material.

14. The OLED of claim 11 , wherein the emissive layer further comprises a first phosphorescent emitting material.

15. The OLED of claim 14 , wherein the emissive layer further comprises a second phosphorescent emitting material.

16. The OLED of claim 14 , wherein the OLED emits a white light at room temperature when a voltage is applied across the organic light emitting device.

17. The OLED of claim 16 , wherein the compound comprising a structure according to Formula I emits a blue light with a peak wavelength of about 400 nm to about 500 nm.

18. A consumer product comprising 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:

wherein R 1 , R 2 , and R 3 each independently represents mono to a maximum possible number of substitutions, or no substitution;

wherein any adjacent substituents of R 1 , R 2 , and R 3 are not joined or fused into any ring;

wherein L 1 and L 2 each independently represents a direct bond or an organic linker and are not condensed with R 1 , R 2 , or R 3 to form a ring;

wherein R 1 , R 2 , and R 3 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;

wherein each of G 1 and G 2 is independently selected from the group consisting of:

and substituted variants thereof;

wherein at least one of G 1 or G 2 is selected from the group consisting of

and

wherein the dash line represents the connecting bond.

19. The consumer product of claim 18 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video walls comprising multiple displays tiled together, a theater or stadium screen, and a sign.

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

Assignments (1)
NUNC PRO TUNC ASSIGNMENT Recorded May 24, 2017
From: MA, BIN; DEANGELIS, ALAN; ZENG, LICHANG; XIA, CHUANJUN; FELDMAN, JERALD
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 042491/0640 →
Continuity (2)
Provisional Application 62341207 · May 25, 2016
Related Publication 20170346022A1 · Nov 30, 2017