Granted Patent B2

US 12,514,109 · App. 17/412,578 · Granted Dec 30, 2025

Inventors: Hsiao-Fan Chen (Ewing, NJ); Jason Brooks (Philadelphia, PA)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/346C07F15/0086C09K11/025C09K11/06H10K85/221C09K2211/1044C09K2211/185H10K50/11H10K2101/10H10K2101/30H10K2101/40H10K2102/311

Abstract

Claims (132)

1 . A compound having a formula:

wherein Ar 1 and Ar 2 are each independently a 5-membered or 6-membered aromatic ring;

wherein X 1 to X 11 are each independently a C or N;

wherein at least one of X 1 to X 11 is N;

wherein one of Z 1 and Z 2 is C, and the other one is N;

wherein when Z 1 is N, X 4 is C;

wherein L 1 is selected from the group consisting of a direct bond, BR′, O, S, CR′R″, SiR′R″, alkyl, cycloalkyl, and combinations thereof;

wherein L 2 is selected from the group consisting of BR′, O, S, CR′R″, SiR′R″, Ph, alkyl, cycloalkyl, and combinations thereof;

wherein L 3 is selected from the group consisting of NR′, BR′, O, S, CR′R″, SiR′R″, Ph, alkyl, cycloalkyl, and combinations thereof;

if L 3 is NR′ or BR′, the R′ forms a ring with R 3 ;

wherein m and n are each independently an integer of 0 or 1, and m+n is at least 1;

wherein when m is 1, X 1 is C; when n is 1, X 11 is C;

wherein R 1 to R 5 each independently represent mono to a maximum possible number of substitutions, or no substitution;

wherein each R 1 to R 5 , R′, and R″ are independently selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents are optionally joined to form into a ring;

wherein one R 4 and one R 5 are joined to form a linker that forms a ring that includes L 1 , wherein if Ar′ is pyrazole that forms an N—Pt bond and an N—Ar 2 bond, then the linker is not alkyl; and

at least one of the following is true:

(1) at least one of X 5 to X 8 is N; or

(2) n=1, L 3 is NR′ or BR′, R′ forms a ring with R 3 , and R′ is pyridine, pyrimidine, pyrazine, or pyridazine.

2 . The compound of claim 1 , wherein m is 0, and n is 1.

3 . The compound of claim 1 , wherein m is 1, and n is 0.

4 . The compound of claim 1 , wherein the ring that includes both the linker and L 1 is an aromatic ring.

5 . The compound of claim 1 , wherein n=1, L 3 is NR′ or BR′ R′ forms a ring with R 3 , and R′ is pyridine, pyrimidine, pyrazine, or pyridazine.

6 . The compound of claim 1 , wherein Z 1 is C, and Z 2 is N.

7 . The compound of claim 1 , wherein at least one R 4 or R 5 that is not part of the linker is selected from the group consisting of alkoxy, aryloxy, amino, silyl, substituted or unsubstituted phenyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, except that phenyl cannot be substituted by aryl or heteroaryl.

8 . The compound of claim 1 , wherein at least one of X 5 to X 8 is N, and X 1 to X 4 are C.

9 . The compound of claim 1 , wherein each six-membered ring having one or more of X 1 to X 11 can have at most one N heteroatom.

10 . The compound of claim 1 , wherein Ar 1 -L 1 -Ar 2 is selected from the group consisting of:

wherein L 2 is not present when m is 0 and L 3 is not present when n is 0, and the dashed lines indicate the point of attachment for L 2 and L 3 when any of them are present;

wherein X 1 is O, S, NR′, BR′, CR′R″, or SiR′R″,

wherein X 2 is O, S, NR′, BR′, CR′R″, SiR′R″, NL 2 , BL 2 , CR′L 2 , or SiR′L 2 ,

wherein X 3 is O, S, NR′, BR′, CR′R″, SiR′R″, NL 3 , BL 3 , CR′L 3 , or SiR′L 3 ;

wherein R represents mono to a maximum possible number of substitutions, or no substitutions;

wherein each R, R a , R b , R c , and R d is independently selected from the group consisting of hydrogen, deuterium, halogen, 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; and

wherein any two adjacent substituents are optionally joined to form into a ring.

11 . The compound of claim 1 , wherein the compound has a structure of

wherein at least one of X 1 to X 8 , and X 12 to X 15 is N;

wherein X 12 to X 15 are each independently a C or N; and

wherein Ar 1 and Ar 2 are each independently a 5-membered or 6-membered aromatic ring;

wherein one of Z 1 and Z 2 is C, and the other one is N; and

wherein when m is 1, X 1 is C; when n is 1, X 11 is C.

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 having a formula:

wherein Ar 1 and Ar 2 are each independently a 5-membered or 6-membered aromatic ring;

wherein X 1 to X 11 are each independently a C or N;

wherein at least one of X 1 to X 11 is N;

wherein one of Z 1 and Z 2 is C, and the other one is N;

wherein when Z 1 is N, X 4 is C;

wherein L 1 is selected from the group consisting of a direct bond, BR′, O, S, CR′R″, SiR′R″, alkyl, cycloalkyl, and combinations thereof;

wherein L 2 is selected from the group consisting of BR′, O, S, CR′R″, SiR′R″, Ph, alkyl, cycloalkyl, and combinations thereof;

wherein L 3 is selected from the group consisting of NR′, BR′, O, S, CR′R″, SiR′R″, Ph, alkyl, cycloalkyl, and combinations thereof;

if L 3 is NR′ or BR′, the R′ forms a ring with R 3 ;

wherein m and n are each independently an integer of 0 or 1, and m+n is at least 1;

wherein when m is 1, X 1 is C; when n is 1, X 11 is C;

wherein R 1 to R 5 each independently represent mono to a maximum possible number of substitutions, or no substitution;

wherein each R 1 to R 5 , R′, and R″ are independently selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents are optionally joined to form into a ring;

wherein one R 4 and one R 5 are joined to form a linker that forms a ring that includes L 1 , wherein if Ar 1 is pyrazole that forms an N—Pt bond and an N—Ar 2 bond, then the linker is not alkyl; and

at least one of the following is true:

(1) at least one of X 5 to X 8 is N; or

(2) n=1, L 3 is NR′ or BR′, R′ forms a ring with R 3 , and R′ is pyridine, pyrimidine, pyrazine, or pyridazine.

13 . The OLED of claim 12 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

14 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

15 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

16 . The OLED of claim 12 , wherein the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved.

17 . The OLED of claim 12 , wherein the OLED further comprises a layer comprising carbon nanotubes.

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 having a formula:

wherein Ar 1 and Ar 2 are each independently a 5-membered or 6-membered aromatic ring;

wherein X 1 to X 11 are each independently a C or N;

wherein at least one of X 1 to X 11 is N;

wherein one of Z 1 and Z 2 is C, and the other one is N;

wherein when Z 1 is N, X 4 is C;

wherein L 1 is selected from the group consisting of a direct bond, BR′, O, S, CR′R″, SiR′R″, alkyl, cycloalkyl, and combinations thereof;

wherein L 2 is selected from the group consisting of BR′, O, S, CR′R″, SiR′R″, Ph, alkyl, cycloalkyl, and combinations thereof;

wherein L 3 is selected from the group consisting of NR′, BR′, O, S, CR′R″, SiR′R″, Ph, alkyl, cycloalkyl, and combinations thereof;

if L 3 is NR′ or BR′, the R′ forms a ring with R 3 ;

wherein m and n are each independently an integer of 0 or 1, and m+n is at least 1;

wherein when m is 1, X 1 is C; when n is 1, X 11 is C;

wherein R 1 to R 5 each independently represent mono to a maximum possible number of substitutions, or no substitution;

wherein each R 1 to R 5 , R′, and R″ are independently selected from the group consisting of hydrogen, deuterium, halogen, 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 any two adjacent substituents are optionally joined to form into a ring;

wherein one R 4 and one R 5 are joined to form a linker that forms a ring that includes L 1 , wherein if Ar 1 is pyrazole that forms an N—Pt bond and an N—Ar 2 bond, then the linker is not alkyl; and

at least one of the following is true:

(1) at least one of X 5 to X 8 is N; or

(2) n=1, L 3 is NR′ or BR′, R′ forms a ring with R 3 , and R′ is pyridine, pyrimidine, pyrazine, or pyridazine.

19 . The consumer product of claim 18 , wherein the consumer product is selected from the group consisting of a flat panel display, a curved 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 rollable display, a foldable display, a stretchable 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 wall 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:

Compound ID

X 5

X 15

X 2

R

Compounds 1 through 14 having the following structure  

 1  2  4  5  6  7  8  9  11  12  13  14

N CH N N CH N N CH N N CH N

CH N N CH N N CH N N CH N N

CH CH CH N N N CH CH CH N N N

H H H H H H Ph Ph Ph Ph Ph Ph

wherein X 2 , X 5 , X 15 , and R are as

defined in this table.

Compound ID

X 5

X 2

R

Compounds 113 through 118 having the following structure  

113 115 116 118

N N N N

CH N CH N

H H Ph Ph

wherein X 2 , X 5 , and R are as defined in this

table.

Compound ID

X 5

X 4

X 3

X 2

R

Compounds 137 through 154 having the following structure  

137 141 142 143 145 146 150 151 152 154

N N N N N N N N N N

CH N CH CH N CH N CH CH N

CH CH N CH CH CH CH N CH CH

CH CH CH N N CH CH CH N N

H H H H H Ph Ph Ph Ph Ph

wherein X 2 , X 3 , X 4 , X 5 , and R are as

defined in this table.

Continuity (3)

References Cited (197)