Granted Patent B2

US 12,378,197 · App. 16/441,058 · Granted Aug 5, 2025

Inventors: Hsiao-Fan Chen (Taipei, TW); Peter Wolohan (Princeton Junction, NJ); Nicholas J. Thompson (Hamilton, NJ)

Assignee: UNIVERSAL DISPLAY CORPORATION

C07D209/82C07C211/54C07C255/51C07D241/46C07D251/24C07D265/38C07D279/22C07D295/033C07D487/04C07D491/048C07D495/04H10K85/341H10K85/631H10K85/654H10K85/656H10K85/6572H10K50/12H10K50/16H10K50/18H10K2101/20

Abstract

Claims (114)

1. A compound having exactly one structure of Formula I:

wherein Z 1 to Z 16 are each CR or N;

wherein three consecutive ones of Z 1 to Z 16 within the same ring cannot be N;

wherein each R is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one R comprises a donor substituent selected from the group consisting of carbazole, indolocarbazole, indoloindole, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, diphenylamino,

phenoxazine, phenothiazine, dibenzoazasiline, pyrrolidine, piperidine, phenoxide, and methoxide;

wherein at least one R comprises an acceptor substituent selected from the group consisting of a halogen, a nitrile group, a 5-membered aromatic ring containing at least two heteroatoms, and a 6-membered heteroaromatic ring;

wherein the at least one R comprising a donor substituent and the at least one R comprising an acceptor substituent are different;

wherein at least one of the following is true: (i) wherein at least one R comprises a donor substituent selected from the group consisting of indolocarbazole, indoloindole, phenoxazine, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, dibenzoazasiline, and pyrrolidine, or (ii) the compound has exactly one donor substituent and exactly one acceptor substituent, and the acceptor substituent comprises heteroaryl; and

wherein any two Rs on the same 6-membered ring can be joined or fused together to form a ring, and Rs from different 6-membered rings cannot be joined, with the proviso that if the acceptor is selected from the group consisting of aza-carbazole, aza-dibenzofuran and aza-dibenzothiophene, then the donor is not carbazole.

2. The compound of claim 1 , wherein at least one R comprises at least one acceptor group selected from the group consisting of cyano, pyrazole, imidazole, triazole, pyridine, pyrimidine, triazine, aza-carbazole, aza-dibenzofuran, and aza-dibenzothiophene group.

3. The compound of claim 1 , wherein each one of Z 1 through Z 16 is CR.

4. The compound of claim 3 , wherein the exactly one donor substituent comprises carbazole.

5. The compound of claim 1 , wherein at least one of Z 1 through Z 16 is N.

6. The compound of claim 1 , wherein at least one R comprises a chemical group selected from the group consisting of

wherein R′ is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, aryl, and heteroaryl.

7. The compound of claim 1 wherein the compound has exactly one donor substituent and exactly one acceptor substituent, and the acceptor substituent comprises heteroaryl.

8. A formulation comprising a compound according to claim 1 .

9. A chemical structure selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule, wherein the chemical structure comprises a monovalent or polyvalent variant of a compound of claim 1 .

10. The compound of claim 1 , wherein a maximum of one R per 6-membered ring is not hydrogen.

11. The compound of claim 1 , wherein at least one of the 6-membered rings of Formula I has two Rs that comprise nitrile.

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

an anode;

a cathode; and

an organic layer, disposed between the anode and cathode, comprising a compound of claim 1 .

13. A compound selected from the group consisting of the following compounds:

Compound Z

Structure of Compound Z

Ar 1 , Ar 2 , Ar 3 , Ar 4

Z

Compound 1 to Compound 540,000 having the structure

wherein Ar 1 = Di, Ar 2 = Aj, Ar 3 = Ak, and Ar 4 = Al, wherein i is an integer from 1 to 20, j is an integer from 1 to 30, k is an integer from 1 to 30, and l is an integer from 1 to 30,

wherein Z = i + 20(j − 1) + 600 (k − 1) + 18,000 (l − 1),

Compound 540,001 to Compound 1436,000 having the structure

wherein Ar 1 = Ai, Ar 2 = Dj, Ar 3 = Dk, and Ar 4 = Dl, wherein i is an integer from 1 to 14, j is an integer from 1 to 40, k is an integer from 1 to 40, and l is an integer from 1 to 40,

wherein Z = i + 14(j − 1) + 560 (k − 1) + 22,400 (l − 1) + 540,000,

Compound 1,436,001 to Compound 1,468,000 having the structure

wherein Ar 1 = Ai, Ar 2 = Dj, Ar 3 = Dk, and Ar 4 = Dl, wherein i is an integer from 29 to 30, j is an integer from 1 to 40, k is an integer from 1 to 20, and l is an integer from 1 to 20,

wherein Z = (i − 28) + 2(j − 1) + 80(k − 1) +1,600 (l − 1) + 1,4360,000,

Compound 1,468,001 to Compound 1,484,000 having the structure

wherein Ar 1 = Ai, Ar 2 = Dj, Ar 3 = Dk, and Ar 4 = Dl, wherein i is an integer from 29 to 30, j is an integer from 21 to 40, k is an integer from 1 to 20, and l is an integer from 21 to 40,

wherein Z = (i − 28) + 2(j − 21) + 40(k − 1) + 800 (l −21) + 1,468,000,

Compound 1,484,001 to Compound 2,204,000 having the structure

wherein Ar 1 = Di, Ar 2 = Aj, Ar 3 = Ak, and Ar 4 = Al, wherein i is an integer from 1 to 20, j is an integer from 1 to 40, k is an integer from 1 to 30, and i is an integer from 1 to 30,

wherein Z = i + 20(j − 1) + 800 (k − 1) + 24,000 (l − 1) + 1,484,000,

Compound 2,204,001 to Compound 2,924,000 having the structure

wherein Ar 1 = Di, Ar 2 = Aj, Ar 3 = Dk, and Ar 4 = Al, wherein i is an integer from 1 to 20, j is an integer from 1 to 30, k is an integer from 1 to 40, and l is an integer from 1 to 30,

wherein Z = i + 20(j − 1) + 600 (k − 1) + 24,000 (l − 1) + 2,204,000,

Compound 2,924,001 to Compound 2,946,400 having the structure

wherein Ar 1 = Di, Ar 2 = Aj, and Ar 3 = Dk, wherein i is an integer from 1 to 40, j is an integer from 1 to 14, and k is an integer from 1 to 40,

wherein Z = i + 14(j − 1) + 560 (k − 1) + 2,924,000,

Compound 2,946,401 to Compound 2,948,000 having the structure

wherein Ar 1 = Di, Ar 2 = Aj and Ar 3 = Dk, wherein i is an integer from 1 to 40, j is an integer from 29 to 30, and k is an integer from 1 to 20,

wherein Z = i + 40(j − 29) + 80 (k − 1) + 2,946,400,

Compound 2,948,001 to Compound 2,948,800 having the structure

wherein Ar 1 = Di, Ar 2 = Aj, and Ar 3 = Dk, wherein i is an integer from 21 to 40, j is an integer from 29 to 30, and k is an integer from 21 to 40,

wherein Z = (i − 20) + 2(j − 29) + 40(k − 21) + 2,948,000,

Compound 2,948,801 to Compound 2,966,800 having the structure

wherein Ar 1 = Ai, Ar 2 = Dj, and Ar 3 = Ak, wherein i is an integer from 1 to 30, j is an integer from 1 to 20, and k is an integer from 1 to 30,

wherein Z = i + 30(j − 1) + 600 (k − 1) + 2,948,800,

Compound 2,966,801 to Compound 3,014,800 having the structure

wherein Ar 1 = Di, Ar 2 = Dj, and Ar 3 = Ak, wherein i is an integer from 1 to 40, j is an integer from 1 to 40, and k is an integer from 1 to 30,

wherein Z = i + 40(j − 1) + 1,600(k − 1) + 2,966,800,

Compound 3,014,801 to Compound 3,062,800 having the structure

wherein Ar 1 = Ai, Ar 2 = Dj, and Ar 3 = Dk, wherein i is an integer from 1 to 30, j is an integer from 1 to 40, and k is an integer from 1 to 40,

wherein Z = i + 30(j − 1) + 1,200(k − 1) + 3,014,800,

Compound 3,062,801 to Compound 3,063,400 having the structure

wherein Ar 1 = Di and Ar 2 = Aj, wherein i is an integer from 1 to 20 and j is an integer from 1 to 30,

wherein Z = i + 20(j − l) + 3,062,800,

Compound 3,063,401 to Compound 3,064,600 having the structure

wherein Ar 1 = Di and Ar 2 = Aj, wherein i is an integer from 1 to 40 and j is an integer from 1 to 30,

wherein Z = i + 40(j − 1) + 3,063,400;

with the proviso that donor D2 cannot be present in the same compound as any acceptor selected from the group consisting of A7-A10, A13, A14, A24-A26, and A28-A29;

with the proviso that at least one of the following moieties is present: D2-D5, D7, D10-D20, D23-D25, D27, D30, D32-D40, A2-10, A12-15, and A18-A30;

with the proviso that if the donor substituent is DI or D11, then the acceptor substituent is not A1, A11, or A17;

wherein D1 to D40 have the following structures:

and

wherein A1 to A30 have the following structures:

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

an anode;

a cathode; and

an emissive layer, disposed between the anode and cathode, wherein the emissive layer comprises a compound that is an emitter having a structure of Formula I:

wherein Z 1 to Z 16 are each CR or N;

wherein three consecutive ones of Z 1 to Z 16 within the same ring cannot be N;

wherein each R is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one R comprises a donor substituent selected from the group consisting of carbazole, indolocarbazole, indoloindole, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, diphenylamino, phenoxazine, phenothiazine, dibenzoazasiline, pyrrolidine, piperidine, phenoxide, and methoxide;

wherein at least one R comprises an acceptor substituent selected from the group consisting of a halogen, a nitrile group, a 5-membered aromatic ring containing at least two heteroatoms, and a 6-membered heteroaromatic ring;

wherein the at least one R comprising a donor substituent and the at least one R comprising an acceptor substituent are different;

wherein at least one of the following is true: (i) wherein at least one R comprises a donor substituent selected from the group consisting of indolocarbazole, indoloindole, phenothiazine, diphenylamino, phenoxazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, dibenzoazasiline, pyrrolidine, piperidine, and phenoxide, or (ii) at least one acceptor substituent comprises aryl or heteroaryl, and each of Z 1 to Z 16 is CR;

if the donor substituents is diphenylamino and the acceptor substituent is nitrile, then two Rs on the same 6-membered ring cannot be joined to form a 5-membered ring; and

wherein any two Rs on the same 6-membered ring can be joined or fused together to form a ring, and Rs from different 6-membered rings cannot be joined, with the proviso that if the acceptor is selected from the group consisting of aza-carbazole, aza-dibenzofuran and aza-dibenzothiophene, then the donor is not carbazole.

15. A consumer product comprising an organic light-emitting device (OLED) of claim 14 .

16. The consumer product of claim 15 , wherein the consumer product is selected from the group consisting of a flat panel display, a curved display, a computer monitor, a medical monitors 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, a light therapy device, and a sign.

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

an anode;

a cathode; and

an organic layer, disposed between the anode and cathode, comprising a compound having a structure of Formula I:

wherein Z 1 to Z 16 are each CR or N;

wherein three consecutive ones of Z 1 to Z 16 within the same ring cannot be N;

wherein each R is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein at least one R comprises a donor substituent selected from the group consisting of carbazole, indolocarbazole, indoloindole, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, diphenylamino, phenoxazine, phenothiazine, dibenzoazasiline, pyrrolidine, piperidine, phenoxide, and methoxide;

wherein at least one R comprises an acceptor substituent selected from the group consisting of a halogen, a nitrile group, a 5-membered aromatic ring containing at least two heteroatoms, and a 6-membered heteroaromatic ring;

wherein the at least one R comprising a donor substituent and the at least one R comprising an acceptor substituent are different;

wherein at least one of the following is true: (i) each of Z 1 to Z 16 is CR, (ii) wherein at least one R comprises a donor substituent selected from the group consisting of indolocarbazole, indoloindole, phenothiazine, diphenylamino, phenoxazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, dibenzoazasiline, pyrrolidine, piperidine, and phenoxide, (iii) at least one donor substituent comprises aryl or heteroaryl, or (iv) at least one acceptor substituent comprises aryl or heteroaryl; and

wherein any two Rs on the same 6-membered ring can be joined or fused together to form a ring, and Rs from different 6-membered rings cannot be joined, with the proviso that if the acceptor is selected from the group consisting of aza-carbazole, aza-dibenzofuran and aza-dibenzothiophene, then the donor is not carbazole, wherein the OLED emits a luminescent radiation at room temperature when a voltage is applied across the first organic light emitting device; wherein the luminescent radiation comprises a delayed fluorescent process.

18. The OLED of claim 17 , wherein the organic layer further comprises a sensitizer; and wherein the sensitizer is a phosphorescent emitting material.

19. The OLED of claim 14 , wherein the organic layer further comprises a phosphorescent emitting material comprising a metal atom selected from the group consisting of Os, Ir, Pd, Pt, Cu, and Au.

20. The OLED of claim 19 , wherein the phosphorescent emitting material further comprises at least one ligand 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″ can be fused or joined to form a ring;

wherein each R a , R b , R c , and R d represents from a mono substitution to a maximum possible number of substitutions, 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, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, 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 can be fused or joined to form a ring or form a multidentate ligand.

Assignments (1)

Continuity (2)

References Cited (194)