Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12378197-B2
Application number	US-201916441058-A
Country	US
Kind code	B2
Filing date	Jun 14, 2019
Priority date	Jul 13, 2018
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

A compound having a structure of Formula I,

is provided. In Formula I, Z 1 to Z 16 are each CR or N; three consecutive ones of Z 1 to Z 16 within the same ring cannot be N; each R is independently a hydrogen or a substituent selected from a variety of substituents; at least one R includes and electron donor substituent; at least one R includes an electron acceptor substituent; and any two Rs on the same ring can be joined or fused together to form a ring. Organic light emitting devices, consumer products, formulations, and chemical structures containing the compounds are also disclosed.

First claim

We claim:

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

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Wolohan Peter
• Thompson Nicholas J

Classifications

• H10K50/18

  Carrier blocking layers · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title