Organic Electroluminescent Materials and Devices

Patent metadata

Field	Value
Publication number	US-2024147842-A1
Application number	US-202318499614-A
Country	US
Kind code	A1
Filing date	Nov 1, 2023
Priority date	Feb 18, 2016
Publication date	May 2, 2024
Grant date	—

Abstract

The present invention relates to novel light-emitting materials. These materials comprise a side chain that includes a fully deuterated or partially deuterated alkyl chain. This new side chain could improve device lifetime compared to nondeuterated side chains.

First claim

1 .- 22 . (canceled)

23 . An organic light-emitting device (OLED) comprising:
an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a first compound; wherein the first compound is a fluorescent emitter in the OLED at room temperature; wherein the first compound has at least one aromatic ring and at least one substituent R; wherein each of the at least one R is independently selected from the group consisting of partially deuterated alkyl, partially deuterated cycloalkyl, fully deuterated alkyl, fully deuterated cycloalkyl and combinations thereof; wherein each of the at least one R is directly bonded to one of the aromatic rings; wherein in each of the at least one R, C having a deuterium attached thereto is attached to the aromatic ring; wherein the first compound is an emissive dopant that produces emissions via thermally activated delayed fluorescence (TADF) process.

24 . The OLED of claim 23 , wherein the OLED further comprises a first phosphorescent emitting material.

25 . The OLED of claim 24 , wherein the first phosphorescent emitting material is an Ir or Pt complex.

26 . The OLED of claim 25 , wherein the Ir or Pt complex comprises an Ir-carbene or Pt-carbene bond.

27 . The OLED of claim 25 , wherein the Pt complex comprises a tetradentate ligand.

28 . The OLED of claim 23 , wherein the organic layer further comprises a host compound; wherein the host compound comprises at least one of the following groups in the molecule:

wherein each of R 101 to R 107 is 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; k is an integer from 0 to 20; k″′ is an integer from 0 to 20. X 101 to X 108 is selected from C or N;
and Z 101 and Z 102 is selected from NR 101 , O, or S.

29 . The OLED of claim 23 , wherein the organic layer further comprises a host compound comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, silyl, triazine, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

30 . The OLED of claim 23 , wherein the organic layer further comprises a host compound; wherein the host compound comprises a group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group.

31 . The OLED of claim 23 , wherein the organic layer further comprises a host compound; wherein the host compound is a bipolar, an electron transporting, a hole transporting or a wide band gap materials that play little role in charge transport.

32 . The OLED of claim 23 , wherein the organic layer further comprises two or more host compounds; wherein each of the two or more host compounds is a bipolar, an electron transporting, a hole transporting or a wide band gap materials that play little role in charge transport.

33 . The OLED of claim 23 , wherein each of the at least one R is the partially deuterated alkyl, or the fully deuterated alkyl.

34 . The OLED of claim 23 , wherein the alkyl is a branched chain alkyl containing at least four carbon atoms.

35 . The OLED of claim 23 , wherein the alkyl or cycloalkyl contains at least one fluorine atom.

36 . The OLED of claim 23 , wherein the first compound emits light from a singlet excited state to a singlet ground state at room temperature.

37 . The OLED of claim 23 , wherein each of the at least one R is independently selected from the group consisting of:

38 . The OLED of claim 23 , wherein the first compound comprises at least one organic group selected from the group consisting of:

and aza analogues thereof;
wherein A is selected from the group consisting of O, S, Se, NR′ and CR′R″;
wherein R′ and R″ are 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 two adjacent substituents of R′ and R″ are optionally joined to form a ring.

39 . The OLED of claim 23 , wherein the first compound is selected from the group consisting of:

wherein R 1 to R 5 each independently represent from mono to maximum number of substitutions they can have, or no substitution;
wherein R 1 to R 5 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 at least one of R 1 to R 5 is R.

40 . The OLED of claim 23 , wherein the first compound comprises at least one CN group.

41 . 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 first compound; wherein the first compound is a fluorescent emitter in the OLED at room temperature; wherein the first compound has at least one aromatic ring and at least one substituent R; wherein each of the at least one R is independently selected from the group consisting of partially deuterated alkyl, partially deuterated cycloalkyl, fully deuterated alkyl, fully deuterated cycloalkyl and combinations thereof; wherein each of the at least one R is directly bonded to one of the aromatic rings; wherein in each of the at least one R, C having a deuterium attached thereto is attached

Assignees

• Universal Display Corp

Inventors

• Xia Chuanjun
• Lin Chun

Classifications

• H10K85/624 Primary

  containing six or more rings · CPC title

• C07C13/62

  with more than three condensed rings · CPC title

• C07C13/66

  the condensed ring system contains only four rings · CPC title

• C07C211/58

  Naphthylamines; N-substituted derivatives thereof · CPC title

• C07C211/61

  with at least one of the condensed ring systems formed by three or more rings · CPC title