Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12545690-B2
Application number	US-202217672895-A
Country	US
Kind code	B2
Filing date	Feb 16, 2022
Priority date	Oct 25, 2019
Publication date	Feb 10, 2026
Grant date	Feb 10, 2026

Abstract

Provided are new compositions of matter for host materials in OLEDs by incorporating deuterated moieties in the organic molecules. Also provided are formulations comprising these deuterated compounds. Further provided are OLEDs and related consumer products that utilize these deuterated compounds.

First claim

What is claimed is:

1 . A compound selected from the group consisting of Formula (1) to Formula (16) shown below:

wherein at least one of R A , and at least one of R B is D,

wherein at least one of R C and R D is D,

wherein at least one of R E , R F , R G , and R H is D,

wherein at least one of R I , R J , and R K is D,

wherein at least one of R L , R M , and R N is D,

wherein at least one of R O , R P , and R Q is D,

wherein at least one of R R and R 8 is D,

wherein at least one of R T , R U , R V , and R W is D,

wherein at least one of R X and R Y is D,

wherein at least one of R AB and R AC is D,

wherein at least one of R AF and R AG is D,

wherein at least one of R AL and R AM , and at least one of R AN is D,

wherein at least one of R AT , R AU , R AV , and R AW is D, and

wherein at least one of R AY and R AZ is D;
wherein:
R A to R BB each independently represents mono to the maximum allowable substitution, or no substitution;
X 1 -X 138 are each independently C or N;
at least one of X 1 to X 8 and one of X 114 to X 116 is N;
at least one of X 32 and X 34 is C;
Y 1 to Y 5 each independently is selected from the group consisting of O, S, and Se;
one of Y 2 and Y 3 can also present no bond;
L is a direct bond or an organic linker;
at least one of R E , R F , R G , and RH is selected from the group consisting of aryl, heteroaryl, amino, silyl, boryl, and combinations thereof;
any two adjacent substituents of R A to R S , R AL to R AO , R AY , R AZ , R BA , and R BB can join or fuse into a ring; provided that any two adjacent substituents of R L , R M , and R N do not join or fuse into a indolo[3,2,1-jk]carbazole;

each R Y is H or D;
at least one of R 2 and R 3 comprises a chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and boron atom;
R 8 is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
each R A to R AO , R AT to R BB , R 1 to R 7 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein the compound is at least 20% deuterated;
when compound is formula (14), at least one of the following two conditions is true:
(a) each R AP to R AS is independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof; at least one of R AP to R AS is unique; and the compound only comprises one Si; and
(b) each R AP to R AS is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and
at least one of R AP , one of R AQ , one of R AR , and one of R AS is deuterium; any two adjacent R AP to R AS can be joined or fused to form a ring; at least one of R AP to R AS comprises a group selected from the group consisting of triazine, pyrimidine, pyridine, pyrazine, boryl, silane, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, tetraphenylene, biscarbazole, and combinations thereof;
provided that each R AP to R AS does not comprises a 6-membered ring containing exactly one B and exactly one N; and
with the proviso that the compound is not:

2 . The compound of claim 1 , wherein each X 9 to X 113 , X 117 to X 121 is C.

3 . The compound of claim 1 , wherein at least one of X 1 to X 8 , at least one of X 9 to X 16 , at least one of X 17 to X 31 , and X 122 , at least one of X 32 to X 42 , at least one of X 43 to X 53 , at least one of X 34 to X 68 , at least one of X 69 to X 83 , at least one of X 84 to X 98 , at least one of X 99 to X 113 , at least one of X 114 to X 116 , and at least one of X 117 to X 121 is N.

4 . The compound of claim 1 , wherein at least one of R A and R B , at least one of R C , R D , and R 1 , at least one of R E to R G , at least one of R I to R K , at least one of R L to R N , at least one of R O to R Q , at least one of R R and R S , at least one of R T to R W , and R 4 , at least one of R X to R AA , and R 5 , at least one of R AB to R AE , and R 6 , at least one of R AF to R AI , and R 7 , at least one of R AJ , R AK and R 8 , at least one of R AL to R AN , and at least one of R AP to R AS comprises a chemical group selected from the group consisting triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, silyl, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and boron atom.

5 . The compound of claim 1 , wherein the compound is formula (4), wherein (i) (Y 2 , Y 3 ) pair is selected f

Assignees

• Universal Display Corp

Inventors

• Fleetham Tyler
• Thompson Nicholas J
• Lin Chun
• Feldman Jerald
• Wolohan Peter
• Ma Bin

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title