Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2024246999-A1
Application number	US-202418410105-A
Country	US
Kind code	A1
Filing date	Jan 11, 2024
Priority date	Oct 25, 2019
Publication date	Jul 25, 2024
Grant date	—

Abstract

Provided are boron-containing compounds. Also provided are formulations comprising these boron-containing compounds. Further provided are OLEDs and related consumer products that utilize these boron-containing compounds.

First claim

1 . An organic light emitting device (OLED) comprising:
an anode; a cathode; and an emissive layer disposed between the anode and the cathode, wherein the emissive layer comprises a first compound and a second compound; wherein the first compound is a boron compound possessing a trigonal planar geometry; and wherein the second compound is a Pt(II) complex possessing a square planar geometry.

2 . The OLED of claim 1 wherein the first compound comprises a structure of Formula I:

wherein:
X 1 -X 9 are each independently C or N;
no more than two N atoms are bonded to one another;
L 1 , L 2 , and L 3 are each independently selected from the group consisting of O, S, Se, BR, NR, CRR′, SiRR′, and GeRR′;
L 1 is optionally present, and L 2 and L 3 are always present;
R 1 , R 2 , and R 3 each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R, R′, R 1 , R 2 , and R 3 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; and
the second compound is a Pt complex capable of emitting light at room temperature upon photo or electrical excitation.

3 . The OLED of claim 1 , wherein the Pt complex comprises a tetradentate ligand.

4 . The OLED of claim 1 , wherein the Pt complex comprises at least one Pt—C bond,
and at least one Pt—N bond.

5 . The OLED of claim 1 , wherein the Pt complex is a phosphorescent emitter.

6 . The OLED of claim 1 , wherein the Pt complex has at least one ligand or part of
the ligand if the ligand is more than bidentate selected from the group consisting of:

wherein each Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen;
wherein Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
wherein R e and R f are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
wherein each of R a , R b , R c , R d , R e and R f 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 acid, 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 are optionally fused or joined to form a ring or form a multidentate ligand.

7 . The OLED of claim 1 , wherein the Pt complex is selected from the group consisting of:

wherein L, for each occurrence, is independently O, S, Se, BR, NR, CRR′, SiRR′, and GeRR′;
wherein each of R, R 1 , R A , R B , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , and R N is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

8 . The OLED of claim 1 , wherein each R, R′, R 1 , R 2 , and R 3 is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

9 . The OLED of claim 1 , wherein L 1 is not present.

10 . The OLED of claim 1 , wherein L 2 and L 3 are each O.

11 . The OLED of claim 1 , wherein L 2 and L 3 are each NR.

12 . The OLED of claim 1 , wherein one of L 2 and L 3 is O, and the other is NR.

13 . The OLED of claim 1 , wherein R is a 6-membered aromatic ring.

14 . The OLED of claim 1 , wherein at least one of R 1 , R 2 , and R 3 comprises a chemical group selected from the group consisting of carbazole, dibenzofuran, dibenzothiophene, tetraphenylene, triazine, pyrimidine, pyridine, tetraphenylene, 512-enzo[d]benzo[4,5]imidazo[3,2-a]imidazole, benzo[d]benzo[4,5]imidazo[2,1-b]oxazole, benzo[d]benzo[4,5]imidazo[2,1-b]thiazole, 5H-612-indolo[2,3-b]indole, 6H-benzofuro[2,3-b]indole, 6H-benzo[4,5]thieno[2,3-b]indole, and aza variants thereof.

15 . The OLED of claim 1 , wherein the first compound comprises a structure from the group consisting of:

ring A and D are each independently a monocyclic or multicyclic ring system comprising one or more fused 5-membered or 6-membered carbocyclic or heterocyclic rings;
L 4 is a direct bond or an aromatic group comprising one or more fused or unfused aromatic rings which can be further substituted;
wherein X 17 is selected from the group consisting of O, S, Se, and NR 4 ;
wherein each of R F , R P , R Q , and R R is independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
wherein each R 4 , R A , R B , R C , R D , R E , R F , R P , R Q , and R R is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

16 . The OLED of claim 1 , wherein the first compound is selected from the group consisting of

Assignees

• Universal Display Corp

Inventors

• Wolohan Peter
• Fleetham Tyler
• Feldman Jerald

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/104

  with other heteroatoms · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• H10K50/121

  for assisting energy transfer, e.g. sensitization · CPC title

• H10K85/346

  comprising platinum · CPC title