Organic electroluminescent materials and devices

• US 9,406,892 B2
• Filed: 01/07/2015
• Issued: 08/02/2016
• Est. Priority Date: 01/07/2015
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Zeng, Lichang, Joseph, Scott, Yeager, Walter, Dyatkin, Alexey Borisovich, Xia, Chuanjun
• Primary Examiner(s): Diallo, Mamadou
• Application Number:
  US14/591,555
• Publication Number:
  US 20160197285A1
• Time in Patent Office: 573 Days
• US Class Current: 1/1
• CPC Class Codes: C07D 405/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/90 Multiple hosts in the emissive layer
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 50/81 Anodes
• CPC Class Codes: H10K 50/82 Cathodes
• CPC Class Codes: H10K 71/831 Aging
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

A compound having a structure of Formula I:

Formula I, is disclosed. In the structure of Formula I: X is selected from a group consisting of O, S and Se; G² and G³ are each independently selected from benzene, biphenyl, fluorene, naphthalene, phenanthrene, triphenylene, dibenzofuran, dibenzothiophene, dibenzoselenophene, pyridine, pyrimidine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof; L is selected from phenyl, biphenyl, terphenyl and pyridine, and combinations thereof; G², G³ and L are each optionally further substituted with one or more unfused substituents; R¹, R², and each R³, R⁴, R⁵ and R⁶ are an unfused substituent selected from hydrogen, deuterium, alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, halogen, nitro, nitrile, silyl, benzene, biphenyl, terphenyl, pyridine, and combinations thereof; and R¹ and R² are optionally joined to form a ring. Formulations and devices, such as an OLEDs, that include the compound of Formula I, and, optionally a co-host, are also described.

Claims

1. A compound having a structure of Formula I:

2. The compound of claim 1, wherein R¹ and R² are not joined to form a ring.

3. The compound of claim 1, wherein R¹ and R² are joined to form a ring.

4. The compound of claim 1, wherein R¹, R², and each R³, R⁴, R⁵ and R⁶ are an unfused substituent selected from the group consisting of hydrogen, deuterium, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, isopropyl, isobutyl, tert-butyl, tert-butylmethyl, 2-ethylhexyl, 2-ethyloctyl, cyclopentyl, cyclohexyl, benzene, biphenyl, terphenyl, pyridine, naphthalene, quinoline, and combinations thereof.

5. The compound of claim 1, wherein the compound is selected from the group consisting of:

6. The compound of claim 1, wherein the compound has a structure of Formula II:

7. The compound of claim 1, wherein G² and G³ are each independently a moiety selected from the group consisting of:

8. The compound of claim 1, wherein L is a moiety selected from the group consisting of:

9. The compound of claim 1, wherein the compound is selected from the group consisting of:

10. A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:

an anode;

a cathode; and

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

11. The device of claim 10, wherein the organic layer is an emissive layer and the compound of Formula I is a host.

12. The device of claim 10, wherein the organic layer further comprises an emissive dopant, wherein the emissive dopant is a transition metal complex having at least one ligand selected from the group consisting of:

13. The device of claim 10, wherein the organic layer is a blocking layer and the compound having Formula I is a blocking material in the organic layer, or wherein the organic layer is an electron transporting layer and the compound having Formula I is an electron transporting material in the organic layer.

14. The device of claim 10, wherein the device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

15. The device according to claim 10,

wherein the organic layer comprises a first composition comprising a mixture of the first compound and a second compound;

wherein the second compound has a structure of Formula III;

16. A composition of materials comprising a first compound and a second compound,

wherein the first compound has a structure of Formula I:

17. The composition of claim 16, wherein the second compound is selected from the group consisting of:

18. The composition of claim 16, wherein the composition is selected from the group consisting of:

19. The composition of claim 16, wherein the first compound has an evaporation temperature T1 of 150 to 350°

C.;

wherein the second compound has an evaporation temperature T2 of 150 to 350°

C.;

wherein absolute value of T1-T2 is less than 20°

C.;

wherein the first compound has a concentration C1 in said mixture and a concentration C2 in a film formed by evaporating the mixture in a vacuum deposition tool at a constant pressure between 1×

10<sup>−

6</sup> Torr to 1×

10<sup>−

9</sup> Torr, at a 2 Å

/sec deposition rate on a surface positioned at a predefined distance away from the mixture being evaporated; and

wherein absolute value of (C1−

C2)/C1 is less than 5%.

20. The composition of claim 16, wherein the first compound has a first mass loss rate and the second compound has a second mass loss rate, wherein the ratio between the first mass loss rate and the second mass loss rate is within the range of 0.90 to 1.10.