Organic electroluminescent materials and devices

• US 9,711,730 B2
• Filed: 12/31/2015
• Issued: 07/18/2017
• Est. Priority Date: 01/25/2015
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Lin, Chun
• Primary Examiner(s): Lebentritt, Michael
• Application Number:
  US14/985,837
• Publication Number:
  US 20160218294A1
• Time in Patent Office: 565 Days
• Field of Search: None
• CPC Class Codes: C07C 22/08 containing fluorine
• CPC Class Codes: C07C 23/46 with more than three condensed rings
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 491/052 the oxygen-containing ring being six-membered
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/125 specially adapted for multicolour light emission, e.g. for emitting white light
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• 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 85/623 : containing five rings, e.g. pentacene
• CPC Class Codes: H10K 85/624 : containing six or more rings
• CPC Class Codes: H10K 85/625 : containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
• CPC Class Codes: H10K 85/626 : containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/633 : comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/636 : comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/653 : comprising only oxygen as heteroatom
• CPC Class Codes: H10K 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• 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

Abstract

This invention discloses novel light-emitting materials. These materials comprise a side chain which contains at least two Si or Ge atoms, such as bis(trimethylsilyl)methyl, or a side chain that includes Si—F bond, or a side chain that includes a fluorine-containing alkyl chain. This new side chain could fine tune emission color, reduce the stacking of the light-emitting materials, maintain good lifetime, and result in high PLQY.

Claims

1. 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 capable of functioning as a fluorescent emitter in an organic light emitting device at room temperature;

wherein the first compound has at least one aromatic ring comprising at least one substituent R;

wherein each of the at least one R is an organic group selected from the group consisting of (a) a group having at least two atoms of X, (b) a group having at least one X—

F bond, and (c) partially fluorinated alkyl, partially fluorinated cycloalkyl, or combinations thereof;

wherein each X is independently selected from the group consisting of Si and Ge;

wherein each of the at least one R is directly bonded to one of the aromatic rings; and

wherein in each of the at least one R, the C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.

2. The OLED of claim 1, wherein X is directly bonded to the aromatic ring.

3. The OLED of claim 1, wherein X is separated by at least one carbon atom from the aromatic ring.

4. The OLED of claim 1, wherein X connects to its adjacent atoms by X—

C or X—

F bond only.

5. The OLED of claim 1, wherein when each of the at least one R is (b) or (c), the first compound does not have any F atoms other than in the at least one R.

6. The OLED of claim 1, wherein when each of the at least one R is (c), each of the at least one R contains at least one CF₃ group.

7. The OLED of claim 1, wherein when each of the at least one R is (c), none of the at least one R contain any CF₃ groups.

8. The OLED of claim 1, wherein each of the at least one R is independently selected from the group consisting of partially or fully silylated alkyl, partially or fully silylated cycloalkyl, partially or fully germanylated alkyl, partially or fully germanylated cycloalkyl, and combinations thereof.

9. The OLED of claim 1, wherein each of the at least one R is selected from the group consisting of:

10. The OLED of claim 1, wherein each of the at least one R is independently selected from the group consisting of:

11. The OLED of claim 1, wherein each of the at least one R is independently selected from the group consisting of:

12. The OLED of claim 1, wherein each of the at least one R is independently selected from the group consisting of:

13. The OLED of claim 1, wherein the first compound comprises at least one organic group selected from the group consisting of:

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

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

16. The OLED of claim 1, wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.

17. The OLED of claim 1, wherein the organic layer further comprises a first phosphorescent emitting material.

18. The OLED of claim 1, wherein the OLED emits a white light.

19. The OLED of claim 16, wherein the OLED is incorporated into a consumer product selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior illumination, a light for exterior lamination, a light for signaling, a heads-up display, a fully transparent display, a partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, a tablet, a phablet, a personal digital assistant (PDA), a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, 3-D display, a vehicle, a large area wall, a theater screen, a stadium screen, and a sign.