IP Library › Granted Patent US 9,385,328
Granted Patent B2
US 9,385,328 · App. 13/419,863 · Granted Jul 5, 2016

Composite material, light-emitting element, light-emitting device, electronic device, and lighting device

Inventors: Kaori Ogita (Isehara, JP); Hiromi Nowatari (Atsugi, JP); Harue Osaka (Sagamihara, JP); Takahiro Ushikubo (Ashikaga, JP); Satoshi Seo (Sagamihara, JP); Takako Takasu (Chigasaki, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H01L51/0085C07F15/0033C09K11/06H01L51/0052H05B33/14C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1092H01L51/0072
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Quick Facts
Patent No.
US 9,385,328
App. No.
13/419,863
Granted
Jul 5, 2016
Kind
B2
Abstract

A composite material which includes an organic compound and an inorganic compound and has a high carrier-transport property is provided. A composite material having a good property of carrier injection into an organic compound is provided. A composite material in which light absorption due to charge-transfer interaction is unlikely to occur is provided. A composite material having a high visible-light-transmitting property is provided. A composite material including a hydrocarbon compound and an inorganic compound exhibiting an electron-accepting property with respect to the hydrocarbon compound is provided. The hydrocarbon compound has a substituent bonded to a naphthalene skeleton, a phenanthrene skeleton, or a triphenylene skeleton and has a molecular weight of 350 to 2000, and the substituent has one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

Claims (82)

1. A light-emitting device comprising a light-emitting element, the light-emitting element comprising:

a first electrode;

a layer comprising a composite material of a hydrocarbon compound and an inorganic compound over the first electrode;

a second electrode over the layer; and

a hole transport layer between the layer and the second electrode,

wherein the hydrocarbon compound has a skeleton selected from a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton,

wherein the skeleton is bonded to a substituent having one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring,

wherein a molecular weight of the hydrocarbon compound is greater than or equal to 350 and less than or equal to 2000,

wherein the hydrocarbon compound has an absorption peak at a shorter wavelength than a visible-light wavelength, and

wherein the hole transport layer comprises a compound represented by a structural formula (G6) or (G7):

2. The light-emitting device according to claim 1 , wherein the inorganic compound is a transition metal oxide.

3. The light-emitting device according to claim 2 , wherein the transition metal oxide is one or more types of oxides selected from titanium oxide, vanadium oxide, tantalum oxide, molybdenum oxide, tungsten oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, and silver oxide.

4. The light-emitting device according to claim 1 , wherein the substituent is a phenyl group.

5. The light-emitting device according to claim 1 , wherein the substituent is bonded to the α- or β-position of the naphthalene skeleton, the 9-position of the phenanthrene skeleton, or the 2-position of the triphenylene skeleton.

6. The light-emitting device according to claim 1 , wherein the hydrocarbon compound is represented by a general formula (G1):

wherein:

R 1 to R 9 independently represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 10 to R 14 independently represent any of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group, and

the other or others of R 19 to R 14 independently represent any of hydrogen, and an alkyl group having 1 to 6 carbon atoms.

7. The light-emitting device according to claim 1 , wherein the hydrocarbon compound is represented by a general formula (G2):

wherein:

R 21 to R 27 independently represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 30 to R 34 independently represent any of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group, and

the other or others of R 30 to R 34 independently represent any of hydrogen, and an alkyl group having 1 to 6 carbon atoms.

8. The light-emitting device according to claim 1 , wherein the hydrocarbon compound is represented by a general formula (G3):

wherein:

R 41 to R 47 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 50 to R 54 independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and

the other or others of R 50 to R 54 independently represent hydrogen, and an alkyl group having 1 to 6 carbon atoms.

9. The light-emitting device according to claim 1 , wherein the hydrocarbon compound is represented by a general formula (G4):

wherein:

R 61 to R 71 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 80 to R 84 independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and

the other or others of R 80 to R 84 independently represent any of hydrogen, and an alkyl group having 1 to 6 carbon atoms.

10. The light-emitting device according to claim 1 , wherein the hydrocarbon compound is represented by a general formula (G5):

wherein:

α 1 to α 3 independently represent a phenylene group or a biphenylene group,

Ar 1 to Ar 3 independently represent a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and

k, n, and m independently represent 0 or 1.

11. The light-emitting device according to claim 10 , wherein the naphthyl group is α-naphthyl group or a β-naphthyl group, the phenanthryl group is a 9-phenanthryl group, and the triphenylenyl group is a triphenylen-2-yl group.

12. An electronic device comprising the light-emitting device according to claim 1 .

13. A lighting device comprising a light-emitting element, the light-emitting element comprising:

a first electrode;

a layer comprising a composite material of a hydrocarbon compound and an inorganic compound over the first electrode;

a second electrode over the layer; and

a hole transport layer between the layer and the second electrode,

wherein the hydrocarbon compound has a skeleton selected from a naphthalene skeleton, a phenanthrene skeleton, and a triphenylene skeleton,

wherein the skeleton is bonded to a substituent having one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring,

wherein a molecular weight of the hydrocarbon compound is greater than or equal to 350 and less than or equal to 2000,

wherein the hydrocarbon compound has an absorption peak at a shorter wavelength than a visible-light wavelength,

wherein the hole transport layer comprises the hydrocarbon compound, and

wherein the hole transport layer comprises a compound represented by a structural formula (G6) or (G7):

14. The lighting device according to claim 13 , wherein the inorganic compound is a transition metal oxide.

15. The lighting device according to claim 14 , wherein the transition metal oxide is one or more types of oxides selected from titanium oxide, vanadium oxide, tantalum oxide, molybdenum oxide, tungsten oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, and silver oxide.

16. The lighting device according to claim 13 , wherein the substituent is a phenyl group.

17. The lighting device according to claim 13 , wherein the substituent is bonded to the α- or β-position of the naphthalene skeleton, the 9-position of the phenanthrene skeleton, or the 2-position of the triphenylene skeleton.

18. The lighting device according to claim 13 , wherein the hydrocarbon compound is represented by a general formula (G1):

wherein:

R 1 to R 9 independently represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 19 to R 14 independently represent any of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group, and

the other or others of R 19 to R 14 independently represent any of hydrogen, and an alkyl group having 1 to 6 carbon atoms.

19. The lighting device according to claim 13 , wherein the hydrocarbon compound is represented by a general formula (G2):

wherein:

R 21 to R 27 independently represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 30 to R 34 independently represent any of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group, and

the other or others of R 30 to R 34 independently represent any of hydrogen, and an alkyl group having 1 to 6 carbon atoms.

20. The lighting device according to claim 13 , wherein the hydrocarbon compound is represented by a general formula (G3):

wherein:

R 41 to R 47 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 50 to R 54 independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and

the other or others of R 50 to R 54 independently represent any of hydrogen, and an alkyl group having 1 to 6 carbon atoms.

21. The lighting device according to claim 13 , wherein the hydrocarbon compound is represented by a general formula (G4):

wherein:

R 61 to R 71 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms in a ring,

one or more of R 80 to R 84 independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and

the other or others of R 80 to R 84 independently represent any of hydrogen, and an alkyl group having 1 to 6 carbon atoms.

22. The lighting device according to claim 13 , wherein the hydrocarbon compound is represented by a general formula (G5):

wherein:

α 1 to α 3 independently represent a phenylene group or a biphenylene group,

Ar 1 to Ar 3 independently represent a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylenyl group, and

k, n, and m independently represent 0 or 1.

23. The lighting device according to claim 22 , wherein the naphthyl group is α-naphthyl group or a β-naphthyl group, the phenanthryl group is a 9-phenanthryl group, and the triphenylenyl group is a triphenylen-2-yl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2012
From: OGITA, KAORI; NOWATARI, HIROMI; OSAKA, HARUE; USHIKUBO, TAKAHIRO; SEO, SATOSHI; TAKASU, TAKAKO
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 027862/0402 →
Priority Claims (2)
JP 2011-064629 · Mar 23, 2011 · national
JP 2011-122829 · May 31, 2011 · national
Continuity (1)
Related Publication 20120241727A1 · Sep 27, 2012