IP Library › Granted Patent US 8,404,362
Granted Patent B2
US 8,404,362 · App. 12/668,819 · Granted Mar 26, 2013

Organic light-emitting element using triazine ring-containing polymer compound

Inventor: Masahiko Toba (Chiba, JP)
Assignee: Showa Denko K.K.
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Quick Facts
Patent No.
US 8,404,362
App. No.
12/668,819
Granted
Mar 26, 2013
Kind
B2
Abstract

The organic light-emitting element of the present invention is an organic light-emitting element constituted by arranging a light-emitting layer between an anode and a cathode, and is characterized in that the light-emitting layer contains a polymer compound comprising a constitutional unit derived from an electron transport polymerizable compound represented by the following formula (1) and a constitutional unit derived from a phosphorescent polymerizable compound; wherein R 1 to R 14 are each independently a hydrogen atom, a halogen atom, a cyano group, an amino group, an alkyl group of 1 to 12 carbon atoms or the like, R 15 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 1 is a single bond or the like.

Claims (39)

1. An organic light-emitting element constituted by arranging a light-emitting layer between an anode and a cathode, wherein the light-emitting layer contains a polymer compound comprising a constitutional unit derived from an electron transport polymerizable compound represented by the following formula (1) and a constitutional unit derived from a phosphorescent polymerizable compound;

wherein in formula (1), R 7 and R 14 are each independently an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and R 1 to R 6 and R 8 to R 13 are hydrogen atoms, R 15 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 1 is a single bond or a group represented by any one of the following formulas (X11) to (X14):

wherein R X11 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X12 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group, and

wherein the polymer compound further comprises a constitutional unit derived from a hole transport polymerizable compound represented by formula (8-3):

2. The organic light-emitting element as claimed in claim 1 , wherein the phosphorescent polymerizable compound is a complex represented by any one of the following formulas (2) to (4):

wherein R 201 to R 215 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, in each of R 201 to R 204 , R 205 to R 208 , R 209 to R 211 , and R 212 to R 215 , two groups bonded to carbon atoms adjacent to each other on a ring may be bonded to each other to form a condensed ring, R 216 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 2 is a single bond or a group represented by any one of the following formulas (X21) to (X24):

wherein R X21 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X22 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group;

wherein R 301 to R 308 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 309 to R 310 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, in each of R 301 to R 304 , and R 305 to R 308 , two groups bonded to carbon atoms adjacent to each other on a ring may be bonded to each other to form a condensed ring, R 311 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 3 is a single bond or a group represented by any one of the following formulas (X31) to (X34):

wherein R X31 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X32 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group;

wherein R 401 to R 411 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, in each of R 401 to R 404 , R 405 to R 408 , and R 409 to R 411 , two groups bonded to carbon atoms adjacent to each other on a ring may be bonded to each other to form a condensed ring, R 412 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 4 is a single bond or a group represented by any one of the following formulas (X41) to (X44):

wherein R X41 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X42 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group.

3. A surface-emitting light source comprising the organic light-emitting element as claimed in claim 1 .

4. An image display comprising the organic light-emitting element as claimed in claim 1 .

5. An organic light-emitting element constituted by arranging a light-emitting layer between an anode and a cathode, wherein the light-emitting layer contains a polymer compound comprising a constitutional unit derived from an electron transport polymerizable compound represented by the following formula (1) and a constitutional unit derived from a phosphorescent polymerizable compound;

wherein R 7 and R 14 are each independently an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and R 1 to R 6 and R 8 to R 13 are hydrogen atoms, R 15 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 1 is a single bond or a group represented by any one of the following formulas (X11) to (X14):

wherein R X11 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X12 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group, and

wherein the light-emitting layer further contains a hole transport polymer compound having a structural unit derived from a polymerizable compound represented by formula (8-3):

6. The organic light-emitting element as claimed in claim 5 , wherein the phosphorescent polymerizable compound is a complex represented by any one of the following formulas (2) to (4):

wherein R 202 and R 204 are fluorine atoms, R 206 and R 213 are t-Bu groups, R 201 , R 203 , R 205 , R 207 to R 212 , R 214 and R 215 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 216 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 2 is a single bond or a group represented by any one of the following formulas (X21) to (X24):

wherein R X21 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X22 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group;

wherein R 302 and R 304 are fluorine atoms, R 306 is t-Bu group, R 301 , R 303 , R 305 , R 307 and R 308 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 309 to R 310 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 311 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 3 is a single bond or a group represented by any one of the following formulas (X31) to (X34):

wherein R X31 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X32 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group;

wherein R 402 and R 404 are fluorine atoms, R 406 is t-Bu group, R 401 , R 403 , R 405 , and R 407 to R 411 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 412 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 4 is a single bond or a group represented by any one of the following formulas (X41) to (X44):

wherein R X41 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X42 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group.

7. A polymer compound comprising a constitutional unit derived from an electron transport polymerizable compound represented by the following formula (1) and a constitutional unit derived from a phosphorescent polymerizable compound;

wherein R 7 and R 14 are each independently an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and R 1 and R 6 and R 8 and R 13 are hydrogen atoms, R 15 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 1 is a single bond or a group represented by any one of the following formulas (X11) to (X14):

wherein R X11 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X12 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group,

said polymer compound further comprising a constitutional unit derived from a hole transport polymerizable compound represented by formula (8-3):

8. An organic light-emitting element constituted by arranging a light-emitting layer between an anode and a cathode, wherein the light-emitting layer contains a polymer compound comprising a constitutional unit derived from an electron transport polymerizable compound represented by the following formula (1) and a constitutional unit derived from a phosphorescent polymerizable compound;

wherein formula (1), R 7 and R 14 are each independently an alkyl group of 1 to 12 carbon atoms or an alkoxy group of 1 to 12 carbon atoms, and R 1 to R 6 and R 8 to R 13 are hydrogen atoms, R 15 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 1 is a single bond or a group represented by any one of the following formulas (X11) to (X14):

wherein R X11 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X12 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group,

wherein the polymer compound further comprises a constitutional unit derived from a hole transport polymerizable compound represented by formula (8-3):

and wherein the phosphorescent polymerizable compound is a complex represented by any one of the following formulas (2) to (4):

wherein R 202 and R 204 are fluorine atoms, R 206 and R 213 are t-Bu groups, R 201 , R 203 , R 205 , R 207 to R 212 , R 214 and R 215 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 216 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 2 is a single bond or a group represented by any one of the following formulas (X21) to (X24):

wherein R X21 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X22 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group;

wherein R 302 and R 304 are fluorine atoms, R 306 is t-Bu group, R 301 , R 303 , R 305 , R 307 and R 308 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 309 to R 310 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 311 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 3 is a single bond or a group represented by any one of the following formulas (X31) to (X34):

wherein R X31 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X32 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group;

wherein R 402 and R 404 are fluorine atoms, R 406 is t-Bu group, R 401 , R 403 , R 405 , and R 407 to R 411 are each independently an atom or a substituent selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, an alkyl group of 1 to 10 carbon atoms, an aryl group of 6 to 10 carbon atoms, an amino group which may be substituted by an alkyl group of 1 to 10 carbon atoms, an alkoxy group of 1 to 10 carbon atoms and a silyl group, R 412 is a hydrogen atom or an alkyl group of 1 to 12 carbon atoms, and X 4 is a single bond or a group represented by any one of the following formulas (X41) to (X44):

wherein R X41 is a single bond or an alkylene group of 1 to 12 carbon atoms, and R X42 is a single bond, an alkylene group of 1 to 12 carbon atoms or a phenylene group.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2014
From: SHOWA DENKO K.K.
To: SAMSUNG ELECTRONICS CO., LTD
Reel/Frame 033709/0095 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2010
From: TOBA, MASAHIKO
To: SHOWA DENKO K.K.
Reel/Frame 023767/0551 →
Priority Claims (1)
JP 2007-184402 · Jul 13, 2007 · national
Continuity (1)
Related Publication 20100201258A1 · Aug 12, 2010